Run The Numbers

In this episode of Run the Numbers, CJ sits down with Todd McElhatton, CFO of Zuora, for a deep cut on pricing, packaging, and value in the age of AI. They dig into how companies are figuring out whether to charge for AI at all, why token-based budgets are starting to sit alongside headcount budgets, and why AI may be increasing — not decreasing — the value of deep expertise.—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/metricsAbacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made. Go to abacum.ai/mostly-metrics.RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjFidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let's be honest, who doesn't need a little help now and then), then you're in for a pleasant surprise with Fidelity. If you stay investor ready, you don't have to get investor ready. Check out www.fidelityprivateshares.comRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjCloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to www.cloudcapital.coEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: linkedin.com/in/todd-mcelhatton-2140761Company: www.zuora.comCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Intro1:15 Meet Todd2:24 Debating Price7:33 Is Software "Going Headless"?9:18 Is AI Increasing the Value of Experts9:58 Hiring Specialists vs. Generalists16:49 Rethinking the Budget Envelope26:56 Time to Value31:20 Forward-Deployed Engineers35:20 Parallels Between On-Prem-to-Cloud36:10 Rethinking Strategy37:07 Avoiding the Sunk Cost Trap38:58 The Art of Pivoting40:12 VMware41:31 Experimenting With AI42:33 What Private Boards Bring43:13 Short-Term Pain43:45 One-Way Doors vs. Two-Way Doors44:57Long-Ass Lightning Round45:04 Biggest Career Mistake45:36 Advice45:56 Finance Tech Stack46:43 The Craziest Thing Expense#RunTheNumbersPodcast #AIforCFOs #FinanceLeadership #Zuora #GoingPrivate

CJ sits down with Lauren Dillard, CFO of LiveRamp, whose path to the CFO seat ran through investor relations, communications, and even a year as interim CMO. They dig into why storytelling and influence matter as much as technical finance chops, how LiveRamp tore down and rebuilt its entire commercial model — collapsing 25+ usage metrics into 5 and inventing the "token" along the way.—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/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/lauren-russi-dillard-25502424/Company: https://www.liveramp.comCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Cold Open1:18 Intro1:29 Meet Lauren Dillard4:48 Lauren's Path to CFO5:06 The "Wrong" Career Move7:48 Why Storytelling Matters9:41 Turning the Answer Into Action10:33 People Plus AI14:50 Pricing Is a Strategy Exercise16:43 Rebuilding a Commercial Model22:29 Simplifying Quote-to-Cash23:29 Where the "Token" Came From28:48 Selling a New Pricing Model29:27 Balancing New Logos30:17 Upmarket or Downmarket?34:17 Where Finance and HR Disagree36:07 The Biggest Mistake38:23 Will It Make the Boat Go Faster?42:27 Lessons from the NBA44:25 Lauren's Biggest Misstep46:27 Finance Tech Stack47:42 Craziest Expense#RunTheNumbersPodcast #AIforCFOs #FinanceLeadership #MasterworksArt #ContextEngineering

Nscale just filed its S-1 to go public on the NYSE — and it might be the wildest IPO filing of the year. This UK-based "NeoCloud" is only 2 years old, is gross margin negative, started life as a crypto miner, and has somehow locked up over $100 billion in contracted value from Anthropic and Microsoft. CJ breaks down the entire S-1 line by line: what a NeoCloud actually is, how Nscale's "power to token" strategy works, why Nvidia shows up as its supplier, investor, guarantor, AND customer, and whether this is a durable business or a well-timed arbitrage on the AI compute shortage.—SPONSORS:Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/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/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCompany: https://www.nscale.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Cold Open0:53 Intro: Nscale Files to Go Public2:40 WTF Is a NeoCloud?4:11 The 5 Layers of the AI Stack5:55 Landlord vs. Hotel: Nscale's Two Businesses7:21 How Take-or-Pay Contracts Work8:28 Sponsor Break11:43 Breaking Down the Financials15:37 What's a Contract Actually Worth?18:45 Is This Just Nvidia Vendor Financing?20:58 Sponsor Break22:54 Medium-Term Arbitrage or Durable Company?24:30 5 Potential Red Flags27:08 How Does the CEO Get Paid?28:04 Who's on the Board?28:26 Is This the CoreWeave of the UK?31:09 Miscellaneous Filing Oddities33:31 Final Take#Nscale #IPO #NeoCloud #S1Breakdown #AIInfrastructure

In today's Run the Numbers, CJ sits down with Blake Saunders, founder and managing director at Core Advisors (an investment bank focused on media) and founder of The Joint, to go deep on how media companies actually make money — and how that's changing fast.If you're anywhere near advertising, media, or content monetization, this one's a masterclass.—SPONSORS:Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/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/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: linkedin.com/in/blakesaundersCompany: https://coreadvs.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Cold Open and Intro1:17 Welcome Back: Meet Blake Saunders3:11 What Does "Media" Even Mean Today?3:24 AI and LLMs6:13 How Media Companies Make Money7:32 Subscriptions vs. Ads vs. Events8:54 Why Events Are the Riskiest Ad Dollar9:48 B2B vs. B2C14:25 Why Advertising Gets Such a Bad Rap17:58 The Hulu Paradox20:50 Built to Hold vs. Built to Sell27:10 Content Decay and the Monetization Mismatch29:08 Are IP Libraries Becoming Valuable34:39 How Big-Name Podcast Deals Get Structured37:50 Bundling, Unbundling, and Subscription Fatigue39:08 The Bending Spoons Trade40:20 Inside a Private Equity Value Creation Plan41:56 The Content-to-Commerce Playbook44:50 How Narrative-Driven Is Media M&A?46:49 7 Moments a Deal Feels Dead49:00 Farewell

CJ sits down with multi-time CFO Rick Smith, founder of Bonfire Advisory and author of Six Months to the Sale, to break down what actually happens when you sell a company. They cover why buyers value some businesses on ARR and others on EBITDA (and why being slightly profitable can hurt you), how to negotiate banker fees, what buyers find when they dig into your balance sheet, and why every cap table Rick inherits is wrong.—SPONSORS:RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: linkedin.com/in/rick-smith-906939Company: https://www.linkedin.com/company/bonfire-advisoryCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:1:21 Meet Rick Smith and "Six Months to the Sale"2:44 Why Teach M&A Through Fiction4:26 CEO/CFO Tension7:08 Botching the Announcement8:15 How Staff Really React9:18 When Personal Life Collides With a Deal13:50 ARR vs. EBITDA17:58 What to Optimize Before a Sale18:50 Churn and Contract Renewal20:43 Strategics vs. PE27:46 Investment Banker Fee Structures29:09 What's Negotiable29:56 The Realtor Problem34:53 Big 4 vs. Regional Firms for Audit and QoE35:47 Negotiating Accounting Fees37:47 Deferred Revenue41:23 Warrants, Options, and Carta Cleanup44:02 QSBS: What CFOs Need to Know45:28 Quality of Earnings: Who Pays and Why47:44 What a QoE Actually Digs Into51:22 Why Deal Momentum Is So Hard to Stop53:47 The Waterfall58:19 Who Keeps Their Job61:31 Why Selling CFOs Feel Intimidated62:56 Prospect Theory65:28 Where to Find the Book#RunTheNumbersPodcast #MandA #CFOLife #SellingACompany #QualityOfEarnings

CJ Gustafson sits down with Nigel Glenday, CFO and COO of Masterworks, to talk about how AI is actually changing day-to-day finance work. They cover why context matters more than model choice, how Nigel runs a dozen Claude Code terminal sessions at once, and how his team solved a 300,000 K-1 problem with Python instead of a $300K tool. Plus: a detour into the 2026 art market and what securitizing fine art teaches you about scarcity and pricing power.—SPONSORS:Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/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/metricsEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: linkedin.com/in/nglendayCompany: https://www.masterworks.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com— RELATED EPISODES:Nigel's Previous Episode: ⁠⁠⁠https://www.youtube.com/watch?v=zfmqwIzM0P4&t=9s⁠⁠⁠ — TIMESTAMPS: 2:04 The Dinner Story: AI as Leverage 7:27 AI and the Value of Human-Curated Creativity 12:16 Why Context Beats Intelligence 14:11 What "Context" Actually Means for AI 16:50 Building a Knowledge Map18:50 Why CFOs Are Uniquely Positioned to Encode Context 21:36 Making Data Cheap to Access28:55 Claude Code Over the Web App 30:49 Building "The A-Team"35:24 Solving 300,000 K-1s with AI and Python42:26 Asking Better Questions Segment 42:50 Adopting Campfire44:20 When Human Writing Beats AI#RunTheNumbersPodcast #AIforCFOs #FinanceLeadership #MasterworksArt #ContextEngineering

How did Oura turn a tiny piece of wearable hardware into a $1.4 billion business? CJ breaks down the numbers behind Oura's IPO filing and the surprisingly powerful business model hiding behind the ring.—SPONSORS:Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Oura Files S12:24 Key Revenue Stats3:35 Revenue Per Ring4:14 Gross Margin Breakdown5:31 The Weird $924M "Net Loss"6:11 Adjusted EBITDA and Cash Position7:20 Headcount and Bankers11:01 What Oura Actually Does13:46 Go-to-Market Channels15:57 Why Oura Rejects the "Fitness Tracker" Label16:49 Who's Actually Buying It21:26 Global Penetration Is Still Low21:54 The $84M Battery Problem22:56 Aggressive Growth Spend24:16 Samsung's Patent Complaint25:00 The Sleep Accuracy Class Action25:17 Former CEO Lawsuit25:52 Customer Concentration Risk26:31 Supply Chain and Tariff Exposure27:07 Clean Governance, No Material Weaknesses27:20 The Cap Table27:44 Oura's Massive Stock Buybacks29:29 The RSU Vesting Mechanics30:34 Tax Withholding on Settlement31:07 Valuation: $16B at 11x Revenue31:34 Who Do You Comp Oura To32:34 Miscellaneous Filing Details33:14 Final Take

In this episode of Run the Numbers, CJ sits down with Matt Hedberg, a sell-side equity analyst at RBC who has covered software for more than 20 years. They break down how AI compares to the cloud transition, why traditional software moats are changing, what separates management teams that will actually capitalize on AI, and why cash, customer relationships, data, and technical leadership matter more than ever.—SPONSORS:Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjEY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/matt-hedberg/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RBC Capital Markets: This content is based on information available at the time it was recorded, and is for informational purposes only. It is not an offer to buy or sell, or a solicitation, and no recommendations are implied. It is outside the scope of this communication, to consider whether it is suitable for you, and your financial objectives. For Required Conflicts Disclosures, see: https://www.rbccm.com/GLDisclosure/PublicWeb/DisclosureLookup.aspx?entityId=1. For Disclaimer, see: https:/www.rbccm.com/en/policies-disclaimers.page.

In this episode of Run the Numbers, CJ sits down with leadership coach and former Akamai executive Andy Ellis. They break down why being indispensable can actually hurt your career, why managers shouldn't automatically replace someone who leaves, how hero-villain thinking leads to bad decisions, and what great delegation and leadership actually look like.—SPONSORS:Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsEY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/csoandy/Company: https://www.csoandy.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Jero and Villain Stories1:43 Welcome to Run the Numbers2:53 Andy's Book: 1% Leadership7:44 Rule 1: Don't Replace People Immediately14:04 Rule 2: Don't Become Indispensable16:02 How Andy Learned to Speak Finance22:35 Rule 3: Don't Tell Yourself Hero/Villain Stories26:59 The 5K Race Mindset Shift31:01 Rule 4: Don't Overspecify Delegation35:59 Rule 5: Don't Obsess Over Your Strengths38:23 The Six Leadership Disciplines43:45 The Vendor Rebuff Email47:45 Why Leaders Avoid Saying No50:28 Story: The Guinness Bartender Promotion53:52 When Metrics Get Gamed54:11 Asking Better Questions Segment59:07 Where to Get the Book

In this episode of Run the Numbers, CJ sits down with Jay Ritter. They break down what Apple, Nvidia, the dot-com boom, and today's AI giants can teach us about IPOs, why companies leave money on the table on day one, why firms stay private longer, and what the data actually says about long-term IPO performance.—SPONSORS:Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjEY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/jay-ritter-1323861/Company: https://www.ufl.edu/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro3:10 Meet Jay Ritter, Mr. IPO4:02 The Original 1983 Question5:08 PCs, Internet, and AI Compared9:36 Network Effects14:46 Sitzfleisch: Outlasting the Field16:10 Where Have All the IPOs Gone23:29 IPOs as Relationship-Building26:31 Why Investors Tolerate Founder Control29:16 Dual-Class Stock's Origins30:21 How Jay's Thinking Evolved31:36 Why Boards Don't Get Angry34:39 Banks' Real Client: Institutions37:08 Book Building38:56 Why Direct Listings Haven't Taken Over39:57 What Goldman Is Really Selling41:57 Sentiment vs. Long-Term Performance43:13 Does Staying Private Help Society49:35 Asking Better Questions with EY52:12 Are Markets Efficient

CJ sits down with Rebecca Schwartz of Tabs, Fred Havemeyer of Fleet AI, and Rahul Rekhi of Rogo for a live conversation about what it actually takes to build an AI-native company. —SPONSORS:RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnEY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNhttps://www.tabs.com/https://fleetai.com/https://www.rogo.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro1:16 Welcome to Run the Numbers3:17 Meet the Panel: Rebecca, Fred, Rahul9:52 How Rogo Found PMF13:47 How Tabs Found PMF14:51 Growth Rates: Headcount and Revenue16:23 The Real Hiring Constraint17:21 What "Forward Deployed" Actually Means18:53 What's Blocking AI Adoption Now20:19 How Sales Hiring Has Changed24:34 How Go-to-Market Has Changed25:28 Pricing Models: Then vs. Now28:18 Tabs' Pricing Evolution29:20 What the Finance Team Looks Like31:00 How Far You Can Push Outsourced Accounting32:43 Managing AI Gross Margins35:07 The North Star Metric for AI Companies37:02 Token Spend vs. Per-Seat Pricing39:34 Asking Better Questions: What Counts as ARR41:38 Biggest Bug in Cash to Collections43:05 Closing Advice for Founders

In this episode of Run the Numbers, CJ sits down with Wisam Hirzalla, Head of Product at Stripe Billing, to trace the full journey of a dollar—from product packaging and pricing through quoting, contracts, billing, tax, collections, and revenue recognition.—SPONSORS:Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsEY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/wisam-hirzalla-9b20a91/Company: https://stripe.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 What Drives Billing Downstream1:41 Welcome to Run the Numbers2:37 Wisam's Path to "Queen of Billing"4:55 What Head of Billing at Stripe Entails5:45 Defining Quote-to-Cash7:50 Layer 1: Pricing and Packaging Mistakes14:46 Pricing Models Rising Because of AI18:11 Layer 2: Inside a Quote19:27 Why Enterprise Deals Get So Messy24:38 Layer 3: Contracting27:21 Layer 4: Billing30:15 Why Usage-Based Billing Is So Complex34:51 Tokens as a Pricing Unit36:57 Billing's Move Out of the ERP39:53 Layer 5: Provisioning and Entitlements43:36 Layer 6: Tax44:27 Layer 7: Getting Paid48:18 Layer 8: RevRec50:52 When Billing Stopped Being Back Office51:47 Asking Better Questions Segment52:28 Will AI Replace Finance Jobs

Front CFO & COO Meredith Finn joins CJ to explain why finance leaders are taking on more of the operator's job. They break down the CFO-COO dual mandate, how Front funds new bets inside a mature SaaS business, why AI requires more coordination than simply handing everyone new tools, and how finance teams should think about the growing cost of AI.—SPONSORS:Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/meredithfinn1/Company: https://front.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Adam Swiecicki - CFO of Ripplinghttps://youtu.be/JyGJVpmZNacAurélien Nolf - CFO of Navanhttps://youtu.be/siwzJSRXAvY—TIMESTAMPS:0:00 The CFO/COO Dual Mandate1:45 Welcome to Run the Numbers2:52 Front's In-House Podcast Studio3:41 Meredith's Investment Thesis on Front7:21 The "Portfolio Career" Analogy8:35 What She Had to Unlearn as an Operator13:13 Books on Strategy vs. Execution16:17 When a CFO Should Also Be COO18:27 What the COO Hat Actually Covers20:20 Where the Two Roles Conflict25:42 Budgeting for AI Token Costs29:16 Using Internal Usage as a Benchmark35:40 Funding a Series A Bet Inside a Series D Company38:04 Sizing Bets: Core, Adjacent, Moonshot40:04 The Secret to Re-Accelerating Growth41:46 Going Deeper, Not Wider43:18 What the Pricing Overhaul Taught Her47:30 Why Customer P&L Matters50:11 Lightning Round Begins51:32 Advice to Her Younger Self52:33 Front's Finance Tool Stack53:21 Craziest Expense Ever#RunTheNumbersPodcast #CFOLife #FinanceLeadership #AIinFinance #SaaSGrowth

In this episode of Run the Numbers, CJ Gustafson sits down with Xero CFO Claire Bramley to discuss how the CFO role is expanding beyond finance into strategy, operations, transformation, and technology. Claire also shares how she builds teams around her weaknesses, what small businesses actually want from AI, and why she views diversity as a business performance decision.—SPONSORS:Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/claire-bramley-133b7174/Company: https://www.xero.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro3:00 Xero and CJ's History With It4:12 Xero's Size and Scale Today5:10 The Expanding CFO Role7:06 Hiring Experts You're Not8:47 Imposter Syndrome11:00 Getting Better at Asking Questions15:04 Asking the "Stupid Question"16:21 Finance as the Corporate Junk Drawer17:48 The Trial Period Idea18:24 Tripwires: Leading Indicators for CFOs25:35 AI Hype vs. Main Street Reality26:44 What Small Business Owners Actually Want28:45 What Big Corps Underestimate31:10 Trust as a Competitive Moat33:45 Why the Line Is Thinner for Small Biz35:12 AI Inside Claire's Finance Team37:23 AI for Investor Relations39:28 Diversity as Capital Allocation42:07 A Decision Diversity Changed44:45 Lightning Round Begins46:06 Advice to Her Younger Self48:49 Craziest Expense Ever#RunTheNumbersPodcast #CFOLife #FinanceLeadership #AIinFinance #WomenInFinance

On this episode of Run the Numbers, CJ and Ben trace corporate private jets from Sam Walton's scrappy two-seater to Alex Karp's $17 million jet bill. They break down when flying private actually makes business sense, how jets hit the balance sheet, the tax and accounting implications, what companies disclose to investors, and when executive travel crosses the line from productivity tool to corporate excess.—SPONSORS:Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Jersey Mike's IPO: The $4.2B Sandwich Machinehttps://youtu.be/ZL6AbqHI-0g—TIMESTAMPS:0:00 Fly Like a G60:29 $17M on jets: Alex Karp guess1:16 Sam Walton starts it all2:49 The yellow legal pads4:37 Walmart Aviation founded (1968)5:14 Piston to Bombardier jets6:51 Walmart's modern jet fleet8:13 Where it hides in SEC filings9:25 SEC Reg S-K Item 40213:37 Gulfport Energy scandal14:42 Tyco: Kozlowski & Schwartz16:57 When jets are actually useful17:55 P&L vs. balance sheet treatment18:40 PP&E and depreciation basics19:04 Off-balance-sheet leases19:28 The chartering loophole19:54 "Uber Jet" fractional ownership23:14 How activists hunt jet spend23:36 Flight registries & tail numbers24:13 Jack Sweeney vs. Elon Musk25:00 What top companies spend25:18 Walmart's fleet is #126:17 Charter vs. lease vs. own29:02 Should we care? 3 angles30:06 Angle 2: opportunity cost30:59 Angle 3: company size31:42 General Electric's shadow jet32:50 Back to Alex Karp34:02 Credits#RunTheNumbersPodcast #PrivateJets #CorporateFinance #ExecutivePerks #CFOLife

On this episode of Run the Numbers, CJ Gustafson sits down with Richard Haram, VP of Finance at RapidSOS, to unpack how finance supports a public safety AI platform that helps 911 operators and first responders act faster. They cover building AI fluency, combining FP&A with BI, monetizing vertical software, integrating acquisitions, and the leadership lessons Richard carried from entrepreneurship.—SPONSORS:Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/richardharem/Company: https://rapidsos.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro3:10 What RapidSOS does4:59 CJ's own car accident5:33 What's broken about 9116:50 Who's the actual customer7:46 How RapidSOS monetizes10:13 Sponsors — Pulley | Rillet | Maximor13:27 Too much data, too much noise16:35 Data pollution and trust18:24 The data stack early on19:25 Should BI have come sooner?20:45 The framework: questions to decisions22:43 Building a data culture23:58 Sponsors — Brex | Anrok | RightRev26:51 Bottoms-up vs. top-down AI28:42 Inspiration, not training32:24 The three-phase AI progression33:31 Founding an AV company at 835:37 Giving people room to grow38:12 Depending on heroes39:55 Working under founder personalities41:23 Do startups undervalue what they sell42:48 A price hike, zero churn43:24 Signs you're underpricing44:57 Lightning round45:03 Screwed up: refreshed data before a demo47:15 Advice to younger self47:41 Finance software stack48:37 Craziest expense: personal gas49:29 Credits

On this episode of Run the Numbers, CJ sits down with Plaid CFO Seun Sodipo. Seun explains how her team is using AI to improve speed, accuracy, and ambition; why finance leaders need both bottom-up experimentation and top-down direction; and how she approaches planning, network effects, and building a durable company.—SPONSORS:RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/seun-sodipo-1498b580/Company: https://plaid.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro2:12 What Plaid does3:53 How Plaid makes money7:04 Eight months in, not new anymore8:57 Sponsors — RightRev | Pulley | Rillet11:48 Career path: Stripe, Glossier, Plaid14:32 Evaluating durability from the outside15:36 Rising expectations and AI17:23 Top-down vs. bottoms-up AI adoption20:06 Sponsors — Maximor | Brex | Anrok23:20 Coolest AI use case: sorting physical mail25:21 How her questions have changed27:11 AI should make you think deeper27:51 Finance AI Day explained31:23 A four-month journey to usable tools32:22 How AI changed her leadership style33:19 Skills that matter more now36:22 The Objective, Strategy, Tactics framework39:56 What planning reveals about an org41:36 Sequential vs. parallel planning45:38 Measuring the value of a network47:33 What people underestimate about Plaid48:56 Lightning round48:56 Screwed up: the reversed page order49:39 Advice to younger self50:32 Finance software stack51:43 Craziest expense: the photo shoots52:20 Credits

On this special episode of Run the Numbers, CJ Gustafson revisits standout moments from past conversations with Alex Immerman, Curt Sigfstead, Daniel Kang, Adam Ante, and David Laptor. Together, their advice reveals how great CFOs earn trust, challenge founders, speak up when the data says something is wrong, and become true strategic partners without relying on the power of the purse strings.—SPONSORS:Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro3:27 Alex Immerman's favorite CFO interview question4:54 What a weak answer looks like5:26 When the hard calls actually matter6:37 Walt and Roy Disney7:36 Liked even when making unpopular calls8:43 Sponsors — Anrok | RightRev | Pulley11:35 Curt from Clio: ego in the bottom drawer13:52 CFO as supporting cast15:10 Backbone vs. ego: when to use each16:23 Daniel Kang: don't use the purse strings as power17:36 Earn the seat, don't demand it18:52 Money is one arrow, not the whole quiver20:39 Sponsors — Rillet | Maximor | Brex23:54 Adam Ante: finance people pigeonhole themselves26:46 The CFO can sit in any meeting27:30 First 90 days: listen before suggesting28:46 David Laptor: listen, observe, think, speak30:50 Build a culture where speaking up is welcomed31:51 Curt from Clio: don't come in as a know-it-all33:08 Earn trust through curiosity33:46 Beware of all-green dashboards35:28 What would CJ say to Ballmer?37:14 Parting thoughts from Ben38:00 Credits

On this episode of Run the Numbers, CJ sits down with Datadog SVP of FP&A AJ Ljubich to break down the four stages of a world-class finance team.—SPONSORS:Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/aj-ljubich-cfa-727ab912/Company: https://www.datadoghq.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro2:42 FP&A as a product team4:53 The five pillars of AJ's team6:39 How far FP&A has come7:33 How do you know you're doing a good job?10:20 FP&A as the dashboard, not the engine10:20 Sponsors — Brex | Anrok | RightRev13:18 The four-stage FP&A maturity model16:00 Can you reach all four stages at Series B?16:45 Why AJ holds weekly forecast meetings18:24 How often to actually change the forecast21:42 Sponsors — Pulley | Rillet | Maximor24:49 Single source of truth: still on the vision board26:12 AI and the self-serve data risk26:21 CAC payback over LTV to CAC29:39 Inside sales vs. enterprise payback comparison31:47 Finance as the yes, but people34:02 FP&A vs. IR: which is harder?36:14 How IR makes you a better FP&A leader37:19 Is the IR profile shifting?42:01 IPOs are branding events, not finish lines43:27 The Datadog IPO during the WeWork meltdown45:15 Career philosophy: do great work where you are49:52 Datadog didn't have a role for AJ when he started52:16 Lightning round52:24 Screwed up: forgot the currency guy54:37 Finance software stack56:16 Advice to younger self57:13 Credits

On this episode of Run the Numbers, CJ sits down with Dave McClure and Aman Verjee of Practical VC to talk about the evolution of startup investing — from the PayPal mafia and Founders Fund era to 500 Startups, YC-style scale, and today's secondary market.—SPONSORS:Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuests:https://www.linkedin.com/in/davemcclure/https://www.linkedin.com/in/aman-verjee/Company:https://practicalvc.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro3:00 Writing as a distribution strategy5:17 How Dave's blog led to Founders Fund7:24 Aman: writing at PayPal and law school9:29 PayPal: the red pen of David Sacks11:44 Sponsors — Rillet | Maximor | Brex14:59 500 Startups: the original thesis16:22 The volume strategy: more shots on goal18:44 Twilio, Lyft, Sendgrid, Credit Karma20:15 60x returns: right place, right time23:07 Sponsors — Anrok | RightRev | Pulley25:58 Accelerator ecosystem evolution28:42 500 vs. YC: scale as a weapon32:52 Globalizing the accelerator model35:04 Seed to secondaries: how it happened37:00 Scratching their own itch for liquidity38:10 The secondary market explained40:50 Types of secondaries43:29 Why would a VC sell a winner?46:07 Managing DPI as a late-stage manager47:02 The five horse framework49:15 Skipping the J curve51:44 Imperfect information as a feature55:22 Landmines: fraud, mismarked valuations57:00 VCs lie about valuations three ways57:58 Forward contracts and counterparty risk1:00:29 Credits

On this episode of Run the Numbers, CJ breaks down Cumberland Farms' IPO filing and the surprising business behind it.—SPONSORS:RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro2:57 Key metrics4:28 Europe now out-earns America5:01 $5.8B debt at 8x leverage6:20 TLDR: snacks, gas, borrowed money7:58 Fuel vs. inside: the gross profit photo finish8:58 COCO, CONCO, and OTHER explained10:57 Sponsors — Maximor | Brex | Anrok14:02 Why scale matters: four reasons16:02 The US convenience store market17:42 EVs: long the birth rate18:05 Back to the debt19:10 The sale leaseback20:24 Sponsors — RightRev | Pulley | Rillet23:26 Does the deleveraging math work?24:27 The growth thesis25:06 600–700 stores become Cumberland Farms26:16 The chicken fryer ROI27:00 Coffee and loyalty: 6M members in 13 months28:15 Red flag 1: five-for-five COSO failures28:41 Red flag 2: entire C-suite is new29:04 Red flag 3: lending to their own parent29:42 Red flag 4: Big Tobacco funds loyalty29:57 Red flag 5: foreign issuer, Cayman charter30:10 Red flag 6: one supplier is 31% of costs30:32 Red flag 7: balance sheet is stale30:45 Cap table: TDR Capital and the Issa brothers31:55 Casey's vs. ARCO33:47 Goldman got bumped34:08 Massachusetts banned the pump clip until 201534:57 No health insurance disclosure for 16K US workers35:30 Robert Swan (ex-Intel CEO) is on the board36:08 Credits

In this episode of Run the Numbers, CJ sits down with Rogo president Rahul Rekhi to unpack what AI actually changes in investment banking and finance. They dig into token economics, why adoption without ROI is a trap, how vertical AI wins, and why domain expertise still matter.—SPONSORS:Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/rahulrekhi/Company: https://www.rogo.ai/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:A CFO Explains the Stock Exchangeshttps://youtu.be/pooOE6ZNGR4A CFO Explains Marketplaceshttps://youtu.be/LpbH9GpBrSY—TIMESTAMPS:0:00 Preview and Intro2:44 Why finance was first to verticalize AI6:28 What the president title means at Rogo9:55 Sponsors — Pulley | Rillet | Maximor13:02 The problem Rogo is solving16:16 Token maxing is not transformation17:43 Why ROI is so hard to measure19:39 Sponsors — Brex | Anrok | RightRev22:37 ROI is business-unit specific24:03 Budgeting tokens like a benefits load25:00 AI incentives aren't aligned to efficiency26:26 The model broker function32:03 Not all token spend is equal37:14 Who owns AI efficiency?40:59 The forward deployed banker43:00 Domain expertise: the Interstellar analogy49:21 Lightning round49:28 Screwed up: DCF error in a live deal51:13 Will new grads have the spidey sense?53:03 Meeting Pope Francis55:04 Fact-checking jobs numbers at the White House57:39 Advice to younger self59:21 Credits

On this episode of Run the Numbers, CJ breaks down Jersey Mike's S-1 and the franchise machine behind more than $4 billion in sandwich sales. He explains how an asset-light royalty model works, why franchise economics can be so powerful, what Blackstone saw in the business, and what the filing reveals about growth, margins, and the real money behind the subs.—SPONSORS:RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Sell $4B in subs, own none of the stores0:33 Origin story: Peter Cancro buys a sub shop at 171:47 It's a royalty business2:42 Key metrics6:07 What you're actually buying6:42 The three revenue streams7:19 The franchisee's P&L10:00 Sponsors — RightRev | Pulley | Rillet13:02 Corporate P&L: 47% EBITDA margins13:33 The Blackstone math14:38 $2.1B whole business securitization15:09 Full EBITDA bridge16:00 The CEO buying back the 2%17:10 Red flag 1: Up-C structure18:11 Red flag 2: tax receivable agreement18:45 Red flag 3: controlled company governance19:05 Red flag 4: sponsor already took $500M19:29 Red flag 5: charitable donations added back20:13 Red flag 6: cheap debt maturing in 202920:52 Sponsors — Maximor | Brex | Anrok23:56 Valuation: $10–12B24:32 Peer comparison25:27 How do you underwrite $12B?25:58 Misc: quantum attack on the provolone26:28 The hidden 53rd week26:57 No drive-thru is a feature27:13 Verdict27:56 Credits#RunTheNumbersPodcast #IPO #Investing #BusinessStrategy #FinanceLeadership

What actually prepares someone to become a CFO? CJ revisits Erin Callan's short, brutal run as Lehman Brothers CFO and pulls lessons from past guests on operational reps, simple communication, fast-moving bad news, budget mistakes, and why great finance leaders can't just report the numbers, they have to shape them.—SPONSORS:Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Slacker Stuff: https://www.slackerstuff.com/Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Steve Isomhttps://youtu.be/a4lEdrgFW5EJake Kornreichhttps://youtu.be/GKo0B1w4bo4Manu Diwakarhttps://youtu.be/J0J4Rfne54EDan Betteshttps://youtu.be/b4w_OHpSNNwAlan Imbermanhttps://youtu.be/UD9lYhkfA6U—TIMESTAMPS:0:00 Erin Callan: Lehman's CFO Set up to Fail5:48 Steve Isom: broadcaster vs. team captain9:37 Be in rhythm with the business11:15 Sponsors — Anrok | RightRev | Pulley14:07 Jake Kornreich: title vs. impact18:23 Get into the room where decisions are made22:08 Sponsors — Rillet | Maximor | Brex25:23 Dan Betts: don't church it up27:11 The higher up you go, the simpler it gets29:04 Dan Betts: the many faces of EBITDA30:39 Understand what success means to them32:07 Jake Kornreich: the $5M budget bust33:04 Bad news travels fast35:01 Alan Imberman: the $100K coffee tab38:15 ROI on perks40:25 Alan Imberman: long-term vs. short-term investors43:28 Would you take the Lehman job?45:44 Credits#RunTheNumbersPodcast #CFO #FinanceLeadership #StartupGrowth #FinanceHistory

In this episode of Run the Numbers, CJ goes live from Rillet Recon with Dana Decker (VP of Finance at Opendoor), AJ Ljubich (SVP, FP&A at Datadog), and Micah Richard (Principal, AI at PwC) to unpack how finance teams are actually using AI. —SPONSORS:Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuests:https://www.linkedin.com/in/aj-ljubich-cfa-727ab912/https://www.linkedin.com/in/dana-decker/https://www.linkedin.com/in/micah-richard-64a53238/Companies:https://www.datadoghq.com/https://www.opendoor.com/https://www.pwc.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro2:27 Panel intros: AJ, Micah, Dana4:00 FP&A a year ago vs. today6:45 Opendoor: default-to-AI company7:40 Leadership being in the weeds8:30 Building a daily P&L view with Claude9:39 Sponsors — Brex | Anrok | RightRev12:38 Forecasting at Datadog: consumption model14:20 AI picks up seasonality, misses customer context15:10 Semantic layer and blessed queries16:35 Self-serve data: how far can you go?20:10 Best-in-class adoption: build over buy20:23 Sponsors — Pulley | Rillet | Maximor23:30 Does a 2-year head start matter?24:10 Build vs. buy criteria haven't changed25:10 Evaluating vendor roadmaps26:20 Procurement shifting toward build28:00 Data access controls and RBAC31:00 Token usage: haves and have-nots32:50 Encouraging tokens across the org34:40 ROI metrics haven't changed35:45 90-day advice: just start36:55 Leadership has to pull the red tape38:05 Get the data right first39:07 Credits

In this episode of Run the Numbers, CJ breaks down Lime's S-1 as the scooter company heads toward the public markets. He gets into the $1.8B valuation, Wayne Ting's turnaround playbook, Lime's unit economics, the post-Covid recovery, and the debt wall that may be forcing the IPO window open.—SPONSORS:SpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cjBrex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjEY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:SpaceX S1 Breakdownhttps://youtu.be/AARjbTO8FKo—TIMESTAMPS:0:00 Intro1:48 What Lime does2:47 Phoenix rising from the ashes3:53 Revenue: $887M, 29% growth6:38 Gross margin and the depreciation trick7:53 Adjusted EBITDA: $218M, up 42%8:27 Why the net loss got bigger9:54 Sponsors — SpendHound | Brex | Aleph13:08 Revenue per vehicle per day13:42 Marketing: only 2% of revenue14:01 Subscription mix: 28% and rising14:25 The debt: $821M but most converts15:37 The turnaround story16:42 What Wayne found taking over17:31 The three numbers he locked in on18:05 The warehouse overhaul19:31 Sponsors — RightRev | Rillet | EY22:33 The debt deep dive23:20 Why the net loss widened24:27 Post-IPO: nearly debt free25:07 Why more scooters make each scooter worth more28:43 How a scooter pays for itself30:43 The swappable battery32:39 Is this a real moat?34:14 Red flag 1: going concern35:11 Red flag 2: depreciation change before IPO36:11 Red flag 3: permits can disappear36:32 Red flag 4: Uber is everything37:24 Red flag 5: vehicles catch fire37:56 Valuation: under 2x revenue39:55 Comps: between Lyft and Uber40:55 Bull vs. bear41:52 Legal name is Neutron Holdings42:47 Credits

On this episode of Run the Numbers, CJ sits down with Confluent CFO Rohan Sivaram to talk goal setting, prioritization, consumption-based pricing, hybrid zero-based budgeting, and the frameworks finance leaders use to scale companies. Rohan shares why he carries his 12-month goals with him, how he evaluates opportunities through TAM, technology, and team, and why usage-based pricing changes the entire operating model.—SPONSORS:EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartupsSpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cjBrex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/rohan-sivaram-69007b7/Company: https://www.confluent.io/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:A CFO Explains Marketplaceshttps://youtu.be/LpbH9GpBrSY—TIMESTAMPS:0:00 Preview and Intro2:26 Writing down 12-month goals and carrying them6:33 Rule of 168: 168 hours a week7:36 Delegation and calendar management9:25 Learning to say no: cultural shift11:32 Sponsors — EY | SpendHound | Brex14:29 Joining Confluent: the state of the company16:57 Building blocks of a budgeting process19:46 Execute, learn, adapt21:59 Healthy tension in the planning cycle22:26 Sponsors — Aleph | RightRev | Rillet25:46 What is hybrid zero-based budgeting?30:37 Moving from subscription to consumption pricing32:22 Why this was a one-way door33:56 New metrics required in a consumption business35:28 Evaluating job opportunities: the three T's37:39 Networking and reciprocity39:54 Lightning round40:04 Screwed up: free cash flow sign error42:03 Advice to younger self: take more risks42:38 Finance software stack43:00 AI tools the team has built43:44 Credits

In this episode of Run the Numbers, CJ sits down with Jake Kornreich, CFO of CoLab and former CFO of Own, live from the New York Stock Exchange. Jake breaks down the six-part framework behind Own's $2.1B sale to Salesforce, why “control your destiny” matters, how CFOs should think about IPO readiness, board communication, share price theater, and why great finance leaders operate beyond the spreadsheet.—SPONSORS:Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjEY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartupsSpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cjBrex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/jake-kornreich/Company: https://www.colabsoftware.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.comTIMESTAMPS:0:00 Preview and Intro2:20 First stock3:28 Benefits of going public today5:42 Come-up: chief of staff to CFO6:31 Running HR like a sales org8:32 Control your destiny9:24 Synergies with Salesforce10:09 Sponsors — Rillet | EY | SpendHound13:10 Do your own ROI due diligence14:40 Share price equals entertainment16:26 Disciplined execution17:45 Performance, not stories19:24 Activist investors and the acquirer's board20:13 Write the memo for the other side20:45 Sponsors — Brex | Aleph | RightRev24:02 Triangulate your way to success25:18 Your board takes snapshots, you run the movie26:21 Knowing when to sell27:16 Valuation limits your exit options27:38 Stakeholder comms during the acquisition29:58 CFO as operator, not just function31:31 What is CoLab?32:09 Why Jake joined post-Series C33:50 Personal product market fit for CFOs35:27 Lightning round35:42 Screwed up: $5M budget error36:17 Advice to younger self36:41 Finance software stack37:34 Culture of expense discipline38:22 Credits

In this episode of Run the Numbers, CJ sits down with Dan Bettes, CFO of SoundCloud, at the New York Stock Exchange. Dan breaks down how SoundCloud operates as a two-sided music marketplace, how he thinks about liquidity between fans and creators, and why great finance leaders need to make forecasting feel owned by the business—SPONSORS:Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjEY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartupsSpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cjBrex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/danielbettes/Company: https://soundcloud.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro2:17 First stock: a Vanguard index fund3:13 Most memorable IPO: Groupon4:54 Benefits of going public have changed5:47 SoundCloud and the music industry7:21 Three eras: physical, streaming, creator platform8:49 Streaming unbundled the album10:03 Artists don't need labels anymore11:40 Sponsors — Aleph | RightRev | Rillet15:00 SoundCloud's two-sided business model16:23 Touring replaced the album17:17 First metric every morning: net adds18:31 DAU vs. MAU: it's a funnel19:14 Viral moments and exogenous pops20:10 LTV and the subscription funnel21:38 Sponsors — EY | SpendHound | Brex24:35 Tops-down vs. bottoms-up: reconcile both26:21 Revenue is an output27:45 Handling forecast deviation29:24 How often to reforecast30:23 The final boss: indirect cash flow statement33:09 Cash vs. EBITDA fluency35:04 Plain English and the power of reps36:52 Tailor the message to the audience37:45 Lightning round37:45 Screwed up: miscounted corn at a banquet38:41 Lean into discomfort39:55 Craziest expense: a post-flight massage40:17 Credits

In this episode of Run the Numbers, CJ breaks down Bending Spoons' F-1 filing and the acquisition machine behind AOL, Evernote, Vimeo, Eventbrite, and more. He unpacks the company's playbook: buy under-optimized digital businesses, transform operations, raise prices, reinvest earnings, and repeat — while asking the core question: how much was built, and how much was bought?—SPONSORS:RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjEY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartupsSpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cjBrex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 What is Bending Spoons?1:03 The Internet's attic: the portfolio3:11 The metrics rundown5:44 Revenue: $1.3B, 95% growth6:04 82% of growth was bought, not built6:29 Gross margin: 66%6:50 Subscription mix and NRR7:33 Net income: basically zero8:00 Cash: $741M, debt: $4.4B8:35 Revenue per employee: $2.57M9:39 Sponsors — RightRev | Rillet | EY12:42 Organic growth is mostly price hikes13:50 A house of adjustments14:54 Add-backs bigger than the profit15:22 The reorganization line: cost of firing19:21 Sponsors — SpendHound | Brex | Aleph22:51 Does the playbook actually work?23:07 Evernote: the proof point23:45 Romini: the growth proof point24:10 AI in three directions at once25:45 The debt engine27:50 Red flag 1: material accounting weaknesses28:38 Red flag 2: pro forma numbers come with a confession29:00 Red flag 3: App Store dependency29:11 Red flag 4: no long-term contracts29:30 Red flag 5: foreign private issuer29:52 Red flag 6: they've never sold anything30:19 Cap table and board31:07 Valuation: 14–18x33:00 Bull vs. bear case33:55 Miscellaneous: the S1 is already stale35:25 Credits

CJ Gustafson sits down with Marten Abrahamsen, CFO of Vercel, at the NYSE to talk about running finance inside a hypergrowth AI company. They cover AI use cases in finance, rev rec, forecasting, KPI dashboards, PLG, consumption pricing, and Marten's “speeding tickets vs. parking tickets” framework for moving fast without losing control.—SPONSORS:Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjEY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartupsSpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cj—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/martenabrahamsen/Company: http://vercel.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Speeding tickets vs. parking tickets3:21 Visa IPO in the financial crisis5:09 Going public has changed6:45 Private market: 22–24 trillion9:03 More or fewer public companies?9:48 Sponsors — Brex | Aleph | RightRev13:04 KPI dashboard on your phone14:12 Revenue flux via Slack and Notion15:37 RevRec tool: green, yellow, red17:56 V0 is a job requirement19:43 Speeding tickets vs. parking tickets20:33 Sponsors — Rillet | EY | SpendHound23:49 Very few one-way doors25:02 Finance in hypergrowth25:39 Three-scenario planning27:00 Honest with the board31:00 PLG + consumption at Vercel33:32 What Marten checks every morning34:03 Why RPO doesn't work here35:36 Holiday usage is up37:10 ICP shifted to solo developer39:22 Capital allocation in a fast market41:32 Growth compounds; margin can't43:22 SaaS gross margins: spicy take44:24 Cash-burning AI: 2026 vs. 202147:29 Are some hypergrowth cos destroying value?50:00 Lightning round50:11 Bank of Ireland mix-up51:10 Don't punt problems forward52:04 Finance software stack52:38 Expensed an oven53:12 Credits

In this episode of Run the Numbers, CJ breaks down how stock exchanges became the operating system of modern capitalism. From ship captains raising voyage money, to the Dutch East India Company's first tradable shares, to coffee house traders, the Buttonwood Agreement, market crashes, Robinhood, and GameStop, this is the story of how markets turned ownership into something liquid, global, and very, very human.—SPONSORS:SpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cjBrex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjEY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: 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:A CFO Explains Secondarieshttps://youtu.be/pENvBuXhGukA CFO Explains the Diamond Industryhttps://youtu.be/fPrho7hvykAA CFO Explains Marketplaceshttps://youtu.be/LpbH9GpBrSY—TIMESTAMPS:0:00 The First IPO, and Why It Changed Everything2:50 Coffee, Buttonwood Trees, and the First Insider Trading Scandal6:31 The Railroads Built Your Month-End Close10:17 Sponsors — SpendHound | Brex | Aleph13:47 Buying Stocks on Credit, and How That Ended18:13 Merrill Lynch Goes to the Suburbs, and the Paper Almost Wins21:44 Sponsors — RightRev | Rillet | EY24:47 NASDAQ, Pets.com, and the Most Expensive Sock Puppet in History28:49 The Phone in Your Pocket Democratized Everything, For Better or Worse33:03 The Stock Market Was Never Really About Stocks36:47 Credits#RunTheNumbersPodcast #FinanceHistory #StockMarket #Investing #FinanceLeadership

In this episode of Run the Numbers, CJ sits down with Ryan Roccon, CFO of Zapier, to cover AI hiring standards, automating month-end close, measuring ROI on AI spend, and why determinism still beats agents most of the time.—SPONSORS:EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartupsSpendHound cuts your SaaS and AI spend by up to 30% using real pricing benchmarks across 10,000 vendors, so you always know what fair pricing looks like before your next renewal. Rated #1 on G2 in SaaS spend management, it's free forever for teams up to 1,000 employees. Sign up by June 12th and get $500 just for getting started. Go to https://www.spendhound.com/cjBrex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/ryanroccon/Company: https://zapier.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Ryan's First Appearancehttps://youtu.be/VIZ_RzfV78IChris Byington, Head of Data @ Superhumanhttps://youtu.be/ydH38JnWfww—TIMESTAMPS:0:00 Preview and intro2:11 Ryan's scope at Zapier3:17 Why the finance guy runs ecosystems6:19 AI is a required hire competency6:46 The four levels: unacceptable to transformative8:48 How Zapier tests for it11:50 Favorite interview question13:06 Sponsors — EY | SpendHound | Brex16:18 AI changes the hiring profile17:07 Support becomes customer-facing engineering18:44 Where AI beats deterministic Zaps21:00 80-90% of builds are deterministic22:41 Sponsors — Aleph | RightRev | Rillet26:00 Month end close on Zaps27:40 Time saved is a leading indicator29:53 AI token costs: COGS or investment?31:51 Performance issue or measurement issue?33:41 Partner ARR: chasing the wrong thing35:56 Build around what changes the decision37:17 The initiative sizing coach40:00 Escalate on magnitude, not certainty41:55 The 9,000 integration story44:02 M&A process and minimum model46:19 Cash vs. stock: incentive alignment48:06 CFO's role in M&A: show up early49:18 Credits

In this episode of Run the Numbers, CJ sits down with Aurélien Nolf, CFO of Navan, to unpack how to pre-align before budgeting, how to think about portfolio construction inside a company, when to fund or kill internal bets, how IR is becoming more connected to FP&A, and where AI actually works inside finance teams.—SPONSORS:Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cjBrex 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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/aureliennolf5b716412/Company: https://navan.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro1:21 Welcome and guest intro3:06 100-mile ultramarathon at Lake Tahoe4:47 Resource allocation lessons from EA6:41 Bucketing bets: proven, intuition, moonshots7:43 Pre-alignment before budgeting9:58 The 70/20/10 framework10:35 Sponsors — Rillet | EY | SpendHound13:51 The common trap: chasing everything16:16 Lyft: $1B burning to $1B profitable18:11 Killing projects without crushing morale19:24 TAM as the planning foundation20:57 Navan's TAM: managed vs. unmanaged22:15 Sponsors — Brex | Aleph | RightRev25:48 Why go after the unmanaged segment28:24 Not all TAM dollars are equal29:26 How IR is evolving30:45 Why FP&A and IR belong together31:54 Metrics: disclose vs. guide34:04 Use internal metrics externally35:12 Communicating bad news to the market39:22 Earnings prep: the black book40:04 AI in finance: can't vibe code compliance41:31 Ava handles 55% of interactions43:08 AI ROI: same framework as anything else44:02 Why finance hasn't had its AI moment44:46 Lightning round44:56 Screwed up: wrong investor meeting45:23 Sunday planning ritual46:42 Advice to younger self47:29 Finance software stack48:34 Craziest expense: curtains at the hotel laundry49:17 Credits

In this episode of Run the Numbers, CJ breaks down SpaceX's S-1, unpacking what the filing reveals about Starlink, xAI, X, common control accounting, revenue, losses, CapEx, and Elon Musk's Mars-linked compensation structure.—SPONSORS:RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cjBrex 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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run—LINKS: CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 SpaceX S1 breakdown0:50 Elon's Mars colony comp plan2:03 Common control accounting: SpaceX + xAI + X3:04 What SpaceX actually does3:43 How reusable rockets work4:24 Launch cost curve: foundation of everything5:49 Launch services: $8B, 85% of global launches6:44 Starlink: $11.4B, 63% EBITDA margins7:36 xAI and X: burning $1B/month8:22 Sponsors — RightRev | Rillet | EY11:18 Colossus and orbital AI thesis11:41 Revenue, segments and CapEx breakdown14:54 RPO: $28.4B backlog15:18 Starlink subscribers and ARPU decline16:01 Target valuation: $1.5–1.75 trillion16:47 Starlink deep dive18:05 International pricing strategy21:38 The consolidated entity problem22:28 Related party section: nine pages22:32 Sponsors — SpendHound | Brex | Aleph26:15 Valor Equity: $20B in equipment leases27:05 Tesla cross-ownership and Terrafab28:23 R&D: $8.6B, 46% of revenue30:33 Starship: key risk and growth linchpin31:41 Red flag 1: CEO comp tied to Mars colony32:22 Red flag 2: Musk concentration risk32:49 Red flag 3: Cursor option — $10B downside33:36 Red flag 4: X advertising is shrinking34:06 IPO structure and SPCX ticker34:50 30% retail allocation, no lockups35:44 S&P 500 inclusion forces buying within 15 days37:54 Valuation: 60–70x forward revenue38:43 Peer comparison39:44 What you're buying at $1.5T40:53 CFO comp: the only sane plan in the filing41:25 Bitcoin on the balance sheet41:57 Credits

In this episode of Run the Numbers, CJ sits down with ParkerGale Operating Partner Paul Stansik to break down five ways CFOs can help build a better sales engine: making the budget mean something, improving forecasting, sharpening metrics, getting involved in key RevOps moments, and building real trust with sales.—SPONSORS:Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cjBrex 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: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/paulstansik/Company: https://www.parkergale.com/Hello Operator: https://hellooperator.substack.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Is a weekly martini ARR? | with Dave Kellogghttps://youtu.be/Yb1lUQLJ6qw—TIMESTAMPS:All verified. Here are the timestamps:0:00 Preview and intro2:27 Parker Gale and Paul's role3:52 Topic: how CFOs build a better sales engine6:21 1: Make the budget mean something8:11 Budget segmentation and cleaving the business10:54 Sponsors — Aleph | RightRev | Rillet14:08 2: Help emphasize forecasting17:23 Forecasting as non-threatening co-construction19:37 Sponsors — EY | SpendHound | Brex23:06 3: Lend a hand with data and metrics25:32 Walking sales through NDR levers27:16 Metrics tied to exit readiness28:00 4: Get involved in a few RevOps spots29:04 Pricing, proposals, and quoting31:22 Kill your SKUs32:51 Selling with certainty: quote formatting34:26 CFO letter for enterprise deals37:37 5: Build a great relationship with sales37:59 You can't fix a secret39:23 EQ over IQ for finance leaders40:41 Recap: all five tips42:11 Credits#RunTheNumbersPodcast #CFO #SalesStrategy #FinanceLeadership #RevenueOperations

In this episode of Run the Numbers, CJ sits down with Figure Technologies CFO Macrina Kgil to break down how Figure's business model works, why traditional lending remains so bloated, and how speed in origination and funding flows through financial performance. They also cover stablecoins, blockchain as invisible infrastructure, AI in accounting, and scaling finance with fewer than 35 people.—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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cj—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/macrina/Company: https://www.figure.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro3:10 Working for a CEO who's a former CFO5:00 What Figure does and how it makes money6:57 Blockchain's first commercial use case8:17 50%+ margins, path to 60%9:23 Sponsors — Brex | Aleph | RightRev12:56 HELOC origination: 45 days to 5 days14:26 Where the lending system is bloated15:56 Credit and liquidity as core risks17:06 Blockchain makes the marketplace transparent18:10 Risk as a fintech CFO19:49 Sponsors — Rillet | EY | SpendHound22:58 Crypto on the balance sheet24:12 Blockchain becomes invisible like cloud25:44 Stablecoins explained27:47 YLDS: Figure's yield-bearing stablecoin29:02 Crawl, walk, run stablecoin strategy34:32 IPO process: what got easier35:03 What got harder: testing the waters37:12 Blockchain KPIs and investor conversations38:21 Finance team: 130 people down to 3540:00 SEC engagement: storytelling not financials40:49 IPO advice: pick durable KPIs42:05 First earnings after IPO: don't miss43:13 AI automation goal: 60% by 202646:11 Director of Finance Transformation hire47:40 30-60-90 for the transformation role48:58 Long-Ass Lightning Round52:20 Credits

Cerebras is going public with the largest commercial chip ever built, $510M in 2025 revenue, and a $24.6B backlog mostly tied to OpenAI. CJ breaks down the company's wafer-scale AI bet, why inference changed the story, the strange customer-investor-lender relationships behind the IPO, and the big question: is Cerebras the next NVIDIA-style infrastructure winner, or a concentrated hardware company with a very expensive cloud pivot?—SPONSORS:SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cjBrex 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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro0:59 Cerebras: the dinner plate chip3:56 Why chip size matters for AI5:26 Old vs. new AI: inference is the bottleneck7:30 Revenue: 20x in 3 years7:49 Sponsors — SpendHound | Brex | Aleph11:33 Gross margin12:02 Net income: the one-time accounting trick12:41 Operating cash flow whipsaw13:24 RPO: $24.6B backlog13:58 Customer concentration: the UAE entities18:06 Sponsors — RightRev | Rillet | EY21:05 Cloud revenue: the inverse SaaS story22:23 Cloud gross margin collapse23:53 G42 warrants for pennies29:14 The OpenAI warrant: Funky Town31:08 $40B market cap milestone31:36 R&D and S&M breakdown33:15 Balance sheet and cash burn35:59 Red flag 1: accounting weaknesses36:37 Red flag 2: one foundry, no supply deal37:28 Red flag 3: UAE geopolitical risk38:10 Red flag 4: cloud is unproven39:02 Cap table: founders diluted40:43 Voting control: Class A, B, and N41:15 Valuation: 10–13x forward revenue41:48 Peer comparison43:47 CEO's prior issues46:10 CreditsNothing said or created by this podcast is business or investment advice#RunTheNumbersPodcast #IPO #Semiconductors #AIStrategy #FinanceLeadership

David Bell, co-founder of Idea Farm Ventures and early investor behind Warby Parker, Harry's, and Diapers.com, and CJ break down how consumer investing works. They cover why durable consumer companies require more than clean unit economics, how to apply SaaS-style thinking to businesses without contracts, and why the best opportunities often live in boring gray space.—SPONSORS:EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cjBrex 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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj—Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/david-bell-086820/Company: https://www.ideafarmventures.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro3:16 Edge: economics and psychology5:21 Best ideas in boring gray space5:41 Functional, emotional, and symbolic value7:08 Grüns gummies and divisibility9:02 Sponsors — EY | SpendHound | Brex12:31 Ideation: personal pain vs. market analysis13:17 Diapers.com and the Starbucks origin story16:00 Warby Parker: asking why16:33 LTV to CAC in D2C18:02 Retention math: 85 to 90% can double LTV19:00 Milkman and recurring vs. reoccurring20:42 Trust economics22:38 Warby stores boost online sales22:58 Sponsors — Aleph | RightRev | Rillet26:12 Away store as advertising27:46 Warby discovery: dots on a map30:10 Home try-on word of mouth value32:09 D2C unit economics mistakes34:55 Innovating on distribution35:50 Touchland in Sephora: right channel, right signal37:00 Capital allocation: margin and low CAC first39:18 Sequencing: people, brand, then inventory40:58 Product vs. brand: the 8x10 thought experiment42:23 Consumer monetization shifts45:45 The gravity framework50:32 Isolation principle: most underused lever52:36 Working backwards from exit at day zero57:23 What if your business isn't venture scale?59:32 Book plug: Founders Gold1:00:25 Credits

CJ turns the mic on the people behind Mostly Media for a special behind-the-scenes episode of Run the Numbers. Michelle, Callie, Sarah, Matthew, Ben, and Steve share what it's like building the company, scaling media, talent, sales, production, and operations, and dealing with CJ's scooter lore, calendar quirks, and chaos along the way.—SPONSORS:Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cjBrex 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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro2:44 Show intro: meet the Mostly Media team3:37 Michelle Finn: accounting and ops4:28 Parts Tech days: CJ's first CFO role7:21 How the newsletter convinced Michelle to join9:02 Sponsors — Rillet | EY | SpendHound12:11 Callie Spillane: talent director13:17 Callie's background: HubSpot, Sneak, Superhuman13:40 Why Callie was hard to hire15:37 Snyk hypergrowth: 150 to 1,500 people16:59 Zero to one vs. one to ten18:20 9 of 20 roles filled: how it's going23:24 Sponsors — Brex | Aleph | RightRev26:58 Sarah Bousquet: media op27:45 Stay at home mom to ops lead33:48 CJ's schedule: American Psycho34:43 Matthew Mozzocchi: sales and partnerships35:41 Going full time with a newborn36:20 Product market fit signal38:07 Fewer, bigger bets on creators41:00 Podcast is the air game, newsletter is the ground game43:56 Ben Hillman and Steve Cerasoli: production47:46 Media in service of a product vs. the product itself48:37 Run the Numbers vs. Mostly Growth51:25 Where are we in three years?52:40 Credits#RunTheNumbersPodcast #CreatorEconomy #MediaBusiness #Entrepreneurship #ContentBusiness

In this episode of Run the Numbers, CJ Gustafson breaks down the diamond industry as a business model: how De Beers controlled supply, engineered demand, and built one of the most powerful pricing machines in history. From the Central Selling Organization to “A Diamond Is Forever” to the rise of lab-grown diamonds, this episode unpacks monopolies, scarcity, pricing power, and what happens when technology forces transparency.—SPONSORS:RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cjBrex 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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Why Uber Drivers Can't Escape the 30% Cuthttps://youtu.be/LpbH9GpBrSY—TIMESTAMPS:All verified. Here are the timestamps:0:00 Blood Diamond1:55 Show intro2:15 Diamond history: ancient India and riverbed origins3:56 Brazil supply shock and the mining era4:39 De Beers: Cecil Rhodes and the PE rollup6:47 Sponsors — RightRev | Rillet | EY9:49 The Central Selling Organization (CSO)10:39 The site system: invite-only, take-it-or-leave-it auctions12:22 Diamonds are more abundant than gold13:01 NW Ayer, Bernays, and engineering demand14:17 "A Diamond is Forever" campaign15:13 Lab grown diamonds: 20% of US purchases16:32 De Beers collapses: $3.1B operating loss17:18 Sponsors — SpendHound | Brex | Aleph21:07 Lesson 1: Rollups are powered by capital21:39 Lesson 2: Distribution beats mining22:11 Lesson 3: Artificial scarcity unravels22:55 Lesson 4: Price opacity is a temporary moat23:39 Lesson 5: Demand engineering24:30 Lesson 6: The real product was risk smoothing26:30 Credits#RunTheNumbersPodcast #BusinessStrategy #FinanceHistory #Pricing #Monopoly

In this episode of Run the Numbers, CJ Gustafson sits down with Angela Chen, former CFO of The North Face and Mars Veterinary Health, to unpack how finance leaders build and scale iconic consumer brands. Angela shares how to measure brand equity, why the CFO should act as an architect of growth, and how capital, talent, and strategy connect inside a scaling business. They also get into humanistic leadership, consumer-margin tradeoffs, and what a 39-cent Taco Bell taco can teach finance teams about growth.—SPONSORS:Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet 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/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cjBrex 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: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/angelachensf/Company: https://sku.is/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Minted's CFO: Half the Year Happens in One Monthhttps://youtu.be/hD4-exunKMo—TIMESTAMPS:0:00 Preview and intro2:45 Measuring brand equity5:09 CFO as architect of growth7:11 Connecting money, ideas, and talent7:52 North Face vs. Mars: where to invest10:52 Sponsors — Aleph | RightRev | Rillet14:14 Scaling North Face 5x without diluting the brand16:31 From technical brand to lifestyle brand19:30 Quality of revenue21:49 Seasonality and Q4 concentration24:01 Sponsors — EY | SpendHound | Brex27:14 Retailers shouldn't own factories31:30 Supply chain and 18-month product cycles33:23 Humanistic leadership in finance34:32 Purpose and profit are mutually reinforcing36:15 Purpose vs. profit in public companies38:05 Playing to Win framework39:47 Operational cadence and the gas gauge43:02 Killing bad projects: the battery jacket story44:16 Taco Bell and 39-cent margins47:10 Lightning round47:36 Screwed up: hiring on credentials48:27 Advice to younger self: network is the work50:07 Craziest expense story: snowcat ski trip50:50 Credits

In this episode of Run the Numbers, CJ sits down with PSG Managing Director Chris Nesbitt to unpack how great deals are actually found, how investment decisions are really made, and why narrative often matters more than most investors admit. They also dig into forecasting, boardroom authenticity, simple vs. complex models, and the roles of market, product, and leadership in driving outcomes.—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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet 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/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cj—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/christophersnesbitt/Company: https://psgequity.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro2:44 PSG origin story4:01 Growth to 30B AUM5:07 Strategy: small software at scale5:50 Vertical SaaS treasure hunting8:10 Ministry Brands: software meets payments9:28 Sponsors — Brex | Aleph | RightRev12:46 Early M&A work and rollup strategy15:52 Sourcing is more competitive now18:28 Smoke signals and relationship sourcing21:22 Does brand get you in the room?22:15 Authenticity as a sourcing edge22:52 Sponsors — Rillet | EY | SpendHound26:09 Brand name of investor or deal partner?27:44 Investors are narrative driven animals29:18 Market, product, then execution31:26 Danger of falling in love with the narrative33:40 Operator AI pivot story: GRC company34:51 Keep it simple: one tab, five key inputs39:21 Forecasting confidence beyond 12-18 months41:51 What makes a useful board meeting45:01 Build vs. buy: the payments decision47:45 ARR vs. EBITDA multiples50:30 Lightning round50:34 Board materials: send 3 days in advance51:03 LTV to CAC and cap software debates51:32 First deal at PSG52:35 What young investors get wrong54:04 Credits

In this episode of Run the Numbers, CJ sits down with Manu Diwakar, CFO of Virta Health, to unpack why health tech breaks traditional SaaS thinking. They get into the realities of running a business where outcomes matter, half the company are medical professionals, and efficiency can't come at the expense of care. It's a conversation about sustainable scaling, smarter reinvestment, and building for durability over hype.—SPONSORS: SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cjBrex 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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet 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/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/manu-diwakar-1aa578/Company: https://www.virtahealth.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro1:18 Welcome and guest intro3:02 What sector is health tech?4:34 Virta go to market explained7:01 B2B to B2C model9:00 Value based care and ROI guarantees9:18 Half the company are medical professionals10:36 Sponsors — SpendHound | Brex | Aleph14:03 Annual planning process16:42 Shape of the curve17:33 TAM: metabolic health is massive20:45 Fee for service vs. value based care24:16 Sponsors — RightRev | Rillet | EY27:24 Unique costs of health tech: billing, compliance30:54 Corporate practice of medicine31:44 North star: members under management32:43 The flywheel: $250 charge, $500 saved33:28 Early stage CFO job is easy35:28 Bad habits baked in during high growth38:02 Choosing not to profit vs. not turning a profit41:15 Running a VC-backed business for sustainability42:07 People, tech and process framework44:31 Hiring philosophy: hard work, learning, curiosity48:26 Athletes vs. experts in hiring50:03 Clock hands interview question50:49 Lightning round51:09 Screwed up: having hard conversations late51:57 Advice to younger self52:15 Finance software stack52:42 Craziest expense story53:47 Credits

In this episode of Run the Numbers, CJ sits down with Praveer Melwani, CFO of Figma, to unpack the financial model behind one of tech's most iconic product-led companies. They cover viral growth, forecasting without a traditional sales pipeline, AI credit pricing, margin tradeoffs, and the metric Praveer believes matters most in the long run: free cash flow per share.—SPONSORS:EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.comBrex 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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet 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: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/praveer-melwani/Company: https://www.figma.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro1:21 Welcome and guest intro2:55 From banking to Dropbox to Figma5:04 Inflection points: building trust early8:36 TAM expansion thinking10:31 Sponsors — EY | SpendHound | Brex13:38 Two-thirds of Figma users aren't designers14:36 Forecasting product led growth16:22 Cohorts and NDR discovery17:39 LTV to CAC philosophy18:57 Product signals for account expansion20:22 How Figma achieved hypergrowth with 90%+ margins22:14 AI expands TAM: time to hit the gas23:22 AI credit pricing model24:50 Sponsors — Aleph | RightRev | Rillet28:13 Outcome based pricing consideration29:00 Where AI margins settle: gross profit dollars30:08 Free cash flow per share as north star31:04 NDR and pricing volatility32:13 Bundled vs. unbundled seats34:50 Being engaged in sales to understand admin pain35:17 IPO day experience36:27 Keeping employees focused beyond the stock price37:19 Employee stock pressure and lockup reality39:37 Kitchen cabinet of advisors41:44 How to ask better questions of advisors41:47 Lightning round41:50 Advice to younger self42:47 Finance software stack44:09 Claude WTF moment: forecasting model throughput45:13 Craziest expense story: the haircut45:59 Credits

In this episode of Run the Numbers, CJ sits down with Wealthfront CFO Alan Imberman to unpack automation as a strategy, the compounding power of retention and trust, and how to balance elite profitability with continued investment. They also discuss why Wealthfront went public earlier than many peers and what's really happening in fintech right now.—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/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.comBrex 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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/alan-imberman-cfa-aab2371/Company: https://www.wealthfront.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro1:37 Welcome and guest intro3:11 Wealthfront overview4:38 Automation as core philosophy6:50 55K clients per support rep example7:45 90% gross margins and $1M revenue per employee8:46 Optimization vs. exploration framework9:58 Data flywheel: the Path product10:43 Cash account insight from customer data11:26 Home lending insight from wire data13:33 Sponsors — Rillet | EY | SpendHound16:45 Product led growth and referrals18:11 Incentives vs. paid marketing20:46 Compounding philosophy and 120% NDR22:07 Long term thinking vs. public market pressure22:40 No guidance decision26:26 Sponsors — Brex | Aleph | RightRev29:44 Serving the wealth builder: 80/20 in wealth management31:45 Decision to go public at $339M revenue33:46 Does size matter for IPOs?34:46 Fintech's moment: Chime, Klarna, Circle36:49 Non-monetary benefits of going public38:30 Memos over slides40:31 Hedge fund early career: spreading 10-Ks in Excel46:45 Don't lose the forest for the trees in modeling48:31 Lightning round48:43 Screwed up: de-annualizing a fee rate49:55 Advice to younger self50:32 Finance software stack51:14 Craziest expense story: $100K coffee tab53:11 Credits#RunTheNumbersPodcast #CFO

On this week's Run the Numbers, CJ sits down with Steve Isom of Bloomerang to break down what a “strategic CFO” really is. They cover the shift from reporting to operating, why customer orgs drive SaaS value, and how AI is reshaping the finance role. —SPONSORS:RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet 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/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.comBrex 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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run—LINKS: Steve on LinkedIn: linkedin.com/in/steveisomjrCompany: https://bloomerang.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview1:25 Intro2:55 Welcome Steve Isom3:13 CFO to COO promotion5:02 Having a pulse on every function6:51 Defining "strategic CFO"7:19 Tying strategy to value creation9:27 Being embedded in the rhythm of the business10:55 Finance leaders as commentators vs. team captains12:25 Sponsors — RightRev | Rillet | EY15:33 Killing projects as a core skill18:14 Activity doesn't equal impact19:16 Project Steve killed20:39 Taking over the customer org at Bloomerang22:18 Why acquisition is a cash-losing exercise23:07 LTV lives post-sale24:39 Most vulnerable area: customer success25:24 Ruthless CSM segmentation26:30 Nonprofits don't think about your software29:21 Sponsors — Spendhound | Brex | Aleph32:43 CFO running ops35:52 Metrics vs. humans37:18 Skip levels and what they reveal39:01 Incentives drive the wrong outcomes40:22 Customer-introduced delays as a key sub-metric40:27 Unit economics become tangible when you're accountable42:17 Going deep on AI45:13 Motivating your team to experiment with AI46:02 AI for personal projects47:05 Resource allocation in a vibe-coding world48:42 Does AI efficiency just mean more work?50:32 What excites Steve about the future of finance leadership52:08 Finance leaders who don't use AI won't get hired52:13 Credits#RunTheNumbersPodcast #CFO #StrategicFinance #SaaSFinance #FinanceLeadership #CFOtoCOO

Secondaries aren't a niche anymore — they're the main event. In 2025, the secondary market hit $233B, outpacing IPOs 5:1. This episode breaks down how we got here, why companies stay private longer, and how employees, investors, and CFOs actually navigate liquidity. From Facebook's wild west to structured tenders and continuation vehicles — this is the new playbook.—SPONSORS:Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet 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/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.comBrex 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: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.comBen on LinkedIn: https://www.linkedin.com/in/slackerstuff/Slacker Stuff: https://www.slackerstuff.com/—RELATED EPISODES:IPOs Are Being Replacedhttps://youtu.be/oGuZf83pdREThe $10T Question: Who Needs Wall Street?" | Scott Vosshttps://youtu.be/szCIZmTs3SQDriving revenue without selling | Greg Henry of 1Passwordhttps://youtu.be/f5FsNoG8A3EFinance vs. Marketing: Who's Really Right About ROI? | Brandon Sullivanhttps://youtu.be/ivcht5N7uRQDo the things spreadsheets can't do | SeatGeek's Teddy Collinshttps://youtu.be/jn0L5KkmMI4—TIMESTAMPS:0:00 The $233B market replacing IPOs2:57 What is a secondary?4:24 The dot-com hangover5:48 The wild west era8:58 Sponsors — Aleph | RightRev | Rillet12:21 Why companies stay private longer13:56 The three stakeholders18:57 When is it too early?20:42 How to run one of these things23:57 Sponsors — EY | SpendHound | Brex27:04 Not all shares are created equal31:08 The good, the bad, and the ugly34:23 GP-led continuation vehicles36:19 The whole game changed37:34 Credits#RunTheNumbersPodcast #PrivateMarkets #SecondaryMarkets #VentureCapital #CFO

In this episode of Run the Numbers, CJ sits down with Glenn Schiffman, CFO of Fanatics. They break down the economics of sports IP, how Fanatics approaches CAC, LTV, and capital allocation across merchandising, collectibles, and betting, and the negotiation lessons Glenn learned from decades in investment banking and leading finance at IAC.—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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet 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/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/glenn-h-s-51440521/Company: https://www.fanaticsinc.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro1:13 Welcome and guest intro2:38 Football at Duke and college businesses5:40 Predecessor to DoorDash story7:10 IP monetization explained9:22 All deals are snowflakes10:36 Partnership KPIs13:21 Sponsors — Brex | Aleph | RightRev16:40 Buy, bet, collect: CAC and LTV17:15 Single view of the fan18:39 Multi-business customers spend 4.7x20:32 Fanatics credit card launch22:13 AI for personalization23:01 DTC vs. wholesale margin profiles24:05 Budgeting process26:07 Infinite vs. finite: focus on revenue26:37 Sponsors — Rillet | EY | SpendHound29:47 Starve your losers, feed your winners32:58 Capital compounding: revenue, EBITDA, FCF33:56 Buybacks at IAC37:02 First negotiation at Lehman39:17 Outlasting the other side39:56 Listening in negotiations40:03 Long-Ass Lightning Round44:25 Credits#RunTheNumbersPodcast #CFO #SportsCommerce #CapitalAllocation #FinanceLeadership

In this episode of Run the Numbers, CJ sits down with Kunal Agarwal, CFO of Gorgias, to unpack how AI is reshaping pricing and operations. They discuss outcome-based pricing, how to forecast LLM-driven costs, and why order-to-cash isn't just back-office plumbing—it can be a true growth lever when designed correctly.—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: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/agarwalk/Company: https://www.gorgias.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro2:14 PE to venture incubator4:39 Operational empathy from zero-to-one4:45 First paying user feeling5:40 Jet ski customer support story8:49 Hanging with IC sales reps12:24 Sponsors — Tabs | Abacum | Brex15:44 Finance as the decision engine17:36 Gorgias overview20:20 Pricing structure and iteration22:11 Outcome based / resolution pricing24:48 AI success rate as key metric25:33 Sponsors — Metronome | RightRev | Rillet28:57 Pricing value split — $1 per resolution31:17 Vertical specificity as AI moat33:27 Managing LLM costs35:41 Falling token costs and model mix39:28 Order to cash as growth engine43:31 Auditing order to cash at 25M ARR44:09 Manual choke points46:32 Learning density over titles48:30 SurveyMonkey as the most formative period50:07 Lightning round50:17 Listening to respond vs. listening to learn51:04 Advice to younger self52:02 Finance software stack52:45 Cortex — internal AI decision tool54:21 Craziest expense story54:52 Credits

In this episode of Run the Numbers, CJ sits down with Federico Acabbi, investment banker at RBC, to break down what's happening across cybersecurity, infrastructure, and the broader software market. They cover why horizontal software is under pressure while security spend holds up, what it really takes to go public today, and how the IPO process actually works behind the scenes—from diligence to pricing.—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: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNFederico: https://www.linkedin.com/in/federicoacabbi/rbccm.comCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro2:36 Software investability right now6:46 Cyber — CFO's #2 investment priority8:17 AI turbocharging attacks9:08 DevOps disruption10:30 Sponsors — Rillet | Tabs | Abacum13:55 IPO landscape overview14:33 Revenue and market cap benchmarks19:24 Founder share sales at IPO22:28 Secondary market vs. IPO market23:14 How many IPOs can the market digest?24:20 Investor mix for larger vs. smaller IPOs25:04 Sponsors — Brex | Metronome | RightRev28:23 Role of mutual funds in IPOs30:00 What banks actually do on an IPO31:49 Book building and allocation32:43 Research coverage35:52 NDRs and testing the waters38:59 Roadshow format — then vs. now40:41 Direct listings explained43:57 How banks make money on IPOs44:56 Fee splits between banks47:36 IPO vs. M&A — which is more attractive?51:02 Junior banking story — Nokia and the Vespa54:31 Craziest expense story56:08 Credits