Run the Numbers

• Circular Finance, $1T Dreams, and the AI War for Talent with Joe Floyd of Emergence Capital

  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

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• How to Crush Your Keynote (Even If You’re Dying Inside)

  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

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• From Take-Privates to AI: Mapping the New Market Cycle with Scott Voss

  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

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• From Credit Karma to Notion: CFO Rama Katkar on Leading Finance Through Every Growth Stage

  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

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• SEO’s Collapse, Job Hunt Grind & Cone King Bob

  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

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