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Run the Numbers

CJ Gustafson
Run the Numbers
Último episódio

339 episódios

  • Run the Numbers

    How to Sell Your Company: A Multi-Time CFO's Full Playbook | Rick Smith

    17/09/2026 | 1h 6min
    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 It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down.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/cj

    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/cj

    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/metrics

    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/rtn

    EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups



    LINKS: 
    Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
    Guest: linkedin.com/in/rick-smith-906939
    Company: https://www.linkedin.com/company/bonfire-advisory
    CJ: 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 Fiction
    4:26 CEO/CFO Tension
    7:08 Botching the Announcement
    8:15 How Staff Really React
    9:18 When Personal Life Collides With a Deal
    13:50 ARR vs. EBITDA
    17:58 What to Optimize Before a Sale
    18:50 Churn and Contract Renewal
    20:43 Strategics vs. PE
    27:46 Investment Banker Fee Structures
    29:09 What's Negotiable
    29:56 The Realtor Problem
    34:53 Big 4 vs. Regional Firms for Audit and QoE
    35:47 Negotiating Accounting Fees
    37:47 Deferred Revenue
    41:23 Warrants, Options, and Carta Cleanup
    44:02 QSBS: What CFOs Need to Know
    45:28 Quality of Earnings: Who Pays and Why
    47:44 What a QoE Actually Digs Into
    51:22 Why Deal Momentum Is So Hard to Stop
    53:47 The Waterfall
    58:19 Who Keeps Their Job
    61:31 Why Selling CFOs Feel Intimidated
    62:56 Prospect Theory
    65:28 Where to Find the Book
    #RunTheNumbersPodcast #MandA #CFOLife #SellingACompany #QualityOfEarnings
  • Run the Numbers

    Masterwork’s CFO Runs 12 AI Agents at Once | Nigel Glenday

    14/09/2026 | 46min
    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/rtn
    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/cj
    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/mostlymetrics
    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/cj
    Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/
    Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics
    EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups

    LINKS: 
    Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
    Guest: linkedin.com/in/nglenday
    Company: 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 Map
    18:50 Why CFOs Are Uniquely Positioned to Encode Context
    21:36 Making Data Cheap to Access
    28:55 Claude Code Over the Web App
    30:49 Building "The A-Team"
    35:24 Solving 300,000 K-1s with AI and Python
    42:26 Asking Better Questions Segment
    42:50 Adopting Campfire
    44:20 When Human Writing Beats AI

    #RunTheNumbersPodcast #AIforCFOs #FinanceLeadership #MasterworksArt #ContextEngineering
  • Run the Numbers

    How Oura Built a $1.4 Billion Business Around a Tiny Ring

    10/09/2026 | 34min
    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/metrics
    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/rtn
    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/cj
    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/mostlymetrics
    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/cj
    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/
    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/cLTxtAsN
    CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
    Mostly metrics: https://www.mostlymetrics.com

    TIMESTAMPS:
    0:00 Oura Files S1
    2:24 Key Revenue Stats
    3:35 Revenue Per Ring
    4:14 Gross Margin Breakdown
    5:31 The Weird $924M "Net Loss"
    6:11 Adjusted EBITDA and Cash Position
    7:20 Headcount and Bankers
    11:01 What Oura Actually Does
    13:46 Go-to-Market Channels
    15:57 Why Oura Rejects the "Fitness Tracker" Label
    16:49 Who's Actually Buying It
    21:26 Global Penetration Is Still Low
    21:54 The $84M Battery Problem
    22:56 Aggressive Growth Spend
    24:16 Samsung's Patent Complaint
    25:00 The Sleep Accuracy Class Action
    25:17 Former CEO Lawsuit
    25:52 Customer Concentration Risk
    26:31 Supply Chain and Tariff Exposure
    27:07 Clean Governance, No Material Weaknesses
    27:20 The Cap Table
    27:44 Oura's Massive Stock Buybacks
    29:29 The RSU Vesting Mechanics
    30:34 Tax Withholding on Settlement
    31:07 Valuation: $16B at 11x Revenue
    31:34 Who Do You Comp Oura To
    32:34 Miscellaneous Filing Details
    33:14 Final Take
  • Run the Numbers

    What 20 Years of Software Investing Says About AI | Matt Hedberg

    07/09/2026 | 51min
    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/metrics
    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/rtn
    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/cj
    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/mostlymetrics
    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/cj
    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/cLTxtAsN
    Guest: 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.
  • Run the Numbers

    Andy Ellis: How to Lead Without Becoming the Hero, the Villain, or the Bottleneck

    03/09/2026 | 1h
    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/cj
    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/metrics
    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/rtn
    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/cj
    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/mostlymetrics
    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/cLTxtAsN
    Guest: 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 Stories
    1:43 Welcome to Run the Numbers
    2:53 Andy's Book: 1% Leadership
    7:44 Rule 1: Don't Replace People Immediately
    14:04 Rule 2: Don't Become Indispensable
    16:02 How Andy Learned to Speak Finance
    22:35 Rule 3: Don't Tell Yourself Hero/Villain Stories
    26:59 The 5K Race Mindset Shift
    31:01 Rule 4: Don't Overspecify Delegation
    35:59 Rule 5: Don't Obsess Over Your Strengths
    38:23 The Six Leadership Disciplines
    43:45 The Vendor Rebuff Email
    47:45 Why Leaders Avoid Saying No
    50:28 Story: The Guinness Bartender Promotion
    53:52 When Metrics Get Gamed
    54:11 Asking Better Questions Segment
    59:07 Where to Get the Book
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Sobre Run the Numbers
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.
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