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

September 28, 2026

AI Summary

5 min read

Jason Calacanis bought the domain Annotated.com for $30,000 to $40,000 nearly 20 years ago, after selling his second company, Weblog, to AOL. His vision then was a Chrome extension that would let users highlight any piece of text on the web—a sentence from a Wall Street Journal story—and dispute it, add context, or give an opinion. Other people could then join the discussion on that same page. He thought it would be his billion-dollar startup. It never launched. He forgot he owned the domain. Then vibe coding happened.

Now, Calacanis has put a $5,000 bounty on that same idea, betting that modern AI coding tools let a solo developer ship in a week or two what would have cost $500,000 and six months two decades ago. In the first round of the contest, three submissions came in, and all of them are close to production-ready. This episode of This Week in Startups walks through each entry, scores them, and reveals Calacanis's next move: he is considering incubating the winning product inside his own venture firm.

The $5,000 Bounty and the Vibe Coding Thesis

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What you'll learn

1 (00:10) **The Annotated Vision & $5K Vibe-Coding Bounty** - Jason Calacanis explains his 20-year-old idea for a web annotation tool, the domain Annotated.com, and his $5,000 bounty to have it built quickly using modern AI/vibe-coding tools.
2 (03:22) **Submission #1 (Robert): Annotated.wtf - The Early Favorite** - The hosts review the first entry, which features a clean sidebar, a highlighter metaphor, and works with X, YouTube, and articles.
3 (10:00) **Deep Dive on Submission #1: X Integration & Preservation** - The review continues with a demo of the extension on X (Twitter), highlighting its seamless integration and a key feature for content preservation.
4 (13:04) **Submission #2 (Alan Schifflet): Social Network Features** - The second entry is reviewed, which includes a social media profile, follower counts, and a main feed, but falls short on the presentation of the annotation itself.
5 (16:17) **Submission #3 (Chirag Azarpooda): Annotated.com (One N) & Demo Lessons** - The final entry is reviewed, which owns the misspelled domain name. The review focuses on a key lesson for founders about the importance of demo examples.
6 (23:55) **Round 1 Conclusion & Round 2 Announcement** - Jason gives his current ranking (80% to #1, 20% to #2) and announces a Round 2 in two weeks, hinting at a potential plan to incubate the winning project as a startup.
7 (30:53) **Mass Chase: Advice for a Homeless Founder** - A listener video from a homeless man named Johnny DeTale asks for advice on raising funding for his two pre-revenue startups.

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Guests on this episode

Jason Calacanis

Show Notes

This Week In Startups is made possible by: Every.io: http://every.io/ Northwest Registered Agent: www.northwestregisteredagent.com/twistdomain Sentry: http://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: