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This Week in Startups · Monday, September 28, 2026

Jason Calacanis Launches $5,000 Bounty for Dream Chrome Extension

Jason Calacanis has announced a $5,000 bounty program for the development of a Chrome extension for his domain Annotated.com. The extension aims to allow users to highlight text on any webpage and add disputes or additional content, a concept Calacanis conceived two decades ago.

personJason CalacanispersonPeter RojaspersonRyanpersonSean GoldpersonBrian AlveycompanyWeblogs InccompanyAOL

The tape

2 quotes
“I said, my next startup is gonna annotate the web. And my idea is, you could highlight any piece of text and then you could dispute that piece of text or give additional content. Right. Because I had been hit with a lot of copyright issues and because we were doing blogs and auto blogs, Joystick, these are great blogs. Uh, shout out to Peter Rojas and Ryan and Sean Gold and of course, Brian Alvey. Uh, very successful business. I said, this could be my next business because I don't have to do the content. But there'll be a story in the Wall Street Journal, you highlight two sentences and then you give your opinion on it, and then other people can go to that page and give their opinion. And I just thought, this could be my, it's going to be my billion dollar startup. Well, here we are. It's 20 years later. And I forgot I had the domain name. Uh, forgot I had bought it. And then vibe coding happens. Man, I said, you know what I want to do? I want to put out a $5,000 bounty for people to make me, finally, my Chrome extension.”
“This would normally have cost $20 years ago, $500,000 to build. Maybe five years ago, I could have done it with an offshore group for $250, maybe two years ago, I could have done it for $50,000. But right now, just putting out a $5,000 bounty. I think you can get, this is my premise. Vibe coding folks, people using these tools to build it in a week or two. And then at least I would get, let's say the $5,000 doesn't result in a final product. At least I get ideas. Yeah. And we get some show content. And that's really my goal here. That's what Annotated.com is. I see it as a Chrome sidebar, as you can see here on the website, premium domain. And I said, just for this contest, we want somebody to execute my idea, as explained on the website, and then make a Chrome extension.”
Heard on This Week in Startups — “Jason’s Put a $5K Bounty on His Dream Chrome Extension | E2338”, published Monday, September 28, 2026. Heardvine summarizes and quotes with attribution and timestamps, and links to the original everywhere.
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Jason Calacanis Launches $5,000 Bounty for Dream Chrome Extension — Heardvine