Jason’s Put a $5K Bounty on His Dream Chrome Extension | E2338
This Week in Startups
September 28, 2026
This Week In Startups is made possible by: 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.
Speakers Jason Calacanis, Molly Wood, Johnny Detail
TopicsTechnology
Jason Calacanis (0:00)
All right, it's time, Lon, for us to reveal round one of our bounty program for annotated.com.
I own the domain name annotated.com. I had literally bought this for 30 or 40 grand after I sold my second company, Weblogs Inc., to AOL. And I said, my next startup is going to 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. Because I had been hit with a lot of copyright issues and because we were doing blogs and gadget, Autoblog, Joystick, well, these are great blogs. Shout out to Peter Rojas and Ryan and Sean Gold and of course Brian Alvey. 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 billion-dollar startup. Well, here we are. It's 20 years later. I forgot I had the domain name.
I forgot I had bought it. And then Vibe coding happens and I say, 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. Now 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 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. Now, if you could, Lon, be so kind, to explain the broad strokes of this, this is a $5,000 bounty. You're going to have to pay tax. You're going to have to submit your stuff. If you don't want the money, donate it to somebody. I don't know. But I own, whatever code you write is open source, is I guess the rule. And I have complete control of the contest. I can cancel it if everything sucks. I can give two prizes. I can split the prize. I can do whatever I want is the idea here.
Basically. So caveat, caveat, caveat, ship it, win, 5K. Tell us what we got.
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Molly Wood (3:18)
All right, so we've got three entries to go through today. Well, hard to distinguish between them. I'll just use the creator names because they're all called annotated or variations of it. Our first one comes from Robert. He did not give us the last name. It's annotated.wtf.
This works with X, it works with YouTube videos, it works with articles. Though with articles, you were saying your dream version was you could just take a little bit of the article, highlight it, and then discuss just that segment. The way Robert's works, you could share the article. So we haven't yet drilled it down into share just this quote. You could share the article and give your thoughts, and then you could say, of course, the author says this one sentence and I disagree with that. So we do have a demo prepped and ready to go.
Jason Calacanis (4:03)
So this is annotated.wtf. We'll call this Submission 1 So officially Submission 1
Let's take a look here at what they built and you can sportscast it.
Molly Wood (4:13)
I will be happy to. Let's roll Robert's demo. So as you can see, we're on this CNN article about the Six Flags roller coaster that, oh, I read about this.
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