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

Sep 28, 2026

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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