A Product Market Fit Show | Startup Podcast for Founders

Q3 2025 w/Carta: What you need to raise a Series A. | Peter Walker, Head of Insights at Carta

Carta's Peter Walker is back with the freshest data on what's actually happening at the early stage—and it's not what you're reading on X. While headlines scream about record-breaking rounds, the reality on the ground tells a different story.  Seed deals are down. Time between rounds is stretching. And there's a brutal divide between the companies getting all the attention and everyone else.  We dig into the exact valuations, graduation rates, team sizes and revenue you need for Seed and Series A... plus why the lowest-quartile seed rounds are failing at twice the rate. If you're raising or planning to raise, this is the episode. Why You Should Listen * The round size that cuts your Series A odds in half * Why smaller teams are winning (and what that means for your hiring plan) * The real median valuations at pre-seed, seed, and Series A right now * How long it actually takes to get from seed to Series A in 2024 * When taking secondary as a founder makes sense (and when it doesn't) Keywords startup podcast, startup podcast for founders, seed round valuation, Series A fundraising, startup fundraising data, venture capital trends, pre-seed funding, startup metrics, founder secondary, seed to Series A Chapters: 00:00:00 Intro  00:02:46 Seed Valuations and Who Actually Graduates to Series A  00:06:58 What Founders Outside the Hot Cohort Should Do  00:11:44 Team Sizes Are Shrinking and Employees Are Getting Less  00:17:40 Crowded Categories and Competing with Foundation Models  00:24:47 Founders Starting Companies for the Wrong Reasons  00:33:32 When Founder Secondaries Make Sense  00:39:55 The Actual Median Valuations at Pre-Seed Seed and Series A Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

He added AI to parking lots—then raised $3.5B. | Alex Israel, Founder of Metropolis

Alex and his co-founders spent 2018 pitching parking lot owners on computer vision tech. Every meeting ended the same way: "Cute startup, come back in 30 years."  So they did something else—they bought the parking operators and implemented the AI themselves. VCs called them delusional. But today, Metropolis has 20 million members and adds 1 million new members every month. Every 1-2 seconds someone signs up. Alex's biggest lesson? When enterprise customers won't adopt your tech, don't convince them—buy them. Sometimes the only way to disrupt an industry is to become the industry.  Why You Should Listen: * The "growth buyout" playbook—buy old companies to force your tech  * Why adding friction made their product better  * The counter-intuitive metric: success = less time users spend in your product * Why VCs said "absolutely not" to their best strategic move Keywords: startup podcast, startup podcast for founders, Metropolis, Alex Israel, computer vision, growth buyout, parking technology, M&A strategy, enterprise sales, B2B SaaS 00:00:00 Intro 00:03:05 Seeing the parking opportunity 00:06:37 The original vision 00:12:33 Raising $7.5M and leasing the first two parking lots 00:16:04 First customer transaction 00:22:58 The growth buyout strategy 00:27:54 Acquiring SP Plus with 23,000 employees 00:34:32 Building beyond parking Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

He left a $2B ARR company to build AI agents—then hit $1M ARR in < 6 months | Amit Shah, Founder of Instalily

Amit walked away from being President of 1-800-Flowers after scaling it from $500M to $2B because he saw smart people trapped in dumb systems. His insight: half of global GDP is 90% manual work—salespeople entering data instead of selling, technicians reading manuals instead of fixing.  He started Instalily in Spring 2023 when everyone said AI agents were impossible. Instead of replacing workers, he built AI that finds signals in noise—telling each salesperson exactly which deal to focus on right now. The results are insane: $1M ARR within months, tripling revenue year two, delivering $150M+ value to single customers.  His secret? While competitors pitched flashy demos, Amit's team attended 100+ trade shows to understand actual operator pain. They hired fresh AI grads who "shipped fearlessly" instead of senior talent stuck in old paradigms. Why You Should Listen: * How "operator market fit" beats product market fit for enterprise sales * The GTM playbook that hit $1M ARR in months by attending 100+ trade shows * Why hiring AI-native grads crushed hiring senior talent for AI products * How focusing on time-to-value unlocked enterprise deals * The counterintuitive approach: augment the best parts of jobs, not the worst Keywords: startup podcast, startup podcast for founders, Instalily, Amit Shah, AI agents, enterprise sales, operator market fit, B2B SaaS, AI automation, vertical SaaS 00:00:00 Intro 00:04:42 Leaving 1-800-Flowers 00:09:55 Starting when everyone said AI agents were impossible 00:11:51 The vision—amplify the best parts of work, not replace the worst 00:16:59 Operator market fit over product market fit 00:20:48 Landing first $2B enterprise customers  00:29:00 The 100+ trade show GTM strategy that actually worked 00:33:02 Why they hired AI-native grads instead of senior talent 00:34:51 Hitting $1M ARR in months Retry Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

He tested his idea in one weekend—then raised $120M. | Wayne Slavin, Founder of Sure

Wayne tested flight insurance over a single weekend with a WordPress site and Google ads. When people tried to pay, he showed a fake error message. The result: 15.9% conversion. That validation led to Sure, now powering insurance for Tesla, Toyota, and MasterCard.  But the journey was brutal. Wayne worked solo for a year, burning through savings in San Francisco. Flew to South Africa for 7 weeks to land his first insurance partner.  The real breakthrough came 4 years later, in 2019, when Elon tweeted about Tesla insurance—instant rocket ship growth. Today Sure is the rails for embedded insurance, like Visa for credit cards. They raised $120M but haven't needed money since 2021 because they've been profitable since their Series B.  Why You Should Listen: * How to validate an entire business in a weekend.  * Why he worked solo for a year before raising money or hiring anyone. * The exact playbook for pivoting while keeping your old product alive. * How one Elon Musk tweet created instant product-market fit. Keywords: startup podcast, startup podcast for founders, Sure, Wayne Slavin, embedded insurance, InsurTech, product validation, bootstrap to profitable, Tesla insurance, B2B pivot 00:00:00 Intro 00:01:48 The flight to Vegas that sparked a $120M insurance company 00:03:03 Building a fake insurance product in one weekend to test demand 00:11:00 Working solo for a year while burning through savings 00:14:43 Flying to South Africa for 7 weeks to land first insurance partner 00:19:58 Convincing 5 friends to quit their jobs 00:27:56 Pivoting from mobile app to embedded insurance 00:46:03 Elon's tweet creates rocket ship growth overnight Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

At 21 he made his 1st million. At 23, he grew his startup to $8M ARR in 6 months. | Matt Espinoza, Founder of Clover

Matt sold his first company at 19 and made $100K. He sold his second at 21 and made $800K. A couple years later, he launched Clover and grew it to $8M ARR in 6 months.  His secret? Insane distribution. His formula is to ignore quality—and engineer quantity instead. While everyone obsesses over viral content, Matt posts 1,000 videos across 333 accounts daily, guaranteeing a million views through pure math. No luck required.  He applies the same "volume negates luck" philosophy to everything: 15,000 cold emails daily, thousands of Reddit posts to dominate SEO rankings.   Matt reveals the exact Reddit hack to guarantee #1 Google rankings, how AI agents automate everything from account creation to content generation, and why he purposely changes video metadata to trick algorithms at scale. At 23, he's cracked distribution so thoroughly that he can now incubate any business and guarantee its growth. Why You Should Listen: * How posting 1,000 videos daily GUARANTEES 1M views  * The Reddit hack that guarantees #1 Google rankings in 7 days * Why referral revenue is the only true sign of product-market fit * The "volume negates luck" framework that beats any growth strategy Keywords: startup podcast, startup podcast for founders, Matt Everett, Clover, growth hacking, viral marketing, SEO hacking, distribution strategy, AI automation, bootstrapping Chapters: 00:00:00 Intro 00:01:31 Selling first company at 20 00:03:54 Selling second company for $800K in 3 months 00:06:37 The 1000 videos per day distribution hack 00:24:39 How to guarantee #1 on Google with Reddit posts 00:30:52 15,000 cold emails daily—the outbound machine 00:47:27 Why 30% referral revenue is true product-market fit Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]