Anthropic’s Massive Fundraise and the AI IPO Money Machine

Anthropic’s Massive Fundraise and the AI IPO Money Machine

In this episode of Mostly Growth, the number one podcast in product monetization, Kyle and CJ break down Anthropic’s massive fundraise, its confidential IPO filing, and who actually gets paid when AI valuations go vertical. They cover crossover funds, SPVs, management fees, employee secondaries, lockups, banker fees, and why the real money may be made before the company ever trades publicly. — SPONSORS: beehiiv is a modern newsletter platform built for creators who want to grow, monetize, and own their audience without piecing together a stack. Its all-in-one platform brings together newsletters, websites, analytics, automations, and monetization tools, and now supports podcasts, webinars, and MCP workflows. Kyle even used beehiiv’s MCP in Claude to audit his site, prioritize SEO fixes, and analyze subscriber trends. Try it free at https://www.beehiiv.com/kyle [https://www.beehiiv.com/kyle] and use code KYLE30 for 30% off your first three months. Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run [https://www.tabs.com/run] Lightfield is an AI-first CRM built for modern sales teams that want to manage deals without manual data entry or dashboards. By joining sales calls, reading emails, and maintaining full account context, Lightfield helps teams prioritize deals, automate follow-ups, and stay prepared for every interaction. It’s like having a sales coach, RevOps analyst, and EA in one. Start a 14-day free trial at https://www.lightfield.app [https://www.lightfield.app] and use code MOSTLYGROWTH to get 3 months free. — LINKS:  Mostly Metrics: https://www.mostlymetrics.com [https://www.mostlymetrics.com] CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ [https://www.linkedin.com/in/cj-gustafson-13140948/] Growth Unhinged: https://www.growthunhinged.com/ [https://www.growthunhinged.com/] Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/ [https://www.linkedin.com/in/kyle-poyar/] Slacker Stuff: https://www.slackerstuff.com/ [https://www.slackerstuff.com/] Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/ [https://www.linkedin.com/in/slackerstuff/] — RELATED EPISODES: SpaceX S1 Breakdown: The Numbers Behind the Biggest IPO in History https://youtu.be/AARjbTO8FKo [https://youtu.be/AARjbTO8FKo] Anthropic Is Catching OpenAI Faster Than Anyone Expected https://youtu.be/HqzjybVek4M [https://youtu.be/HqzjybVek4M] Should You Stay or Leave Your Job? https://youtu.be/2-HBLBHwWfA [https://youtu.be/2-HBLBHwWfA] — TIMESTAMPS: 0:00 Germany's golf license 3:45 Why the raise and IPO filing happened together 6:08 Who led the round: crossover funds 10:11 Sponsors — beehiiv | Tabs | Lightfield 13:12 SPVs explained 15:06 SPV fee structures 18:02 AI IPOs as a management fee machine 20:06 Seed VC vs. late stage 21:04 Carry vesting: golden handcuffs 24:45 Have Anthropic employees made money? 25:32 OpenAI secondary: 75 people hit $30M 25:40 Anthropic's secondary at $350B 27:03 What "confidential filing" actually means 29:53 Banker fees: 3–5% of the float 31:00 Employee, investor, or banker? 33:00 Could anyone acquire Anthropic? 33:25 Fun fact: Germany's church tax 34:12 Credits #MostlyGrowthPodcast #IPO #VentureCapital #AIStrategy #Investing

The 5 Ways to Build a $100M ARR Business

In this episode of Mostly Growth, the number one podcast in product monetization, CJ and Kyle break down the five paths to building a $100M ARR business — from mice to elephants — and what new data from 1,043 startups reveals about which paths founders actually choose, why most companies stay with their first customer segment, and why deer hunters may be growing 3–5x faster. — SPONSORS: Lightfield is an AI-first CRM built for modern sales teams that want to manage deals without manual data entry or dashboards. By joining sales calls, reading emails, and maintaining full account context, Lightfield helps teams prioritize deals, automate follow-ups, and stay prepared for every interaction. It’s like having a sales coach, RevOps analyst, and EA in one. Start a 14-day free trial at https://www.lightfield.app [https://www.lightfield.app] and use code MOSTLYGROWTH to get 3 months free. beehiiv is a modern newsletter platform built for creators who want to grow, monetize, and own their audience without piecing together a stack. Its all-in-one platform brings together newsletters, websites, analytics, automations, and monetization tools, and now supports podcasts, webinars, and MCP workflows. Kyle even used beehiiv’s MCP in Claude to audit his site, prioritize SEO fixes, and analyze subscriber trends. Try it free at https://www.beehiiv.com/kyle [https://www.beehiiv.com/kyle] and use code KYLE30 for 30% off your first three months. Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run [https://www.tabs.com/run] — LINKS:  Mostly Metrics: https://www.mostlymetrics.com [https://www.mostlymetrics.com] CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ [https://www.linkedin.com/in/cj-gustafson-13140948/] Growth Unhinged: https://www.growthunhinged.com/ [https://www.growthunhinged.com/] Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/ [https://www.linkedin.com/in/kyle-poyar/] Slacker Stuff: https://www.slackerstuff.com/ [https://www.slackerstuff.com/] Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/ [https://www.linkedin.com/in/slackerstuff/] — RELATED EPISODES: SaaS Has a Branding Problem https://youtu.be/qWyjFTqnfhg [https://youtu.be/qWyjFTqnfhg] — TIMESTAMPS: 0:00 Swag, merch stores, and VC baby bibs 5:13 Topic intro: 5 ways to build a $100M business 7:43 The framework: flies, mice, rabbits, deer, elephants 8:51 Mouse hunting: $100/year, need a million customers 9:07 Rabbit hunting: the most common starting point 9:57 Deer hunting: where sales investment starts to make sense 10:09 Sponsors — Lightfield | beehiiv | Tabs 13:09 Company examples for each animal 15:46 The data: 1,043 companies from Chartmogul 17:16 Retention by animal: the leaky bucket problem 20:36 Starting animal doesn't affect early growth — but does later 21:12 Retention rates: mice 25%, deer 70%, elephants 100% 23:27 Retention imprints on your DNA — even 3 years later 24:25 The sweet spot: deer is the best starting point 26:31 Why elephant hunting early usually fails 28:10 70% of companies never change target customer 29:03 Most common migration: rabbit to deer 30:35 HubSpot: the rabbit-to-deer poster child 31:28 Takeaway: you are what you hunt 31:33 Business blunders: AI-generated LinkedIn comments 33:34 Credits #MostlyGrowthPodcast #SaaS #ProductGrowth #StartupGrowth #RevenueOperations

Who's Actually Hiring in GTM Right Now?

In this episode of Mostly Growth, the number one podcast in product monetization, Kyle digs into who's actually hiring in GTM right now — and the data is full of surprises. SDR jobs are supposedly dying, yet AI-native startups are doubling down on them. GTM engineering is the breakout role. Customer support is being automated away. The full picture from 120K+ job posts. — SPONSORS: Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run [https://www.tabs.com/run] Lightfield is an AI-first CRM built for modern sales teams that want to manage deals without manual data entry or dashboards. By joining sales calls, reading emails, and maintaining full account context, Lightfield helps teams prioritize deals, automate follow-ups, and stay prepared for every interaction. It’s like having a sales coach, RevOps analyst, and EA in one. Start a 14-day free trial at https://www.lightfield.app [https://www.lightfield.app] and use code MOSTLYGROWTH to get 3 months free. beehiiv is a modern newsletter platform built for creators who want to grow, monetize, and own their audience without piecing together a stack. Its all-in-one platform brings together newsletters, websites, analytics, automations, and monetization tools, and now supports podcasts, webinars, and MCP workflows. Kyle even used beehiiv’s MCP in Claude to audit his site, prioritize SEO fixes, and analyze subscriber trends. Try it free at https://www.beehiiv.com/kyle [https://www.beehiiv.com/kyle] and use code KYLE30 for 30% off your first three months. — LINKS:  Mostly Metrics: https://www.mostlymetrics.com [https://www.mostlymetrics.com] CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ [https://www.linkedin.com/in/cj-gustafson-13140948/] Growth Unhinged: https://www.growthunhinged.com/ [https://www.growthunhinged.com/] Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/ [https://www.linkedin.com/in/kyle-poyar/] Slacker Stuff: https://www.slackerstuff.com/ [https://www.slackerstuff.com/] Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/ [https://www.linkedin.com/in/slackerstuff/] — RELATED EPISODES: Should You Stay or Leave Your Job? https://youtu.be/2-HBLBHwWfA [https://youtu.be/2-HBLBHwWfA] When the marketing math doesn’t math | with Emily Kramer https://youtu.be/sSuoV_YSrlw [https://youtu.be/sSuoV_YSrlw] Fantasy Startup Draft: The First 5 Hires We’d Make Today https://youtu.be/usxbRdABi0I [https://youtu.be/usxbRdABi0I] — TIMESTAMPS: 0:00 Coyote encounter 2:04 Show intro 2:28 Who's hiring in GTM? 4:44 SDR posts down 21% — but AI companies are hiring the most 7:30 AI native companies only 5% of GTM hiring 7:58 Jevons paradox and SDR efficiency 9:29 Why AI companies need more SDRs, not fewer 10:33 Sponsors — Tabs | Lightfield | beehiiv 13:34 Customer support down 67% at AI native companies 15:07 Customer success is holding steady 16:04 Solutions engineering: still in demand 17:39 GTM hiring overall down 15% YoY 18:21 Sales: still 40% of GTM, holding up 19:57 Marketing down 20% — but growth marketing up 8% 21:22 Fastest growing role: GTM engineer 22:13 RevOps is flat — and that's actually good 23:16 GTM ratios: 10 salespeople to 4 SEs, 4 marketers 24:06 Are GTM roles becoming more generalist? 27:04 Career advice: develop AI skills 28:44 Biggest surprise: RevOps not getting crushed 29:35 Biggest takeaway: marketers are leading AI adoption 31:44 Hull parking permit misspelling 33:03 RevSwap AI: revenue laundering platform 33:59 General Catalyst ad backfires 34:39 Credits #MostlyGrowthPodcast #SaaS #GrowthMarketing #RevenueOperations #AIStrategy

The Great Career Reshuffling: Should I Stay, Or Should I Go?

In this episode of Mostly Growth, the number one podcast in product monetization, CJ and Kyle unpack the career anxiety spreading across tech. They talk about AI, private-company wealth, career leverage, title vs. cash vs. equity, and why the smartest move may be getting brutally clear on the game you’re actually playing. — SPONSORS: beehiiv is a modern newsletter platform built for creators who want to grow, monetize, and own their audience without piecing together a stack. Its all-in-one platform brings together newsletters, websites, analytics, automations, and monetization tools, and now supports podcasts, webinars, and MCP workflows. Kyle even used beehiiv’s MCP in Claude to audit his site, prioritize SEO fixes, and analyze subscriber trends. Try it free at https://www.beehiiv.com/kyle [https://www.beehiiv.com/kyle] and use code KYLE30 for 30% off your first three months. Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run [https://www.tabs.com/run] Lightfield is an AI-first CRM built for modern sales teams that want to manage deals without manual data entry or dashboards. By joining sales calls, reading emails, and maintaining full account context, Lightfield helps teams prioritize deals, automate follow-ups, and stay prepared for every interaction. It’s like having a sales coach, RevOps analyst, and EA in one. Start a 14-day free trial at https://www.lightfield.app [https://www.lightfield.app] and use code MOSTLYGROWTH to get 3 months free. — LINKS:  Mostly Metrics: https://www.mostlymetrics.com [https://www.mostlymetrics.com] CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ [https://www.linkedin.com/in/cj-gustafson-13140948/] Growth Unhinged: https://www.growthunhinged.com/ [https://www.growthunhinged.com/] Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/ [https://www.linkedin.com/in/kyle-poyar/] Slacker Stuff: https://www.slackerstuff.com/ [https://www.slackerstuff.com/] Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/ [https://www.linkedin.com/in/slackerstuff/] — RELATED EPISODES: A CFO Explains Secondaries https://youtu.be/pENvBuXhGuk [https://youtu.be/pENvBuXhGuk] Sam Jacobs of Pavilion https://youtu.be/8X-JVOF-1A0 [https://youtu.be/8X-JVOF-1A0] Bruno Annicq of Wellhub https://youtu.be/dfjSjPAXEEk [https://youtu.be/dfjSjPAXEEk] — TIMESTAMPS: 0:00 SF trip and CFO dinners 1:27 A consistent feeling: am I on the right thing? 2:47 Anthropic secondary: 75 people hit $30M cap 3:06 Anecdote 1: CFO at 50M ARR SaaS 7:58 Anecdote 2: banker pivoting to defense tech 8:03 Cybersecurity: best and worst of times 10:40 Sponsors — beehiiv | Tabs | Lightfield 13:40 Graduation speaker gets booed for AI speech 15:10 The comparison trap: luck vs. merit in SaaS 17:54 What are you maximizing for? 18:29 Is leaving tech a real path? 21:07 Advice for the great reshuffling 21:51 Lever 1: maximize equity 22:51 Lever 2: maximize base cash 23:30 Lever 3: maximize title and opportunity 24:00 Lever 4: lifestyle and autonomy 24:52 CJ's career story: consulting at 58k 28:28 OpenView: pay cut for long-term growth 29:13 Is there career arbitrage right now? 29:48 Why join a fast-growing AI company 31:06 Hot AI startups pay well — but expectations are high 32:04 18 months to get in the club 33:26 How to pick the right AI company 34:19 Can you have a great job at a bad company? 35:03 Mediocre at a great company beats the reverse 36:18 Career at a twilight company? 38:38 If you had to choose: what do you join? 38:49 Best time ever to be a small business owner 39:45 AI at the pizza shop story 41:18 Credits #MostlyGrowthPodcast #CareerGrowth #SaaS #AIStrategy #StartupGrowth

SpaceX, Starlink, and the Era of Capital-Intensive IPOs

In this episode of Mostly Growth, the number one podcast in product monetization, CJ and Kyle break down SpaceX’s potential $1.5T IPO, Starlink’s subscription engine, xAI’s cash burn, and why the next wave of mega-IPOs could pull hundreds of billions out of the market. The question isn’t just whether SpaceX is worth it. It’s who has to fund the bet. — SPONSORS: Lightfield is an AI-first CRM built for modern sales teams that want to manage deals without manual data entry or dashboards. By joining sales calls, reading emails, and maintaining full account context, Lightfield helps teams prioritize deals, automate follow-ups, and stay prepared for every interaction. It’s like having a sales coach, RevOps analyst, and EA in one. Start a 14-day free trial at https://www.lightfield.app [https://www.lightfield.app] and use code MOSTLYGROWTH to get 3 months free. beehiiv is a modern newsletter platform built for creators who want to grow, monetize, and own their audience without piecing together a stack. Its all-in-one platform brings together newsletters, websites, analytics, automations, and monetization tools, and now supports podcasts, webinars, and MCP workflows. Kyle even used beehiiv’s MCP in Claude to audit his site, prioritize SEO fixes, and analyze subscriber trends. Try it free at https://www.beehiiv.com/kyle [https://www.beehiiv.com/kyle] and use code KYLE30 for 30% off your first three months. Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run [https://www.tabs.com/run] — LINKS:  Mostly Metrics: https://www.mostlymetrics.com [https://www.mostlymetrics.com] CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/ [https://www.linkedin.com/in/cj-gustafson-13140948/] Growth Unhinged: https://www.growthunhinged.com/ [https://www.growthunhinged.com/] Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/ [https://www.linkedin.com/in/kyle-poyar/] Slacker Stuff: https://www.slackerstuff.com/ [https://www.slackerstuff.com/] Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/ [https://www.linkedin.com/in/slackerstuff/] — TIMESTAMPS 0:00 SpaceX IPO at $2T? 0:57 Topic framing: the everything's-confidential S1 3:18 What SpaceX is: rockets, Starlink, xAI, X 6:42 Launch services: $4B, reusable rockets 7:03 Rideshare pricing: $350K, transparent pricing 8:26 Launch is a loss leader for Starlink 8:30 Starlink: $10B and 63% EBITDA margins 10:20 Sponsors — Lightfield | beehiiv | Tabs 13:20 Starlink plans: residential vs. roam 15:45 10M subscribers, path to 20M 16:26 X/Twitter and xAI: $5B, burning $1B/month 18:40 Data centers in space: the AI thesis 20:05 IPO process and Morgan Stanley 20:51 $1.75T valuation: Comcast in space 21:14 Will SpaceX buy Tesla? 22:26 Bundling vs. unbundling: why it works here 25:05 Forward multiple: 50–70x 27:35 S&P 500 inclusion boost 28:32 30% retail allocation: meme stock? 30:22 Credits #MostlyGrowthPodcast #IPO #SpaceX #GrowthStrategy #Investing