This Week in Startups - Why New Yorkers hate AI Friends, Producer Claude gets an update, and the value of human writers in the Age of Slop | E2185

Episode Date: September 29, 2025

Today’s show:Friend’s new AI pendant just wants to be your new pal. So why do New Yorkers hate them?On a brand-new TWiST, Jason and Alex consider the Friend AI pendant, which listens to everything you say all day and then sends you snarky texts about it.WIRED says it’s unhelpful and will make your friends hate you. New Yorkers are so sick of their aggressive subway ads, they’re tagging them with graffiti. But what do Jason and Alex think of the wearable companion?PLUS the value of bringing your last team with you to your new project… why partnerships often lead to purchases… Producer Claude got an upgrade… two fresh TWiST 500 companies… the rise and fall and further fall of Tai Lopez… AND Jason explains the rules of private jets.Timestamps:(0:00) Jason congratulations the Eagles while wondering what’s going on with Philly fans(03:23) New Yorkers are not in love with these Friend AI pendants and their subway ads(10:08) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(11:28) Show Continues…(13:49) Are people actually using AI agents? Is it still too early?(17:01) Startup Lesson: The value of bringing your last team with you(19:27) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(20:43) Anthropic released the new Claude… can they catch back up with Grok?(27:13) Why Circle’s community app is blowing up all of the sudden(29:23) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit https://www.aws.amazon.com/startups/credits(30:48) How startups SHOULD measure growth and profitability. And why you need to show your work.(36:42) Why human writers are about to be MORE valuable in the age of AI Slop.(42:20) TWO new startups are joining the TWiST 500… Jason’s thoughts on Phia and Huxe(46:23) Influencer and bookshelf haver Tai Lopez is under investigation by the SEC! A look back at a viral superstar…(54:11) Jason explains the rules of flying in private jetsSubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcpFollow Lon:X: https://x.com/lonsFollow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisThank you to our partners:Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWISTLemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twistAWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit https://www.aws.amazon.com/startups/creditsGreat TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarlandCheck out Jason’s suite of newsletters: https://substack.com/@calacanisFollow TWiST:Twitter: https://twitter.com/TWiStartupsYouTube: https://www.youtube.com/thisweekinInstagram: https://www.instagram.com/thisweekinstartupsTikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: https://twistartups.substack.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

If you're a founder, this is the important lesson, if you raised venture capital before and your team, your team is made up of the people who raised venture capital and failed before, you're like level one in terms of fundable. Then if you had an exit and you returned your, you know, if you returned people's money back, plus a little bit, you're like level two. If you had a great returning, you returned a lot of their money back. They had a great exit. Now you're like level three. And if you IPOed or you had like a billion dollar sale now you're like level four so if you just like look at those levels of founders level zero is you're just new to the game okay go to y combinator launch accelerator antler tech stars etc but once you've raised venture capital before now you can go to venture capital

and say hey remember when i lost four million dollars trying to do this crazy pendant company and it didn't work well now i've got a better idea and here's what i learned from my pendant company and, you know, just putting the first two stories together. That actually makes you more, more fundable. This Week in Startups is brought to you by AWS Activate. AWS Activate helps startups bring their ideas to life. As you build and scale your business, activate credits grow with you to support your changing needs.

Apply to AWS Activate today and receive up to $100,000 in credits. Visit aWS.amazon.com slash startups slash credits. Lemon.io. Hire pre-vetted remote developers and get 15% off your first four weeks of developer time at lemon.io slash twist. And Squarespace. Turn your idea into a beautiful website. Go to Squarespace.com slash twist for a free trial. When you're ready to launch, use offer code twist to save 10% off your first purchase.

of a website or domain. All right, everybody, welcome back to this week in startups. It's Monday. It is September 29th. The summer is over, folks, and soon it will be snowing, and you will be getting Halloween costumes, Thanksgiving dinner, and putting up Christmas ornaments. Oh, my God, how did this happen?

I just, it's like the starters pistol. The only good news for me when the fall comes. You know what that is? What's that, Jason? My Knicks. My Knicks are playing in UAE. And I got invited by many people in the UAE to sit courtside because I'm a micro celebrity, as you know.

My select, I'm a micro celebrity, a mini-celeb. And so people invite me to sit courtside if they can't get an actual celeb. So they, you know, they'll start with Timothy Chalameh and go to Ben Stiller and, you know, maybe Ben Stiller Timothy. I don't know, whatever your bag is, maybe a Kardashian. And then they'll go down and eventually they'll. invite me when they when they when they before they sell their tickets I'm like the last before they put them on stop. Got it. Uh, but yeah, the Knicks are playing in UAE. So Thursday and Saturday I get

to watch them in the morning and I am so excited for my Knicks this season. Uh, but you're doing really well. Your Eagles are four and no. That's great. Absolutely. We're, we're stoked. Now, the context for here, Jason, is that you have some views about Eagles fans that I think you should put on the record and tell everyone in Philadelphia, the founders, the richer capitalist, what you think of them? Oh, it's not like I have like a polarizing view. I don't want to create a Palmer Lucky-like situation, but they're terrible. They're horrible.

Worst fans in sports. I mean, they burn things down. They defecate. They urinate. I mean, was this the group that ate oats out of horse dung, I think, when they won? That would not surprise me. But what matters more? Literally, like, a guy got on his knees and was like, I'm going to eat that oat out of this

horse dung on the street. And then, like, they're climbing up. They're in tidy, witty underwear is on the top of lamppost poles. If these guys go 10 and 0 or something crazy, 7 and 0, I mean, Philly, they're going to just, I mean, they're going to have to send in the National Guard, which I think, you know, Trump's on a 10 city national guard door anyway. So just skip Chicago and go straight to Philly. But congratulations to them. That's pretty, that's pretty hard to do to start the season of four. It is pretty hard to do.

And what's even more important, any Eagles fan will understand this, but the Cowboys, the Dallas Cowboys. The team that claims to be America's football team is currently one, two, and one. So ha, ha, ha, cowboys. All right, listen, we got a lot to get to. And friend.com. I saw that had a lot of main character, energy. People are losing their minds over friend.com. Tell us a bit about this.

All right, so Friend is an AI pendant, one of the startups that was founded in the wake of the launch of ChatGPT, when people really wanted to bring the LLM closer to their lived experiences, their life, Jason. Uh, friend.com is a $129 pendant and basically it's a digital companion. Think of it as something that sends you text messages and kind of is your friend throughout the day. And they're back in the news because they put together an enormous campaign in the New York subway. Here's a picture of it. Here is the CEO Avi Schiffman describing this as the largest NYC subway campaign ever. And the, if you can't, if you're on the audio version, it has signs like, I'll never bail on your dinner plans.

Friend.com. And just is, if you don't have enough friends, you can get this pendant and then it'll be your friend. Now, not everyone was convinced. Here's an image of someone who graffitied on the ad writing surveillance capitalism, get real friends, which is a pretty big dis. But I think also, you know, if you're this company, no publicity is bad publicity. But Jason, I think that our view, or at least my view, is that we don't need to AIify everything. So to me, this seems a little bit outside of my box, but I'm curious if you have a different take. I mean, I have been super critical about persistent recording because, listen, I'm a Gen Xer.

I think, you know, I actually care about privacy and the surveillance state, and I have enough scar tissue to know that anything that, and just firsthand experience, anything that can be hacked is going to be hacked. That's just how it is, folks. And so you learn this over, typically you learn this the hard way, you know, something gets hacked, you know, whatever, your bank account, your email, something. And your group chat. and that's what will happen with these. Somebody will hack it, not necessarily friend.com, but all of these.

And you will be having a spicy conversation or you'll be in a therapy session or you'll be drunk with your friends and you'll summarize your friend in their worst moment in time. And I can tell you, you know, whatever your friend's worst drunk moment in time is, like probably not meant to be broadcast to the world.

So I do have issues with this technology, but I also am smart enough. and experienced enough to know that this is an inevitability. People are going to embrace these. There's going to need to be some regulation. I told the story here. I was at a dinner with a friend of mine, and he had one of these note-taking pendants.

And like, I don't know, a couple of minutes into the dinner, I see like a glowing white LED, not like glowing in a major way, in a minor way. And I was like, what's that? And he said, oh, it's my AI pendant. And I said, oh. And he said, is that a problem? and I said, I mean, only if you want to remain friends.

Like, you're recording six people at a dinner? Like, what? And he took it off. But he showed me, and it was, for the first five minutes, it was a perfect transcript. Like I was- Wow, that's insane. In a restaurant.

No. So I just want to encourage everybody to understand. You're being recorded and transcribed already. It's already happening. So that doesn't mean we should do more of this. What's interesting about this story is the amount of hate for this founder, who I believe is brilliant. Friend.com, I think he spent like $18 million on that domain.

I'm not sure if that number is correct, but I saw that go by in my feed. And friend.com is, you know, that's a domain worth a couple of million. 18 million is certainly overpaying for it by a factor of at least three or four X. It should be no more than $5 million for that domain. But okay, when I was at AOL, we bought Games.com. and the guy wanted $10 million for it and had a conversation with the leadership

and I was like the domain guy there so they were like, do you think we should do it? I said, give me the rough profile of our games business. They explained the games business to us and I said, yeah, pull the trigger on that, 10 million. If worst case scenario is we can resell it for $5 million if this isn't a priority anymore and we'll have lost $5 million,

but we've already got tens of millions of dollars in profit from this business. Why not have... Yeah. Jason, it was, according to producer Oliver, it was $1.8 million for Friend.com, not 18 million. So they didn't overpay.

They actually may have gotten it for relative steel. That's actually cheap. That's cheap. And that is, this company has raised, how much? A 2.5 million that we know of. So a pretty material chunk of that went to that domain. But if you sell a device for a... Wait a second.

If they did the largest ad campaign in the subway, that had to be millions of dollars. So we need to figure out how much that... They must have raised since then. We need to, as producer clawed, to get involved here. because they must have much more money raised. They raised a $2.5 million round in July of 24, and then another $5.4 million led by Pace Capital in December of that year. So we're talking about the first round.

So a total Jason of $7.9 million, which actually, now that I say, I think, say that out loud, $1.8 million for the domain, a million for the subway ads, and they have a harder device shipping theoretically later this year. That's pretty efficient overall. I mean, here's what I'll say. The people who are like, that should have gone into your problem.

product, et cetera. Okay, you can make that argument. Hey, a million dollars with, you know, I don't know, five more team members, highly paid, 200K all in. Would they make a better product? It might not, it might not be an either or. And what this signals is to a venture capitalist that this person understands branding and is willing to go big. There are far more founders who don't, who are not willing to go big. And VCs are like, well, I have all this money sitting over here. I would like to see you swing for the fences. So if you feel you have product market fit, then go ahead and spend a couple million on marketing if you can afford to do it. But this obviously could be runway. If this startup was spending $2 million a year, you know, and they're burning $150K a month, let's say,

$200K a month, you know, that $2 million could be an extra year or so of runway, in which case you would be like, hmm, but this person's playing to win. And putting aside the product, I do think there is a market for these. And spending this kind of money seems a little bit aggressive, maybe a lot aggressive to people. But here we are. We're talking about it as the number one story. And it's the, I think he has 25 million views on the tweet about the largest New York City subway campaign ever. So let's say the subway campaign got five million views. Then maybe five, 10 million people take the subway every day. Probably saw this. Maybe maybe that means 15 million we'll see it over time.

He's got 25 million views on the tweet about it. If you want your business to succeed online, it has to stand out, and that's why you need a beautiful, world-class website. The good news is you don't have to hire an expensive designer anymore, nor do you need a bunch of developers. No, Squarespace has all the tools you need to claim your domain and start building your company. Hey, maybe you've got a product to sell. Maybe you want to show off some samples of your work.

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Go to Squarespace.com slash twist to get 10% off your first website or domain purchased. That's Squarespace.com slash twist. It used to be you did things IR to get viral buzz on social. now, I think it feels like the viral element of it's more important than the actual thing you're doing. Jason, a couple of things. First of all, according to the friend.com website on the privacy point, where are your memories stored that it records? They say that they're encrypted by your friend's circuit board. And if you lose your pendant, they're inaccessible forever.

So it's on device. Now, that doesn't solve the recording your friend's point. It does at least, though, mean that hopefully you're not going to have all of your memories leaked. I mean, they're using an industry standard, you know, concept in terms of keys. You know, you lose your key, you lose your data. You lose your keys. You lose your coin like in crypto. So I get that.

I'm sure there's an export feature where you could set it up that every year or every couple of months or whatever your bag is that you back up your data and export it and email it to yourself. So I think that there will be a market for these. I predict that the product being made by Johnny Ivan, Sam Waltman will be exactly like this, some sort of a puck or device that you has a long battery life, that has a 5G connection and Wi-Fi, obviously, that has a couple of really slick design buttons on it that you can take out, ask question to, it has great speakers so it can play music. But here's the thing that blows on mind about this. They have only sent out and activated nearly a thousand of these friend pendants so far.

So I know they've sold more than that, but with D30 retention, so 38 retention of 25% and only a thousand shifts. Was this leaked or did he publicly talk about it? Publicly talked about it. This is, Jason, this is pulling from a note to his investors that he put on X. Here it is. As of July 30th, since July 30th, 464 friends have been activated. Now it's closer to 1,000 according to him. D30 retention 25% and over 125,000 messages have been sent.

It's a small sample size we're going to have to see. But they certainly have enough attention that if they can't convert this level of buzz and hype into a functional user base, I don't know what their plan is. But moving on. Paid.a.I raised a $21 million seed round. and this comes after the company raised a 10 million euro pre-seed round in March. TechWrench reports the company is now worth over $100 million. Now, I'llx company for two reasons. One, what Paid is doing is interesting in product terms,

but also we just have the CEO, Mani Medina on for a Twist 500 episode. That's episode 2,175 if you want to go back and listen to it. But what Payne's doing is awesome. So everyone out there wants to build AI agents that essentially do stuff for you, that replace humans, that lower your cost of doing. business, but it's really hard to price them because you don't really want to use a traditional SaaS models, Jason, because that's going to ruin your margins because tokens are both variable in demand and not cheap to generate and then deliver. So what paid does is tries to help people

pinpoint their costs and then price on a per value delivered basis and therefore allow the agentic economy, if you'll forgive me the phrase, to actually be a profitable business for startups that want to deploy these to end customers. I think it's a cool space. And I think it's really cool that they just raised a bunch of money right after we talked to them. Yeah, I wonder who is actually using this because I don't know of any AI agents right now out there in the field. I've yet to see somebody like, say, talk to my AI agent, with the exception of maybe customer support. But it feels like something along the lines of Stripe where you're going to be billing people based on consumption. So it feels like rails and infrastructure.

So the bet you're making here on what really is not a seed in a series A. This is a series A and a series B in terms of numbers. You're betting that there are going to be a billion agents out there charging for their money or a trillion of them and that some number of them are going to need rails. And I guess that was sort of like Stripe's pitch. We people need to do commerce on their websites. and you can drop in this JavaScript and we'll manage it all for them. So it makes sense.

And I wonder if they have early revenue to backup this. Did they talk about their customers at all or is this all in the clouds? Well, during my interview with Manny, so he said that they quote, broke code in January, February this year. So it's a very young company. I know. I love that phrasing. Started out with the pilot customer.

The nav close to 20 of those. and they, quote, just landed their first enterprise customer last week, now a couple of weeks ago. But yeah, so they appear to have an actual real customer and maybe two dozen pilot customers. So very nascent. But Nanny Medina was able to raise this amount of money at such a high valuation because he was one of the co-founders over at Outreach. And he was their CEO for a long time. That makes sense. Yeah, and that company was worth $4.4 billion back in 2021.

Paid.A.I. I think it's a cool company. If agents are going to become big, they'll become big. If agents flop, they will too. But I love a binary bet in startup land. Yeah. I mean, when you see a $100 million valuation and $30 million raised with one customer, that can be frustrating for founders who have a million in ARR and they can't raise a Series A,

right? And so when you see that, always double click and see if this is a successful founder with an exit. If you're a founder, this is the important lesson. if you raised venture capital before and your team your team is made up of the people who raised venture capital and failed before you're like level one in terms of fundable then if you had an exit and you returned your you know if you return people's money back plus a little bit you're like level two if you had a great returning you returned a lot of their money back they had a great exit now you're like level three and if you IPOed or you had like a billion dollar sale now

you're like level four. So if you just like look at those levels of founders, level zero is you're just new to the game. Okay, go to Y Combinator, launch accelerator, Antler, Techstars, etc. But once you've raised venture capital before, now you can go to venture capitalists and say, hey, remember when I lost $4 million trying to do this crazy pendant company and it didn't work? Well, now I've got a better idea. And here's what I learned from my pendant company. And, you know, just putting the first two stories together. That actually makes you more, more fundable. Because two things.

You've raised venture before, and you're a serial team. Those two, man, people look at that. That's why it's important to bring your last team with you. Get the band back together. Almost all of the great bands you've heard of out there, dire straits or whoever, they probably played in a band or two before. and then one or two of the best members left the band and then went to another band and then they

started a third band and that was the band that actually hit. You just, history forgets those previous bands. But yeah, really interesting story and great job getting that founder on the Twist 500. The Twist500.com is where we're tracking the top 500 private companies. The top 500 private companies and our newsletter, which you can sign up for at this week. Startups.com slash newsletter. I hopefully that's working. And if that's working, you can sign up for our newsletter.

Yep. If you want the newsletter, just go to ticker. Dot thisweekend startups.com. That's where we're talking about the Twist 500 companies because, Jason, they don't get enough coverage. When you're a busy founder, finding a new developer, my God, that can become a full-time job and you've got enough on your plate. I mean, you're running a startup.

But lemon.io has done the hard part for you already. They've got a crop of pre-time. vetted developers that they've ensured are experienced, results-oriented, and prepared to make an impact at your startup. And they can work right now at competitive rates. These are skilled, hand-picked devs with a minimum of three years of on-the-job experience. And just 1% of applicants are accepted into their program. lemon.io isn't just recruiting you the top talent that's out there.

They're helping you integrate them into your team. If anything goes wrong, Lemon will find you a replacement developer, AASAP. And many of our launch founders and founder university companies have staffed up with lemon.io and we always get the best feedback. So go to lemon.com slash twist and find the perfect developer or even a tech team in less than 48 hours. And Twist listeners get 15% off their first four weeks. Stop burning money. Higher developers smarter. Visit lemon.io slash twist. So as we were going to record the show today, Anthropic dropped a new Claude Sonnet 4.5. We actually went ahead and had the model itself explained to us what it does and what it does well

We'll get to that in a second but how meta how metta how metta how well no Jason how anthropic actually in this case I was using meta with the low in case M I know. I know You can't do everything that we're doing without a good paid plan over on Anthropics So if you want to get Claude up to the level that we have it you can get 50% off your first three months of Claude pro if you go to clont A. a.I slash twist that's Claude. A.I slash twist now Now, let's hear what it has to say. Producer Claude says, The big leap is that this is better at writing code.

We all know that Clodd, sorry, Anthropics models have been very popular inside of products like cursor, so not surprised to see another step here. It's also going to do faster debugging. It's better at the hard work of programming, like refactoring your code. And it has what it calls practical workflow improvements. Says, quote, I'm better at working with real world scenarios, messy code basis, incomplete requirements, and legacy code. I can help fill in the gaps and make reasonable architectural decisions based on best

practices while respecting their constraints you're working with. Not surprised to see Anthropic fireback, Jason, after we saw XAI's GROC codeFAST one do so well. Yeah, you know, these teams are working extremely hard. They're in the offices, you know, 9-96. And although these models don't feel like they're tripling or quadrupling, like the functionality, because they're coming out so frequently and they're typically 10, 20, 30% better at specific tasks.

If you're doing two of these a year, three of these a year, it's getting twice as good a year. And I like the fact that they're dropping them more frequently. That seems to me to be a wise decision because you just get to have more swings at the bat in communicating with your customer base and then your team is more dialed in.

So I think Apple was always like twice a year, two big keynotes. I think Airbnb did that. something similar and they copied it since the CEO had a mentor in Johnny Ive, and I think he just decided, let's just roll up four or five features every six months, do a keynote, and it just gives a cadence to the team where you feel like you're accomplishing something by a date. Everybody gets worked up for it. And yeah, it's a great management technique. It's a great company cadence technique. And you can then look back and you can start to not just on a quarterly basis,

by finances or a monthly basis by your P&L. You can look at the product drops over time and see the impact they're having and you can also then measure your team. Hey, you know, is the team picking really good things for each six-month sprint? Or are they picking vanity things? Are they picking what matters?

And here, everybody knows that like code is the big piece and that, you know, and workflows. Those are two major pieces that people are using so you can then give examples to your user base. Hey, coders, here's what you can now do, refactoring, etc. And then, hey, for people who are doing workflow and are using this for their, I don't know, customer support or their sales function,

here are new features you can implement. So it keeps a dialogue alive with your key constituents. And I think that's what's starting to happen here. These companies are starting to get into buckets. Okay, for people doing, You know, X, you know, here's the team working on X. Here's the team working on code. Here's the team working on workflow. Here's the team working on images. Here's. And then that will become personas. Designers, finance people, lawyers, accountants, you know, service people writ large, coders, product managers.

And that means this is all going from very theoretical and open-ended platforms to very verticalized software. That's what we're seeing here is the verticalization as we hit four or five, six versions of this software is more application layer functionality. I think it's great. Yeah, to that point, they also tease a new thing called Imagine with Claude, which is, it seems to be almost like a vibe coding service from them. So going up into the app layer there. But I want to just highlight how quickly things can change, Jason. We talked about the Grock code model when it came out, and I've been keeping tabs on its market share over on open router, which does hundreds of billions of tokens.

So it's big enough to have a market share of material note. But if you take a look at how fast things have changed, this teal right here in this chart is XAI's market share going from very little to 40%, I think, in the latest column. So Anthropic does have real competition on the coding front. I think people are underselling how much of that market XI has taken. So I'm going to be curious to see how much market market share. share Anthropic can get back, at least on OpenRouter, from the Elon Musk AI company,

because they really have done quite well lately. Got to have got to hand it to them. It's pretty darn impressive. Yeah. At this pace, we're going to see developers obviously become 30% more efficient a year, 40%, some astounding number. Then you're going to see people who are vibe coding or adjacent to developers. Maybe they have the ability to do light coding, but they never took the coding.

but they never took the coding job, which is probably 10 times the 50 million developers in the world. I always hear 30 million, 40 million, 50 million developers in the world. I'm going to just start saying 50 million. 50 million developers in the world, I think, will 10x to 500 million? In other words, we're going to go from, if there's 7 or 8 billion people on the planet, what's the number, 7 or 8?

You know, right now it's less than 1% of the planet is a developer. It's going to go to 5%. And 5%, you know, times 7, 8 million people, 350 million developers, 400 million developers. That's going to be a very different world, folks, a very different world. And that doesn't count, you know, having the other 95% be able to vibe code or another 10% be able to vibe code. I'm leaving vibe coding out of that. I'm doing developers as a dedicated career. And the next group of people who are developer adjacent and just haven't had the full.

focus level or the aptitude or the time to just go fully into development. Jason, there's a company out there called Circle. And no, I'm not talking about the stablecoin company. That went public earlier this year. This is Circle.S.O. We use this product. We do. Yes.

For Founder University, we use Circle. So it's a community platform. And it's also really good at putting in your curriculum. So you can have like, here's our curriculum, here's chat rooms. So think of it as a place to bring a community together to function as, you know, like a course. So it's kind of like a course combined with a chat room combined with Slack. Yeah. It's very good.

We like using it. We are considering moving off of it because we just love Discord and we love Notion. And so there's this tension. Do we use a full application like Circle where people have to learn to use it again? or do we use something people already know, like the Notion Discord combination or Notion plus Slack? But Slack charges you for every person. So it's very hard to do free stuff on Slack.

It doesn't give you your whole history. So we think the future is either Circle or Discord Plus Notion. But it is something I've used. I now, I think, for maybe four years, and it's really good. Circle.com. It's a great product. Yeah. Well, it has a lot of competition,

but it's also doing very, very well. So in May of this year, the company said that it reached profitability and was going to reach about 50 million ARR by the end of this year. Critically, it's been essentially bootstrapping. It's been making its own money. It hasn't raised since 2021. And then this September, so just a couple days ago, the company said it's going to blow past the 50 million ARR milestone soon,

on track for its best quarter ever, more fee cash flow every month than it can wisely reinvest, and its rule of 40 score is up to 64. So here's a company that really has found an amazing growth trajectory here. I'm just trying to figure out, Jason, how common is this trajectory? Because they raised money before venture capital, Tiger, et cetera, back in the day. And then they've just been exploding and funding their own growth. It feels very rare.

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and training, plus exclusive discounts with some of our favorite companies and tools. So start getting the support you need at every stage of your startup journey. To learn more, visit AWS. Amazon.com slash startups slash credits. That's right. AWS.com Amazon.com slash startups slash credits. Well, you know, that whole cohort of companies, they had a challenge in that they probably raised money at a very high valuation, right? When the Tigers came in and did a lot of these rounds, and they probably needed time to finish the product, to explain to customers like me, here's the value of this product to then get us to pay for it and to value it. And yeah, sometimes it's better for a founding

team to just keep their head down and work on product market fit than work on raising more money. So they had a million in ARR in 2020 and then it grew 4X in 2021. It doubled in 2022. That's what you hear sometimes, triple, triple, triple, double, double, double, something in that range. and then a 2x run rate in September of 20, 23. So this is a high growth company. High growth in the public markets is like Uber or DoorDash or Coinbase or Robin Hood. 15 to 30 percent year over year is considered high growth. That's a growth company.

Blue chip companies grow 5 or 10 percent, right? As I think generally the accepted growth rate. But yeah, 50 million in ARR, profitable, tons of money laying around. That's awesome. and then you don't have to dilute yourself. So there's many ways to build a great company. It doesn't always have to be just dumping huge amounts of cash into the company and doing unnatural acts. Sometimes the best thing to do is just sit there, talk to your customers, refine the product, iterate on building a great team.

And if you want to understand the rule of 40, it's a SaaS software financial metric. Basically, rule of 40, a company's annual revenue growth rate, which here could be 50. 50%, it could be 100%, plus it's EBTA, it's profitability. So let's say you had a 20% EBTA and you were, I don't know, you grew 40% this year, you'd have a number of 60. They have a number 64. And that's up from 45. So I think the reason this number's coming out, I'm not sure where that number was released

in a press release or in an interview, is because they want to show that they are a great company to buy and then eventually for people to invest in. Ah, okay. So, yeah, the founders have been tweeting through their growth trajectory, which I really appreciate because it gives us such a better insight into how companies are performing. On the rule of 40 points, Jason, I've heard different things for different people about what should count as profitability. Some people like operating cash flow, some people prefer EBTA. Some people claim it really should be gap in that income. Is there a standard in startup land that people should stick to? I think as long as you explain your math, you show your work is the way to do it. Most people will be able to be able to. able to figure it out. Sometimes you have one-time transactions that occur on a balance sheet of a startup that can just distort things. Let's say a founder got bought out. So you use 10 million of your profits that year to buy some early shares and then you retire them. How do you put that in? So you'd probably separate that out. You'd just say, hey, here's the gross profits or here's

what our EBITA would have been, you know, if we hadn't done this office build out or bought out this lease, whatever it is. So you just, the, just the gross profits. growth is the growth. That's easy. So if the growth is 30% great. And then, yeah, you can back of envelope, explain away your profitability. And if you get over 40, man, it's just, it's hard to fake. That's what's nice about that number is it's hard to fake. If you had zero percent profitability, zero percent EBITA, but you were growing 50 percent year over year, people would be like, okay, that's fine with me. Eventually, you know, you could stop marketing or cut some, growth team or cut salaries and run this business for profits. If it's 50% profit margin

business and it's not growing, yeah, that'll come out as well. And probably balance. They probably should have a rule of 40 where there's like a third thing, which is, and neither of these represent more than 75%. Right? So there's some sort of balance between those two. All right. Well, I like that a lot. But do you think companies today that have quite a You can get the rule of 40 in a number of ways because you can have high growth and some lack of profitability. Is there currently a unprofitability percentage point that's too high to explain a way with growth? I'm thinking about early stage companies here that might be burning a lot of cash, but also growing very quickly. So is there an extreme that's too much?

No, that's where you get to your runway. And so if your runway's 36 months and you know, you're losing 10 million a year, nobody cares. Now, if your runway is six months and you're losing, you know, 100K a month, and if you can get that to 50K a month, now you got a year of runway, you know, people are going to have that conversation. So it really has to do with runway and then can you raise more money and can you, how easily can you raise money? Circle could raise money probably easily, depending on what the valuation was when they did

their peak ZERP, if they did a peak ZERP type round, which I'm totally guessing here. But at the day. $195 million, was that round valuation according to Pitchbook? 395. No, $195. Oh, okay. So, yeah, they could easily raise money again. If they're $50 million and they're profitable and they're growing, $50 million in revenue

times $10 or times $8 is $400 million, $500 million, $600 million. You could probably get a good deal. I think ultimately that product and all these SaaS products that aren't at $500 million are going be, you know, either becoming acquirers of other companies or they're going to be acquired. And we're going to see a lot of roll-ups like IAC and Barry Diller famously did. A perfect segue to the next thing we're talking about. Minlo partner, D.D. D.D. Das recently promoted to that role over at Minlo, tweeted out that he's quote, met with dozens of slop as-a-starved startups that are making millions of dollars

using AI to create an endless stream of blogs for their customers to help them with SEO and GEO. They're all growing insanely. fast, and then he adds, the insidification of the internet continues. So I was curious, what companies might fit into that bucket? Jasper does AI generated marketing content, writes Sonic from a YC company, similar thing, profound, have them on the show. They do geo and some AI generated content. The thing is, it seems that everyone agrees with you that this is either gross or, in the eyes of many, temporary, that people are essentially taking advantage of a moment in time to make a lot of money. How do founders... I'm going to go with, yeah,

Okay, what's your question? Yeah. Oh, how do founders tell the difference? Because people are doing well in the sector, but we also don't like it. So I'm trying to just balance out the two. Yeah. So before dunking on any of these companies, it really depends on how much content and with what type of supervision. I think a lot of these companies are probably the white hat companies that are saying,

hey, we're going to help you do this in a better way so that you. don't get dinged with a search penalty by Google or Bing or Duck, Dot, Go. The people who are doing the slop as a service are probably gray and black hat people, or just gray, and they tend to be just shops that you give them some amount of money. They publish all this stuff. Then you wind up getting reported to Google as a slop generator. They see your robots.t. They see your site map, and they're like, okay, this is garbage.

And it is a moment in time where identifying AI content is going to become easier and easier. And once they do that, and you don't have an author, and there's like an authorship tag, and that authorship doesn't go back to a social media account of a known person, you're going to start having problems. Google knows who wrote stories. You know, tech meme, Gabe has done an amazing job of building a database and semantically understanding who is the author of every article, the New York Times, the Washington Post, TechCrunch, all of these publishing companies, Vox, they know how to put the authorship on there.

They know how to put the bio of the person. What's going to happen in the age of AI Slop is those writers are going to become more valuable, those companies that have authorship on them of known people that link to their content, a substack, for example. If Substack does their job, like the New York Times does, or Beehive does theirs, and they don't allow slop on their platform, then they're going to move up. So there's going to be like a slop rating and a known authorship rating that probably exists in some way today on the latter part, which is known authorship. Google knows who the authors are, just like Gabe at TechMeen built that brilliant site where you can now like go see who, not only like who's the author, but

who are the top authors with breaking stories by this category. That date is amazing. I don't know why Google or XAI or somebody doesn't just buy tech meme for $100 million, well, it a day. I mean, not our beloved tech meme. I mean, yeah, that's true. If they bought it, they probably would screw it up. But, you know, that kind of semantic content that he suffered over building that architecture, super valuable today. And so I don't know if D.D. is talking about Jasper and Ritesonic and profound.

But this AI genital marketing content should always be. a starting point that humans then clean up. I would never let anybody produce, you know, AI directly to publish on the web for any of our properties. And if I caught somebody doing it, we did catch some people retroactively doing it, man, that would be like instant firing. And now every company is going to need to have these rules. No AI slop. Do not post AI content. Really, really bad. And we had a story last week, didn't we, about how people feel about work slop? Yeah. So this is becoming a significant issue.

People are now hating droids. They don't like the droids. They don't want them in their bar, like in Star Wars. We don't accept your kind here. That's what's happening is people are going to start fighting for humans. And Spotify is going to have to make a decision. Substack is going to need to make a decision. Everybody's going to need to make a decision.

Do we want to be a slop shop or do we want to say humans only in here? Yeah, I saw on a heavy metal suburb that I, I frequent. There was an AI generated band that people were discussing, and it was the metal core subgenre. And so people were calling it Clanker core, clanker being a meat space slur for our digital friends, I guess. I don't know how to phrase that. But this is becoming an issue across every single place. I just don't think we're ever going to be able to fully replace humans trying to reach out to humans by putting robots in place of humans doing the actual outreach. But for now, Clankers were actually battle droids in Star Wars. So you remember those? Oh, really?

Stupid droids in like attack of the clones that had the weird heads and Jedi would like kill them a hundred at a time. Those were called clankers by Jedi and by, yeah. Were those the ones that had the bubble that went over them in the Jarger movie? Yes. Oh, okay. In the Jarjorn movie, yes. They were. Thank you.

Yeah. Those are clankers, specific type of droid. Oh, well, I didn't realize it was a Star Wars reference. Yes, no, yeah, they should look like a banana. Yeah. Clone troopers hated them, yeah. So, Jason, we have a couple of companies that we might add to the, The Twist 500 today.

The first one's called Fiat. This is known for its founder, Phoebe Gates, has raised money from people like Kleiner Perkins, Chris Jenner and Haley Bieber. It's doing quite well. It's a consumer AI breakout raised $8 million. It's working on helping people find fashion at an attractive price.

Not really my domain, but I think people are going to be interested in it. Yeah, it's a Chrome browser extension. People love shopping. I think it's a good candidate for consideration before we add it to the Twist 500, I would want to see who the contemporary set is. So when we do the Twist 500 process,

we should look for FIA competitors, established ones, and new ones. I think many of the larger LLMs are now incorporating shopping. Specifically, we've got to look at FIA in the context of what Google shopping is doing. That would be very interesting and just compare side by side the results

and ask yourself, hey, is the FIA result a better experience, does it have better content than a Gemini search, which is basically Google shopping? That's the way, you know, a venture capitalist would do their diligence on these kind of products as side-by-side comparison of the results, take out the logos, take out the, you know, the accruciamont of the interface, which still counts, and just say, what did you, what blazer did you tell me to get? If I described, I want a blazer between $5,500 and $1,500 that looks great, and it's classic for when I go to Nantucket,

you know, in the fall for a wedding, boom, and just do those side by side. The second one, Hux, you know, this competes a bit with opening eyes pulse or what I used to do at Inside, like the Inside Daily Brief, we would just do a short summary of news, people liked it.

But what I found was, you know, with news products, we've never had a news app, never had a news app in the United States reach critical mass. You have to ask yourself why that is, And it turns out people consume news in Instagram, TikTok, Twitter slash X, Facebook. Those are the places people go for news.

And it's incredibly hard to build a product that is two, three, four times better than that experience. What you can build is communities in verticals. But I think Hux like what I did at inside with apps or there was, gosh, what were the news apps at the time? Pulse was a news app. There were, Circa was a news app I had invested in. Oh, Circa. Oh, I forgot about Circa. All this really interesting cohort because there was something called Smarter News in Asia.

And Smarter News became really, I think it was Smart News or Smarter News app. Let me take a look here. Smart News, you're right. And Smart News in Asia became something where people just lived on it. It was so popular. But again, in the United States, yeah. One last thing before we move on here, regarding FIA and e-commerce and the large AI model companies and who's going to win.

While we were recording today, so this isn't actually in the docket, OpenAI announced that they're going to put out buy it in chat GPT, instant checkout, and the agentic commerce protocol working with Shopify and I believe Stripe as well. So there's quite a lot of movement in that space. I think they really want to bring e-commerce into chat GPT because that's a way to make a lot of money. But yeah, a space to watch and we'll keep an eye on. And last week we talked about ads coming to chat GPT.

So, you know, Sam Altman watched Web 2.0 to today, you know, worked at and ran Y Combinator for a bit. He understands monetization comes like just three or four different ways. Consumers can pay you for the product. Advertisers can pay for the consumer's product or transactions can pay for the product. And I would be surprised if he wouldn't do all three of. of those in a product at scale like Chat Chippy T is. Yeah.

Next up Jason, we're gonna talk about main character energy and perhaps no one has more of that recently than Ty Lopez. This is a well-known YouTuber who was busted by the SEC because along with his partner, Alex Mare and Maya Birken Road, they ran a Ponzi scheme that involved raising money to buy distressed e-commerce brands and turning them into money pits as far as I can tell. They raised hundreds of millions of dollars and between 2,000,

in 2020, their holding company called REV or REV, cheated. And they got busted by the SEC, and they're in quite a lot of trouble. What's funny about this. This is all allegedly, this is what the SEC alleges. Yes. They ran a Ponzi, just so we're super clear here. I appreciate that, keeping me out of trouble one year at a time. The reason why this is somewhat humorous, even though, of course, fraud's never funny and

financial crimes are bad, is because the man in question, Mr. Lopez, did things like this. Jason, I don't think I can improve on his own words. Check this out. Here in my garage, just bought this new Lamborghini here. It's fun to drive up here in the Hollywood Hills. But you know what I like a lot more than materialistic things? I don't know. Tell me. Knowledge. Yeah, me too. In fact, I'm a lot more proud of these seven new bookshelves that I had to get installed to hold 2,000 new books that I bought. Okay. I don't know how to how to improve on that. That's like a bite size. It's the amuse-boosh of, like, YouTube.

I'm super aware of this because when I was doing my pilot for NBC that never got on air, and then another reality TV group wanted me to do a show, they brought up Ty Lopez in both, no, and one of them, it's come up like two or three times, actually, when, you know, I've talked to CNBC about doing shows, whatever, everybody. And Ty Lopez's name would come up. And they would be like, what do you think of Tom Lopez? And I was like, I'm sorry, who? And they would be like this guy.

And I was like, oh, I think he's selling courses or MLMs, you know, multi-level marketing products. And all of those courses and stuff like that. I was always like, oh, God, I hope I don't ever get perceived as somebody with a course because we have Founder University and Angel University. In both cases, Founder University is free to founders as long as they show up. They can't take the seat and not show up. and then Angel University, I think we charge like 500 bucks and all the proceeds go to charity and we've given 200,000 to charity. Obviously, I don't need to do courses to make money, but it's always a red flag for me when a rich person with Lamborghinis and gosh, 2,000 books and seven bookshelves, you know, needs to make money off poor people with a course.

That's always like a bit of a red flag. So, yeah, and then it was always very weird, like people buying Pier 1 imports or, you know, RadioShack. These logos, because I did remember when RadioShack went up for auction, somebody was like, hey, should we buy this or whatever in one of my group chats? And I was like, what would be the plan? Because RadioShack means something to a small niche audience of Gen Xers or older who used to use soldering irons. You know, those people are all going to be gone. Like, what would you do with it? And I brainstorm with somebody what to do with it.

And the best I could come up with was like Maker. You remember that magazine and event series maker that Bill, Tim O'Reilly had sort of done. I was like, make it into a maker space. Yeah. Sell all that stuff in the back, or in the front, rather. And then in the back, just have classes and let people bring their kids there for STEM classes and how to learn how to build circuit boards or whatever. But yeah, that's not surprisingly, I'm not surprised by any of this Ty Lopez stuff.

Every time you see these people, you should just run. It's really gross. A couple more red flags here, because the Lamborghini part of this is humorous. Yes, if someone's showing off their Lamborghini to make them seem like a person of great business acumen, what they're really showing you is their ability to pay depreciation on an asset that's not even very drivable. Also, the company, REV, was promising people a 25% annual return and a 2% prefer dividend. No, that's never going to be the case. No one's ever going to offer you that kind of guaranteed return.

It's fraud. And Jason, they did use some of the money to pay back newer, sorry, older investors. They used newer investor money for that. They stole allegedly $16.1 million for their personal use, et cetera, et cetera, et cetera. I don't think humans are ever going to stop falling for Ponzi schemes, but we can at least highlight them when they touch on our space, and this was a pooled investment opportunity into e-commerce, so it kind of lands in our domain. It's fraud, folks. Yeah, it's, I guess that's Madoff style, right? He was, the new investors were paying off the old ones who were trying to redeem

their shares. Yeah. Startups are hard, and you need to have diversification. I wrote a book called Angel. It's super honest about how hard this is. If you're going to do it, you need to put in 20 hours a week for call it three, four, five years during your primary investing, you're going to need to meet with 50 to 100 startups for everyone you put a small check into, and of your 20, 30, 40, or 50 startups in your portfolio be prepared for 80% to go to zero very quickly within the first three years. That's called the J-curve. And then if you decide you want to be at this long term, you're going to have to have a strategy for exiting those investments. That typically takes 10 to 15 years. So it's an amazing career if you love startups, if you love entrepreneurship.

And, you know, you're retired with a bunch of money. I think it's like one of the great jobs being an angel investor for successful accredited investors. But we tell them in the Angel University course, which is based on the book, Angel, and the book is like 10 bucks or 20 bucks. So like, it's the greatest deal in the world. If you decide not to become an angel investor because I scare the shit out of you in the book, which I try to do. Great. And if you decide to become one, you basically get everything I learned up until that point, 15 or 20 bucks. You can go resell the book for half that amount. And of course, you're seven bucks. Books are incredible in that way. And so, yeah, it's like, these are very hard pursuits. And anybody who, like, I see this guy,

um, Grant Cardone all the time, um, on like CNBC or, um, this whole cohort of people selling, courses or access to real estate, access to startups. And I run a syndicate as well. When we do the syndicate.com, it's only for accredited investors, no retail. You have to be sophisticated, basically, or have inherited a bunch of money or won the lottery. And in all those cases, you should only invest money you can afford to lose. So I always tell people, like, with crypto or startups, if you're a credited investor, less than 5% of your net worth, let's say your net worth was 10 million, you put 500K into crypto. Let's say you lost it all. Well, the other part of your portfolio should be making 7% a year. So in one year, you've made up for your mistakes in crypto.

If you were going to retire in five years, that would not be good. But if you were retiring in 20 or 30 years, that would be just fine. You can weather the storm. So just 1%, 2%, maybe even, 100K, 200K, and be thoughtful about it, folks. Always my best advice. Yeah, I was just Googling Grant Cardone because I forgot who that was. And one of the first pictures that came up was him standing in front of a private jet, which in my experience, Jason, people who have private jets don't do. There's like two rules. There's three rules of private jets.

I know this four. I can tell you these. Number one, don't be late. I was like an hour late for a jet with Chamath. He still tells the story. It was my fault because I was like, I have a speaking gig and I'll go to Toronto with you to interview you for this other Shopify thing or whatever. But I'm leaving the shopping, this gig here.

I got to get all the way to stand and say, He's like, don't worry about it. If we're late, we can go to another. And it was like, I hit massive traffic. And we did have to divert from one airport to the other. Bummer. Second thing. Second thing.

You don't take pictures or talk about it. That's what I'm saying. Third thing, you let the principal decide where they're going to sit first. So you come in, you place your bag somewhere neutral. You don't sit down. You wait for the principal to pick their seat, which is typically if you go in, if there's like a four top in the front, like four seats, not the, no table, it would be the right one facing forward.

That's where the principal sits typically in my experience. So you can sit to the left if you're having a conversation with them or cross-room if they don't want to spread their feet out or caddy corner to them. Or you sit at the table back there if they want to be, have privacy. So you just say, hey, where do you want me to sit? You got a preference? You just say that. Yeah, because they're paying for it.

Well, yes, it's like being in somebody's car, you know, or their house. Like you don't just go into the master suite and you're like, I'll stay here. It's the biggest bag. And number four, you have to read the room. Is the principal, is the owner of the plane like reading the newspaper or doing work and put their headphones on?

Or are they like, hey, how is your day? And they want to talk. So read the room. Especially if it's a long flight. Like if you're going to Japan, you know, if you're going to Europe, this is like a 10-hour flight. You can just say,

do you have a plan for, sleeping or eating, let me know, whatever. Or you just read the room and just read the vibes. And just say, where do you want me? Boom, that's it. But part two, point two that you just said is you don't talk about it. You don't talk about private. Yeah.

So if someone's trying to show you their Lamborghini or them in front of a private jet, red flags, folks. I have been, if I'm being totally honest, looking at planes. So there is that. I may throw all these out and you might, I might take you to Vegas. with me at some point or drop you off in New York on my way back, but I have been looking at private jets. And I just can't do it.

I have not been able to pull the trigger on only because I'm just still cheap. I still think like a poor person. So I was like, I don't know, man, that seems really expensive. I mean, on the wall of my childhood bedroom, I had a sales brochure that I procured from DeSoe Falcon of their 900 EX jet. Oh, that's a great jet. A lot of my friends have Falcons. And the Falcon is just also very very.

very good per hour operating costs. Oh. But the two I like are the Phenum 300 and the Pilates PC-24. And there are companies that let you either do a fractional ownership, you can own an eighth, that's fourth or whatever. Or you can just buy a jet card for essentially 10K an hour is what it comes out to end of the day. So, you know, if I spend, I don't know,

500K every two years, I have 25 hours. I can do three trips or two trips or whatever it is, you know, cross-country or maybe three regional trips a year. But I don't need it. And I like walking through the airport, Alex. You know why? People stop you and say, Jason Calcanus, hi, your autograph. I love people.

And I love talking to people. I cannot tell you how many friendships or catch-up meetings I've had in airports. I like walking through the airport. I love going on Emirates airline. In the back, they have a lounge. After I get settled in my seat, I take the business class. I don't take the first class, as you heard on All-in this weekend. And the first thing I do is I take my laptop.

I go to the back, there's a lounge. There's like a four top table, like a diner table. And I sit there on my laptop. And I, you know, I get served, you know, some croissant and espresso. And I work. And then people come back and they're like, oh, Jay's and Galangans. I'm like, yeah. And they're like, I'm like, what do you do?

And they're like, I don't know, I want to sit and join me? And people are like, are you that guy? Are you weird? I'm like, just love people. So if you see me out, folks, I love people. I love people. If you have courtside seats to a Knicks game, I'll go. I don't even need to know you.

This week and startup, Founder University, Launch Accelerator. I'm at Jason. He's at Alex. Email me anytime. If you got a great idea for a company, Jason at calicanus.com, launch.com slash apply. If you want to apply for a meeting with my amazing team and get that process started, founder.

That university is starting in Mina. But I think we've picked all the companies. I don't know if you can still apply. mina dot I go to founding university you'll see the Mena link at the top and founding university

we do it three times a year here in the U.S. See you next time everybody, bye bye bye bye