A handyman grows his part-time business to $4,000/month on TaskRabbit, then transitions off the platform to avoid fees and keep clients…
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4,471 episodes
A Failure Friday segment about a listener who borrowed money from a friend to invest in a cryptocurrency project, which did not work out.…
Five ways to make money, then a grab bag: profitable fan-fiction IP plays, vice businesses (alcohol/cannabis/ gambling-adjacent), Group…
A Thanksgiving special recorded in South Africa where host Chris Guillebeau reflects on five-plus years of running Side Hustle School and…
Damon Chen of Testimonial covers failed side projects, idea validation, the qualities of a good website testimonial, charging premium…
Jack Butcher (Visualize Value) explains his pivot from running a design agency to building products for a community he understood: testing…
Bryan Johnson (Braintree → PayPal) on his background, financial plans, where he puts his money, what Kernel (brain-interface) does, his…
A Texas event planner builds a side business earning at least $2,000/month, with one early event featuring a floor-to-ceiling display of…
A Failure Friday story about an investor who bought into a national franchise and realized he had effectively purchased a job. The episode…
Short mindset episode: the 'billionaire framework for making hard decisions', a 'do the hard thing' principle, and a section on mapping…
David Perell (Write of Passage founder) joins Greg to discuss building Write of Passage, having a bad 2-year plan but a great 10-year plan,…
Andrew Wilkinson of Tiny talks about his portfolio (Pixel Union, AeroPress, cat furniture via Primitive), ranks businesses from hardest to…
Recap of the FTX collapse — what happened, the business background, the SBF / Elon connection, the distrust it created, and Sam and Shaan's…
The 'Wordpress Girl' runs a service helping female entrepreneurs get set up with websites, currently rebranding while still earning at…
A Failure Friday segment about a tech employee who launched an after-hours side hustle and came to regret it, reportedly because telling…
Sahil Bloom (ex-private-equity, creator/investor) on three profitable business ideas he's pitching now, why he left PE to make millions as…
Shaan and Sam react to the fake Twitter employees who trolled media with 'Ligma + Johnson' pranks inside Twitter's HQ during the Elon…
Kaitlyn Michelle Siragusa, known as Amouranth, explains how she built a $40M social media business empire, her team, prior career, fame…
A listener uses Instagram DMs as a sales channel to earn up to $4,000 a month without a large personal following. The segment explains the…
A coach builds her business on a Facebook page with 40,000 followers, then clicks a phishing password-reset link and loses the account. The…
Sam and Shaan interview Kevin Rose about his roughly $100M/year watch magazine Hodinkee, lessons from selling Digg.com, his Web3 bets and…
Eight seasonal side hustles teased across the episode: Halloween-spend research, Zombie Pumpkins (custom-carved pumpkins), a VR haunted…
Eric Turner of Japan Dev talks about living in Japan as a foreigner and visiting as a tourist, picking a lucrative niche, and growing a…
A college student resells MacBooks part-time and has systematized it to about $1,000 a week in profit. The segment covers sourcing,…











