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

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: 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: 0:00 Why Jason bought annotated.com 0:33 The original idea: highlight any sentence on the web and dispute it 1:25 The rules: the code is open source, and Jason can cancel any time 2:06 Submission 1: Robert's annotated.wtf 9:31 Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit https://every.io11:36 Submission 1 Scoring 11:51 Submission 2: Allan Shifflet's take 13:19 What it got right: profiles, follower counts, trending topics 16:03 Submission 3: annotaed.com, and buying the typo domain on purpose 19:43 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....22:49 Final scores, and how to enter round two 24:11 Incubating annotated inside a venture firm 29:09 Sentry - New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST 29:41 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

• 0:00Speaker 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.

• 0:33Speaker 01

  Right.

• 0:34Speaker 00

  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 can be my, it's going to be my billion dollar startup. Well, here we are. It's 20 years later. I forgot I had the domain name. Forgot I had bought it and then vibe coding happens. And 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.

• 1:16Speaker 00

  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.

• 1:43Speaker 01

  Yeah.

• 1:43Speaker 00

  And we get some show content.

• 1:45Speaker 01

  Sure.

• 1:45Speaker 00

  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, it's 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.

• 2:30Speaker 00

  I can give two prizes, I can split the prize, I can do whatever I want is the idea here.

• 2:35Speaker 01

  Basically, yeah.

• 2:36Speaker 00

  Basically. So caveat, caveat, caveat. Ship it, win 5K. Tell us what we got.

• 2:42Speaker 02

  This week in startups is brought to you by Sentry. Your team should be focused on shipping features, not chasing down bugs. New users can get $240 in free credits when they go to sentry.io/twist and use the code twist 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 www.northwestregisteredagent.com/twistdomain. Every, for all of your incorporation, banking, payroll, benefits, accounting, taxes, or other back office administration needs, visit every.io.

• 3:18Speaker 01

  All right. So we've got three entries to go through today. 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 a 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, 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, he's, the author says this one sentence and I disagree with that. So we do have a demo prepped and ready to go.

• 4:03Speaker 00

  Okay, so this is annotated.wtf. We'll call this submission one.

• 4:08Speaker 01

  Submission one.

• 4:08Speaker 00

  This is officially submission one. Let's take a look here at what they built and you can sportscast it.

• 4:13Speaker 01

  I will be happy to. Let's roll Robert's demo. So as you can see, we're on this, the CNN article about the Six Flags roller coaster that, oh, I read about this. This was the, there was a roller coaster that they're saying over the years, X2, I believe it's called, and it was knocking people around that they were actually developing brain injuries that were requiring medical attention over the years. So that is the article that we have found here. We are annotating that article and as you can see, we've pulled it up. It's, it's in the sidebar and now we're on the annotated page and we're leaving a comment. I can't believe people are getting injured by roller coasters in 2026.

• 4:54Speaker 01

  And now the demo is even progressing and we can see you can also edit a.

• 4:59Speaker 00

  So it created a page at annotated.wtf for the handle at twi startups.com slash, and then a slug.

• 5:09Speaker 01

  Right.

• 5:10Speaker 00

  On-six-flags-roller-coaster, yada, yada.

• 5:12Speaker 01

  You are.

• 5:13Speaker 00

  And here they said, the annotation is at the top. I cannot believe people are still getting injured by roller coasters. How is this still happening in 2026? That's the comment from the individual. And then below it is an image from the page. And then when he scrolls down, it has a link to that source. On the top left, we see the person can hit the edit button and very nicely done. And I like the sidebar. The sidebar and the design of this is very appealing to me. And it actually used a highlighter metaphor. I like this branding idea. This was actually my original idea was to use a yellow highlighter as the iconography of it. And so this person picked up on that, which I'll say is a somewhat obvious idea Lon.

• 5:56Speaker 00

  And he's highlighted and he has the marker there annotated.wtf. And on the side, you know, he says, hey, select 30 to 1,000 characters on the page. The quote will appear here, yada, yada. Very well constructed, easy to use.

• 6:09Speaker 01

  Yes.

• 6:10Speaker 00

  I would have put a screenshot of the webpage and then the quote underneath it, but I never thought putting the quote up top and then the screenshot below it. Interesting design choice. I guess that's something we could A/B test. Let's go on to the next piece and look at clipping a video. This is a very controversial one. You know, if you clip a video, some people might be like, hey, that's my video. Of course, there is fair use, so you get to clip a little bit of a video these days.

• 6:39Speaker 01

  I actually feel like this, it's a generational thing. Our, our era, the idea of taking a piece of someone else's video and then resharing it was like, oh, I don't know, that makes me a little uncomfortable. You should just link back to them. But today clipping has become such an art form unto itself and maybe arguably the best way to share content to make it get wider attention. I feel like people have less of an issue with it now. I feel like you can clip people's things and as long as you're giving them credit, it's not, you know, more than a few minutes of the, the original content. I think that's okay.

• 7:11Speaker 00

  I think you're right. If it's a percentage of the original, that doesn't preclude somebody from watching the original and it's clear you're not the owner, as it would be on a website called annotated. And if you're doing fair use, the four part test for fair use, you can look up, but one of them is you're doing criticism here. So taking the whole episode, no bueno. I would say taking, you know, I don't know, two minutes would be just fine with any podcaster. Let's see what we got. So here, and show on the sidebar, nice and slow, what the person's doing.

• 7:42Speaker 01

  Sure. I would also note you, there is a file acclaim button at the bottom. If you feel like somebody has clipped too much of your original work and you're a little salty about it.

• 7:51Speaker 00

  Okay.

• 7:52Speaker 01

  So yeah, like take a look, we're, we're in the sidebar. Let's get it playing again. And you can see that they're, they're now leaving a comment. I thought Puniet's demo was super sick on this episode. Now they are marking the source and there it is. It's live and you could go visit the page and see the segment of the video that they clipped. It's processing right now. There's the headline once again. I thought Puniet's demo was super sick. There's the content right underneath it and then a comment thread where other people, I think this is really the magic of your concept and how we could see it going and becoming like a destination to itself, is that almost like old school aggregation sites,

• 8:33Speaker 01

  your, your digs, your fark.com's, your reddits, one person's annotation and comment on this video could then lead you into a whole discussion thread, a vibrant community of people talking about each other's links.

• 8:46Speaker 00

  Hmm. Yes, very nicely done. And I saw, if we scroll back a little bit, he did give the starting time and

• 8:55Speaker 01

  Correct.

• 8:56Speaker 00

  Closing time, if you go back to when he's first clipping it, there you go. And he's just picking, he wants 42 minutes and 51 seconds to 44. So he set the start, he set the end, and he clipped it. I love that part.

• 9:10Speaker 01

  Yeah, this one, actually, a lot of the annotated, a lot of the annotated that we saw had this clipping feature, and sometimes it was awkward to navigate. This one, very clean, as you can see.

• 9:23Speaker 00

  Okay. Yeah, wow, this is great.

• 9:25Speaker 01

  Yeah. He did a really nice job. This one is pretty slick. So now, we're on X.com, the everything app. This is a post from Jason with a chart. And again, we're doing the same thing. They're gonna add their comment. What's your take on the tweet? More men need to lock TF in.

• 9:46Speaker 00

  FN.

• 9:47Speaker 01

  Yeah. And now, that's it. Super fast. I mean, you can see, and I like that, too. If you go back a little bit, the post to X, you could take your comment and post your comment as a new post to X. So it's sort of integrating X workflow within annotated without ever leaving. You could just keep the conversation going. That's very nice.

• 10:07Speaker 00

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• 10:52Speaker 00

  Plus, you're gonna get 3% cash back on every dollar when you use your Every corporate card. So, head over to every.io and stop wasting time on stuff that isn't growing your company. That's E V E R Y dot I O. Every dot I O. This is kind of the vision. This would have taken 20 years ago, six months to build. Five years ago, would have taken three months to build and to get the, you know, 1.0 out. And now, it takes but two weeks or less. Well done.

• 11:26Speaker 01

  Yeah.

• 11:27Speaker 00

  And there's a feed at the top. So obviously, if things were trending, or were today, or maybe an AI-based algorithm, maybe just take the Twitter algorithm, the X.com algorithm is now open source. You could just go to the feed. Here, you have people going to the feed. And I'm wondering if it takes a screenshot of the tweet, so it's preserved forever? Because that's one of the problems is

• 11:50Speaker 01

  Oh, interesting. You're right.

• 11:51Speaker 00

  I think that's an image. Or it might, maybe they're just embedding the image. Are you on the live site right now?

• 11:57Speaker 01

  This is a pre-recorded demo that you're seeing. Oh.

• 12:00Speaker 00

  No, I think he moved to the live site.

• 12:01Speaker 01

  Oh, well, there you go.

• 12:02Speaker 00

  Okay, so your producer Jacob's on the live site. If you right mouse click on that, is that an embed from? Yeah, that's an embed from Twitter. So that's an interesting way to do it. It's an embed from Twitter because you're hitting the light.

• 12:14Speaker 01

  Right, yeah, it's active, yeah.

• 12:16Speaker 00

  What I would do here, I'm just gonna give a little punch up. I would give the user the ability to embed Twitter, do a screenshot, or both. Maybe a little too advanced, but absolutely fantastic.

• 12:30Speaker 01

  Well, the screenshot idea, because so many things get pulled off of Twitter, deleted, people think better of it. That's why you would be, a screenshot would be a savvy move there. Because then you could

• 12:40Speaker 00

  Correct.

• 12:40Speaker 01

  Annotated would be your way of preserving a hot tweet that you think might get pulled.

• 12:44Speaker 00

  All right. I'm gonna give this one on a score, eight and a half out of 10.

• 12:49Speaker 01

  Yeah, it's very strong.

• 12:50Speaker 00

  I mean, it feels close to production ready. I have a tiny couple of little things. I mean, I guess we have to test it. But my lord, you're logged in with the This Week in Startups account and using it. My lord, this is fantastic. I want to give it an 8.5 of 10. Let's go to our next demo.

• 13:04Speaker 01

  All right. Our next demo comes to us from Alan Schifflett, number two.

• 13:09Speaker 00

  Okay.

• 13:09Speaker 01

  It's another take, there he is, there's Alan. It's another take on annotated.

• 13:13Speaker 00

  Beautiful landing.

• 13:14Speaker 01

  And as you can see, he also, I was gonna say this before, but I figured I'd say it. He also did come up with the highlighter branding. As you can see right here, publish the annotation. So we're gonna, we're gonna log in here. We're going to, it's a CNN page about Dolly Parton. Poor Dolly Parton. It's about her, her health struggle highlights a crisis that faces millions of American caregivers. They're leaving our comment. Dolly Parton's legacy includes an unfortunate reality of caregiving, not taking care of oneself. Oh, that's just, they're pulling that in from CNN. That's the article headline.

• 13:46Speaker 00

  Yes.

• 13:47Speaker 01

  So then, we're moving down here.

• 13:49Speaker 00

  And they write a snarky, I guess I'm too young to know who this is. And we get to the article page, like the permalink page. It's a, okay.

• 13:58Speaker 01

  Going a little fast.

• 13:58Speaker 00

  Decent. Let's go back here to the

• 14:02Speaker 01

  To this page.

• 14:04Speaker 00

  Well, no, go back one. This is the feed page of all of them. The permalink page is this one. So here, the issue with this one is, it just gives you the headline there. Then you have the comment, a bit confusing what's going on. I think a better way to do this would to take a screenshot of the CNN page and put that there. And then underneath, it put the comment. And then, you know, you have the picture of the person, Jacob there, producer Jacob. I guess I'm too young to know who it is. And I like the fact that it has on the right hand, who annotated it, how many annotations they have, how many followers they have. That's part of this. So what this one got right, is the social media profile

• 14:44Speaker 00

  on the right, and the follower count, and all that great stuff. The left, I would have put an actual screenshot of the CNN page.

• 14:53Speaker 01

  Yeah.

• 14:53Speaker 00

  Or like a thumbnail of it, or something.

• 14:55Speaker 01

  I have to say, this also makes kind of the argument for putting the comment up top. Because it's hard to know, just from looking at this. It looks like

• 15:03Speaker 00

  What's going on?

• 15:03Speaker 01

  Yeah. It looks like this page is just a link to this CNN article, and then a comment thread underneath it. Whereas

• 15:09Speaker 00

  So work to be done.

• 15:10Speaker 01

  Yeah, a little, a little, I think that, I like the other, the annotated dot WTF approach of making the comment, the annotation is the star. The link is, here's what I'm talking about, is the context.

• 15:22Speaker 00

  So this is submission two. Let's go ahead and see what's next.

• 15:25Speaker 01

  This is you talking about the mosquito laser iron dome for mosquitoes to protect your backyard. And then leaving a comment, need one of these, but for hornets, please. Jacob's having some hornet troubles, I guess. So he

• 15:39Speaker 00

  Got it. Okay, so here we go. They're taking and annotating a tweet.

• 15:43Speaker 01

  Oh, I like this. Hang on, pause. Go back a little bit, Jacob. I want to highlight something on that screen I didn't notice. I like this. Did you see there's, you could categorize. You're leaving a hot take, it's a fact check, you're steel manning the argument, you found receipts, it's an explainer. I like that very much, that you can tag, here's the kind

• 16:01Speaker 00

  Plus one for that.

• 16:01Speaker 01

  Yeah, here's the kind of annotation that I'm leaving. That's a nice feature.

• 16:05Speaker 00

  Yeah, plus one for that.

• 16:06Speaker 01

  All right, you can keep going.

• 16:07Speaker 00

  The page is a little bit kludgy on the left, and there's your main feed.

• 16:11Speaker 01

  What is

• 16:12Speaker 00

  I like the idea of a main feed, but yeah, it needs to be better.

• 16:14Speaker 01

  What is that 21 in parentheses before your at name? I don't even know what that is.

• 16:18Speaker 00

  I think they're just pulling the tweet, like metadata, and some stuff's getting pulled in.

• 16:24Speaker 01

  Okay, yeah. Because that, that does not look great. That looks a little weird.

• 16:28Speaker 00

  Hey, listen, this is like a V1, so that should be cleaned up a bit. But I do like ideas, multiply when they're shared on the bottom left. I like invite to annotated. I would have made that, put in somebody's email, and you can just invite them.

• 16:43Speaker 01

  Sure.

• 16:44Speaker 00

  I like people worth following on the top right, trending topics on the right-hand bar. All of this is somebody who understands that this is supposed to be a social network of sorts for people annotating stuff. So very well done.

• 16:58Speaker 01

  I also, if you look at the very top left, the plans for a for you algorithmic feed, like annotated with learn over time, the kinds of topics and stories that interest you. That's very promising, that this could be another way to just source and discover what's going on in my feed.

• 17:15Speaker 00

  Fantastic. Well done.

• 17:16Speaker 01

  We have our third submission here, annotated.com, with just one N to set it apart. It's by Charag Azarpota. He bought the domain, he actually bought this domain, Jason, annotated with one N, in case people misspell it and still want to access the site.

• 17:32Speaker 00

  Great. Hijack my traffic.

• 17:34Speaker 01

  There you go. So yeah, you've got a competitor.

• 17:36Speaker 00

  You're learning something.

• 17:37Speaker 01

  Yeah. All right. So he's on another CNN article. Trump's ambassador to Italy is cruising the Mediterranean on a $450 million yacht. That lucky so-and-so.

• 17:47Speaker 00

  Fair enough. Well, you buy ambassadorships. That's how it works. When you get an ambassadorship, it usually goes to people who have donated a lot. But then, you're responsible for funding. I have a friend who did this. You have to fund the actual embassy yourself personally, is my understanding.

• 18:03Speaker 01

  Wait, really?

• 18:03Speaker 00

  So if you get Italy, or you get Japan, look it up, you've got to pay for the maintenance of the embassy

• 18:11Speaker 01

  Wow.

• 18:11Speaker 00

  And the staff, and the food and everything. So it costs you five or 10 million bucks at a pocket, at a pocket, or to your partners, or whatever. So it's not, it's, there's nothing free.

• 18:22Speaker 01

  That's a crazy system. I would assume the government is, anyway. So back to annotated. We could talk about that all day. I'm fascinated. But the building, maintenance, security, and salaries are taken care by the sending country's government. But ambassadors are expected to host receptions, dinners, and other events, and budgets don't usually cover that. So you are right. The ambassadors are paying a lot for like, when they have state dinners, or whatever. And anyway, anyway, let's get back to annotated. So as you can see, they've got the sidebar up. They're leaving a comment, a thoughtful comment about this Italy cruise. It's taking one last look. It gives them, you know, like sort of a moment to, hey, check up on what we're doing. Now, it prompts signing into the annotated.com

• 19:04Speaker 01

  service. That's something new. We haven't seen on any of the others. And then, here we go. Here's how the annotated page, like, kind of a, kind of an X.com Twitter formulation on this one.

• 19:14Speaker 00

  Looks good.

• 19:15Speaker 01

  It does. It looks smart.

• 19:16Speaker 00

  I kind of like this one best so far. Again, for the CNN, if we go back, you know, you have the comment up top. It's very clear who. What you see here is, you know it's from Jacob, because it's his icon. Underneath it, you kind of know that's his comment. Then you have the quote from the page, Trump ambassadors, yada, yada. So when you do this demo, the fact that it's just highlighting the headline, poorly done demo, what you would want to do is pick a paragraph and comment on a paragraph. Then it would be more clear what was going on here. But that's the fault of the user. Then below it, you have, in the box, the CNN story. I would have made that CNN box have a thumbnail of the page, which you can

• 20:00Speaker 00

  do. There's many services that will do that. And then you could have a little more of, about the story there. But otherwise, great. And it has the date and the time and everything. You have trending sources on the right.

• 20:13Speaker 01

  Yeah, I like that.

• 20:13Speaker 00

  Home Explorer profile saved. I mean, and you can join the conversation. It's absolutely solid effort, solid effort. Regular listeners already know that if you've got a great idea for a new business, our friends at Northwest Registered Agent want to help you bring it to life. They're going to be the most amazing partner you've ever had. Even if you're not ready to form an LLC, you still need to take care of some basics. So Northwest Registered Agent is now offering free identity services. That means a free domain name, open source website hosting, a business email, and a phone number and everything else that's going to make your new startup look and feel like a professional company, all with no purchase required. And you know, you can rely on Northwest because they've been helping people like you start businesses for nearly 30 years.

• 20:57Speaker 00

  If you have an idea, you can't get out of your head. Or even if you're already building something amazing, you already got started. Northwest Registered Agent is the best way to establish your new company. Learn more at northwestregisteredagent.com/twistdomain. The problem here, Lon, is with these demos generally is that the examples are bad. And this is a good lesson to just highlight for founders. When you do a demo of your product, if you do a janky example, it's hard for people to understand it. So what you want to do here is say, hey, in, you know, this article has the third paragraph. There's a really important to be point to be made that the ambassadors,

• 21:41Speaker 00

  let's say, have to pay for the parties. You highlight that portion and then you say, I didn't know that ambassador is a really interesting concept here going on. So whoever made the demos, great that you made a smoothest demo. It shows everything, but you gotta remember my rule of startup founders presenting a product. Examples matter. Examples matter. Examples matter.

• 22:04Speaker 01

  Yeah, like that Duarkesh article about agent civilizations. A lot of people were doing this with that, where they were pulling out, oh, see how we phrase this one sentence in here? That makes it anthropomorphized or whatever. That's a good example of how people are really using services and platforms like this.

• 22:20Speaker 00

  Yes, like that would be a better one to do. Uh, we're going to do a video one. So they picked a This Week in Startups episode.

• 22:26Speaker 01

  Yeah, this is a recent VC roundtable. That's Shiel Manot.

• 22:29Speaker 00

  Okay. Oh, you mark the part you want in the actual, yeah, you put in the, you put the timestamp in yourself like it's manually.

• 22:35Speaker 01

  Yeah, it's a, it's a, this one, I remember this now. This one, it's a lit, this is one of the more kluge ones I was talking about, where that other one, the original one we looked at WTF, it's very neat. It's like this little app and you just drag and drag. And it is like using QuickTime or something. It's very intuitive. This one less. So you gotta really exactly find the time code you want. It's a little, it's two extra steps.

• 22:58Speaker 00

  Correct. Okay. Uh, good enough, though. Let's see what happens when you actually hit continue. Yeah, I continue there. Uh, when you actually do it, what happens?

• 23:09Speaker 01

  And that's when you, you type in your reaction. Shiel is, oh, I missed it. Something about Shiel.

• 23:15Speaker 00

  Yeah, note is live. And you notice like when the note's live, you have to go view the note. It should just take you to view, you know, like this is like a little UX thing. Why are we making the person do another click? It should say, your note's posted. This is the permalink for it. Invite people to it. That's an opportunity to move on to the next step. Here we go. You can share this note. Let's scroll up a little bit. Oh, and here's file a claim.

• 23:37Speaker 01

  Right. If you, if, if we were like, hey, they stole our episode of, oh, there we go. Jay, Shiel is an absolute god on X.

• 23:44Speaker 00

  Great. Awesome. Um, all right. So, um, the first one's like an eight and a half. The second one's like a, an eight, and this one's like a six, just in terms of refinement, design, et cetera. So I don't know if anybody else is going to submit to this, but if you want to beat these three, we're going to do a round two in two weeks. So two weeks from whenever this is published, you got 15 days or so, whatever the next episode is, and then we'll review round two. After round two, I might do a round three, but I'll probably just pick at that point. Right now, if I was going to pick, I would probably give right now, before round two, I probably would have given 80% to number one and 20% to number two. Just in terms of like, you know, a lot of good ideas there. Maybe I would give 70, 30, 60, 40. I'm not sure.

• 24:28Speaker 00

  But that's where my kind of gut is right now. Lon, what did you think? Do you have a ranking here?

• 24:33Speaker 01

  Oh, I absolutely agree. The number one WTF Robert submission. It's been my favorite all along. Like, we've been looking at these and vetting them as they come in for, I would say, a few weeks now, close to a month. And that was one of the first ones I saw. And all along I was like, this is the one. It, the, the Chrome extension is so easy. Everything is just intuitive. It's really pretty. Like, it really looks like, it doesn't look vibe coded. It looks like a real professional website. So that's, that's always been consistently, unless somebody is out there ready to top it, I'm ready to give the prize to, to Robert.

• 25:09Speaker 00

  Well, now here's the next thing. I would like you to maybe, um, when we get past round two and we get the last round of feedback, I actually want somebody to talk to the founders. See if anybody, I think what I want to do is take this and incubate it inside of our venture firm and see if we can make it into a startup. I think that's going to be my next step is maybe we could actually build this as a startup, start using it. And I, venture capital firms in their documents can incubate a company. You can actually form a company and like Sax did that with his, was it Glue? His AI-based version of Sax, uh, you know, so you can put a couple of million bucks

• 25:51Speaker 00

  in a $300 million fund, let's say, towards an internally baked, uh, company. In fact, I think Snowflake was an internally baked company inside of a venture firm, which is incredible. And then how does it work? Well, the founder of the venture firm might take 50% ownership. They might give, you know, 10 or 20% ownership to their LPs for having put up the seed money. And then they go hire a team and give them 20, 30, 40, 50% of the company. And as long as the investors got first bite of the apple and they got a reasonable valuation, everybody feels very good about it. So that's what I'm thinking. That's where my heart is at with this. I, I think this could be a public service. That's one possibility.

• 26:34Speaker 00

  I think this could also be done as a social network. Just let it grow. If you lose $250,000 a year in server costs, just let it grow and see if it becomes the next, you know, Reddit slash Twitter-esque kind of thing. And then there's a third option, which is, I've been thinking, what if you put a bounty on a story? And you said, I would love for Lon to vet this story. And I'd love him to annotate this story. Uh, so it's my story, right? I, I wrote a blog post. I would love to get Lon to annotate it. I would love to have this story in the New York Times fact-checked for me. And then there's the final piece, which is, you know, we have Micro One that's doing, uh, data for LLMs.

• 27:19Speaker 01

  Yeah.

• 27:19Speaker 00

  I think this eventually could have a data component where if you did have people commenting on objects on the web that were important, you could actually say to a large language model company, hey, here's every legal case that got published on the web today. And we're just going to let lawyers publicly annotate them and give them some share of the money or some tokens or something. And you use like, maybe you give that data to Micro One to resell or to any of the data ones, or you just make it a public service.

• 27:50Speaker 01

  Well, yeah, it's that vital context that so many LLMs are missing. They have all of this, they have all of this writing in them, but they don't have that expertise layer of, here's what this is an example of. Here's what kind of writing this is. Here's how this writing could have been improved. Like, that's exactly what people are doing on annotated just for funsies.

• 28:08Speaker 00

  Mm-hmm. Correct. Uh, all right. Well, this has been an amazing, uh, round one. Round one is now complete for annotated.com and we will go to round two. 15 days, two weeks, basically, after this airs. So whatever day this airs, two weeks from then, the next episode of This Week in Startups will have this. So if we do this on one Monday, it'll probably be two weeks and then a Wednesday, something to that effect.

• 28:32Speaker 01

  Something mid to late September.

• 28:35Speaker 00

  And, uh, listen, we did this once before.

• 28:37Speaker 01

  We did.

• 28:39Speaker 00

  And, uh, we, we gave the money. So what was the first project?

• 28:42Speaker 01

  It was live commentary, AI providing live commentary on a podcast. And we had personas, like there would be like the Joker, there would be.

• 28:52Speaker 00

  Didn't work.

• 28:54Speaker 01

  Mostly.

• 28:55Speaker 00

  I mean, it was proof of concepts, but it wasn't like this project. Those, the result of the first bounty was a lot of proof of concepts, which are good, a lot of good ideas, but not a shipped product. What I like about this time is we've now upped it a level. I think all three of these are kind of ready to ship, at least on the web, maybe not on mobile, but they're ready to ship on the web. In fact, one of them is, or maybe all three are. So now we've heightened the game here and the tools are getting better. So this will be our second bounty contest. You can look at all the bounties, thisweekinstartups.com/bounty or slash bounties, either of those plural or singular. And you can go to annotated.com, which explains the contest, all of these rules, blah, blah, blah, blah.

• 29:38Speaker 00

  Are subject to change and it's J. Cal's money. So yada, yada, yada.

• 29:43Speaker 01

  We're, we're, we decide how we want to do it.

• 29:45Speaker 00

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• 30:26Speaker 00

  It can even take a look at your code before it ships and warn you if any problems are likely. Try Seer and Sentry for free. If you're a This Week in Startups listener at sentry.io/twist, use the code TWIST for $240 in Sentry credits. Make sure you use that code, make sure you use that URL, sentry.io/twist, so they know your Uncle J. Cal sent you. I got time for an answer.

• 30:50Speaker 01

  You want to do some answers, Jason? All right, we're just going to do one. I want to do this one. It's from a guy named Johnny Detail. He is living on the streets, Jason. He is a homeless man, but he wants to ask your advice on becoming a founder. Let's play that video.

• 31:06Speaker 00

  Well, come on, man. You guys putting me on here or something?

• 31:08Speaker 01

  I mean.

• 31:09Speaker 00

  Okay, okay, okay. I try to be right context here.

• 31:12Speaker 03

  Last month and a half, and I have two startup ideas that are pretty much fully digitally built out. They have about 700 pages in total between the two of them.

• 31:28Speaker 03

  And they're ready to make some money, but the only thing is I'm pre-revenue and I'm just getting started. So my question to you guys is what challenges do you think could be foreseeable in the future trying to raise money?

• 31:46Speaker 03

  And how could I overcome them? And what is it that investors are looking for whenever investing in two start, a founder with two startup companies that are both pre-revenue? And what are the odds of both of them being funded?

• 32:04Speaker 00

  Okay.

• 32:06Speaker 00

  All right. Well, that's something I was not expecting.

• 32:09Speaker 01

  I thought you were doing a joke or a bit or something.

• 32:12Speaker 00

  Not a bit. We take the guy at his word that he's down on his luck. He's homeless. Hopefully he has a place to sleep, shelter, whatever, but he's written 700 pages. I'm assuming that's like a business plan, a deal memo, et cetera. That's not going to cut it in today's environment. Step one is to get yourself a skill that is marketable and get yourself safely off the street. Hopefully there are some places you can go. Hopefully my team maybe can find some resources here for this gentleman. I would say job one is, and I'm going to get mocked for this online, but I'm being dead serious. If you can use AI tools and get a job first,

• 32:55Speaker 00

  and then get a small apartment and stabilize and be hireable for a specific skill, that would be step one before working on a startup, because if you're not safe and you don't have food and shelter, we gotta go with Maslow's hierarchy of needs here and get you shelter and get you food and get you a computer, et cetera. I mean, maybe he's using the library, but what I love about this is, you know, the gratitude and the chutzpah and the resolve of this individual. He's homeless. He doesn't have just one startup idea. He's got two. And he's ready to raise funding and I guess he's watching This Week in Startups. Probably got a mobile phone or something. Not sure how he's making money.

• 33:38Speaker 00

  Let's go with find a skill, something you can do that somebody will pay for. Go online, figure out a way to make 20, 30, 40, 50 bucks an hour. Drive an Uber, drive a DoorDash, whatever it is. Let's get you stable, safe and fed, clothed, et cetera. Get you off the street, get you safe, get a career going, six, 12, 18 months working. Build up a little savings, maybe you get to $5,000 or $10,000. You got a little bit of cash in the bank. Keep your expenses incredibly low. I'm taking this dead serious.

• 34:12Speaker 01

  No, I think it's, I think it's a serious question. I.

• 34:15Speaker 00

  I mean, I'm taking the person at good faith that this is like not a put on or something. Maybe I'm getting punked, but I think this would not be a good. Safety, security, skill. You can get a job DoorDashing. I know it's like hard and arduous work, you know, but you can make 20, 30 bucks an hour if you hustle. And let's get you safe and secure. Whoever this person's family is, if he has family, you know, some people don't actually have a lot of family, et cetera. They're kind of alone in the world. People get estranged from their families, yada, yada. But let's get this young gentleman a job, safe. There'll be time for startups. Once you're safe and secure in your own place, you rent a room somewhere. Yeah, I wish him the best of luck.

• 34:58Speaker 01

  That was my thought too. I think the answer to his direct question is how likely is it that I'm going to get funded? Not, not very likely, just, and not because of anything personal, just because it's very hard to get funded for your first startup. It's a moonshot. I would say, yeah, exactly what you said. The smart thing would be get a, get a job, get a small apartment, get off the street and then start building the future and coming up with the big ideas. I think that's the correct order of process here.

• 35:27Speaker 00

  I, I think this person really has a chance to succeed. I just want to put it out there. I think if you have the chutzpah, when you're down on your luck like this, to be thinking, hey, man, I'm just going to be able to start a company. Like that's a level of audacity that is super inspiring. I don't know how this person is down on their luck and homeless, but I'm not making any judgments here. I'm rooting for the person and there is this thing called the Pygmalion effect. Remember the, what was it? Pygmalion was a book or a play and then it became a movie?

• 36:00Speaker 01

  George Bernard Shaw, the famous play. Most people know about My Fair Lady is the very famous version that was rewritten based off of Pygmalion. Same story.

• 36:10Speaker 00

  And there's like a con, there's a condescending version of Pygmalion. Oh, I'm some rich affluent person. I'm going to take this person off the streets. I'm gonna, you know, do, you know, whatever. But the Pygmalion effect was more of a psychological effect. They did a study on self fulfilling prophecy. I remember this when I was at Fordham doing, it was a psychology undergraduate. The Pygmalion effect in this context, not the movie or play, but inspired by it, is the expectation of the person can determine their own belief in themselves. Let that sink in for a moment. So if society expects this person to succeed and maybe people in the industry expect them to succeed, hey, maybe they will.

• 36:55Speaker 00

  Maybe they'll say, you know what? If people think I can do this, well, F yeah, maybe I can. I say, I think you can do it. It's never been easier to be a startup founder, but let's also be realistic. I'm very concerned about the safety on the street of, you know, individuals who are homeless in the circumstance under which he got to be homeless. Could be no fault of his own, could be his own fault, could be anything in between. So I'm rooting for this person. And I hope that this feedback gives them some hope and continues for them to drive. Don't worry about venture capitalists right now. They're not going to fund you if you're homeless. You may get like a condescending thing here where somebody's like, oh, I would like to be the angel investor or seed investor

• 37:38Speaker 00

  who took them from homeless to a, you know, Y combinator to a billionaire. I don't want to get into that because I think that's condescending and not realistic, Lon. A person who is on the street, the number one thing is safety, a job and food and clothing and healthcare.

• 37:54Speaker 01

  Go get, go get the Walmart job. Do that for a year. Get yourself a little place. Get yourself stable off the street. That's when you start thinking about, oh, okay, now it's time for me to start getting my startup together. I couldn't agree more. But the attitude is what impressed me, that this is a homeless person. They're not asking for a handout. It's not self pitying. They're not giving us a woe is me story. He goes right into like, and I've got two startup ideas. I need people to hear.

• 38:20Speaker 00

  Two, not one, two.

• 38:21Speaker 01

  It's the, the speed at which we go from, hey, I'm living on the street. By the way, here's my companies. I was impressed.

• 38:27Speaker 00

  Well, let me ask you this. When you were at the homeless shelter around the corner from the offices, did you run into this individual?

• 38:33Speaker 01

  I did not.

• 38:33Speaker 00

  Identified you as homeless.

• 38:35Speaker 01

  I did not. And that has not happened.

• 38:37Speaker 00

  The greatest story ever.

• 38:38Speaker 01

  Over a year.

• 38:38Speaker 00

  This guy looks like he could be a startup founder and Lon was walking to his car. He's got a nice car. I pay him a decent salary here. He's got a decent car, going to his nice house, got a house now. Dog, he's doing great. He walks by the homeless shelter. Yeah.

• 38:54Speaker 01

  Guy says, well, there's a line because in the morning.

• 38:57Speaker 00

  Come on in. We can help you any way you want. He's going, you went full hobo style. That's why I suited you up.

• 39:02Speaker 01

  He was making a place for me in line. He's like, hey, come, you could come sit right here. I'm like, actually I'm on my way to my job. Thank you very much. That's.

• 39:07Speaker 00

  Actually, I am not a hobo.

• 39:10Speaker 01

  It's a little bit of a wake up call, folks, when, when the home, but you got to admire my, my, my love of comedy that I immediately came in and told that story. A lot of people would die, take that to their graves. Not me. I couldn't wait to get on camera and tell that story.

• 39:24Speaker 00

  People think Lon, you know, they see Lon on with his custom suit and shirts. He's manicured well. But imagine him if he's wearing like a T-shirt from the eighties he's had for 30 years and he's wearing a pair of stained jeans. That you could make this mistake. He could be hobo. I call it when Lon's in hobo style or when he's in, what was in the, who's the guy in Homeland with the big beard like you?

• 39:47Speaker 01

  Mandy Patinkin, Mandy Patinkin.

• 39:49Speaker 00

  Yeah. When you're in your Mandy, your best look is Mandy Patinkin. You put hobo style beard.

• 39:55Speaker 01

  He's got the big beard, but yeah, he slicks the hair back, Mandy Patinkin.

• 39:58Speaker 00

  That's what I told you to do. You have to Mandy Patinkin this. You've got to get a little hair gel going because the beard with the hair gel and the suit, you look exactly like Mandy Patinkin. And he's got good looking back. Here it is.

• 40:09Speaker 01

  From Homeland.

• 40:10Speaker 00

  Look at this. I need to get a picture of Lon and him side by side and look.

• 40:13Speaker 01

  He could be my dad. He looks a lot like.

• 40:15Speaker 00

  He's on the GLP.

• 40:16Speaker 01

  Yeah, he looks a lot.

• 40:17Speaker 00

  And he's on the GLP one. Look how skinny he is.

• 40:19Speaker 01

  Of course he is. Yeah. Look at that.

• 40:20Speaker 00

  That looks like you. That, we should get you a pair of readers and see.

• 40:24Speaker 01

  I'll bring in a picture of Lee Harris, my dad. That, that it's, it's a very strong likeness. He could definitely be my father, Mandy Patinkin.

• 40:31Speaker 00

  I think it's a good look for you with the slick back. See, there is a slick back here. Look at him in the tie. I'm putting you in a tie on the show next week. I'm going to have a tie week for you. I want to see, I'll, I'll put my tie on too. All right. Let's, uh, thank you for the question. Okay. Great job, everybody.