Run The Numbers

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

In this episode of Run the Numbers, CJ sits down with financial historian and PayPal Mafia member Aman Varejee to explore the recurring patterns behind economic bubbles. Drawing on research from his upcoming book “A Brief History of Financial Bubbles”, Aman explains what defines a bubble, the psychology that fuels speculative manias, and why major technological shifts—from railways to the internet to AI—often coincide with periods of extreme market speculation.—SPONSORS:RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNAman: https://www.linkedin.com/in/aman-verjee/https://practicalvc.com/Aman's book: https://bigbubbletrouble.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro1:38 Welcome and guest intro3:48 Defining a bubble6:03 Cognitive biases behind bubbles10:27 Sponsors — RightRev | Rillet | Tabs13:56 Do bubbles produce breakthroughs?14:35 Dot-com bubble — winners and losers16:00 UK railway bubble21:24 Bubble warning signs25:30 Sponsors — Abacum | Brex | Metronome28:47 Do bubbles attract grifters?31:11 Role of government in bubbles35:59 Bubble duration vs. severity37:32 2008 — roots go back to 199240:27 Are bubbles connected through time?43:38 Are we in an AI bubble?45:06 Nvidia vs. Cisco valuation comparison46:52 Circular finance in AI49:16 FP&A at PayPal under Thiel and Musk52:02 PayPal's referral campaign and LTV/CAC54:40 Book plug55:09 Credits#RunTheNumbersPodcast #Fintech #EconomicBubbles #FinanceHistory #CFO

In this episode of Run the Numbers, CJ sits down with Jason Lee, CFO of Faire, to unpack the economics of wholesale marketplaces. They break down how Faire connects independent brands with local retailers, the key metrics that matter in marketplace businesses, and ROI as a decision-making framework. Jason also shares lessons from scaling Square through its IPO and how finance leaders navigate valuation resets in private markets.—SPONSORS:Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNJason: https://www.linkedin.com/in/jason-lee-11787020/Faire: https://www.faire.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro3:01 How Faire serves retailers5:49 Revenue model and retention metrics8:21 Recurring vs. reoccurring revenue11:54 Sponsors — Metronome | RightRev | Rillet15:17 Input vs. output metrics17:13 The business equation19:08 Metric ownership22:07 Killing metrics: signal to noise23:21 800 metrics at Faire24:51 Customer count as a misleading metric26:04 Sponsors — Tabs | Abacum | Brex29:25 Planning cadences at Faire32:41 When to reallocate resources36:40 ROI as a framework40:25 Portfolio view of investments43:53 Discipline is knowing where to say yes47:11 Faire's valuation reset50:49 Tender offer mechanics55:33 Screwing up IR at Square IPO56:52 Advice to younger self58:44 AI at Faire59:32 Claude connected to data warehouse1:00:16 Tariff analysis with AI1:02:38 Credits#RunTheNumbersPodcast #Marketplace #CFO #SaaS #FinanceLeadership

In this episode of Run the Numbers, CJ sits down with Mike Wilcox, CFO of Blockchain.com, to unpack the economics of crypto exchanges. They discuss how platforms serve both retail traders and institutional clients, the different ways exchanges generate revenue, and the tension between blockchain's radical transparency and the valuable first-party data exchanges control.—SPONSORS:Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNMike: https://www.linkedin.com/in/mike-wilcox-65078a12/https://www.blockchain.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:Here's the trimmed version:0:00 Preview and intro2:12 Tradfi to crypto transition3:49 Blockchain.com origin5:45 CFO as business partner6:01 Finance team backgrounds7:02 Banking relationships8:51 On ramps and off ramps8:51 Retail vs. institutional10:53 Sponsors — Brex | Metronome | RightRev14:09 B2C to B2B motion16:04 Shared infrastructure18:31 Go-to-market differences19:00 Brand equity and low CAC20:06 Education as top-of-funnel21:13 Institutional vs. retail volatility22:37 Exchange vs. brokerage model23:56 How brokerages make money24:06 Sponsors — Rillet | Tabs | Abacum27:31 Setting take rates29:13 Distribution flywheel30:13 Data as a moat31:13 Nigeria market playbook31:44 Crypto balance sheet33:25 Duration matching34:37 Transaction-level risk36:12 Latency arms race37:28 Stablecoins and CFOs38:13 Risk vectors40:01 Annual planning41:51 Lightning round43:00 Finance software stack43:31 Advice to younger self44:09 Credits

CJ sits down with Marshall Hawks, a 20-year veteran of venture lending and author of Venture Debt Deals. They cover the real rules of thumb behind deal sizing, why lenders underwrite likelihood of raising again (not breakout outcomes), how banks and private credit differ, the three real sources of repayment, and how to actually run a venture debt process without blowing your legal budget.---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/cjLINKS:Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNMarshall: https://www.linkedin.com/in/marshallhawks/Marshall's website: https://www.marshallhawks.comCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.comTIMESTAMPS:0:00 Preview and intro3:23 Marshall's background and the book4:47 Venture Deals as inspiration6:30 Companies Marshall has worked with6:49 The venture debt sweet spot8:01 Why venture debt follows equity raises10:55 The 25–40% rule of thumb12:08 AI companies and the limits of the rule13:58 Sponsors — Abacum | Brex | Metronome17:15 How lenders think vs. investors19:12 The three sources of repayment21:37 Venture debt and the AI boom23:52 Banks vs. private credit26:28 Sponsors — RightRev | Rillet | Tabs29:57 Private credit pricing and warrants33:04 Syndicated deals35:04 Legal timelines38:13 Who pays the legal bill?40:06 Why your GC shouldn't quarterback the deal41:30 What forecast to give your lender43:37 Reporting cadence45:57 Bad news should travel fast47:49 The Twitch case study50:19 Are we over our skis in 2026?54:50 Where to get Venture Debt Deals55:09 Credits

In this episode of Run the Numbers, CJ sits down with Superhuman's Head of Analytics Chris Byington. They break down where analytics should sit inside a company, why dashboards often fail, and how the best teams connect metrics, OKRs, and forecasting to real decisions. Chris also explains why “ship goals” can mislead teams and what CEOs and CFOs should expect from a truly decision-driving data function.—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/cLTxtAsNChris: https://www.linkedin.com/in/chris-byington/Superhuman: https://superhuman.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Matt Hudson Episodehttps://youtu.be/_FWGYkzhymQ—TIMESTAMPS:0:00 Preview and intro3:29 Centralized analytics team7:29 Start analytics with problems not tools9:41 Lead with the problem10:14 Align on growth model11:46 Pre-commit to decisions13:14 Sponsors — Tabs | Abacum | Brex16:35 Dashboards need growth context19:10 Where analytics should sit21:18 Pros and cons of analytics in finance23:18 Operations vs revenue org placement24:11 Hub-and-spoke analytics model25:18 What “embedded” actually means26:14 Sponsors — Metronome | RightRev | Rillet29:38 When self-service analytics works32:04 Self-serve pitfalls33:44 Buy vs build BI35:44 Analytics owns metrics38:26 Hero metric example41:41 Outcomes > shipping42:14 Set goals before build43:57 Metrics are outcome proxies46:40 Easy way to say no48:29 Start answers with yes52:17 Proving analytics impact56:19 Credits#RunTheNumbersPodcast

In this episode of Run the Numbers, CJ breaks down the 5,000-year history of marketplaces—from Mesopotamia to Amazon—and the economics behind take rates, trust layers, and vertical unbundling. We unpack Airbnb's fee backlash, Facebook Marketplace's hidden value, why inventory kills platforms, and how AI will reshape discovery—without eliminating the middleman.—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/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.comSlacker Stuff: https://www.slackerstuff.com/Ben: https://www.linkedin.com/in/slackerstuff/—RELATED EPISODES:The Mindshare Advantage Marketplace Success With Boris Wertz of Version One Ventureshttps://youtu.be/kN61sAxw_ykThe Marketplace Plus Model Explained | Colin Gardiner of Yonder VChttps://youtu.be/VIWFVwCfyLEA CFO Explains the History of EBITDAhttps://youtu.be/JySZv_fSNqs—TIMESTAMPS:0:00 Preview1:34 Marketplace Origins2:48 The Digital Shift5:55 Unbundling of Craigslist9:56 Sponsors — Rillet | Tabs | Abacum13:21 Smart Phone Revolution17:33 Take Rate Calculations21:08 When the Marketplace Crosses the Line24:49 Sponsors — Brex | Metronome | RightRev28:09 When Fees Become Friction30:37 The Marketplace Plus Model33:26 The $100B Flea Market36:14 The Inventory Trap40:07 The Disintermediation Problem42:35 Convenience Beats Inspection45:09 AI Compresses the Marketplace47:56 You Can't Cut Out the Middleman50:03 Credits#RunTheNumbersPodcast #Marketplaces #PlatformEconomy #Middleman #TechStrategy

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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