A Product Market Fit Show | Startup Podcast for Founders

Rahul ran a sleep clinic that lived and died by insurance paperwork. He sold it, then built the tool he wished it had. Two customers signed on before Assured was even incorporated. Five months in, four new customers landed in one week and the founders couldn't onboard them all. Twelve months in, they hit $1M ARR. Assured just raised a $19M Series A.

In this episode, Rahul breaks down why his team skipped AI SDRs for six human BDRs making 150 to 200 calls a day, how doing discovery before the demo took their close rate from 18% to 40%, and...

Tushar gave his app away for free. It spread to 200 locations. Almost nobody used it, and nobody paid a single dollar. So he started charging from day one, with a one-month pilot that rolled into a full annual contract. In Q4 2025, his team closed more revenue than in the two years before. Delightree just raised $25M.

In this episode, Tushar breaks down the three questions he used to qualify every customer, how turning a dusty ops binder into TikTok-style training became his biggest source of leads, and why his best cold email was a screenshot of the...

Hermann wanted to build Stripe for phone plans. Every carrier said no and investors passed. So he plugged into an aggregator with terrible economics and sold to kids' smartwatch makers losing 30 to 40% of devices to returns. That niche paid for his seed and Series A. Then AT&T opened the door. Today Gigs powers phone plans for Revolut, Klarna, Nubank and Cash App and wins 90% of the deals it goes after.

In this episode, Hermann breaks down why a small niche with a sharp pain point beats a big market with a mild one, how a founder...

Daniel Saks built AppDirect into a marketplace moving upwards of $10B a year in gross merchandise value. Now he runs Landbase, an AI go-to-market company with data on 40 million startups, and it just raised a $30M Series A. So when he talks about cold outbound, he is not guessing. He is reading what actually happens across millions of messages. He also spent two years in a windowless room building an app store for Bell Canada that launched to crickets. Harley from Shopify messaged him: the Bell business app store has less traffic than my intern's blog.

In...

Jonathan quit his job in early 2023 with no idea and no co-founder. Tim agreed to join only if he raised $3M. He lined up 75 investor meetings a month in advance. SVB crashed on day four and 40% of his meetings canceled. He closed the round anyway, then won 20 deals in a row, one of them a seven-figure deal with FIS. Baselayer just raised a $20M Series A.

In this episode, Jonathan breaks down the 20-minute reply rule he holds every employee to, why he asks buyers if they have ever wanted to be a founder and then introduces...

Most investors told Nick not to hire a salesperson before he had product market fit. He hired the top rep in legal tech anyway and called him a product market fit finder. That rep signed a paid five-year deal in his first week, over lunch. By the time Sandstone came out of stealth, they had done hundreds of demos and had $10M+ of pipeline waiting. Sandstone just raised a $30M Series A.

In this episode, Nick breaks down why the intros he never asked for were the moment he knew PMF was real, how sitting next to...

Dan's first app made over $1M in two months. Then Facebook sent a cease and desist and killed it. His next company, Mode Mobile, grew revenue 32,481% in three years and ranked #1 on the Deloitte Fast 500. Then his crypto advertisers went bankrupt, revenue fell from $25M to $8M, and he cut half his staff. No VC wanted a declining Series B. So he raised $5M from his own users in three months—then $75M more.

In this episode, Dan breaks down how paying people to use their phone actually makes money, why revenue concentration and not growth is wh...

Keith raised a $43M Series B for Tome. The product had 20 million users. But retention was terrible and nobody cared enough to complain. So he turned it off before he knew what he'd build next, went from 70 people to 7, and started over. Lightfield just closed a $47M Series A.

In this episode, Keith breaks down how he knew Tome would never grow up, why customers lighting up your Slack at 3am is the signal you actually want, and the exact playbook he used to sell an AI-native CRM to YC founders before he charged them a dollar.<...

Aaron started Vestwell in 2016. Two years in, he had $500K in ARR and an investor asking if it would ever make money. During the 2021 bull market, VCs told him 401ks were too boring—they were busy chasing crypto. Then Morgan Stanley signed. Today Vestwell has 2.5 million people saving on the platform, over $200M in ARR, and just raised $385M at a $2B valuation.

In this episode, Aaron breaks down why he white-labeled everything instead of building his own brand, how losing the JP Morgan bid as a 40-person startup still turned into one of his largest partnerships, an...

Andrew spent two and a half years selling AI contract review to lawyers. It stalled at $800K. He rebuilt the company around finance teams and grew that to $10M. Then he demoed a little internal tool on the side at his own conference, and nobody wanted to talk about anything else. It did $350K in five weeks. He sold the $10M business and went all in on the side tool—Within went from zero to nearly $20M in 18 months.

In this episode, Andrew breaks down the 30-and-100 rule he uses to validate every idea, how he turned ev...

AJ spent two years selling health benefits with no customers and no references. His competitors told buyers their service was free. He charged a flat fee and told the truth about where the money actually went. Two years in, at $10M ARR, a Fortune 500 company called him. Judi Health just raised $400M at a $3.25B valuation.

In this episode, AJ breaks down how he beat three Fortune 15 giants by operating 70% more efficiently, why he spent zero on marketing for two years and let customers sell for him, and the one hiring signal he refuses to ask about...

Niklas quit law school to install CCTV cameras in iPhone repair shops. Eight years later he sold that business to private equity at 26. Then he went after the most boring software in the world: the 1997 tool engineers use to design the wiring and plumbing inside buildings. He spent $150K on a website before he had a product and DM'd engineers on Reddit to find his first users. His first month of sales was $1.5M, all enterprise. Endra has now raised $75M, including a $50M Series A led by a16z.

In this episode, Niklas breaks down why...

Colin spent eight years building Looker into a $2.7B Google acquisition. Then he left to compete with his own product. He thought traction would take a month—it took nine. A hundred demos got him five verbally-committed customers, and he lost all five. So he spent two months killing bugs, went on one podcast, and won every single trial that came out of it. Omni just raised over $250M.

In this episode, Colin breaks down how to tell the difference between a product that's genuinely better and one the market just doesn't want, why founding with $30M di...

Rafael launched a crypto insurance product in 47 states, backed by a real carrier. Everyone told him it was genius. Nobody needed it. He shut it down with $2M left in the bank, fired almost everyone, and rebuilt with two engineers on $20K a month. Notch just raised $30M.

In this episode, Rafael breaks down how a POC he entered through the back door turned into a seven-figure contract, why "isn't everyone doing this?" is the feedback you actually want, and how to tell whether an enterprise deal makes you a real company or just their dev shop.<...

Ben and his co-founder had no product, no law enforcement background, and no pitch—just an offer to help detectives solve cases. One commander took a chance, handed them background checks, and said "let's see what you can do." They worked out of that police department every day for 18 months. Peregrine just raised $250M at a $6.8B valuation.

In this episode, Ben breaks down how researching every police captain in the Bay Area landed their first design partner, why working as free crime analysts for 18 months was "the purest form of method acting," how forward-deployed engineers drove th...

Damien left his job to start a startup solo. Two years later, Nebulock closed a $25M Series A. In between: 90 customer interviews in 90 days, a year of design partners, and a Fortune 500 deal that closed in 6 weeks.

In this episode, Damien breaks down how his 90-in-90 customer discovery sprint killed his original architecture before he wasted money building it, how his design partner program converted 100% into paying customers, and how a POC playbook needing just 2 hours of customer time closed a Fortune 500 in 6 weeks.

Why You Should Listen

Astro has run X, Alphabet's Moonshot Factory, for 16 years. His teams created Waymo, Wing, and Google Brain—by testing over 1,000 ideas a decade and killing nearly all of them. His whole system rests on one uncomfortable rule: celebrate the people who kill their own projects.

In this episode, Astro breaks down why you should do the hard thing first, how pre-written kill criteria force intellectual honesty, and why X maximizes learning per dollar instead of progress—and never tracks whose idea it was.

Why You Should Listen

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 raising $75M, why everyone—engineers and salespeople alike—earns the exact same salary, how he hit a 100% pilot-to-production conversion rate with top accounting firms, and the counterintuitive process he use...

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 his most expensive mistake, and how putting engineers on customer support rotations quietly shaped the entire product roadmap.

Why...