Level up your copywriting w/ Sam Parr | E2226

Summary

Podcast Summary: Level Up Your Copywriting w/ Sam Parr | This Week in Startups, Ep. 2226

Release Date: December 20, 2025
Host: Jason Calacanis
Guest: Sam Parr (Founder: The Hustle, Hampton, My First Million Podcast)

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Episode Overview

In this lively episode, Jason Calacanis sits down with Sam Parr to dive deep into the art and business impact of copywriting. Drawing on Sam’s journey from hot dog stand hustler to multimillion-dollar founder, the conversation focuses on actionable copywriting strategies, the enduring power of storytelling, the use of AI, and how copywriting principles from the past still drive business growth today. Alongside plenty of practical advice, the hosts share war stories from media, investing, and community-building, making this an essential listen for founders, marketers, and operators.

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Key Discussion Points & Insights

1. Sam Parr’s Copywriting Origin Story

• Early businesses & discovery: Sam recounts running a hot dog stand in college ("Southern Sam's Wieners, as big as a baby's arm") and exploring how to sell more through copy.
  • "I wasn't selling anything particularly special...I realized if I could take my ability to sell one-to-one and put it on paper, you could sell one to an infinite number." — Sam Parr (04:19)
• Inspiration from the Internet marketing world: Learned from long-form sales letters and notorious marketers (e.g., David D'Angelo in the PUA era).

2. Timeless Copywriting Principles

• Long Form vs. Short Form
  • Both Sam and Jason stress that long-form copy STILL works—even in the age of TikTok and X (Twitter), long-form builds investment and trust.
  • "There's no such thing as too long. There's only such a thing as too uninteresting." — Sam Parr (14:31)
  • The "slippery slope" of AIDA — every word encourages the reader to continue: Attention, Interest, Desire, Action. (09:30, 12:46)
• Classic Resources:
  • Sam and Jason recommend learning from copy greats: Ogilvy on Advertising, Confessions of an Advertising Man, Joe Sugarman’s Adweek Copywriting Handbook.
  • Sam emphasizes classic direct mailers' skills: "They got incredibly good at figuring out what words convince people to buy and take action." (06:33)

3. Practical Copywriting Tactics

• Write Like You Talk
  • Use relatable, conversational language at a 4th or 5th-grade level. Reference to Warren Buffett: “If you have to look something up in a thesaurus, don't use the word.” — Sam Parr (16:14)
• Active Voice Over Passive:
  • Make sentences clear and direct: "The boy kicked the ball" (active) vs. "The ball was kicked by the boy" (passive). (16:14)
• Personal Connection
  • Write as if to one person; get intimate with their pain points.
  • Example: Paint a scenario that deeply resonates with your audience’s lived experience—e.g., describing someone always standing on the edge in photos for a weight-loss ad (09:30).
• Copywork as Training:
  • Transcribe great sales letters or book passages by hand to internalize great writing. (23:48)

4. Bridging Old-School Copy to Modern Platforms

• “Human nature is human nature…it’s been the same since the beginning of time. Certain ways to actually do this [influence action] still work.” — Sam Parr (14:31)
• Twitter “thread boys” and Instagram hooks: long-form and emotional investment thrive, even on short-form platforms.
• The goal isn’t to convert everyone—it’s to convert the right 5% highly engaged readers.

5. AI’s Role in Copywriting

• How Sam uses AI:
  • To brainstorm big hooks/ideas and to find evidence (e.g., asking ChatGPT for studies to support a concept). (18:29, 22:16)
  • AI tools like Grammarly and Hemingway are useful for editing, catching passive voice, and improving clarity, but Sam believes AI can’t replace the creative writing process itself.
  • "I use it to help me find the big idea, but it can never do a good job of writing." — Sam Parr (18:29)

6. Crafting Effective Web & Sales Pages

• Leading with Emotion, Not Features
  • Above the fold: Show a feeling or story, not just product features.
  • For startups: Empathize with customer’s pain, not just what the product does. E.g., “Taking the terror out of tax season” for a tax product. (29:23)
• About Us Pages & Authentic Founder Videos
  • The story and intention behind the company/founder matters to buyers.

7. Building “Hampton”—Exclusive Community for Founders

• Hampton Model (44:49):
  • $15k/year membership; only 4% acceptance rate.
  • Small core groups of 8, led by trained moderators (46:17), focused on deep bonds and business/psychological support.
  • Mix of in-person and digital interactions.
  • Inspired by legacy organizations like YPO and Vistage, but more contemporary and startup-focused.
  • "My daughters are going to intern here. That's my goal..." — Sam Parr (49:30)

8. The Power of Story in Business Growth

• Great products alone are no longer defensible; intention and authentic narrative are critical for lasting brands (34:48).
• Personal stories (success, loss, motivation) drive connection, loyalty, and outsized value.
  • "The story matters more than anything." — Sam Parr (35:30)
• Underappreciated founders/ideas can massively outperform—never underestimate an “awkward” or unconventional builder (59:19).

9. Media Entrepreneur Wisdom

• Reflections on selling early vs. late (Hustle, Weblogs Inc.), career philosophy, and inspiration from media moguls like Felix Dennis and Ted Turner (37:47, 51:04).
  • "If you can make as much money as possible by 35, you can relax and write poetry... 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." — Sam Parr (61:12)

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Notable Quotes & Memorable Moments

• On Long-Form Copy:
  “You want the least amount of words to be the most effective. And oftentimes, you need a lot of words to be incredibly effective.” — Sam Parr (09:30)
• On AI and Copy:
  "I use [AI] to help me find the big idea, but it can never do a good job of writing." — Sam Parr (18:29)
• On Learning Copywriting:
  "If you do [copywork] for 20 minutes a day, for 20 days, you will get better..." — Sam Parr (23:48)
• On Startups and Storytelling:
  "In today's market... the intent of the founder, the intent of the artist, why did they make this... Why did they create this product? ...Intent matters, right? Why you made the product." — Jason Calacanis (34:48)
• On Community and Moderation:
  "But finding a moderator in your city and then training them, training them in the Hampton way, that's really hard." — Sam Parr (47:17)

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Timestamps for Key Segments

| Segment | Topic | Timestamp | |-------------------------------------|-----------------------------------------------------------------|-------------| | Opening, Sam’s copywriting story | Hot dog stand, discovering copywriting | 04:03–05:24 | | Classic advertising books | Ogilvy, Sugarman, Copywriting roots | 06:28–07:49 | | The Power of Long-Form Copy | AIDA, slippery slope, emotional hooks | 09:04–12:46 | | Applying AIDA, Instagram hooks | Modern hooks, emotional engagement, call-to-action | 12:46–14:01 | | Copywriting Tactics | Write like you talk, active voice, personal angle | 16:14–18:13 | | AI and Copywriting | Using AI for hooks, not for the writing itself | 18:13–19:29 | | Web Copy, “Above The Fold” advice | Leading with emotion, not features | 29:23–30:46 | | About Us pages, adding story | Power of storytelling and authenticity | 32:54–34:48 | | The necessity of founder intent | Product intent, story over tech | 34:48–36:58 | | Building Hampton community | Pricing, structure, value proposition | 44:49–46:48 | | Moderators in community | The importance and challenge of training moderators | 47:13–48:43 | | Longevity & legacy businesses | Learning from YPO, Vistage, building for 50+ years | 48:15–48:43 | | Parallels in media entrepreneurship | Selling too early, the importance of equity vs. income | 60:25–62:24 | | Closing recommendations | Favorite up-and-coming podcasts | 63:09–63:41 |

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Resources Mentioned

• Books:
  • Ogilvy on Advertising — David Ogilvy
  • Confessions of an Advertising Man — David Ogilvy
  • The Adweek Copywriting Handbook — Joe Sugarman
  • How to Get Rich — Felix Dennis
• Apps:
  • Hemingway Editor (hemingwayapp.com)
  • Grammarly
• Communities:
  • Hampton (joinhampton.com)
  • YPO, Vistage
• Podcasts:
  • My First Million
  • Money Wise
  • Founders
  • How to Take Over the World (Ben Wilson)

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Final Takeaways

This episode delivers a masterclass in copywriting for founders, blending practical how-to's (“write like you talk”, use copywork, personal storytelling) with business lessons from decades of media entrepreneurship. Whether building a landing page, an email campaign, or a billion-dollar community like Hampton, the skills and mindsets shared by Sam Parr—and drawn out by Jason Calacanis—remain timeless.

“Copywriting is just sales on paper... It's rooted in compelling storytelling, which is the most important thing.” — Sam Parr (47:27, 36:58)

For anyone building, selling, or communicating online: study the greats, clarify your thinking, and don’t underestimate the power of a good story.

Transcript

[Sam Parr]

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 was just plain text. And they were making $30 million a year selling ebooks on how to, like, hook up with the girl, what percentage.

[Chris Gates]

Of the lessons persistent and kind of hold true in the current moment.

[Sam Parr]

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 gonna say, that doesn't work on me. That used to work then, it doesn't work nowadays. And you're gonna, like, see like cheesy headlines and all that stuff. You're gonna 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 gonna believe it.

[Chris Gates]

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[Jason 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 because I was looking at their web pages and I was like, my God, this copy sucks. And then I looked at some of my own web pages and said, my God, this copy sucks.

[Sam Parr]

And.

[Jason Calacanis]

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, some perplexity searches, and Sam came up, so he's well indexed on this topic. And I started buying all the books that he recommends, all these books by old advertising copywriters. And that's gonna 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?

[Chris Gates]

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 youf have Money and. And you don't Want to Lose It. We love them. Sam, welcome to the show.

[Sam Parr]

What's up, guys? Jason, are you going to read the books? Which one did you get?

[Jason Calacanis]

Gosh, you know, I. 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 gave me all the sources. And then I just opened up Amazon and I just bought them all. Now 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 founders need to do that. How did you become obsessed with copywriting and why? So.

[Sam Parr]

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 Wieners, as big as a baby's arm. And I would like, sell. Yeah, you know, that's called copywriting.

[Jason Calacanis]

That's copyright. You gotta laugh out of us.

[Sam Parr]

Like, I wasn't selling anything particularly special. And so I started like, Googling. This was back in like 10, 2010, like how to. 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.

[Chris Gates]

The PUA movement.

[Sam Parr]

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, like there's a guy named David D'. Angelo, he would write these like 5,5000 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. 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.

[Jason Calacanis]

It's really interesting that 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 recognize. 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 2000x, 5000x if you did this investment. And I was like, oh my God, these guys have out marketed me and I wrote the goddamn book.

[Sam Parr]

They're animals.

[Jason Calacanis]

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

[Chris Gates]

I was going to say they stole your stuff.

[Jason Calacanis]

It's just annoying. But they do understand something. Yeah, there's something to learn from there. So when I saw you had, you had know, done all this stuff, I immediately bought this book, Ogilvy on advertising.

[Sam Parr]

You'll love it.

[Jason Calacanis]

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

[Sam Parr]

And then type in Joe Sugarman on Amazon and buy his Ad Week guide to Copywriting. Ah, okay, 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 Ogilvie and they basically wanted to sell, let's say a vacuum to a housewife. Well how 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 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 do stuff. 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 heard Ogilvy Mather, that was a multi tens of billions of dollar ad firm now. And it's, 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 call them sales letters, these letters that they would mail to people to sell anything.

[Chris Gates]

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

[Sam Parr]

Because all really everyone says the same thing. So here's what people listening to this, you guys are going to think a couple 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, 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. 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 of the words that were on there as well as all the photos as well as all the reviews, there's probably 10,000 reviews. That was probably tens of thousands of words on there. If you go to apple.com and you look at how much an iPhone costs or you want to buy an iPhone, it's going to have a photo, a photos worth a thousand words, tons of photos and tons of words. 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.

[Jason 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?

[Sam Parr]

The Ad Week this is one of my favorite books.

[Jason Calacanis]

Just ordered it.

[Sam Parr]

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 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 Aida. 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 and 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. 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 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. I know why you do that. And you, like, go into, like, the shame that someone feels. And, 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.

[Jason Calacanis]

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[Sam Parr]

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 these facts. I would say, have you ever seen those big muscular guys at the gym carrying around gallons of jugs of water?

[Jason Calacanis]

Yeah, I have seen those.

[Sam Parr]

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 essential 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 in desire was making interest. 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 can 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 a hook. The hook is the first five sentence 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 going to say, hook, meet cta. It's the same thing as attention, interest, desire, action.

[Chris Gates]

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, with their copywriting, I'm thinking about places like X, which are inherently short form 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.

[Sam Parr]

There's no such thing as too long. There's only such a thing as too uninteresting. Do you guys remember in on Twitter, when Twitter got really popular during the pandemic, there was this joke of people called thread boys. Yes, that's exactly what I'm describing here. 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 going to happen is your funnel. Maybe it's going to 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 read to read your thing. And you want them to share at a 90, 90% rate, as opposed to a lot of normal content. You might have a lot of eyeballs, but it's not going to 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 is human nature. It's been the same for since the beginning of time. There's certain ways to actually do this.

[Jason 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. I said, well, you know, how did you get trained? And I said, well, I will talk into. 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. And I would try to just say it like I was saying it to a friend. So maybe unpack, talk, like. And this. I think one of your core tenants write like you speak, right? Yeah.

[Sam Parr]

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 4th or 5th 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. 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. Um, and so I tell people, start with a 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. 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 paid 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 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.

[Chris Gates]

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?

[Sam Parr]

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 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 a attention getting idea. Does that make sense?

[Jason 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. Because 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, JCal's really smart. And it's like, well, you're standing next to Travis or Vlad or Chamath or Sacks or Elon. Yeah, you're going to 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 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 interesting. So if 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. Cause 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 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. Yeah. 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 because for just $39 plus state fee fees, they will act as your registered agent. That means they take care of all the paperwork, making sure your business remains compliant, protecting your privacy and more. And as a founder, hey, man. There are so many organizational odds and ends that you have to worry about. So why not have a partner who can focus on all those little details? Then you can obsess about your customers. And Northwest Registered Agent is even going to help you set up a phone line, a professional email account, and find you a great domain name. So here's your call to action. Go to northwestregisteredagent.com twist to get your company set up the right way.

[Sam Parr]

So let's get even deeper. So what I would. So I used AI that exact phrase. If you're the average of the five friends. I was like, 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 looked 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 looked at this over 20,000 people over a decade. Now, here's the good news for you. You can pick who you can be around. So anyway, you see how, like, we can, like now, I didn't know about that study, but I asked ChatGPT. I'm like, give me some type of evidence.

[Jason 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 it's awesome. 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, uh, 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.

[Sam Parr]

Yeah, 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?

[Jason Calacanis]

Yes.

[Sam Parr]

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 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. 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, would 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, like a sales page, you find sales page. So I love hey dot 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 when you're doing.

[Jason Calacanis]

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. 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 moleskin. 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 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 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 would be kind of like these people who put the pads on their abs and then shoot electricity in it, as opposed to doing planks. It's like, just do the plaque.

[Sam Parr]

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?

[Jason Calacanis]

It makes infinite sense. Because 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 would be like, oh, 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.

[Chris Gates]

I was just thinking about 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.

[Sam Parr]

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 on advertising. I would read that book and that would do a good job of 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 someone we want to recruit, to someone we want to raise. From Jason, I'm trying to sell him to invest in my startup. And so copywriting is just sales on paper. And so I think that we have to convince you to do that. And so the second thing, if we were 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 pages out of it, word for word. 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, is 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.

[Jason Calacanis]

When you're selling a product or service you know, software, let's say, and, you know, 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, their webpage is going to be so brutal when we do.

[Sam Parr]

But what do you expect, a bunch of AI tax experts to be good writers? We could help them.

[Jason 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. 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.

[Sam Parr]

Above the fold should be a feeling, I think. So I'm looking@tax GPT.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 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 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 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, 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?

[Jason Calacanis]

Taking the terror out of tax season.

[Sam Parr]

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

[Jason Calacanis]

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[Sam Parr]

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 say Excel. And I would probably say that if I'm a small company. Are these guys, these guys are new, right?

[Jason 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.

[Sam Parr]

There's a world where I would put, like for any smallish 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. 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, people. I think I could sell more copies of anything. And then 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.

[Chris Gates]

If you take a look, Jason, at the Hampton About Us webpage. Look at this. This is hilarious.

[Jason Calacanis]

This is my Hampton co founder, Joe. Yeah, that pulls you in.

[Chris Gates]

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.

[Sam Parr]

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 Inc. Magazine story about him and the story about how he lost $100 million. So the story goes, my partner Joe was a very successful entrepreneur. He started a company that he sold for $114 million 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 $70 million very fast. But then Facebook made a huge change. And unfortunately, this change happened right as Joe was about to sell the company for $100 million. Zuckerberg made the change to the algorithm. His revenue dropped from 60 million to 10 million, and the company went out of business three months later. And that photo is from an Inc. Magazine story written about that experience. And that is when I met Joe and we had conversations that could help push ourselves forward. And that's when we had the idea for Hampton. Let's do this for other people. So do you See how like I. Yeah.

[Jason Calacanis]

You know, what this speaks to is 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, you know, 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.

[Sam Parr]

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 like Palmer, Palmer Lucky has done a great job.

[Jason Calacanis]

I'm super fan of Palmer.

[Sam Parr]

Look with, with Andrew, 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.

[Jason 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.

[Sam Parr]

Good story.

[Jason 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.

[Sam Parr]

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

[Chris Gates]

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 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.

[Sam Parr]

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 likable on camera for one, and for two, you could do all of this via a keyboard.

[Jason Calacanis]

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

[Sam Parr]

Oh, you love that one.

[Jason 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 90s, and he had done, I think, Maxim 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 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.

[Sam Parr]

Yeah, Felix Dennis. That book changed my life. 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 I not seen spent $100 million on crack and whores in the 90s. 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, I've tried to meet some of his colleagues. So that's so cool that you met him. Was he a cool. Was he cool guy?

[Jason Calacanis]

Yeah, he was kind of like one of these. When I was coming up in the 90s and, you know, in the late 80s, early 90s, if you want it 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.

[Sam Parr]

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

[Jason Calacanis]

It's hilarious. Like JFK Jr. Who I met twice in the 90s 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 create Silicon Valley Reporter. Sure enough, I wound up on 60 Minutes, Charlie Rose on the COVID 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've sort of transcended New York 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 COVID And Jan Winer 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 iPad. 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.

[Sam Parr]

That's awesome.

[Jason Calacanis]

And he said, whatever you spend on the magazine, from page 2 to the page 100, spend the same amount of money on the COVID So if you're spending 10,000 on the writers and the photography and the illustrations inside, spend 10,000 on the COVID And I was spending like 5% on the COVID He said, people judge a book by its cover. It's all about the COVID 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 Graydon Carter when I was coming up, and he mentioned independently how much he loved the covers of Silicon Alley Reporter. So it's just ironic that that was the format. Now today it's having a podcast. You know, 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 did you get it?

[Sam Parr]

In order to promote Hampton, what we noticed was that a common conversation. 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 could 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.

[Jason Calacanis]

And my.

[Sam Parr]

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. 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 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 tech person at Airbnb, you work there, and you, like, just made a million dollars 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 money wise is.

[Jason Calacanis]

So money wise is great. But let's talk about Hamilton, because one of my.

[Chris Gates]

Hampton.

[Jason Calacanis]

Sorry, what? I say Hamilton. Hampton. Hampton, as in the Hamptons. So you picked Hampton because it evokes the Hamptons.

[Sam Parr]

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

[Jason 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, when 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 check boxes. 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?

[Sam Parr]

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

[Jason Calacanis]

Whoa. Did it start at 4 or 5? Was that the original price? Okay, so it's $15,000 a year to.

[Sam Parr]

Join now for new people, it's going to be 15.

[Jason 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. Why did you decide to start this.

[Sam Parr]

Business 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, 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 up thumbs, 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 a hundred 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, 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 local chapters with tons of cool events. We've done them with Joe Lonsdale in Austin, Texas, we've done Jason Freed in la, things like that. And then the last thing is you get a slack group where we have a thousand plus members and you could type in anything and you'll get an answer within 20 minutes because that's part of the culture.

[Jason 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?

[Sam Parr]

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 3 million in revenue, 3 million in funding, or you have to sold a business for $10 million and you have to have some type of digital or Internet type of shtick.

[Jason Calacanis]

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

[Sam Parr]

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

[Jason Calacanis]

But because you know, anybody can start a small community, but to scale a community, that's always where it gets hard. So I get a 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.

[Sam Parr]

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've 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?

[Jason Calacanis]

I have not. Tell me.

[Sam Parr]

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.

[Jason Calacanis]

Michael Milken, yeah.

[Sam Parr]

They owned this company together at one point. And so this company has 40,000 people per, 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.

[Jason 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.

[Sam Parr]

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 biz. 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.

[Jason 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. With Hampton?

[Sam Parr]

Yeah, my. I. My. My daughters are going to intern here. That's my goal. You know, frankly, I'll give you. I got to give you credit, Jason. I started my last company, the Hustle. I like, research, like, five people, and you were the one of the five people who 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 could.

[Jason Calacanis]

But 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 I. That was influential?

[Sam Parr]

Yeah, being a media person. So 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 launch, and I saw this, and I was like, yeah, I'm gonna go ahead and do that. Thank you. And then, like, just, like, you purposely turn on the gregariousness, I think. I don't know how to describe it, but you have this, like, way about you where you talk in sound bites, where I was like, yep, I gotta.

[Jason Calacanis]

Study that one candidness for sure. Yeah.

[Sam Parr]

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

[Jason 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.

[Sam Parr]

So, Felix Dennis, I studied you a lot. I studied Ted Turner. Yes. Really? Ted Turner's my hero.

[Jason Calacanis]

I love Ted Turner.

[Sam Parr]

What do you love about him?

[Jason Calacanis]

Well, he was iconoclastic in that he had his own opinion of how things should be done. And it was, 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 to you to know what was going on in the world and then educate you as to what are the important issues. 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 peripheralization, which was one of his big things. And those are things I loved about. What did you love about him?

[Sam Parr]

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 loudmouths. 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 this guy 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 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.

[Jason Calacanis]

Yeah. In New York, he tweaked 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. It 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 and, you know, iconoclastic is, I guess a way to 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, 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, you know, as anime characters. But God bless him, he's into it. He 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?

[Sam Parr]

Join hampton.com and then we'll email you in like 12 or 24 hours. But I watch all the interviews, literally 100% of them. So join handed.com so they do a.

[Jason Calacanis]

Zoom interview with them and then you watch it and then give a thumbs up, thumbs down essentially.

[Sam Parr]

Yeah, they got to 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.

[Jason 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. Because 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 would 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? 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't 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.

[Sam Parr]

Right.

[Jason Calacanis]

And you still have to apply. And we don't let lawyers, accountants, headhunters, and you know, real estate brokers. The, the, 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?

[Sam Parr]

Yeah, it's the worst.

[Jason 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. Like, tell me about your kids. Where do you live? How many rooms?

[Sam Parr]

Is that almost as bad as like a financial advisor event.

[Jason 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 advisors pitching me, I'm like, so do you think you could beat my returns? And they're like, no. I'm like, so what would I use you for? I'm 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.

[Sam Parr]

I'm like, at a 1% fee.

[Jason 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.

[Sam Parr]

That's what I do. Yeah. Put it all in a Vanguard fund.

[Jason Calacanis]

And go back to work.

[Chris Gates]

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

[Jason Calacanis]

Listen, we didn't get into my first million amazing podcast. What I love about your podcast is you find weird people that nobody else has. So just give you a, another high five here. But what I appreciate about, appreciate about it, Sam is and your, your, your co host, I don't know his name, but John. No, I'm just trolling him. I trolled him like a couple years ago because he was saying such a mess. Like who is this guy?

[Sam Parr]

There was one time where, okay, so for the listener, I, 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.

[Jason Calacanis]

Yes. Then you told me you're making 10 million. I was like, what?

[Sam Parr]

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.

[Jason 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 out 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 doing 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 Par. 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.

[Sam Parr]

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 a hundred million in ten 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.

[Jason Calacanis]

When I sold Weblogs Inc. For 30 million bucks 18 months after starting it, everybody'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, you. 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 is the big win. Not your income.

[Sam Parr]

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. 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 be. Let's try. And I think you sold it for.

[Jason Calacanis]

The exact same number.

[Sam Parr]

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 a. That was even bigger deal.

[Jason 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, I probably want to make it, you know, double what I made or something. Or me and Brian Alvi.

[Sam Parr]

Yeah, but at the cost of a decade.

[Jason Calacanis]

At the cost of a decade. And then being dragged through 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.

[Sam Parr]

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

[Jason Calacanis]

So you and I will do another pod just on media and like other media brands. We love other. Other media brands. You're. You're loving right now. What do you. What are you. Who's impressing you any. Who's the next Sampar? Who's the next jcal? Who's the next Felix Dennis?

[Sam Parr]

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.

[Jason Calacanis]

Ben Wilson.

[Sam Parr]

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.

[Jason Calacanis]

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

[Sam Parr]

Three hour series on people who take over the world.

[Jason Calacanis]

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

[Sam Parr]

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.

[Jason Calacanis]

Oh, Kevin Ryan. Yeah. Very smart as well. A lot of. A lot of great entrepreneurs there. All right, listen, I'll drop you off, Sam, and let's catch up soon and say hi to your co. Your. Who's the. Who's the co. Host of that. With the. My First Million.

[Sam Parr]

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

[Jason 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.

[Sam Parr]

God bless you guys. Thank you, everyone.

[Chris Gates]

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 copywriting? And so I thought we'd go ahead and just take a peek and see what pretty sure Claude say.

[Jason Calacanis]

Here we go.

[Chris Gates]

So this is what Claude came up with, Jason. He says 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.

[Jason 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 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 engine 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 index some of the things he's written and he probably mentioned like three times Hemingway. You know you can always get the citation. So you know in this screenshot you don't see the citations, but the citations will be there. I that's why I always ask whenever I do a cloud 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 could be superhuman with Claude.

[Chris Gates]

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 cloud 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.