Level up your copywriting w/ Sam Parr | E2226

This Week In Startups is made possible by: Luma AI - https://lumalabs.ai/twist Northwest Registered Agent - https://www.northwestregisteredagent.com/twist Lemon IO - https://lemon.io/twist Today's show: DID YOU KNOW… most of the tried and true techniques devised by marketing gurus in the '40s and '50s still apply today? On TWiST, we're joined by online marketing expert Sam Parr, host of "My First Million" and founder of Hampton. He's sharing all of his top tips and tricks for making your writing more compelling, and converting your readers into new customers. In this essential pod for any and all founders, hear Jason and Sam run down their list of the best-ever marketing books, why there's no such this as "too long" only "too uninteresting," when to use AI and when to rely on your own brain, why you're the average of your five best friends, and lots more deep insights. Timestamps: (00:00) Sam Parr of The Hustle, Hampton, and My First Million is here to teach us how to become better copywriters (03:59) How Sam got interested in the (then-shady) world of internet marketing (06:26) Why Sam recommended THESE advertising books to Jason (08:15) All the principles that ad execs developed in the '50s still work! (09:43) Glengarry had it right; the magic of A. I. D. A. (11:19) Luma AI - Stop guessing and start directing with Ray3 Modify from Luma AI, the AI-powered post production tool. Explore it at: https://lumalabs.ai/twist (14:30) There's no such thing as "too long," just "too uninteresting" (16:15) The goal is to write at a 4th grade reading level (18:12) Why Sam only uses AI for "The Big Idea," not the actual writing (19:37) Why you're the average of your five best friends (21:14) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today! (22:15) Using AI to dig in and research, to make your writing more interesting (23:42) CopyWork: The technique that helped Sam fine tune his writing (28:41) Avoiding "The Feature Death March" (30:56) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist (32:00) Words are better than images, but videos are better than anything (34:43) Why stories make such a huge impact (37:36) Sam and Jason are both obsessed with the book "How to Be Rich" (43:02) First World Problems are still problems!! (44:31) Why Sam launched Hampton and what it takes to get in (47:10) Why scaling a community is so much harder than launching (51:04) The lessons founders can take from Ted Turner (58:36) What Jason likes best about My First Million (1:00:28) It's never too early to get your first $10 million (1:04:07) How accurately did Producer Claude guess what Sam was going to teach us? * Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com/ Check out the TWIST500: https://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/ * Thank you to our partners: (11:19) Luma AI - Stop guessing and start directing with Ray3 Modify from Luma AI, the AI-powered post production tool. Explore it at: https://lumalabs.ai/twist (21:14) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today! (30:56) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist

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

• 0:00Speaker 00

  Like I wasn't selling anything particularly special. And so I started like Googling how to be a salesperson. And I learned about this thing called copywriting. And what I realized was if I could take my ability to sell one to one, which I eventually learned how to do and put it on paper, you could sell one to an infinite number. There was a guy named David D'Angelo. He would write these like 5,000 word emails where it's just plain text. And they were making $30 million a year selling eBooks on how to like hook up with the girl.

• 0:25Speaker 01

  What percentage of the lessons persist and kind of hold true in the current moment?

• 0:29Speaker 00

  All. So basically there's a lot of sales pages that you go to and it's just tons and tons of words. You're going to say, that doesn't work on me. That used to work then, it doesn't work nowadays. And you're going to like see like cheesy headlines and all that stuff. You're going to think none of that works on me. You're wrong. It does. Long form copy typically is almost always better than short form copy. Anyone who sells a lot of anything knows all these principles. And one of the principles is that long form is better than short form. And a lot of people listening, they're not going to believe it, but they're wrong.

• 0:55Speaker 01

  This week in startups is brought to you by lemon.io. Building a great team is essential to any business. Lemon is a marketplace of vetted, experienced developers ready to take your company to the next level. Get 15% off your first four weeks of developer time at lemon.io/twist. Northwest Registered Agent. Starting your business should be simple. With Northwest Registered Agent, you can form your entire business identity in just 10 clicks in 10 minutes. From LLCs to trademarks, domains to custom websites, they've got you covered. Get more privacy, more options, and more done. Visit northwestregisteredagent.com/twist today. And Luma AI.

• 1:37Speaker 01

  Stop guessing and start directing with Ray 3 Modify from Luma AI, the AI-powered post-production tool. Explore it at lumalabs.ai/twist.

• 1:49Jason Calacanis?

  All right, everybody, welcome back to This Week in Startups. Alex, as part of our continuing focus on helping founders build better startups, I was faced with a bunch of founders asking me how to write better copy. Cause I was looking at their webpages and I was like, my God, this copy sucks. And then I looked at some of our own webpages and said, my God, this copy sucks. And I was like, who's really good at this? And then I remembered my friend Sam Parr from the Hustle, Hustle Conference, Hustle Newsletter, My First Million, had obsessed about this. And I started doing some ChatGPT research, some Claude research, you know, perplexity searches, and Sam came up. So he's well indexed on

• 2:34Jason Calacanis?

  this topic. And I started buying all the books that he recommends, all these books by old advertising copywriters. And that's going to be my winter reading. So it's always great when you can draft off of somebody who's done the work. So with that, why don't you invite our guest on board, Alex?

• 2:50Speaker 01

  Guys, we have Sam Parr on the show today. As Jason mentioned, he was the founder of The Hustle, sold that to HubSpot back in 2021. Currently, he's working on Hampton, a members only community for founders focused on small group problem solving and local mutual support. He's also on the My First Million podcast and does Money Wise, the show for if you have money and you don't want to lose it. We love him. Sam, welcome to the show.

• 3:13Speaker 00

  What's up, guys? Jason, are you gonna read the books? Which ones you get?

• 3:16Jason Calacanis?

  Gosh, you know, you mentioned like three or four of these books by these old advertising heads, and I bought all of them. So what I was doing was I just took three or four of your podcasts where you talked about copywriting. I took those, I put them into Claude to grab the transcripts and just give me all the bullet points and all of his advice and then what he's reading and his sources. He gave me all the sources. And then I just opened up Amazon and I just bought them all. Some of them were out of print or a little hard to get. But I guess that's a good place to start, which is, how did you become, and I want to talk all about Hampton, too. But let's start with copywriting, because

• 3:58Jason Calacanis?

  founders need to do that. How did you become obsessed with copywriting and why?

• 4:02Speaker 00

  So I used to work, I used to own a hot dog stand in college. That's how I made, paid my way through college. And I had a hot dog stand, I called it Southern Sam's wiener's as big as a baby's arm. And I would like sell, you know, that's called copywriting.

• 4:17Jason Calacanis?

  That's copyright. You gotta laugh at him.

• 4:20Speaker 00

  Like, I wasn't selling anything particularly special. And so I started like Googling, this was back in like 10, 2010, like how to be a salesperson. And I learned about this thing called copywriting. And what I realized was if I could take my ability to sell one to one, which I eventually learned how to do, and put it on paper, You could sell one to an infinite number. And so I started reading and a bunch of bloggers and I actually got really interested in the world of internet marketing, which back then was very shady. And there was these guys that would write these books that would teach young men like myself, who weren't particularly good with women, basically how to pick up girls. And a lot of it was very shady and weird. The PUA movement, yeah. Yeah, but, but it was so successful in terms of a business. And you had guys, I don't know if you remember this,

• 5:02Speaker 00

  there was a guy named David D'Angelo. He would write these like 5,000 word emails where it's just plain text. And they were making $30 million a year selling eBooks on how to like hook up with a girl. And that is when I got interested in copywriting, where I got interested in like the dark arts a little bit of copywriting. And I was like, okay, how do I master this? And then let's actually use it to sell stuff that I, that I love. And so that's how I originally got into copywriting.

• 5:24Jason Calacanis?

  It's really interesting that the, the smarmy people, people on the fringes, they are typically doing these nefarious things. So they have a really, and so do spammers and hackers. They will sometimes be the best at exploiting the hacks. And I think that's what you recognized. I remember when I wrote my book on angel investing, a bunch of these same type of people who went from like coaching on how to do dating and writing these never ending pages, started doing ones on angel investing and they had cribbed a lot of my copy from my book. And they were talking about, oh, if you made the Uber investment, you made 2,000 X, 5,000 X if you did this investment.

• 6:06Jason Calacanis?

  And I was like, oh my God, these guys have out marketed me and I wrote the goddamn book.

• 6:11Speaker 00

  They're animals.

• 6:11Jason Calacanis?

  They're beasts. They're in beast mode. They're relentless about it. I hate these guys.

• 6:15Speaker 00

  I was gonna say, they stole your stuff.

• 6:17Jason Calacanis?

  No, no, it's just annoying, but they do understand something. Yeah, there's something to learn from there. So when I saw you had, you know, done all this stuff, I immediately bought this book, Ogilvy on Advertising.

• 6:28Speaker 00

  You'll love it.

• 6:28Jason Calacanis?

  And then Confessions of an Advertising Man. These are the two I bought.

• 6:33Speaker 00

  And then type in Joe Sugarman on Amazon and buy his Adweek Guide to Copywriting.

• 6:37Jason Calacanis?

  Ah.

• 6:38Speaker 01

  Okay.

• 6:39Speaker 00

  That one's probably above everything, my favorite. That one was out of print, but I'll send you a link where you can get it for cheap. But so here's how it works. So like in the 1930s, 40s, 50s, before the internet existed, you had these guys like David Ogilvy. And they basically wanted to sell, let's say, a vacuum to a housewife. Well, how did on earth did they do that? Well, some of them would go door to door or buy radio commercials. But a lot of them, what they did was they would do these services where you could send a letter to a million housewives in America. And that basically meant you had to send pieces of paper with typewriter writing. And you had to use words so good that you had to make your money back because it was incredibly expensive to do this. And so they got incredibly good at figuring out what words convince people to buy and take action and do stuff.

• 7:24Speaker 00

  And so I love learning from those guys from the 50s all the way up to the 90s, like pre-internet era guys. Those are the best places to learn from. And David, David Ogilvy is one of those. You saw Ogilvy Mather, that was a multi tens of billions of dollar ad firm now. And they're glamorous. They do all, you know, probably Ford or Ferrari, all this fancy stuff. But he started as a copywriter, kind of a, like, he would write these, like, just, they called them sales letters. These letters that they would mail to people to sell anything.

• 7:49Speaker 01

  I'm just really curious, when we go back in time to these kind of early titans of copyrighting and advertising, what percentage of the lessons persist and kind of hold true in the current moment? Because

• 7:59Speaker 00

  All.

• 7:59Speaker 01

  Really?

• 8:00Speaker 00

  Everyone says the same thing. So here's what people listening to this, you guys are going to think a couple of things. You're going to think a few things. You're going to think ads don't work on me. Obviously, that's nonsense, right? The, you're going to see long form copy. So basically, there's a lot of sales pages that you go to, and it's just tons and tons of words. You're going to say, that doesn't work on me. That used to work then, it doesn't work nowadays. And you're going to like, see like cheesy headlines and all that stuff. You're going to think, none of that works on me. You're wrong. It does. We could go through examples, but you just had Amazon, like, for example, long form copy typically is almost always better than short form copy. You just were, Jason, on amazon.com, the most well-known website potentially in the world. And if you were to look at that book that you just had up and you were to see all the words that were on there, as well as all the photos, as well as all the reviews, there's probably 10,000 reviews.

• 8:43Speaker 00

  That was probably tens of thousands of words on there. If you go to apple.com and you look at how much an iPhone Phone call. So you want to buy an iPhone, it's going to have a photo, a photo is worth a thousand words, tons of photos and tons of words is going to be a really long page. Anyone who sells a lot of anything knows all these principles. And one of the principles is that long form is better than short form. And a lot of people listening, they're not going to believe it, but they're wrong.

• 9:04Jason Calacanis?

  So the never ending webpage that we experience from the cheesy marketers all the way to the most elite marketers like Apple. That works for a reason. What's your best guess as why long works over short? Because intuitively you might be like, hey, TLDR concise is better. Why does long in your estimation and your experience work better than short?

• 9:27Speaker 00

  The ad week, this is one of my favorite books.

• 9:29Jason Calacanis?

  Just ordered it.

• 9:30Speaker 00

  And this looks like a not a interesting like title or, you know, it's like a long, it doesn't follow any of the rules, but I'm telling you this is the best book. So why does long work better? Well, it does for a couple of reasons. One, when people skim, you need different areas to grab their attention and get them to come back down. But it's all rooted in this thing called the slippery slope. So in order to sell anything, I want you to fall down this slippery slope where you start where you're interested. You get a little bit more desire and finally I get you to take action. So it's called Ada, attention, interest, desire, action. I need to grab your attention. I need to keep you interested. I gotta make you desire what I want you to desire. And then I have to make you take action by being very specifically telling you what to do for the next step. It's not necessarily that long is better than short. It's that you want the least amount of words to be the most effective.

• 10:13Speaker 00

  And oftentimes you need a lot of words to be incredibly effective. And for a person who's going to buy your product, the goal of good copy is to make me the writer or the marketer. Write to you in such a way that it feels like I know what you were thinking better than you do. And I know your problem so intimately that I must have a solution because no one else has been inside of your head as good as I have right now. Therefore you feel the way I feel you could guide me out of this, out of this pain. So let me give you an example. If you were selling, I'll, I'll do a weight loss thing because that's typically like kind of scammy. But let's say like, if I was writing a weight loss ad for women, I would say like, I know why you stand on the edge of your friends. When you take a photograph with your buddies at the beach. I know why you wear that cover up. I know that you offer to take the photo.

• 10:58Speaker 00

  I know why you do that. And you like go into like the shame that someone feels. And these are things that she has probably never said to herself. But if I write in such an intimate way. You start to think, I know you. Now, of course, you want to use this power for good, not for bad, but I'm just giving you an example. And so Long does a better job of getting you to fall down this slippery slope where you are just ready to buy at the end.

• 11:19Jason Calacanis?

  We're AI first here at launch, and I have a team try out every cool new app and tool just to keep track of what's the state of the art, what's possible. And we found the closest thing on the market to a real AI-powered post-production tool. It's called Ray3 Modify from Luma AI. And with most AI video apps, you're just plugging in words and you're hoping for the best. But with Ray3 Modify, you build on top of Luma's Ray3 model. This gives you precise nuanced control over your outputs, allowing you to actually direct your AI videos, not just guests. So let's check out some examples. We animated the launch logo, keeping its recognizable font and lettering intact. Oh my God, this came out incredible. Here you have producer Oliver going from just pretending to surf

• 12:04Jason Calacanis?

  to having an actual surfing video. This stuff is wild. And we can drop this Tesla into about any environment we want. Stop guessing and start directing your videos with Ray3 Modify from our friends at Luma AI. Try it today at lumalabs.ai/twist or via the QR code you see on the screen right now.

• 12:29Jason Calacanis?

  And that's going to get your attention big time because it's, yeah, and it also triggers a bunch of emotion. So emotion is part of this as well, but that gets your attention for sure. Now, interest and then decision. Unpack those for us as we go down the slope.

• 12:46Speaker 00

  So let me give you an example. Let's say that I want to convince you to drink water. I'm going to make up a bunch of facts, so don't hold me to the end of facts. I would say, have you ever seen those big muscular guys at the gym carrying around gallons of jugs of water?

• 12:57Jason Calacanis?

  Yeah, I have seen those.

• 12:58Speaker 00

  The reason they're doing that is because it actually makes them build muscle 30% more than if they weren't going to do that. You see, the thing about water is it helps carry amino acids, which are essentials to building proteins in your body. And so if you don't drink enough water, you're just not going to build enough muscle. And that's why these guys who are all big and Jack looking, that's why they always Carry these jugs of water. So that was my, that was my desire, my interest and desire was making it. And then my action is like, so if you want to get bigger muscles, here's what you need to do. Every day before you go to the gym, fill up this gallon of water and drink all of it before noon. That's how it works. And so you, you take that format of attention, interest, desire, action, and you could apply that frankly, to anything, and that will get you 90% of the way there. You see this on Instagram. If you scroll through Instagram, every Instagram influencer talks about

• 13:42Speaker 00

  a hook. The hook is the first five sentences that grabs your attention. They call it a hook, and then they call it a meet, and then they call it a CTA. So hook, meet, CTA. But it's all the same verbiage. But young kids, that's what they say. If you ever follow, just follow one person on Instagram who gives advice on how to get popular on Instagram, they're gonna say hook, meet, CTA. It's the same thing as attention, interest, desire, action.

• 14:01Speaker 01

  I'm just thinking about the idea of having kind of like more words to get people through that funnel, down that slippery slope, and how that kind of intersects with digital media. Because when I think of people that are making a lot of noise today, that are theoretically connecting with their copywriting, I'm thinking about places like X, which are inherently short forms, Sam, or at least kind of used to be. So how do you take the thing that worked in direct mail back in the day, and take it to a digital format world where people have a lot of what we might call TikTok brain rot? It seems to be a conversion or translation problem there.

• 14:31Speaker 00

  There's no such thing as too long. There's only such a thing as too uninteresting. Do you guys remember on Twitter, when Twitter got really popular during the pandemic, there was this joke of people called Thread Boys?

• 14:42Speaker 01

  Yes.

• 14:43Speaker 00

  That's exactly what I'm describing here. If you go on Twitter and look at what are some of the most shared tweets of all time, it's things that are longer than the norm. Because you need someone to be emotionally invested. And what's gonna happen is your funnel, maybe it's gonna be that, the goal is not to make 100% of the people to read your thing, it's to make the right 5% of the people to read your thing, and you want them to share at a 90%, rate, as opposed to a lot of normal content. You might have a lot of eyeballs, but it's not gonna make someone compelled to share. And so the thing about copywriting is all rooted in two things. One, getting what's in my brain and what's in my emotion into your brain and your heart. And the second thing is getting you to actually do something. It could be as simple as MLK giving a speech and wanting you to change your opinion on racism, or it could be, I want you to buy something. But it's all about influencing action. And there's certain words, human nature

• 15:28Speaker 00

  is human nature, it's been the same since the beginning of time. There's certain ways to actually do this.

• 15:32Jason Calacanis?

  One of the techniques that you and I share in common, when I had writers in the magazines back in the day, in the zine day, and then onto blogging. When writers had writer block and they couldn't get going, I would say, hey, why don't you just talk to me and record it? And I'll give you sort of props, prompts. And people said, yeah, you're a great writer, Jake Allen. You know, how did you get trained? And I said, well, I, well, talking to, I used to have like an actual recorder and I would talk into the recorder. And then I would transcribe what I wrote, which is really easy to do now with voice recognition. But I experimented with drag and dictate and all those things. And I would try to just say it like I was saying it to a friend. So maybe unpack, talk like, this, I think, one of your core tenets, write like you speak, right? Yeah.

• 16:14Speaker 00

  I've got four or five things that I tell people. The first is start with like the big idea. You can call it a hook or you can call it an angle. And that's basically if you were just telling your buddy about a TV show, like what happened? Oh, it's about a, like you're describing the movie Ted. It's about a talking bear who's really vulgar. I don't know, like, you know what I mean? Like, just like that one liner. The second thing is to write like you talk. Now, to be, to get very tactical, it's to write simply. And it's to write at a fourth or fifth grade reading level. There's this app called Hemingwayapp.com. It's free. And what you'll notice is that if you have to look something up in a thesaurus, don't use the word. The goal is to write at a fourth or fifth grade reading level. And I'll give you guys a really good example. Warren Buffett owns an insurance company. That's a very complicated business.

• 16:56Speaker 00

  But his annual letters, on average, I believe each sentence that he writes, it's about 18 words per sentence. And the reading level is something like a sixth grade reading level. And this is why Warren Buffett, in part, is famous, because he was world famous for saying these very like simple phrases, like, it's when the tide goes down is when you learn who, when you learn who doesn't have their swimsuit on, like these like really amazing analogies. One of the reasons why is he was a brilliant marketer and he was really good at writing simply and using analogies. And so I tell people, start with the big idea, write simply. I tell them, use the active voice, not the passive voice. I'll give you an example. The boy kicked the ball versus the ball was kicked by the boy. The second one is bad, the first one is good. Most people actually use the second one.

• 17:38Speaker 00

  So you always want the, the someone to be doing something, not something being done to them, if that makes sense. And then the last two or three things I say, always remove adverbs. Stephen King famously said, the road to hell is paved with adverbs. Don't say, don't, don't use adverbs. And then also, a lot of times, a really effective way to be a better writer is you write, like, let's say you have this big sales page for a lot of your founders. They, they might have that or a cold email or something huge that's going to be seen by millions of people. The best way to make it good is to pretend that you are just writing to one person and you really, literally write a letter to them explaining it. And that's a really good way to get out of your people's head.

• 18:13Speaker 01

  So a lot of people are using AI to write these days and it's a little bit harder to steer AI, I think, to follow the things that you're saying out there. So when people ask you how to use AI intelligently in their copywriting, do you say, don't use it at all? Or is there a way you can kind of take your principles and bring them into the AI era to have some help along the way?

• 18:29Speaker 00

  I use it to help me find the big idea, but it can never do a good job of writing. So with my company Hampton, I was making like an email convincing people why it was great, or it could be for launch, Jason, or to go to a conference, one of your conferences. So is there any like cool phrases that describe what it means to be around other ballers like you? And there was this one idea called the Michelangelo effect, where basically like you are around other smart people. And the idea that Michelangelo once said, he said, the David, the statue of David, he goes, the statue was in there, I just removed, I just removed the unnecessary stone. And the way that if I was Jason, I would say, have you guys ever heard of the Michelangelo effect? The idea is that when you're surrounded by other amazing people, you're sort of like the

• 19:14Speaker 00

  statue of David. The greatness is inside of you, but every time you meet someone great, it's just chiseling away to find that amazing statue underneath all that unnecessary nonsense. That's exactly what this conference does. So like, that is an example of an attention getting idea. Does that make sense?

• 19:29Jason Calacanis?

  It totally makes sense. And when you said it, I immediately thought of like another way to phrase it. And this is what's great about brainstorming about these things. Cause you said the Michelangelo effect. And I said, you know, you're the average of your four best friends. And so I have pretty famous best friends. And people are like, yeah, Jay Cal is really smart. And it's like, well, you're standing next to Travis, or Vlad, or Chamath, or Sax, or Elon. Yeah, you're gonna look pretty damn smart, right? Like, it is another way of saying that. And so here's like an interesting concept. Hey, you're the average of your four best friends. Come to this conference and make some new friends who are doing what you're doing as opposed to your old friends. Like your old friends might be actually, are your old friends

• 20:11Jason Calacanis?

  holding you back is probably the fear way to say it. And adding new friends. And when I tell people to come to the conferences, I say, I always hope three things for you. One, You make a new friend, like a new network and you make one or two really good lifelong friends. Number two, you learn two or three things from the content and get inspired and bring that back to your office. And number three, you enjoy the food and the vibes, like the event itself, the production of it is like, you know, interesting. So you have a good meal, you meet good people and you learn a couple of things, you'll come back next year. And even actually, I think if you get two of those three, because we've all been to a conference where we met somebody amazing, the content sucked, it was all paid for, it was like panels, the content sucked, but the networking was great and the food sucked

• 20:56Jason Calacanis?

  too, but the networking was great. I met somebody important or, you know, the people there were weird, the food sucked, it was at this terrible, you know, conference facility, but I learned like three really good things on stage, right? Like, that's always been my thing. So it's really interesting to break it down to something simple. Being a founder is a lot of work. You have to focus on your fundraising, then you gotta hire the perfect team. Oh gosh, product market fit, finding your first customers, but all of this means nothing if you're not actually a real business that's structured properly, giving your investors and clients the confidence to partner with you. At launch, we're constantly recommending Northwest Registered Agent to our founders

• 21:38Jason Calacanis?

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• 22:16Speaker 00

  So let's get even deeper. So what I would, so I use AI, that exact phrase of you're the average of the five friends. I was like, I, I've heard that before. I want to come up with a different angle. And I came up with this different angle where I was like, the headline was like, you've already heard that you're at the average of your five best friends, but I'm going to tell you something even, even more astounding, which is that there was a scientist in 1976, he studied 20,000 people and they looked at obesity rates, they look at poverty rates, they looked at happiness. And what they found was that the people who were around overweight people when they were young became overweight. The people who were around successful people when they were young, they became successful. The people who are around depressed people, they become depressed. This isn't just a cute phrase. This is actually science. We, we looked at this over, over, over 20,000, uh, 20,000 people over a decade. Now here's the good

• 23:00Speaker 00

  news for you. You can pick who you can be around. So anyway, you see how like we can like, I didn't know about that study, but I asked ChatGPT, I'm like, give me some type of evidence.

• 23:10Jason Calacanis?

  That's where these large language models have changed everything. I, I like Grammarly too. I, I, you know, what I found with Grammarly, I don't know if you use it, Hemingway is similar, obviously, but like that Grammarly follows you around because.

• 23:22Speaker 00

  It's awesome.

• 23:23Jason Calacanis?

  Yeah. People who were bad writers suddenly become good writers. People who are good writers, it can help you on the margins become great. And obviously the ideas are what matter most, but you do need to understand technically. And it does tell you when you're writing in the passive voice pretty accurately. Yeah.

• 23:37Speaker 00

  Yeah, it does. And if I, so if someone is listening to this and they actually want to get like pretty good at copywriting, here's what I think you should do. There's this idea called of copy work. Did you ever read the blog post I wrote about copy work?

• 23:48Jason Calacanis?

  Yes.

• 23:48Speaker 00

  I didn't invent this. I just stole this from, this is how we used to teach kids how to write. Like, but basically the idea is like, well, if you want to get good at playing piano, you don't just like sit a kid down and say, hey, write a song. You tell them, play Jingle Bells, play Happy Birthday. Okay. Do you like rock and roll? Let's play Green Day of Foo Fighters. You might like that. Do you like classical music? Let's play this. And then you do that for a little while and then you could like, oh, I like this piece. I like this piece. I like this piece. I can kind of mold that together to make my own bit of art. With copy work, what I like to do is I find the best sales letters, or it could even be the best book. So it could be like Catcher in the Rye. That's what I did it with. And you just sit down for a few minutes. I would do it for an hour, but you could do it for 15 minutes and you word for word, we get one of these big yellow notepads and you. Write it out word for word and you copy it word for word and that will make you just doing that act will make you a better writer. And so if you have to write something really important,

• 24:33Speaker 00

  like a sales page, you find sales page. So I love hay.com. That's a really good sales page. You write it word for word and you feel the texture of the words and that changes your brain and it changes what you do.

• 24:42Jason Calacanis?

  When you're doing, I don't know if you play chess, but in the chess.com app, they literally did this when before you play games, they say people who solve puzzles get 20% better, you know, at chess, you know, before they play games. And so it just prompts you, hey, you want to do a couple of puzzles and they'll do puzzles about the openings, puzzles about the end and they score you and it's literally that. And this is why transcribing and writing things, there's something that occurs when you're writing on a piece of paper. So at my management meeting every week, I made everybody close their laptops, especially the young people working for me, take out a Moleskine and I said, take notes and then I want you to transcribe them and tell me the three or three to five most important things that are

• 25:25Jason Calacanis?

  your takeaways from the meeting and do it immediately after the meeting. And it was like, well, I have an AI note taker, AI note takers. I feel like these things are going to just brain rot people because they're not writing it down. When you write stuff down, you process it and writing is clarity of thought. And this is what's getting lost in this generation. All these tools that they think are helping them. It's, it would be kind of like these people who put the, um, the pads on their abs and then shoot electricity in it as opposed to doing, you know, planks. It's like, just do the plank.

• 25:58Speaker 00

  Yeah, there's a reason why Jeff Bezos makes everyone write narrative formatted documents as opposed to slideshows because my opinion is that if you are a clear thinker is not always a great writer, but a great writer, a clear writer is always a clear thinker. Does that make sense?

• 26:14Jason Calacanis?

  It makes infinite sense because.

• 26:18Jason Calacanis?

  This is why that white page is so intimidating for people. It's because they actually haven't processed their ideas. When I wrote the book, Angel, it poured out of me. But then you try to write something, if you don't know anything about the subject. If I were to write about private equity, I'd be like, ah, gosh, this white page is here. I don't know anything about this. Interviewing people, that's another way to sort of hack it, right? You get to hear other people explain it and then you start processing it.

• 26:44Speaker 01

  I was just thinking about applying this kind of back to founders and kind of where they should start. I think we've done a lot of good work here, talking about different strategies and so forth. But Sam, you know, when people come to you, building a company, say, and they've done basically no writing at all. What are the first couple of steps they should do? Is it the copying function or should they be doing something else to get off the ground? I'm kind of thinking about the cold start problem for, you know, seed, series A, stage founders.

• 27:04Speaker 00

  I think they have to first be convinced why it's worthwhile to even study in the first place. I don't think a lot of people are bought in. And so I think that the best way to get bought in is probably read the book that Jason showed earlier. It was David Ogilvy, Ogilvy on Advertising. I would read that book and that would do a good job of convincing, convincing you that it's even worthwhile. I mean, I think we all agree that selling is important. We're all selling ourselves to a potential girlfriend, to a, uh, someone we want to recruit, to someone we want to raise. From Jason, I'm trying to sell them to invest in my startup. And so copyrighting is just sales on paper. And so I think that we have to convince you to do that. And the second thing, if we're going to teach a founder how to do it, I would buy those books and then I would practice. I would like literally take the book and I would write a couple of pages out of it, word for word.

• 27:49Speaker 00

  And I would do that literally, if you do that for 20 minutes a day, for 20 days, you will, you will get better. One of the great things about Twitter, I think there's a lot of bad things about it. But one of the great things about Twitter and on social media is you get instantaneous results. And so you could see is what I'm writing, does it resonating and is it compelling? And I could get, and you see habits right away when your life depends on it. And like you're embarrassed or not of it, you get results quick.

• 28:13Jason Calacanis?

  When you're selling a product or service, you know, software, let's say. And, uh, you know, I'll come up with a concept here. Tax GPT is one of our breakout startups in the recent history. They're a co-pilot. For accountants. Now, there are many features to the tax GPT product. And I think what will typically happen, I mean, I'll even pull up their webpage. It's gonna be so brutal when we do, but.

• 28:37Speaker 00

  Well, do you expect a bunch of AI tax experts to be good writers? We could help out.

• 28:41Jason Calacanis?

  Yeah, well, who knows? Maybe they did it. We'll pull it up here. But the problem I find with most folks is when you're so close to the problem, you do what's called, I call the feature death march, which is you're pitching your investors and you're like, whatever the last three features you added to the product is, you talk about those. Because that's what you just did, but you're not talking about the big grand vision. So let's talk a little bit about when you're selling a product, a software product, let's say. What is the way to lead? And what should be above the fold? What should be the hero image, the hero lead? And then we'll get into Hamilton as an example as well, because you obviously are, you know, putting your, your, your brain cycles on that.

• 29:23Speaker 00

  Above the fold should be a feeling, I think. So I'm looking at taxgpt.com. If I was them, I'm sure they've done this. I'm sure that they've talked to 50 accountants. And I'm sure that they know there's like five lines. Like when you're pitching to an investor or something, you're sort of like a comedian, testing your jokes in small rooms before you get to like the Netflix stage. And you see like, oh, that resonates. Or when I just said this, the, the customer, the accountant just kind of leaned in. And so the goal should be to tell it to like 10 or 20 people and see what caught their eye. And so if I was them, you know, I would have to research a little bit about accountants, but I would have been like, you know, that feeling on April 1st,

• 30:05Speaker 00

  or whatever tax day is like, where you're like scrambling, looking around this like you, like you know how you feel at your office where you're overstressed and you're working 20 hours a day? No more. You don't, you don't have to do that anymore. Like you, the, like I'm selling like what I, if I'm these guys, I'm selling this emotion of like, life is calmer now and, and, and not exactly what they have, which is AI tax assistant for tax professionals and businesses. So their first, their first line would be like. I haven't filed my, I mean, my accountant does my taxes. So I'd have to think about like, what stresses you about taxes? Like, like, have you ever had that feeling where you, your accountant messages you and you owe this big tax bill and you wish you had known in advance that it was actually going to come up?

• 30:46Jason Calacanis?

  Taking the terror out of tax season.

• 30:48Speaker 00

  Yes. Like, you have to intimately describe like a feeling that someone has. And it's like, we solve that by doing this, this, this, and this.

• 30:57Jason Calacanis?

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• 31:40Jason Calacanis?

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• 32:02Jason Calacanis?

  Yeah. And then talk about images and image use, because here, what we see is like a just some big copy and put your full name in to get access. And then, you know, this like weird graphic on the bottom right, AI-powered tax research memo composer. You don't see a human. What's your thoughts on what to put as an image? Have you given a lot of thought to hero images? Or are hero images the antithesis of leaning into copy?

• 32:28Speaker 00

  I think that words usually do better. A video does better than anything. A video, you know, the idea is with copy, it's just that when I say copywriting, I also mean video and audio and things like that. But copywriting is just like a way to like sell. And I would probably say that if I'm a small company, these guys, these guys are new, right?

• 32:48Jason Calacanis?

  Yeah, well, they're, yeah, they've got their series A, I think, or they're, yeah, between series B and series A, year two, basically, is how to think of it.

• 32:54Speaker 00

  There's a world where I would put, like for any small-ish company, there's a world where I would put a letter from the founder that says like, "Hey there fellow accountant, you're probably wondering what this is. Well, let me explain. You see, I used to be an accountant and I experienced this feeling all of the time. So I would probably put a letter from them right on the, I think a lot of people don't realize this, but the About Us page on any person's website is typically the second most visited website. So if you look at any About Us page, if you go to Hampton's About Us page, we tell like a story. The About Us page is like very important. I would just go ahead and put that on the front and I would put a picture of the founder and the team. There's a, like I've made this bet before with people, I think I could sell more copies of anything

• 33:36Speaker 00

  than most companies with just a Google Sheet or a Google Form and just plain text. So then, then like any website that has lots of fancy photos. And so I would lean into the personal side.

• 33:47Speaker 01

  If you take a look Jason at the Hampton About Us webpage, look at this. This is hilarious. This is my Hampton co-founder Joe. Yeah, that pulls you in. That does pull you right in and he uses the hero image to show off people. Sorry Sam, back to you. I just wanted to point this out.

• 33:59Speaker 00

  Yeah, so this is a story, this is on my About Us page. So this is, it says, "This is my Hampton co-founder Joe and this photo is from an Ink Magazine story about him and the story about how he lost a hundred million dollars. So the story goes, "My partner Joe was a very successful entrepreneur. He started a company that he sold for a hundred and fourteen million dollars at the age of 24, but then he started this new company called Little Things, which was a blog that went very viral and they scaled to seventy million dollars very fast. But then Facebook made a huge change and unfortunately this change happened right as Joe was about to sell the company for a hundred million dollars. Zuckerberg made the change to the algorithm. His revenue dropped from sixty million to ten million and the company went out of business three months later. And that photo is from an Ink Magazine story written about that experience. And that is when I met Joe and we had conversations that could help push ourselves forward.

• 34:43Speaker 00

  And that's when we had the idea for Hampton, let's do this for other people. So you see how like I-

• 34:47Speaker 01

  Yeah, you know, what this speaks to is-

• 34:50Jason Calacanis?

  In today's market, anybody can build a product, right? And building products is getting easier and easier. The intent of the founder, the intent of the artist, why did they make this startup? Why did they create this product? Why did they make this movie? Why did they make this album? Lily Allen's got this album out about her marriage breaking up, and it's doing phenomenally well. And it's because, I think, you know, she is going through what many 40-year-olds or 50-year-olds go through when they have a divorce. And it resonates because the reason she's writing it is because she's processing it, right? Whereas somebody else could just make some beats and have somebody dance, but intent matters, right? Why you made the product.

• 35:30Speaker 00

  There's a story. That matters more than anything. I mean, look at like, I don't want to use one of your nemesis, but Palmer Lucky has done a great job.

• 35:38Jason Calacanis?

  I'm a super fan of Palmer.

• 35:40Speaker 00

  Look, with Androl, I think that like, there's, I think the only reason I brought it up was in Business Insider, there was an article about like defense tech and how it's having its moment. It's like, because this guy who looks a little bit strange and says some funny, wacky stuff, like, there's a story behind it. Same way, like, one could argue, I don't know much about Palantir, but I know the founder, and I have to imagine that there's a story premium on that stock.

• 36:04Jason Calacanis?

  Yeah, I mean, if you think about the companies that get overvalued or get a value that doesn't make sense with the performance, it's typically because there's some incredible story behind it. Incredible mission is another way to say story. If you were to look at Tesla or Palantir, helping secure the future of democracy around the world, security, safety, that's a hell of a story for Palantir, like, stopping terrorism and stopping.

• 36:33Speaker 00

  It's a good story.

• 36:34Jason Calacanis?

  It's a pretty good story. And then, you know, Optimus has become this incredible story for Elon, where it's like, well, wait a second, if he could make self-driving cars, what if he makes a robot that could do anything? You know, one task is. Driving cars, but if you can figure out how to drive a car, like what things are easier than driving a car, lots of things are easier than driving a car that we do manually.

• 36:58Speaker 00

  And for all the founders listening, I think like copywriting is like one style, but like it's honestly, it's rooted in the takeaways. It's rooted in compelling storytelling and that's like the most important thing.

• 37:09Speaker 01

  That's what I wanted to ask about because I think a lot of people are technical founders who are much more, you know, familiar with code and, you know, being in the background and not talking as much, but it sounds like you don't have to actually have, uh, becoming the next, I don't know, CBS News anchor as part of your remit to do this well. So technical founders should not be afraid, Sam, of really getting into the mix here.

• 37:27Speaker 00

  No, you don't even, first of all, like it doesn't matter if you're like the nerdiest quiet guy ever, like you could be very likeable on camera for one. And for two, uh, you could do all of this via a keyboard.

• 37:39Jason Calacanis?

  You and I have a famous book in common and I heard you talk about it and I, it's so funny because I've listened to this book twice and the book is how to get rich.

• 37:47Speaker 00

  Oh, you love that one?

• 37:49Jason Calacanis?

  It's so funny because you and I have like very parallel lives. We both, I think, had an obsession at some point in our lives to be either recognized or known and to be rich. And we tried to unpack that. I don't know where your dysfunction came from. Mine came from being poor, a poor kid from Brooklyn without any power who was like, well, it'd be good to have power and money. So why don't I try to unpack how that's done? And one of the books I read early on was this one by somebody who I had met, Felix Dennis, who was a magazine publisher in tech publications and I was doing tech publications in the nineties and he had done, I think, Maxa Magazine as well. And he wrote this incredible book, How to Get Rich. And he just goes into how important it is to own equity in a brand. So

• 38:31Jason Calacanis?

  tell me about why, and he's passed away since, but the book was like, when you talk about writing in your voice, like I feel like I'm sitting with him. In a bar and we're four drinks in and he's just like, you know what? Let me just tell you the truth. And he just spills the beans on how to make money. Yeah.

• 38:50Speaker 00

  Felix Dennis, that book changed my life. It's, it's the best, it's probably the best book I've ever read because it's beautiful. I hate recommending it because the title is so vulgar, but it's a beautiful book because he's a beautiful man. And basically the idea here is that Felix Dennis, like you said, was a publisher. Here's an example of him being vulgar. In the book, he goes, I'd be worth a lot more had, had I not spent a hundred million dollars on crack and whores in the nineties. He, he was a crazy man. And he was near the end of his life when he wrote that book. He was dying of cancer and he was already rich. And he goes, I don't care about this book, so I'm just going to tell you the truth. And he laid out the importance of, or he laid out how to get rich. And it changed my life. And I actually, um, I've tried to meet some of his colleagues. So that's so cool that you met him. Was he a cool, was he a cool guy?

• 39:33Jason Calacanis?

  Yeah, he was kind of like one of these. When I was coming up in the nineties and, and you know, uh, in the late eighties, early nineties. If you wanted to be an impresario, if you wanted to be known, magazines were the format. The same way startups might be today, or podcasts might be today and startups were previously. Yeah, George magazine. Yeah, there you go.

• 39:57Speaker 00

  This is the first edition of George. Even the, the president's son even got in the magazine world.

• 40:01Jason Calacanis?

  It's hilarious, like JFK junior, who I met twice in the nineties because we were both producing magazines. I'll tell you the two stories in a minute. I said, hey, if I'm going to be important, I need to have a magazine. That's the quickest path and I created Silicon Valley Reporter. Sure enough, I wound up on 60 Minutes, Charlie Rose on the cover of the New York Times Business Section. And they wrote a New Yorker feature story about me, which if you were to say in New York City, what boxes do you want to check? Those are like four of the seven, you know? Like if you get two of those in a lifetime, you're good. If you can get four of the seven, like wow, you're, you've sort of transcended New York, uh, elite circles. But the candidness of, you know, him and this being an impresario, you wielded power as a publisher because you got to pick who was on the cover.

• 40:47Jason Calacanis?

  And Jan Wenner from Rolling Stone explained this to me. He wanted to buy my magazine and he wanted me to come work for him and do Rolling Stone like digital and spin it out as an IPO. It was really hilarious. And he looked at my covers and he said, your covers are good, but they could be great. And I said, how do you make them great? And he said, well, how much are you spending? And he taught me about how to make a gorgeous cover.

• 41:07Speaker 00

  That's awesome.

• 41:08Jason Calacanis?

  And he said, whatever you spend on the magazine, from page two to the page 100, spend the same amount of money on the cover. So if you're spending 10,000 on the writers and the photography and the illustrations inside, spend 10,000 on the cover. And I was spending like 5% on the cover. He said, people judge a book by its cover. It's all about the cover. Now, if you look at Rolling Stones, they had the most iconic covers in history, Vanity Fair, most iconic covers in history. You know, and then you can go down from there. But those were the two people who really understood it. And I met Grayden Carter when I was coming up. And he mentioned independently how much he loved the covers of Silicon Valley Reporter. So it's just ironic that that was the format. Now today, it's having a podcast, you know,

• 41:50Jason Calacanis?

  like if you have a world-class podcast, that's being an impresario. And so here I am like 25 years later, and it's just a different medium with a different thing. But you're doing podcasts too. And you started a podcast on just how to be rich. Just, and your core premise of this podcast, I believe, is what's your net worth? How'd you get it?

• 42:10Speaker 00

  In order to promote Hampton, what we noticed was that a common conversation in Hampton is my thing, my community. And like, the average company is doing like 20 million in revenue, which means there's a lot of people there who are asking money questions about their own personal stuff. Like, it can be boring, like how to set up an estate. But I noticed that those were the most popular threads in our community. And I said, what if I got ultra-high net worth people to reveal their personal income, personal expenses, and their portfolio allocation? And at first, I got people to do it. I convinced people to do it, but they did it anonymously. And then eventually, people were like, oh, fuck, I'll do that for sure. And so like, one of the first ones was this lady named Ann who sold a company called Solid Core for $250 million. And she pulled up her net worth sheet and she goes, yeah, so I got $94 million. I got this here. And

• 42:55Speaker 00

  My, my spending is $300,000 a month. I spent on this and then so they revealed their numbers and then I was like, okay, but tell me how you're messed up because all rich people are messed up in some way. She goes, yeah, I'm messed up. So like I still use it. I still use this sheet to like, make sure I'm never going to run out of money and I fear running out of money for these reasons. And I'm like, this is just so beautiful because the more successful you get, the less people talk about money. I don't know, Jason, if you and your buddies ever like talk about this. It's not really discussed. It's a little bit taboo, but unfortunately, and I, and I know that this sounds kind of like a D-bag of me saying this. And so I try to be very tasteful with all of this, but first of all, problems are still problems. And when you do achieve something, even if you're just a, a, a tech person at Airbnb, you work there and you like just made a million dollars

• 43:38Speaker 00

  off the IPO, you're like, what do I do? What's an, what's an appropriate amount of money to spend every month? Should I spend 10,000 or 50,000? I'm not sure. Where do I invest it? And so my goal has just been to unlock that information and convince people to share that, that stuff. And that's what MoneyWise is.

• 43:53Jason Calacanis?

  So MoneyWise is great, but let's talk about Hamilton because one of my founders is Hampton. Sorry. What did I say? Hamilton? Hampton. Hampton as in the Hamptons. So you picked Hampton because it evokes the Hamptons?

• 44:05Speaker 00

  I'm from Hampton Avenue in St. Louis, Missouri. It's a, it's a, it's a street, but yes, I, I don't mind. Brand is when you associate two things.

• 44:13Jason Calacanis?

  Perfect. I love it. So there's an origin story and then there's me just associating it with the Hamptons, which is by the way, what every rich person in New York, you talk about getting like the Vanity Fair cover treatment or a New York Times story profile in the Sunday edition like Zach just got. Getting a place in the Hamptons that people want to come for dinner. That's impressive. That is also one of the checkbox is. So one of my founders is in it. And when I asked him like, this is costing how much per year? 4,000 a year? 5,000 a year?

• 44:40Speaker 00

  No, it's starting in January. It's 15,000 a year.

• 44:43Jason Calacanis?

  Whoa. Did it start at four or five? Was that the original price? Okay. So it's $15,000 a year to join now.

• 44:49Speaker 00

  For new people, it's going to be 15.

• 44:51Jason Calacanis?

  Amazing. So you start this $15,000. What do people get for $15,000 a year? What? Are you selling essentially? How many people are doing this? And then, yeah, but why did you decide to start this business?

• 45:04Speaker 00

  To what people get? So the way it started is not how it is now. But the way that it is now, we've made this massive pivot this year. But basically you get three things. The first thing that you get is first of all, everyone who applies, we only let in 4% of the people. Last month, we have like, we got like 2,300 applications. And everyone gets interviewed. They have to reveal their traction, so their revenue and things like this. I watch all of the interviews, so does my co-founder. And then the community has to give a thumbs up or thumbs down on you. And once you get in, you get matched with an in-person core group. So that's eight founders of similar sizes and types of businesses. And then we have 100 plus moderators who we pay and train. And they lead these conversations in real life with the same group of eight people every single month for hopefully for a decade that you're going to be with them. And so the idea is that these eight person groups,

• 45:49Speaker 00

  they're the only people that know about your mommy and daddy issues, but also about like what's going on with your business. And then the second thing, and so this way they have full context in your life and they can actually like give you advice and feedback. The second thing that you get is a chapter. So like, let's say in New York, we have 190 members. So you get a local chapters with tons of cool events. We've done them with Joe Lonsdale in Austin, Texas. We've done Jason Fried in LA, things like that. And then the last thing is you get a Slack group where we have 1,000 plus members and you could type in anything and you'll get an answer within 20 minutes because that's part of the culture.

• 46:17Jason Calacanis?

  So essentially YPO, but maybe open to more people. Because this young president's organization, they tried to loop me into this and they were like, oh, you have to have 10 million in revenue. At the time, I think Mahalo had like five. I'm like, I'm not qualified. They're like, you're qualified, you can come in. We'll waive the 10 million thing. And they kept trying to get me to do this. I just didn't have the time. But this, people have told me they're in the same cohort for their, you know, for 20 years. And these are, it's almost like a fraternity is how they refer to it. So it's similar. Was that the inspiration for it of something similar or analogous? That's more open to people?

• 46:49Speaker 00

  Yeah, YPO is well known and I think they're wonderful. The difference is, is that YPO, even though it's called Young Presidents Organization, a lot of their members are a little bit older, which is all good. And it's also a lot of people who maybe own like a manufacturing company or a real estate business or something like this. And so in order to get into Hampton, you have to have at least three million in revenue, three million in funding, or you have to hold a business for $10 million and you have to have some type of digital or internet type of shtick.

• 47:13Jason Calacanis?

  Tell us about the moderators, because that seems to be a key piece of this.

• 47:17Speaker 00

  Yeah, it's a pain in the ass is what it is, but.

• 47:20Jason Calacanis?

  Because, you know, anybody can start a small community, but to scale a community, that's always where it gets hard. So I get the sense, if I'm reading into it correctly, that that's what you're in the mix of now in year two or three of Hampton?

• 47:32Speaker 00

  No, dude, when we launched, we were digital. We launched sort of post-COVID and we thought that people would want to meet on Zoom. Obviously, that was foolish of me, right? Everyone wants in real life. And so we pivoted the whole business to be in real life. So this year, we hosted 150 events. And so everything's in real life, plus your core group. And so, but finding a moderator in your city and then training them, training them in the Hampton way, that's really hard. And so we have a team of four people and their whole job is finding these moderators and training them. There's this company called Vistage. Have you ever heard of Vistage?

• 48:01Jason Calacanis?

  I have not, tell me.

• 48:02Speaker 00

  Listen to this. This company does, I guess we do what they do. They were launched in 1962. You know who used to own them? Larry Ellison and Michael, Larry Ellison and Milken. What was his name? Michael Milken?

• 48:14Jason Calacanis?

  Michael Milken, yeah.

• 48:15Speaker 00

  They owned this company together at one point. And so this company has 40,000 people paying on average $20,000 a year to be a member. And you've never, and you've never even heard of them. And my goal with this company was to create a company that could last for 50 or 100 years and wouldn't go out of business with AI. And so I looked at YPO, they launched in the 50s, Vistage launched in the 60s, and there's a handful of others that have been around for 50 or 100 years. And I just thought it'd be really cool to try and build something that can last for a few generations.

• 48:43Jason Calacanis?

  Genius. And you didn't raise money for it? You're just doing this all yourself? You have control of it? And it's your thing?

• 48:50Speaker 00

  Yeah, yeah, yeah. We, I will not, no, we will not raise money. That would mess it up. And I think it could be like a business, I mean, I think, I think we could bootstrap into this into a multi-billion dollar company. It might take 20 years, but you know, I think we can do it.

• 49:03Jason Calacanis?

  It feels like this is the business you were, you know, it's always like when I met you, when you were doing the newsletter and then the events. And I was like, wow, this, this guy's. Figuring it out so fast, but this feels like the last business for you. I'll be totally honest. Like, sometimes a founder gets to a point where it's like, yep, that's your business. Don't ever sell it. Don't ever raise money. Don't ever give up control. That's your first, last. That's it. Do you have that sense now with Hampton?

• 49:30Speaker 00

  Yeah, my, I, my, my daughters are going to intern here. That's my goal. You know, frankly, I'll give you, I gotta give you credit, Jason. I started my last company, The Hustle. I like researched like five people and you were the one, the five people I researched. And I was like, I'm just gonna steal all of that. So I just copied you. And it's, it's, it's turned out good. So please, like, anything you're gonna do next, just tell me. So I

• 49:54Jason Calacanis?

  Well, what did I get right? I mean, what was the thing that you perceived was like, had gotten right then? If I did have something that was influential, yeah.

• 50:04Speaker 00

  Being a media person, so I, I don't know totally about your interests, but I don't have the ability to build a tech company. But I love tech people and the best way to monetize that is to build a media company, not pretend to be a tech guy and just be average at it. And so that's what I copied. And then you had conferences and I was like, conferences? Can that be cool or not? And then I go to lunch and I saw this and I was like, yeah, I'm, I'm gonna go ahead and do that. Thank you.

• 50:30Speaker 00

  And then like, uh, uh, just like you purposely turn on the, um, gregariousness, I think. I don't know how to describe it, but you have this like way about you where you're talking sound bites where I was like, yep, I gotta study that one.

• 50:45Jason Calacanis?

  Candidness for sure. Yeah.

• 50:47Speaker 00

  Yes. And so, um, I basically have just stolen a lot of your stuff.

• 50:52Jason Calacanis?

  Who are the other four? I'm curious. Who else was it? Was it Kevin Rose, Tim Ferriss, Gary Vaynerchuk? Who else made that list of like interesting, you know, web 2.0 people or web 1.0? But obviously Felix Dennis is one of them. Sure. Yeah.

• 51:04Speaker 00

  So Felix Dennis, I studied you a lot. I studied Ted Turner.

• 51:09Jason Calacanis?

  Yes. Really?

• 51:10Speaker 00

  Ted Turner is my hero.

• 51:11Jason Calacanis?

  I love Ted Turner.

• 51:13Speaker 00

  What do you love about him?

• 51:14Jason Calacanis?

  Well, he was iconoclastic in that he had his own opinion of how things should be done. And it, it was

• 51:23Jason Calacanis?

  You know, his way or the highway, and he just made very unilateral decisions based on instinct. And I think that's something in media that's incredibly important. When your organization gets a little bit bigger, people will tell you, like the experts you hire, this most, you basically go hire the most qualified people you can think of. And then they will stop you from doing the magical things you understand how to do. Now, one of the things he wanted to do was to educate the public and do like documentaries. He wanted to do this one on nuclear proliferation. He wanted to have an impact. And then you look at what CNN became. He just wanted you to know what was going on in the world and then educate you as to what are the important issues.

• 52:05Jason Calacanis?

  And CNN then just totally lost this mission at some point because they were watching Rupert Murdoch, who was just like, yeah, just put the most insane people, giving the most crazy opinions on air. And then CNN tried to duplicate that and follow them. And it just didn't work because it wasn't like Tucker and, you know, Megyn Kelly and those kind of spicy people. It just became this weird, kind of somewhere between doing what the BBC does and what Fox does. It was inauthentic. And if they just stuck to what he wanted to do, which was straight reportage, give them the facts and be first. Do really deep analysis of important topics and educate them and elevate the public's knowledge of nuclear proliferation, which was one of his big things.

• 52:50Jason Calacanis?

  And those are the things I loved about him. What did you love about him?

• 52:52Speaker 00

  So I have these categories of people that I call manifest cowboys, meaning they turn dreams into reality, but they do it in a very like, sort of shoot from the hip type of like vibe. And frankly, I view them a little bit as artists. A lot of people think that they're just like loud mouths. And I'm like, no, there's like an art, there's a beauty here. And so what I loved about him, he had a lot of flaws, but what I loved about him is that he was the sky from the south. I'm from Missouri and he moved up to, and he kind of took over like the media world in New York City and he. Built this very amazing company, but he was still like a really scrappy guy who was not, he was, he was willing to look foolish. Like he owned the Atlanta Braves and like he was famous for doing this contest to see who had to push the, the baseball to first base with their nose

• 53:34Speaker 00

  first. And he would get on it, he would get on his hands and knees and he would like do this stuff, even when he was like a billionaire, you know? And I just love that this guy didn't take himself too seriously. Also, a lot of people don't know this, but he saved the buffalo population in America. That was his passion. His passion. And so I just think that like too often in this world, there's this lack of the idea of a total man. So we have these guys in tech and business who are like amazing about making money, but they're lacking like what's, what it means to be masculine, which is you treat people wonderfully, you're, you help others who can't help themselves. You treat women and other people respectfully and like you are a little bit rugged and I love that. And he was like that guy for me.

• 54:11Jason Calacanis?

  Yeah. In New York, he tweets people. Like the fact that this guy in Atlanta who headquartered it in Atlanta and you know, basically could take over the news business without being in a fancy New York City Times Square or Wall Street. He was just like, yeah, that's not what's necessary. I just need to have reporters on the ground. So wherever this war is occurring, I'm sending them there. And it was like very simple, but the way I say the same thing that you're pointing out, you know, iconoclastic is I guess a way to frame, frame it is like, do people do interesting things with their money when they get it? Like a lot of people I know get a ton of money and then they get really scared and they sit on, they don't ever do anything interesting. And what I like is people who do interesting things with their money and

• 54:55Jason Calacanis?

  like do weird stuff, but that makes the world more interesting, right? Actually put Palmer Lucky into that. You know, you watch him and he released a Game Boy, you know, and he does like his cosplay and he dresses up as characters. Now, not for me, I'm not like into Game Boys or. Dressing up in, you know, as anime characters, but God bless him, he's into it. It didn't give a shit what you think about him and his Game Boy or whatever. And great, awesome, like be a cowboy and go do that stuff. And cowboy is like a great way to sort of phrase it. Listen, if people want to apply for Hampton and, you know, get that small chance of getting in, how do they do that? And yeah, where do they go?

• 55:33Speaker 00

  Joinhampton.com and then we'll email you in like 12 or 24 hours. But I watch all the interviews, literally 100% of them. So joinhampton.com.

• 55:41Jason Calacanis?

  So they do a Zoom interview with them and then you watch it and then give a thumbs up, thumbs down, essentially?

• 55:45Speaker 00

  Yeah, they gotta make it past our membership team. So they talk to them for like 45 minutes. Then if the membership team gives them a thumbs up, then me and my partner, Joe, one of us will watch the interview. And then the, once we give a thumbs up, we have an automation that goes to the Slack community, they can give a thumbs up and thumbs down, and then they get their invite.

• 56:00Jason Calacanis?

  Oh, I love that process. Yeah, my, my, my founder who's in it, I said, why did you spend all this money on this? Are you sure it's a good use? And like, am I paying for it or whatever? And he's like, yeah, I met like three people who have been down this road of like M and A and raising money and partnerships with these things. And I was like, yeah, it's worth it. Cause I just, what I told them was, I was like, listen, if it's five grand a year, if you were to hire an M and A banker, it'd be five grand a month for like the low end ones, not low end, but the boutique ones would charge you like a 5K retainer. So a month for six months and for 30,000, you're going to learn this, but you're going to learn it from their perspective. If you're in that community, two or three people explain to you their M and A process and what they went through and then they failed and they succeeded. You're basically paying to take out noise, right?

• 56:44Jason Calacanis?

  That's what you're actually paying for in what you're doing. And people don't understand this about like the All In Summit as an example, which is $7,500 to go. We do do scholarships to kind of just stir the pot a little bit and get interesting up and comers who can put 7,500 on their corporate account. But the $7,500 is like buying a home in Yellowstone. It just means if you're, it's a filtering mechanism, right? And you still have to apply and we don't let. And lawyers, accountants, headhunters and, you know, real estate brokers. We could sell a thousand tickets every event and make 7.5 million just to real estate brokers. They would all come to try to land a customer and they would ruin the vibes. Have you ever had to network with, go to a networking event and there's like four real estate brokers there?

• 57:29Speaker 00

  That's the worst.

• 57:30Jason Calacanis?

  They'll corner you. I mean, and you're like, I have a house. I have two houses. I don't need more houses. Tell me about your kids. Where do you live? How many rooms is that?

• 57:39Speaker 00

  It's almost as bad as like a financial advisor event.

• 57:41Jason Calacanis?

  That's, I think, yeah, the financial advisors are also can be rough. Yeah, they, yeah, I mean, I'm, when I get the financial advisor pitching me, I'm like, so, um, do you think you could beat my returns? And they're like, no. I'm like, so what would I use you for? I like, I'm young enough to run my own book. I'm 55. I'm just going to run my own book. I'm like, they're like, I can get you margin loans or these other devices. I'm like,

• 58:06Speaker 00

  At a 1% fee.

• 58:07Jason Calacanis?

  Well, yeah, and it's the thing about the 1% fee that people don't understand is it's not 1% of the 5% return this year. It's one of the five points and two of the five points go to Uncle Sam or two and a half, depending on where you live. And then one point goes to your money manager. So now you're at two and a half or three and a half going to your money manager. One and a half going to you. Just buy Vanguard funds like Alex does.

• 58:31Speaker 00

  That's what I do.

• 58:33Jason Calacanis?

  Yeah, just put it all in a Vanguard fund and go back to work.

• 58:35Speaker 01

  Fidelity's zero cost index funds, baby. Free. Love it.

• 58:39Jason Calacanis?

  Listen, we didn't get into, uh, my first million amazing podcast. What I love about your podcast is you find weird people that nobody else has. So just to give you a, another high five here, but what I appreciate about, appreciate about it, Sam is, um, and your, your, your, uh, co-host, I don't know his name, but,

• 58:56Speaker 00

  John.

• 58:57Jason Calacanis?

  No, I'm just trolling him. I told him like a couple of years ago because he was saying such a phrase like, who is this guy?

• 59:04Speaker 00

  There was one time where, okay, so I, for the listener, I, you know, I've said I've admired Jason for probably a decade and a half now. And there was one time where you and I hung out and you totally tried to big dog me and you're like, oh, that little newsletter thing, tell me about it.

• 59:19Jason Calacanis?

  Yes. Then you told me you make it 10 million. I was like, what?

• 59:22Speaker 00

  In my head, I was like, he's trying to rattle me and he's a good guy. He's trying to mess with me and I love this.

• 59:28Jason Calacanis?

  No, I had no idea. Honestly, that was more me being a dipshit because I was like, you invited me to speak at your event down in Oakland. It was like one of your first ones. And I was like, who is this guy? He's like making so much noise. I have to meet him. And it wasn't actually big dogging. It was me not doing my research. And this is one of the things I always train my team on because I learned this from angel investing early on, never underestimate anyone because the people who you meet who seem a little awkward, or maybe they're just a little weird, like they're going to turn out to be Elon or Travis or Palmer or Sam Parr. They're going to actually go from being awkward or hard to understand, or maybe you don't appreciate, and then they figure it out.

• 1:00:08Speaker 00

  People underestimate stuff all the time. I don't, you know, a lot of people underestimate newsletters. My prediction was that we could get to 100 million in 10 years. I sold too early, but my competitors now are doing 90 million in revenue, Morning Brew. And so like, people laughed at the idea of a newsletter, but you know, but very few people know they can be legit.

• 1:00:25Jason Calacanis?

  When I sold Weblogs Inc. for 30 million bucks, 18 months after starting it, everyone's like, you sold too early. I was like, you know what? Never too early to get your first 10 million. Like my partner and I, when you get that, you're actually dangerous. That's when you become super dangerous is when you have the FU money, then the next project or two or three, you get to choose and you can play long as opposed to playing scared or playing on your heels. You don't have to make money from Hampton. You could just invest 110% of the, you know, revenue back into it, which I assume is what you're doing. You're not going to run it to make short-term gains. You're going to run it for long-term legacy and enterprise value, which is what Felix was talking about. Hey, the enterprise value and your equity stake.

• 1:01:10Jason Calacanis?

  Is the big win, not your income?

• 1:01:12Speaker 00

  I stole the strategy from Felix. So what he said was, he goes, if I could do it all again, and I weren't, he said, he goes, I was a punch drunk boxer who just had to keep going back and back and back to making more money. But if I could do it all over again, I would try to make as much money as possible at the age of 35, and then I would relax and write poetry. I don't like poetry. I do like business. But my goal was to make a lot of money by the age, in my case, 31. So I don't have to worry about that. And, and that's why I saw what Jason did. I was like, 18 months, 30 million? Sounds good to me. Let's try.

• 1:01:47Jason Calacanis?

  And I think you sold it for the exact same number.

• 1:01:49Speaker 00

  Well, so we got a deal because of the podcast, which kind of made things a lot nicer. But yeah, but, but you sold, you know, 15 years prior. So like, it was, that was even bigger deal.

• 1:02:00Jason Calacanis?

  Well, when you think about it, this is what, you know, Nick Denton and I had this discussion because Nick Denton wound up selling for 150 million after being sued. And, but he went 10 years, he went 10 years past me in running Gawker. And then he had to give like 50 million of it to his lawyers, 50 million of it to a private equity firm, 50 million of it to Hulk Hogan, like, he probably wound up making, you know, double what I made or something, or me and Brian Alvey made.

• 1:02:24Speaker 00

  Yeah, but at the cost of a decade.

• 1:02:26Jason Calacanis?

  At the cost of a decade, and then being dragged the, the, the court system for all this. And my previous partner, Mike Arrington, on the TechCrunch 50 conference, he saw what I did. And he was like, just please introduce me to AOL. I have to sell this thing. And he wound up selling it to AOL for 25 million, literally like two years after, three years after I met him, like same exact playbook, like, get this out quick, and then I'll go on to my next thing. Listen, Sam.

• 1:02:51Speaker 00

  I could talk to you guys all day about media, by the way, so.

• 1:02:54Jason Calacanis?

  Oh, you and I will do another pod just on media and like other media brands we love. Are there other media brands you're, you're loving right now? What do you, what do you, who's impressing you? Any, who's the next Sam Parr? Who's the next J. Cal? Who's the next Felix Dennis?

• 1:03:09Speaker 00

  Founders, the podcast called Founders. And there's another one called How to Take Over the World. That's even smaller that I think is going to be huge. I think How to Take Over the World is just magical. It's a podcast.

• 1:03:18Jason Calacanis?

  Ben Wilson.

• 1:03:20Speaker 00

  Ben Wilson, How to Take Over the World. He used to be my producer in My First Million. He's got, he just came out with this two-part series on Andrew Carnegie.

• 1:03:26Jason Calacanis?

  Oh, he's kind of doing like acquired kind of style?

• 1:03:29Speaker 00

  Three-hour series on people who take over the world.

• 1:03:31Jason Calacanis?

  Got it. Yeah. It's like acquired, but for people.

• 1:03:33Speaker 00

  Yeah. So I love that. So I'm very bullish on that. But yeah, I could talk about you like I stole my strategy from you and Kevin Ryan. So I could talk about all day.

• 1:03:42Jason Calacanis?

  Oh, Kevin Ryan. Yeah. Very smart as well. A lot of, a lot of great entrepreneurs out there. All right. Listen, I'll drop you off, Sam. And let's catch up soon and say hi to your co-host, your, uh, who's the, who's the co-host of that, My First Million?

• 1:03:54Speaker 00

  Just some dude. Just a guy. We're just gonna call him dude.

• 1:03:56Jason Calacanis?

  I know. He's great too, by the way. He does a great job. And everybody check out those podcasts and go to Hampton. All right, Sam, thank you so much for coming on.

• 1:04:04Speaker 00

  God bless you guys. Thank you, everyone.

• 1:04:05Speaker 01

  That was so much fun. Also, my parents are from the Midwest, so I love, I love, I love, I love getting the Midwest connection. But Jason, let's do a little bit of fun here. Before we had Sam on, we actually asked producer Claude to do a kind of similar take. What should founders know all about copyrighting? And so I thought we'd go ahead and just take a peek and see what producer Claude said. So this is what Claude came up with, Jason. So here in the core principles section, write like you talk, which we covered quite a lot. We also talked about answering the why should I care? And we talked about testing relentlessly and using social media as a platform to do that. And then later on, talking about, you know, publishing strategies and so forth, how important podcasts are. And then I love this, tools like Hemingway editor keep writing crisp. So I really feel like Claude did a good job here of nailing quite a lot of what we talked about with Sam.

• 1:04:50Jason Calacanis?

  Well, this is, I think, another thing that Sam did brilliantly. You know, when he came into the game, people were probably like, oh, you know, like it's too late. But he did, he, if you can, the, the way I would phrase this is stand on the shoulders of giants. He came out, he said, okay, who are the giants? Okay, these different advertising heads from the 50s and 60s figured this out. Let me study them and write new content about what they did. And you know, SEO is one strategy from the old days. SEO, search and optimization. But now his content's now showing up, I'm certain. And the advice that's being given by Claude is coming because it's probably indexed some of the things he's written. And he probably mentioned like three times Hemingway. You know, you can always get the citations.

• 1:05:33Jason Calacanis?

  So, you know, in the screenshot, you don't see the citations, but the citations will be there. That's why I always ask whenever I do a Claude search, hey, show me the citations and give me a quote from people who've talked about it. Just a great way to add a prompt and Claude makes us just absolutely superhuman at what we do here at This Week in Startups. And you can be superhuman like us, not superhuman, the email program that makes Grammarly, but you can be superhuman with Claude.

• 1:05:58Speaker 01

  You can get 50% off your first three months of Claude Pro. Just go to claude.ai/twist to get started. You can't do everything we do with Claude without a paid plan. We fully recommend it and we use Claude every single show to make sure we're verified, up to date and fully rocked and ready to go.