A Product Market Fit Show | Startup Podcast for Founders

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]

He walked away from $5M ARR—then built a $50M company. | Russ Fradin, Founder of Larridin

Russ has started and sold multiple companies over 30 years, but his Dynamic Signal journey will change how you think about product-market fit. They had $5M ARR selling influencer marketing software.  Then Russ told investors to pretend the $5M didn't exist and bet on a $200K pipeline instead. That pivot led to 600 Fortune 2000 customers and an exit at $50M ARR.  Now building his AI measurement startup Larridin, Russ shares why being a repeat founder creates a different problem—everyone tells you your idea is great even when it's not. His solution? Don't believe anything until someone writes a check. Why You Should Listen: * Why he walked away from $5M ARR to pursue a $200K pipeline. * How emergent user behavior revealed a $50M business. * Why "everyone loving your idea" means nothing. * Why finding product-market fit is only step 1. Keywords: startup podcast, startup podcast for founders, Dynamic Signal, Russ Glass, product-market fit, enterprise sales, employee advocacy, pivot strategy, B2B SaaS, influencer marketing 00:00:00 Intro 00:01:36 30 years of Silicon Valley startups 00:03:05 Dynamic Signal's original idea 00:07:29 The emergent behavior that changed everything 00:15:38 Walking away from $5M ARR to pursue a $200K opportunity 00:18:23 Why product-market fit is never final 00:22:14 Selling Dynamic Signal  00:24:30 Starting Laridin 00:36:34 Raising $17M as a repeat founder—why everyone says yes Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

He made 2 key changes —then grew to $100M ARR in 2 years & exited for $2B. | Harish Abbott, Founder of Deliverr & Augment

Harish spent 9 months building Deliver and could barely get 10 customers. The product worked. Merchants liked the fast delivery promise. But nobody was signing up. Then he made two changes—and scaled to $100M in revenue in 2 years. Shopify acquired them for over $2B. Harish says it wasn't about finding product-market fit. It was about finding product-PRICE-market fit. The product was fine. The pricing model was killing them.  This episode breaks down why pricing often isn't just a business decision—it's part of your product, how to build self-serve systems that scale to thousands of customers without talking to anyone, and why you must obsess about end users AND economic buyers if you actually want adoption. Harish is now building Augment, an AI company for logistics that just raised an $85M Series A. He shares what he learned shadow-sitting operators for 60 days and why demos mean nothing in the AI era. Why You Should Listen: * Why PMF is often not enough—you need  product-price-market fit * Why subtle changes can have huge results * Why you need both users AND buyers to love your product * How to master self-serve  Keywords: startup podcast, startup podcast for founders, product market fit, pricing strategy, $2B exit, Shopify acquisition, product-price fit, logistics startup, self-serve systems, Amazon fulfillment 00:00:00 Intro 00:07:06 Starting Deliver in 2017 00:14:24 Struggling with only 10 customers after 9 months 00:19:53 The two changes that changed everything 00:23:43 Zero to $100M in 2 years and product-price-market fit 00:29:32 How the $2B+ Shopify acquisition happened 00:32:07 Starting Augment AI for logistics 00:47:35 PMF moments and top advice  Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]

He built a $20B public company, left—then raised a $100M Series A. | Dheeraj Pandey, Founder of Nutanix & DevRev

Dheeraj built Nutanix into a $20B public company—then walked away to start DevRev. He just raised a $100M Series A. This episode breaks down why most founders "sell and run" (chase new logos instead of delivering value), why that strategy fails, and how Dheeraj thinks about building platforms with use cases instead of just features. He explains why the biggest opportunities come from bundling and why you need to hit 130%+ NRR to scale in B2B. Dheeraj also shares the two near-death experiences at Nutanix in the first 5 years, how they survived, and what he's building differently at DevRev in the AI-native world. If you're wondering whether you have real PMF, how to think about platforms vs features, or why your existing customers matter more than new ones—this is mandatory listening from someone who's done it twice at massive scale. Why You Should Listen: * Learn why PMF at $1M doesn't mean PMF at $10M—and why you have to find it again at every milestone * Why "sell and run" kills startups—the real work starts after you close the deal * See how platform thinking (not feature thinking) took Nutanix to $1B ARR * Understand why 30-40% of revenue from existing customers is real PMF  Keywords: startup podcast, startup podcast for founders, product market fit, platform thinking, Nutanix founder, enterprise SaaS, net dollar retention, PMF milestones, fastest to $1B, second-time founder 00:00:00 Intro 00:01:58 Starting Nutanix 00:14:24 Why he left a $20B company 00:18:53 The DevRev thesis 00:27:39 Pre-AI vs post-AI product strategy and the agent shift 00:40:57 Platform vs features 00:46:25 PMF is not a destination 00:48:10 #1 Advice Send me a message to let me know what you think! [https://www.buzzsprout.com/twilio/text_messages/1889238/open_sms]