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Run the Numbers

CJ Gustafson

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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  • 42 episodes
  • a few times a week
  • Avg 45 min
  • English

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  • Today · 50 min

    Why Databricks’ Sid Kumar is Always Planning

    In this episode of Run the Numbers, CJ welcomes back Sid Kumar, who has led go-to-market through perpetual, cloud, SaaS, and consumption models at CA, AWS, HubSpot, and now Databricks. They cover how consumption changes the sales org, why customer success has an identity crisis, how to build a commission stack, and what ARR actually means. Sid also shares how AI is reshaping capacity planning and why he thinks annual planning is giving way to continuous planning. — SPONSORS: Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made. Go to abacum.ai/mostly-metrics. 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 It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down.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 Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out www.fidelityprivateshares.com 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 Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to www.cloudcapital.co 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 Craig on Linkedin: linkedin.com/in/craig-bealmear-a375573 Oklo: https://oklo.com/ CJ: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — TIMESTAMPS: 0:00 Cold Open 2:52 Go-to-Market 5:05 Perpetual, SaaS, Consumption 7:01 The Contract Isn’t the Moment of Truth 10:24 A Different Kind of AE 17:41 Customer Success’s Identity Crisis 20:23 Hunter vs. Farmer 22:44 Motion Specialization 23:50 Building the Commission Stack 28:07 CAC and LTV 29:54 What ARR Means 33:44 Pattern Matching With Data 38:13 Forecasting 38:59 Always Be Planning 41:10 AI and Capacity Planning 43:48 Will AI Change Sales Ops? 46:16 The Player-Coach Is Back 46:44 Getting Hands-On With AI 48:08 Hot Take on Annual Planning #RunTheNumbersPodcast #Databricks #GoToMarket #SalesOps #ConsumptionPricing

  • Thursday · 32 min

    Oklo CFO on Leading Through Deepwater Horizon | Craig Bealmear

    In this episode of Run the Numbers, recorded live at Brex Mode in Chicago, CJ sits down with Craig Bealmear, CFO of Oklo, who spent nearly 30 years at BP before moving into nuclear. They cover raising billions before meaningful revenue, why cash matters more than the P&L, and how he hires the finance team Oklo will need two years from now. Craig also looks back at leading through the Deepwater Horizon crisis. — SPONSORS: Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made. Go to abacum.ai/mostly-metrics. 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 Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out www.fidelityprivateshares.com 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 Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to www.cloudcapital.co 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 Craig on Linkedin: linkedin.com/in/craig-bealmear-a375573 Oklo: https://oklo.com/ CJ: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — TIMESTAMPS: 0:00 Cold Open 2:38 What Oklo Does 3:38 From BP to Nuclear 6:03 The Power Behind the AI Stack 7:47 Unconstrained Demand 12:38 Risks 13:50 Running a Pre-Revenue Company 14:57 The Say-Do Ratio 17:41 Asking the Dumb Questions 18:13 Raising Capital Before the Projects 21:15 Cash Management Pillars 25:05 One-Way vs. Two-Way Decisions 26:11 Defining Capability 27:35 Hiring for Two Years Out 28:07 Forecasting the Team 8 Quarters Out 30:07 Deepwater Horizon 31:46 Leading Through a Crisis 32:19 Wrap Up #RunTheNumbersPodcast #Oklo #Nuclear #CFO #BrexMode

  • Tuesday · 18 min

    Token Series Part 2 | Finance's ChatGPT moment: MCP, Harness, and Headless Explained (simply)

    In Part 2 of our Token Series with Tabs, CJ and Ali Hussain ask how much AI is too much in finance. They cover why finance may be the most AI-forward function after product and engineering, how MCP became its “ChatGPT moment,” and why headless agents need a leash. They also get into where to start with governance and why deterministic layers still matter. — SPONSORS: Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at ⁠https://www.tabs.com⁠ — LINKS: Mostly Talent: ⁠⁠ https://mostlymetrics.typeform.com/to/cLTxtAsN⁠⁠ Guest: ⁠⁠⁠⁠ linkedin.com/in/ali-hussain786⁠ Company: ⁠⁠ www.tabs.com⁠ CJ: ⁠⁠ https://www.linkedin.com/in/cj-gustafson-13140948/⁠⁠ Mostly metrics: ⁠⁠ https://www.mostlymetrics.com⁠⁠ — TIMESTAMPS: 0:00 Cold Open 1:05 Why CFOs Ask About Org Design 2:25 Finance Is the Most AI-Forward Team 3:43 MCP: Finance’s ChatGPT Moment 5:08 Laying Tracks for Agents 5:53 Vendors, Employees, Customers 6:51 MCP, Harnesses, and Headless Agents 8:34 The New Finance Operating System 11:50 Governing AI in Finance 12:12 Where to Start: Billing and Collections 13:51 Will Deterministic Layers Survive? 14:51 Build vs. Buy 16:28 Why Revenue Work Is So Hard 18:11 Next Up: Who Foots the Bill? #RunTheNumbersPodcast #Tabs #CFO #AI #AITokens

  • October 19 · 49 min

    Brex's CFO on the Weekend SVB Collapsed | Erica Dorfman

    Episode Description: In this episode of Run the Numbers, CJ sits down with Erica Dorfman, CFO of Brex, to trace her path from capital markets at SoFi to product to the CFO seat. They cover why Brex moved away from lending, what happened behind the scenes during the SVB collapse, and how Erica keeps reinventing her role and her team as the company scales. — SPONSORS: Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to www.cloudcapital.co 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 Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made. Go to abacum.ai/mostly-metrics. 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 Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out www.fidelityprivateshares.com 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 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 Erica on Linkedin: linkedin.com/in/erica-dorfman-4034b717 Brex: www.brex.com CJ: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — TIMESTAMPS: 0:00 Cold Open 2:24 Swimming and the CFO Mindset 6:03 The Columbia Finance Mafia 7:48 The Physics of a Business 11:16 VP of Cash at Brex 12:40 How Banking Partnerships Work 17:58 Why Brex Moved Away From Lending 19:23 Great Adjacency vs. Distraction 21:31 AI Auditing Every Transaction 23:00 Operating Through Chaos at SoFi 25:45 The SVB Weekend 29:00 Crisis Meets Opportunity 37:31 Asking “Stupid” Questions 39:44 Rebuilding the Team 43:33 Killing Meetings 46:05 Erica’s Biggest Mistake 47:08 Advice to Her Younger Self 47:36 Brex’s Finance Tech Stack 48:37 Craziest Expense Ever #RunTheNumbersPodcast #Brex #CFO #Building #FinanceLeadership

  • October 15 · 37 min

    Former Netflix CFO Breaks Down Return on Compute | Jim Cook

    In this episode of Run the Numbers, CJ welcomes back Jim Cook, a multi-time CFO (Intuit, Netflix, Mozilla) turned coach, author, and newsletter writer. They dig into “return on compute,” the metric Jim believes every finance leader needs in their vocabulary, and why surprise AI bills echo the early days of the cloud. They cover how to budget for tokens, the “frontier convergence” idea for ramping compute spend by role, and why revenue per compute may join revenue per headcount on the CFO scorecard. — 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 Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to www.cloudcapital.co 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 Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made. Go to abacum.ai/mostly-metrics. 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 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 Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out www.fidelityprivateshares.com — LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN Jim on Linkedin: linkedin.com/in/cookflix Benchboard: https://www.benchboard.com/ CJ: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — TIMESTAMPS: 0:00 Welcome Back, Jim Cook 2:56 Return on Compute 5:51 The $500K Surprise Bill 8:25 Do Execs Know Their Token Usage? 10:05 Tagging Compute Like Cloud Costs 12:03 Budgeting for Tokens 13:19 Revenue per Compute 14:45 The Modern CFO Framework 15:50 What Strategy Really Means 17:44 Communication and Influence 22:27 Lead With a Thesis 24:05 Speaking Up in the Boardroom 26:04 Better Questions with EY 28:11 Where to Find Jim #RunTheNumbersPodcast #ReturnOnCompute #CFO #AI #FinanceLeadership

  • October 12 · 48 min

    Inside the Food52 Bankruptcy | Heidi Robinson

    In this episode of Run the Numbers, CJ sits down with Heidi Robinson, former CFO and COO of Food52, for one of the wildest CFO stories the show has featured. Heidi joined expecting to lead a modest turnaround and within weeks realized the company was in far deeper trouble than anyone understood. She walks through being the newest executive in the room and having to deliver that news and the Monday evening a lender swept the company's cash without warning. — SPONSORS: Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out www.fidelityprivateshares.com 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 Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to www.cloudcapital.co 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 Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made. Go to abacum.ai/mostly-metrics. 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 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/heidilrobinson CJ: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — TIMESTAMPS: 0:00 Cold Open 2:29 Joining Food52 3:45 Food52's Three Brands 6:14 Building a Cash Flow Model 7:25 Delivering the Worst News 8:09 A Path Without Bankruptcy? 9:05 The Cash Sweep 13:44 The Scramble 18:30 Selling at 60% Off 19:45 Working Through the Holidays 20:10 Filing Chapter 11 21:48 Chapter 7 vs. 11 23:05 The Headline Objective 23:33 The Stalking Horse Bidder 26:17 Meet the Cast29:41 Testifying Under Oath 30:50 The Independent Board Member 35:27 The Live Auction 39:06 Bidding Like Poker 40:50 The Payout Waterfall 44:24 Better Questions with EY 44:41 Rethinking Risk 46:00 CFO/COO Convergence #RunTheNumbersPodcast #CFOs #Food52 #Bankruptcy #FinancePodcast

  • October 8 · 1 hr 6 min

    Robinhood's CFO on Refounding & the Art of Capital Allocation | Shiv Verma

    In this episode of Run the Numbers, CJ sits down with Shiv Verma, CFO of Robinhood, to unpack the company's 2022 "refounding". They dig into why Shiv personally signs off on every headcount and marketing dollar at a $100B+ company, and how Robinhood's capital allocation philosophy — no loss leaders, minimal variable costs, and a hard $100 million ARR bar for new products — shapes everything from prediction markets to private-market investing. — 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 Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out www.fidelityprivateshares.com 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 Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to www.cloudcapital.co 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 Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made. Go to abacum.ai/mostly-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/shiv-verma-6408249 Company: www.robinhood.com CJ: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — TIMESTAMPS: 0:00 Intro 2:21 The 2022 Refounding 8:46 Using NPS 17:53 Moving to a GM Model 19:58 Finance Partners 17:49 Killing Committees for DRIs 20:04 Headcount Requests 27:02 RPM Teams and Efficiency 32:27 The Art of Capital Allocation 33:34 Core, Scaling, and New Seeds 37:07 Funding a New Idea 38:17 Killing OKRs 44:59 No Loss Leaders 48:36 Building Prediction Markets Fast 51:26 Why Shiv Hates Variable Costs 53:37 Market Share Over Revenue 55:59 Forecasting a Volatile Business 59:53 Shiv's Biggest Mistake 1:02:03 Lessons from the Oakland A's 1:04:04 Advice to His Younger Self 1:04:48 Finance Tech Stack 1:05:30 Craziest Expense

  • October 6 · 14 min

    Token Series Part 1 | How AI Created a New Budget

    This is Part 1 of our new Token Series with Tabs. CJ calls up Ali Hussain to dig into one of the fastest-growing, least-understood line items on the P&L: AI inference and token spend. They debate whether AI costs ultimately belong to the CTO or the CFO, why the shift from "experimentation budgets" to real operating costs is forcing companies to rethink ownership, what's actually different about AI spend compared to the early cloud transition, and how tools like OpenRouter (acquired by Stripe) and Ramp's new offering are approaching the problem from opposite ends of engineering vs. finance. — Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com — LINKS: Mostly Talent: ⁠https://mostlymetrics.typeform.com/to/cLTxtAsN⁠ Guest: ⁠linkedin.com/in/ali-hussain786 Company: ⁠www.tabs.com CJ: ⁠https://www.linkedin.com/in/cj-gustafson-13140948/⁠ Mostly metrics: ⁠https://www.mostlymetrics.com⁠ — TIMESTAMPS: 0:00 Cold Open 1:11 From Experimentation Budgets to Real AI Costs 2:43 Who Owns AI Spend Inside a Company? 4:12 Lessons from the Cloud Transition 5:55 Why AI Costs Are Different from Cloud 7:51 AI as "Electricity Through the House" 8:42 Paying for 5 to 10 LLM Providers 9:58 OpenRouter vs. Ramp: Two Approaches 11:47 What the Finance Stack for AI Spend Should Look Like 13:34 Passing AI Costs on to Customers

  • October 5 · 53 min

    Why Owning Your Data Is the New Moat | Primary Venture's Emily Man

    In this episode of Run the Numbers, CJ sits down with Emily Man of Primary Ventures to map out where value actually accrues in the AI economy. They break down the 5 layers of the AI stack and why Emily believes the next era of AI adoption will be driven by diffusion through apps rather than smarter models alone. — SPONSORS: Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made. Go to abacum.ai/mostly-metrics. 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 Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out www.fidelityprivateshares.com 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 Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to www.cloudcapital.co 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/emily-man-02a1a486 Company: https://www.primary.vc/ CJ: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — TIMESTAMPS: 0:00 Cold Opens 1:12 Meet Emily Man, Primary Ventures 2:01 What's Exciting in Venture Right Now 3:09 The 5 Layers of the AI Stack 4:08 Where Funding Has Focused So Far 5:54 Diffusion Through Apps 9:30 "Enough" Intelligence 17:11 Payroll vs. Compute Ratio 23:01 Alex Karp and "Owning Your Weights" 24:05 On-Prem vs. Cloud, Again? 30:53 Models vs. Loops 32:34 Software Goes Headless 34:14 Pre-2022 SaaS Companies 36:29 The Roadkill Bucket 41:42 The Vibe-Coding Backlash 44:55 Objectivity vs. Subjectivity 48:03 When AI Agents Talk to Each Other 49:43 Creating Alpha Without Being AI-Native 51:01 Better Questions, Brought to You by EY 51:16 The Future CFO Tech Stack #RunTheNumbersPodcast #AIforCFOs #FinanceLeadership #Zuora #GoingPrivate

  • October 1 · 47 min

    Zuora’s COFO On Going Private and Pricing AI | Todd McElhatton

    In this episode of Run the Numbers, CJ sits down with Todd McElhatton, CFO of Zuora, for a deep cut on pricing, packaging, and value in the age of AI. They dig into how companies are figuring out whether to charge for AI at all, why token-based budgets are starting to sit alongside headcount budgets, and why AI may be increasing — not decreasing — the value of deep expertise. — SPONSORS: Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics Abacum puts your actuals, forecasts, models, and business context in one place, so you can update the plan, run scenarios, and answer "why did this change?" without rebuilding the story from six spreadsheets and a Slack thread. Connect your source systems, keep models and assumptions aligned, and give leaders trusted answers while decisions are still being made. Go to abacum.ai/mostly-metrics. 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 Fidelity Private Shares gives founders the structure and simplicity to focus on what actually matters - building your company. If your startup needs a little extra support (and let’s be honest, who doesn’t need a little help now and then), then you’re in for a pleasant surprise with Fidelity. If you stay investor ready, you don’t have to get investor ready. Check out www.fidelityprivateshares.com 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 Cloud Capital helps you say goodbye to on-demand rates for cloud. Committing more cuts the rate you pay for cloud infrastructure by 20–60%. Commit wrong and you pay for capacity you'll never use. Cloud Capital underwrites that risk, so you capture the savings of deeper commitments without locking in architecture or putting engineers on it. Go to www.cloudcapital.co 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/todd-mcelhatton-2140761 Company: www.zuora.com CJ: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — TIMESTAMPS: 0:00 Intro 1:15 Meet Todd 2:24 Debating Price 7:33 Is Software "Going Headless"? 9:18 Is AI Increasing the Value of Experts 9:58 Hiring Specialists vs. Generalists 16:49 Rethinking the Budget Envelope 26:56 Time to Value 31:20 Forward-Deployed Engineers 35:20 Parallels Between On-Prem-to-Cloud 36:10 Rethinking Strategy 37:07 Avoiding the Sunk Cost Trap 38:58 The Art of Pivoting 40:12 VMware 41:31 Experimenting With AI 42:33 What Private Boards Bring 43:13 Short-Term Pain 43:45 One-Way Doors vs. Two-Way Doors 44:57Long-Ass Lightning Round 45:04 Biggest Career Mistake 45:36 Advice45:56 Finance Tech Stack 46:43 The Craziest Thing Expense #RunTheNumbersPodcast #AIforCFOs #FinanceLeadership #Zuora #GoingPrivate

  • September 28 · 49 min

    LiveRamp’s CFO Rebuilt Pricing From Scratch | Lauren Dillard

    CJ sits down with Lauren Dillard, CFO of LiveRamp, whose path to the CFO seat ran through investor relations, communications, and even a year as interim CMO. They dig into why storytelling and influence matter as much as technical finance chops, how LiveRamp tore down and rebuilt its entire commercial model — collapsing 25+ usage metrics into 5 and inventing the "token" along the way. — SPONSORS: Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/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 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: https://www.linkedin.com/in/lauren-russi-dillard-25502424/ Company: https://www.liveramp.com CJ: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — TIMESTAMPS: 0:00 Cold Open 1:18 Intro 1:29 Meet Lauren Dillard 4:48 Lauren's Path to CFO 5:06 The "Wrong" Career Move 7:48 Why Storytelling Matters 9:41 Turning the Answer Into Action 10:33 People Plus AI 14:50 Pricing Is a Strategy Exercise 16:43 Rebuilding a Commercial Model 22:29 Simplifying Quote-to-Cash 23:29 Where the "Token" Came From 28:48 Selling a New Pricing Model 29:27 Balancing New Logos 30:17 Upmarket or Downmarket? 34:17 Where Finance and HR Disagree 36:07 The Biggest Mistake 38:23 Will It Make the Boat Go Faster? 42:27 Lessons from the NBA 44:25 Lauren's Biggest Misstep 46:27 Finance Tech Stack 47:42 Craziest Expense #RunTheNumbersPodcast #AIforCFOs #FinanceLeadership #MasterworksArt #ContextEngineering

  • September 24 · 34 min

    The NScale IPO | A Neocloud S1 Breakdown

    Nscale just filed its S-1 to go public on the NYSE — and it might be the wildest IPO filing of the year. This UK-based "NeoCloud" is only 2 years old, is gross margin negative, started life as a crypto miner, and has somehow locked up over $100 billion in contracted value from Anthropic and Microsoft. CJ breaks down the entire S-1 line by line: what a NeoCloud actually is, how Nscale's "power to token" strategy works, why Nvidia shows up as its supplier, investor, guarantor, AND customer, and whether this is a durable business or a well-timed arbitrage on the AI compute shortage. — 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 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 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 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 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 Company: https://www.nscale.com/ CJ: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — TIMESTAMPS: 0:00 Cold Open 0:53 Intro: Nscale Files to Go Public 2:40 WTF Is a NeoCloud? 4:11 The 5 Layers of the AI Stack 5:55 Landlord vs. Hotel: Nscale's Two Businesses 7:21 How Take-or-Pay Contracts Work 8:28 Sponsor Break 11:43 Breaking Down the Financials 15:37 What's a Contract Actually Worth? 18:45 Is This Just Nvidia Vendor Financing? 20:58 Sponsor Break 22:54 Medium-Term Arbitrage or Durable Company? 24:30 5 Potential Red Flags 27:08 How Does the CEO Get Paid? 28:04 Who's on the Board? 28:26 Is This the CoreWeave of the UK? 31:09 Miscellaneous Filing Oddities 33:31 Final Take #Nscale #IPO #NeoCloud #S1Breakdown #AIInfrastructure

  • September 21 · 51 min

    How Media Actually Makes Money | Blake Saunders

    In today’s Run the Numbers, CJ sits down with Blake Saunders, founder and managing director at Core Advisors (an investment bank focused on media) and founder of The Joint, to go deep on how media companies actually make money — and how that's changing fast. If you're anywhere near advertising, media, or content monetization, this one's a masterclass. — 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 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 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 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/blakesaunders Company: https://coreadvs.com/ CJ: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — TIMESTAMPS: 0:00 Cold Open and Intro 1:17 Welcome Back: Meet Blake Saunders 3:11 What Does "Media" Even Mean Today? 3:24 AI and LLMs 6:13 How Media Companies Make Money 7:32 Subscriptions vs. Ads vs. Events 8:54 Why Events Are the Riskiest Ad Dollar 9:48 B2B vs. B2C 14:25 Why Advertising Gets Such a Bad Rap 17:58 The Hulu Paradox 20:50 Built to Hold vs. Built to Sell 27:10 Content Decay and the Monetization Mismatch 29:08 Are IP Libraries Becoming Valuable 34:39 How Big-Name Podcast Deals Get Structured 37:50 Bundling, Unbundling, and Subscription Fatigue 39:08 The Bending Spoons Trade 40:20 Inside a Private Equity Value Creation Plan 41:56 The Content-to-Commerce Playbook 44:50 How Narrative-Driven Is Media M&A? 46:49 7 Moments a Deal Feels Dead 49:00 Farewell

  • September 17 · 1 hr 6 min

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

    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

  • September 14 · 46 min

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

    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

  • September 10 · 34 min

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

    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

  • September 7 · 51 min

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

    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.

  • September 3 · 1 hr

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

    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

  • August 27 · 54 min

    40 Years of IPOs with Jay Ritter: What the Data Actually Says

    In this episode of Run the Numbers, CJ sits down with Jay Ritter. They break down what Apple, Nvidia, the dot-com boom, and today’s AI giants can teach us about IPOs, why companies leave money on the table on day one, why firms stay private longer, and what the data actually says about long-term IPO performance. — 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 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/jay-ritter-1323861/ Company: https://www.ufl.edu/ CJ: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — TIMESTAMPS: 0:00 Preview and Intro 3:10 Meet Jay Ritter, Mr. IPO 4:02 The Original 1983 Question 5:08 PCs, Internet, and AI Compared 9:36 Network Effects 14:46 Sitzfleisch: Outlasting the Field 16:10 Where Have All the IPOs Gone 23:29 IPOs as Relationship-Building 26:31 Why Investors Tolerate Founder Control 29:16 Dual-Class Stock's Origins 30:21 How Jay's Thinking Evolved 31:36 Why Boards Don't Get Angry 34:39 Banks' Real Client: Institutions 37:08 Book Building 38:56 Why Direct Listings Haven't Taken Over 39:57 What Goldman Is Really Selling 41:57 Sentiment vs. Long-Term Performance 43:13 Does Staying Private Help Society 49:35 Asking Better Questions with EY 52:12 Are Markets Efficient

  • August 24 · 45 min

    How AI Is Rewriting Product-Market Fit, Pricing, and Go-to-Market

    CJ sits down with Rebecca Schwartz of Tabs, Fred Havemeyer of Fleet AI, and Rahul Rekhi of Rogo for a live conversation about what it actually takes to build an AI-native 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/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 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 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 https://www.tabs.com/ https://fleetai.com/ https://www.rogo.com/ CJ: https://www.linkedin.com/in/cj-gustafson-13140948/ Mostly metrics: https://www.mostlymetrics.com — TIMESTAMPS: 0:00 Preview and Intro 1:16 Welcome to Run the Numbers 3:17 Meet the Panel: Rebecca, Fred, Rahul 9:52 How Rogo Found PMF 13:47 How Tabs Found PMF 14:51 Growth Rates: Headcount and Revenue 16:23 The Real Hiring Constraint 17:21 What "Forward Deployed" Actually Means 18:53 What's Blocking AI Adoption Now 20:19 How Sales Hiring Has Changed 24:34 How Go-to-Market Has Changed 25:28 Pricing Models: Then vs. Now 28:18 Tabs' Pricing Evolution 29:20 What the Finance Team Looks Like 31:00 How Far You Can Push Outsourced Accounting 32:43 Managing AI Gross Margins 35:07 The North Star Metric for AI Companies 37:02 Token Spend vs. Per-Seat Pricing 39:34 Asking Better Questions: What Counts as ARR 41:38 Biggest Bug in Cash to Collections 43:05 Closing Advice for Founders

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