How to Raise a Seed Round in 2026: Ask Jason | E2294

This Week In Startups is made possible by: Grasshopper Bank https://grasshopper.bank/twistLinkedIn Jobs https://LinkedIn.com/twistNorthwest Registered Agent https://northwestregisteredagent.com/twist Today's show: Jason breaks down the real math behind raising a seed round. Here's the funnel: contact 150 firms, get 50 first meetings, convert 2o into second meetings, and close 2 term sheets. PLUS Jason responds to viewer questions about why hardware is no longer a dirty word for investors, how to differentiate your startup from frontier-model companies like OpenAI, even when they're in your niche. Plus a pitch for "Founder Community College," and anecdotes from Lon's European odyssey. Thanks for the Questions: Richard Corral: CEO of Quanto: https://quanto.co/ ØnProtons on X: https://x.com/0nProtons SergeDawg on X: https://x.com/sergedawg Mahika Golani Peridot: https://www.tryperidot.com/ Shawn Sully on X: https://x.com/aroogle Programs and Accelerators Mentioned: Y Combinator: https://www.ycombinator.com/ Techstars: https://www.techstars.com/ Antler: https://www.antler.co/ PearX: https://pear.vc/pearx/ Sequoia ARC: https://www.sequoiacap.com/arc/ Kauffman Fellows: https://www.kauffmanfellows.org/ Companies and Startups Referenced: Whoop: https://www.whoop.com/ Knightscope: https://knightscope.com/ Eight Sleep: https://www.eightsleep.com/ Cafe X: https://www.cafexapp.com/ Media Referenced: New Yorker Sam Altman profile: https://www.newyorker.com/magazine/2026/04/13/sam-altman-may-control-our-future-can-he-be-trusted Off-Duty Recommendations Terra Kaffe Demi compact automatic espresso machine: https://www.terrakaffe.com/products/tk-demi Osteria Pastella (Florence, Italy): https://www.osteriapastella.it/ Timestamps: 0:00 Inside the TWiST private group chat 3:25 How to react when an investor says your "too early." 6:50 The ultimate seed round funnel 8:48 Jason's new Associate in Training program 10:09 Grasshopper Bank - Time is money. Don't waste either. Go to https://grasshopper.bank/twist and get an exclusive $500 cash bonus just for opening an account. 18:28 How have the metrics for early-stage companies changed? 20:20 LinkedIn Jobs - Hire right, the first time. Post your first job and get $100 off towards your job post at https://LinkedIn.com/twist 22:34 TWiST Bounties update 23:43 Competing against frontier labs 30:03 What signals real investor-founder alignment? 30:14 Northwest Registered Agent - Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity — Learn more at https://northwestregisteredagent.com/twist 36:07 A crash course in Bay Area startup culture 40:15 Automatons-as-a-Service (AaaS) 42:29 Who in Silicon Valley does Jason really not like? 49:59 Museum Etiquette with Lon Harris 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 Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Check out all our partner offers: https://partners.launch.co/ Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Check out Jason's suite of newsletters: https://substack.com/@calacanis Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Jason Calacanis?

  People in our secret group chat have questions for me. Some might be spicy.

• 0:05Speaker 01

  What do you think founders should be doing to try to sort of give themselves a little bit of moat against OpenAI?

• 0:09Jason Calacanis?

  There's always going to be a feature set that the interface of the large language model is not going to add.

• 0:15Speaker 01

  Out of all the people in Silicon Valley, who's the one person you really don't like the most and why?

• 0:20Jason Calacanis?

  Some people have damaged the reputation of the industry and the user base. And then some people have just maybe screwed over friends of mine. I've been a consistent critic of every time he had a chance to do the right thing for humanity. He picked his own self-interest. It's a level of selfishness in decision making that and cutthroatness that I understand, but I wouldn't do. And I think has damaged the reputation of the tech industry. The two people I'm talking about are two of the most successful people ever in the history of business.

• 0:51Speaker 02

  This week in startups is brought to you by Northwest Registered Agent. Get more when you start your business with Northwest. In 10 clicks in 10 minutes, you can form your company and walk away with a real business identity. Learn more at northwestregisteredagent.com/twist. LinkedIn, thanks to our partners at LinkedIn. Post your job for free at LinkedIn.com/twist, then promote it to get access to LinkedIn Jobs new AI assistant. And Grasshopper Bank. Time is money. Don't waste either. Go to grasshopper.bank/twist and get an exclusive $500 cash bonus just for opening an account.

• 1:29Jason Calacanis?

  All right. Lon Harris is here. I'm Jason Kalkanis. People in our secret group chat on X, formerly known as Twitter, have questions for me. I'm going to answer them. Lon is going to give me these questions. He's vetted. Some might be spicy. It could be political. It could be technical. It could be startup related. It could be life. It could be health. Could be dating. Could be anything. I'll answer any question for our community. If they have it, if you want to join our community, X.com/twist startups. That's our handle. If you DM that handle, we know that you listen to the pod and we will add you to that group. The group's got 400 people in it or so. And it's quite a nice little group talking about the topics of this week in startups of Twist.

• 2:14Jason Calacanis?

  Let's get started.

• 2:15Speaker 01

  Yeah, I would add if you're very active in the group and participating and sharing great stuff. There's even a higher level insiders group. Maybe you can add that one. That's very rarefied. We don't, we don't just let anybody into that.

• 2:27Jason Calacanis?

  It's a funnel. We have everybody following the account. Then we have four or 500 people in this crazy group chat. And then I think we have 10 people who are like the best people in the group chat, who we know are good actors that we're filtering into like just a small group. So it's, I don't know exactly how to build community these day, this day and age, but I'm going to start doing more dinners and live shows. Since people want to get together in person and a lot of people want are sad and lonely. And staying at their ranch, smoking cigars, sitting on a bench and want to see more humans.

• 2:59Speaker 01

  Get out in the world. Yeah.

• 3:01Jason Calacanis?

  That's what I want to do. I need to get out in the world more. So yeah, more dinners, more hanging out, more live shows.

• 3:06Speaker 01

  So first question comes from Richard Corral of Quanto. It is a accounting firm in the age of AI. Here I'll share their website. They're basically, he describes it as an AI powered wealth management platform. And so here, here is his question. We have a $10 trillion AUM lead interested in us as clients and investors. They gave never seen something like this before level feedback, but then ultimately told the company they're too early for now. But they want to stay updated. So Richard wants to know your advice on how to combat the challenges facing startups with that early stage status, even when their tech is advanced and innovative and looking forward.

• 3:50Jason Calacanis?

  Sure. Each investor has a different area of speciality. And you should look at what stage of a startup they invest in most. And whatever they tell you is not as important as what they do. Right? So if you were looking at a person and trying to judge them, the best way to judge a person. Is to look at their previous behavior or to watch them doing the job you're asking them to do. This is first principles thinking. If you go to a family office and you are in year zero of your startup, you are not incorporated yet, you have a demo, a product, they're not going to invest unless they have a history

• 4:35Jason Calacanis?

  of investing in entrepreneurs who are not yet incorporated and who don't have a product in market yet. Now, you have to divorce what people say in social settings, especially investors, from their behavior. If you look at my firm, Founder University is designed as a product occurring in three different geographies, three different continents around the world, twice a year each, six cohorts a year, Riyadh, Tokyo, and in the US. And we explicitly ask people to come who have two or three founders, and you don't need to be incorporated, you don't need to have customers yet.

• 5:18Jason Calacanis?

  We want to meet you in year zero, and then the accelerator, we want to invest, and we want you to be incorporated at that point. Now, if you go to a family office and they've invested in seven things in the last five years, and all of those things are private equity deals that their friends brought them, and they put $30 million into each deal, how on earth are they going to put 125K or 250K or what you're looking for in your seed? They're not. But you got introduced to them, they took the meeting, they're going to say nice things. You have to divorce the nice things they're saying from the reality of what they do. That's all. You have now somebody who likes you, okay, great, but they say that to everybody. What you want to look at is, do they actually invest in your stage of startup?

• 6:02Jason Calacanis?

  The answer is probably no. Therefore, who does invest? Y Combinator, Techstars, Antler, A16Z, Pair has a great summer program, Sequoia has ARC, I have Founder University, Launch Accelerator. Go to those programs first. Get your 125K, your 25K check, your 250K check, get your first five customers, and then you can go back to them, and they might be a greater later stage. And in terms of numbers, in order to get a seed round today, you need to contact 150 seed funds, get 50 meetings with seed funds to get

• 6:36Jason Calacanis?

  20 second meetings to get two to give you a term sheet. That's the funnel today.

• 6:44Speaker 01

  Yeah.

• 6:44Jason Calacanis?

  If you're not doing that, you're just not playing the game on the field. You may hear of people who get funded, you know, they take a meeting and they instantly get funded and they weren't even looking for funding. Yeah, those are memorable stories because they are not the norm.

• 7:01Speaker 01

  Right.

• 7:01Jason Calacanis?

  They're notable because it's not the norm. That's why you're hearing those stories. The norm that we see on the field is emailing and trying to get in touch with 150 different investors, getting on the radar and getting a quick Zoom call with 50, getting 10 or 20 of those. In other words, 10% of your initial target list to take a second meeting. 150 targets, 15 second meetings, that would be a reasonable goal.

• 7:25Speaker 01

  Yeah.

• 7:26Jason Calacanis?

  If people are not willing to take a second meeting, you're not really, you should really only judge second meetings. People are not obligated to take a second meeting. Therefore, a second meeting is notable. Okay, I hope that helps.

• 7:41Speaker 01

  Yeah, I think that's, it's interesting. It's how, how many different sort of fields and kinds of work that's applicable to like, people think to become a content creator, you just create like two or three videos and then one goes viral and now you're Mr. Beast. And it's like, no, it's hitting it every single day. It's doing it hundreds of times until you find your voice and refine everything. And then you start actually growing and I think it's kind of the same across just about any discipline. All right, speaking of Founder University, at OnProtons on X had a pitch for you for what they call Founder Community College. So their question is, why is there no Founder Community College to go alongside Founder University? It would help with the coming wave of 500K to $5 million AI-driven, single-person, owner-operated companies.

• 8:26Speaker 01

  So you're not worried about fundraising, you're not worried about board seats, you're not worried about cap tables. It's just focused on tools and building great products. What do you think, is there, can you see a level between, you know, Founder University that's for, you know, people who are even earlier?

• 8:42Jason Calacanis?

  So funny they mention this. I literally this weekend. Was asking about the accreditation laws and how I could give a degree. I was asking this because we have an associate in training program for the venture side of our business. We're hiring six people in June to be part of that. They start as researchers, they become analysts, then they become associates. It's a basically a three-year program to go through each of those titles. 60, 70, 80, 90 K is like sort of the career path in terms of salary. So instead of paying for a degree in venture capital, we pay you is the way I tell people to look at it. And we hire twice as many people, really three times as many

• 9:24Jason Calacanis?

  people as we need because we think one or two of them are going to opt out. It will be like not the career for them. One or two of them, we will not continue on with. In other words, we don't think they have what it takes. And then one third, we're going to keep and they're going to become all-stars in our firm. And we want to replenish that. But I had so many people say to me, I would like to send my child to that. Can you charge me 60 K a year for two years and I'll pay you 120 K to teach them how to be a venture capitalist because there is no course in that. There's like continuing education. It turns out I'm not legally allowed to give a degree in being a founder or a degree in being a venture capitalist. I could give a certificate. Right. But not a degree.

• 10:09Jason Calacanis?

  When you're a founder and you're moving fast and you want to close a big deal, a traditional bank can kill your momentum. Long approval processes, clunky outdated systems, not intuitive. I mean, some of these systems look like they were made in the 1970s and have never been updated. Not all banks are designed to work for startups. We all know that. And that's exactly why Grasshopper Bank was created. Grasshopper is a real federally chartered bank, but with the kind of financial tech stack that you'd build for yourself. They're going to open your new account in just minutes, not days. That's a key pain point. An integration friendly platform with real-time transfers and AI tools that are going to save you even more time, all without trading your budget on a bunch of unnecessary fees. That's where they get you. And because you're a value twist listener,

• 10:53Jason Calacanis?

  Grasshopper will drop a $500 cash bonus into your When you use the promo code TWIST, T W I S T, start building without the slowdown at grasshopper dot bank slash twist. Terms and conditions apply. Grasshopper is a federally chartered bank, member FDIC. And so that's what I think a lot of people do with these continuing ed certificates, etc. So I would have to partner with a local university in the US to do this. And there are some that do this, but you can give certificates or a diploma, but you cannot give a degree. That's the word that I think gets you in trouble. Now, outside the US, there are some universities

• 11:34Jason Calacanis?

  in the UK that will let you use their programs to do a UK accredited degree. And then there are islands, like there were some islands people would go get degrees in medical practices. Sure, yeah. I mean, I know that's a big like Central American thing. People go down there to get their degree. Right. And like dentistry and other things. And it does somehow work in the United States. I don't know about those. They, it seems fugazi, fugazi. But I have been thinking about this because I do think college is broken. So next year, I told my team, I want the associate and training program that we start in the summers to be so good this time. And you and I were

• 12:17Jason Calacanis?

  talking with Jackie about it. We're going to have like a Monday morning session and a Friday end of the week session where we do professional training and then in between they work at one of the business units inside the company. The goal, I think, is for that training program, those two, two hour sessions that bookmark the week to be so good that next summer, when we do it, we could literally charge for it. And literally say for $50,000, you can come work here for nine months out of the year, take your summers off for 10 months, and for two years, and then take on Kauffman Fellows. There's a program called Kauffman Fellows. You can pull it up on the screen. Kauffman Fellows charges, I believe, $80,000 or $90,000 for

• 12:59Jason Calacanis?

  two years. Somebody look up the price. It was extraordinary. And then they were like, oh, well, that's for people who are already in it. So Kauffman Fellows is this. Um, program that people do and you can see it's incredibly diverse. They have like scholarships and stuff like that because our industry, the venture industry was known for being maybe 10 years ago, a little too, uh, dare I say now and white and Ivy League.

• 13:25Speaker 01

  Sure.

• 13:26Jason Calacanis?

  Uh, but they've had a thousand fellows. Some of them you might know, uh, there's Jenny Fielding, I know her, um, and I don't know which one of these peoples are, are paying for it. There's Monique Woodard. I'm a, I'm an LP in her, uh, fund. So I don't think there's anything wrong with this program necessarily. Uh, there's Mamun, but I do think it's a bit of an elitist group. Um, and it's, I think $90,000 a year. I don't know if someone has looked it up.

• 13:58Speaker 01

  Jacob looked it, producer Jacob looked it up for us. The Kauffman Fellows two-year program tuition is $80,000. Application fee of $100 if submitted by the early deadline. If you miss that, it's a $300 application before the actual end of time deadline.

• 14:13Jason Calacanis?

  So I think I could have 10 people in this program, charge them 50K each. That'd be 500K. Then I could hire two full-time people to work on it.

• 14:19Speaker 01

  Yeah.

• 14:20Jason Calacanis?

  And create a program and I think it would be better than Kauf. I know it would be better than Kauffman Fellows because you get to come with me to Saudi, come with me to Tokyo. See those programs and interview companies and I think they're not even in office for that much. I don't, I don't think that this, I think this program is all virtual. I think they maybe spend a couple of weeks together.

• 14:37Speaker 01

  Yeah, Zoom meetings probably mostly, but.

• 14:39Jason Calacanis?

  I wonder like what the actual curriculum is. If somebody could send me the curriculum or send me like the agenda and what it is, I would love to study what Kaufman has done. I don't know if it's public, but anyways, I'm not um, dissing them for having an incredibly overpriced elitist program.

• 14:54Speaker 01

  Yeah.

• 14:55Jason Calacanis?

  Well, I am thinking on a competitive basis, like maybe I could create a better program and then for Founder University.

• 15:04Jason Calacanis?

  I would be fine with partnering with a university that wanted to give a founder university degree and make it a two-year program and it just teaches you how to be a founder and embed you in companies. I mean, sure, why not?

• 15:16Speaker 01

  There's probably some young people that would be interested that are interested in entrepreneurship, but wouldn't even know where to get started. I feel like that's what Founder University is good for. Like, here are the 10 terms you don't know. Here are the concepts everybody's talking about that you're not familiar with. Like, that's where I think we can really help young.

• 15:31Jason Calacanis?

  Or maybe you put the two together and it's just company building and you have two tracks, the Founder University track and the Associate.

• 15:37Speaker 01

  Right.

• 15:38Jason Calacanis?

  The Venture University track. You have the two tracks and you major in one, minor in the other, but you learn both sides of the table.

• 15:45Speaker 01

  And I mean, we're also, I bet you, Coffin fellows is not doing media training. You'd also come out of this knowing how to make a newsletter, knowing how to do social media, knowing how to make a podcast, you know, like all those communication skills that you wouldn't get that are so important in this field. I mean, we talk about it all the time because we're constantly booking investors and venture capitalists and founders as guests, but there are a lot of brilliant founders with great companies or brilliant investors with great portfolios, but they're dead air on a podcast. You can't book them on things.

• 16:14Jason Calacanis?

  Yeah, for sure.

• 16:14Speaker 01

  And so like, we also help with those skills that are important as well.

• 16:18Jason Calacanis?

  Yeah. Now, unfortunately, because some idiot started a podcast about startups 16 years ago, now every venture capitalist has to have a podcast.

• 16:25Speaker 01

  Yeah, geez. Those four billionaires got together to.

• 16:29Jason Calacanis?

  Oh, so brutal.

• 16:30Speaker 01

  During COVID and now we're all stuck.

• 16:31Jason Calacanis?

  Especially since one of them is not a billionaire.

• 16:34Jason Calacanis?

  I actually think three of them are not billionaires, technically.

• 16:37Speaker 01

  Wow, that's breaking news. Huge if true.

• 16:39Jason Calacanis?

  Yeah, I don't think Freeburg's a billionaire. Maybe on paper with a hollow stock.

• 16:42Speaker 01

  People, people refer to you.

• 16:44Jason Calacanis?

  I don't think Chamath's a billionaire. I don't.

• 16:45Speaker 01

  People just refer to you all as billionaires. I just assumed. I've just been guys.

• 16:48Jason Calacanis?

  I might be a billionaire. I don't know.

• 16:50Speaker 01

  I feel like, yeah. Sacks and Chamath, maybe, pretty close.

• 16:53Jason Calacanis?

  Maybe.

• 16:53Speaker 01

  Chamath, after that Grok deal, come on.

• 16:57Jason Calacanis?

  I think he probably owned 10, 20% of that.

• 16:59Speaker 01

  Yeah, and maybe, like, obviously not liquid, but I feel like he's probably.

• 17:03Jason Calacanis?

  Yeah, I mean, that's always the thing is like, and then who cares?

• 17:06Speaker 01

  Yeah.

• 17:06Jason Calacanis?

  Like, honestly, the more I look at wealth, uh, wealth creation, once you get past like this basic $10 million mark, you're, you have the F U money. You have the FUM.

• 17:20Speaker 01

  Right.

• 17:22Jason Calacanis?

  And once you have FUM, it doesn't matter. You could ski, you could podcast, you could do whatever you want, and it's exactly $10 million.

• 17:30Speaker 01

  I think that, yeah.

• 17:31Jason Calacanis?

  That's exactly the F U M number. FUM starts at 10 million.

• 17:34Speaker 01

  10 million.

• 17:35Jason Calacanis?

  Once you have that, you make 5% on your money, which is a half million dollars a year, which means, you know, after taxes, four or 500,000 a year, you can just exist.

• 17:44Speaker 01

  Yeah, I'd be back in Florence right now.

• 17:46Jason Calacanis?

  You'd be back. How was your trip, though? I didn't ask. You had a good time?

• 17:48Speaker 01

  Amazing trip. I had a great time. Yeah, Rome, Rome.

• 17:51Jason Calacanis?

  How many days did I give you off?

• 17:52Speaker 01

  It was, you kept saying 22. It was technically 19 days off. A lot of those were weekends. So, so it was, I, I think it was like 14 work days off total.

• 18:02Jason Calacanis?

  It felt like you were gone for two months. My God, you definitely have job security.

• 18:05Speaker 01

  It did.

• 18:06Jason Calacanis?

  I was like, I'm CCing lawn, and I'm like, Jesus, when is this guy gonna be back? All right, give me another question.

• 18:10Speaker 01

  All right, let's go into number three. This is from Serge Dog, also on X. Uh, if you

• 18:15Jason Calacanis?

  Love Serge.

• 18:16Speaker 01

  If you compare early-stage startups today to 10 years ago, what has changed the most in how you evaluate them? And in particular, he's interested in, what do investors overvalue, do you think, from the like, old-school, conventional wisdom playbook? What traditional must-haves have become optional? And what expectations are now table stakes? Like, how, how has the landscape shifted for you as an investor in early stage?

• 18:40Jason Calacanis?

  Yeah, I mean, the number one thing is the amount of capital it takes to get a product to market, and to the amount of time it takes to get product-market fit. That is dramatically decreased. So over time, we with vibe coding or the no code revolution, we had these moments where it seemed like really no code was one cloud, the cloud era was another, where the cost of running a startup went down 10x. It used to be 3 million, then it went to 300. And when that happened, because of WeWork outsourced accounting and legal and not having to stand up your own data center, it used to take 20,

• 19:24Jason Calacanis?

  30 people and 3 to 5 million dollars to get your product to market. That was in the web 1.0 era, the 90s. Seed round would be 3 million, it would take 12 months to get your product ready to go to market. And you had all of these expenses which were considered non-negotiable and you had to do them. You had to have a PR firm, 10K a month for 18 months, 180K. You had to get an office for 25K a month. You had to put a 250K letter of credit down. So that was another 300,000 a year for two years, 600,000, 250K letter of credit. It was basically a million dollars to set up your office. You had to put a half million into service and now you have 1.5 million. You had to spend 100K on legal, 1.6 million.

• 20:07Jason Calacanis?

  You had to hire an HR person, an accountant, and a lawyer, another 250K. Now you're at 1.8, 1.9 million. You get the idea. Then you hired a couple of product people, developers, you're at 3 million dollars. You finally get the product launch and you figure out if you're going to win or not. Adding a new member to your team is a crucial decision. You don't want to rush into a hiring situation that you will regret. But if you're a busy founder, you also don't want to spend a ton of time in the trenches looking for that perfect candidate. Instead, you need a partner and you need a trusted partner and LinkedIn Hiring Pro is that partner. How do I know this? Because I use LinkedIn Hiring Pro. You want a real world testimony? All right, here you go. We recently hired a new customer success manager. They handle

• 20:49Jason Calacanis?

  all the advertising accounts here on This Week in Startups. And they ensure that we're keeping all of our wonderful partners happy. LinkedIn helped us connect with an amazing Candidate right here in Austin and he had exactly the combination of experience we were looking for. It's magic, it's alchemy, it's everything for me to find a great team member. So hire right the first time. Get started by posting your job for free at LinkedIn.com slash twist. Terms and conditions apply. That's LinkedIn.com slash twist. Then the Y Combinator era, the cloud computing era meant you work at home, three people, you eat ramen for 300K. You could stand up a startup in under six months. Now it, then it went to like 30K,

• 21:34Jason Calacanis?

  just paying for some servers, but maybe you got free credits and you and your partners never met in person and you just shipped and you vibe coded stuff and you got your first customer, then you applied to Y Combinator or Techstars or Antler or one of these incredible programs, Launch Accelerator. Now it's kind of like I built a, I vibe coded a product. I got to 100K in revenue and then I applied to Y Combinator. Then I applied to Launch Accelerator. So that's what we're seeing. And so the time from idea to first customer and first customer is light product market fit. You can convince people to pay for anything, but let's just say some level of product market fit. That's down to weeks. It's down to a weekend.

• 22:19Speaker 01

  Yeah, I was gonna say it's out of days. We've seen companies on the last few months of the show that are literally like, oh, I built this 14 days ago and we're talking to them on the show about all of their hundreds of customers.

• 22:29Jason Calacanis?

  Our bounties program is a perfect example of that. We have two bounties out this week in startups.com slash bounties or bounty and the one for the fact checker, real time fact checker, we have 15 people and I think three of them are really good. That was like in under 30 days and then we're doing another one, another $5,000 bounty for annotated. What I'd like to do with one of those companies is actually make it a startup. So I'll give them the prize.

• 22:54Jason Calacanis?

  But then I want to hire them and incubate the startup. So that's my hope is that the real time fact checker becomes an actual startup company or annotated becomes a real startup. So hoping to find a founder or two I can hire and put into like a startup or a company I incubate.

• 23:09Speaker 01

  And by the time this airs on VOD, we'll have already picked a winner for our side cast.

• 23:15Jason Calacanis?

  Or winners.

• 23:16Speaker 01

  Or multiple winners. You never know. We've seen some amazing submissions. There are really some great submissions. All right. Next question. From Founder University vet Mahika Golani of a company called Treya. She wants to know, how should startups think about differentiating when frontier labs release products in the same vertical that they're building in? Of course, this is a huge story. People are always worried about, are they going to get death by clawed and is Anthropic going to just take over their business? So what do you think founders should be doing to try to sort of early differentiate, give themselves a little bit of moat against OpenAI, Anthropic and others?

• 23:52Jason Calacanis?

  Absolutely. So there's always going to be a feature set that the interface of the large language model is not going to add because of clutter and confusion. So let's take travel. We had a great startup, Rome, and they, I think, were built on like the preview, like the 2.5 of, and you can look up Rome and we probably have it in our database here. I think they wound up giving the money back to investors because in ChatGPT 2.5, they, that was like an API, and then they were letting you put in, I want a three day trip, I want to go to Italy, I have three weeks, my boss gave me 19 days to be out of the office.

• 24:32Speaker 01

  Yeah, it was great.

• 24:32Jason Calacanis?

  What should I do over my 19 days? Because my boss is so goddamn accommodating. And Rome was like one of the best previews I've ever seen. It's in our database. It's not public because it's shut down. But let's take that one as a travel example. You can ask all these travel questions inside. Of ChatGPT and people do.

• 24:51Speaker 01

  Mm hmm.

• 24:52Jason Calacanis?

  But if you were to build an interface around it and features around it, and you're constantly adding features and then building a community around it, the community, the support, these extra features, they're not what ChatGPT is going to work on. They're just going to ChatGPT X, they're going to just give you your basic output. But what if you want, when you get the basic output, you want to play multiplayer mode? So you and I and Amanda and William and Bianca are doing our next trip to Tokyo. And we're like, hey, let's do this as a group. Let's all research where we want to go for three days on a bullet train. Let's all research where we want to go for breakfast, lunch, dinner and shopping.

• 25:34Jason Calacanis?

  And then we all do our research, but we're watching each other do the research. And then we click and we vote and we add it to an agenda. And then we finalize the agenda, all that stuff roam around with the company. That's not going to be done by ChatGPT. So you can build all that around it. And then you could build the concept of a virtual travel agency, somebody who uses AI and does all this itinerary with them and you pay them per hour to do it. And or you pay them for ground support. When you're on the ground in Tokyo, they match you with a local guide. Those things will not be done by ChatGPT, if that makes sense, right? So that's, I think, the differentiator you can do. Tax GPT, another example of it.

• 26:13Speaker 01

  I was just gonna say, having just planned a trip, you do look things up on AI, it's natural. I use it in place of a search engine at this point. But then there's also Viator and TripAdvisor and all these other platforms. And it's using both. It's not one or the other, like I think a lot of people think. It's sort of, you know, you layer these different tools on top of one another to get the best result. So I think there's truth in that.

• 26:37Jason Calacanis?

  I think community, multiplayer mode, support, services around those things, they're just not going to do that. They're not going to create a marketplace with local guides. One of the things I want to do when I go to Japan next time is there are now food guides who have come out.

• 26:57Speaker 01

  Yes.

• 26:57Jason Calacanis?

  And, you know, one of the things is because of social media, everybody goes and, you know, does a video of the memorable stuff.

• 27:06Speaker 01

  Right.

• 27:07Jason Calacanis?

  And then all the influencers go there. But it turns out like unless you speak Japanese and you know the surrounding area, those places are targeted. American tourists, but there's 20 other places with pancakes that are just as good or better that don't have a line. And you can hire, there's one guy who's a bit robust and his thing is like, he's, I don't know if he uses the term fat or, you know, whatever. He's your jolly fat guy. Who takes you on tours. And I guess there was a movie. Yeah, there was a movie about like, um. Brendan Fraser was in about like.

• 27:41Speaker 01

  Rental family, yes.

• 27:43Jason Calacanis?

  And the concept is?

• 27:44Speaker 01

  He's an American actor and he's hired to pretend to be like a surrogate father. In this family that doesn't have a dad around. And apparently this is, I mean, the, the story behind the movie is that this is a real service in. Japan that you can like rent a fake family member for occasions or for times where you are particularly missing having like a dad around. And then he becomes, of course, bonded with the family and it becomes a sweet story like that.

• 28:11Jason Calacanis?

  You could also do rent an old guy for fun.

• 28:15Speaker 01

  Yes.

• 28:16Jason Calacanis?

  So that is a thing.

• 28:18Speaker 01

  And there's a rent a boyfriend, rent a girlfriend services. Those get talked about a lot and it's not a sex worker thing. It's just like, I want somebody to go to this ball game with, you know, like it's that kind of thing.

• 28:29Jason Calacanis?

  Yeah, but the, the renting of food thing is like, that's even better. So let's say you have this idea for an AI planner. But then the AI planner has to result in something like you're on the ground. Okay, so you get the basic chat GPT features for free. But we could also connect you with somebody who books this or gets in line for you, brings you, translates, it sits with you. Gives you the backstory, takes you in, arranges for you to go in the back and make the ramen, you know, between, you know, lunch and dinner service.

• 28:58Speaker 01

  Sure. Yeah. And Rome, we booked a, uh, one of those golf cart tours where the guys drive you around the golf court. We got to go into a bunch of crypts and stuff. Under the churches because he like would give, he would give the nuns like five euro. He knew where to go and like who to talk to. So we got to see like.

• 29:11Jason Calacanis?

  Genius.

• 29:12Speaker 01

  The tomb of Saint Cecilia and all this sort of aqueduct under the Trevi Fountain stuff that most tourists don't get into, which is cool. So yeah, I think that's a, yeah, there's, there's a, there's a service there if you can find your sort of spot in the stack. Yeah, for sure. So from. Paradot on X, they are a dating app for serious daters. I'll bring it up here on the screen. They compare it to being like, it's like being set up by a friend as opposed to just standing on an app by women for women. A new take on the dating app. That is their business, their question. And I quote, founders are often told to find the right investor, but most advice reduces to stage, sector, or warm intros.

• 29:53Speaker 01

  When you evaluate founders, what tells you there is real alignment beyond the obvious category fit? And then the founder adds, they're asking because fundraising feels to them like a marketplace with weak signals and poor coordination. They feel like the best founder investor matches are not just about who invests in their space, but who sees their problem the same way that they do. Your thoughts?

• 30:14Jason Calacanis?

  Okay. So you've identified a real problem and you put together a solid solution and a business model that you believe in. So you're all set to launch your new company, right? Not so fast. If you want investors and potential customers to take your new business seriously, you need to consider forming a Delaware C corp. And that's where Northwest Registered Agent comes in. They're going to give your new company a real identity. That means an address for your public filings, a domain, a custom website, a business email, and of course, a phone number. And that's going to take just 10 minutes and 10 clicks. They don't charge hidden fees. Customer service is available around the clock. They're not overwhelming your inbox with spam and they make it easy to cancel at any time. So get all the advantages of a Delaware C corp, independent, regardless of where in

• 30:59Jason Calacanis?

  the U.S. you're operating from. Visit northwestregisteredagent.com/twist for more details and the links are in the show notes. Okay. So there are investors who, investors have all different sets of signal and processes in which they invest. I have a friend who's an investor at True Ventures. He only invests on things that come through his network. He's an older guy. He's probably 60 now. And he basically looked at his career of 40 years and said, or 30 years and said, you know what? All the great investments came when one of my friends told me about a company. Therefore, I'm not taking any emails. People can email you all they want. The only way I'm taking a meeting is if another venture capitalist or a portfolio founder tells me I should meet with it.

• 31:43Jason Calacanis?

  And he, and he just uses that as his filter. And I think it works for him. Then there are people like Y Combinator or us, you come to launch.co/apply. We meet with 10% of the companies that apply every week. So some weeks we get 200 people applying, sometimes 500. We meet with 25 people a week now. We were meeting with 140. That was too much. So we meet with those 25. At the end of the year, you know, all said and done, we've done three, four, or 5,000 meetings and we've invested in 100 companies, called down from 10 to 20,000 applications. You get the idea. But we don't invest in biotech or military tech right now. We're looking at milita- we actually started with military tech, but we didn't do biotech. We didn't previously do bio-

• 32:27Jason Calacanis?

  you know, and everybody's got a different preference. So figuring that out is hard and it's work. And I think the best thing to do is to study what people have already done. You get a Crunchbase account or any of those things. You start following on social media, the different firms, and figure out 150 different firms that invest at your stage and have invested in similar companies. So if you're a marketplace and they did Uber or Thumbtack like I did, or they're doing fintech like I did Wealthfront and Robinhood, you can know that when you come to me, we share that. So if you're doing a fintech marketplace, you're like, hey, J. Cal, you did Thumbtack and you also

• 33:10Jason Calacanis?

  did Robinhood. We're doing a marketplace for financial advisors and you pay financial advisors by the hour instead of 1% of your net worth or your portfolio size. So I'd be like, oh yeah, that's a really good idea. I would love to hear that pitch. Yes. So that's your job. And you have realized now as an investor that this is not a clean, easy to navigate marketplace. It's a bit bespoke and underground. We have a product called Whisper Network for our founders where they get to go in and search through and put in their materials, ask us for an introduction. And even with that tool, it's still hard. You're hunting, you're pecking, you're doing research. I think AI will make it a little bit better, but it's your job. It's tedious. It's a full-time

• 33:53Jason Calacanis?

  job. Treat it as such. That's why if you have three, three, three.

• 34:00Jason Calacanis?

  Co-founders in a company, one of them can focus on the product, one can focus on sales, and one can focus on corporate development. Corporate development is another fancy way of saying raising money.

• 34:09Speaker 01

  Yeah.

• 34:10Jason Calacanis?

  And that's what you need to do. You have to look at fundraising as a full-time job. You have to collect investors and build deep, meaningful relationships with them over time.

• 34:17Speaker 01

  Sort of the same answer as number one. Like, it's just, it's about legwork and putting in the hours and, you know, shoes on the pavement, as they say. You know, it's like about just hitting the streets and hearing the pitches.

• 34:28Jason Calacanis?

  It's the sales funnel. You have to qualify each sell. Are you qualifying each investor? Do they invest? Have they invested in your stage? Are they actively investing? Or is their fund in maintenance mode and they're in-between funds? What check size do they do? Do they lead a deal or do they follow a deal? Are they like my friend and they only take intros from existing founders? Okay, then you have to do the work to meet one of the founders, then in order to meet them. Okay, are you willing to do that work? So if you have 10 great VCs you want to meet with, maybe your best strategy is reaching out to five of their founders, meeting two of them, and then using those two founders to get one of them to introduce you to a partner over there. Now, you're talking about

• 35:12Jason Calacanis?

  sending 50 emails to founders to get 20 meetings, to maybe get on the radar of those 10 venture firms, maybe get on the radar of three or four of them. So again, that's the sales funnel.

• 35:24Speaker 01

  Yeah, it's like, it's like-

• 35:25Jason Calacanis?

  And you have to treat it as-

• 35:25Speaker 01

  It's like when you're applying for your summer jobs as a teen. And, you know, like, at first you're like, "I filled out three applications. I went to the ice cream store and the bookstore." And, and it's like, no, no, you gotta fill out 100 applications to get that one interview and to get that job. It's the same kind of story.

• 35:40Jason Calacanis?

  Yeah. And, you know, you can be creative about it. Like, there was somebody I saw who went to San Francisco and put the pitch. You can, somebody can look it up here, the producing team. They put the pitch for their startup on the back of their laptop, and they just sat there in a cafe in South Park, I believe, which is not South Park, the TV show, but a little park in San Francisco where there's a couple of cafes and there's, VCs tend to be around that park, or there's some number of VCs. And they just said, "I'm just gonna sit here and run into some people." The, and there was a Paul Graham quote, or a video clip that went viral recently. It turns out, San Francisco and the Bay Area are very unique in that the startup- Culture there is to help people without an expectation of short term rewards.

• 36:24Jason Calacanis?

  And everybody helps everybody. This podcast was my way to give back. And that's why I've done 2000 episodes of it. People tell me all the time, oh, my God, you really helped me. I'm like, okay, I've never met you. They're like, oh, no, I listened to your podcast and inspired me to start a company. Then I started my second, then I met somebody who was on your podcast because I emailed them and told them it was a podcast. That helping people without expectations of return is a unique part of the tech industry and bear culture. You can only experience that by going to the Bay Area and meeting people.

• 36:50Speaker 01

  We found this post, the guy who put a sign on his laptop. I'm gonna, I'm gonna share it right now. Thanks to producer Jacob, who dug that up. Yeah, a guy put a sign on his laptop, AI B2B startup raising pre seed product is live. Come say hi. A few investors came up to him, no cold emails, no pitch deck, no intro, just visibility in the right place. So there, your laptop.

• 37:10Jason Calacanis?

  Love it.

• 37:11Speaker 01

  As a billboard would sort of be the concept there.

• 37:13Jason Calacanis?

  There you go. Yeah, people see you coding.

• 37:15Speaker 01

  We got a, we got a what? Do you want to do one or two more or you, you're, you're?

• 37:18Jason Calacanis?

  Sure, keep going.

• 37:19Speaker 01

  Uh, we got a, we got a.

• 37:20Jason Calacanis?

  My energy is good.

• 37:20Speaker 01

  Good question in from one of the live viewers right here on this very live stream we're doing right now from at Yadon 9884. What's the best path for a bootstrap hardware founder? Once the prototype is real and nearing profitability? Would you stay lean and grind revenue or start bringing in strategic people before you scale up?

• 37:40Jason Calacanis?

  Yeah, I think you should get investors if you're at that point and investors have totally 180 their position on hardware. It used to be hardware is hard. I don't want any part of it. Now it's hardware is, is the only, one of the only moats left. I love hardware. Plod is doing a great job with that. We just had on the program, somebody made a bookmark that goes into your book. And then you can scan it and Alex was like over the moon with this product. And I was like, why do I need that? Different strokes for different folks, but hardware.

• 38:07Speaker 01

  Yeah.

• 38:07Jason Calacanis?

  Is now a way to get lock in whoop as a hardware product, you know, has some amount of lock in my eight sleep. All of this now has become a moat and a way to increase the fidelity and the usefulness of a product. So yeah, hardware is no longer. A blocker with investors, which is really fascinating to me. I invested in many hardware companies, Terra Cafe, Cafe X. We had a butterfly, which was a drop cam, you know, camera ring competitor, didn't work out. We had a smoke detector back in the day before other people came out of smoke detectors. You know, most of these things fail and Eight Sleep succeeds. It's just Terra Cafe is succeeding really well.

• 38:49Jason Calacanis?

  Cafe X is still going and be actually doing really well. But hardware is hard.

• 38:53Speaker 01

  Yeah.

• 38:53Jason Calacanis?

  And it just takes a little more capital. So you're gonna have to find people who are comfortable with investing the capital. And there are now a large number of hardware companies. You can work backwards to them. Kickstarter is still like a very viable option.

• 39:06Speaker 01

  Sure, yeah.

• 39:07Jason Calacanis?

  Doing viral ads to get your first thousand customers to give you a thousand dollars and, you know, charging them three or four times what the retail product would be to go first. You get, you know, dummies like me who are like, yeah, I don't care about the price. I just want to be the first to have it.

• 39:21Speaker 01

  Yeah.

• 39:22Jason Calacanis?

  Great. You know, whether it's like the Tesla Roadster that I paid 150K for or countless Kickstarter's I've paid for and, you know, the boxes are in my closet unopened or I used it once. It was like, oh, that's interesting. I learned something and now I move on.

• 39:37Speaker 01

  I wonder if robotics is gonna really supercharge this whole thing. Like you're already, you could drop a few grand and get a Chinese humanoid robot at this point. Like soon that's gonna be like its own hardware categories. People buying like weird little new robot designs for their house.

• 39:50Jason Calacanis?

  I think figuring out what to do with commoditized robots is gonna be a very interesting business.

• 39:56Speaker 01

  Yeah, I'm looking forward to that.

• 39:57Jason Calacanis?

  And I think they, yeah, they ultimately will be a dollar or $2 an hour is my guess. So if you think about, you know, eight thousand.

• 40:05Speaker 01

  You don't shell out all the money for the hardware you buy. You pay less and then every month you gotta pay your $12.99.

• 40:11Jason Calacanis?

  If I was making Optimus or Figure, I would go to Amazon and say, what do you pay somebody to sort packages? They'd say it's $27 an hour and then fully baked, it's $35 an hour. People sue us for workman's comp, insurance, all this other stuff.

• 40:26Speaker 01

  Right.

• 40:26Jason Calacanis?

  And I'd say, okay, we'll give you a figure, robot. You're currently paying $30 an hour fully baked, you know, $20 to the person, $10 plus 50% for everything else. We'll give it to you for $4 an hour. And we'll have somebody on site who's maintaining them for you and you'll have 100 robots here sorting packages for $4 an hour. How does that sound?

• 40:47Speaker 01

  Yeah.

• 40:47Jason Calacanis?

  And they say, great. $4 an hour times 8,000 hours a year. Four times eight, boom, it's gonna cost twenty, thirty, forty thousand dollars a year to have these maintained and ready to go. But then when it goes to consumers, you could really abstract it like a lease, you know, so you'll just pay a two hundred ninety nine dollar a month lease, and that gives you five hundred hours of your robot's time. If you go over, it's a dollar extra. Like you lease a car.

• 41:13Speaker 01

  Right.

• 41:14Jason Calacanis?

  And you go over a certain mileage, you pay fifty cents a mile. That will be a really good model for these eventually, and then there are going to be all kinds of applications.

• 41:22Speaker 01

  Great acronym, too. ASS, automatons as a service. It's gonna be great.

• 41:26Jason Calacanis?

  Or ton of toms as a service.

• 41:28Speaker 01

  Ass, yes, would be your acronym, yeah.

• 41:29Jason Calacanis?

  They'll cover your ass, yeah. I think they're gonna be great. I mean, we had a Security One night scope that had been at like TechCrunch fifty or one of the early launch festivals, one of the early ones. That was that weird looking robot that just drove around.

• 41:42Speaker 01

  Sure.

• 41:43Jason Calacanis?

  Now there's many of those security robots, and I think they were taking the same approach, which is security guards, twenty dollars an hour for them to pay, play Candy Crush and fall asleep. This thing never falls asleep, works twenty four hours, and it's ten dollars an hour. And like even if it was the same price, it does a better job because it never stops walking around. It's got three hundred sixty degree cameras recording everything, which a human's not capable of.

• 42:04Speaker 01

  Accidentally shoot as many people, probably, hopefully, as the human security guard.

• 42:09Jason Calacanis?

  But good luck with your hardware startup. It's good timing.

• 42:11Speaker 01

  Yeah. All right, we got a question from Jacob. We got a very spicy question that you're free to punt. Or we can react to some videos. What's your, what's your pleasure?

• 42:20Jason Calacanis?

  Give me the spicy and then we'll do a video reaction.

• 42:22Speaker 01

  From Sean Sully, AKA Arugel on X. Out of all the people in Silicon Valley, who's the one person you really don't like the most and why?

• 42:32Jason Calacanis?

  Who don't I like?

• 42:33Speaker 01

  Yeah, the one person you don't like. I think you could pick your reason. You disagree with them on things, it's a personality conflict, whichever.

• 42:40Jason Calacanis?

  Yeah.

• 42:41Speaker 01

  You take your pick. I have some, I have some guesses, but I'd like to hear your pick.

• 42:45Jason Calacanis?

  Well, listen, I, I would say.

• 42:49Jason Calacanis?

  You know, we all operate in the same ecosystem of users. And some people, I think, have damaged the reputation of the industry and the user base. And then some people have just maybe screwed over friends of mine. So like Zuckerberg, I've been a consistent critic of.

• 43:10Speaker 01

  My number one guess.

• 43:13Jason Calacanis?

  It's not personal. It's that every time he had a chance to do the right thing for humanity, he picked his own self-interest over that of humanity. Whether it's teenage girls and like, or people's privacy, or how he worked with partners in his partner program and treated founders. Every single time, he seemed to make a decision that was not in the best interest of humans. That's it. And so I don't like the way he's behaved. It's not personal.

• 43:44Speaker 01

  Right.

• 43:45Jason Calacanis?

  Like I don't, I haven't seen Zuckerberg in person in a decade. I mean, I might've been at a dinner and been in the same room as him, I'm sure, a couple of times. But having sat down and had a conversation with him, I'd be happy to do that. I'd be happy to interview him for a project or a product. But I think he is so obsessed with the growth of his companies, which has made him tremendously successful, that copying other people's ideas blatantly, screwing partners over in the partner program he had, not being thoughtful about teenagers using his product, not being thoughtful about, you know, all the reports that he had internally about teenagers and specifically teenage girls, and how damaging Instagram was for them in terms of eating disorders and anxiety.

• 44:29Jason Calacanis?

  And then optimizing all these platforms to keep you online is, it's just, it's a level of selfishness in decision-making that, and cutthroatness that I under. Understand, but that, you know, um, I wouldn't do. And I think has damaged the reputation of the tech industry. I think he actually has made people look at the tech industry and be like, ugh, you know?

• 44:53Speaker 01

  Well, I mean, we've seen that.

• 44:54Jason Calacanis?

  Sam Altman, I don't like because he screwed Elon and Elon's my friend and I watched it happen. But I, I kinda liked Sam, or I did like Sam interpersonally. We always had some like interesting things, but he, um, you know, he kinda shivved my friend and I'm team Elon. Not cool to what he did to him. Um, and listen, I'm not the only person who thinks like, hey, maybe Sam should not behave this way on a business level. But again, it doesn't matter in business. You can be incredible. The two people I'm talking about are two of the most successful people ever in the history of business.

• 45:26Speaker 01

  Yeah, they're doing all right.

• 45:28Jason Calacanis?

  So in some ways, being able to make self-interested decisions and not worry about what people think about you and not worry about losing and burning relationships is a quick path to extraordinary success.

• 45:40Speaker 01

  Yes, I think being a, being a like high level tech CEO definitely self-selects for some of those qualities that we would associate with, you know, like someone you might consider like a jerk or a not, not very nice person in your life.

• 45:52Jason Calacanis?

  I mean, the number of people who in that piece, um, in the New Yorker, which, you know, listen, I, these press pieces, like it's probably, you know, 60% true, 40% true, 80% true, who knows? And then people have agendas, so you have to sort that out. And the press doesn't care about sorting out the agendas. They care about like, hey, is this piece gonna rip or not, right? So I don't, the, the New Yorker piece on Sam was brutal. And a number of people called his behavior sociopathic. I, I didn't call his behavior sociopathic. That's what, you know, uh, Ronan Farrow and his collaborator, I didn't participate in that piece. They asked me to, I was like, you know, I, I don't really have any business interest with Sam. So like, I'm not qualified.

• 46:36Jason Calacanis?

  And then number two, I don't talk to the press, so I'm good, thanks. Um, but they were like, we had specific questions to ask you about Sam Altman and about the Sequoia Scouts program. I was like, yeah, feel free to put them in writing and I'll consider. And they're like, we don't do that. And I was like, just, I just didn't respond, right? I don't care. You know, I just was interested in what the. Questions were, I probably wasn't going to answer them anyway, but I was curious like what the question even was.

• 46:59Speaker 01

  Yeah.

• 47:01Jason Calacanis?

  Yeah.

• 47:01Speaker 01

  I mean, when you're writing a piece.

• 47:02Jason Calacanis?

  So anyway, that's the answer.

• 47:04Speaker 01

  There you go. Fair enough.

• 47:05Jason Calacanis?

  I think. And it's not personal. Like, so I, you know, everybody wants to make it personal. Like, I'll bring up maybe the guy with the rock, the guy in military tech, you know, like when I made, when I popped off on my answer about him. It's not that I dislike him. I just thought what he did was brain dead, like stupid, like to do covert stuff. Now, is the press story correct or not? I don't know if that press story was correct. And I did kind of pop off and I apologized to him because like, yeah, I looked back on it. I was like, yeah, you know, maybe I was a little bit too hardcore in my answer. But if that story was true, I do think he did the wrong thing, but I didn't have to say it as brutally as I said it. And I did kick him when he was down. He got fired. I was kicking him. So I kind of looked at it and I was like, yeah, maybe, maybe that was not a classy or kind or Christian thing for me to do.

• 47:50Jason Calacanis?

  So I was like, yeah, okay, I take ownership of that. Sure. I kicked the guy when he was down.

• 47:53Speaker 01

  When you podcast every day.

• 47:54Jason Calacanis?

  Probably shouldn't have done that.

• 47:55Speaker 01

  When you podcast every single day, you're just reacting, you're doing hot takes. It can, you get caught up in the moment. I think.

• 48:00Jason Calacanis?

  Well, but you see how I do it? Like we were doing a recording before this and people were asking me about a case and, you know, oh, Y Combinator and general catalyst supporting a founder who allegedly did things that were unethical and copied another startup. And I went like, I framed it like, if this is true, and we don't know if it's true, this would be maybe unethical, but not illegal behavior. And maybe, you know, general catalyst didn't know what this founder was doing. If it's even true, and maybe they're trying to clean it up right now. So I really think through like, before I pop off and I just don't trust the media or any report now. And when you hear me on All In, you know, sometimes people just run with a Kane Koehl, the great story or like some viral clip.

• 48:42Jason Calacanis?

  And I'm like, just so we know, that viral clip could be AI, it could be an old clip, nobody. Knows, so this is alleged, and I kind of make a joke about it. Allegedly, perhaps, not confirmed. I put all those disclaimers on it because I'm old enough now to know like, like, I don't know, some non-zero, like, low double-digit percentages of the time I'm reporting on a news story, it's not exactly accurate.

• 49:06Speaker 01

  I think that's a good lesson for even if you're not hosting a podcast, even just in your everyday life. In 2026, you gotta take that beat. It might be very satisfying to be like, oh, this, this idea, this story, lines up with my personal biases. I can't wait to share it and prove how right I've been. Uh, you always have to take that extra beat, like, is this AI? Is this true? Is there a community note? Is there some additional information? Is this being framed in a certain way designed to provoke reaction? Because everything is.

• 49:34Jason Calacanis?

  Lon, this was your first trip to Italy?

• 49:36Speaker 01

  This was my first time ever in Italy. Yes, that's true.

• 49:38Jason Calacanis?

  Okay, so, we'll just... Oh, you didn't went to Greece as well?

• 49:43Speaker 01

  I went Santorini and Mykonos. I visited Santorini and Mykonos.

• 49:46Jason Calacanis?

  Amazing!

• 49:46Speaker 01

  It was amazing.

• 49:47Jason Calacanis?

  So, give me your general impression of Greece and Italy. What were your favorite parts of it? What was extraordinary? And then what was underwhelming and didn't hit the notes as we go off-duty here?

• 49:58Speaker 01

  Yeah, so I went...

• 49:59Jason Calacanis?

  This is Lon off-duty in Italy.

• 50:00Speaker 01

  I went, I did a week in, in Rome. Uh, me and a friend, we stayed in an Airbnb right by the, uh, Castel St. Angelo. Uh, right, right, it's sort of the middle of the city, right? You know, not far from Tristevere. The, staying in the Airbnb was amazing. We're wa- walking distance from the Vatican. It's a building from the 1600s where the Pope's staff used to live in, like, the Renaissance era. So it was an unbelievable place. The best thing we did, uh, was that crypt tour. We did a golf cart crypt tour and a guy took us to all sorts of, like, out-of-the-way, you know, sort of, like, churches that had, you know, bone temples in the basement and all of this crazy art. Uh, that was amazing to see.

• 50:41Speaker 01

  We took a, a bullet train one day to Florence and with, to the Afezi Gallery. We went to this amazing pasta restaurant called, uh, Osteria Pastella, uh, that was...

• 50:52Jason Calacanis?

  I think I went to both of those. That's great.

• 50:53Speaker 01

  Yeah, they, they, uh, they're one of the places, they, they take a huge wheel of cheese and they pour... Brandy in it and then they light it on fire and then they mix your pasta in the cheese bowl and then they topped it with white truffles. It was incredible. And the Uffizi, you know, lots of great art. I will say a down thing. It's very, very crowded right now in Italy. Lots and lots of tourists want to see Roman Florence. I was not alone. And one thing that really bugged me in all the art museums that we went to is people are standing in front of the paintings of the sculptures and they're just snapping photos on their phone. And I mean, this is like Botticelli's Birth of Venus, Caravaggio's Medusa. Just go on Google Images. There's a hundred beautiful, up-close, high-resolution photos of every...

• 51:38Speaker 01

  You could get the Birth of Venus on like a mouse pad. Like, you don't need your own photo.

• 51:44Jason Calacanis?

  I think this is a gripe. This is a gripe that's worth noting.

• 51:48Speaker 01

  Yeah.

• 51:49Jason Calacanis?

  And just be in the moment, folks. Just be in the moment. And I'll tell you the thing that makes me crazy in these places. The selfie stick.

• 51:57Speaker 01

  That...

• 51:57Jason Calacanis?

  Or the I360 guy. You know the I360 guy with the stick?

• 52:03Speaker 01

  They're all...

• 52:03Jason Calacanis?

  And it goes up?

• 52:04Speaker 01

  Yeah.

• 52:05Jason Calacanis?

  And he's got to walk around and he's got to have a 360 view that he's never going to look at. But the 360 guy is worse than the selfie guy.

• 52:13Speaker 01

  Yeah.

• 52:14Jason Calacanis?

  The selfie guy's got his iPhone on the stick, whatever. These guys are walking through Vegas casinos and I'm like, what are you documenting? Your life is incredibly boring. You're the least important person within 100 miles of this place. This place has been documented, as you correctly point out, to the point of absurdity. And now everybody's got to be on your I360 and you're smacking people in the head. Nobody cares. You're never looking at these things. If you want to take a quick photo of yourself in front of your favorite piece, totally fine.

• 52:44Speaker 01

  Right. And I did. I posted a few of them to Twitter. I would take a picture. I'd be like, so like, here I am. I'm in the Uffizi. I want to remember this moment. I'm not saying don't be a tourist, don't take a photo, don't take a selfie, but it's that stare. Just taking it. And like, we went to a Rothko exhibit as well in Florence, like a modern museum. And it's like, those paintings, it's being in the room with it. That's the point. It's overwhelming when you're standing in front of it. You're not going to appreciate it on your phone. What are you doing? So that...

• 53:12Jason Calacanis?

  Here's my idea. Here's my idea for these museums.

• 53:17Jason Calacanis?

  24 hours and increase the price to go. A little bit.

• 53:22Speaker 01

  Yeah.

• 53:22Jason Calacanis?

  So, or maybe like on the off hours, you pay a premium.

• 53:26Speaker 01

  Oh, sure.

• 53:27Jason Calacanis?

  I would like, because these all close at 6 o'clock, right? They're done.

• 53:30Speaker 01

  Yeah, it's like Uffizi, I think is, yeah, it's like 10 a.m. to like 4:30, but you have to get a time. They, they send you through in shifts. So when you buy your tickets, they give you a time to show up and then you get in the line.

• 53:41Jason Calacanis?

  And there's like a VIP line. You pay an extra couple of euros. So what did you pay, 10 euros or something? It's not expensive.

• 53:47Speaker 01

  No, it was, I think it was like 30 euros a piece, but we also made those plans a little last minute. I bet if we got in earlier, we probably could have gotten a cheaper Uffizi.

• 53:55Jason Calacanis?

  Here's my idea.

• 53:56Speaker 01

  Yeah.

• 53:57Jason Calacanis?

  The place closes, like the last entrance is 4:30, which means they're kicking you out at 6.

• 54:01Speaker 01

  Right.

• 54:02Jason Calacanis?

  6 to 8, 8 to 10, 10 to 12, 12 to 2, 6 a.m. to 8 a.m. I know maybe people don't want to work those. Have a 100 euro experience. Now, 100 euro, 100 dollar experience per person, sounds insane, but by the way, if you're an Uber driver or you're a housekeeper in New York, you're making 30, 40, 50 bucks an hour already.

• 54:29Speaker 01

  Yeah.

• 54:30Jason Calacanis?

  And that person might want to have an experience with 10% as many people there or 20% as many people there.

• 54:35Speaker 01

  It would be a totally different experience to go and really like soak it in on your own and have the time. Instead of being pushed around and everybody's trying to push you.

• 54:44Jason Calacanis?

  I would have loved, loved to go to dinner. And then I like to do my after dinner walk, because I'm old and I'm, you know, controlling my weight. road.co/twist.

• 54:56Jason Calacanis?

  I would love to do my two hour walk in the Louvre from, you know, 8 to 10 p.m. or even 10 to midnight. How great would it be for us to be in the Louvre at 11 p.m.

• 55:08Speaker 01

  Yeah.

• 55:08Jason Calacanis?

  And see the Mona Lisa or the Venus de Milo with Bud, a half dozen people there.

• 55:14Speaker 01

  Yeah, because also I had, yeah, like in the British Museum too in London, I had the same experience where it's like, it's great, amazing to see that stuff. But you're, you're constantly in like this huge crowd and everybody wants to take their photos and it's really.

• 55:25Jason Calacanis?

  Did you go to the Florence gelato place that I told you about?

• 55:29Speaker 01

  You know, I did, I went to a gelato place in Florence, but we were only there for 24 hours. I ran at a time. I did not get to, I missed that. I missed that one. But I did, uh, we did go, we got some incredible food, the whole, I roamed too. We went to some really amazing restaurants. And then, uh, so that was week one. And then week two, we joined, uh, my dad and my uncle and his girlfriend Karen, uh, for a cruise. And that went to Santorini, Greece, Mykonos, Greece, and also a town named Kushtadashi in Turkey, where there, there's the ancient Greek ruins of Ephesus are there. And so we, we did a little quick tour of that.

• 56:03Jason Calacanis?

  Santorini, beautiful, right? On that hillside with the, yeah. Did you get to go on the donkey ride?

• 56:09Speaker 01

  No.

• 56:09Jason Calacanis?

  Up and down this everything?

• 56:10Speaker 01

  I felt, I felt bad for the donkey. I didn't, I don't, I don't want to subject a donkey to my 200 pounds. I felt like, I'm not going to do that to that poor.

• 56:19Jason Calacanis?

  Well, this is why road dot co slash twist will get you down to 180 and you'll be fighting what you're gonna. No, I thought the donkey thing was a little bit extreme too, but they have like this very steep hills.

• 56:28Speaker 01

  It leads up, you're right.

• 56:29Jason Calacanis?

  You take a donkey ride up it.

• 56:31Speaker 01

  Oya, the, the sort of, that, that, it's the city when you think of Santorini and you see the Instagram posts with the white houses and the blue dome churches. That's Oya. And so we got to go check out the town. We, we took a bus, uh, to get there. And then we went to Fira as well, another town. And then we, they, they took us to one of those black sand beaches. So we got to do a little beach tour. And Santorini was incredible. That was, that was.

• 56:52Jason Calacanis?

  Well, I'm glad you got to take some time off.

• 56:54Speaker 01

  Me too.

• 56:54Jason Calacanis?

  And, uh, this is where I don't have a problem with the meta glasses, actually. I'm okay.

• 56:59Speaker 01

  Sure.

• 56:59Jason Calacanis?

  I have an exception for meta glasses. If you take them to dinner. You're not invited to dinner.

• 57:05Speaker 01

  Right.

• 57:06Jason Calacanis?

  However, if you're in a museum and you want to put those on and record.

• 57:11Speaker 01

  Go for it.

• 57:11Jason Calacanis?

  Go for it. It's better than the selfie stick everywhere.

• 57:14Speaker 01

  I don't think, I still don't think you're really gonna get a lot out of that after the fact that part of being in the museum is you're that, you're in the museum. It's, it's, it's real. Like, you can look up art on the internet all the time. I do it all the time.

• 57:27Jason Calacanis?

  Take 10 pictures. Okay, take 10 pictures.

• 57:29Speaker 01

  Yeah, yourself at the front, yourself in front of your favorite piece of art that you saw. Okay.

• 57:34Jason Calacanis?

  At the cafe, having a coffee and whatever.

• 57:37Speaker 01

  Anti-selfie, I took a ton, but like, it, it, it, when you're standing in front of a Rothko, you don't need to have your camera. It, it, it's just, it's just.

• 57:45Jason Calacanis?

  What are we doing, folks?

• 57:45Speaker 01

  It's just lines on a canvas on a photo. You have to stand there and soak it in.

• 57:50Jason Calacanis?

  Yeah. All right, everybody. It's been another great twist is in the can. Bye-bye.