A Product Market Fit Show | Startup Podcast for Founders

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Every founder has 1 goal: find product-market fit. We interview the world's most successful startup founders on the 0 to 1 part of their journeys. We've had the founders of Reddit, Gusto, Rappi, Glean, Cohere, Huntress, ID.me and many more. We go deep with entrepreneurs & VCs to provide detailed examples you can steal.  Our goal is to understand product-market fit better than anyone on the planet. Rated one of the world's top startup podcasts.

  1. This 3x founder hit $1M ARR in 5 months. Here's his playbook. | Roy Moussa, Founder of GetVocal

    2H AGO

    This 3x founder hit $1M ARR in 5 months. Here's his playbook. | Roy Moussa, Founder of GetVocal

    Roy is a three-time founder who has cracked the code on enterprise AI. After selling his first company and realizing his second idea was too slow, he pivoted to solving a massive problem: customer service automation. In this episode, Roy breaks down how GetVocal went from zero to $1M ARR in just five months. He reveals the "Context Graph" technology that allows them to beat LLM wrappers, why he believes purely generative AI is useless for business, and how he turned a single deployment into an enterprise-wide contagion. Why You Should Listen How to hit $1M ARR in 5 months with a single salesperson.Why "Context Graphs" are the secret to building AI that doesn't hallucinate.How to expand from a single agent to 80 agents across the enterprise.The critical difference between Deterministic and Probabilistic AI Why starting with a personal passion project failed, but pivoting to enterprise worked.Keywords startup podcast, startup podcast for founders, product market fit, enterprise AI, customer service automation, finding pmf, context graphs, AI agents, B2B sales, Roy Moussa 00:00:00 Intro 00:02:29 From Engineer to 3-Time Founder 00:08:11 The Failed Pivot 00:12:49 Solving Sales Efficiency First 00:16:06 The Pivot to Customer Service 00:18:57 Why Chatbots Failed & The Hybrid AI Solution 00:25:43 What is a Context Graph? 00:34:46 The "Contagion" Effect: 80 Agents in 8 Weeks 00:39:34 Competing with Decagon & The Human-Centric Approach 00:41:58 Hitting $1M ARR in 5 Months Send me a message to let me know what you think!

    44 min
  2. He made 0 sales for the first 8 months. Now he does $200M+ ARR. | Ryan Anderson, Founder of Filevine

    3D AGO

    He made 0 sales for the first 8 months. Now he does $200M+ ARR. | Ryan Anderson, Founder of Filevine

    Ryan was a successful lawyer with a massive problem. He couldn't find a task management tool that worked for his firm, so he built one himself. He thought he'd solved the problem, but for 8 agonizing months, he couldn't sell a single subscription. In this episode, Ryan breaks down the gritty reality of bootstrapping Filevine into a $3B legal tech startup doing over $200M in revenue. He shares how a random Instagram ad campaign ended his sales drought, how he fought off a Tiger Global-backed competitor built on Salesforce, and how he's completely rewriting his company's architecture to win the AI legal tech war against the likes of Harvey and Legora. Why You Should Listen How 8 months of zero sales almost broke him.Why building customizability into your core product is the ultimate defense.How to recruit top engineers when you have zero funding.Why SMBs often have "beer money but champagne tastes."How to pivot from SaaS to AI.Keywords startup podcast, startup podcast for founders, legaltech, product market fit, bootstrapping, B2B SaaS, enterprise sales, AI startup, founder story, finding pmf 00:00:00 Intro 00:07:20 Recruiting an Amazon Engineer with No Funding 00:11:52 The First Conference and the "Terrible" MVP 00:15:23 The Dark Months: Zero Sales from Cold Calling 00:19:28 The GTM that Saved the Company 00:27:36 Why In-Person Events Beat Cold Calling 00:36:19 Moving Upmarket to Avoid Demanding SMBs 00:37:32 Beating a $50M Salesforce-Backed Competitor 00:46:45 Rewriting Filevine for the AI Era Send me a message to let me know what you think!

    57 min
  3. He built heads down for a year. Then landed a $1M contract. | Sam Jones, Co-Founder of Method Security

    MAR 5

    He built heads down for a year. Then landed a $1M contract. | Sam Jones, Co-Founder of Method Security

    Sam spent years at the Air Force and Palantir before deciding to build Method Security. Instead of launching an MVP and iterating with customers, he did the opposite: he shut out the world and built in the dark for a year based on his own conviction. In this episode, Sam breaks down his contrarian approach to building a platform for the enterprise and government. He reveals how he raised millions from Andreessen Horowitz with just a prototype, why he refuses to hire a sales team, and how he landed a seven-figure contract right out of the gate. Why You Should Listen Why he ignored the "talk to users" advice and built in the dark for a year.How to raise a $5.5M seed round from a16z in just 3 days.The "2-Hour Bootcamp" strategy that shortens enterprise sales cycles.Why keeping your engineering team dangerously small creates speed.How to turn a design partnership into a $1M+ contract.Keywords startup podcast, startup podcast for founders, product market fit, cybersecurity, a16z, Palantir, enterprise sales, design partners, government contracting, founder led sales 00:00:00 Intro 00:02:00 From Air Force to Palantir 00:06:28 The "Shared Notion Space" of Ideas 00:10:04 Raising Seed from a16z in 3 Days 00:17:23 The "Dark Period": Building Without Users 00:22:23 Structuring Enterprise Design Partnerships 00:28:48 The "2-Hour Bootcamp" Sales Strategy 00:31:03 Why the Org Chart is Flat (15 Reports to CTO) 00:34:02 Converting Pilots to Commercial Contracts 00:41:07 The Moment of True Product Market Fit Send me a message to let me know what you think!

    45 min
  4. He raised $150M with $0 revenue. Then hit $1M ARR in 4 months. | Michel Tricot, Co-Founder of Airbyte

    MAR 2

    He raised $150M with $0 revenue. Then hit $1M ARR in 4 months. | Michel Tricot, Co-Founder of Airbyte

    Michel raised $185M and achieved a unicorn valuation before he fully cracked monetization. How? By building a community so strong it broke his engineering team. In this episode, Michel breaks down the chaotic journey from a failed YC marketing idea to becoming the standard for open-source data movement. He reveals why he killed a high-growth fintech product, how he used the "Magic Wand" question to find his true direction, and the specific insight that allowed Airbyte to hit $1M ARR in just 4 months after launching their enterprise product. Why You Should Listen How to hit $1M ARR in 4 months with a bare-bones product.The "Magic Wand" framework for validating startup ideas.Why you should sometimes optimize for Vanity Metrics.How to raise $150M+ by solving the "build vs buy" dilemma.The critical difference between Project Market Fit and Product Market Fit.Keywords startup podcast, startup podcast for founders, open source business model, data infrastructure, product market fit, Y Combinator, pivoting, fundraising, developer tools, Airbyte 00:00:00 Intro 00:09:37 The Failed Marketing Product & COVID Pivot 00:16:13 The "Magic Wand" Framework for Ideas 00:20:52 Launching Open Source to Solve "Build vs Buy" 00:24:39 Bootstrapping a Community on Reddit & Hacker News 00:30:17 Why Too Many Users Broke the Team 00:34:32 Project Market Fit vs. Product Market Fit 00:36:16 Hitting $1M ARR in 4 Months 00:37:53 Managing a Unicorn Valuation Without Revenue 00:41:20 Advice for Early Stage Founders Send me a message to let me know what you think!

    43 min
  5. He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails

    FEB 26

    He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails

    Didi spent five years building a product that no one really wanted. He raised $10 million, tried endless pivots, and was known as the "black sheep" of his investors' portfolio. Then, with his back against the wall, he made one final bet on a boring, unsexy market: FP&A for Excel users. In this episode, Didi breaks down how that final pivot turned into a rocket ship. He reveals why he sold cheap monthly contracts to prove demand, how he used his kids to automate LinkedIn outreach, and why targeting the market everyone else ignores (Excel lovers) was the key to unlocking massive growth. Why You Should Listen How to survive 5 years of wandering before finding PMF.Why he sold $790/month contracts to validate a pivot.How to scale from $0 to $20M ARR with 100% outbound sales.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, pivot, B2B sales, outbound sales strategy, FP&A software, excel automation, Didi Gurfinkel 00:00:00 Intro 00:02:42 The First 5 Years of Wandering 00:11:39 Being the "Black Sheep" of the Portfolio 00:14:12 Identifying the FP&A Opportunity 00:20:55 The Pivot: Selling $790/Month Contracts 00:30:30 Scaling from $1M to $20M with Outbound 00:33:18 Why the Mid-Market is Wide Open 00:34:22 The Moment of True Product Market Fit Send me a message to let me know what you think!

    38 min
  6. His startup powers OpenAI's Voice Mode. Last month, they became a unicorn. | Russ d’Sa, Co-Founder of LiveKit

    FEB 23

    His startup powers OpenAI's Voice Mode. Last month, they became a unicorn. | Russ d’Sa, Co-Founder of LiveKit

    Russ was running a moderately successful live streaming startup. Then he got a terrifying offer from a tech giant: sell to us for cheap, or we'll crush you. He had no leverage. He was about to fold. Then he got an email from OpenAI. They had secretly built ChatGPT's voice mode on his infrastructure. Overnight, everything changed.  In this episode, Russ reveals the wild story of how LiveKit became the backbone of multimodal AI, why he almost sold his previous company for parts, and how to survive when the biggest companies in the world are breathing down your neck. Why You Should Listen How to secretly power ChatGPT’s voice mode.Why you should build "boring" infrastructure instead of AI apps.How to negotiate an acquihire when you have no leverage.Why a "sell or die" threat from a tech giant was the best thing to happen.How to pivot from a failed consumer app to a unicorn infrastructure play.Keywords startup podcast, startup podcast for founders, product market fit, AI infrastructure, multimodal AI, OpenAI, ChatGPT voice mode, founder stories, pivot, LiveKit 00:00:00 Intro 00:02:49 The OG YC Batch Experience 00:07:08 How to Sell a Failing Startup 00:15:51 The "Good Cop, Bad Cop" Investor Negotiation 00:35:56 The First Voice AI Demo That Flopped 00:38:29 The Secret Email from OpenAI 00:43:47 How to Scale Stateful Voice Agents Send me a message to let me know what you think!

    55 min
  7. He pivoted at $1M ARR—then raised $120M. | Kevin Tian, Co-Founder of Doppel

    FEB 19

    He pivoted at $1M ARR—then raised $120M. | Kevin Tian, Co-Founder of Doppel

    Kevin was building a successful startup in the NFT space. They'd hit $1M ARR. But he looked at the market and realized it wasn't big enough. So he made the terrifying choice to pivot the entire company into cybersecurity. In this episode, Kevin breaks down how he navigated that transition without killing the business. He reveals how he sold his first $5k/month contract with no product, why he raised a massive seed round he didn't need, and how he convinced Andreessen Horowitz to lead his Series A in the middle of a strategic shift. Why You Should Listen How to pivot from a bad market to a unicorn opportunity.Why he sold a $5k/month contract with zero product.How to raise a Series A from a16z during a pivot.Why you never truly "find" Product Market Fit.The danger of building for a niche market (and how to escape).Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, pivot, cybersecurity, crypto startup, a16z, raising series a, Kevin Tian 00:00:00 Intro 00:02:17 Meeting at Uber and the "Glass Eating" Phase 00:07:21 The First Idea 00:11:52 Selling the First $5k/Month Contract with No Product 00:16:52 The Decision to Pivot at $1M ARR 00:29:43 Network Selling to Enterprise Cybersecurity 00:32:03 Raising Series A from a16z During a Pivot 00:33:36 Why Product Market Fit is Not a One-Time Event 00:35:10 Action Produces Insights Send me a message to let me know what you think!

    36 min
  8. He sold his first startup for $100M. Then raised $250M in 18 months. | Dileep Thazhmon, Founder of Jeeves

    FEB 16

    He sold his first startup for $100M. Then raised $250M in 18 months. | Dileep Thazhmon, Founder of Jeeves

    Dileep sold his first company for over $100M. For his second act, he didn't just want another win; he wanted to solve a problem that banks refused to touch: global business banking. In this episode, Dileep breaks down how Jeeves scaled to $7M ARR in just over a year by doing things that "don't scale"—like physically mailing credit cards to Argentina.  He reveals the counterintuitive strategy of raising from dozens of small investors, how to pivot a fintech when interest rates skyrocket, and why being an outsider was his biggest advantage in building a global banking infrastructure from scratch. Why You Should Listen How to get to $7M ARR in one year through unscalable acts.Why a "messy" cap table with 50+ investors is actually a secret weapon.The "Beat Down" Framework: A brutal stress test for vetting your idea.The offline marketing stunt that actually worked.Keywords startup podcast, startup podcast for founders, product market fit, fintech startup, global expansion, second time founder, Y Combinator, fundraising strategy, B2B banking, finding pmf 00:00:00 Intro 00:02:04 Selling His First Company for $100M 00:08:19 The "Beat Down" Framework for New Ideas 00:19:38 The One Metric That Matters for PMF 00:24:44 Why Join YC as a Second-Time Founder? 00:29:15 Shipping Cards to Argentina by Hand 00:39:13 The Pivot to Jeeves Pay When Cards Got Shut Down 00:43:25 The "Messy Cap Table" Fundraising Strategy 00:49:27 The Moment of True Product Market Fit Send me a message to let me know what you think!

    56 min
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About

Every founder has 1 goal: find product-market fit. We interview the world's most successful startup founders on the 0 to 1 part of their journeys. We've had the founders of Reddit, Gusto, Rappi, Glean, Cohere, Huntress, ID.me and many more. We go deep with entrepreneurs & VCs to provide detailed examples you can steal.  Our goal is to understand product-market fit better than anyone on the planet. Rated one of the world's top startup podcasts.

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