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Run the Numbers

CJ Gustafson
Run the Numbers
Latest episode

332 episodes

  • Run the Numbers

    The Stripe Guide to Pricing, Billing, and Quote-to-Cash with Wisam Hirzalla

    20/08/2026 | 54 mins.
    In this episode of Run the Numbers, CJ sits down with Wisam Hirzalla, Head of Product at Stripe Billing, to trace the full journey of a dollar—from product packaging and pricing through quoting, contracts, billing, tax, collections, and revenue recognition.

    SPONSORS:
    Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/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 It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down.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 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
    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/wisam-hirzalla-9b20a91/
    Company: https://stripe.com/
    CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
    Mostly metrics: https://www.mostlymetrics.com

    TIMESTAMPS:
    0:00 What Drives Billing Downstream
    1:41 Welcome to Run the Numbers
    2:37 Wisam's Path to "Queen of Billing"
    4:55 What Head of Billing at Stripe Entails
    5:45 Defining Quote-to-Cash
    7:50 Layer 1: Pricing and Packaging Mistakes
    14:46 Pricing Models Rising Because of AI
    18:11 Layer 2: Inside a Quote
    19:27 Why Enterprise Deals Get So Messy
    24:38 Layer 3: Contracting
    27:21 Layer 4: Billing
    30:15 Why Usage-Based Billing Is So Complex
    34:51 Tokens as a Pricing Unit
    36:57 Billing's Move Out of the ERP
    39:53 Layer 5: Provisioning and Entitlements
    43:36 Layer 6: Tax
    44:27 Layer 7: Getting Paid
    48:18 Layer 8: RevRec
    50:52 When Billing Stopped Being Back Office
    51:47 Asking Better Questions Segment
    52:28 Will AI Replace Finance Jobs
  • Run the Numbers

    The CFO-COO Is Coming: Meredith Finn of Front on the Future of Finance

    17/08/2026 | 54 mins.
    Front CFO & COO Meredith Finn joins CJ to explain why finance leaders are taking on more of the operator’s job. They break down the CFO-COO dual mandate, how Front funds new bets inside a mature SaaS business, why AI requires more coordination than simply handing everyone new tools, and how finance teams should think about the growing cost of AI.

    SPONSORS:
    Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/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/

    LINKS: 
    Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
    Guest: https://www.linkedin.com/in/meredithfinn1/
    Company: https://front.com/
    CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
    Mostly metrics: https://www.mostlymetrics.com

    RELATED EPISODES:
    Adam Swiecicki - CFO of Rippling
    https://youtu.be/JyGJVpmZNac
    Aurélien Nolf - CFO of Navan
    https://youtu.be/siwzJSRXAvY

    TIMESTAMPS:
    0:00 The CFO/COO Dual Mandate
    1:45 Welcome to Run the Numbers
    2:52 Front's In-House Podcast Studio
    3:41 Meredith's Investment Thesis on Front
    7:21 The "Portfolio Career" Analogy
    8:35 What She Had to Unlearn as an Operator
    13:13 Books on Strategy vs. Execution
    16:17 When a CFO Should Also Be COO
    18:27 What the COO Hat Actually Covers
    20:20 Where the Two Roles Conflict
    25:42 Budgeting for AI Token Costs
    29:16 Using Internal Usage as a Benchmark
    35:40 Funding a Series A Bet Inside a Series D Company
    38:04 Sizing Bets: Core, Adjacent, Moonshot
    40:04 The Secret to Re-Accelerating Growth
    41:46 Going Deeper, Not Wider
    43:18 What the Pricing Overhaul Taught Her
    47:30 Why Customer P&L Matters
    50:11 Lightning Round Begins
    51:32 Advice to Her Younger Self
    52:33 Front's Finance Tool Stack
    53:21 Craziest Expense Ever
    #RunTheNumbersPodcast #CFOLife #FinanceLeadership #AIinFinance #SaaSGrowth
  • Run the Numbers

    Xero’s CFO: Why Finance Is Taking On More of the Business

    13/08/2026 | 49 mins.
    In this episode of Run the Numbers, CJ Gustafson sits down with Xero CFO Claire Bramley to discuss how the CFO role is expanding beyond finance into strategy, operations, transformation, and technology. Claire also shares how she builds teams around her weaknesses, what small businesses actually want from AI, and why she views diversity as a business performance decision.

    SPONSORS:
    Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/
    Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/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

    LINKS: 
    Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
    Guest: 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 Intro
    3:00 Xero and CJ's History With It
    4:12 Xero's Size and Scale Today
    5:10 The Expanding CFO Role
    7:06 Hiring Experts You're Not
    8:47 Imposter Syndrome
    11:00 Getting Better at Asking Questions
    15:04 Asking the "Stupid Question"
    16:21 Finance as the Corporate Junk Drawer
    17:48 The Trial Period Idea
    18:24 Tripwires: Leading Indicators for CFOs
    25:35 AI Hype vs. Main Street Reality
    26:44 What Small Business Owners Actually Want
    28:45 What Big Corps Underestimate
    31:10 Trust as a Competitive Moat
    33:45 Why the Line Is Thinner for Small Biz
    35:12 AI Inside Claire's Finance Team
    37:23 AI for Investor Relations
    39:28 Diversity as Capital Allocation
    42:07 A Decision Diversity Changed
    44:45 Lightning Round Begins
    46:06 Advice to Her Younger Self
    48:49 Craziest Expense Ever
    #RunTheNumbersPodcast #CFOLife #FinanceLeadership #AIinFinance #WomenInFinance
  • Run the Numbers

    A CFO Explains Private Jets

    10/08/2026 | 34 mins.
    On this episode of Run the Numbers, CJ and Ben trace corporate private jets from Sam Walton’s scrappy two-seater to Alex Karp’s $17 million jet bill. They break down when flying private actually makes business sense, how jets hit the balance sheet, the tax and accounting implications, what companies disclose to investors, and when executive travel crosses the line from productivity tool to corporate excess.

    SPONSORS:
    Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/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

    LINKS: 
    Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
    CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
    Mostly metrics: https://www.mostlymetrics.com

    RELATED EPISODES:
    Jersey Mike’s IPO: The $4.2B Sandwich Machine
    https://youtu.be/ZL6AbqHI-0g

    TIMESTAMPS:
    0:00 Fly Like a G6
    0:29 $17M on jets: Alex Karp guess
    1:16 Sam Walton starts it all
    2:49 The yellow legal pads
    4:37 Walmart Aviation founded (1968)
    5:14 Piston to Bombardier jets
    6:51 Walmart's modern jet fleet
    8:13 Where it hides in SEC filings
    9:25 SEC Reg S-K Item 402
    13:37 Gulfport Energy scandal
    14:42 Tyco: Kozlowski & Schwartz
    16:57 When jets are actually useful
    17:55 P&L vs. balance sheet treatment
    18:40 PP&E and depreciation basics
    19:04 Off-balance-sheet leases
    19:28 The chartering loophole
    19:54 "Uber Jet" fractional ownership
    23:14 How activists hunt jet spend
    23:36 Flight registries & tail numbers
    24:13 Jack Sweeney vs. Elon Musk
    25:00 What top companies spend
    25:18 Walmart's fleet is #1
    26:17 Charter vs. lease vs. own
    29:02 Should we care? 3 angles
    30:06 Angle 2: opportunity cost
    30:59 Angle 3: company size
    31:42 General Electric's shadow jet
    32:50 Back to Alex Karp
    34:02 Credits
    #RunTheNumbersPodcast #PrivateJets #CorporateFinance #ExecutivePerks #CFOLife
  • Run the Numbers

    The Business of Saving Lives: Inside RapidSOS

    06/08/2026 | 49 mins.
    On this episode of Run the Numbers, CJ Gustafson sits down with Richard Haram, VP of Finance at RapidSOS, to unpack how finance supports a public safety AI platform that helps 911 operators and first responders act faster. They cover building AI fluency, combining FP&A with BI, monetizing vertical software, integrating acquisitions, and the leadership lessons Richard carried from entrepreneurship.

    SPONSORS:
    Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/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 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

    LINKS: 
    Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
    Guest: 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 Intro
    3:10 What RapidSOS does
    4:59 CJ’s own car accident
    5:33 What's broken about 911
    6:50 Who's the actual customer
    7:46 How RapidSOS monetizes
    10:13 Sponsors — Pulley | Rillet | Maximor
    13:27 Too much data, too much noise
    16:35 Data pollution and trust
    18:24 The data stack early on
    19:25 Should BI have come sooner?
    20:45 The framework: questions to decisions
    22:43 Building a data culture
    23:58 Sponsors — Brex | Anrok | RightRev
    26:51 Bottoms-up vs. top-down AI
    28:42 Inspiration, not training
    32:24 The three-phase AI progression
    33:31 Founding an AV company at 8
    35:37 Giving people room to grow
    38:12 Depending on heroes
    39:55 Working under founder personalities
    41:23 Do startups undervalue what they sell
    42:48 A price hike, zero churn
    43:24 Signs you're underpricing
    44:57 Lightning round
    45:03 Screwed up: refreshed data before a demo
    47:15 Advice to younger self
    47:41 Finance software stack
    48:37 Craziest expense: personal gas
    49:29 Credits
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About 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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