Side Hustle School is a daily podcast written and hosted by Chris Guillebeau, the New York Times bestselling author of The $100 Startup. It publishes a new episode every day (91 episodes in the last 90 days, as of October 2026), and episodes usually run about 7 minutes.
The feed describes the show as a daily show for everyone who works a regular job and wants to start an income-earning project on the side. Each episode features a different story of someone who started a side hustle, with what went well, how that person overcame challenges and what happened as a result.
Recent episode titles show a few repeating formats: Q&A episodes that answer a listener question (for example about deducting side hustle losses or starting to resell), "TBT" throwback stories, "First $1,000" segments and "Failure Friday" stories. The story episodes cover small businesses such as pumpkin carving, house sketches and dachshund apparel.
Our take: this is a good fit if you have a day job and want short, daily examples of side businesses rather than long interviews. At around seven minutes an episode it is easy to fit into a commute. If you want longer founder conversations, our list of best side hustle podcasts covers more formats.
We have no YouTube view data for this show, so these are recent episodes that show its main formats, chosen from their titles and descriptions.
Built This Week is our show, with Jordan Metzner and Sam Nadler: the hosts build something with AI on air every week, test new AI tools, interview a founder or operator and cover AI news. Side Hustle School gives you a quick daily story, while ours is a weekly episode with a build in it. For more picks, see best side hustle podcasts and best podcasts for entrepreneurs or the full list of best podcasts.
Show details on this page come from the public listings and feeds below, checked on October 24, 2026.
Side Hustle School is written and hosted by Chris Guillebeau, the New York Times bestselling author of The $100 Startup.
Daily. The feed shows 91 episodes in the last 90 days, as of October 2026.
Episodes usually run about 7 minutes.
The show has thousands of short episodes. Good starting points are the story episodes, such as the pumpkin carving and dachshund apparel businesses, and the listener Q&A episodes.
Indie Hackers, Starter Story, My First Million and The Startup Ideas Podcast also cover small and early-stage businesses.
