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Sam Parr
Co-host, My First Million; Founder of Hampton, My First Million

Level up your copywriting w/ Sam Parr | E2226

📅 Dec 19, 2025 This Week in Startups 66 MIN 252966 VIEWS 166 SEGMENTS · 4 SPEAKERS
This Week In Startups is made possible by: Luma AI - https://lumalabs.ai/twist Northwest Registered Agent - https://www.northwestregisteredagent.... 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...

Questions asked in this interview

12
  1. 0:25What percentage of the lessons persist and kind of hold true in the current moment?
  2. 3:16How did you become obsessed with copywriting and why?
  3. 14:02So 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?
  4. 19:30It was at this terrible conference facility, but I learned like three really good things on stage, right?
  5. 24:42And so it just prompts you, hey, you want to do a couple of puzzles?
  6. 28:42What should be the hero image, the hero lead?
  7. 36:34You 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?
  8. 43:53Sorry, what did I say? Hamilton?
  9. 44:51And then, yeah, why did you decide to start this business?
  10. 49:54I mean, what was the thing that you perceived had gotten right then if I did have something that was influential?
  11. 54:11And yeah, where do they go?
  12. 57:42I'm like, so what would I use you for?
Sam Parr 0:00 ↗
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 DeAngelo, he would write these like 5,000-word emails where it's just plain text, and they were making $30 million a year selling e-books on how to like hook up with a girl.
Jason Calacanis 0:25 ↗
What percentage of the lessons persist and kind of hold true in the current moment?
Sam Parr 0:29 ↗
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 see like cheesy headlines and all that stuff, and 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.
Narrator 0:55 ↗
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Jason Calacanis 1:49 ↗
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.' 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 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?
Alex 2:50 ↗
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 MoneyWise, the show for if you have money and you don't want to lose it. We love him. Sam, welcome to the show.
Sam Parr 3:13 ↗
What's up, guys? Jason, are you going to read the books? Which one did you get?
Jason Calacanis 3:16 ↗
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. 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?
Sam Parr 4:03 ↗
So I used to work—I used to own a hot dog stand in college. That's how I 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 4:17 ↗
That's copywriting. You got a laugh out of us.
Sam Parr 4:20 ↗
Like I wasn't selling anything particularly special. And so I started like Googling—this was back in like 2010—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 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.
Jason Calacanis 4:55 ↗
The PUA movement. Yeah.
Sam Parr 4:57 ↗
Yeah. 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 DeAngelo, he would write these like 5,000-word emails where it's just plain text, and they were making $30 million a year selling e-books 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 love. And so that's how I originally got into copywriting.
Jason Calacanis 5:24 ↗
It's really interesting that these 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 cribbed a lot of my copy for my book. And they were talking about, oh, if you made the Uber investment, you made 2,000x, 5,000x 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 6:11 ↗
They're animals.
Jason Calacanis 6:11 ↗
They're beasts. They're in beast mode. They're relentless about it. I hate these guys.
Sam Parr 6:16 ↗
I was gonna say they stole your stuff.
Jason Calacanis 6:17 ↗
No, no, it's just annoying, but they do understand something. There's something to learn from there. So when I saw you had done all this stuff, I immediately bought this book, Ogilvy on Advertising.
Sam Parr 6:28 ↗
You'll love it.
Jason Calacanis 6:29 ↗
And then Confessions of an Advertising Man. These are the two I bought.
Sam Parr 6:33 ↗
And then type in Joe Sugarman on Amazon and buy his Adweek.
Jason Calacanis 6:38 ↗
Ah, okay.
Sam Parr 6:39 ↗
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 worked. 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 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. 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 Ogilvy is one of those. Ogilvy & Mather, that was a multi-tens-of-billions-of-dollars 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 like he would write these—just they called them sales letters—these letters that they would mail to people to sell anything.
Alex 7:50 ↗
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? Because everyone says the same thing.
Sam Parr 8:00 ↗
So here's what people listening to this, you guys are going to think a couple things. You're going to think ads don't work on me. Obviously, that's nonsense, right? 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 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 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 photo is 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 9:04 ↗
So the never-ending web page 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 to why long works over short? Because intuitively you might be like, 'Hey, TL;DR, concise is better.' Why does long, in your estimation, in your experience, work better than short?
Sam Parr 9:27 ↗
The Adweek. This is one of my favorite books.
Jason Calacanis 9:29 ↗
Just ordered it.
Sam Parr 9:30 ↗
And this looks like not an interesting title, or you know, it's like 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 got to make you desire what I want you to desire. And then I have to make you take action by 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. 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 are 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 pain. So let me give you an example. If you were selling—I'll do a weight loss thing because that's typically kind of scammy—but let's say 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 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 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.
Narrator 11:19 ↗
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Sam Parr 12:29 ↗
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.
Jason Calacanis 12:43 ↗
Unpack those for us as we go down the slope.
Sam Parr 12:46 ↗
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 12:57 ↗
Yeah, I have seen those.
Sam Parr 12:58 ↗
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 jacked, that's why they always carry these jugs of water. So that was my desire. My interest and desire was making you interested. 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 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 a hook. The hook is the first five sentences that grabs your attention. They call it a hook, and then they call it a meat, and then they call it a CTA. So hook, meat, 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, meat, CTA. It's the same thing as attention, interest, desire, action.
Alex 14:02 ↗
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-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 14:31 ↗
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?
Jason Calacanis 14:42 ↗
Yes.
Sam Parr 14:43 ↗
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 going to happen is your funnel—maybe it's going to be that the goal is not to make 100% of the people read your thing. It's to make the right 5% of the people 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 going to make someone compelled to share. And so the thing about copywriting is it's 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 since the beginning of time. There's certain ways to actually do this.
Jason Calacanis 15:32 ↗
One of the techniques that you and I share in common—when I had writers in the magazines back in the day, in the Zen day, and then on to blogging—when writers had writer's block and they couldn't get going, I would say, 'Hey, well, why don't you just talk to me and record it, and I'll give you sort of prompts.' And people said, 'Yeah, you're a great writer, Jason.' I was, you know, 'How'd 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 Dragon 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?
Sam Parr 16:14 ↗
Yeah. 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're 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 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. 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 simple phrases like, 'It's when the tide goes down is when you learn who doesn't have their swimsuit on.' Like these 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. So you always want 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 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 people's heads.
Alex 18:13 ↗
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 18:29 ↗
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 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 statue of David, he goes, 'The statue was in there. I just removed the unnecessary stone.' And the way that I—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 an attention-getting idea. Does that make sense?
Jason Calacanis 19:30 ↗
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, Jason's really smart.' It's like, well, when you're standing next to Travis or Vlad or Chamath or Sachs 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. It's like your old friends might be actually—are your old friends holding you back? Is probably the fair 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—you 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 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—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 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 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.
Narrator 21:14 ↗
You know, being a founder is a lot of work. You have to focus on your fundraising. Then you got to hire the perfect team. 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 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 22:16 ↗
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've heard that before, or 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 the average of your five best friends. But I'm going to tell you something 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 were 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. That's where these large language models have changed everything.
Jason Calacanis 23:13 ↗
I like Grammarly too. You know what I found with Grammarly? I don't know if you use it. Hemingway is similar obviously, but I like that Grammarly follows you around because...
Sam Parr 23:22 ↗
It's awesome.
Jason Calacanis 23:23 ↗
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.
Sam Parr 23:37 ↗
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 copy work. Did you ever read the blog post I wrote about copy work?
Jason Calacanis 23:48 ↗
Yes.
Sam Parr 23:48 ↗
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 or 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—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 can 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 a sales page. So I love hey.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.
Jason Calacanis 24:42 ↗
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 if 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 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 notetaker. AI notetakers—I feel like these things are going to brain rot people because they're not writing it down. And 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, you know, planks. It's like, just do the plank.
Sam Parr 25:58 ↗
Yeah. 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, you're not always a great writer, but a great writer—a clear writer is always a clear thinker. Does that make sense?
Jason Calacanis 26:14 ↗
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, 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.
Alex 26:44 ↗
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 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 27:05 ↗
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 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—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 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 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 28:13 ↗
When you're selling a product or service, you know, software, let's say, and you know, I'll come up with a concept here. TaxGPT is one of our breakout startups in recent history. They're a co-pilot for accountants. Now, there are many features to the TaxGPT product. And I think what will typically happen—I'll even pull up their web page. Just going to be so brutal when we do. But...
Sam Parr 28:37 ↗
Well, do you expect a bunch of AI tax experts to be good writers? We could help them.
Jason Calacanis 28:42 ↗
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 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 Hampton as an example as well because you obviously are, you know, putting your brain cycles on that.
Sam Parr 29:24 ↗
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 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 15th or whatever tax day is, like where you're like scrambling, looking around, 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 have to do that anymore. Like I'm selling—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 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, have you ever had that feeling where 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 30:46 ↗
Taking the terror out of tax season.
Sam Parr 30:48 ↗
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.
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Jason Calacanis 32:02 ↗
Yeah. And then talk about images and image use because here what we see is like 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?
Sam Parr 32:28 ↗
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 sell. And I would probably say that if I'm a small company—are these guys new, right?
Jason Calacanis 32:49 ↗
Yeah. Well, they got their Series A, I think, or they're between Series B and Series A, year two basically is how to think of it.
Sam Parr 32:54 ↗
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 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 page. So, if you look at any About Us page, if you go to Hampton's About Us page, we tell a story. The About Us page is 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. I've made this bet before, people. I think I could sell more copies of anything than most companies with just a Google Sheet or a Google Form and just plain text, than any website that has lots of fancy photos. So I would lean into the personal side.
Jason Calacanis 33:47 ↗
If you take a look, Jason, at the Hampton About Us web page, look at this. This is hilarious.
Sam Parr 33:51 ↗
This is my Hampton co-founder Joe. Yeah, that pulls you in.
Jason Calacanis 33:54 ↗
That does pull you right in and it uses the hero image to show off people. Sorry, back to you. I just wanted to point this out.
Sam Parr 33:59 ↗
Yeah. So this is on my About Us page. 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 a hundred 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...
Jason Calacanis 34:48 ↗
Yeah. 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 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 35:30 ↗
There's a story that matters more than anything. I mean, look at like, I don't want to use one of your nemeses, but like Palmer Luckey has done a great job.
Jason Calacanis 35:38 ↗
I'm a super fan of Palmer.
Sam Parr 35:40 ↗
Look, with Andrew, I think the only reason I brought it up was in Business Insider, there was an article about 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, 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 36:04 ↗
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 36:33 ↗
Good story.
Jason Calacanis 36:34 ↗
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.
Alex 36:58 ↗
And for all the founders listening, I think like copywriting is like one style, but honestly it's rooted in, the takeaway is it's rooted in compelling storytelling. And that's like the most important thing. That's what I wanted to ask about because I think a lot of people are technical founders who are much more familiar with code and being in the background not talking as much, but it sounds like you don't have to actually become 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 37:27 ↗
No, you don't even... First of all, 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 can do all of this via a keyboard. 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.

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APA

Parr, S. (2025, December 19). Level up your copywriting w/ Sam Parr | E2226 [Interview transcript]. This Week in Startups. CEOInterviews.AI. https://ceointerviews.ai/interview/3016543/

MLA

Sam Parr. "Level up your copywriting w/ Sam Parr | E2226." This Week in Startups, 19 Dec. 2025. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3016543/.

BibTeX
@misc{parr2025_3016543,
  author       = {Sam Parr},
  title        = {Level up your copywriting w/ Sam Parr | E2226},
  howpublished = {Interview transcript, This Week in Startups. CEOInterviews.AI},
  year         = {2025},
  month        = {dec},
  url          = {https://ceointerviews.ai/interview/3016543/},
  note         = {Speaker-attributed transcript with timestamps}
}