Watch the creators. Understand the context. Find your own angle.
290 episodes
Katelyn Gleason is founder and CEO of Eligible, a healthcare/insurance data and API company in a heavily regulated industry. She explains…
Josh Kaufman, author of The Personal MBA, distills the core concepts that show up across every successful business. The conversation covers…
David Smooke, longtime media operator, bootstrapped Hacker Noon and the @ami publishing network to 600k subscribers and 10M monthly…
Joel Runyon discusses pulling himself up with no obvious skills into a portfolio of businesses by picking interesting problems and…
Austen Allred, after going through a failed company, created Lambda School, an income-share-agreement coding bootcamp that became a sizable…
Max Lytvyn co-founded Grammarly by starting from a vision for an AI writing assistant and bootstrapping it into a business with hundreds of…
Stephanie Hurlburt co-founded Binomial, a 2-person startup selling software to game studios, after quitting her job and landing consulting…
Pieter Levels built and runs Nomad List plus a portfolio of side businesses targeting digital nomads, partly by leaning into the fear of…
Brothers Gareth and Jonathan Bull bootstrapped EmailOctopus, an email marketing service competing against giants like Mailchimp. They cover…
Vincent Woo is the programmer behind CoderPad, a side project he grew into a $2M business. The conversation covers how he skipped the…
Spenser Skates, CEO of Amplitude, explains how he deliberately prepared to become a founder — internships, learning, networking — and then…
Amir Salihefendic, founder of Doist (Todoist, Twist), recounts the decade-long journey from a dorm-room to-do app to a remote-first company…
Dawson Whitfield built Logojoy (later Looka), an AI logo generator that made $30,000 in its first month and grew from there. The episode…
Jesse Patel walks through WorkFlowy's path from a free outliner to roughly $800,000/year in revenue, achieved as a tiny team. He is candid…
David Darmanin tells how two failed startups led to Hotjar, which grew to roughly $10 million in revenue within two and a half years by…
Designer-turned-founder Tobias van Schneider (Semplice, among other products) talks about his pattern of going against convention in…
Mike Carson runs Park.io, a service that catches and resells expired .io domain names, and was making roughly $125,000/month solo at the…
Philippe Lehoux, founder of MissiveApp.com, talks about a long track record of starting and selling profitable web projects, most recently…
Peter and Calvin from Segment describe what product-market fit felt like before and after they found it, including the early struggles…
Kevin McArdle left his corporate job at 38 and co-founded SureSwift Capital, an acquisition firm that bought nearly 30 small SaaS and…
Vivek Ravisankar, co-founder of HackerRank, recounts the company's path from several failed startups in India to a platform with roughly…
Tracy Osborn of Hello Web Design describes how repeated perseverance — learning to code, refusing to quit — led her from a borderline…
Wes Bos explains how he built and runs a collection of programming courses reaching around 100,000 students as a one-man operation, walking…
Thomas Smale, founder of M&A brokerage FE International, explains what he has learned about buying and selling online businesses, including…
