Podcast
Run the Numbers
Hosted by CJ Gustafson · EN
Run the Numbers is a business podcast about financial metrics and business models for CFOs, aspiring CFOs, finance leaders, and ambitious people operating tech startups. Hosted by CJ Gustafson, CFO and writer of Mostly Metrics, the show shares lessons, frameworks, and operator insights from the trenches as a tech exec. Think of it as a playbook for the things CJ wishes he knew earlier in his career, covering SaaS metrics, annual budgeting, forecasting, headcount, equity, dilution, fundraising, and the decisions that drive performance and growth.
63episodes
Episodes
Newest firstAll episodes
Xero’s CFO: Why Finance Is Taking On More of the Business
3d ago00:49:59Tap to summarizeIn this episode of Run the Numbers, CJ Gustafson sits down with Xero CFO Claire Bramley to discuss how the CFO role is expanding beyond finance into strategy, operations, transformation, and technology. Claire also shares how she builds teams around her weaknesses, what small businesses actually want from AI, and why she views diversity as a business performance decision.—SPONSORS:Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/claire-bramley-133b7174/Company: https://www.xero.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro3:00 Xero and CJ's History With It4:12 Xero's Size and Scale Today5:10 The Expanding CFO Role7:06 Hiring Experts You're Not8:47 Imposter Syndrome11:00 Getting Better at Asking Questions15:04 Asking the "Stupid Question"16:21 Finance as the Corporate Junk Drawer17:48 The Trial Period Idea18:24 Tripwires: Leading Indicators for CFOs25:35 AI Hype vs. Main Street Reality26:44 What Small Business Owners Actually Want28:45 What Big Corps Underestimate31:10 Trust as a Competitive Moat33:45 Why the Line Is Thinner for Small Biz35:12 AI Inside Claire's Finance Team37:23 AI for Investor Relations39:28 Diversity as Capital Allocation42:07 A Decision Diversity Changed44:45 Lightning Round Begins46:06 Advice to Her Younger Self48:49 Craziest Expense Ever#RunTheNumbersPodcast #CFOLife #FinanceLeadership #AIinFinance #WomenInFinance
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A CFO Explains Private Jets
6d ago00:34:31Summary readyOn this episode of Run the Numbers, CJ and Ben trace corporate private jets from Sam Walton’s scrappy two-seater to Alex Karp’s $17 million jet bill. They break down when flying private actually makes business sense, how jets hit the balance sheet, the tax and accounting implications, what companies disclose to investors, and when executive travel crosses the line from productivity tool to corporate excess.—SPONSORS:Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Jersey Mike’s IPO: The $4.2B Sandwich Machinehttps://youtu.be/ZL6AbqHI-0g—TIMESTAMPS:0:00 Fly Like a G60:29 $17M on jets: Alex Karp guess1:16 Sam Walton starts it all2:49 The yellow legal pads4:37 Walmart Aviation founded (1968)5:14 Piston to Bombardier jets6:51 Walmart's modern jet fleet8:13 Where it hides in SEC filings9:25 SEC Reg S-K Item 40213:37 Gulfport Energy scandal14:42 Tyco: Kozlowski & Schwartz16:57 When jets are actually useful17:55 P&L vs. balance sheet treatment18:40 PP&E and depreciation basics19:04 Off-balance-sheet leases19:28 The chartering loophole19:54 "Uber Jet" fractional ownership23:14 How activists hunt jet spend23:36 Flight registries & tail numbers24:13 Jack Sweeney vs. Elon Musk25:00 What top companies spend25:18 Walmart's fleet is #126:17 Charter vs. lease vs. own29:02 Should we care? 3 angles30:06 Angle 2: opportunity cost30:59 Angle 3: company size31:42 General Electric's shadow jet32:50 Back to Alex Karp34:02 Credits#RunTheNumbersPodcast #PrivateJets #CorporateFinance #ExecutivePerks #CFOLife
Summary
The Business of Saving Lives: Inside RapidSOS
1w ago00:49:59Summary readyOn this episode of Run the Numbers, CJ Gustafson sits down with Richard Haram, VP of Finance at RapidSOS, to unpack how finance supports a public safety AI platform that helps 911 operators and first responders act faster. They cover building AI fluency, combining FP&A with BI, monetizing vertical software, integrating acquisitions, and the leadership lessons Richard carried from entrepreneurship.—SPONSORS:Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/richardharem/Company: https://rapidsos.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro3:10 What RapidSOS does4:59 CJ’s own car accident5:33 What's broken about 9116:50 Who's the actual customer7:46 How RapidSOS monetizes10:13 Sponsors — Pulley | Rillet | Maximor13:27 Too much data, too much noise16:35 Data pollution and trust18:24 The data stack early on19:25 Should BI have come sooner?20:45 The framework: questions to decisions22:43 Building a data culture23:58 Sponsors — Brex | Anrok | RightRev26:51 Bottoms-up vs. top-down AI28:42 Inspiration, not training32:24 The three-phase AI progression33:31 Founding an AV company at 835:37 Giving people room to grow38:12 Depending on heroes39:55 Working under founder personalities41:23 Do startups undervalue what they sell42:48 A price hike, zero churn43:24 Signs you're underpricing44:57 Lightning round45:03 Screwed up: refreshed data before a demo47:15 Advice to younger self47:41 Finance software stack48:37 Craziest expense: personal gas49:29 Credits
Summary
Building an AI-Native Finance Team with Plaid CFO Seun Sodipo
2w ago00:52:50Summary readyOn this episode of Run the Numbers, CJ sits down with Plaid CFO Seun Sodipo. Seun explains how her team is using AI to improve speed, accuracy, and ambition; why finance leaders need both bottom-up experimentation and top-down direction; and how she approaches planning, network effects, and building a durable company.—SPONSORS:RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cjPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/seun-sodipo-1498b580/Company: https://plaid.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro2:12 What Plaid does3:53 How Plaid makes money7:04 Eight months in, not new anymore8:57 Sponsors — RightRev | Pulley | Rillet11:48 Career path: Stripe, Glossier, Plaid14:32 Evaluating durability from the outside15:36 Rising expectations and AI17:23 Top-down vs. bottoms-up AI adoption20:06 Sponsors — Maximor | Brex | Anrok23:20 Coolest AI use case: sorting physical mail25:21 How her questions have changed27:11 AI should make you think deeper27:51 Finance AI Day explained31:23 A four-month journey to usable tools32:22 How AI changed her leadership style33:19 Skills that matter more now36:22 The Objective, Strategy, Tactics framework39:56 What planning reveals about an org41:36 Sequential vs. parallel planning45:38 Measuring the value of a network47:33 What people underestimate about Plaid48:56 Lightning round48:56 Screwed up: the reversed page order49:39 Advice to younger self50:32 Finance software stack51:43 Craziest expense: the photo shoots52:20 Credits
Summary
How to Tell a Demanding Founder They’re Wrong
3w ago00:38:30Summary readyOn this special episode of Run the Numbers, CJ Gustafson revisits standout moments from past conversations with Alex Immerman, Curt Sigfstead, Daniel Kang, Adam Ante, and David Laptor. Together, their advice reveals how great CFOs earn trust, challenge founders, speak up when the data says something is wrong, and become true strategic partners without relying on the power of the purse strings.—SPONSORS:Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro3:27 Alex Immerman's favorite CFO interview question4:54 What a weak answer looks like5:26 When the hard calls actually matter6:37 Walt and Roy Disney7:36 Liked even when making unpopular calls8:43 Sponsors — Anrok | RightRev | Pulley11:35 Curt from Clio: ego in the bottom drawer13:52 CFO as supporting cast15:10 Backbone vs. ego: when to use each16:23 Daniel Kang: don't use the purse strings as power17:36 Earn the seat, don't demand it18:52 Money is one arrow, not the whole quiver20:39 Sponsors — Rillet | Maximor | Brex23:54 Adam Ante: finance people pigeonhole themselves26:46 The CFO can sit in any meeting27:30 First 90 days: listen before suggesting28:46 David Laptor: listen, observe, think, speak30:50 Build a culture where speaking up is welcomed31:51 Curt from Clio: don't come in as a know-it-all33:08 Earn trust through curiosity33:46 Beware of all-green dashboards35:28 What would CJ say to Ballmer?37:14 Parting thoughts from Ben38:00 Credits
Summary
The Four Stages of World-Class FP&A with Datadog’s AJ Ljubich
3w ago00:57:47Summary readyOn this episode of Run the Numbers, CJ sits down with Datadog SVP of FP&A AJ Ljubich to break down the four stages of a world-class finance team.—SPONSORS:Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/aj-ljubich-cfa-727ab912/Company: https://www.datadoghq.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro2:42 FP&A as a product team4:53 The five pillars of AJ's team6:39 How far FP&A has come7:33 How do you know you're doing a good job?10:20 FP&A as the dashboard, not the engine10:20 Sponsors — Brex | Anrok | RightRev13:18 The four-stage FP&A maturity model16:00 Can you reach all four stages at Series B?16:45 Why AJ holds weekly forecast meetings18:24 How often to actually change the forecast21:42 Sponsors — Pulley | Rillet | Maximor24:49 Single source of truth: still on the vision board26:12 AI and the self-serve data risk26:21 CAC payback over LTV to CAC29:39 Inside sales vs. enterprise payback comparison31:47 Finance as the yes, but people34:02 FP&A vs. IR: which is harder?36:14 How IR makes you a better FP&A leader37:19 Is the IR profile shifting?42:01 IPOs are branding events, not finish lines43:27 The Datadog IPO during the WeWork meltdown45:15 Career philosophy: do great work where you are49:52 Datadog didn't have a role for AJ when he started52:16 Lightning round52:24 Screwed up: forgot the currency guy54:37 Finance software stack56:16 Advice to younger self57:13 Credits
Summary
Dave McClure and Aman Verjee on Angel Investing at Scale, 500 Startups, and Practical VC
4w ago01:00:59Summary readyOn this episode of Run the Numbers, CJ sits down with Dave McClure and Aman Verjee of Practical VC to talk about the evolution of startup investing — from the PayPal mafia and Founders Fund era to 500 Startups, YC-style scale, and today’s secondary market.—SPONSORS:Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuests:https://www.linkedin.com/in/davemcclure/https://www.linkedin.com/in/aman-verjee/Company:https://practicalvc.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro3:00 Writing as a distribution strategy5:17 How Dave's blog led to Founders Fund7:24 Aman: writing at PayPal and law school9:29 PayPal: the red pen of David Sacks11:44 Sponsors — Rillet | Maximor | Brex14:59 500 Startups: the original thesis16:22 The volume strategy: more shots on goal18:44 Twilio, Lyft, Sendgrid, Credit Karma20:15 60x returns: right place, right time23:07 Sponsors — Anrok | RightRev | Pulley25:58 Accelerator ecosystem evolution28:42 500 vs. YC: scale as a weapon32:52 Globalizing the accelerator model35:04 Seed to secondaries: how it happened37:00 Scratching their own itch for liquidity38:10 The secondary market explained40:50 Types of secondaries43:29 Why would a VC sell a winner?46:07 Managing DPI as a late-stage manager47:02 The five horse framework49:15 Skipping the J curve51:44 Imperfect information as a feature55:22 Landmines: fraud, mismarked valuations57:00 VCs lie about valuations three ways57:58 Forward contracts and counterparty risk1:00:29 Credits
Summary
Cumberland Farms S-1 Breakdown: Fuel, Snacks, and Debt
Jul 1600:36:38Summary readyOn this episode of Run the Numbers, CJ breaks down Cumberland Farms’ IPO filing and the surprising business behind it.—SPONSORS:RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro2:57 Key metrics4:28 Europe now out-earns America5:01 $5.8B debt at 8x leverage6:20 TLDR: snacks, gas, borrowed money7:58 Fuel vs. inside: the gross profit photo finish8:58 COCO, CONCO, and OTHER explained10:57 Sponsors — Maximor | Brex | Anrok14:02 Why scale matters: four reasons16:02 The US convenience store market17:42 EVs: long the birth rate18:05 Back to the debt19:10 The sale leaseback20:24 Sponsors — RightRev | Pulley | Rillet23:26 Does the deleveraging math work?24:27 The growth thesis25:06 600–700 stores become Cumberland Farms26:16 The chicken fryer ROI27:00 Coffee and loyalty: 6M members in 13 months28:15 Red flag 1: five-for-five COSO failures28:41 Red flag 2: entire C-suite is new29:04 Red flag 3: lending to their own parent29:42 Red flag 4: Big Tobacco funds loyalty29:57 Red flag 5: foreign issuer, Cayman charter30:10 Red flag 6: one supplier is 31% of costs30:32 Red flag 7: balance sheet is stale30:45 Cap table: TDR Capital and the Issa brothers31:55 Casey's vs. ARCO33:47 Goldman got bumped34:08 Massachusetts banned the pump clip until 201534:57 No health insurance disclosure for 16K US workers35:30 Robert Swan (ex-Intel CEO) is on the board36:08 Credits
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Token Economics, AI ROI, and the Future of Investment Banking with Rahul Rekhi
Jul 1300:59:51Summary readyIn this episode of Run the Numbers, CJ sits down with Rogo president Rahul Rekhi to unpack what AI actually changes in investment banking and finance. They dig into token economics, why adoption without ROI is a trap, how vertical AI wins, and why domain expertise still matter.—SPONSORS:Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtnRightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/rahulrekhi/Company: https://www.rogo.ai/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:A CFO Explains the Stock Exchangeshttps://youtu.be/pooOE6ZNGR4A CFO Explains Marketplaceshttps://youtu.be/LpbH9GpBrSY—TIMESTAMPS:0:00 Preview and Intro2:44 Why finance was first to verticalize AI6:28 What the president title means at Rogo9:55 Sponsors — Pulley | Rillet | Maximor13:02 The problem Rogo is solving16:16 Token maxing is not transformation17:43 Why ROI is so hard to measure19:39 Sponsors — Brex | Anrok | RightRev22:37 ROI is business-unit specific24:03 Budgeting tokens like a benefits load25:00 AI incentives aren't aligned to efficiency26:26 The model broker function32:03 Not all token spend is equal37:14 Who owns AI efficiency?40:59 The forward deployed banker43:00 Domain expertise: the Interstellar analogy49:21 Lightning round49:28 Screwed up: DCF error in a live deal51:13 Will new grads have the spidey sense?53:03 Meeting Pope Francis55:04 Fact-checking jobs numbers at the White House57:39 Advice to younger self59:21 Credits
Summary
Jersey Mike’s S-1 Breakdown: How a $4.2B Sandwich Machine Works
Jul 900:28:26Summary readyOn this episode of Run the Numbers, CJ breaks down Jersey Mike’s S-1 and the franchise machine behind more than $4 billion in sandwich sales. He explains how an asset-light royalty model works, why franchise economics can be so powerful, what Blackstone saw in the business, and what the filing reveals about growth, margins, and the real money behind the subs.—SPONSORS:RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.comPulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetricsRillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cjMaximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metricsAnrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Sell $4B in subs, own none of the stores0:33 Origin story: Peter Cancro buys a sub shop at 171:47 It's a royalty business2:42 Key metrics6:07 What you're actually buying6:42 The three revenue streams7:19 The franchisee's P&L10:00 Sponsors — RightRev | Pulley | Rillet13:02 Corporate P&L: 47% EBITDA margins13:33 The Blackstone math14:38 $2.1B whole business securitization15:09 Full EBITDA bridge16:00 The CEO buying back the 2%17:10 Red flag 1: Up-C structure18:11 Red flag 2: tax receivable agreement18:45 Red flag 3: controlled company governance19:05 Red flag 4: sponsor already took $500M19:29 Red flag 5: charitable donations added back20:13 Red flag 6: cheap debt maturing in 202920:52 Sponsors — Maximor | Brex | Anrok23:56 Valuation: $10–12B24:32 Peer comparison25:27 How do you underwrite $12B?25:58 Misc: quantum attack on the provolone26:28 The hidden 53rd week26:57 No drive-thru is a feature27:13 Verdict27:56 Credits#RunTheNumbersPodcast #IPO #Investing #BusinessStrategy #FinanceLeadership
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