Run the Numbers

Check out Mostly Growth and get episodes early. Available on all platforms.* YouTube* Spotify* AppleIn this episode of Mostly Growth, CJ Gustafson, Kyle Poyar, and Ben Hillman dive into the question on everyone’s mind: are we in an AI bubble? What starts as a lighthearted riff on the U.S. Postal Service launching a podcast quickly spirals into a sharp, funny breakdown of today’s AI hype cycle — from Nvidia, OpenAI, and AMD trading money and GPUs in a trillion-dollar feedback loop, to startups burning cash chasing “AI-powered” everything. The trio share real examples of when AI helps and when it backfires (including one newsletter that totally tanked), debate whether companies are over-optimizing for automation, and laugh through the absurdity of the hype while grounding it in practical insights on product, finance, and growth.Timestamps:00:00 Preview and Intro00:14 Are We in an AI Bubble?00:44 The AI Feedback Loop: Nvidia, OpenAI, and AMD01:00 Perplexity, We Caught You (Again)02:18 The USPS Podcast and the End of Original Ideas04:24 How the Team Actually Uses AI at Work06:07 CJ’s DIY Dunning Saga08:38 When Automation Goes Too Far10:49 The Perplexity Gaslight Moment13:27 AI vs. AI: Outsmarting Resume Screeners16:09 What Recruiters Really Think of AI Resumes17:17 The Chief of Staff Hiring Story19:15 Is AI Adoption Already Slowing Down?22:42 The “Crossing the Chasm” Moment for AI Tools26:22 Bundling AI Like Streaming Services28:49 Everyone’s Paying Everyone: The Circular AI Economy31:15 Betting Big on AGI and Data Centers34:09 The Margin: AI Erotica and Peak Absurdity35:23 OpenAI’s Token Leaderboard and Other Blunders41:43 What Kyle Tried This Week: Building an AI Agent44:52 Wrap-Up and OutroEpisodes Referenced:5,762 Job Applications. Zero Offers.Episodes Referenced:5,762 Job Applications. Zero Offers.Why Only 2% of Startups Make ItThe War for Talent is just getting started | Joe FloydLinks:https://usps-mailin-it.simplecast.com/https://i.imgflip.com/a92oy5.jpghttps://tabs.inc/webinar/tabs-agenthttps://www.nytimes.com/2025/10/07/business/ai-chatbot-prompts-resumes.html?_bhlid=1b5906cdc6781a738a150d9c32f846ebf11fc318https://substack.com/home/post/p-175615945https://ramp.com/data/ai-index?utm_source=econlab.substack.comhttps://medium.com/@samuelvandeth/crossing-the-chasm-162802d1cf27https://x.com/TrungTPhan/status/1922669292929024017/photo/1https://x.com/zerohedge/status/1977902195472322620?s=42https://topline.beehiiv.com/p/the-era-of-haves-and-have-notshttps://www.bbc.com/news/articles/cpd2qv58yl5ohttps://www.linkedin.com/posts/cj-gustafson-13140948_imagine-getting-called-into-your-cfos-office-activity-7381681514532458496-NOqa/https://fortune.com/2025/10/01/red-lobster-ceo-damola-adamolekun-comeback-plan-bankruptcy/https://fortune.com/2024/11/13/red-lobster-ceo-damola-adamolekun-says-endless-shrimp-is-never-coming-back/#https://www.relay.app/Today’s podcast is brought to you by MetronomeYou just launched your new AI product. The new pricing page looks great. But behind it? Last-minute glue code, messy spreadsheets, and running ad-hoc queries to figure out what to bill. Customers get invoices they can’t understand. Engineers are chasing billing bugs. Finance can’t close the books.With Metronome, you hand it all off to the real-time billing infrastructure that just works—reliable, flexible, and built to grow with you. We turn raw usage events into accurate invoices, give customers bills they actually understand, and keep every team in sync in real time.Whether you’re launching usage-based pricing, managing enterprise contracts, or rolling out new AI services, Metronome does the heavy lifting so you can focus on your product, not your billing.That’s why some of the fastest-growing companies in the world, like OpenAI and Anthropic, run their billing on Metronome.Visit metronome.com to learn more. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ Gustafson sits down with Ivan Makarov, Operating Partner at Andreessen Horowitz and former VP of Finance at Webflow, to explore what it takes to build a finance function from scratch inside a fast-growing startup. Ivan shares lessons from the trenches—how to decide between outsourcing and hiring in-house, what makes a great first finance hire, and why early-stage companies often run out of cash before they run out of ideas. He also dives into fundraising pitfalls, audit readiness, and the tools that make up a modern finance stack. Beyond the spreadsheets, Ivan opens up about the shift from operator to venture partner, the value of helping founders avoid his past mistakes, and what makes an offsite actually work.—LINKS:Ivan Makarov on LinkedIn: https://www.linkedin.com/in/ivansmakarov/Andreessen Horowitz: https://a16z.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:Webflow’s VP Finance Ivan Makarov on Understanding Startup Equity:Portfolio Operations: This Is What You Actually Have To Do To Make Sure a Company Is Successful:Brex COO/CFO Michael Tannenbaum on Taking Risks996 Culture, Exploding AI Bills & SaaS Chaos—TIMESTAMPS:(00:00:00) Preview, Intro(00:01:18) Meet Ivan Makarov of Andreessen Horowitz & Episode Setup(00:02:39) Sponsor – Tipalti | Aleph | Rillet(00:06:51) From Webflow to Andreessen: Becoming an Operating Partner(00:09:19) When and Why Founders Hire Their First Finance Leader(00:12:52) Hiring Early in Complex or Regulated Industries(00:13:58) The First Finance Hire in 2025 vs. 2015(00:15:46) Sponsor – Fidelity Private Shares | Mercury | RightRev(00:19:02) The Many Hats of Finance Leaders & The Rise of RevOps(00:24:55) What Founders Look For: Startup DNA and Work Ethic(00:26:05) Grind Culture, Return to Office, and New Expectations(00:28:20) From BizOps to RevOps: How Finance Roles Are Evolving(00:31:57) The First 12 Months of a Finance Leader’s Playbook(00:35:05) Choosing Audit Partners and Avoiding Hidden Costs(00:36:32) Why Startups Really Fail — Running Out of Cash(00:39:16) Cash Controls, Banking Diversification, and Fraud Prevention(00:43:48) Fundraising Red Flags: Metrics, Definitions, and Diligence(00:47:50) 409A Valuations, Equity Clarity & Candidate Questions(00:50:09) The Modern Finance Tech Stack & Gen 3 Tools(00:55:05) AI’s Impact: Replacing Labor, Not People(01:00:00) Offsites, Team Building & The Future of Finance Leadership(01:02:28) Wrapping Up: Reflections, Gratitude & Closing Credits—SPONSORS:Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metricsFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.#RunTheNumbersPodcast #StartupFinance #VentureCapital #CFOInsights #Leadership This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode, CJ sits down with Joe Floyd, General Partner at Emergence Capital, for a candid conversation about the venture landscape reshaped by AI. They unpack how acqui-hires are rewriting the social contract between founders and investors, why AI engineers are commanding “boy band money,” and how SaaS playbooks are being torn up and rebuilt in real time. Joe explains the economics of AI-native startups — from circular capital flows to model-provider costs — and explores whether the next trillion-dollar private company could come from this new wave. Along the way, they discuss valuation frenzy, headcount discipline, and why curiosity might be the most valuable skill in tech today.—LINKS:Joe Floyd on LinkedIn: https://www.linkedin.com/in/joefloyd/HarbourVest Partners: https://www.emcap.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:Why Fundraising Has Slowed Down: Insights from Emergence Capital’s Benchmarking Report: From Credit Karma to Notion: CFO Rama Katkar on Leading Finance Through Every Growth Stage:—TIMESTAMPS:(00:00:00) Preview and Intro(00:00:54) Opening and Episode Overview(00:02:53) Sponsor – RightRev | Tipalti | Aleph(00:07:07) Back to the Office and Startup Pace in San Francisco(00:08:40) AI Tooling Experiments and the Risk of Short-Term Hype(00:10:19) Building Stickier AI Products and Competing in Crowded Markets(00:12:27) SaaS Moats, Product-Market Fit, and the AI Shift(00:14:00) How Productivity Platforms Use AI To Stay Sticky(00:15:58) Continuous Authentication and the Next Wave of Security Tech(00:16:36) Sponsor – Rillet | Fidelity Private Shares | Mercury(00:19:54) Acqui-Hires, the Social Contract, and the War for AI Talent(00:22:42) Stock-Based Comp and the Economics of Attracting Engineers(00:24:39) The New Go-to-Market Playbook and Curiosity as a Superpower(00:27:59) AI’s Impact on Sales, Forecasting, and Buyer Behavior(00:29:11) Coding Agents, Headcount Reduction, and the Future of Engineering(00:32:21) Building Defensible IP and Competing in the LLM Ecosystem(00:34:34) AI ROI, Payback Periods, and the Search for Efficiency(00:37:17) Valuations, Fund Cycles, and the Venture Market Reset(00:40:20) The Circular Flow of AI Capital and Infrastructure Overbuild(00:45:37) AI Pricing Models, Platform Wars, and Open Source Futures(00:50:02) The Race to the First $1 Trillion Private Company(00:51:09) Credits and Outro—SPONSORS:Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics#RunTheNumbersPodcast #VentureCapital #ArtificialIntelligence #StartupStrategy #FutureOfWork This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Check out Mostly Growth and get episodes early. Available on all platforms.* YouTube* Spotify* AppleConference season is back, and CJ and Kyle are swapping stories from the stage—how to nail a keynote, whether conferences are worth the money, and why your walkout song matters more than you think. From there, they dig into a new a16z report revealing where AI startups are actually spending their dollars, and CJ shares results from his summer survey showing that CFOs talk a big game about measuring AI ROI—but nobody knows how to do it. The crew also unpacks how SaaS companies like Slack are bundling AI into their products and hiking prices, before spiraling into a late-night “potentially reliable” rabbit hole featuring a Soviet pole vaulter, beat-and-raise forecasting, and J. Edgar Hoover. They close with lessons on pricing in the real world (yes, Amsterdam’s architecture is involved) and one experiment CJ tried this week.Timestamps:00:00 Preview and Intro02:03 Walkout Songs & Kicking Off Conference Season04:12 Sponsored Segment — Metronome05:16 How To Give a Great Keynote and Not Bore the Room11:16 Are Conferences Worth the Money16:02 What AI Companies Are Actually Paying For — The a16z Report21:56 Summer Survey Results: The Elusive ROI of AI23:56 Why No One Knows How To Measure ROI on AI29:38 SaaS Companies Forcing AI — Bundling, Pricing, and Pushback35:32 A Potentially Reliable Thing I Read at 2 AM36:02 Soviet Pole Vaulter, Beat-and-Raise Forecasting & Hoover’s Borders41:02 Pricing in the Real World — Lessons from Amsterdam’s Skinny Houses44:37 Something I Tried This Week — FixyerEpisodes Referenced: ⁠Are You Bad at LinkedIn… or Is the Algorithm Lying?⁠⁠Why Founders Are Posting Sad Dinners⁠Links:⁠⁠⁠https://www.getmobly.com/⁠⁠https://a16z.com/the-ai-application-spending-report-where-startup-dollars-really-go/⁠⁠https://www.growthunhinged.com/p/how-to-nail-your-next-big-talk⁠⁠https://www.leahtharin.com/p/113-vincent-pierri-how-to-deal-with⁠⁠https://www.freepik.com/⁠⁠https://cluely.com/⁠⁠https://www.mostlymetrics.com/p/it-was-the-summer-of-25⁠⁠https://www.crescendo.ai/⁠⁠https://www.linkedin.com/posts/justintropic_slack-just-raised-prices-125-by-forcing-activity-7379132597009870848-XI6N/⁠⁠https://www.mostlymetrics.com/p/what-a-soviet-era-pole-vaulter-can-teach-us-about-beating-and-raising⁠⁠https://www.nytimes.com/1972/05/03/archives/j-edgar-hoover-made-the-fbi-formidable-with-politics-publicity-and.html⁠⁠https://www.reddit.com/r/todayilearned/comments/73vh2j/til_that_the_dutch_government_once_enforced_a_tax/⁠⁠https://www.clearspaceliving.com/blog/why-dutch-stairs-are-so-steep/⁠⁠https://mjwrightnz.wordpress.com/2012/10/28/amsterdams-taxing-narrow-houses/⁠⁠https://www.fyxer.com/Today’s podcast is brought to you by MetronomeYou just launched your new AI product. The new pricing page looks great. But behind it? Last-minute glue code, messy spreadsheets, and running ad-hoc queries to figure out what to bill. Customers get invoices they can’t understand. Engineers are chasing billing bugs. Finance can’t close the books.With Metronome, you hand it all off to the real-time billing infrastructure that just works—reliable, flexible, and built to grow with you. We turn raw usage events into accurate invoices, give customers bills they actually understand, and keep every team in sync in real time.Whether you’re launching usage-based pricing, managing enterprise contracts, or rolling out new AI services, Metronome does the heavy lifting so you can focus on your product, not your billing.That’s why some of the fastest-growing companies in the world, like OpenAI and Anthropic, run their billing on Metronome.Visit metronome.com to learn more. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Private markets are swelling, public markets are shrinking, and the line between the two has never been blurrier. In this episode, CJ sits down with Scott Voss, Managing Partner at HarbourVest, to make sense of what’s happening across venture, private equity, credit, and secondaries. Scott explains why companies like SpaceX and OpenAI are now valued alongside public giants, how the surge in take-privates is reshaping corporate strategy, and what happens when the quarterly earnings pressure disappears. They dive into the rise of GP-led deals, the evolving role of private credit as the “third voice in the room,” and why liquidity—not scarcity—will define this cycle. Scott also breaks down the growing appeal of evergreen and permanent capital structures, plus what AI mega-deals signal about the next phase of private investing.—LINKS:Scott Voss on LinkedIn: https://www.linkedin.com/in/scott-voss-b91b94/HarbourVest Partners: https://www.harbourvest.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:Secondaries, Continuation Vehicles, and Sidecar Funds: Private Equity with HarbourVest’s Scott Voss -—TIMESTAMPS:(00:00:00) Preview and Intro(00:02:49) Sponsor – Mercury | RightRev | Tipalti(00:06:43) Opening Conversation(00:07:23) The Blurring Line Between Public and Private(00:09:36) The Rise of Mega Venture(00:11:20) The First $10 Trillion Company(00:12:28) The Shrinking Public Markets(00:13:09) Take-Private Playbook(00:14:04) Why Companies Go Private(00:16:00) Sponsor – Aleph | Rillet | Fidelity Private Shares(00:19:21) Efficiency and Exits(00:23:15) Liquidity in Private Markets(00:24:01) Secondaries and GP-Led Deals(00:27:14) Yale and the Secondary Market(00:29:09) Innovation and the Rise of GP-to-GP Trades(00:30:16) Liquidity Cycles and Interest Rates(00:33:18) The Third Voice in the Room – Private Credit(00:34:44) Private Credit and GP-Led Deals(00:36:02) Interest Rates and Deal Spreads(00:37:15) The Major Players in Private Credit(00:38:09) Regulation and Risk(00:39:25) Private Credit vs. Traditional Lending(00:40:33) Evergreen and Permanent Capital(00:45:57) Expanding Access to Private Markets(00:47:03) Understanding the Cap Table(00:47:44) AI Deals and Consolidation(00:50:00) The Evolution of AI and Blockchain(00:53:20) Funding Innovation and Risk(00:55:28) Lessons From Investing(00:55:39) Nostalgia and Life Phases(00:57:06) Nostalgia and the 1990s(00:59:21) Learn, Earn, and Return(01:00:45) Talking Nostalgia at Dinners(01:01:27) Summer Surfing(01:02:25) Wrap-Up and Closing—SPONSORS:Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics#RunTheNumbersPodcast #PrivateMarkets #VentureCapital #TakePrivate #FinanceLeadership This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Rama Katkar has helped steer some of the most iconic companies in tech through moments of scale and transformation. Now CFO at Notion and formerly a finance leader at Instacart and Credit Karma, she joins CJ to unpack what it means to build a modern finance function inside a product-led growth company. They discuss how to design finance for velocity without losing discipline, the art of forecasting when virality drives your business, and why Notion’s path to profitability looks different from its peers. Rama also shares lessons from scaling Credit Karma through its $8.1B acquisition by Intuit, what she learned about IPO readiness at Instacart, and how finance leaders can balance ambition with realism in uncertain markets.—LINKS:Rama Katkar on LinkedIn: https://www.linkedin.com/in/ramakatkar/Notion: https://www.notion.so/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:“Let’s Just See What Breaks” — Intuit’s CFO on Being a Disruptor When You’re Already the Incumbent— —TIMESTAMPS:(00:00) Preview – Credit Karma, Instacart, and the Road to Notion(00:01:14) Welcome & Episode Overview – Rama Katkar, CFO of Notion(00:02:22) Sponsor – Fidelity Private Shares | Mercury | RightRev(00:06:10) Interview Begins – From Dinner Conversations to Notion’s Pricing Evolution(00:09:20) Early Launch of Notion AI and Add-On Pricing(00:12:40) Community-Led Growth and Notion’s Viral Flywheel(00:14:38) Sponsor – Tipalti | Aleph | Rillet(00:18:39) Who Adopts Notion First? Product, Design, and Engineering(00:20:32) Turning Free Users Into Paid Teams(00:22:09) Why Notion Added an Enterprise Sales Motion(00:26:29) The CFO’s Long Game: Balancing Free Users and Cost(00:30:44) How Notion Experiments With AI Pricing(00:32:42) Rama’s Three-Part Framework for Forecasting(00:36:38) Why Notion Plans on a Six-Month Cadence(00:40:56) Transition – From Forecasting to M&A: Credit Karma’s Wild Ride(00:41:31) Selling Credit Karma During the Pandemic and DOJ Review(00:44:04) Closing the Deal With Intuit(00:49:47) Why the Org Chart Is the Most Important M&A Slide(00:52:08) The Long-Ass Lightning Round(00:56:45) Career Advice to Her Younger Self – Context Over Calculation—SPONSORS:Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics#CFOInsights #StartupFinance #NotionHQ #ProductLedGrowth #RunTheNumbersPodcast This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Check out Mostly Growth and get episodes early. Available on all platforms.* YouTube* Spotify* AppleAI may be rewriting the playbook for growth, but it’s also leaving behind some of the old startup gospel. CJ and Kyle (with Ben jumping in) dig into what happens when the “rules” no longer fit — from dead frameworks and disappearing SEO traffic to board members quietly checking out.Is T2D3 Dead? Did AI Kill It? The “triple-triple-double-double-double” path to $100M ARR worked in the old SaaS world. But what happens when AI companies blow past $100M in less than a year — often with questionable margins and pass-through revenue?SEO Down 20–40%: Is AEO the Savior? Google traffic is tanking. ChatGPT is rewriting recommendations. Is “AI Engine Optimization” the new growth channel, or just SEO with a different wrapper?The Brutal Tech Job Market CS grads face unemployment rates double those of art history majors. With 5,000+ applications going nowhere, does anyone get hired without networking or Loom videos anymore?Is Your Board Quiet Quitting? When growth slows and AI isn’t your story, some VCs go ghost. From missing intros to pushing for M&A, boards are quietly exiting stage left.Business Blunders* Hospital Bed LinkedIn Photos: Hustle so hard you end up in the ER (and still post about it).* The @Company Non-Tag: Execs copy-paste updates but forget to actually tag anyone. Peak passive-aggressive LinkedIn.* Ramp’s Y-Axis Crime: A 0.4% bump in weekend meals turned into a chart that looked like the apocalypse. Two burritos never looked so big.Pricing in the Real World: Bob’s Barricades It’s not Bob, it’s Happy — and he’s quietly running a barricade rental empire. Fifty cents per cone, thousands per site, tens of millions a year. The most Florida business model you’ve ever heard.Something We Tried This Week Kyle runs a test with Typeform — what worked, what didn’t, and what it says about the state of survey tools today.Today’s podcast is brought to you by MetronomeYou just launched your new AI product. The new pricing page looks great. But behind it? Last-minute glue code, messy spreadsheets, and running ad-hoc queries to figure out what to bill. Customers get invoices they can’t understand. Engineers are chasing billing bugs. Finance can’t close the books.With Metronome, you hand it all off to the real-time billing infrastructure that just works—reliable, flexible, and built to grow with you. We turn raw usage events into accurate invoices, give customers bills they actually understand, and keep every team in sync in real time.Whether you’re launching usage-based pricing, managing enterprise contracts, or rolling out new AI services, Metronome does the heavy lifting so you can focus on your product, not your billing.That’s why some of the fastest-growing companies in the world, like OpenAI and Anthropic, run their billing on Metronome.Visit metronome.com to learn more. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

The IPO market may be slowing down, but the discipline of operating like a public company has never been more important. In this episode, CJ is joined by Chad Gold, CFO of FullStory and veteran operator with previous stints at G2, SalesLoft, and Rubicon, to discuss how capital markets and financing strategies are shifting in real time. Chad explains why more companies are staying private longer, how the rise of private credit is changing the CFO toolkit, and why building IPO-ready discipline matters even if you never go public. The conversation also dives into one of his specialties—pricing models and sales incentives—covering how seat-based, usage, and blended structures influence rep behavior, comp plans, and long-term revenue quality, as well as how the wrong incentives can quietly derail a business. Finally, Chad reflects on lessons from his early career at Home Depot and how fundamentals from retail operations still inform his instincts in SaaS today.—LINKS: Chad Gold on LinkedIn: https://www.linkedin.com/in/chadgold/Fullstory: https://www.fullstory.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222 Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:G2 CFO Chad Gold on Building A Durable Career as a Venture Backed Exec:Big Systems Thinking for Building a Finance Org: Advice From a Zoom Hypergrowth Survivor:—TIMESTAMPS:(02:14) Sponsors – Mercury | RightRev | Tipalti(06:10) What’s New at FullStory(09:22) Hypotheses, Data, and Unlocking Use Cases(10:13) Early CFO Career and the Evolution of Data(11:09) From Deterministic Models to Analytics-Driven Forecasting(12:17) Cohorts, Segmentation, and Revenue Quality(13:17) Why Companies Stay Private Longer(15:28) Sponsors – Aleph | Rillet | Fidelity P.S.(19:01) Capital Flows Into Hot Sectors Like AI and Cybersecurity(20:20) More Companies Going Private Than Public(21:41) Costs and Tradeoffs of Being Public(22:46) Secondary Markets and Access to Top Companies(24:14) Staying Private Longer and CFO Planning(25:29) Keeping the Org Exit-Ready(26:10) The Rise of Private Credit(27:37) Banks vs. Venture Debt After SVB(30:47) Pricing Models Across Chad’s CFO Roles(35:47) How to Incentivize Sales Reps Across Pricing Models(43:26) Lessons From Home Depot + Lightning Round—SPONSORS:Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metricsFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.#CFOInsights #SaaSFinance #CapitalMarkets #IPOReady #RevenueStrategy #GrowthStageCFO This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Check out Mostly Growth and get episodes early. Available on all platforms.* YouTube* Spotify* AppleAI may be changing how we work, but it’s also changing how we interact with software — and not always for the better. CJ and Kyle Poyar dig into the growing pains of product design, IPOs in weird markets, and the unexpectedly depressing world of startup networking.* Navan IPO: Why a $613M company burning $80M is still pushing for an $8B valuation — and what it says about the state of software IPOs.* Prompt Bars Are Everywhere: The rise of “blank box” UX, why every app suddenly looks like ChatGPT, and how that’s giving users prompt anxiety.* Referral Programs: Ponzi Scheme?: Incentives are up, CAC is down — but is this growth channel actually sustainable or just marketing MLMs in disguise?* When to Disclose AI-Generated: If your calendar link feels cold, wait until your AI avatar shows up in an ad. We debate where the ethical (and strategic) line is for AI transparency.* Business Blunders:• Sad Dinners (CJ): Why every LinkedIn dinner photo looks depressing — and what it says about startup culture.• ChatGPT Bad Chart (Kyle): An incredible dataset ruined by a rainbow mess of tiny fonts and meaningless categories.* Potentially Reliable Thing at 2AM:• Arnold Twins Revenue (CJ): The wild deal behind Arnold Schwarzenegger’s comedy debut — and how it made more money than Terminator.• Reese Witherspoon Book Club (Kyle): Viral influence, middle-of-the-night decisions, and what media we trust half-asleep.* Pricing in the Real World:• CJ: Iced Coffee Variable Pricing: Starbucks, cold brew, and the surprising economics of how product pricing actually works day to day.* Something We Tried This Week:• Kyle: Fyxer Virtual Assistant: A hands-on experiment with offloading operational drag — what worked, what didn’t, and what Kyle’s still skeptical about.Today’s podcast is brought to you by Campfire.You may know that we use Campfire as our ERP, and it’s been a game changer for our finance workflow. The interface is intuitive, migration was quick and painless, and it’s freed us up to focus on strategic work instead of manual processes. In case you don’t know, Campfire is an AI-first ERP powering next-gen finance & accounting teams. Helps you close fast, unlock insights and scale smarter.If you’re curious about where finance tech is heading, and would like to hear more of my thoughts on the topic, don’t miss Campfire’s Finance Forward AI Summit - the upcoming summit bringing together the sharpest minds in finance and operations.You’ll hear directly from industry leaders on how they’re using AI to shape the future of finance, and how your team can get ahead of the curve. I’ll be speaking on panels with finance leaders from Anthropic, Snowflake, Mercury and more. The summit is October 28th in San Francisco; I hope to see you there.Sign up for the summit at campfiresummit.ai or learn more about Campfire at www.campfire.ai. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In the early days of a startup, forecasting isn’t about nailing the numbers, it’s about setting the course. In this episode, the world’s most interesting CFO describes the art of “Cowboy forecasting” and how this back-of-the-envelope model can be far more valuable than a complex simulation. Kevin Drost started his career as a musician and talent scout for Sony before becoming the chief strategy officer of the music gear marketplace Reverb. Now, as the CFO of New Era ADR, he explains how the company is disrupting the notoriously expensive legal industry by replacing the billable hour with flat fees, and making dispute resolution faster and more predictable for businesses. The conversation also covers why simplicity often beats complexity in financial modeling, how a hands-on understanding of the product and customer builds real financial confidence, and how finance teams can empower every employee to understand and drive the business.—LINKS:Kevin Drost on LinkedIn: https://www.linkedin.com/in/kevindrostNew Era ADR: https://www.neweraadr.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:Secrets to Scaling a Marketplace Business with Jack Greco, VC and Co-founder of ACV Auctions — —TIMESTAMPS:(00:00) Preview and Intro(02:40) Sponsor – Aleph | RightRev | Navan(07:18) Kevin’s Music Background & A&R at Sony(12:09) Record Labels Versus Venture Capital(17:01) Sponsor – Rillet | Pulley | Brex(20:53) Finding Motivation After Success(21:34) Building Reverb & the Etsy Acquisition(25:33) Stacking Skillsets & Interests(27:11) Cowboy Forecasting at Reverb(32:01) The Importance of Simplicity in Forecasting in the Early Stages(35:46) The Art and Science of Making Estimated Guesses(41:42) Building Firsthand Customer & Product Knowledge(45:36) Teaching Finance Across the Company(50:44) New Era ADR & Legal Industry Disruption(57:35) Legal Strategy Versus Financial Strategy(1:01:30) How New Era Gets Parties To Use the Platform(1:05:27) Other White Hot Use Cases for New Era ADR(1:09:25) The Long Ass Lightning Round: Kevin’s Biggest Mistake(1:12:41) Advice to a Younger Self(1:14:01) Finance Software Stack(1:15:21) Life as an A&R Rep—SPONSORS:Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalized demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what’s happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world’s smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics#CowboyForecasting #FinanceLeader #StartupFinance #LegalTech #StartupForecasting This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In a world increasingly dominated by software and automation, how vital are human relationships in banking and finance? In this episode, CJ sits down with Meghan McKenna, founder of Females in Finance (FIF) and a seasoned banker with experience at JPMorgan, HSBC, and Stifel, to explore how trusted connections continue to drive success. As a community builder and banker, Meghan has a unique perspective on the intersection of human connection and capital markets. She explains the philosophy behind her community, which is based on generosity and genuine connection rather than a transactional mindset, and how this has become her competitive advantage. The conversation also covers sales as an essential leadership skill, the rise of the modular banking stack, changes in private credit, the evolving ERP landscape, how a personal touch proved invaluable during the SVB crisis, and career lessons Meghan learned along the way.—LINKS:Meghan McKenna on LinkedIn: https://www.linkedin.com/in/meghan-curtin-mckenna-%F0%9F%94%A5-66a5022b/FIF Collective: https://www.fifcollective.comMeghan McKenna email: meghan@fifcollective.coCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:Venture Debt for Growth With Ruslan Sergeyev of Hercules Capital — The One Use Case for Venture Debt That Most Founders Never Think About — —TIMESTAMPS:(00:00) Preview and Intro(02:30) Sponsor – RightRev | Navan | Rillet(06:41) Connecting People as a Skill(08:03) Sales as an Essential Leadership Skill(12:07) The Power of In-Person Community & Events(14:39) FIF’s Ideal Customer Profile(15:42) Sponsor – Pulley | Brex | Aleph(20:05) The Evolution of the Banking Ecosystem(22:00) Modular Banking Stacks and Fintech Challengers(24:37) The Rise of Private Credit(27:32) Banks Adapting to Companies That Stay Private Longer(30:06) Fintechs vs. Traditional Banks(31:54) Current Trends in AI and ERP in Finance(35:07) Importance of Human Relationships When Software Fails(36:09) Reflecting on the SVB Bank Run & Facing New Risks in Tech(37:59) Building a Personal Brand in Finance(39:42) Community Spirit, Giving Back, & Sharing Your Network(43:25) Meghan’s Early Career and Mentors(46:15) Long-Ass Lightning Round: Staying Too Long in a Role(47:49) Advice to Younger Self(48:24) A Memorable Deal & Client Story(50:07) Wrap—SPONSORS:RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run#FemalesInFinance #FinanceLeadership #BankingInnovation #Networking #FinanceCommunity This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

AI was supposed to make software cheaper and companies more efficient. Instead, costs are exploding, CFOs are getting squeezed, and founders are pushing their teams harder than ever. CJ and Kyle Poyar dig into the economics behind AI, usage-based pricing, and what all of this means for SaaS growth.* Usage-Based Credits: Why they’re supposed to save SaaS margins but often trap customers in bad deals.* 996 Hustle Culture: The rise of 9 a.m.–9 p.m., 6-days-a-week work schedules — and why it’s both romanticized and unsustainable.* SaaS Payback Periods: Public companies now take 3+ years to recoup CAC, with growth slowing and margins tightening.* Go-to-Market Engineers: Hype vs. reality of the “unicorn hire” role meant to automate GTM motions.* Consumer Businesses: Are we sleeping on DTC plays like Blue Apron and ButcherBox while chasing AI trends?* The “Cracked Engineer” Archetype: Why the most impactful hires might be the failed founders who love solving cross-functional problems.* Subscription Carwashes: What they teach us about predictable revenue and retention psychology.* More RVs Than EVs: What this surprising stat says about adoption curves and how we misread “the future.”* This Week’s Growth Experiments: The tools, tactics, interview questions, and hacks we tried — what worked, what didn’t, and why Kyle is disillusioned by some of them.Today’s podcast is brought to you by Campfire.You may know that we use Campfire as our ERP, and it’s been a game changer for our finance workflow. The interface is intuitive, migration was quick and painless, and it's freed us up to focus on strategic work instead of manual processes. In case you don't know, Campfire is an AI-first ERP powering next-gen finance & accounting teams. Helps you close fast, unlock insights and scale smarter.If you’re curious about where finance tech is heading, and would like to hear more of my thoughts on the topic, don’t miss Campfire's Finance Forward AI Summit - the upcoming summit bringing together the sharpest minds in finance and operations.You’ll hear directly from industry leaders on how they’re using AI to shape the future of finance, and how your team can get ahead of the curve. I'll be speaking on panels with finance leaders from Anthropic, Snowflake, Mercury and more. The summit is October 28th in San Francisco; I hope to see you there.Sign up for the summit at campfiresummit.ai or learn more about Campfire at www.campfire.ai. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

The venture capital landscape is evolving, and a founder’s choice of fund size and partner could make or break their business. In this episode, CJ sits down with Kyle Harrison, General Partner at Contrary and writer of the Substack Investing 101, to make sense of the changing incentives and power dynamics in the field of venture capital. He explains how capital agglomerators and cottage keepers are playing dramatically different games, how the ethics of backing competitors have changed since the advent of AI, why a fund's size is its strategy, and what the potential pitfalls of dilution could be for founders. The conversation also covers why the line between hype and tangible business value in AI is so blurry, the role of narrative as an economic driver, and why the most valuable thing a VC can offer might just be "borrowed credibility.”—LINKS:Kyle Harrison on LinkedIn: https://www.linkedin.com/in/kyle-harrison-9274b278/Contrary: https://www.contrary.comInvesting 101: CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comLINKS MENTIONED:* “The Unholy Trinity of Venture Capital”: * “The Horse, The Jockey, or The Whole Race?” * Endowment Eddie on X (@endowment_eddie): https://x.com/endowment_eddie* “Institutionalized Belief In The Greater Fool”: * “The Unbundling of Venture Capital”: * “The Productization of Venture Capital”: https://kwharrison13.com/essays/the-productization-of-venture-capital—TIMESTAMPS:(00:00) Preview and Intro(02:23) Sponsor – Navan | Rillet | Pulley(07:13) VC Models: Cottage Keepers Versus Capital Agglomerators(11:16) Balancing Taking On Money and Finding Great Investments(16:35) Sponsor – Brex | Aleph | RightRev(20:54) Founder-Friendliness: The Ethics of Backing Competitors(26:33) When Fund Size Sabotages Outcomes(32:32) The Sins of Omission Versus Commission(36:02) The Dilution Trap for Operators in Venture-Backed Companies(38:17) Underestimating the Magnitude of the Outcomes(40:35) AI Hype, Valuation, and Real Business Impact(45:37) Market Psychology: Narrative and Story As Economic Drivers(48:21) Valuation: Cursor and Windsurf(52:50) The Unbundling of Venture Capital: What Founders Really Hire VCs For(1:01:47) Things To Consider When Choosing a VC(1:04:35) FTX Lessons & Compounding Growth(1:10:02) Kyle’s Predictions for the Future of VC—SPONSORS:Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.##VentureCapital #VC #Startups #Founder #FundSize This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Facebook is undermonetized, TikTok poses an existential threat to Amazon, and ChatGPT has probably already captured most of Google’s high-value users. These are the opinions of today's guest, a venture capitalist deeply embedded in consumer networks and social product investing. In this episode, CJ chats with Turner Novak, the Founder and Managing Partner of Banana Capital, host of The Peel podcast, and a man who is known for his Twitter threads and podcast interviews as much as he is for his impressive portfolio. Turner breaks down the monetization models of some of the world's biggest platforms. Together, they discuss undervalued and overvalued business models, the long-term viability of subscription models, how platforms can identify and serve their highest-value users, and how to adapt acquisition strategies as AI reshapes the customer journey. Turner also reveals what excites him for future investments and the underestimated power of memes as a marketing tool.—LINKS:Turner Novak on LinkedIn: https://www.linkedin.com/in/turnernovakTurner Novak on X (@TurnerNovak): https://x.com/TurnerNovakBanana Capital: https://www.bananacapital.vcThe Peel: https://www.youtube.com/@ThePeelPodthespl.it: CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: —TIMESTAMPS:(00:00) Preview and Intro(02:09) Sponsor – Rillet | Pulley | Brex(06:15) Turner’s Embarrassing Accounting Story(08:10) How Turner Became an Accidental Influencer(09:02) Monetizing Content(12:22) How Turner Built His Media Platform(16:02) Sponsor – Aleph | RightRev | Navan(20:26) From Fantasy VC Portfolios to Podcasting(24:30) Turner’s Main Business: Media Versus VC(25:42) Monetizing Premium Experiences on Social Products(30:27) Finding and Targeting High-Value Customers(32:27) Memes as a Tool for Marketing(36:10) Identifying High-Value Users and Opportunities(41:00) Why Pinterest Is Undermonetized(42:57) TikTok Versus Amazon for E-Commerce(46:30) Is ChatGPT Coming for Facebook and Google’s Cash Flow(48:36) Facebook as an Undermonetized Business(54:24) The Long-Term Viability of Subscriptions(1:00:31) Customer Acquisition in a Platform-Dominated World(1:04:09) Paid Acquisition in the Era of AI(1:06:23) The Increasing Cost of CAC(1:08:59) What Turner Is Investing in Now(1:15:25) Doing Hard Things as a Moat(1:19:12) Wrap—SPONSORS:Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.#VentureCapital #BusinessModels #GoogleVsChatGPT #ConsumerNetworks #SocialCommerce This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

It used to be that if you built a good company, showed solid growth, and had decent unit economics, you could go public. But today? The bar has been raised—big time.Let’s take a trip through the last ~15 years of tech IPOs to put today’s market into context and zoom in on the most recent companies to go public.* 2010’s: $100M is the Bar* 2021: The Year of the Mega IPOs* 2022-2023: The IPO Freeze* 2024: The Rebound – But With a Higher Bar* The New IPO PlaybookToday’s podcast is brought to you by Campfire.You may know that we use Campfire as our ERP, and it’s been a game changer for our finance workflow. The interface is intuitive, migration was quick and painless, and it's freed us up to focus on strategic work instead of manual processes. In case you don't know, Campfire is an AI-first ERP powering next-gen finance & accounting teams. Helps you close fast, unlock insights and scale smarter.If you’re curious about where finance tech is heading, and would like to hear more of my thoughts on the topic, don’t miss Campfire's Finance Forward AI Summit - the upcoming summit bringing together the sharpest minds in finance and operations.You’ll hear directly from industry leaders on how they’re using AI to shape the future of finance, and how your team can get ahead of the curve. I'll be speaking on panels with finance leaders from Anthropic, Snowflake, Mercury and more. The summit is October 28th in San Francisco; I hope to see you there.Sign up for the summit at campfiresummit.ai or learn more about Campfire at www.campfire.ai. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Is it too soon to leverage agentic automation to drive AI transformation, streamline workflows, and boost productivity in finance? And how do you calculate the ROI of AI? Today’s guest runs a high-functioning finance team at a company that's at the forefront of AI, where bonuses are tied to AI adoption. In this episode, CJ interviews Hitesh Ramani, Deputy CFO and Chief Accounting Officer at UiPath. After sharing wisdom from his years at Deloitte on the “muscle memory” that a company needs pre-IPO and mistakes to avoid after going public, he explains how his company is using its own technology to transform the finance function. He breaks down the difference between agents, robots, and workflows, describing what each does and how they interact. The conversation covers what it’s like to manage org charts that include humans and AI agents, how to hire for the future of tech-savvy finance teams, and UiPath’s vision for near-autonomous finance operations. Hitesh also reveals real-world AI use cases inside UiPath and offers lessons learned on embracing AI as a powerful productivity partner while maintaining trust and governance.—LINKS:LINKS:Hitesh Ramani on LinkedIn: https://www.linkedin.com/in/hitesh-ramani-a4a78118/UiPath: https://www.uipath.comMeghan Curtin McKenna: https://www.linkedin.com/in/meghan-curtin-mckenna-%F0%9F%94%A5-66a5022b/ FIF Collective: https://www.fifcollective.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:(00:00) Preview and Intro(02:04) Sponsor – Pulley | Brex | Aleph(06:19) Going Public Versus Being Public(09:50) The Need for a Company-Wide Operating Rhythm Pre-IPO(12:30) Top Mistakes To Avoid Before Going Public(16:01) Sponsor – RightRev | Navan | Rillet(20:06) Common Foot Faults After Going Public(23:57) Robots Versus Agents(30:17) RPA Versus AI(31:09) Agents & Workflows(34:05) Accountability: Outsourcing Your Agency(39:46) How To Measure ROI on AI(45:06) Scaling With Robots & Agents(48:15) Budgeting for People and Automation(50:41) High-Impact Versus Low-Impact Ideas in AI Implementation(53:36) Hiring & Developing Tech-Savvy Finance Talent(57:36) Build Versus Buy & Building an Autonomous Workflow(1:00:15) The Future of Autonomous Finance(1:01:14) Use Cases for AI at UiPath(1:03:18) Long-Ass Lightning Round: A Career Mistake(1:04:25) Advice to Younger Self(1:05:58) Finance Software Stack and the Future of In-House Systems(1:10:14) Craziest Expense Story—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.#AutonomousFinance #IPOJourney #AIinFinance #FutureOfFinance #AIAdoption This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

How do founders and finance leaders prepare for the sale of their company when the other side of the negotiating table does this every day? In this episode, CJ interviews David Siegel, Partner at Grellas Shah LLP, a Silicon Valley law firm that guides some of the biggest names in tech through their most significant raises and exits. David shares insights from countless deals, revealing what it really takes to prepare for a sale, negotiate with buyers, and manage conflicting advice from bankers and lawyers. He unpacks investor dynamics, deal timelines, and why the $150 million to $350 million valuation range is the “awkward middle.” The conversation also covers how companies can de-risk themselves before going to market, how to spot a bad banker, what critical pitfalls to avoid in Letters of Intent (LOIs), the emotional realities founders face when selling their “baby,” and the shifting power dynamics in today’s M&A landscape.—LINKS:David Siegel: https://www.linkedin.com/in/david-siegel-a271265Grellas Shah: https://grellas.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: —TIMESTAMPS:(00:00) Preview and Intro(02:06) Sponsor – Brex | Aleph | RightRev(06:41) The Average Time To Close M&A Deals Today(10:55) How To Start the Process of Selling a Company(13:09) Being Realistic About Your Valuation(15:13) Sponsor – Navan | Rillet | Pulley(19:08) VCs Versus Acquirers(20:12) The $150 Million to $350 Million Valuation Awkward Middle(23:17) Investor Behavior and Founder Incentives in Deals(24:59) The Banker Versus Relationship Route in Selling(27:46) What Makes a Bad Banker(28:43) PSA: Investment Banker Engagement Letters Are Negotiable(34:43) LOIs: What Sellers Should Push To Include Before Signing(39:43) What To Prioritise as a CFO in an LOI(43:21) The Worst Case Scenario for Vague Networking Capital Targets(46:22) De-Risking Your Company in the Eyes of an Acquirer(49:17) How Acquirer Risk Aversion Derails Deals(52:07) The Emotional Impact of Selling a Company(55:32) The Rules of Negotiation(57:19) Current State of M&A in Tech(1:01:30) Wrap—SPONSORS:Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.#TechAcquisitions #AcquisitionLaw #StartupExit #MergersAndAcquisitions #ExitStrategy This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Do PE Companies Trade Innovation for Margins?Private equity firms love to talk about operational excellence… but when “efficiency” comes at the cost of innovation, are they mortgaging tomorrow for today’s margins?In this episode I break down why 25% operating margins became the magic number in software, how PE-backed businesses chase the Rule of 50, and what happens when cutting R&D tips companies into the “Innovation Death Spiral.”Today’s podcast is brought to you by Campfire.You may know that we use Campfire as our ERP, and it’s been a game changer for our finance workflow. The interface is intuitive, migration was quick and painless, and it's freed us up to focus on strategic work instead of manual processes. In case you don't know, Campfire is an AI-first ERP powering next-gen finance & accounting teams. Helps you close fast, unlock insights and scale smarter.If you’re curious about where finance tech is heading, and would like to hear more of my thoughts on the topic, don’t miss Campfire's Finance Forward AI Summit - the upcoming summit bringing together the sharpest minds in finance and operations.You’ll hear directly from industry leaders on how they’re using AI to shape the future of finance, and how your team can get ahead of the curve. I'll be speaking on panels with finance leaders from Anthropic, Snowflake, Mercury and more. The summit is October 28th in San Francisco; I hope to see you there.Sign up for the summit at campfiresummit.ai or learn more about Campfire at www.campfire.ai. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

How do finance leaders enable growth while fostering a culture of partnership, positivity, and saying yes? In this episode, CJ interviews Ed Park, Head of FP&A at Facebook during its explosive hypergrowth years, Head of Finance and Internal Operations at Asana, the current CFO of Daffy, and a “glass-half-full” finance leader. Ed shares stories about working at Facebook in the early days, how he brought finance into the company’s engineering and product-first culture, and how he built trust while navigating rapid user and infrastructure expansion. He talks about his role at Asana, why the company plans in episodes, not quarters, how they discovered their unique “three user” metric, and how they transitioned from bottoms-up to sales-led growth. Ed also gives an introduction to donor-advised funds and how Daffy, his current company, is disrupting this field. The conversation covers how a company's business model shapes its destiny, finding the balance between what’s urgent and what’s important, and Ed’s glass-half-full approach to being a finance leader who enables teams by saying yes.—LINKS:Edward Park on LinkedIn: https://www.linkedin.com/in/edwardyparkDaffy: https://www.daffy.orgCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:Big Systems Thinking for Building a Finance Org: Advice From a Zoom Hypergrowth Survivor — —TIMESTAMPS:(00:00) Preview and Intro(02:16) Sponsor – Aleph | RightRev | Navan(06:43) Ed’s First Job at a Startup: Head of FP&a at Facebook(11:35) Bringing Finance Into an Engineering and Product-Led Culture(16:42) Sponsor – Rillet | Pulley | Brex(20:34) Balancing What Was Urgent Versus Important(25:02) Monetizing Facebook(26:48) Becoming a Glass-Half-Full Finance Leader(33:27) Managing Four Chefs at Asana(35:38) How Asana Plans in Episodes, Not Quarters(42:48) Monetization Model Intuition and the “Three User” Metric(48:13) Transitioning From Bottoms-Up to Proactive Sales at Asana(53:24) Daffy’s Monetization Model and Donor-Advised Fund Innovation(57:34) How a Business Model Shapes Destiny(1:00:02) Ed’s “How Might We” Approach to Being a CFO(1:01:56) Long-Ass Lightning Round: A Big Mistake(1:04:38) Advice to Younger Self(1:05:44) Finance Software Stack(1:07:57) Craziest Expense Story—SPONSORS:Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics#FacebookBusinessModel #FPandA #StartupFinance #MonetizationStrategy #DonorAdvisedFunds This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Premji Invest is an investment firm that backs some of the biggest names in the CFO and enterprise tech stack, including Anaplan, Zuora, Coupa, and Looker. In this episode, CJ is joined by Sandesh Patnam, the firm’s Managing Partner, to discuss their approach to investing and the future of CFO tech. Sandesh talks about the evergreen nature of Premji’s investment model and explains how this permanent pool of capital enables the company to focus on deep partnerships and durable growth, rather than chasing fund cycles or portfolio diversification. He breaks down why he views total addressable market (TAM) as a floor rather than a ceiling, how investing across both public and private markets creates a strategic advantage, and how startups should approach capital construction and optionality in today’s market. The conversation also touches on the evolution of the CFO toolkit, how AI is shifting the finance role, what persistent finance problems are still waiting for innovation, how org design is changing inside finance teams, and why he believes AI is a bigger shift than both the dot-com and mobile eras.—LINKS:Sandesh Patnam on LinkedIn: https://www.linkedin.com/in/sandeshpatnamPremji Invest: https://in.premjiinvest.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:BlackRock Managing Director on the Secrets of Durable Companies - —TIMESTAMPS:(00:00) Preview and Intro(02:08) Sponsor – RightRev | Navan | Rillet(06:59) Evergreen Capital and Premji’s Approach to Investing(09:25) Portfolio Construction(12:58) TAM Versus SAM Versus Product(15:28) Sponsor – Pulley | Brex | Aleph(19:51) Seats Versus Outcome-Based Pricing(23:30) Defining Durability(26:31) Public Versus Private Investing(28:44) Why One Team Manages Both Public and Private Investing(30:47) Capital Construction for CFOs With Evergreen Investors(32:13) How and When Evergreen Funds Seek Liquidity(35:32) Building Optionality in Capital Strategy Amid Market Changes(38:01) Secondary Markets in the Private World(41:39) The Evolution of the CFO Tech Stack(43:41) AI and Systems of Action(45:43) How CFOs Are Starting To Interact With AI Tech(49:09) A Finance Problem That’s Open for Innovation(50:25) The Evolution of the CFO’s Role Beyond Finance(51:33) The AI Era vs. Prior Tech Eras—SPONSORS:RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run#EvergreenCapital #PremjiInvest #CFOTechStack #InvestmentStrategy #PortfolioDurability This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com