A Product Market Fit Show | Startup Podcast for Founders

Cos was the CTO of Brex, which he helped scale from 40 people to over 1,000. Before that, he led engineering at Stripe. When he finally left, he had no startup idea—just a co-founder he trusted and one rule: whatever they built had to have massive impact. Six months of brainstorming later, they landed on accounting. In this episode, Cos breaks down why he capped the company at 21 people after rais...

Anurag was employee #8 at Stripe, set for life and free to do anything next. Instead he spent a year and a half hunting for a problem worth decades of his life. He chose to build a product to make it simple for developers to ship apps, going head-to-head with AWS. In this episode, Anurag breaks down how he hit $10M ARR in 4 years with zero marketing spend, why refusing to launch a free tier was hi...

George had to wind down his last startup and give investors their money back. He went deep into the valley of despair, certain he'd missed his window to build something big. Then he met a co-founder, decided to start over, and started selling. In this episode, George breaks down how a customer signed a $36K pilot off nothing but a Loom and a one-pager, how cold email took him from zero to $1M...

Dan founded and scaled a $50M ARR, SoftBank-backed startup—and could've stayed to make tens of millions. Instead, he handed it to his chief of staff and started from scratch. He wanted something bigger. He took an entry-level paralegal job to learn everything about law hands on. Then he built Manifest, which just raised a $60M Series A. In this episode, Dan breaks down why he did intake calls...

Ali quit his job a few months after ChatGPT launched, convinced AI would eat labor marketplaces like Upwork. With no co-founder and no code, he collected $12K from real customers—using a faked demo and a cloned voice. Then he pitched 100 VCs in 10 days and got 47 straight 'no's. In this episode, Ali breaks down how he banked $12K in revenue before writing a single line of code, how a $20...

Mark was running a startup out of a tiny annex office in Dublin with zero product usage. Then one customer turned it on and overnight he saw usage spike to thousands of simulations. He got to $1M ARR 100% through outbound, by sending 500,000 cold emails. A few months ago he closed a $25M Series A. In this episode, Mark breaks down the pivot from sales roleplay to customer support that unlocked his...

The AI boom is making founders feel like the market is wide open, but the data tells a sharper story: valuations are up, round sizes are bigger, and the bar to “count” in a top-tier fund’s Monday meeting keeps rising. We sit down with Peter to translate Q1 2026 venture capital trends into founder reality, from seed-stage pricing distortions driven by AI infrastructure to the quieter pressure build...

I meet 1,000+ founders every year. Most are bad at fundraising. I also interview 100+ of the world's best founders on my podcast each year. Most are incredible at fundraising. One raised $14M in 17 days. another was 3x oversubscribed on a $3M round. another closed a seed in hours from a single X post. All are first-time, unproven founders. They don't waste time becoming "friends&quo...

Surojit spent 14 years at Google building mobile ads into a $100B+ business and then took Coinbase public as Chief Product Officer in 2021. In early 2023, before "agent" was even a word in AI papers, he started Ema in stealth—betting on a future where teams of AI agents would replace the "human glue" inside Fortune 500s. In this episode, Surojit breaks down how a Hitachi deploy...

Sean was spending four days a week inside customer warehouses at Amazon Shipping when he noticed the same thing everywhere: back-office admin staff churning every six months, buried under the same repetitive claims and reshipping tasks. He talked to eighty-five warehouse owners, quit Amazon in July 2024, and cold emailed his way to a pre-seed round within weeks. In this episode, Sean breaks down w...

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 mar...

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 billboar...

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 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...

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 ente...

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. In this episode, Maju breaks down why 40% of e-commerce traffic loses its context the moment it arrives on a brand...

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 s...

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 jus...

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...

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...

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 h...

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 chos...

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...

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,...

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....

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...