Jake founded Serval in April 2024— by Dec 2025 he'd raised a $75M Series B from Sequoia at a $1B valuation. He didn't look for a "wedge" or a "niche." He looked at ServiceNow—a $160B, 20+ year-old incumbent that everyone IT team relies on—and rebuilt it from the ground up in a YEAR. In this episode, Jake reveals the audacity behind building a full-platform replacement from Day 1, why he spent months building in the dark with zero revenue, and how he achieved a 50% demo-to-close rate on ...

Siqi was the CEO of a hot startup doing $20M a year. Then COVID hit. Overnight, revenue went to zero. He had to lay off 95% of his staff. In the chaos of trying to save the company using broken spreadsheets, he found his next big idea: Runway. But the path wasn't a straight line. Siqi spent four years building the product before fully launching. In this episode, he breaks down why product taste matters more than A/B testing, and the insane viral launch strategy that overwhelmed his sale...

The startup game has completely changed. If you are still building with the 2018-2022 B2B SaaS playbook, you are already behind. In this episode, we break down exactly how the GenAI shift has altered value creation, competition, and business models forever. This isn’t just about adding AI to your product—it’s about rethinking your entire reason to exist. If you want to know where the massive, uncrowded opportunities are right now (and why Service-as-Software is the next gold rush)...

For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 3. Kyle left his job as a hacker at the NSA to launch Huntress. He bootstrapped for 3 years and burned all his savings. One of his co-founders quit. He got into an accelerator program, but had to sleep in his car for 16 weeks because he couldn't afford a hotel. Finally, 3 years in he'd hit $1.5M ARR. So he pitched 60 VCs for a Series A—and got 60 'no's. He was forced to raise a smal...

They were building a Segment competitor. It was working—customers were paying. But every sales call, prospects kept asking about the backend tech instead of the product. So they killed the roadmap and pivoted. It took them 18 months to hit $1M ARR. Then they started growing. And so far, they've raised $350M. Viraj walks through exactly how he validated the pivot, landed the first 10 customers, and why being outside Silicon Valley forced him to show more traction than everyone else...

For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 2. Here are the key lessons from the past 60 episodes that we've released to date. Each of the 5 steps to Product Market Fit is based on actual case studies with real examples you can use. It's a recap of everything I've learned over the last two years- you don't want to miss it. Chapters: (00:00:45) Mistakes Are Unavoidable But Avoidable Mistakes Are Unaffordable (00:04:41) ...

David had a consumer app with 50,000 users and viral traction—and he shut it down. The retention metrics weren't as good as what he'd seen at Snapchat. That difficult decision cleared the path for Juicebox, AI for recruiting that grew to $10M ARR in 2 years. In this episode, David reveals how he pivoted to AI recruiting, generated millions of views with a simple LinkedIn demo, and ground through months of brutal churn to unlock 10x growth. If you want to know how to execute a flawless P...

Jennifer went from VC to founder and immediately broke every rule in the book. When she pivoted Scribe from an automation tool to a documentation platform, her investors told her she had just killed the company. She ignored them. Instead of polishing her product, she launched a "janky" offline MVP on Product Hunt to test for real market pull. Scribe is now used by 95% of the Fortune 500. In this episode, Jennifer reveals the brutal truth about ignoring "smart" money, why you shoul...

Alex built the original Snapchat filters-- and sold his company to Snap for $166M. Then he left to start Higgsfield. The company just raised a $50M Series A to help brands create AI-generated video ads at scale. We go deep on why he thinks Adobe is in trouble, how top advertisers are already producing 10,000+ ad creatives a year, and why the companies winning in AI video aren't building foundation models. Why You Should Listen Why consumer AI apps are a trap (and what to build ins...

Eric spent 30 years in cybersecurity. Built and sold an MSSP to private equity for hundreds of millions. Then he started Tenex and hit $43 million in revenue in ONE YEAR. This isn't theory. This is a founder who's done it multiple times breaking down exactly how AI-native companies are about to eat every services industry alive. If you're building anything that touches AI, services, or enterprise sales, this is the episode. Why You Should Listen Why selling outcomes beats selling produc...

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 See...

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 co...

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...

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,...

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 eve...

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—every...

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 busine...

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...

Simon spent 10 years at Shopify scaling databases to millions of requests per second. Then he discovered vector databases were so expensive that companies couldn't launch AI features. So he solved it. When Cursor emailed about their crushing costs, Simon flew to San Francisco unannounced. They migrated their entire workload within a week, cutting their bill by 95%. Then came Notion. Justin pulled 24-hour coding marathons during their POC, fixing 300 milliseconds of latency in three hour...

Guy spent 2 years and $4M building Snyk to $100K ARR. Thousands of developers loved the product. They just wouldn't pay. Then he figured out the problem: he had product-user fit, but not product-buyer fit. Developers loved Snyk. Security teams (the actual buyers) didn't care about it. The distance between user and buyer was killing him. So Guy spent a year building governance features, reporting, and enterprise capabilities—all the stuff developers didn't care about but security teams needed ...