This Week in Startups - Jason’s Put a $5K Bounty on His Dream Chrome Extension | E2338

Episode Date: September 28, 2026

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  

All right, it's time, long, 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. Right. Because I had been hit with a lot of copyright issues. And because we were doing blogs and gadget or auto blog, joystick, well, these are great blogs.

Shout out to Peter Rojas and Ryan and Sean Gold and, 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, 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. I 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. 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.

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. Now, if you could,

long, 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, caveat, ship it, win, 5K. Tell us what we got. 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.

slash 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. northwestredisteredagent.com slash twist domain. Every. For all of your incorporation, banking, payroll, benefits, accounting, taxes, or other back office administration needs. Visit every.io. All right. So we've got three entries to go through today. Well, hard to do. 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. Dot 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 Roberts 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. Okay, so this is annotated. Dot WTF.

We'll call this submission one. Submission one. Officially submission one. Let's take a look here at what they built. And you can sportscast it. 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. 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 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. And now the demo is even progressing. And we can see you could also edit a. So it created a page at annotated.wtf for the handle at TWI startups.com slash. And then a slug on dash six dash flags, roller carcarsie, yada. And here they said the annotation is at the top.

I cannot believe people are still getting injured by roller carcars. how is this still a thing 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 on. And he's highlighted, and he has the marker there annotated at 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, yada. Very well constructed, easy to use. I would have put a screenshot of the web page 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. I actually feel like it's a generational thing. Our era, the idea of taking a piece of someone else's video and then re-sharing it was like, oh, I don't know. be a little uncomfortable, you should just link back to them.

But today, clipping has become such an art form undo 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 original content. I think that's okay. 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 Anitated. 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. Sure. I would also note you, there is a file, a claim button at the bottom if you feel like somebody has clipped too much of your original. original work and you're a little salty about it. Okay. So yeah, take a look. We're in the sidebar. Let's get it playing again. And you can see that they're now leaving a comment.

I thought Punez 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 Punez demo is 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, your digs, your FARC.coms, your Reddit's, 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. Yes. Very nicely done. And I saw, if we scroll back a little bit, he did give the starting time and the 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. 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. Okay. Yeah, wow, this is great. Yeah. He did a really nice job. This one is pretty slick. So now we're on, we're on, we're on X.com, the everything app. This is a post from Jason and with a chart.

And again, we're doing the same thing. They're going to add their comment. What's your take on the tweet? More men need to lock TF in. FN. 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 can 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. Starting a company is hard enough. You need to focus on running your business and building a great product.

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every will help you hire contractors in over 200 countries. Plus, you're going to get 3% cash back on every dollar when you use your every corporate card. So head over to every.0.io and stop wasting time on stuff that isn't growing your company. That's eV-E-E-R-Y.I-O, Every.I-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, one point O

out. And now it takes but two weeks or less. Well done. 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.

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. Oh, interesting. You're right. I think that's an image. Or it might, maybe they're just embedding the image.

Are you on the live site right now? This is a pre-recorded demo that you're seeing. No, no, I think he moved to the live site. Oh, well, there you are. Okay, so your producer Jacobs on a 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 your life.

What I would do here, I'm just going to 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. Well, the screenshot idea, because so many things get pulled off of Twitter, deleted, people think better of it. That's why a screenshot would be a savvy move there, because then you can. Correct. And I think it would be your way of preserving a hot tweet that you think might get pulled. All right.

Yeah. I'm going to give this one on a score, eight and a half out of ten. It's very strong. 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 Accounting using it. My Lord, this is fantastic.

I want to give it an 8.5 of 10. Let's go to our next demo. All right. Our next demo comes to us from Alan Schiflett, number two. Okay. It's another take. There he is. There's Alan.

It's another take on annotated. Beautiful landing page. And as you can see, he also, I was going to 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 going to, we're going to log in here. We're going to, it's a CNN page about Dolly Paul. Poor Dolly Part.

It's about 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. Yes. So then we're moving down here. And they write a snarky crime.

I guess I'm too young to know who this is. And we get to the article page, like the permalink page. I said, okay. Go ahead a little fast. Decent. Let's go back here to the... To this page. Well, no, go back one.

This is the feed page of all of them. the permitting 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 on the right and the follower

account and all that great stuff. The left, I would have put an actual screenshot of the CNN page or like a thumbnail of it or something. 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 What's going on? Yeah, it looks like this page is just a link to this CNN article and then a comment thread underneath it, whereas. So work to be doing. 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. So this is submission two. Let's go ahead and see what's next. This is you talking about the mosquito laser iron dome for mosquitoes to protect your backyard. And then leaving a comic need one of these. But for Hornets, please.

Jacob's having some hornet troubles, I guess. So he got it. Okay. So here we know. Taking and annotating a tweet. 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 can 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. one for that. Here's the kind of annotation that I'm leaving. That's a nice feature. Yeah, plus one for that. All right. You can keep going. The page is a little bit clugie on the left, and there's your main feed. What is? I like the idea of a main feed, but yeah, it needs to be better. What is that 21 in parentheses before your at name? I don't even know what that is. I think they're just pulling the tweet,

like metadata and some stuff's getting pulled in. Okay, yeah. That does not look great. That looks a little weird. Hey, listen, this is like a V-1, 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. 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.

I also, if you look at the very top left, the plans for a for you algorithmic feed, like annotated would 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. Fantastic. Well done. Do we have our third submission here, annotated.com,

with just one end to set it apart. It's by Chirag, Azarpota. He bought the domain. He actually bought this domain, Jason, annotated with one end, in case people misspell it and still want to access the site. Great. Hijacked my traffic. There he goes. So, yeah, you've got a competitor.

You're learning something. 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. 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. So if you get Italy or you get Japan, look it up. You've got to pay for the maintenance of the embassy and the staff and the food and everything. So it costs you $5 or $10 million at a pocket, at a pocket or to your partners or whatever. It's not a, there's nothing free.

That's a crazy system. I would assume the government is a good. Anyway, so back to Anitaine. We could talk about that all day. I'm fascinated. But the building, maintenance, security, and salaries are taking care of 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 on for like when they have state dinners or whatever. And 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's prompts signing in to the annotated.com service. That's something do we haven't seen on any of the

others. And then here we go. Here's how the annotated page is like kind of a kind of an X.com Twitter formulation on this one. Looks good. It does. 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 do. There's many services that will do that. And then you can have a little more about the story there. But otherwise great.

And it has the date and the time and everything. You have trending sources on the right. Yeah, I like that. Home Explorer profile saved. I mean, and you can join the conversations. 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

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Registered Agent is the best way to establish your new company. Learn more at Northwest Registeredagent.com slash twist domain. The problem here along 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, this article has the third paragraph. There's a really important point to be made that the ambassadors, let's say, have to pay for the parties. You highlight that portion and then you say, I didn't know that ambassador's really interesting concept here going on. So whoever made the demo is great that you made a smoothest demo.

It shows everything. But you got to remember my rule of startup founders presenting a product. Examples matter. Examples matter. Examples matter. Yeah. Like that Dwar Keshe 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 black. platforms like this. Yes. Like that would be a better one to do. We're going to do a video one. So they picked this week in Startups episode. This is a recent VC roundtable.

That's Shield Minote. Okay. Oh, you mark the part you want in the actual. Yeah, you put in the, you put the timestamp in yourself. Yeah. It's all this one. I remember this now.

This one, it's a lit, this is one of the more clusy ones I was talking about where that other one, the original when we looked at WTF, it's very neat. It's like this little app and you just drag and drag. It is like using, quick time or something. It's very intuitive. This one's less so you got to really exactly

find the time code you want. It's a little, it's two extra steps. Correct. Okay. Good enough, though. Let's see what happens when you actually hit continue. When you actually do it, what happens? And that's when you type in your reaction. Shield is, oh, I missed it. Something about shield. Yeah, note is live. And you notice like when the notes live, you have to go view the note, it should just take you to view you. This is like a little UX thing. Why are we making the person do another click? It should say your notes 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. If you, if we were like,

hey, they stole our episode of, oh, there we go. J. Shield is an absolute God on X. Great. Awesome. All right. So the first one's like an eight and a half. The second one's like a and eight and this one's like a six just in terms of refinement design etc 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 around two. It 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. But that's where my kind of gut is right now. Lon, what did you think? Do you have a ranking here? Oh, I absolutely agree. The number one, WTF Roberts 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. 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 Robert. Well, now here's the next thing. I would like you to, to maybe 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 can actually build this as a startup, start using it. And venture capital firms in their documents can incubate a company.

you can actually form a company. And, like, Sacks did that with his, was it glue, his AI-based version of SACC. You know, so you can put a couple of million bucks in a $300 million fund, let's say, towards an internally baked 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 think this could be a public service. That's one possibility. 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. I love him to annotate this story. So it's my story, right? I wrote a blog book. I would love to get law 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 1 that's doing data for LLMs. 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 in a micro one to resell or to any of the data ones or you just make it a public service.

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 Funzies. Mm-hmm. Correct. All right.

Well, this has been an amazing round one. Round one is now complete for Annotated.com. And we will go to round two, 15 days, two weeks, basically, after this air. So whatever day this airs, two weeks from then, the next episode of this week in Starves, we'll have this. So if we do this on one Monday, it'll probably be two weeks and then a Wednesday. Something to that effect. So mid to late September. And listen, we did this once before.

We did. And we gave the money. So what was the first project? It was live commentary. Live commentary. AI providing live commentary on a podcast. And we had personas. Like there would be like the Joker.

There would be back check. I mean, it were proof of concepts, but it wasn't like this project. The result of the first bounty was a lot of proof of confidence. which are good, a lot of good ideas, but not a shipped product. What I like about this time is we've now upped at 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. This week in startups.com slash

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, are subject to change, and it's J-Cow's money, so yada, yada, yeah. We decide how we want to do it. It's the worst nightmare of every founder. You've built a product. Everything's working great. Then real users start flooding in, and suddenly it all breaks.

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So they know your uncle JCal sent to. I got time for an ass. You want to do some ass, 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. Well, come on, man. You guys putting me on here or something? I mean. Oh, okay, okay. I try to be right context here.

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. And they're ready to make some money, but the only thing. is on free 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 and how could I overcome them and what is it that investors are looking for whenever investing in to start a guy a founder with two startup companies that are both for revenue.

And what are the odds of both for them being funded? Okay. All right. Well, that's something I was not expecting. I thought you were doing a joke or a bit or something. 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. 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 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've got to go with Maslow's hire your needs here and get you shelter

and get you food and get your 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 I did. 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. 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 door dash, whatever it is. Let's get you stable, safe, and fed, cloth, 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 or $10,000. You got a little bit of cash in the bank. Keep your expenses incredibly low. I'm taking this dead serious here. No, I think it's a serious question. 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 point. security skill. You can get a job door dashing. 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. your own place, you rent a room somewhere. Yeah. I wish him the best of look.

That was my thought, too. I think the answer to his direct question is, how likely is it, am I, 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. 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. 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? Pigmalion was a book or a play, and then it became a movie. I don't know the order. 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. 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 going to, 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, as a psychology

undergraduate. The Pygmalian effect, in this context, not the movie or a 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. 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 were homeless in the circumstance under which he got to be homeless. Could be no fault of his home. Could be his own fault. Could be anything in between. Yeah. I'm rooting for this person.

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 is like, oh, I would like to be the angel investor or seed investor 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 long. Yeah.

A person who is on the street, the number one thing is safety, a job. and food and clothing and health care. 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-as-me story. He goes right in to like, and I've got two startup ideas.

I need people to hear that. Two, not one. It's like it's the speed at which we go from, hey, I'm living on the street. By the way, here's my companies. I was impressed. 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? I did not.

Identified you as homeless. I did not. And that has not happened. The greatest story ever. 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 me a decent salary here.

He's got a decent car. Going to his nice house. Got a house. knows him. Oh, he's doing great. He walks by the homeless shelter. Yeah. Guy says, well, there's a line because in the morning.

Come on in. We can help you any way you want. He's going, you went full hobo style. He made a place for you up. He was making a place for me in lines. Like, hey, you could come sit right here. I'm like, actually, I'm on my way to my job. Thank you very much.

That's okay. I am not a hobo. It's a little bit of a wake-up call, folks, when the home, but you got to arrive my, my love of comedy that I immediately came in 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 him. People think Lon, you know, they see lawn on with his custom suit and shirts. He's manicured well. But imagine him if he's wearing like a t-shirt from the 80s. He's had for 30 years and he's wearing a pair of stained jeans.

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? But Tinkin, Mandy Patinkin. When you're in your mani, your best look is Mandy Patinkin. You put hobo style, beard, crazy hair. He slicks the hair back, Mandy Patink. That's what I told you to do. You have to Mandy Patank of this.

You've got to get a little hair gel going because the beard with the hair gel in the suit. You look exactly like Mandy Patink. And he's got good looking guy. There it is. There is from Homeland. Look at this. I need to get a picture of Lon and him side by side. And look.

He could be my dad. He looks a lot like like. He looks a lot like like. He looks a lot like like. And he's on the GLP 1. Of course. Of course he is. Yeah, look at that.

That looks like you. We should get you a pair of readers and see how... I'll bring it a picture of Lee Harris, my dad. It's a very strong likeness. He could definitely be my father, man. I think it's a good look for you. But the slick back... See, there is a slick back here.

Look at him in the tie. I'm putting you in a tie in the show next week. I'm going to have a tie week for you. I want to see... I'll put my tie on two. All right. Let's thank you for the question. Okay, great job, everybody.