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

An episode of [This Week in Startups](https://invisiblenetwork.ai/podcast/315114957), 28 Sep 2026, 41 min.

Audio: https://pscrb.fm/rss/p/traffic.megaphone.fm/LTANT5475492100.mp3

This Week In Startups is made possible by: Every.io: https://every.io/ Northwest Registered Agent: https://www.northwestregisteredagent.com/twistdomain Sentry: https://sentry.io/twist Today’s show: A product that would have cost $500,000 to build in 2006 now costs less than a used car. Jason put up $5,000 on an idea he'd been sitting on for 20 years, and so far, we’ve received dozens of amazing submissions from vibecode experts. See how well the Top 3 demos fare, and which app was so good, Jason’s already thinking about spinning it off into a startup. PLUS, an unhoused founder calls in asking how to raise money for not one but two pre-revenue startups? Hear Jason and Lon’s advice. Submissions: Submission 1 — https://annotated.wtf By Robert Submission 2 — https://annotated.bytetalk.ai/feed By Alan Shiflett Alan on X: https://x.com/alanshiflett Submission 3 — https://anotated.com/ By Chirag Asarpota Chirag on X: https://x.com/ChiragAsarpota Relevant Links: annotated.com bounty brief — https://annotated.lovable.app/ All active TWiST bounties — https://www.thisweekinstartups.com/bo... The other open $5,000 bounty: a sidebar companion app for podcasts — https://www.notion.so/launch1/5K-Boun... Timestamps: 00:00:00 Why Jason bought annotated.com 00:00:33 The original idea: highlight any sentence on the web and dispute it 00:01:25 The rules: the code is open source, and Jason can cancel any time 00:02:06 Submission 1: Robert's annotated.wtf 00:10:08 Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit https://every.io 00:12:13 Submission 1 Scoring 00:12:28 Submission 2: Allan Shifflet's take 00:13:56 What it got right: profiles, follower counts, trending topics 00:16:40 Submission 3: annotaed.com, and buying the typo domain on purpose 00:20:20 Northwest Registered Agent - Got a new business idea? Northwest Registered Agent helps you bring it to life. Get a free domain, email, phone number, and more - with no purchase required! Learn more at https://www.northwestregisteredagent.... 00:23:26 Final scores, and how to enter round two 00:24:48 Incubating annotated inside a venture firm 00:29:46 Sentry - New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST 00:30:18 Ask Jason: a homeless founder with two startup ideas Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Jason: X: / jason LinkedIn: / jasoncalacanis

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