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This Week in Startups · September 28, 2026 · 40m

Jason’s Put a $5K Bounty on His Dream Chrome Extension | E2338

Jason put up a $5,000 bounty to build a Chrome extension he's wanted for 20 years: a tool that lets users highlight any sentence on the web and dispute it. The episode works through three demo submissions from the TWiST audience: Robert's annotated.wtf, Alan Shiflett's annotated.bytetalk.ai/feed, and Chirag Asarpota's annotaed.com. Along the way, Jason and Lon discuss how dramatically software costs have fallen and what made one of the submissions stand out. The show closes with an Ask Jason call from an unhoused founder raising money for two pre-revenue startups.

This summary was generated from show notes and public descriptions, not from a full transcript review. Details may contain inaccuracies.

Preview

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The cost of building software has collapsed00:00:33
Jason says the annotation product would have cost $500,000 to build in 2006 and now costs less than a used car.
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Highlight and dispute any sentence on the web00:00:33
The original idea behind the bounty is a browser extension that lets users highlight any sentence and dispute it, and Jason says he's been sitting on it for 20 years.

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