A Product Market Fit Show | Startup Podcast for Founders

Alex spent two years building AirOps nights and weekends during the pandemic before raising a single dollar. A chance conversation with Sam Altman—while walking down the street during SF Pride—sent him down the LLM rabbit hole months before ChatGPT existed. He pivoted his product toward AI, picked marketers as his customer, and never looked back. In this episode, Alex breaks down why he picked marketers over every other AI use case after watching them build 80-step workflows on his platform, the consultative sales motion that converts almost every pilot to annual at $60K–$250K ACVs, and why positioning—not product—was the unlock that took AirOps from $1M to $13M ARR. Why You Should Listen Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, AI marketing, content engineering, SEO, AEO, AI search, enterprise sales, SaaS growth, AirOps, Alex Halliday, Greylock Chapters Send me a message to let me know what you think!

Isaiah pivoted mid-YC, landed in the bottom 10% of his batch, and watched 180 investors say no—their reason: phone calls won't exist a year from now. Voice AI was not yet a thing. With almost no money left, he and his co-founder bet everything on building AI phone calls from scratch. Bland went from pre-seed to a $40M Series B in a year. In this episode, Isaiah breaks down how a $60K billboard and a strategic influencer campaign generated close to a billion impressions, why he fired 50% of his customers right after raising a Series A, and the enterprise sales playbook that lands six- and seven-figure contracts with companies most people have never heard of. Why You Should Listen Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, voice AI, AI phone calls, enterprise sales, Bland AI, YC pivot, billboard marketing, influencer marketing, call center automation, Isaiah Granet Chapters Send me a message to let me know what you think!

Anada Lakra just raised a $21M Series A for BoldVoice, a $150/year pronunciation app that helps immigrants speak English with confidence. But she started from zero in her Harvard dorm room, with no technical co-founder and a problem most VCs didn't think was big enough. She recruited a Hollywood accent coach, shipped a bare-bones V1, and got into YC. In this episode, Anada breaks down why she launched a consumer app when every investor was chasing B2B, how a Reddit thread called "Judge My Accent" became an early growth hack, and why switching to annual-default pricing transformed her unit economics overnight. Why You Should Listen Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, consumer app, B2C startup, pronunciation app, accent coaching, AI app, YC startup, mobile app growth, Anada Lakra, BoldVoice Chapters Send me a message to let me know what you think!

Bobby launched Protege in early 2024 to connect data holders with AI model builders. He raised a $10M seed with almost no demand pipeline. A year later, Protege jumped 30x to $30M in GMV and raised $30M from a16z. In this episode, Bobby breaks down how he built a 250-partner data network by leveraging prior healthcare relationships, why he flies from New York every week to close seven-figure enterprise deals, and why the "texting terms" litmus test tells you if a deal is real. Why You Should Listen Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, AI data, enterprise sales, founder-led sales, data licensing, healthcare AI, a16z, B2B startup, Bobby Samuels, Protege Chapters Send me a message to let me know what you think!

Maju ran Prime fulfillment technology for all of Amazon — same-day, one-hour shipping, global logistics during the pandemic. He became CEO at Bolt. Then he walked away to start Spangle in a basement with a co-founder, convinced AI could replace e-commerce infrastructure as we know it. Less than a year out of stealth, he raised a $50M Series A. In this episode, Maju breaks down why 40% of e-commerce traffic loses its context the moment it arrives on a brand's site, how Spangle's AI dynamically rebuilds the entire storefront in real time for each visitor, and why he believes the future of commerce will be a battle between AI seller agents and AI buyer agents. Why You Should Listen Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, e-commerce, AI commerce, agentic commerce, personalization, dynamic storefronts, conversion optimization, enterprise SaaS, Series A, Spangle, Maju Kuruvilla Chapters Send me a message to let me know what you think!

Amanda spent 16 years running a services business for Cisco and Intel. When she tried to productize her business, 22 VCs rejected her. That became 6sense, a $200M ARR company. After stepping aside as CEO and taking five years off, she's back with an AI startup called 1 mind. In this episode, Amanda breaks down why she always goes enterprise-first when everyone tells her to start small, how she used an AI clone of herself to pitch 60 VCs and raise 1mind's Series A in three days, and why she believes the entire sales process—SDRs, AEs, sales engineers—is about to be collapsed into a single AI "superhuman." Why You Should Listen Keywords startup podcast, startup podcast for founders, product market fit, AI agents, AI sales, enterprise sales, 6sense, 1mind, finding pmf, B2B SaaS, AI enabled services, net dollar retention Chapters Send me a message to let me know what you think!

Tarek already built a B2B software company to $30M ARR. But when the AI wave hit, he realized he could build a generational business by automating the manual world of accounts receivable. So, he left to start Stuut. In this episode, Tarek breaks down how he reached $1M ARR in a couple of months and is on track to hit up to $50M this year. He reveals how he pre-sold his first $65k contract with just wireframes, why he forces new customers to introduce him to five peers, and the brutal reality of finding message-market fit through hundreds of cold calls. Why You Should Listen 00:00:00 Intro 00:01:41 Leaving a $30M Startup to Build with AI 00:08:06 Finding Message Market Fit Through Cold Calling 00:20:07 Pre-Selling a $65k Contract with Wireframes 00:27:51 The Voice AI "Aha" Moment 00:33:07 The Closing Discount Referral Hack 00:37:18 The Brutal Reality of B2B Sales 00:42:19 Hitting $1M ARR and Pacing for $50M 00:45:05 Why Product Market Fit is Never Truly Found Send me a message to let me know what you think!

Description Bhaskar was employee #1 at AppDynamics, which was sold to Cisco for $3.7B. He and co-founder Jyoti found a way to change how enterprise monitoring tools worked. From tracking low-level code metrics that ops teams didn't understand to monitoring what the business actually cares about. In this episode, Bhaskar breaks down how that one insight won them Netflix and Priceline as early customers, why they ran production POCs that no competitor would dare try, and how a free download called AppDynamics Lite generated over 60% of their leads—in an industry where getting started normally took weeks of professional services and six-figure contracts. Why You Should Listen Keywords startup podcast, startup podcast for founders, product market fit, AppDynamics, application monitoring, enterprise SaaS, B2B sales, finding pmf, freemium strategy, Cisco acquisition, production POC Chapters Send me a message to let me know what you think!

Yogi spent 20 years living the nightmare of enterprise accounting. As a senior finance leader at Rubrik, he watched highly paid professionals spend three weeks every month manually wrangling data into spreadsheets—a problem that caused mass burnout and multi-million dollar stock corrections. When ChatGPT launched, Yogi knew the technology was finally ready to solve the problem. In this episode, he breaks down how he left his executive track to found Maxima, how he landed massive enterprises like Scale AI and Rippling as early design partners, and why he managed to raise $41M from top-tier VCs like Kleiner Perkins and Redpoint before he even had a pitch deck. Why You Should Listen Keywords startup podcast, startup podcast for founders, AI in accounting, enterprise SaaS, product market fit, finding pmf, raising seed round, raising series a, B2B sales, design partners 00:00:00 Intro 00:07:37 Leaving a CFO Track to Become a Founder 00:11:52 Raising an $11M Seed Round from Kleiner Perkins 00:20:07 The Design Partner Playbook 00:22:34 Why You Must Charge Your Early Design Partners 00:28:36 The Aha Moment for Product Market Fit 00:33:20 Selling "Folded Laundry" Instead of "Digital Shelves" 00:36:47 Raising a $30M Series A Pre-Emptively Send me a message to let me know what you think!

Helen was a software engineer who noticed a massive problem: accounting software for startups was broken, manual, and weeks out of date. Instead of just building a shiny new dashboard on top of legacy platforms, she decided to completely replace the offshore accounting model with AI. In this episode, Helen breaks down how she raised a $4.7M seed round pre-product as a solo founder and why she chose to build an AI-enabled service instead of pure software. She reveals the exact user research playbook she used across 200 interviews, how to rebuild a monopoly like QuickBooks, why hitting product-market fit actually forced her to stop taking new customers, and how she raised a $15M Series A. Why You Should Listen Keywords startup podcast, startup podcast for founders, product market fit, AI enabled services, fintech startup, user research, solo founder, raising seed round, B2B SaaS, finding pmf 00:00:00 Intro 00:02:13 The Origin Story 00:05:31 Doing 200 User Interviews Before Building 00:11:49 The "Magic Wand" Framework for User Research 00:14:33 Raising a $4.7M Seed as a Solo Founder 00:22:27 Why AI-Enabled Services Beat Pure SaaS 00:28:50 Rebuilding QuickBooks from Scratch 00:39:34 The Public Launch and PR Strategy 00:50:06 Why Saying "Yes" to Customers Hurt Growth 00:53:46 The Moment of True Product Market Fit Send me a message to let me know what you think!

Omar already built and sold an AI startup for over $100M. But when the generative AI wave hit, he realized the technology wasn't just the future of software—it was the future of labor. So he started Eudia to completely transform how enterprise legal teams operate. In this episode, Omar breaks down how he scaled from $2M to $20M ARR in just 12 months. He reveals the exact cold email strategy he used to land C-suite design partners, why he bought an existing legal services company to accelerate his AI platform, and why replacing human labor with AI is the ultimate business model. Why You Should Listen Keywords startup podcast, startup podcast for founders, AI startups, product market fit, AI enabled services, legaltech, B2B SaaS, enterprise sales, finding pmf, generative AI 00:00:00 Intro 00:01:45 Why AI is the Future of Labor 00:04:55 Replacing In-House vs. Outsourced Legal Teams 00:09:35 Selling His First AI Startup for $100M 00:12:11 Why the $1 Trillion Law Firm Industry is at Risk 00:21:59 Landing Fortune 500 Design Partners via Cold Email 00:28:26 Playing to Win vs. Playing Not to Lose 00:33:45 Raising a $6M Seed Round with an 80-Page Transcript 00:38:53 Buying a Legal Services Company to Accelerate Growth 00:44:55 Scaling from $2M to $20M ARR in 12 Months Send me a message to let me know what you think!

Mateo had already built a successful food company in Argentina. But he wanted more. So he moved to New York with no network, no credibility, and a dream to build the "Spotify for Food." The first two years were messy. He nearly ran out of money multiple times, relied on corporate expense accounts to keep the lights on, and failed a major expansion into LA. But then, he noticed a strange behavior: some customers were ordering 10 meals at a time. That single insight led to a massive pivot, a partnership with world-class chefs, and eventually, a $750M run rate. In this episode, Mateo breaks down the gritty reality of building a marketplace from scratch, how to survive the "messy middle," and why sometimes you have to kill your revenue to save your company. Why You Should Listen Keywords startup podcast, startup podcast for founders, product market fit, food tech, marketplace startups, pivot, founder story, CookUnity, scaling a startup, immigrant founder 00:00:00 Intro 00:02:50 Moving from Argentina to New York 00:07:43 Why Leave a Successful Business? 00:13:37 The "Airbnb for Food" Vision 00:22:44 Faking Traction with Corporate Stipends 00:28:41 The $2M Pivot: Shutting Down On-Demand 00:34:54 Why Unit Economics Mattered More Than Revenue 00:42:14 The COVID Inflection Point & Chef Partnerships 00:48:09 Failing Fast in LA vs. Succeeding Later 00:51:54 The Moment of True Product Market Fit Send me a message to let me know what you think!

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 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!

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 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!

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 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!

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 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!

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 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!

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 a random Gmail account. It was 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 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!

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 duringKeywords 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!

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 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!