Dillan interviews Daniel Vassallo—an ex-Amazon engineer who quit the 9-5 grind to pursue building his own projects online.

Daniel runs the Small Bets community, with thousands of creators and entrepreneurs who want to make low-risk, low-pressure experiments when it comes to building online businesses.

They discuss: why Daniel hates Y-Combinator, what a "small bet" actually is, Daniel's biggest business mistakes, why Daniel quit his cushy job at Amazon, why most entrepreneurs fail, what woodworking taught Daniel about building businesses, how to structure your workflows, how Daniel accidentally started a profitable online community, tips for building a strong online community, how Daniel sold access to his calendar, and much more.

Daniel's links:
Twitter / X: https://x.com/dvassallo
Small Bets: https://smallbets.com/

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Follow Dillan on the interwebs:
Twitter / X: https://x.com/dillanroytaylor
Newsletter: https://newsletter.grindstone.work/

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0:00 Intro
1:07 Daniel hates YC
7:03 Why he quit Amazon
21:18 Worst-case scenario
28:28 Dose & frequency
40:31 High vs low motivation tasks
48:22 Burning the boats
52:58 Your "why" doesn't matter
58:04 How Small Bets started
1:15:06 Online community tips
1:31:32 Daniel's latest small bet