Run the Numbers

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 It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down.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

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

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

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

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