Run The Numbers

CJ sits down with Mike Jung, Co-Founder and Managing Partner of Founders Circle Capital. They unpack the rise of structured liquidity, how secondaries went mainstream, and what CFOs should know before running a tender. Mike shares lessons from the dot-com era, AI's “super cycle,” and what separates durable growth companies from hype.—SPONSORS:RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNMike: https://www.linkedin.com/in/mikjunghttps://www.founderscircle.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/https://www.mostlymetrics.com—TIMESTAMPS:1:08 Founder Circle origin3:15 The founder liquidity insight5:16 Staying private longer problem6:04 Secondary market control vs chaos8:44 Secondaries over IPOs10:12 Liquidity keeps VC alive11:27 Ask Jeeves dot-com lesson12:26 $190 to $1 + AMT reality13:10 Sponsors — RightRev | Rillet | Tabs16:39 Private share opacity risk20:25 Founder + employee liquidity playbooks21:55 Early investors need liquidity too22:31 Cap table math actually matters24:17 SPV fee stacking insanity25:37 Sponsors — Abacum | Brex | Metronome28:54 Tender offer guardrails30:09 Minimum vs maximum liquidity balance33:01 Growth stage sweet spot + IPO bar rising34:17 AI Cambrian explosion34:58 Buying fear vs buying hype36:29 AI growth sustainability37:19 Founder-led advantage + product velocity38:47 TAM is created, not measured41:06 Anti-portfolio lessons43:01 What is a supercycle44:34 Do supercycles end in crashes?46:16 AI's unprecedented adoption curve48:31 Community as a moat52:50 Earning the right to be on the cap table

In this episode of Run the Numbers, CJ sits down with Mateo Bryant, CFO of Minted. They break down Minted's life-event flywheel and decades-long LTV, managing extreme seasonality when half the year happens in one month, and balancing long-term CAC with short-term monetization. Mateo also shares lessons from scaling Uber and Amazon globally, localization missteps, and making marketplaces work in emerging markets.—SPONSORS:Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNMateo: https://www.linkedin.com/in/bryantmatt/Minted: https://www.minted.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Peter Oey, CFO of Grab:https://youtu.be/tdq0AZO0dLU—TIMESTAMPS:00:00 Intro03:16 Fixer to CFO05:32 Mexico City Startups09:00 Minted Flywheel10:24 LTV Expansion11:04 Entry Points12:18 CAC and Cohorts13:42 Sponsors: Metronome | RightRev | Rillet17:06 Wedding Lifecycle19:49 Holiday Forecasting22:23 Retail Calendar24:03 Cash Flow Swings25:05 Marketing Over Sales26:06 Email Limits27:41 Sponsors: Tabs | Abacum | Brex31:02 Retail Strategy35:08 Global Experience40:47 Uber Cash Economics46:04 Cost of Not Localizing50:19 Importer of Record53:17 No Google Lesson55:34 QBR Mistake56:48 High Leverage Hours59:03 Finance Stack59:50 Seven Day Cruise Expense#RunTheNumbersPodcast #MarketplaceStrategy #EcommerceFinance #GigEconomy #CFOInsights

In this episode of Run the Numbers, CJ sits down with Varsha Udayabhanu of Invisible to unpack what enterprise AI adoption actually looks like beyond the hype. They cover forward deployed engineers, eight-week solution sprints, value-based pricing when outcomes are hard to meter, ARR vs. services revenue, and why “momentum” beats traditional SaaS metrics. A tactical look at trust, expansion, and building durable AI revenue.—SPONSORS:Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai—LINKS: Varsha: https://www.linkedin.com/in/varshaudayabhanu/Company: https://invisibletech.ai/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Marketing as a Form of Capital Allocation With Carta's Head of Growth Angela Winegarhttps://youtu.be/rG09ehsrWv8—TIMESTAMPS:00:00 Intro03:21 What Invisible Technologies Does05:34 Enterprise AI Adoption Gap07:38 Forward Deployed Engineers09:44 Evolving GTM in AI Services10:36 Solution Sprints12:37 Sponsor — Brex | Metronome | RightRev15:56 Upfront Investment vs. Upside18:38 Bespoke Deals20:37 Value-Based Pricing in Enterprise AI22:12 Value Sold vs. Value Delivered23:31 Enterprise Revenue as a Portfolio of Bets24:53 Time-Bound Solution Sprints27:06 Sponsor — Rillet | Tabs | Abacum30:32 Humans in the Loop & Expert Incentives33:38 Niche Human Expertise34:10 Rethinking KPIs Beyond ARR35:44 Momentum Metrics39:00 Evaluating GenAI Financial Profiles40:47 Expansion as the Atomic Unit42:19 AdTech Lessons on Distribution & Brand43:23 Why Brand Matters for Enterprise47:10 Commoditization Risk48:31 Long-Ass Lightning Round53:20 Credits

In this episode, CJ talks with Paul Stansik of ParkerGale Capital about what separates Simplifiers from Complicators. They unpack why most board meetings miss the point, how to answer the actual question, and why naming the real problem builds trust.—SPONSORS:Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run—LINKS: Paul on LinkedIn: https://www.linkedin.com/in/paulstansik/ParkerGale Capital: https://www.parkergale.com/https://hellooperator.substack.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Fixing Broken Windows in Investing3:08 What an Operating Partner Actually Does5:35 Managing Nine Portfolio Companies6:07 Where PE Investors Spend Their Time9:02 Do Investors Think About You All Day?10:16 The Operator “Bermuda Triangle”12:35 Sponsors — Abacum | Brex | Metronome15:52 The CFO “Triangle of Doom”17:47 How to Become an Investor Favorite18:42 Templates Build Trust in Board Communication20:54 Using Trusted Data22:10 The Board Payback Record Scratch23:18 Building Your “Data Diet” With the Board25:19 Sponsors — RightRev | Rillet | Tabs28:47 Signs a Team Isn't in Command31:30 Board Meetings Aren't a Performance34:16 “20 Board Meetings—Don't Waste Them”35:15 Ask Permission to Reallocate the Agenda37:54 When to Send Board Materials40:28 Simplifiers vs. Complicators41:58 The Simplifier Finds the One Question That Matters42:16 Three Traits of a Simplifier: Answer, Find, Do43:15 Why Complicated Operators Take You on a Ride44:26 Selling vs. Substance46:23 “Get There, Bob”47:25 Why We Hedge49:36 You Can't Fix a Secret52:50 Credits

In this episode of Run the Numbers, CJ Gustafson talks with Rivian CFO Claire McDonough about financing one of the most capital-intensive businesses in the world. They cover long-term investment decisions, capacity planning, cash management as production scales, lessons from Rivian's nearly $14B IPO, the risks of over- and under-building, and why federal EV tax credits matter more than most people think.—SPONSORS:Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cj—LINKS: Claire on LinkedIn: https://www.linkedin.com/in/claire-rauh-mcdonough-5291b946/Rivian: https://rivian.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Why Revenue Recognition Is the Next AI Battleground | Dan Miller of RightRevhttps://youtu.be/TxhTtwmOass—TIMESTAMPS:00:00:00 Craziest Expense Story at Rivian00:01:22 Intro to Claire McDonough00:03:09 Capital Intensity and Vertical Integration at Rivian00:06:44 Raising $14B: How Rivian Planned Its IPO Capital00:10:22 Capacity Planning and Scaling R2 Production00:12:13 Sponsors — Tabs, Abacum, Brex00:15:34 Sweating Existing Capacity vs Overbuilding00:18:22 Winning EV Adoption from ICE Buyers00:22:27 How Federal EV Tax Credits Shape EV Pricing00:26:03 Sponsors — Metronome, RightRev, Rillet00:29:27 R2 as a Driver of Long-Term Profitability00:33:14 Supply Chain as the Critical Path to Launch00:36:53 Product Roadmap as the Anchor for Capital and Headcount00:39:40 Peloton and Flipkart Lessons from Banking00:43:42 Biggest Career Mistake00:44:50 Advice to Younger Self00:47:19 Rivian's Finance Software Stack

In this episode of Run the Numbers, CJ Gustafson sits down with Dan Miller, CFO at RightRev. They unpack why leasing is underused in software, how RevTech emerged, and why revenue recognition may be the next AI battleground. Dan also shares how he evaluates durable growth vs. hypergrowth.—SPONSORS:Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com—LINKS: Dan on LinkedIn: https://www.linkedin.com/in/danmillercpa/RightRev: https://www.rightrev.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:00:00:00 Preview and Intro00:02:41 Why Operating Experience Matters for CFOs00:04:08 Defining Durable Growth00:06:06 Snowflake and Consumption Revenue Complexity00:10:17 Forecasting in Consumption Models00:11:29 AI's Role in Revenue Forecasting00:12:14 Sponsors — Rillet | Tabs | Abacus AI00:15:39 Comping Sales in Usage-Based Models00:18:15 Leasing as a Software Monetization Tool00:20:47 The CFO's Role in Sales and GTM00:22:29 How CFOs Help Close Deals00:24:14 Rev Tech vs RevOps00:26:20 Sponsors — Brex | Metronome | RightRev00:29:40 Where AI Actually Helps Rev Rec00:31:55 Deterministic vs Probabilistic AI00:33:05 Why Enterprises Hesitate on AI Agents00:34:18 Startups vs Incumbents in the AI Race00:35:13 FOMO, Overfunding, and Market Distortions00:38:13 CFO Playbooks Without Hypergrowth00:39:38 Finding PMF as a CFO00:41:15 Career Advice: Growth vs Shiny Objects00:42:00 Building the CEO–CFO Relationship00:42:49 Learning Beyond the Back Office00:43:22 Lightning Round00:44:28 Advice to My Younger Self00:45:09 Finance Tech Stack00:46:36 Credits

In this episode of Run the Numbers, CJ sits down with Brett Queener, Managing Director at Bonfire Ventures, to trace the origins of ARR and examine how new revenue models are reshaping B2B software. Drawing on Brett's time at Salesforce and SmartRecruiters, they explore the shift from annual contracts to outcome-based pricing, what it means for forecasting and gtm strategy, and where the next major inflection points in SaaS are likely to emerge.—SPONSORS:RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—LINKS: Brett on LinkedIn: https://www.linkedin.com/in/brettqueener/Brett's Substack: https://queener.substack.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.comThe Staffing Ratios Salesforce Used, with Brett Queener of Bonfire VChttps://youtu.be/lJVgstAXjJs—TIMESTAMPS:00:02:54 Welcome Brett & episode setup00:03:51 On-prem software to SaaS00:05:54 Salesforce & recurring revenue00:07:15 On-prem costs & partner bloat00:09:58 Contracts, control & comp shifts00:14:15 Lock-in, renewals & SaaS drift00:16:20 Sponsors — RightRev | Rillet | Tabs00:19:48 From buying to hiring software00:21:59 Agents change pricing & planning00:25:59 Forecasting without ARR00:28:03 Talent models break00:29:45 Sponsors — Abacum | Brex | Metronome00:33:01 Rethinking sales & comp00:36:47 Selling by doing the job00:40:50 The future role of sales00:46:10 Zombie SaaS & category collapse00:51:07 Context as the moat00:56:07 Where AI hits next00:58:44 Vertical AI & hidden TAMs01:02:12 $1B startups vs mega rounds01:05:48 Dilution, fund math & pressure01:08:03 Choosing your founder path

In this special CFO Explains episode of Run the Numbers, CJ Gustafson sits down with executive producer Ben Hillman to unpack the real history of EBITDA. From John Malone and cable TV to private equity, SaaS, and today's AI boom, CJ explains how a metric invented out of desperation became the default language of valuation—and how adjusted EBITDA can both clarify and distort the truth about a business.—SPONSORS:Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics—LINKS: CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.comSlacker Stuff: https://www.slackerstuff.com/Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/—RELATED EPISODES:How Much Revenue Do You Need to IPO in 2025?https://youtu.be/7ajWVCNVDmI—TIMESTAMPS:00:00:00 Intro00:01:17 The Origins of EBITDA00:06:48 Sponsors — Metronome | RightRev | Rillet00:10:12 The Mechanics of EBITDA00:13:46 Impact on Other Industries00:15:38 The Many Faces of EBITDA00:19:09 Sponsors  — Tabs | Abacum | Brex00:22:30 EBITDA's AI Encore00:24:56 Wrap Up00:28:19 Credits#RunTheNumbersPodcast #CFOExplains #EBITDA #FinancePodcast #BusinessMetrics

In this episode of Run the Numbers, CJ sits down with Dan Griggs, CFO of Intercom, to break down how finance leaders should think about pricing, forecasting, and resource allocation in the AI era. Dan explains why “it's not zero” is his guiding forecasting principle, how Intercom landed on 99 cents per AI resolution for Fin, and what it means to build an AI product that could eventually cannibalize a successful SaaS core. A candid look at managing uncertainty while still making bold bets.—SPONSORS:Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai—LINKS:Dan on LinkedIn: https://www.linkedin.com/in/dan-griggs-0970181/Intercom: https://www.intercom.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Inside Rocket Companies: M&A, Metrics, and Mortgage Moats | Brian Brownhttps://youtu.be/ttedn4AULt8—TIMESTAMPS:00:00:00 Cold Open00:01:03 Intro to Dan Griggs and Intercom's AI Pivot00:02:45 From Ice Cream to SaaS: Early Finance Lessons00:04:19 Learning the Business by Living the Operations00:06:26 Why Operational Reality Shapes Better Forecasts00:08:00 “It's Not Zero”: Forecasting the Unknowable00:10:09 Scenario Planning, Ambiguity, and Psychological Safety00:11:23 Sponsors — Brex | Metronome | RightRev00:14:43 Keeping a Mental Model of Key Business Metrics00:16:15 Using Mental Math to Sanity-Check Forecasts00:17:28 Core Ratios Every CFO Uses to Vet Decisions00:19:13 The Burn-the-Boats Moment for Intercom's AI Pivot00:20:53 Why AI Was an Existential, Not Incremental, Bet00:22:21 Which SaaS Categories AI Can Fully Replace Work00:23:04 Why Finance Hasn't Had Its AI Moment Yet00:23:39 Sponsors — Rillet | Tabs | Abacum00:27:05 Why Fin Needed Outcome-Based Pricing00:28:59 The Tradeoff Behind $0.99 Per Resolution00:30:46 Why Support Conversations Vary in Complexity00:32:01 What Drives the Unit Economics of AI Resolutions00:33:08 How Intercom Chooses Models as Costs Fall00:35:19 Replacing Generic LLMs With Domain-Specific Models00:36:08 Selling an AI Product That Could Cannibalize the Core00:38:50 Founder CEOs Versus Professional CEOs00:41:47 Hiring Mistakes and Acting on Instincts00:44:28 Intercom's Finance Software Stack00:45:49 The Craziest Expense Request#RunTheNumbersPodcast #Intercom #AICustomerSupport #OutcomeBasedPricing #CFOInsights This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ sits down with Maria Izurieta, CFO of Huntress, to unpack what it really means to lead finance as a connective tissue across the organization. Drawing on experience across VC-backed, PE-owned, and public companies, Maria shares how she balances impact versus perfection, builds trust through small wins, and helps teams move from transactional finance to insight-driven decision making. They dig into data transparency, centralized BI, partnering with sales and marketing on revenue, and why the best CFOs unblock friction instead of becoming the “no” department — all while bringing a deeply people-first lens to scale.—SPONSORS:Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run—LINKS:Maria on LinkedIn: https://www.linkedin.com/in/maria-izurieta-909a3b/Company: https://www.huntress.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:How the Best CFOs Lead Without Being the CEO | Ken Stillwellhttps://youtu.be/O4cx9NBqQso—TIMESTAMPS:00:00:00 Preview and Intro00:01:01 Maria's Background00:03:09 People-First Team Building00:05:16 People, Process, Systems at Scale00:07:13 Removing Friction Outside Finance00:09:15 Data Transparency & Decision-Making00:11:06 Sponsors — Abacum | Brex | Metronome00:14:22 Forward-Deployed Data00:16:21 Centralized Data vs. Silos00:19:23 Finance as Data Steward00:21:08 Cost-to-Price Feedback Loop00:22:35 Curiosity Builds Credibility00:23:43 Sponsors — RightRev | Rillet | Tabs00:27:12 Trust First, Then Impact00:30:27 Celebrating Small Wins00:31:21 From Transactions to Insights00:33:00 CFO at the Revenue Table00:34:32 Educating the Org on Metrics00:36:21 Customer-Level Margin Reality00:37:13 Using Facts to Change Decisions00:38:27 Ownership Mindset in Growth Companies00:39:10 VC vs. PE vs. Public CFO Tradeoffs00:41:02 Operating Inside Constraints00:42:18 Finding Your Stage Fit00:44:17 Building a Personal Advisor Network00:46:43 Visibility and Women in Leadership00:47:44 Work–Life Integration, Not Balance00:48:45 Lightning Round: Biggest Mistake00:50:10 Advice to Younger Self00:51:36 Finance Tech Stack00:52:01 Craziest Expense Story00:52:44 Credits#RunTheNumbersPodcast #CFOLeadership #ScalingCompanies #DataDrivenDecisions #ExecutiveLeadership This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ sits down with Ken Stillwell, CFO and COO of Pegasystems, to explore the realities of leading from the second seat. Ken shares hard-earned lessons from guiding Pega through the shift from term licenses to ARR and ACV, including how to rework sales compensation without losing trust or momentum. They discuss the limits of KPI obsession, the importance of directional clarity over false precision, and why private equity often drives sharper execution than public markets—and how to apply that discipline while still playing the long game.—SPONSORS:Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cj—LINKS:Ken on LinkedIn: https://www.linkedin.com/in/ken-stillwell-83a499a/Pegasystems: https://www.pega.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:How Finance Becomes a GTM Partner, Not a Bottleneck | Chris Brubakerhttps://youtu.be/T2YjdoiJtFA—TIMESTAMPS:00:00:00 Preview and Intro00:02:57 Sponsors — Tabs | Abacum | Brex00:07:26 The Strategic Value of Being Number Two00:08:46 Earnings Calls, Messaging, and Real-Time Judgment00:10:41 Using Feedback to Sharpen Executive Communication00:11:38 CFOs as Storytellers & Message Repetition00:12:31 Managing Up: Reading the Room00:13:59 Learning the Hard Way: Misreading Dynamics00:15:18 Confidence, Aggression, and Early CFO Mistakes00:15:58 Sponsors — Metronome | RightRev | Rillet00:19:45 When to Email vs Pick Up the Phone00:22:48 Tailoring Communication to Different Functions00:23:23 Audience-Specific Messaging: “Why Me?”00:25:24 Values vs Behaviors in Leadership00:28:13 Why Big Changes Need Anchoring00:31:14 Moving Pega to the Cloud00:32:43 Rewiring Sales Comp for ARR & ACV00:34:56 Sales Credibility Breakdowns with Customers00:36:20 Economics vs Trust in Sales Teams00:37:48 Balancing Field Feedback with Company Goals00:39:17 De-Emphasizing New Logos to Fix the Sales Model00:41:12 The Danger of Over-Obsessing on KPIs00:42:51 Public vs Private: Incentives and Operating Discipline00:45:57 Why Companies Go Private: Motivation Over Patience00:47:29 The Shrinking Public Markets00:47:57 Private vs Public CFO Mindsets00:49:39 Meeting Investors Where They Are00:50:16 A Risky Decision That Paid Off: Going All-In on the Cloud00:51:29 Long-Ass Lightning Round00:53:24 Ken's Finance Tech Stack & Craziest Expense00:54:39 Credits#RunTheNumbersPodcast #CFOLeadership #ExecutiveCommunication #SalesStrategy #PublicVsPrivate This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ sits down with Chris Brubaker, SVP of Finance at Postscript, who's helped build the finance function from the ground up. Chris shares how he partners with sales through deal desks, sets pricing guardrails, and makes sure finance helps close deals instead of slowing them down. They dig into his hands-on approach to automation using AI with limited engineering resources, how Postscript's metrics evolved as the company scaled, when to trust internal data over benchmarks, and where teams get tripped up. Plus, a private jet accounting story—because of course.—SPONSORS:Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com—LINKS:Chris on LinkedIn: https://www.linkedin.com/in/wchrisbrubaker/Postscript: https://postscript.io/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:So You're Looking for a “Strategic” CFO? Bloomerang's Steve Isom on What That Really Meanshttps://youtu.be/cgHOtvG1CesThe IPO Playbook: Expert Advice from Lee Kirkpatrick, Twilio's Former CFOhttps://youtu.be/PTKAUD7PSWUThe CFO Case for Probabilistic Forecasting With AI | Bruno Annicqhttps://youtu.be/Dl8nDZPJMpE—TIMESTAMPS:00:00:00 Preview and Intro00:02:22 Sponsors — Rillet | Tabs | Abacum00:06:55 Interview Begins00:07:36 First Finance Hire and Early Scale at Postscript00:09:02 Usage-Based Margins, COGS, and the Twilio Parallel00:10:31 Partnering With Sales and Building Deal Desk00:13:16 Pricing Guardrails, Payback, and Deal Economics00:15:35 How Deal Desk Evolves Over Time00:16:01 Sponsors — Brex | Metronome | RightRev00:19:44 Making Finance a Deal-Closing Partner00:20:44 Automating Deal Desk With a Slack Bot00:23:48 How Technical Finance Leaders Need to Be00:25:17 Automating Without Engineering Help00:27:12 Why Human Touch Still Matters in SaaS00:27:53 Postscript's Finance Tech Stack00:28:30 ERP Migration and Month-End Efficiency00:29:42 The Reality of Continuous Close00:30:34 First Real AI Wins in Accounting00:31:18 Experimenting With AI Forecasting00:33:32 Metrics That Matter: Usage as a Leading Indicator00:35:49 How Metrics Evolve as the Company Scales00:37:41 Understanding the Product in a Usage-Based Model00:39:27 Micro-Seasonality and Forecasting Volatility00:42:21 How to Use Benchmarks Without Misusing Them00:43:50 Long-Ass Lightning Round: A Costly Modeling Mistake00:45:45 Advice to a Younger Finance Leader00:47:05 The Private Jet Accounting Story00:49:11 Credits#RunTheNumbersPodcast #FinanceLeadership #DealDesk #UsageBasedSaaS #AIinFinance This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ sits down with Bruno Annicq, CFO of Wellhub (formerly Gympass), to unpack a practical finance playbook built around cash discipline, sustainable growth, and simplicity. Bruno explains how he rebuilt forecasting using an AI-driven, probabilistic ensemble model, moving teams beyond single-scenario planning. They also dig into his EMPOWER planning framework, usable OKRs, and why tighter alignment between finance, HR, and wellbeing is becoming a durable lever for long-term performance.—SPONSORS:RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—LINKS:Bruno on LinkedIn: https://www.linkedin.com/in/bannicq/Wellhub: https://wellhub.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:“Run Toward a Tough Market” — Developing the Hard and Soft Skills To Be a Great Finance Leaderhttps://youtu.be/iNHbkcG7YEo—TIMESTAMPS:00:00:00 Preview and Intro00:02:19 Sponsors — RightRev, Rillet, Tabs00:06:43 Accidental CFO Origin Story00:07:34 Consulting to Operations Pivot00:08:12 Why Finance Clicked for Bruno00:09:28 McKinsey Prioritization in Real World00:10:02 Eisenhower Matrix and Prioritization00:11:08 Investing in Non-Urgent Work00:13:30 Lessons From AOL Reinvention00:16:10 Sponsors — Abacum, Brex, Metronome00:20:01 Career Growth Through Hard Problems00:20:52 Broadening Skills Through Change00:23:12 Five Core Finance Principles00:24:02 Cash Is King00:25:14 Driving Sustainable Growth00:26:01 No Surprises and Forecasting00:26:07 Finance as Business Enabler00:27:22 Less Is More Philosophy00:28:47 Hardest Principle: Less Is More00:29:46 Deterministic vs Probabilistic Forecasting00:31:11 Marketplace Volatility and Forecast Error00:32:10 Ensemble Models Explained00:33:37 Forecast Accuracy Gains00:34:53 Building Models In-House00:36:46 Why Explainability Matters00:37:48 Empower Framework Introduction00:47:47 Urgency, Compounding, Long-Term Thinking00:48:10 Advice to Younger Self00:50:06 Finance Stack and Expense Stories00:52:51 Credits#RunTheNumbersPodcast #CFO #FinanceLeadership #Forecasting #AIinFinance This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ sits down with Jason Kong, General Partner at Base10 Ventures, to unpack the firm's focus on “automation for the real economy” — software built for industries most tech investors overlook, but the world depends on. Jason breaks down what makes Series B investing uniquely hard, how he evaluates back-office and vertical SaaS opportunities, and where markets tip from niche to overcrowded. They also discuss Base10's decision to donate 50% of profits to fund scholarships, plus a lightning round spanning fantasy football, shorting SaaS in 2022, and a venture take that might spark debate.—SPONSORS:Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics—LINKS:Jason on LinkedIn: https://www.linkedin.com/in/jasonykong/Base10 Partners: https://base10.vc/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Scaling to $1B+ Revenue: From ServiceNow to Samsara | Dominic Phillipshttps://youtu.be/vBY6WZBMljw—TIMESTAMPS:00:00:00 Preview and Intro00:02:20 Sponsors — Metronome, RightRev, Rillet00:06:02 Base10 Background00:06:41 Automation for the Real Economy00:09:27 Vertical vs. Horizontal Software00:10:38 Cash Flow and Durability00:11:19 Product-Market Fit and ROI00:12:56 Growth Limits Selling to Tech00:13:19 The Size of the Real Economy00:14:16 Sponsors — Tabs, Abacum, Brex00:18:50 Base10's Giving Model00:20:30 Access, Education, and Tech00:21:53 Purpose and Founder Alignment00:22:51 Radical Transparency00:23:56 Portfolio Focus and Strategy00:24:05 Investing Ahead of Consensus00:26:29 ERP Adjacency as Alpha00:28:58 Lessons From Hedge Funds00:32:29 Public Markets Reality00:34:05 Public vs. Private Investing00:34:48 The Series B Sweet Spot00:36:49 A Bifurcated Series B Market00:38:56 Fast Series Bs and 2021 Vibes00:42:16 What Series B Looks Like Now00:44:36 Back Office Automation00:46:02 ERP-Centric Workflows00:48:33 Long-Ass Lightning Round00:49:36 Shorting SaaS in 202200:50:16 Fantasy Football and Investing00:52:57 Career Advice That Surprises00:55:03 A Contrarian Venture Take00:56:22 Credits#RunTheNumbersPodcast #SeriesB #RealEconomy #VerticalSaaS #BackOfficeAutomation This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ sits down with Dominic Phillips, CFO of Samsara, to unpack what it takes to scale a capital-intensive SaaS business from startup to public company in under a decade. Dominic reflects on his six-plus years at Samsara through hypergrowth, COVID disruption, supply chain constraints, a down-round survival raise, and an IPO at the very end of the 2021 tech window. Drawing on his earlier career at ServiceNow under Mike Scarpelli, he shares how experience across FP&A, IR, corp dev, and treasury shaped his approach to capital allocation, investor education, and analyst management. The conversation dives into asset-based pricing, selling into non-discretionary operations budgets, balancing hardware and software economics, and building credibility with a broad analyst base while scaling past $1B in ARR.—SPONSORS:Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai—LINKS:Dominic on LinkedIn: https://www.linkedin.com/in/dominicphillips/Company: https://www.samsara.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:“Steal Your Boss's Job”: Calendly CFO John McCauley on Leadership, Ownership & Growthhttps://youtu.be/VRpTNDIfzPYFrom SMB to Enterprise: The CFO Scaling Playbook With Andrew Casey | Mostly Classicshttps://youtu.be/kMuJ6gAuEpgDriving revenue without selling | Greg Henry of 1Passwordhttps://youtu.be/f5FsNoG8A3E—TIMESTAMPS:00:00:00 Preview & Intro00:02:40 Sponsors — Brex | Metronome | RightRev00:06:18 Interview Begins00:06:46 Dominic's Early Career00:08:47 From ServiceNow to CFO00:09:47 Joining Samsara00:10:54 COVID, Burn, and a Down Round00:12:40 IPO Messaging and Investor Education00:15:50 Sponsors — Rillet | Tabs | Abacum00:20:27 Hardware + Software Story00:21:29 What Samsara Does00:22:30 Data, AI, and ROI00:23:23 Horizontal Platform and Verticals00:24:27 Growth Drivers at Scale00:26:09 Selling Into Operations00:28:19 Change Management in Legacy Orgs00:29:46 Non-Discretionary Budgets00:33:02 Storytelling Lessons from Scarpelli00:36:14 Managing Analysts00:39:23 Earnings Timing Strategy00:41:06 Metrics and Investor Trust00:42:38 Investor Communication Channels00:44:22 Investor Days and Long-Term Vision00:45:37 Annual Planning Maturity00:48:24 Forecast Accuracy and Cadence00:49:28 The 1000-Day Strategy00:50:40 Top-Line and Margin Targets00:51:59 Capital Allocation by Function00:54:46 Becoming a CFO00:58:21 Lightning Round and a CFO Mistake01:02:41 End Credits#RunTheNumbersPodcast #CFO #ScalingCompanies #B2BSaaS #PublicMarkets This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ Gustafson sits down with Gordon Coyle, a 40-year commercial insurance veteran, to demystify one of the most anxiety-inducing topics for founders and CFOs: business insurance. Drawing on decades of experience with startups, scaleups, and regulated industries, Gordon breaks down what leaders need to know about D&O, E&O, cyber, and general liability, why investor pressure is rising, and where “cheap and easy” online policies fail when real risk hits. Through real-world examples, they explore how claims arise, how defense costs erode limits, why cyber insurance is as much about response as reimbursement, and how to balance budget, risk tolerance, and peer benchmarks—treating insurance as a critical layer of protection, not a box-checking exercise.—SPONSORS:Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run—LINKS:Gordon on LinkedIn: https://www.linkedin.com/in/gordoncoyle/The Coyle Group: https://thecoylegroup.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:The Coyle Group - Business Insurancehttps://www.youtube.com/@TheCoyleGroupNY—TIMESTAMPS:00:00:00 Preview and Intro00:01:53 Sponsors — Abacum | Brex | Metronome00:05:39 Interview Begins with Gordon Coyle00:06:23 Gordon Coyle & The Coyle Group00:07:21 Explaining Insurance on YouTube00:08:40 Turning Education into Inbound Leads00:09:40 Content as a Pull Strategy00:10:53 Insurance Complexity for Tech Founders00:13:28 Why Investors Require D&O Insurance00:14:09 What D&O Covers and Why It Matters00:15:50 Sponsors — RightRev | Rillet | Tabs00:20:19 Who D&O Covers and Rising Investor Pressure00:22:37 D&O Limits and Cost Tradeoffs00:23:21 Panic Calls and Late D&O Purchases00:24:39 How Defense Costs Erode Coverage00:25:31 Common D&O Claims and Employment Risk00:27:08 D&O vs E&O Explained00:29:12 Cyber Insurance and Social Engineering00:31:59 AI's Impact on Cyber Risk00:33:50 Real-World Ransomware Stories00:34:17 Cyber Insurance as Money and Response00:35:29 Business Email Compromise Scams00:39:43 Why Tech Still Needs General Liability00:41:16 What a BOP Covers00:42:32 Convenience vs Proper Coverage00:44:29 Surprising General Liability Claims00:46:45 Insurance Costs for Startups00:47:36 Higher Costs in High-Risk Industries00:48:26 Balancing Budget, Risk, and Coverage00:50:39 PEOs, Workers' Comp, and EPLI00:54:39 Choosing the Right Insurance Partner00:56:42 End Credits#RunTheNumbersPodcast #StartupFinance #BusinessInsurance #RiskManagement #CyberRisk This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

[Original air date: June 19, 2025]In this episode, Alex Immerman, partner at Andreessen Horowitz, joins CJ to discuss the CFO role and how it's changing in the era of AI. He explains what the components of a company's AI agenda the CFO should own, how and where it should be leveraged in an organization, and why, if you're preparing to go public, AI needs to be mentioned in your S-1. He breaks down how the financial landscape differs greatly between AI-native SaaS companies and traditional B2B SaaS companies in terms of retention curves and gross margins, and how this relates to the ever-important LTV to CAC metric. As someone who has worked with prominent CFOs and interviewed many for a16z's portfolio companies, Alex also describes the qualities of a great CFO, and shares his favorite interview question, before discussing CFOs, CEO, and board dynamics.—LINKS:Alex Immerman on LinkedIn: https://www.linkedin.com/in/immermanAndreessen Horowitz: https://a16z.comCJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:a16z's Alex Immerman on the Evolving Role of the CFO in the Age of AIhttps://youtu.be/JIvHp-mlnzsSo You're Looking for a “Strategic” CFO? Bloomerang's Steve Isom on What That Really Meanshttps://www.youtube.com/watch?v=cgHOtvG1Ces—TIMESTAMPS:00:00:00 Preview and Intro00:01:46 AI Margins Improve Dramatically00:02:29 What Separates Great CFOs00:03:29 Founder Mindset Drives Performance00:05:31 Founder Intensity and Margin Expansion00:06:57 Backing Unproven Bets Thoughtfully00:08:29 Interviewing CFOs for Backbone00:09:55 When CFOs Push Back on Strategy00:11:25 CFO Trust With Boards and Investors00:11:50 How CFOs Engage Investors When Hiring00:14:44 Building Strong CFO Investor Relationships00:16:18 Sharing Bad News Early00:17:21 CEO Vision Versus CFO Validation00:20:57 How AI Is Changing the CFO Role00:23:56 Incumbents Versus AI-Native Finance Tools00:26:24 CFOs Driving Internal AI Adoption00:28:07 AI Impact on Customer Support Efficiency00:29:26 Internal Leverage From AI Automation00:31:29 Why Investors Care About LTV to CAC00:34:00 LTV to CAC Across Business Models00:36:26 Retention Curves Matter More Than Growth00:38:16 Evaluating AI Gross Margins Long Term00:40:04 Recipe for AI Margin Expansion00:43:01 What Makes a Public-Ready CFO00:44:47 Beating Guidance Drives IPO Performance00:46:56 Growth Versus Profitability Has Rebalanced#RunTheNumbersPodcast #CFOLeadership #FintechInvesting #AISaaS #VentureCapital This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

[Original air date: May 8, 2025]When it comes to investor relations, an organization's communication strategy should be a key instrument to support its business strategy. While this may seem obvious, so often we get this wrong. In this episode, CJ hosts a masterclass on investor relations with Samuel Levenson of the Arbor Advisory Group and Jon Neitzell of Andruil Partners, focusing on the strategic role of IR in driving company valuation. They cover what “audience opportunity” really means and what to do when you've attracted the wrong investors. They talk about metrics, KPIs, and OKRs, plus why management credibility and conveying conviction can make or break your IR strategy. They also discuss what has changed in the IR profession over time and what hasn't (but probably should) before suggesting changes you can make to drive impact immediately.—LINKS:Samuel Levenson on LinkedIn: www.linkedin.com/in/samlevenson/Jon Neitzell on LinkedIn: www.linkedin.com/in/jonathan-neitzell/Arbor Advisory Group: www.arboradvisorygroup.com/Anduril Partners: https://www.andurilpartners.ai/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Investor Relations as a Strategic Weapon: A Masterclasshttps://youtu.be/ac9xmURhAqE—TIMESTAMPS:00:00:00 Preview and Intro00:02:22 Welcome to Sam and Jon00:03:12 Linking Business Strategy and Communication00:05:01 Proactive vs. Reactive Investor Relations00:06:39 Tailoring the Message by Investor Type00:08:05 Audience Opportunity and Ideal Shareholders00:11:05 When the Investor Base No Longer Fits00:12:21 Shifting Investors as Industries Change00:13:16 Optionality Comes From Patient Shareholders00:14:40 Conveying Conviction Through Credibility00:17:03 Why Investor Days Build Trust00:18:02 Metrics Versus Storytelling in IR00:19:10 Choosing Metrics the Market Actually Rewards00:22:30 Valuation Disconnects and Investor Confusion00:23:17 Finding Metrics That Truly Drive Value00:25:33 Avoiding Bad Capital Allocation Decisions00:26:20 Disclose Versus Guide: Confidence Intervals00:27:35 Knowing What You Don't Know00:29:33 Science Versus Art in Storytelling00:33:11 When Algorithms Become Your Audience00:33:56 Passive Investing Now Dominates Markets00:35:16 Linking OKRs to Value-Driving KPIs00:36:42 Closing the Strategy-Metrics Feedback Loop00:38:07 When Investors Sense Operational Confidence00:39:47 Why IR Becomes Strategy Consulting00:41:28 Why IR Teams Stay Undersized00:43:23 Sam's Accidental Entry Into Investor Relations00:44:34 Mentorship Over Formal IR Training00:46:18 How Markets Outpaced IR Practices00:47:01 Investor Days Go Virtual00:49:34 Designing a High-Quality Earnings Call00:50:41 Investor Days as High-ROI Investments00:51:45 IR Websites as Investor Onramps00:53:42 World-Class Investor Day Examples00:54:20 Using AI to Prepare Investor Communications00:56:19 Building a Proactive IR 2.0 Strategy00:58:33 Why IR Requires Full Executive Buy-In01:00:51 Data Transfers Conviction to Investors01:03:31 Closing Reflections on Trust and Valuation#RunTheNumbersPodcast #InvestorRelations #CapitalMarkets #ValuationStrategy #CFOInsights This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Mostly Growth on YouTube: https://www.youtube.com/@MostlyGrowthMostly Growth on Apple: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102Mostly Growth on Spotify: https://open.spotify.com/show/3KDtaLaXx1obFp5PUhZ6V3In this year-end episode of Mostly Growth, CJ Gustafson, Kyle Poyar, and Ben Hillman reflect on what it actually takes to build a modern media business around newsletters and podcasts. They unpack CJ's first year going full-time, comparing creative intuition versus metric-driven operating styles, and discuss what content truly drives growth. The conversation also covers distribution dynamics, the emotional reality of unsubscribes and burnout, and closes with a candid look at monetization, team building, and the tradeoffs between simplicity and scale.—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—LINKS:Mostly Metrics: https://www.mostlymetrics.comCJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Growth Unhinged: https://www.growthunhinged.com/Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/Slacker Stuff: https://www.slackerstuff.com/Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/https://www.growthunhinged.com/p/deep-research-for-gtmhttps://www.growthunhinged.com/p/2025-state-of-b2b-gtm-reporthttps://www.mostlymetrics.com/p/presenting-the-state-of-the-agentic-financial-stackhttps://www.mostlymetrics.com/p/the-great-ai-arr-illusionhttps://www.mostlymetrics.com/p/presenting-the-2025-tech-stack-reporthttps://www.mostlymetrics.com/p/download-the-annual-planning-biblehttps://www.growthunhinged.com/p/how-to-sell-annual-planshttps://www.growthunhinged.com/p/get-recommended-by-chatgpthttps://www.growthunhinged.com/p/gtm-vibecoding-ideashttps://www.growthunhinged.com/p/how-to-use-ai-agents-for-marketing—RELATED EPISODES:We get roasted for swag and drop some GTM goldhttps://youtu.be/uubf_8al95wDo vanity plates bring serious business?https://youtu.be/Cm1rubFb-kgPricing in the Real World: Babies, Bots, and Billinghttps://youtu.be/T1cjFSZR0k0—TIMESTAMPS:00:00:00 Preview and Intro00:01:52 Sponsors — Pulley | Metronome00:04:12 Action Figure Swag and Year-in-Review Setup00:05:47 Going Full-Time and the First-Year Reality Check00:07:24 Writing Schedules, Creative Work, and Time Optimization00:09:16 Writing Speed, Craft, and the Myth That Time Equals Quality00:10:51 Perfectionism vs. Throughput in Newsletter Writing00:13:03 Creator Burnout, Motivation, and Engagement Anxiety00:14:08 Playing the Long Game vs. Obsessing Over Metrics00:15:42 Best Work of the Year and High-Leverage Content Bets00:17:55 Big Research Reports as Career-Defining Projects00:19:19 When Memes Outperform Deep Work00:19:52 LinkedIn Algorithms vs. Content Quality00:20:51 Writing for the Feed vs. Writing to Think00:22:03 Optimizing LinkedIn Profiles for Credibility00:23:47 Subscriber Growth, Audience Quality, and Churn Reality00:27:20 Reports and Research as Growth Engines00:28:37 Tactical “How-To” Content That Actually Converts00:30:21 Tactical Value Beats Sounding Smart00:30:40 Building a Team and Scaling Beyond a Solopreneur00:32:05 Simplicity vs. Scale in Early Business Decisions00:35:37 Avoiding Boredom and Shiny Object Syndrome00:37:12 Balancing Writing, Consulting, and Energy00:37:54 Making the Leap Financially as a Creator00:39:01 Subscriptions vs. Advertising as the Real Business Model#MostlyGrowthPodcast #CreatorEconomy #IndependentCreator #NewsletterBusiness #YearInReview This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

[Original air date: June 5, 2025]How can finance leaders identify where their capital is silently going to waste and where it can be better used to drive growth? In this episode, CJ interviews Russell Lester, the CFO of Tropic, where capital allocation is both the product and the mission. Russell introduces the concept of “spoilage”, deployed capital that fails to deliver its intended value. He also talks about “levers”, positive actions that force multiply your efforts, and “leakages”, headwinds or detractors that sap momentum. Russell believes it is the job of the CFO (or “Chief Alignment Officer”) to proactively go looking for these levers and leakages. He then explains how he uses his “center of the table” framework to redeploy the freed-up capital to fuel growth. Russell also covers how to address misalignment, what helicopter skills are and why you need them, what a data safari is and why you should take one daily, and why every CFO needs a spend management tool.—SPONSORS:Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Sage Intacct is a cloud financial management platform that replaces spreadsheets, automates workflows, and keeps your books audit-ready as you scale. It unifies accounting, ERP, and real-time reporting for finance, retail, logistics, tech, and professional services. With payback in under six months and up to 250% ROI, and eight years as the customer-satisfaction leader, Sage Intacct helps you take control of your growth: https://bit.ly/3Kn4YHtMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.—LINKS:Russell on LinkedIn: https://www.linkedin.com/in/russell-lester-aa98463/Tropic: https://www.tropicapp.io/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Wasted Capital and Where to Find It The CFOs Guide to Spoilage Levers Leakageshttps://youtu.be/xOby7CcdljI—TIMESTAMPS:00:00:00 Mostly Classics: Russell Lester on Capital and Alignment00:00:48 Sponsors — Tipalti | Aleph | Fidelity Private Shares00:04:07 Russell Lester Joins the Show00:06:45 Capital Spoilage and Wasted Spend00:08:34 Why Spoilage Goes Unnoticed Inside Companies00:10:16 Creating Accountability for ROI00:11:08 Spoilage Beyond Tools and Software00:13:04 Strategy Drift and the Sunk Cost Trap00:14:14 Sponsors — Sage Intacct | Mercury | RightRev00:17:44 Levers and Leakages: A Framework for Momentum00:19:27 Identifying Levers Across the Funnel00:21:48 Efficiency Levers Inside the P&L00:23:31 Common Spend Leakages in Practice00:24:21 The Center of the Table Framework00:26:47 Budget Ownership vs Corporate Stewardship00:28:49 The CFO as Chief Alignment Officer00:31:31 Trust, Tact, and Executive Leadership00:33:35 Helicopter Skills for Finance Leaders00:35:41 Curiosity as a CFO Superpower00:36:02 Data Safaris and Asking Better Questions00:38:16 Breaking Down Net Dollar Retention00:40:32 Navigating Data Overload00:42:16 Building a Single Source of Truth00:43:03 Intelligent Spend Management in Action00:44:44 Capital Allocation as the CFO's Core Job00:46:04 How Spend Management Drives Growth00:49:14 Why Companies Delay Spend Tools00:50:49 A Career Mistake with Investors00:52:49 Auto-Renewals: Revenue vs Leakage00:54:07 Advice to a Younger CFO#RunTheNumbersPodcast #CFOLeadership #CapitalAllocation #FinancialStrategy #SpendManagement This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this special, table-turning episode of Run the Numbers, CJ Gustafson steps out of the host's chair as Paul Stansik—Operating Partner at ParkerGale and author of the Hello Operator newsletter—takes over the interview. What began as a planned discussion on annual planning best practices quickly evolves into a candid deep dive on Mostly Media, CJ's growing niche B2B media business, and the thinking behind his own operating plan for the year ahead. Fresh off exiting his CFO role in January 2025, CJ walks through the origin story of Mostly Metrics, how it scaled into a broader media platform, and what it's like being “the boss of me” for the first time. Paul presses on the real questions—growth opportunities, monetization, and strategic tradeoffs—making this episode a transparent look at how a modern, metrics-driven media business is built and run.—SPONSORS:RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Sage Intacct is a cloud financial management platform that replaces spreadsheets, automates workflows, and keeps your books audit-ready as you scale. It unifies accounting, ERP, and real-time reporting for finance, retail, logistics, tech, and professional services. With payback in under six months and up to 250% ROI, and eight years as the customer-satisfaction leader, Sage Intacct helps you take control of your growth: https://bit.ly/3Kn4YHtMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.com—LINKS:Paul on LinkedIn: https://www.linkedin.com/in/paulstansik/Hello Operator: https://hellooperator.substack.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Portfolio Operations: This Is What You Actually Have To Do To Make Sure a Company Is Successfulhttps://youtu.be/pOj4JwGUTSoGrindr's $0 CAC Secret from the CFO Who Launched Disney+ | Vanna Krantzhttps://youtu.be/ijFIMmtpLNw—TIMESTAMPS:00:00:00 Preview and Intro00:02:10 Sponsors — RightRev | Tipalti | Aleph00:06:23 Episode Setup and Context00:07:22 Why This Episode Exists00:08:44 The Origin Story00:10:03 First Signs of Traction00:10:26 Memes, Early Growth, and “Big Ballers”00:12:01 Defining the Brand Feel00:13:28 Leaving a Job to Write00:15:07 Writing His Way to CFO00:16:26 Sponsors — Fidelity Private Shares | Sage Intacct | Mercury00:19:01 Growth Tactics That Worked00:21:31 First Monetization Moment00:22:13 Balancing CFO Life and Media00:24:06 Going All-In on the Business00:25:02 A CFO Lens on Media00:28:09 Asset Businesses vs Cash Flow00:31:35 How the Business Makes Money00:32:42 Revenue Compounding Over Time00:33:29 Scaling to $3M00:34:08 Partnerships and Buying Cycles00:36:19 Building the Core Team00:39:09 Adding Recruiting to the Mix00:41:01 Strategy for the Next Phase00:42:03 Boredom, Discipline, and Craft00:43:08 Defining the Core Audience00:46:09 Staying in the Game00:47:22 Advice for Creators00:49:15 Brand, Fun, and Value00:52:08 Following the Momentum00:53:14 Finding Your Unique Edge00:55:19 Enjoying the Build00:56:25 Closing and Outro#RunTheNumbersPodcast #creatoreconomy #mediabusiness #cfoperspective #buildinpublic This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Mostly Growth on YouTube: https://www.youtube.com/@MostlyGrowthMostly Growth on Apple: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102Mostly Growth on Spotify: https://open.spotify.com/show/3KDtaLaXx1obFp5PUhZ6V3In this episode of Mostly Growth, CJ Gustafson, Kyle Poyar, and Ben Hillman unpack a wide-ranging set of predictions and observations about where go-to-market strategy, AI, and pricing models are headed next. They discuss why what ChatGPT says about your product may become a core marketing KPI, the resurgence of direct mail and physical touchpoints in an AI-saturated world, and why “almost as good as a human” is a dangerous positioning for AI-driven products. The conversation also explores AI monetization paths through advertising, the risk of an AI infrastructure timing mismatch leading to a broader financial pullback, and what historical parallels like railroads and the Sears catalog can teach us about today's buildout. The episode closes with real-world pricing lessons, from energy-as-a-service solar subscriptions to the surprisingly massive standalone economics of Apple's AirPods, tying together how distribution, perception, and monetization shape durable growth.—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—LINKS:Mostly Metrics: https://www.mostlymetrics.comCJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Growth Unhinged: https://www.growthunhinged.com/Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/Slacker Stuff: https://www.slackerstuff.com/Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/—RELATED EPISODES:996 Culture, Exploding AI Bills & SaaS Chaoshttps://youtu.be/qhrxDL0gsRoThe Layer-Cake Playbook for Vertical SaaS Growth | with Roland Ligtenberghttps://youtu.be/yPxWvhPISKoOpenAI's Impossible Math: $500B or Bust?https://youtu.be/L6PLnvjcnpkFrom Birding Apps to Billion-Dollar Bundles: The Future of SaaS Growthhttps://youtu.be/mzITrIP70OkWhere Did All the Middle Managers Go?https://youtu.be/LvN7RzmApPU—TIMESTAMPS:00:00:00 Preview and Intro00:01:40 Sponsors — Pulley, Metronome00:04:00 Welcome Back And Consumer Friction00:05:29 Insurance Middlemen Frustrations00:07:07 Explaining Newsletter Businesses00:07:58 Family Perceptions Of Work00:09:05 GTM And Growth Predictions00:10:19 Trust And Objectivity In ChatGPT00:12:01 ChatGPT As Marketing KPI00:14:14 Direct Mail Marketing Comeback00:15:56 Tech Buying Media Assets00:17:52 Fake Subscribers And Email Lore00:19:03 AI Quality Over Automation00:22:11 AI Healthcare And Ad Models00:24:40 Advertising Fuels AI Economics00:25:40 AI Boom Versus Bust Timing00:27:49 Infrastructure Before Killer Apps00:30:21 Railroad Economics And Real Estate00:30:46 Solar Subscriptions And Pricing00:32:50 AirPods As Recurring Revenue00:34:57 Show Outro And Credits#MostlyGrowthPodcast #GrowthMarketing #AITrends #GoToMarket #StartupStrategy This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ Gustafson sits down with Larry Contrella, General Partner at JMI Equity, to unpack how JMI invests in software without financial engineering or roll-up strategies. Larry explains how the firm builds conviction through founder relationships, long-term partnership, and a product-and-brand-first view of durable growth. They discuss how JMI supports companies through scaling, why operating partners keep returning, and how underwriting looks different in mission-driven sectors like K–12 and nonprofit tech where customers are schools and communities, not Fortune 500s. Larry's background as a competitive runner at Penn ties the conversation together with a clear ethos: patience, discipline, and playing the long game.—SPONSORS:Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Sage Intacct is a cloud financial management platform that replaces spreadsheets, automates workflows, and keeps your books audit-ready as you scale. It unifies accounting, ERP, and real-time reporting for finance, retail, logistics, tech, and professional services. With payback in under six months and up to 250% ROI, and eight years as the customer-satisfaction leader, Sage Intacct helps you take control of your growth: https://bit.ly/3Kn4YHt—LINKS:Larry on LinkedIn: https://www.linkedin.com/in/larry-contrella-160a8a25/JMI Equity: https://www.jmi.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Is taking a company public even worth it? | Fullstory's Chad Goldhttps://youtu.be/zSD8y9dr4VgSo You're Looking for a “Strategic” CFO? Bloomerang's Steve Isom on What That Really Meanshttps://youtu.be/cgHOtvG1Ces—TIMESTAMPS:00:00:00 Preview and Intro00:02:49 Sponsors — Mercury | RightRev | Tipalti00:06:41 Joining the JMI Conversation00:07:13 College Running and Team Dynamics00:08:13 New York Marathon Story and Career Intersection00:11:04 Competitive Drive and Patience With Founders00:12:54 Building Long-Term Partnerships and Underwriting Credibility00:15:27 Growth Equity as a Long Sales Cycle00:15:48 Sponsors — Aleph | Fidelity Private Shares | Sage Intacct00:18:44 Fund Planning, Deal Pacing, and Board Commitments00:20:59 Sourcing Philosophy and Developing Investors Over Time00:22:09 Hustle as the Only Sustainable Edge in Sourcing00:24:14 Early Sourcing Tactics and Information Arbitrage00:26:06 Reputation, Experience, and Breaking Into Competitive Deals00:29:42 Organic Growth Over Roll-Ups and M&A Discipline00:32:51 Brand, Product Leadership, and Paying for the Best Businesses00:33:29 Bloomerang and Brand-Led Growth in Nonprofit Software00:34:46 Why JMI Operators Keep Coming Back00:36:28 Collaborative Leadership and Giving Constructive Advice00:38:20 Using Data Without Slowing Decisions00:39:20 Transparency, Alignment, and Knowing Where You Stand00:40:31 Why JMI Invests in K–12 and EdTech00:42:07 Mission-Driven Businesses and Talent Advantage00:43:24 Monetization Models in Nonprofit SaaS00:45:40 Conviction Bets and Product-Market Fit Stories00:48:49 Rethinking TAM and Expanding Markets Over Time00:50:40 Lightning Round: Sourcing Stories and Lessons00:52:58 Traits of Great Founders and Changing Beliefs00:54:20 Closing Thoughts and Outro#RunTheNumbersPodcast #GrowthEquity #B2BSoftware #FounderRelationships #PrivateEquity This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ Gustafson sits down with Brian Brown, Chief Financial Officer and Treasurer at Rocket Companies, to unpack how Rocket has built a differentiated, full-stack fintech business far beyond its mortgage roots. The conversation explores Rocket's approach to long-tail monetization, the strategic importance of mortgage servicing, and how recapture rates become a durable competitive advantage in volatile rate environments. Brian shares lessons from leading complex M&A transactions, managing a business that reacts in real time to macro signals, and building a finance organization that prioritizes storytelling, strategy, and cross-functional thinking over pure accounting prowess. The result is a wide-ranging discussion on what traditional financial services companies can teach modern SaaS and fintech leaders about metrics, brand, and disciplined execution.—SPONSORS:Sage Intacct is a cloud financial management platform that replaces spreadsheets, automates workflows, and keeps your books audit-ready as you scale. It unifies accounting, ERP, and real-time reporting for finance, retail, logistics, tech, and professional services. With payback in under six months and up to 250% ROI, and eight years as the customer-satisfaction leader, Sage Intacct helps you take control of your growth: https://bit.ly/3Kn4YHtMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.—LINKS:Brian on LinkedIn: https://www.linkedin.com/in/brian-brown-3aa37a8a/Rocket Companies: https://rocket.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:From $500M Losses to $500M Profits: The CFO Who Helped Major League Baseball Win off the Fieldhttps://youtu.be/7xw9qY2w5C4—TIMESTAMPS:00:00:00 Preview and Intro00:02:30 Sponsors — Sage Intacct | Mercury | RightRev00:05:55 CJ's Rocket Mortgage Fanboy Moment00:07:13 How Rocket Mortgage Actually Makes Money00:12:06 Investing in Brand Trust for Infrequent but High-Stakes Decisions00:15:17 Mortgage Servicing as a Long-Term Relationship Engine00:17:17 Sponsors — Tipalti | Aleph | Fidelity Private Shares00:20:40 Why the Long Tail of Customer Relationships Is Underrated00:23:01 Recapture Rate and Why Mortgage Loyalty Is Broken00:25:23 Lower CAC Through Lifetime Value and Repeat Borrowers00:30:55 Financial Storytelling as a CFO's Real Job00:33:03 Why CFOs Must Sell the Story, Not Just the Numbers00:40:49 Public vs. Private M&A and Why Public Deals Are Harder00:45:21 Redfin Acquisition Thesis and Top-of-Funnel Strategy00:52:18 Being Swarmed by Merger Arb Funds Like Taylor Swift00:55:18 How Rocket Forecasts in a Volatile Interest Rate Environment00:58:04 Weekly Forecasting, Scenario Planning, and Avoiding Forecast Fatigue01:00:32 Finance Teams as Business Consultants and Strategic Partners01:02:23 Why CFOs Need a Seat at the Strategy Table01:04:19 Long-Ass Lightning Round: A Leadership Mistake and Building Teams01:05:58 Leadership Lessons on Team Size and Accountability01:07:33 Advice to Younger Self and Slowing Down01:08:49 Finance Software Stack and AI Tools01:11:31 Lessons from Working with Dan Gilbert01:16:58 Craziest Expense Story01:17:55 Outro#RunTheNumbersPodcast #CFOLeadership #FinanceStrategy #MergersAndAcquisitions #FinancialStorytelling This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Mostly Growth on YouTube: https://www.youtube.com/@MostlyGrowthMostly Growth on Apple: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102Mostly Growth on Spotify: https://open.spotify.com/show/3KDtaLaXx1obFp5PUhZ6V3In this episode of Mostly Growth, CJ Gustafson and Kyle Poyar explore the hidden mechanics behind focus, competition, and value creation across both consumer culture and B2B SaaS. They unpack why point-solution companies like Untuckit and Raising Cane's can outperform diversified rivals, examine how competition actually strengthens category demand, and break down the gray zone of mid-market venture exits where founder incentives and investor expectations diverge. The conversation ranges from private equity roll-ups to the realities of cold-calling returning as a top-performing growth channel, to pricing transparency, algorithmic price discrimination, and how everyday behaviors—from mall Santas to $12 club water—reflect deeper strategic forces. It's a fast, practical look at how operators can stay focused, understand market pressure, and avoid chasing the wrong game.—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—LINKS:Mostly Metrics: https://www.mostlymetrics.comCJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Growth Unhinged: https://www.growthunhinged.com/Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/Slacker Stuff: https://www.slackerstuff.com/Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/—RELATED EPISODES:Building AI-Native Software With No Rules | Christopher O'Donnellhttps://youtu.be/Fr1027kZyC0SaaS Founder or Pop Star? CJ Gets Schooledhttps://youtu.be/LMZq_DwVmkYThe Layer-Cake Playbook for Vertical SaaS Growth | with Roland Ligtenberghttps://youtu.be/yPxWvhPISKoThe One Use Case for Venture Debt That Most Founders Never Think Abouthttps://youtu.be/XxH_Y9OH_i0—TIMESTAMPS:00:00:00 Preview and Intro00:01:42 Sponsors – Pulley | Metronome00:04:02 Mall Fashion & Nostalgia00:05:50 The Modern Mall Santa Reinvented00:06:52 Untuckit & the Platform vs. Point Solution Debate00:08:31 The Power of Category Focus00:09:56 Obsession, Craft, and the Raising Cane's Lesson00:10:46 Germany's “Hidden Champions”00:12:44 Competition: When to Care and When Not To00:14:05 OpenAI, Gemini & the “Code Red” Mindset00:15:34 Competition to Category Education00:17:00 Pricing Pages as Competitive Battlegrounds00:18:05 VC Deck Theater & Competitive Grids00:18:54 Rise of B2B Newsletter Advertising00:19:48 Awkward Exits: The Venture “Gray Zone”00:21:46 Founder Life-Changing Exits vs. VC Math00:23:04 Why Secondaries Exist (and When They Help)00:24:58 Why $100–500M Is the Most Common SaaS Exit Range00:26:14 Structural Misalignment in Venture Exits00:27:20 How Much Secondary Is Too Much?00:30:25 Business Blunders: Justin Bieber the PM00:31:54 Voice Notes, Etiquette, and Chaos00:33:23 Cold Calling Makes a Comeback00:35:50 Catherine Jhung Still Cold Calls CFOs00:37:44 Algorithm Pricing Labels & Data-Driven Pricing00:41:11 Why Clubs Charge $12 for Water00:42:40 Closing Credits#MostlyGrowthPodcast #keepitsimple #focuswins #businessstrategy #operatorsmindset This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Blake Grayson, CFO of Docusign, joins CJ Gustafson to discuss how a company that redefined e-signature and became a verb is now navigating its next chapter in intelligent agreement management. Drawing on more than a decade at Amazon—where he helped forecast AWS and worked inside some of the company's most operationally demanding businesses—Blake explains how financial discipline, operational depth, and clear narrative-building shape his approach as CFO. The conversation explores how to evolve a beloved product without diluting the brand, why pricing is as much about positioning as revenue, how to communicate go-to-market mechanics without losing the room, and why effective capital allocation accepts that not every big bet needs to land to shape the leader you become.—SPONSORS:Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Sage Intacct is a cloud financial management platform that replaces spreadsheets, automates workflows, and keeps your books audit-ready as you scale. It unifies accounting, ERP, and real-time reporting for finance, retail, logistics, tech, and professional services. With payback in under six months and up to 250% ROI, and eight years as the customer-satisfaction leader, Sage Intacct helps you take control of your growth: https://bit.ly/3Kn4YHtMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run—LINKS:Blake on LinkedIn: https://www.linkedin.com/in/blake-grayson-3197043/Docusign: https://www.docusign.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:“Steal Your Boss's Job”: Calendly CFO John McCauley on Leadership, Ownership & Growthhttps://youtu.be/VRpTNDIfzPY—TIMESTAMPS:00:00:00 Preview and Intro00:02:39 Sponsors – Fidelity Private Shares | Sage Intacct | Mercury00:05:09 DocuSign as a Top CFO Tool00:07:33 From E-Signature to Intelligent Agreement Management00:09:09 Complexity Before and After a Signature00:11:02 Cost of Poor Agreement Management00:12:30 Agreement Oversight and CFO Risk00:13:28 Pricing: Usage to Seat Models00:14:12 Enterprise vs SMB Pricing00:15:00 Sponsors – RightRev | Tipalti | Aleph00:19:18 Simplicity, Tiers, and IAM Value00:20:36 Forecasting New Products in a Renewals Base00:22:13 Modeling Mix Shift and GTM Enablement00:23:56 Faster Time-to-Value With Intelligent Repositories00:25:06 Building GTM Muscle for a Platform00:26:29 Launching IAM in Commercial First00:27:31 Forecasting Growth vs Cost00:28:41 Company-Wide Alignment on Priorities00:30:02 Aligning Investor Messaging With Operations00:31:20 Staying Focused on Long-Term Outcomes00:32:27 Customer-First Decision Making00:33:41 Transparency and What Not to Disclose00:34:52 Asking Better Metric Questions00:36:28 Avoiding Data Paralysis00:38:52 Amazon's Weekly Business Reviews00:41:07 Bezos Meetings and the Silent Read00:45:09 The “Question Mark Email” and Customer Anecdotes00:50:22 Unit Economics of a Server and Early AWS Bets00:53:42 Handling Nonpayment Risk00:55:07 Operational Chaos: Perishables and Regulation00:57:04 The “No Eggs in California” Story00:59:31 Treating Escalations as Company Problems01:00:59 Biggest Career Mistake01:02:44 Advice to His Younger Self01:06:34 Tools Finance Uses: Oracle, Bots, IAM, Salesforce, Workday01:09:21 Wildest Expense Attempts01:12:32 Closing Thanks and Credits#RunTheNumbersPodcast #Docusign #CFOInsights #SaaSLeadership #AIManagement This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Cassie Young brings hard earned lessons from a career spanning CRO roles, customer success leadership, turnarounds, and now investing as a General Partner at Primary Venture Partners. She talks about building and rebuilding go to market teams, why sometimes you should fire customers on purpose, and how churn is a lagging indicator that hides deeper retention issues. Cassie shares strong views on overrated metrics like NPS, the incentives that actually drive behavior inside a business, and the myth of finding one perfect KPI. She also brings signature Cassie isms like sunlight is the best disinfectant and the reminder that leaders often get stuck working in the business instead of on it offering practical insights for anyone trying to keep their SaaS metrics from going sideways.—SPONSORS:Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Sage Intacct is the cloud financial management platform that replaces spreadsheets, eliminates manual work, and keeps your books audit-ready—so you can scale without slowing down. It combines accounting, ERP, and real-time reporting for retail, financial services, logistics, tech, professional services, and more. Sage Intacct delivers fast ROI, with payback in under six months and up to 250% return. Rated #1 in customer satisfaction for eight straight years. Visit Sage Intacct and take control of your growth: https://bit.ly/3Kn4YHtMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.—LINKS:Cassie on LinkedIn: https://www.linkedin.com/in/cassyoung/Primary Venture Partners: https://www.primary.vc/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Getting fired 4 times made me a founder | Sam Jacobs of Pavilionhttps://youtu.be/8X-JVOF-1A0—TIMESTAMPS:00:00:00 Preview and Intro00:02:30 Sponsors Aleph | Fidelity Private Shares | Sage Intacct00:05:21 Returning From Pavilion & GTM Summit Takeaways00:06:49 What Makes a Great Executive00:11:07 The Importance of True P&L Fluency00:12:17 First Team Leadership vs Functional Loyalty00:13:33 Reading the Macro Environment and Market Forces00:14:29 Sponsors Mercury | RightRev | Tipalti00:18:26 Applying First Team Leadership in Practice00:22:24 Churn as a Lagging Indicator00:24:23 Finding Real Leading Indicators of Renewal00:25:30 Customer Value as the Only Path to Enterprise Value00:26:52 Product Adoption Perception and Retention00:29:16 Price to Value Ratio as a Predictor of Guaranteed Churn00:30:37 The Ultimate Question What Gets Your Customer Promoted00:32:33 How NPS Is Actually Calculated00:34:56 Sailthru's Minus 26 NPS and What It Signaled00:37:31 Rebuilding Customer Trust Through Transparency00:40:24 Why Net and Gross Retention Must Be Paired00:42:51 Aligning the Executive Team Through a Unified Bonus Plan00:45:18 Firing Customers When Misaligned Segments Drain the Org00:49:35 Carrot vs Stick How to Motivate a Modern GTM Org00:52:31 Why MBO Plans Fail CSMs01:03:51 Why Time to Value Matters More Than Ever#RunTheNumbersPodcast #CustomerSuccess #ChurnPrevention #GoToMarket #VentureCapital This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Mostly Growth on YouTube: https://www.youtube.com/@MostlyGrowthMostly Growth on Apple: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102Mostly Growth on Spotify: https://open.spotify.com/show/3KDtaLaXx1obFp5PUhZ6V3In this episode of Mostly Growth, CJ Gustafson and Kyle Poyar bounce between sharp SaaS insights and delightfully weird internet culture. They start with an unexpected dive into competitive bird-watching apps, then break down recent software mergers like Superhuman + Grammarly + Coda and what they signal about scaling, cross-sell strategy, and private equity mechanics. CJ and Kyle explore why PE portfolios are becoming powerful distribution channels for AI solutions, how niche data “signals” are outpacing generic ones in sales, and share hedge-fund-style tactics for uncovering proprietary business information. The conversation rounds out with “business blunders” — from Y-axis chart crimes to clickbait headlines — and a lively discussion on Spotify's pricing power and how companies should (and absolutely should not) communicate price increases.—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—LINKS:Mostly Metrics: https://www.mostlymetrics.comCJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Growth Unhinged: https://www.growthunhinged.com/Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/Slacker Stuff: https://www.slackerstuff.com/Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/—RELATED EPISODES:The Layer-Cake Playbook for Vertical SaaS Growth | with Roland Ligtenberghttps://youtu.be/yPxWvhPISKo—TIMESTAMPS:00:00:00 Preview and Intro00:01:43 Sponsors – Pulley and Metronome00:04:05 Birding, Big Year & AI Bird Apps00:06:42 Software M&A Trends in SaaS00:08:57 Superhuman–Grammarly–Coda Reverse Merger00:10:34 How Larger Valuations Attract a New Investor Class00:11:55 Streaming Wars & Platform Consolidation00:13:20 Private Equity as a Distribution Channel for AI00:14:48 How PE Firms Drive Multi-Company Expansion00:15:56 AI for Efficiency: The PE CFO Playbook00:17:44 When AI ROI Really Matters in PE00:19:23 Signal-Based Selling: High-Intent Buyer Detection00:21:15 Signal Fatigue & the Hunt for Better Data00:22:50 Why Proprietary Signals Win00:24:05 Creative (and Creepy) Data Tactics00:26:09 Pinterest vs. Google: Aspirational vs. Actual Behavior00:27:17 Blurring Work & Personal Signals in AI Tools00:27:46 The Michael Jordan of Y-Axis Crimes00:30:33 Notion Agents Billboard: “Let Them Cook”00:32:31 Pricing in the Real World: Spotify00:34:60 → 00:35:00 How to Communicate a Price Increase00:35:40 Closing Credits#MostlyGrowthPodcast #PricingStrategy #AIGrowth #GoToMarket #PrivateEquity This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

CoreWeave CFO Nitin Agrawal joins Run the Numbers to unpack the finance engine behind one of the fastest-growing AI infrastructure companies on the planet. CJ and Nitin dive into what it takes to build financial discipline in an environment where business models are being invented in real time, discussing the company's 700% growth last year and massive first-quarter performance as a newly public company. They cover capex strategy, securitizing GPUs, managing billion-dollar revenue backlogs, and structuring incentives for hyperscale deals, all while keeping investors grounded and servers running at full tilt. If you want a front-row seat to finance in the AI arms race, this episode delivers.—SPONSORS:Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Sage Intacct is the cloud financial management platform that replaces spreadsheets, eliminates manual work, and keeps your books audit-ready—so you can scale without slowing down. It combines accounting, ERP, and real-time reporting for retail, financial services, logistics, tech, professional services, and more. Sage Intacct delivers fast ROI, with payback in under six months and up to 250% return. Rated #1 in customer satisfaction for eight straight years. Visit Sage Intacct and take control of your growth: https://bit.ly/3Kn4YHtMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.—LINKS:Nitin on LinkedIn: https://www.linkedin.com/in/nitin-agrawal-cloudcfo/Company: https://www.coreweave.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:The Art and Science of a Day-One IPO Pop with OneStream Software CFO Bill Koefoedhttps://youtu.be/kYCn7XNkCBcFrom Facebook's Hypergrowth to Daffy's Disruption: A CFO's Playbook for Saying Yeshttps://youtu.be/bRIZ6oNPGD0—TIMESTAMPS:00:00:00 Preview and Intro00:02:54 Sponsors – Tipalti | Aleph | Fidelity Private Shares00:06:12 Interview Begins: Scaling CoreWeave00:06:52 CoreWeave's Pivot From Crypto to AI00:11:41 Why CoreWeave Is Uniquely Positioned to Lead AI Infrastructure00:13:32 Hiring for Both Scrappiness and Scale00:16:01 Post-IPO Whirlwind: Acquisitions, Debt Raises, and 10-Year Deals00:16:43 Sponsors – Sage Intacct | Mercury | RightRev00:20:13 Managing Investor Expectations With Radical Transparency00:22:39 Doubling Active Power in Six Months00:25:19 Risk-Balanced Capital Deployment: Power First, GPUs Second00:27:12 Financing GPUs With Delayed-Draw Facilities00:29:38 CoreWeave Rated Platinum for GPU Cluster Performance00:32:25 Compute as the Bottleneck for AI Growth00:33:47 Explaining Revenue Backlog Shape & Timing00:35:06 The Strength of Reserved Instance Contracts00:36:07 Giving Tight but Honest Guidance00:40:26 How Mega-Deals Require C-Suite Participation00:42:19 Tackling Revenue Concentration Through Diversification00:44:05 Building an AI-Only Cloud, Not a General-Purpose Cloud00:46:27 Capital Markets Muscle: Raising Billions at Speed00:47:47 Accounting Complexity in a Business With No Precedent00:49:33 Even the CFO Must Unlearn Old Cloud Assumptions00:51:29 Scaling Public-Company Processes in 90-Day Cycles00:54:42 The Couch Fire vs. House Fire Framework00:57:17 Balancing Risk Mitigation With Opportunity Seeking01:00:30 No Downtime for ERP Changes During Hypergrowth01:02:33 Why the Team Stays Energized Despite the Chaos#RunTheNumbersPodcast #CFOInsights #Hypergrowth #AIInfrastructure #FinanceStrategy This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ sits down with Greg Henry, CFO of 1Password and one of the most commercially minded finance leaders in tech, to break down why he left the public-company grind at Couchbase for a PLG-driven security business and what he's relearning in the private sphere. Greg explains how forecasting changes when the product does the selling, how to think about comp and pricing in a usage-led world, and the early tells that a model is quietly over- or under-performing. He shares why CFOs should meet far more customers than they do, how finance can drive revenue without stepping on sales, and what it actually takes for a company to plan with clarity instead of reacting. Greg also recounts the near-derailing of the Couchbase IPO, reflects on the “back nine” of his career, and offers grounded advice for aspiring first-time CFOs.—SPONSORS:RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.com—LINKS:Greg on LinkedIn: https://www.linkedin.com/in/greghenry23/1Password: https://1password.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Behind the Earnings Calls: Couchbase CFO Greg Henry on Consumption Models & Analyst Relationshttps://youtu.be/o_pDfz5a-Hw—TIMESTAMPS:00:00:00 Preview and Intro00:02:57 Sponsors – RightRev | Tipalti | Aleph00:07:03 Back in the Private Sphere: Why Greg Joined 1Password00:07:49 Greg's Four-Part Framework for a Great Role00:10:12 Thinking About the “Back Nine” & Legacy00:13:16 Transitioning to PLG & SLG at 1Password00:15:12 Blending PLG Efficiency with Enterprise Sales00:17:12 Sponsors – Fidelity Private Shares | Metronome | Mercury00:20:03 B2C vs. B2B ARPU Contrast00:22:41 Forecasting in PLG vs. Sales-Led Models00:24:18 Building Toward Chunky Enterprise Upside00:25:39 Comp Plans: Complexity, Pitfalls & the Alexander Group00:27:35 Keep Comp Plans Simple & Focused on ARR00:29:10 Why Mid-Year Comp Plan Changes Are Dangerous00:31:04 Governance & Guardrails for SPIFFs00:33:19 Using the CFO Network to Drive Revenue00:34:52 Why CFOs Must Meet Customers Directly00:36:19 Wallet Share & Being a Buyer AND a Seller00:38:08 Why He Avoids 3-Year+ Commitments00:40:20 How Much Discount Is a “Year” Worth?00:42:31 Greg's Structured Annual Planning Framework00:43:50 3–5% Upside/Downside Menu00:44:57 Comp Plans Must Go Out Early00:47:23 January Compensation & System Cutover Challenges00:48:31 Why Roadmap Alignment Must Kick Off Planning00:50:21 Sustain / Differentiate / Durable Growth / World-Class Teams Framework00:52:29 Couchbase IPO Almost Going Sideways00:54:59 How to Actually Become a CFO01:00:11 Legacy Greg Wants to Leave at 1Password#RunTheNumbersPodcast #CFOInsights #SaaSLeadership #PLGvsSLG #FinanceStrategy This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this Thanksgiving-week Mostly Growth episode, CJ Gustafson and Kyle Poyar ditch the serious finance talk for a looser, drinks-in-hand conversation with Ben Hillman, bouncing between CJ's nostalgic emo-punk concert adventure, the curse of vanity license plates, and the epidemic of “Y-axis crimes” in founder charts. They riff on Spotify Wrapped copycats, YouTube becoming living-room TV, kids' YouTube empires, and the game theory behind The Traitors and the Monty Hall problem before shifting into real-world pricing: newsletter perk economics, the pitfalls of hourly consulting, and why value-based packaging always wins. The episode stays playful but still sneaks in sharp insights on growth, psychology, and how weird the business world can be when you actually pay attention.—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—LINKS:Mostly Metrics: https://www.mostlymetrics.comCJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Growth Unhinged: https://www.growthunhinged.com/Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/Brian Balfour: brianbalfour.comBrian on LinkedIn: https://www.linkedin.com/in/bbalfour/Slacker Stuff: https://www.slackerstuff.com/Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/https://x.com/parikpatelcfa/status/1992706757073023191?s=46https://www.wired.com/story/null-license-plate-landed-one-hacker-ticket-hell/https://x.com/im_roy_lee/status/1992692253257855261/photo/1https://www.economist.com/finance-and-economics/2025/01/16/the-traitors-a-reality-tv-show-offers-a-useful-economics-lessonhttps://www.cdccard.com/https://nyulangone.org/news/one-third-americans-are-trying-avoid-gluten-it-villain-we-think-it-ishttps://x.com/techsalesguy3/status/1991585201601016161?s=46https://www.fletchpmm.com/https://paintvine.co.nz/blogs/news/the-legend-of-picassos-napkin-sketch?srsltid=AfmBOooiyTYGfUdKJZLpblbQAcJzQLg011Os_xeyaCgSpEIXrtIuD6hHhttps://cityfeedandsupply.com/https://www.linkedin.com/posts/cj-gustafson-13140948_started-from-the-email-now-were-here-activity-7397607230600126465-iVPv/https://cooking.nytimes.com/recipes/1018731-buttermilk-brined-roast-chickenhttps://cooking.nytimes.com/recipes/1026610-porcini-ragu—RELATED EPISODES:Is a weekly martini ARR? | with Dave Kellogghttps://youtu.be/Yb1lUQLJ6qw—TIMESTAMPS:00:00:00 Special Message00:00:35 Preview and Intro00:01:41 Sponsors – Pulley & Metronome00:04:01 Mostly Drinks Episode00:05:14 Concert Stories & Pop-Punk Nostalgia00:08:05 Concert Parenting & Full-Circle Moment00:08:36 Business Blunders Begin00:10:26 License Plate Fails & Accounting Humor00:12:08 Y-Axis Crime Chart Review00:14:21 Global Podcast “Success” & Listener Jokes00:16:00 Spotify Wrapped: Retention vs. Acquisition00:17:04 YouTube as the Future of Podcasts00:17:56 Kids' Shows, Blippi & Creator Economics00:18:55 The Traitors Show Overview00:20:30 Game Theory & Winning as a Traitor00:22:46 Monty Hall Problem Setup00:24:27 Game Show Logic & Gambler's Fallacies00:26:09 Pricing in the Real World00:27:03 Community Discount Card Business Model00:29:09 Newsletter Perks & Subscriber Value00:30:34 Marketplace Discount Math00:32:01 Negotiating Like a CFO00:33:00 Gluten-Free Nights & Pricing Strategy00:35:24 Outbound Pizza as a Go-to-Market Play00:37:03 Outbound Pizza Tuesdays to Gluten-Free Tuesdays00:37:37 Pricing Services: Value vs. Hourly00:40:47 The Picasso Pricing Story00:42:55 Harvard Business School Case Study & Kim K Photo00:44:02 Thanksgiving Cooking: Roast Chicken & Porcini Ragu00:44:56 Wrap & Credits#MostlyGrowthPodcast #SaaSOperators #BusinessStrategyPod #CreatorEconomyTalks #FinanceNerds This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

How do you know when a company is ready to go public? And what do you do to prepare for this? Chirag Shah, CFO of Motive and former CFO of Kong and Cornerstone OnDemand, joins CJ to share insights from his experience of scaling businesses from $30 million to nearly $1 billion and tripling ARR. He talks about taking companies public and how he helped take one private again in a $5.2 billion deal. In this episode, he explains what signals indicate that a company is ready to accelerate its growth, the art and science of building sales capacity, and how to balance efficiency and growth in hypergrowth mode. He also covers how to achieve a great valuation without a strong performance, the biggest headache on the road to IPO, and whether you should IPO in the first place or remain private.—SPONSORS:Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—Chirag Shah on LinkedIn: https://www.linkedin.com/in/chirag-shah-787b1b20/Motive: https://gomotive.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:From $30M to Almost $1B: A Guide to Hypergrowth, IPO Prep, and Navigating the Public Markethttps://youtu.be/_pJfdN5p-ik—TIMESTAMPS:00:00:00 Preview and Intro00:02:57 Sponsors – Mercury | RightRev | Tipalti00:06:49 Motiv CFO Intro & Company Background00:07:01 Product Market Fit as a CFO00:09:26 Lessons From Taking Companies Public00:11:04 Preparing for Life as a Public Company00:11:26 Moving From Finance Into a GM Role00:12:50 Learning the Business Beyond Finance00:14:23 Empathy for Sales & Carrying a Quota00:15:51 Sponsors – Aleph | Fidelity Private Shares | Metronome00:19:03 Asking Better Questions After Operating Experience00:21:23 Knowing When to Accelerate Growth00:23:16 High-ROI Capacity Signals00:24:51 Scaling Requires Supporting Functions00:26:19 The Art + Science of Adding Reps00:27:53 Sales Team Buy-In Before Scaling00:29:15 Reading Product-Market Fit Through Sales00:30:08 Where Scaling Breaks First (Enablement)00:31:36 Importance of SE / SC Ratios00:33:13 Timing Supporting Hires00:34:32 Maintaining Momentum While Scaling00:36:33 Longest Pole in IPO Prep: Predictability00:38:47 Building Confidence Through Consistency00:40:45 Large Deals Swing Small Companies00:42:41 Growth Still Drives Quarterly Volatility00:44:43 Investor Education as a Core IPO Task00:46:00 Harder to Make Big Changes Publicly00:47:39 Managing Morale in Volatile Markets00:48:33 Taking Cornerstone Private00:52:32 Advice: Know Why You Want to Go Public00:56:18 Efficiency Without Sacrificing Growth01:00:58 Operating Roles Prepared Him for CFO01:06:23 Finance Software Stack Overview#RunTheNumbersPodcast #Hypergrowth #IPOreadiness #CFOInsights #MostlyClassics This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Serving SMB mid-market customers is one thing, but when you go upstream to enterprise sales, everything changes: go-to-market strategy, the sales process, how you structure deals, even how you define customer value. Today's guest, Andrew Casey, has helped scale four SaaS companies: ServiceNow, WalkMe, Lacework, and his current company, Amplitude. At ServiceNow, he worked closely with Snowflake's Mike Scarpelli and Coatue's David Schneider, and he was instrumental in establishing the company's deal desk to support its sales motion. As an operationally focused CFO, he shares a wealth of knowledge on the importance of staying close to the customer, structuring deals that work for both sides, establishing transparency in usage-based pricing, aligning incentives and strategy in sales, the pros and cons of multi-year deals, the problem with auto-renewals and what to do instead, and how to adapt your go-to-market strategy when moving from SMB mid-market to enterprise.—SPONSORS:Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.—Andrew Casey on LinkedIn: https://www.linkedin.com/in/andrew-casey-6b14875/Amplitude: https://amplitude.comCJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:An Operationally-Focused CFO's Guide to Scaling From SMB to Enterprise: Lessons From ServiceNowhttps://youtu.be/iUpMAQ14YpM—TIMESTAMPS:00:00:00 Preview and Intro00:03:27 Sponsors – Metronome, Mercury, RightRev00:07:08 Andrew joins the podcast00:08:10 Becoming an operational CFO00:09:25 Early customer-empathy beginnings at Sun00:11:34 How customer-empathy shaped Andrew's career00:14:08 Navigating HP's troubled EDS contracts00:16:05 Sponsors – Tipalti, Aleph, Fidelity Private Shares00:19:37 Returning from ads – running toward hard markets00:20:13 Scaling ServiceNow's sales operations00:23:27 Breaking into the trusted circle after the Q1 miss00:25:26 Building and scaling the ServiceNow deal desk00:28:11 Principles of transparent, value-aligned pricing00:30:17 Rethinking metering models and usage alignment00:33:01 Diagnosing budget constraints vs. cash timing00:36:14 Incentives, comp plans, and high-trust selling00:39:21 Training enterprise reps for long-term value00:40:17 Multi-year deals and when they actually work00:43:05 Overselling, discount levers, and ZIRP contract bloat00:45:58 How enterprise scale transforms go-to-market00:51:03 Pipeline coverage and maturity modeling00:54:02 Not all pipeline dollars are created equal00:57:05 Career-risk mindset in enterprise selling01:00:02 Defining enterprise and moving upmarket01:01:00 A business-first approach to the CFO role01:03:10 Getting hired at ServiceNow01:06:37 Building GTM finance, deal desk, and a 400-person org01:08:00 Lightning round – biggest mistakes and IR lesson01:11:10 Advice to his younger self and leading through change01:13:34 Defining customers, ARR accuracy, and hierarchy pitfalls01:15:12 The wildest expense attempt ever submitted#RunTheNumbersPodcast #SaaSFinance #EnterpriseSelling #GTMStrategy #CFOInsights This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Brian Balfour, Founder & CEO of Reforge and former VP of Growth at HubSpot, joins Mostly Growth to explore why product-market fit is a moving target. He introduces the concept of the Product-Market Fit Treadmill, a state where rising customer expectations and competitive pressure make it harder than ever to stay ahead. Brian breaks down how AI has accelerated PMF collapse, explains the hidden costs of product adoption, and shares how Reforge shipped five AI-native products with a team of just 20 people. Packed with frameworks, strategic insight, and startup realism, this episode is essential listening for product leaders, operators, and founders navigating the next wave of GTM.—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—LINKS:Mostly Metrics: https://www.mostlymetrics.comCJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Growth Unhinged: https://www.growthunhinged.com/Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/Brian Balfour: brianbalfour.comBrian on LinkedIn: https://www.linkedin.com/in/bbalfour/Slacker Stuff: https://www.slackerstuff.com/Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/https://brianbalfour.com/four-fits-growth-frameworkhttps://x.com/amasad/status/1981201454032703662?s=46https://getlatka.com/companies/firefliesaihttps://x.com/rowancheung/status/1988218743952916537?https://gamma.app/insights/how-we-built-a-usd100m-business-differently—RELATED EPISODES:When the marketing math doesn't math | with Emily Kramerhttps://youtu.be/sSuoV_YSrlwWhy Founders Are Posting Sad Dinnershttps://youtu.be/Zl6NSIHF2Gk—TIMESTAMPS:00:00:00 Preview and Intro00:01:51 Sponsors – Pulley, Metronome00:04:11 Introducing Brian Balfour & Reforge background00:07:22 Evergreen frameworks & Four Fits resurgence00:11:01 PMF treadmill and rising expectations00:14:26 AI shocks and PMF collapse (Chegg)00:16:43 CRM expectations & AI-native workflows00:20:44 R&D as ongoing cost to serve00:22:26 Customers buying based on future product velocity00:24:32 Communicating rapid releases & driving adoption00:25:17 Reforge's expanding AI product suite00:27:52 Product delivery vs. product adoption bottlenecks00:29:32 Platform distribution shifts introduction00:30:51 Evaluating emerging platforms00:32:04 The open → close platform cycle00:33:31 Moats, escape velocity & platform dominance00:36:32 Choosing major vs. emerging platforms00:40:22 ChatGPT dominance in AI discovery00:42:16 Hiring, resumes & filtering AI-generated applications00:43:30 AI note-taking market & “Flintstoning”00:47:03 Trying Gamma & AI-generated presentation tools00:50:08 AI onboarding innovations (WhatsApp agent)#MostlyGrowthPodcast #ProductMarketFit #BrianBalfour #StartupStrategy #Reforge This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this special episode of Run the Numbers, CJ Gustafson records live from Campfire's AI Finance Forward conference in San Francisco, serving up a trio of rapid-fire interviews with top-tier finance leaders. First, Daniel Kang, CFO of Mercury, breaks down the quality of fintech revenue streams, the mechanics of float in a falling rate environment, and what investors really value. Then, Brad Floering, SVP of Finance at Snowflake, shares war stories on usage-based pricing, forecasting consumption, and the role of AI in modern FP&A. Finally, Mitzi Yue of Boulder Care brings a mission-driven perspective, reflecting on dual roles in finance and culture, career product-market fit, and the ethical frontier of AI in healthcare. It's a fast, thoughtful taste of where modern finance is headed.—LINKS:Daniel Kang on LinkedIn: https://www.linkedin.com/in/dmkang/Mercury: https://mercury.com/Brad Floering on LinkedIn: https://www.linkedin.com/in/brad-floering/Snowflake: https://www.snowflake.com/Mitzi Yue on LinkedIn: https://www.linkedin.com/in/mitziyue/Boulder Care: https://www.boulder.care/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Grindr's $0 CAC Secret from the CFO Who Launched Disney+ | Vanna Krantzhttps://youtu.be/ijFIMmtpLNw—TIMESTAMPS:00:00:00 Preview and Intro00:04:03 Sponsors – Fidelity Private Shares, Metronome, Mercury00:06:49 Guest – Daniel Kang (Mercury) joins00:07:55 Lessons from being first finance hire00:10:49 Finance collaborating on product decisions00:13:12 Comparing customer segments and revenue models00:16:58 Sponsors – Right Rev, Tipalti, Aleph00:21:11 Market shift for consumer fintech models00:23:14 Balancing gross profit with product growth00:24:41 Misconceptions about fintech revenue00:26:57 Guest – Brad Floering (Snowflake) joins00:30:22 Aligning pricing with cloud resource consumption00:33:17 Forecasting challenges with usage-based revenue00:35:06 Complexity of sales commissions under consumption model00:38:23 Lessons from AWS: committing for discounts00:41:16 Cold start forecasting challenges and the role of employee size00:44:01 Customer behavior and rollover credit challenges00:47:08 Using professional services to recover unused credits00:49:05 Seasonality and forecasting challenges in Q400:54:16 Guest – Mitzi Yue (Boulder Care) joins00:57:05 The pandemic's impact on telemedicine adoption01:00:33 Finance decisions with human consequences in healthcare01:02:26 Finding personal product-market fit in Series B/C stage01:03:33 Finance as the central nervous system of the company01:07:10 Nonprofits inspired by personal values and experience01:10:52 Exploring AI's potential in healthcare and finance—SPONSORS:Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run—#RunTheNumbersPodcast #FintechStrategy #UsageBasedPricing #HealthcareFinance #AIinFinance This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ Gustafson sits down with Vanna Krantz, former CFO of Disney+ and Grindr, to explore what it takes to lead finance through massive inflection points. Vanna reflects on building Disney+'s subscription model from scratch under Bob Iger's leadership and the pressure of launching a global product with no precedent. She discusses forecasting as both science and art, and the importance of appreciating high-stakes moments amid chaos. Shifting to Grindr, Vanna breaks down how the company went public with remarkable efficiency—boasting 40% EBITDA margins and under 200 employees—and how she modeled for a user base that consistently churns and returns. She also opens up about career longevity, work-life balance, and helping women find sustainability and acceleration in leadership.—LINKS:Vanna on LinkedIn: https://www.linkedin.com/in/vannakrantz/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Monetizing Community Engagement: The Business of Fitness with Strava CFO Lily Yanghttps://youtu.be/zlLb5yZDKQE“Let's Just See What Breaks” — Intuit's CFO on Being a Disruptor When You're Already the Incumbenthttps://youtu.be/Le1D9HXHvGI—TIMESTAMPS:00:00:00 Preview and Intro00:03:02 Sponsors – Aleph, Fidelity Private Shares, and Metronome00:06:09 Meeting at A16z and Disney Plus Discussion00:07:13 Interviewing with Bob Iger and Joining Bamtech Media00:10:43 Forecasting the Unknown at Disney Plus00:13:01 Launch Strategy – Mandalorian and Retention00:15:15 Sponsors – Mercury, RightRev, and Tipalti00:19:23 Forecasting, Retention Curves, and the Art vs. Science Balance00:22:20 Lessons in Art and Science of Finance at Disney00:25:08 Launch Day Chaos and the Disney Plus CDN Outage00:26:24 Celebrating the 10 Million Subscriber Milestone00:27:21 Grindr IPO and Financial Discovery00:32:42 Active User Metrics and Reactivation Trends00:34:29 Seasonality and Human Behavior in App Usage00:36:02 Free vs. Paid Users and Revenue Optimization00:38:21 Pricing Strategy and Global Monetization00:40:23 Women in Leadership and Staying in the Game00:43:30 Work–Life Balance and Career Seasons00:46:12 Wisdom, Experience, and Staying in the Game00:50:08 Finance Stack, Craziest Expense, and Closing Remarks—SPONSORS:Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.—#RunTheNumbersPodcast #CFOInsights #DisneyPlus #GrindrIPO #Leadership This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Mostly Growth, CJ Gustafson and Kyle Poyar dig into what it means to be useful rather than just right at work, exploring how communication, empathy, and impact matter more than technical precision as careers mature. They share candid lessons from their own paths—CJ's focus on making others look good to earn promotions and Kyle's evolution into a domain expert through public writing—before unpacking what separates good from great VPs of Sales with insights from Pavilion founder Sam Jacobs. The conversation then shifts to OpenAI's “too big to fail” claims, the economic ripple effects of AI infrastructure spending, and how finance leaders can stay grounded in reality. Rounding out the episode, the hosts preview their latest research—CJ's “Agentic Finance” report on AI in the finance stack and Kyle's 2025 SaaS Benchmarks—and close with lighthearted banter about founder age stats, home maintenance mishaps, and the price of professional Christmas lights—LINKS:Mostly Metrics: https://www.mostlymetrics.comCJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Growth Unhinged: https://www.growthunhinged.com/Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/Slacker Stuff: https://www.slackerstuff.com/Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/https://sarahcharlton.substack.com/p/from-being-right-to-being-usefulhttps://www.highalpha.com/saas-benchmarkshttps://www.mostlymetrics.com/p/presenting-the-state-of-the-agentic-financial-stackhttps://www.mostlymetrics.com/p/finance-in-2030https://worksinprogress.co/issue/the-algorithm-will-see-you-now/https://www.theinformation.com/briefings/openai-ceo-sam-altman-forecasts-20-billion-annualized-revenue-yearhttps://www.growthunhinged.com/p/your-pricing-is-broken—RELATED EPISODES:When the marketing math doesn't math | with Emily Kramerhttps://youtu.be/sSuoV_YSrlwGetting fired 4 times made me a founder | Sam Jacobs of Pavilionhttps://youtu.be/8X-JVOF-1A0How To Win at Early Stage Sales With the Guy Who Helped Take Snyk From $0 to $100M+https://youtu.be/VKrZCte8fyM996 Culture, Exploding AI Bills & SaaS Chaoshttps://youtu.be/qhrxDL0gsRo—TIMESTAMPS:00:00:00 Preview and Intro00:02:18 Sponsors – Pulley and Metronome00:05:09 Flight Cancellation and Airport Chaos00:07:58 Being Right vs. Being Useful00:11:17 Getting Promoted Early by Making Others Look Good00:15:25 What Separates a Good VP of Sales from a Great One00:18:24 Sales Leaders as Capital Allocators00:21:14 The Organizational Tax of Sales Support00:22:33 Is OpenAI Too Big to Fail?00:25:31 AI Investments, Alternatives, and Market Impact00:27:50 Bailouts and Economic Reality00:28:20 Agentic Finance and the AI-Driven Finance Stack00:31:43 SaaS Benchmarks Report 2025 Overview00:33:59 Growth Rates by ARR Tier and Scale00:35:40 AI's Impact on Engineering Teams00:37:45 Age and Startup Success00:39:42 Building Durable Businesses Over Time00:41:25 Something You Tried This Week – HVAC Cleaning00:43:19 Outsourcing Holiday Cheer – Professional Light Installation00:47:08 Credits – Mostly Growth Closing Remarks—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—#MostlyGrowthPodcast #StartupFinance #AIPodcast #SaaSLeadership #GoToMarket This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ sits down with Jeff Bernstein, managing partner at Riveron, to unpack what really happens when a company decides it might be time to go public. Jeff draws on his experience across banking, hedge funds, operating roles, and advisory work to break down IPOs, dual-track processes, and the surprising realities behind price discovery—including why a 20x-oversubscribed book isn't what it seems. He also dives into the re-emergence of SPACs, what's different this time, and the key considerations CFOs should weigh before choosing that route. From IPO-readiness must-haves to building the muscle memory needed for public-company life to the sketchiest EBITDA adjustment he's ever seen, Jeff brings stories, frameworks, and hard-won lessons for any finance leader thinking about the road to the public markets.—LINKS:Jeff Bernstein on LinkedIn: https://www.linkedin.com/in/jeff-bernstein-498a23158/Company: https://riveron.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:00:00:00 Preview and Intro00:02:59 Sponsors – Tipalti, Aleph, Fidelity Private Shares00:06:20 The Mechanics of Going Public at Riveron00:09:59 The State of Tech Capital Markets00:11:19 Comparing the Internet, Mobile, and AI Waves00:14:11 Understanding Dual Track Processes00:15:34 Sponsors – Metronome, Mercury, RightRev00:19:35 Why Companies Choose to Go Public or Sell00:23:02 Why Price Discovery Is Harder in Today's Market00:26:05 The Pros and Cons of Direct Listings00:29:16 Balancing Fairness Between Employees and Investors00:30:47 Inside the IPO Pricing Process00:34:26 How Banks and Investors Game Allocations00:41:22 The Return of SPACs and Why They're Back00:43:46 Key Considerations for CFOs Evaluating SPAC Mergers00:47:53 The Most Successful SPACs to Date00:49:00 Building Public Company Readiness00:52:03 Developing Muscle Memory for Quarterly Reporting00:55:31 The CFO's Role as Chief Communicator00:57:47 Long-Ass Lightning Round – Overhyped Metrics and Sketchy EBITDA—SPONSORS:Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.—#RunTheNumbersPodcast #IPOmistakes #CFOinsights #SPACs #FinanceLeadership This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ Gustafson sits down with Colin Gardiner, General Partner at Yonder VC and former Chief Revenue and Product Officer at Outdoorsy, to unpack what really drives successful marketplace businesses. Colin shares lessons from scaling a peer-to-peer RV platform, where the biggest unlock came not from casual users but from power hosts optimizing utilization and yield through the SaaS tools they built. He introduces his “Marketplace Plus” investing framework—showing how layering SaaS and professional tools can transform a platform into an operating system—and where founders risk overreaching by taking on inventory or managing supply too tightly. The conversation dives deep into monetization, pricing psychology, take rates, and the fine balance between product-market fit and margin obsession, before zooming out to explore how AI and the decline of SEO are reshaping marketplace discovery.—LINKS:Colin on LinkedIn: https://www.linkedin.com/in/colingardiner/Company: https://www.yonder.vc/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:996 Culture, Exploding AI Bills & SaaS Chaoshttps://youtu.be/qhrxDL0gsRo“Keep the Take Rate Low” - Turo's Chuck Fisher on Scaling a Successful Peer-to-peerhttps://youtu.be/LKH8o1MjnZoThe Art of Stacking S-Curves: Olo's Winning Vertical SaaS Strategy with CFO Peter Benevideshttps://youtu.be/1X2VoYogj44—TIMESTAMPS:00:00:00 Intro and Guest Overview00:02:57 Sponsors – RightRev, Tipalti, and Aleph00:07:13 Outdoorsy and the RV Market00:10:33 Balancing Supply and Demand00:13:05 Marketplace Plus Model00:16:59 Sponsors – Fidelity Private Shares, Metronome, and Mercury00:21:45 Professionalizing Marketplaces00:24:10 Building Software, Insurance, and Financing Layers00:28:07 Avoiding Fully Managed Models00:32:34 Take Rates and Pricing Strategy00:35:00 Monetizing Both Sides00:37:06 Advertising and Marketplace Scale00:39:48 Marketplaces Meet Social Platforms00:42:36 AI and Marketplace Distribution00:45:54 AI Agents and Matchmaking00:47:03 When AI Becomes the Supply00:49:09 Negative Gross Margins and Scale00:53:04 Picking a Side – Supply or Demand00:54:35 Branding, Utilization, and Growth00:55:42 Closing and Credits—SPONSORS:RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.com—#RunTheNumbersPodcast #MarketplaceStrategy #AIPoweredBusiness #SaaSModel #StartupFinance This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this high-energy episode of Mostly Growth, CJ Gustafson, Kyle Poyar, and Ben Hillman dive into the hidden levers of SaaS growth and what truly separates startups that scale to $20M+ ARR from those that stall out. They explore eye-opening data from 6,500 companies, revealing how the best improve net retention, raise pricing, and re-engineer their revenue models over time. Alongside the metrics, there's plenty of playful chaos—like a naming debate over “Yoshinobu Yamamoto Gustafson,” a rapid-fire game of “Founder or Pop Star,” and CJ's accidental IPO embargo break. It's part insight, part inside joke, and 100% for SaaS operators and C-suite climbers.—LINKS:Mostly Metrics: https://www.mostlymetrics.comCJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Growth Unhinged: https://www.growthunhinged.com/Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/Slacker Stuff: https://www.slackerstuff.com/Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/https://www.growthunhinged.com/p/the-compounding-startuphttps://www.growthunhinged.com/p/the-odds-of-making-ithttps://www.superme.ai/kylepoyar?conversationId=VgDXTOl2Z89mW7UYXstU0bhttps://a16z.com/anatomy-of-an-enterprise-platform-company/https://www.investopedia.com/terms/h/hhi.asphttps://navan.com/https://www.mostlymetrics.com/p/navan-ipo-s1-breakdownhttps://x.com/amendandpretend/status/1983588137453416763?s=46https://x.com/ryan_c_walsh/status/1983705182371475630?s=46https://www.reddit.com/r/TwinCities/comments/z6hxp8/how_much_are_people_paying_for_residential_snow/—RELATED EPISODES:Getting fired 4 times made me a founder | Sam Jacobs of Pavilionhttps://youtu.be/8X-JVOF-1A0Why Founders Are Posting Sad Dinnershttps://youtu.be/Zl6NSIHF2Gk—TIMESTAMPS:00:00:00 Preview and Intro00:01:55 Sponsors – Pulley & Metronome00:04:25 Dodgers Banter & Baby Naming00:05:38 Founder or Pop Star Game00:07:50 ChartMogul Data & Growth Levers00:08:30 Expansion, Upsell & Retention Discussion00:15:53 Testing Kyle's AI Avatar00:17:07 CJ's AI Self-Query & Beta Discussion00:18:04 AI Use Cases & Knowledge Retention00:22:03 Platform Debate & A16z Analysis00:24:29 Herfindahl-Hirschman Index Explained00:25:34 Platform Metrics & Valuation Upside00:26:48 CrowdStrike, Datadog & Multi-Product Expansion00:28:13 Core Systems of Record & AI's Impact00:29:49 Business Blunders – Navan IPO & Snowflake CRO00:34:07 Snow Removal Pricing & Insurance Logic00:35:56 Closing Remarks & Credits—SPONSORS:Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comPulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics—#MostlyGrowthPodcast #SaaSGrowth #StartupStrategy #B2BTech #RevenueRetention This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ Gustafson sits down with Sam Jacobs, Founder and CEO of Pavilion, the global community for GTM leaders. Sam shares how getting fired multiple times as a CRO led him to build a business rooted in belonging — one that monetized members first, prioritized intimacy over growth, and turned a Slack group into a multimillion-dollar company. He and CJ unpack the mechanics of community: the tradeoffs between exclusivity and expansion, why venture capital doesn't always fit human-centered businesses, and how Pavilion balances pricing, curation, and access. They also explore the evolution of the GTM function — from the myth of the plug-and-play VP of Sales to how AI is reshaping RevOps, forecasting, and leadership. Finally, Sam reflects on building durable value beyond personal brand and what it really takes to scale trust as a product.—LINKS:Sam Jacobs on LinkedIn: https://www.linkedin.com/in/samfjacobs/Company: https://www.joinpavilion.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:E120: What does the future of tech look like when it costs $0 to switch software?https://www.youtube.com/live/Cpw2pkq-FXI?si=-0y0tcLTIlIbkmyOCFOs: Want to Outmaneuver Your Competitors? Here's the Jedi Mind Trickhttps://youtu.be/Yte_fe1xF90?si=hVfgdd0Fg0PQuuoSThe Gross Margin Episode with Sarah Wang of a16zhttps://youtu.be/72aP5ohBxvE—TIMESTAMPS:00:00:00 Preview and Intro00:03:05 Sponsors – Mercury, RightRev, and Tipalti00:06:50 Pavilion, Community, and Go-to-Market Leadership00:10:28 Career Tenure and Executive Turnover00:12:55 Compensation Structure and Equity Negotiation00:14:31 Building Wealth Through Equity00:16:30 Sponsors – Aleph, Fidelity Private Shares, and Metronome00:19:36 Managing Wealth, Lifestyle, and Longevity in Leadership00:22:58 Founding Pavilion to Empower Operators00:25:13 Taking Roles for Learning, Titles, and Leverage00:28:47 Contrarian Executives, Team Dynamics, and Leadership Lessons00:30:36 What Makes a Great VP of Sales00:33:23 Revenue, Profitability, and Misaligned Incentives00:35:08 Quota Setting, Forecasting, and Spreadsheet Pitfalls00:39:07 AI in Sales and the Myth of the AI SDR00:40:32 The Future of Playbooks in the Age of AI00:43:38 The Dangers of AI and the Need for Humans in the Loop00:45:27 Monetizing Pavilion – Memberships, Sponsors, and Pricing Strategy00:49:30 Building Higher-Margin Community Businesses00:57:46 Building a Personal Brand with Long-Term Value01:01:52 Closing Credits and Outro—SPONSORS:Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com#RunTheNumbersPodcast #Finance #CommunityBuilding #Leadership #GoToMarket This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ Gustafson sits down with Teddy Collins, EVP of Finance at SeatGeek, who helped scale the company from its first in-house finance hire to a tech-forward finance team powering one of the most dynamic businesses in live events. Teddy shares what it was like leading finance through the pandemic when live events went dark overnight, how that period reshaped his approach to forecasting and uncertainty, and how SeatGeek is now using AI and machine learning to enhance planning accuracy and decision-making. He and CJ also dive into how finance can evolve from a cost center to a strategic partner, the toughest manual processes he's eliminated, and where he sees the next big leap in the CFO tech stack. Finally, Teddy opens up about his rapid rise—four promotions in ten years—and offers practical advice on career growth, feedback, and building trust in a world where AI is redefining what “junior” really means.—LINKS:On LinkedIn: https://www.linkedin.com/in/teddycollins/Company: https://seatgeek.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:CFO of FloQast on Why Finance Teams are Data Curators—TIMESTAMPS:(00:00:00) Preview and Intro(00:02:49) Sponsor – Metronome | Mercury | RightRev(00:06:36) Joining SeatGeek and the Early Finance Journey(00:08:05) Managing Finance When Live Events Went Dark(00:10:23) Forecasting Through Uncertainty(00:13:12) Building Systems and Processes from Scratch(00:15:34) Sponsor – Tipalti | Aleph | Fidelity Private Shares(00:18:06) Using AI and Machine Learning in Forecasting(00:22:44) Build vs. Buy: SeatGeek's Tech Philosophy(00:26:31) Turning Finance into a Strategic Partner(00:30:42) Killing Manual Processes and Automating Insights(00:34:55) The Next Big Leap in the CFO Stack(00:38:46) Leading Teams Through Change and Growth(00:42:11) Talent, Tools, and the Future of Finance Roles(00:46:07) Climbing the Ladder: Four Promotions in Ten Years(00:49:50) Career Advice and Earning Trust in Fast-Growing Teams(00:53:16) How AI Is Reshaping the Definition of “Junior”(00:56:22) Lightning Round and Closing Thoughts—SPONSORS:Today's podcast is brought to you by Metronome. You just launched your new AI product. The new pricing page looks great. But behind it? Last-minute glue code, messy spreadsheets, and running ad-hoc queries to figure out what to bill. Customers get invoices they can't understand. Engineers are chasing billing bugs. Finance can't close the books. With Metronome, you hand it all off to the real-time billing infrastructure that just works—reliable, flexible, and built to grow with you. We turn raw usage events into accurate invoices, give customers bills they actually understand, and keep every team in sync in real time. Whether you're launching usage-based pricing, managing enterprise contracts, or rolling out new AI services, Metronome does the heavy lifting so you can focus on your product, not your billing. That's why some of the fastest-growing companies in the world, like OpenAI and Anthropic, run their billing on Metronome. Visit metronome.com to learn more.Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.#RunTheNumbersPodcast #FinanceLeadership #CFOStack #AIForecasting #SeatGeek This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Gross margins, GPUs, and the future of finance — this one's for the metrics nerds. CJ sits down with Sarah Wang, General Partner at Andreessen Horowitz, to talk about what happens when the traditional SaaS playbook collides with AI. Sarah shares how legacy benchmarks like payback period and burn multiple start to break down in a world where compute, not headcount, drives costs. She explains why sky-high gross margins can actually be an orange flag, how finance leaders can think about resource allocation between engineers and GPUs, and why the most valuable finance teams today are deeply operational. They also unpack what it's like partnering with AI-native founders, the evolution of pricing models as LLM costs drop, and whether we'll see a private trillion-dollar company anytime soon.—LINKS:on LinkedIn: https://www.linkedin.com/in/sarah-wang-59b96a7/Company: https://a16z.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:996 Culture, Exploding AI Bills & SaaS ChaosFrom Credit Karma to Notion: CFO Rama Katkar on Leading Finance Through Every Growth Stage5,762 Job Applications. Zero Offers.Thinking About Adding Payments to Your Software Product? Listen to This First!—TIMESTAMPS:(00:00:00) Preview and Intro(00:02:40) Sponsors – Fidelity Private Shares, Mercury, RightRev(00:05:50) Sarah Joins the Show(00:06:06) The Future of Excel in the Age of AI(00:08:24) Why Gross Margins Don't Tell the Whole Story(00:10:42) When Sky-High Margins Are an Orange Flag(00:12:57) Finance as a Strategic Lever in AI Companies(00:15:04) Sponsors – Tipalti, Aleph, Rillet(00:17:22) Partnering with AI-Native Founders(00:20:35) When Traditional SaaS Benchmarks Break Down(00:23:58) Forecasting and Financial Planning for Compute Costs(00:27:16) The Engineers-Versus-GPUs Trade-Off(00:30:29) Resource Allocation and Infrastructure Efficiency(00:33:47) How Pricing Models Evolve as LLM Costs Drop(00:37:15) Circular Finance: When Big Tech Funds Its Own Vendors(00:40:39) Metrics That Still Matter in AI-Driven Businesses(00:44:12) The Evolving Role of Finance Leaders(00:47:26) What “Operational Finance” Really Means(00:50:58) Building Sustainable Efficiency in AI Companies(00:54:03) Will We See a Private Trillion-Dollar Company?(00:55:33) Outro—SPONSORS:Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics#RunTheNumbersPodcast #FinanceLeadership #AIinBusiness #VentureCapital #SaaSMetrics This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Check out Mostly Growth and get episodes early. Available on all platforms.* YouTube* Spotify* AppleIn this episode, CJ Gustafson, Kyle Poyar, and Ben Hillman dive into the concept of “sloponomics”—a tongue-in-cheek look at the overwhelming flood of mediocre AI-generated content and what it means for creators, startups, and investors. They discuss how unique voices and genuine creativity will stand out in an AI-saturated landscape, the economic parallels between modern content creation and startup growth, and the tricky dynamics of building sustainable momentum in a world of noise. The trio also unpack the “$10K MRR” meme, pricing psychology, and the difference between chasing vanity metrics and building lasting value. With humor and real-world insight, they explore how AI, distribution, and early-stage investment are reshaping what success looks like in tech and media.Timestamps:00:00 Preview and Intro00:35 Being Mean to AI and Early Banter02:05 When You're Rude to AI: The Penn State Study04:57 Sponsor – Metronome06:02 The Rise of AI-Generated “Slop” Content07:15 The Creator “Haves and Have-Nots”09:00 Losing Credit to AI Models11:20 Feeding the Beast: 400 Posts Later13:13 “Slop Talk” and Human-Made Slop14:27 The $10K MRR Meme and Startup Momentum15:49 Pricing Psychology and Product Traction17:42 Hunting Mice, Buffalo, and Elephants20:19 Venture Funds, Bubbles, and Ecosystem Investing23:39 When Startups Invest in Startups26:25 Slack, Lattice, and the Platform Play30:39 Wrapping Up and Late-Night Insights33:12 The Hemingway Story and CJ's No-Instagram Lifestyle36:10 Electric Boats, Group Discounts, and Sign-OffEpisodes Referenced:Slop Talk (coming soon)⁠https://www.youtube.com/slackerstuff⁠Why Only 2% of Startups Make ItWhen startups burn cash faster than they learn | Ivan Makarov:⁠996 Culture, Exploding AI Bills & SaaS Chaos⁠Links:⁠https://www.dexerto.com/entertainment/study-proves-being-rude-to-ai-chatbots-gets-better-results-than-being-nice-3269895/⁠⁠https://www.usg.edu/galileo/skills/unit07/internet07_02.phtml⁠⁠https://futurism.com/altman-please-thanks-chatgpt⁠⁠https://futurism.com/artificial-intelligence/over-50-percent-internet-ai-slop⁠⁠https://www.axios.com/2025/10/14/ai-generated-writing-humans⁠⁠https://www.economist.com/business/2025/10/16/sloponomics-who-wins-and-loses-in-the-ai-content-flood⁠⁠https://x.com/madhuraaa_/status/1978390720881819884⁠⁠https://www.mostlymetrics.com/p/eat-what-you-kill⁠⁠https://christophjanz.blogspot.com/2014/10/five-ways-to-build-100-million-business.html⁠⁠https://www.growthunhinged.com/p/how-to-build-your-early-gtm-strategy⁠⁠https://www.mostlymetrics.com/p/startups-investing-in-startups-peak-bubble-behavior⁠⁠https://www.economist.com/science-and-technology/2025/10/10/are-barefoot-shoes-good-for-runners⁠⁠https://x.com/ivanomaksf/status/1978852000298320068?s=46⁠⁠https://www.linkedin.com/news/story/uber-offers-drivers-extra-pay-to-perform-tasks-that-train-ai-7116401/⁠⁠https://www.mostlymetrics.com/p/is-ltv-to-cac-the-nickelback-of-metrics⁠⁠https://www.hollywoodreporter.com/tv/tv-news/final-2024-25-network-tv-ratings-tracker-high-potential-1236312223/⁠⁠https://christophjanz.blogspot.com/2014/10/five-ways-to-build-100-million-business.html⁠⁠https://www.theinformation.com/articles/ben-horowitz-hires-jensen-vercel-starts-venture-fund⁠⁠https://www.instagram.com/chasemytail/Today's podcast is brought to you by MetronomeYou just launched your new AI product. The new pricing page looks great. But behind it? Last-minute glue code, messy spreadsheets, and running ad-hoc queries to figure out what to bill. Customers get invoices they can't understand. Engineers are chasing billing bugs. Finance can't close the books.With Metronome, you hand it all off to the real-time billing infrastructure that just works—reliable, flexible, and built to grow with you. We turn raw usage events into accurate invoices, give customers bills they actually understand, and keep every team in sync in real time.Whether you're launching usage-based pricing, managing enterprise contracts, or rolling out new AI services, Metronome does the heavy lifting so you can focus on your product, not your billing.That's why some of the fastest-growing companies in the world, like OpenAI and Anthropic, run their billing on Metronome.Visit metronome.com to learn more. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ sits down with Michael Stanisz, Partner at Revenue Management Labs, the person companies call when their pricing model stops making sense. For decades, software pricing was predictable: sell more seats, add more margin. But with AI, every usage prompt has a real cost, and the old economics no longer hold. CJ and Michael dive into what happens when your product looks like software but behaves like infrastructure, how pricing power erodes as features become free, and why value-based pricing might not be as customer-friendly as it sounds. They also explore the chaos of real-world pricing: from Microsoft cloning your startup to measuring ROI when your product's impact is undeniable but hard to prove; all wrapped in sharp insights and a few “we still run this on DOS” war stories.—LINKS:Michael on LinkedIn: https://www.linkedin.com/in/michael-stanisz-27418a28Revenue Management Labs: https://revenueml.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:“Anything new needs to have AI core to its offering”: Amy Butte, How Navan Is Redefining Finance OpsFrom Credit Karma to Notion: CFO Rama Katkar on Leading Finance Through Every Growth Stage—TIMESTAMPS:(00:00:00) Preview and Intro(00:02:23) Sponsor – Rillet, Fidelity Private Shares, and Mercury(00:05:27) The new economics of AI pricing(00:07:51) When variable costs replace software margins(00:10:30) The fall of 80% SaaS margins(00:13:23) From premium feature to table stakes(00:15:07) Sponsor – RightRev, Tipalti, and Aleph(00:19:12) Spotting a feature before it becomes a commodity(00:23:31) The real cost of switching and why stickiness matters(00:27:46) The rise of AI white labeling(00:30:03) Outcome-based pricing — altruism or strategy?(00:34:22) Rewarding throughput and avoiding “tollbooth” pricing(00:36:29) Measuring usage and why telemetry matters(00:40:49) What makes a value exchange credible(00:44:14) Cost avoidance vs. revenue gain(00:46:02) The stages of pricing maturity(00:49:49) Why startups see what big companies can't(00:52:09) When hype meets hard costs in AI(00:55:17) When customers refuse to leave on-prem(01:03:29) Credits and Sign-Off—SPONSORS:Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metricsFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run#RunTheNumbersPodcast #PricingStrategy #SaaSModels #AIPricing #B2BRevenue This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode, CJ sits down with Brandon Sullivan, CFO at 2X, to unpack one of the most enduring tensions in business — the uneasy relationship between finance and marketing. From the myth of clean ROI to the chaos of martech spend, Brandon explains why measuring marketing impact is far harder than most CFOs think, and how spreadsheet logic can lead to bad decisions. He shares what it's like to run finance inside a 1,200-person marketing org, why cutting too deep in downturns can backfire, and what it takes to actually bridge the gap between teams that speak different languages. Along the way, he reveals lessons from scaling 2X across time zones, building global reporting rhythms, and redefining how finance and marketing can finally pull in the same direction.—LINKS:Brandon Sullivan on LinkedIn: https://www.linkedin.com/in/brandonsullivan2x/2X: https://2x.marketing/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:From Facebook's Hypergrowth to Daffy's Disruption: A CFO's Playbook for Saying Yes—TIMESTAMPS:(00:00:00) Preview and Intro(00:02:28) Sponsor – Aleph | Rillet | Fidelity Private Shares(00:05:55) Behind Enemy Lines: Finance Meets Marketing(00:07:00) Why CFOs and CMOs Clash(00:08:12) The Myth of Marketing ROI(00:10:19) Why Marketing Is So Hard to Measure(00:11:23) The Single Source of Truth Problem(00:15:29) Sponsor – Mercury | RightRev | Tipalti(00:19:35) The Three Buckets of Marketing Spend(00:21:26) The Long-Term Cost of Cutting Program Spend(00:23:27) How AI and ChatGPT Are Changing Marketing Attribution(00:25:43) Building a Modern Finance Team(00:27:55) The First-Time CFO Learning Curve(00:31:05) From Solo Operator to Scaled Finance Org(00:32:41) Why Weekly Reporting Beats Monthly Reviews(00:40:10) Working with Private Equity Partners(00:43:43) The Founding Story of 2X(00:48:12) Running a Global Team Across Time Zones(00:54:00) Long-Ass Lightning Round(00:57:00) Advice to Younger Self(00:58:58) Finance Stack and Craziest Expense Story(00:59:58) Credits and Sign-Off—SPONSORS:Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metricsFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.#RunTheNumbersPodcast #FinanceVsMarketing #CFOInsights #MarketingROI #BusinessStrategy This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Check out Mostly Growth and get episodes early. Available on all platforms.* YouTube* Spotify* AppleIn this episode of Mostly Growth, CJ Gustafson, Kyle Poyar, and Ben Hillman dive into the question on everyone's mind: are we in an AI bubble? What starts as a lighthearted riff on the U.S. Postal Service launching a podcast quickly spirals into a sharp, funny breakdown of today's AI hype cycle — from Nvidia, OpenAI, and AMD trading money and GPUs in a trillion-dollar feedback loop, to startups burning cash chasing “AI-powered” everything. The trio share real examples of when AI helps and when it backfires (including one newsletter that totally tanked), debate whether companies are over-optimizing for automation, and laugh through the absurdity of the hype while grounding it in practical insights on product, finance, and growth.Timestamps:00:00 Preview and Intro00:14 Are We in an AI Bubble?00:44 The AI Feedback Loop: Nvidia, OpenAI, and AMD01:00 Perplexity, We Caught You (Again)02:18 The USPS Podcast and the End of Original Ideas04:24 How the Team Actually Uses AI at Work06:07 CJ's DIY Dunning Saga08:38 When Automation Goes Too Far10:49 The Perplexity Gaslight Moment13:27 AI vs. AI: Outsmarting Resume Screeners16:09 What Recruiters Really Think of AI Resumes17:17 The Chief of Staff Hiring Story19:15 Is AI Adoption Already Slowing Down?22:42 The “Crossing the Chasm” Moment for AI Tools26:22 Bundling AI Like Streaming Services28:49 Everyone's Paying Everyone: The Circular AI Economy31:15 Betting Big on AGI and Data Centers34:09 The Margin: AI Erotica and Peak Absurdity35:23 OpenAI's Token Leaderboard and Other Blunders41:43 What Kyle Tried This Week: Building an AI Agent44:52 Wrap-Up and OutroEpisodes Referenced:5,762 Job Applications. Zero Offers.Episodes Referenced:5,762 Job Applications. Zero Offers.Why Only 2% of Startups Make ItThe War for Talent is just getting started | Joe FloydLinks:https://usps-mailin-it.simplecast.com/https://i.imgflip.com/a92oy5.jpghttps://tabs.inc/webinar/tabs-agenthttps://www.nytimes.com/2025/10/07/business/ai-chatbot-prompts-resumes.html?_bhlid=1b5906cdc6781a738a150d9c32f846ebf11fc318https://substack.com/home/post/p-175615945https://ramp.com/data/ai-index?utm_source=econlab.substack.comhttps://medium.com/@samuelvandeth/crossing-the-chasm-162802d1cf27https://x.com/TrungTPhan/status/1922669292929024017/photo/1https://x.com/zerohedge/status/1977902195472322620?s=42https://topline.beehiiv.com/p/the-era-of-haves-and-have-notshttps://www.bbc.com/news/articles/cpd2qv58yl5ohttps://www.linkedin.com/posts/cj-gustafson-13140948_imagine-getting-called-into-your-cfos-office-activity-7381681514532458496-NOqa/https://fortune.com/2025/10/01/red-lobster-ceo-damola-adamolekun-comeback-plan-bankruptcy/https://fortune.com/2024/11/13/red-lobster-ceo-damola-adamolekun-says-endless-shrimp-is-never-coming-back/#https://www.relay.app/Today's podcast is brought to you by MetronomeYou just launched your new AI product. The new pricing page looks great. But behind it? Last-minute glue code, messy spreadsheets, and running ad-hoc queries to figure out what to bill. Customers get invoices they can't understand. Engineers are chasing billing bugs. Finance can't close the books.With Metronome, you hand it all off to the real-time billing infrastructure that just works—reliable, flexible, and built to grow with you. We turn raw usage events into accurate invoices, give customers bills they actually understand, and keep every team in sync in real time.Whether you're launching usage-based pricing, managing enterprise contracts, or rolling out new AI services, Metronome does the heavy lifting so you can focus on your product, not your billing.That's why some of the fastest-growing companies in the world, like OpenAI and Anthropic, run their billing on Metronome.Visit metronome.com to learn more. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ Gustafson sits down with Ivan Makarov, Operating Partner at Andreessen Horowitz and former VP of Finance at Webflow, to explore what it takes to build a finance function from scratch inside a fast-growing startup. Ivan shares lessons from the trenches—how to decide between outsourcing and hiring in-house, what makes a great first finance hire, and why early-stage companies often run out of cash before they run out of ideas. He also dives into fundraising pitfalls, audit readiness, and the tools that make up a modern finance stack. Beyond the spreadsheets, Ivan opens up about the shift from operator to venture partner, the value of helping founders avoid his past mistakes, and what makes an offsite actually work.—LINKS:Ivan Makarov on LinkedIn: https://www.linkedin.com/in/ivansmakarov/Andreessen Horowitz: https://a16z.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:Webflow's VP Finance Ivan Makarov on Understanding Startup Equity:Portfolio Operations: This Is What You Actually Have To Do To Make Sure a Company Is Successful:Brex COO/CFO Michael Tannenbaum on Taking Risks996 Culture, Exploding AI Bills & SaaS Chaos—TIMESTAMPS:(00:00:00) Preview, Intro(00:01:18) Meet Ivan Makarov of Andreessen Horowitz & Episode Setup(00:02:39) Sponsor – Tipalti | Aleph | Rillet(00:06:51) From Webflow to Andreessen: Becoming an Operating Partner(00:09:19) When and Why Founders Hire Their First Finance Leader(00:12:52) Hiring Early in Complex or Regulated Industries(00:13:58) The First Finance Hire in 2025 vs. 2015(00:15:46) Sponsor – Fidelity Private Shares | Mercury | RightRev(00:19:02) The Many Hats of Finance Leaders & The Rise of RevOps(00:24:55) What Founders Look For: Startup DNA and Work Ethic(00:26:05) Grind Culture, Return to Office, and New Expectations(00:28:20) From BizOps to RevOps: How Finance Roles Are Evolving(00:31:57) The First 12 Months of a Finance Leader's Playbook(00:35:05) Choosing Audit Partners and Avoiding Hidden Costs(00:36:32) Why Startups Really Fail — Running Out of Cash(00:39:16) Cash Controls, Banking Diversification, and Fraud Prevention(00:43:48) Fundraising Red Flags: Metrics, Definitions, and Diligence(00:47:50) 409A Valuations, Equity Clarity & Candidate Questions(00:50:09) The Modern Finance Tech Stack & Gen 3 Tools(00:55:05) AI's Impact: Replacing Labor, Not People(01:00:00) Offsites, Team Building & The Future of Finance Leadership(01:02:28) Wrapping Up: Reflections, Gratitude & Closing Credits—SPONSORS:Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metricsFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.#RunTheNumbersPodcast #StartupFinance #VentureCapital #CFOInsights #Leadership This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode, CJ sits down with Joe Floyd, General Partner at Emergence Capital, for a candid conversation about the venture landscape reshaped by AI. They unpack how acqui-hires are rewriting the social contract between founders and investors, why AI engineers are commanding “boy band money,” and how SaaS playbooks are being torn up and rebuilt in real time. Joe explains the economics of AI-native startups — from circular capital flows to model-provider costs — and explores whether the next trillion-dollar private company could come from this new wave. Along the way, they discuss valuation frenzy, headcount discipline, and why curiosity might be the most valuable skill in tech today.—LINKS:Joe Floyd on LinkedIn: https://www.linkedin.com/in/joefloyd/HarbourVest Partners: https://www.emcap.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:Why Fundraising Has Slowed Down: Insights from Emergence Capital's Benchmarking Report: From Credit Karma to Notion: CFO Rama Katkar on Leading Finance Through Every Growth Stage:—TIMESTAMPS:(00:00:00) Preview and Intro(00:00:54) Opening and Episode Overview(00:02:53) Sponsor – RightRev | Tipalti | Aleph(00:07:07) Back to the Office and Startup Pace in San Francisco(00:08:40) AI Tooling Experiments and the Risk of Short-Term Hype(00:10:19) Building Stickier AI Products and Competing in Crowded Markets(00:12:27) SaaS Moats, Product-Market Fit, and the AI Shift(00:14:00) How Productivity Platforms Use AI To Stay Sticky(00:15:58) Continuous Authentication and the Next Wave of Security Tech(00:16:36) Sponsor – Rillet | Fidelity Private Shares | Mercury(00:19:54) Acqui-Hires, the Social Contract, and the War for AI Talent(00:22:42) Stock-Based Comp and the Economics of Attracting Engineers(00:24:39) The New Go-to-Market Playbook and Curiosity as a Superpower(00:27:59) AI's Impact on Sales, Forecasting, and Buyer Behavior(00:29:11) Coding Agents, Headcount Reduction, and the Future of Engineering(00:32:21) Building Defensible IP and Competing in the LLM Ecosystem(00:34:34) AI ROI, Payback Periods, and the Search for Efficiency(00:37:17) Valuations, Fund Cycles, and the Venture Market Reset(00:40:20) The Circular Flow of AI Capital and Infrastructure Overbuild(00:45:37) AI Pricing Models, Platform Wars, and Open Source Futures(00:50:02) The Race to the First $1 Trillion Private Company(00:51:09) Credits and Outro—SPONSORS:Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics#RunTheNumbersPodcast #VentureCapital #ArtificialIntelligence #StartupStrategy #FutureOfWork This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Check out Mostly Growth and get episodes early. Available on all platforms.* YouTube* Spotify* AppleConference season is back, and CJ and Kyle are swapping stories from the stage—how to nail a keynote, whether conferences are worth the money, and why your walkout song matters more than you think. From there, they dig into a new a16z report revealing where AI startups are actually spending their dollars, and CJ shares results from his summer survey showing that CFOs talk a big game about measuring AI ROI—but nobody knows how to do it. The crew also unpacks how SaaS companies like Slack are bundling AI into their products and hiking prices, before spiraling into a late-night “potentially reliable” rabbit hole featuring a Soviet pole vaulter, beat-and-raise forecasting, and J. Edgar Hoover. They close with lessons on pricing in the real world (yes, Amsterdam's architecture is involved) and one experiment CJ tried this week.Timestamps:00:00 Preview and Intro02:03 Walkout Songs & Kicking Off Conference Season04:12 Sponsored Segment — Metronome05:16 How To Give a Great Keynote and Not Bore the Room11:16 Are Conferences Worth the Money16:02 What AI Companies Are Actually Paying For — The a16z Report21:56 Summer Survey Results: The Elusive ROI of AI23:56 Why No One Knows How To Measure ROI on AI29:38 SaaS Companies Forcing AI — Bundling, Pricing, and Pushback35:32 A Potentially Reliable Thing I Read at 2 AM36:02 Soviet Pole Vaulter, Beat-and-Raise Forecasting & Hoover's Borders41:02 Pricing in the Real World — Lessons from Amsterdam's Skinny Houses44:37 Something I Tried This Week — FixyerEpisodes Referenced: ⁠Are You Bad at LinkedIn… or Is the Algorithm Lying?⁠⁠Why Founders Are Posting Sad Dinners⁠Links:⁠⁠⁠https://www.getmobly.com/⁠⁠https://a16z.com/the-ai-application-spending-report-where-startup-dollars-really-go/⁠⁠https://www.growthunhinged.com/p/how-to-nail-your-next-big-talk⁠⁠https://www.leahtharin.com/p/113-vincent-pierri-how-to-deal-with⁠⁠https://www.freepik.com/⁠⁠https://cluely.com/⁠⁠https://www.mostlymetrics.com/p/it-was-the-summer-of-25⁠⁠https://www.crescendo.ai/⁠⁠https://www.linkedin.com/posts/justintropic_slack-just-raised-prices-125-by-forcing-activity-7379132597009870848-XI6N/⁠⁠https://www.mostlymetrics.com/p/what-a-soviet-era-pole-vaulter-can-teach-us-about-beating-and-raising⁠⁠https://www.nytimes.com/1972/05/03/archives/j-edgar-hoover-made-the-fbi-formidable-with-politics-publicity-and.html⁠⁠https://www.reddit.com/r/todayilearned/comments/73vh2j/til_that_the_dutch_government_once_enforced_a_tax/⁠⁠https://www.clearspaceliving.com/blog/why-dutch-stairs-are-so-steep/⁠⁠https://mjwrightnz.wordpress.com/2012/10/28/amsterdams-taxing-narrow-houses/⁠⁠https://www.fyxer.com/Today's podcast is brought to you by MetronomeYou just launched your new AI product. The new pricing page looks great. But behind it? Last-minute glue code, messy spreadsheets, and running ad-hoc queries to figure out what to bill. Customers get invoices they can't understand. Engineers are chasing billing bugs. Finance can't close the books.With Metronome, you hand it all off to the real-time billing infrastructure that just works—reliable, flexible, and built to grow with you. We turn raw usage events into accurate invoices, give customers bills they actually understand, and keep every team in sync in real time.Whether you're launching usage-based pricing, managing enterprise contracts, or rolling out new AI services, Metronome does the heavy lifting so you can focus on your product, not your billing.That's why some of the fastest-growing companies in the world, like OpenAI and Anthropic, run their billing on Metronome.Visit metronome.com to learn more. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Private markets are swelling, public markets are shrinking, and the line between the two has never been blurrier. In this episode, CJ sits down with Scott Voss, Managing Partner at HarbourVest, to make sense of what's happening across venture, private equity, credit, and secondaries. Scott explains why companies like SpaceX and OpenAI are now valued alongside public giants, how the surge in take-privates is reshaping corporate strategy, and what happens when the quarterly earnings pressure disappears. They dive into the rise of GP-led deals, the evolving role of private credit as the “third voice in the room,” and why liquidity—not scarcity—will define this cycle. Scott also breaks down the growing appeal of evergreen and permanent capital structures, plus what AI mega-deals signal about the next phase of private investing.—LINKS:Scott Voss on LinkedIn: https://www.linkedin.com/in/scott-voss-b91b94/HarbourVest Partners: https://www.harbourvest.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:Secondaries, Continuation Vehicles, and Sidecar Funds: Private Equity with HarbourVest's Scott Voss -—TIMESTAMPS:(00:00:00) Preview and Intro(00:02:49) Sponsor – Mercury | RightRev | Tipalti(00:06:43) Opening Conversation(00:07:23) The Blurring Line Between Public and Private(00:09:36) The Rise of Mega Venture(00:11:20) The First $10 Trillion Company(00:12:28) The Shrinking Public Markets(00:13:09) Take-Private Playbook(00:14:04) Why Companies Go Private(00:16:00) Sponsor – Aleph | Rillet | Fidelity Private Shares(00:19:21) Efficiency and Exits(00:23:15) Liquidity in Private Markets(00:24:01) Secondaries and GP-Led Deals(00:27:14) Yale and the Secondary Market(00:29:09) Innovation and the Rise of GP-to-GP Trades(00:30:16) Liquidity Cycles and Interest Rates(00:33:18) The Third Voice in the Room – Private Credit(00:34:44) Private Credit and GP-Led Deals(00:36:02) Interest Rates and Deal Spreads(00:37:15) The Major Players in Private Credit(00:38:09) Regulation and Risk(00:39:25) Private Credit vs. Traditional Lending(00:40:33) Evergreen and Permanent Capital(00:45:57) Expanding Access to Private Markets(00:47:03) Understanding the Cap Table(00:47:44) AI Deals and Consolidation(00:50:00) The Evolution of AI and Blockchain(00:53:20) Funding Innovation and Risk(00:55:28) Lessons From Investing(00:55:39) Nostalgia and Life Phases(00:57:06) Nostalgia and the 1990s(00:59:21) Learn, Earn, and Return(01:00:45) Talking Nostalgia at Dinners(01:01:27) Summer Surfing(01:02:25) Wrap-Up and Closing—SPONSORS:Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics#RunTheNumbersPodcast #PrivateMarkets #VentureCapital #TakePrivate #FinanceLeadership This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com