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

How Sam Parr Mastered Copywriting for a $27M Exit

📅 Jan 27, 2025 Content and Conversation 46 MIN 3398 VIEWS 88 SEGMENTS · 2 SPEAKERS
In the latest episode of Content and Conversation, Sam Parr, founder of The Hustle and host of My First Million, joins Ross to discuss the art and science of great copywriting, building viral content, and scaling content-driven businesses. Sam shares actionable insights into hiring creative talent, writing headlines that convert, and why simplicity is the ultimate sophistication in copywriting. Show Notes: 00:00 Sam Parr’s journey in copywriting and content creation 01:03 Combining Silicon Valley innovation with internet marketing 02:45 The Hustle’s Newsletter Success 06:12 Hiring Creative...

Questions asked in this interview

12
  1. 2:05Are there any specific techniques you used to kind of employ that across the team?
  2. 9:33Wasn't that one of his kind of okay dork philosophies?
  3. 15:54So is that how you're doing that in practice?
  4. 16:54And this is across networks or you're thinking about YouTube in particular?
  5. 20:28Is it in your post structure templates?
  6. 22:59Anything else come up top of mind?
  7. 25:03Yeah, that relates a little bit, right? Could you tee on that?
  8. 29:05Of course, you've been doing this for so long and you probably got it down, but what kind of time do you spend or guidance would you give people on those kind of ratios or just generally the time to create something great?
  9. 34:01You've mentioned copy work at the front. What is that?
  10. 36:20Are there any kind of modern copywriters that come to mind that you love that you'd recommend?
  11. 40:53Yeah, anything on copywriting or writing?
  12. 42:29Have you ever thought about making yours public?
Ross 0:07 ↗
Sam, super pumped to have you on Content and Conversation. We're an SEO firm, but from afar, listening to My First Million, following your stuff on Twitter and X, it's very clear you're a great copywriter. And I don't know, you maybe don't talk about that quite as much, but I was excited to have you come on and talk your chops there. So thanks.
Sam Parr 0:28 ↗
I'm not a great copywriter. I'm a pretty good copywriter. I think I'm decent, and I know how to identify greatness. But you know, I can speak the language, I can identify the winners, I know what will work. But myself, I'm an okay practitioner.
Ross 0:44 ↗
I think you're underselling yourself, but you actually made me think of something that is probably just a good marketing technique. I find I'm like pattern matching success in the SEO world. I'm like looking at what works, and that seems like you've done that same thing with copy. I don't know if it applies to every single industry, but probably to some degree.
Sam Parr 1:04 ↗
Well, I think that what I did, I lived in San Francisco starting in 2012, and I was around like the Airbnb and Uber and like all these big companies that took off. And I was always interested in like my friend Noah Kagan and Neville Medhora, who are now my best friends. Before, I was just a fan of their work, and they would talk about internet marketing stuff. And like I always understood both this internet marketing world, which is sometimes scammy, sometimes totally not scammy, but sometimes it is, and then I understood like the Silicon Valley focus on the product, don't do too much marketing world. And what I did well was I combined the two. And there's a handful of us, like my friend Anu, who started Teachable, he was like that as well. And there's a handful of us who kind of understood both worlds, and that's kind of what I did well, I think. Basically like taking long-form, quote, scammy stuff, but applying it to the Silicon Valley mindset of being great at product. You know what I mean?
Ross 2:05 ↗
Right, yes, makes sense. Yeah, you did that very well. Sold The Hustle, and now on to Hampton, and doing a great job there. And something I noted and was looking up about The Hustle, I mean, obviously, I follow you on X and see your stuff on LinkedIn as well, and listen to My First Million. Your copywriting comes through and has a very unique flair that's you within that. But yet at the same time, I run a big content company. You clearly scaled The Hustle to something that sold in multiple millions to HubSpot. How did you scale that idea? Are there any specific techniques you used to kind of employ that across the team?
Sam Parr 2:48 ↗
Yeah, so basically my company was called The Hustle. We helped kind of pioneer, we didn't invent, but we kind of pioneered this newsletter model. Back when we started, people laughed at us. I remember an executive at some huge media company, so a founder of a huge digital media company that everyone knows, was like, dude, this is stupid, this will never work. And our premise was like, if we can get five or ten million people to subscribe to our newsletters, we can make like a hundred million dollars a year via advertising. And the way that you get people to subscribe is the cool thing about email is like it's a one-to-one conversation. So I just pretend that I'm writing only to Ross, but turns out a million other people are also going to read it. And that's how you build this really cool voice where you're talking directly to your friend. And I originally started the company by writing the daily newsletter, and then I also blogged a ton in order to get people to come to the website and give us their email. And so the fear early on was like, we are not going to be able to scale beyond Sam. And when I say we, it was basically just me. Like, am I ever going to get out of this? Or do I got to write this thing every day? And so what we did was, one, we hired great people. And a lot of times the people we hired, like two groups of people, one was like journalists and one was not journalists. And the not journalists did better. And what we did was copy work, where we would make them write, like me or my team would write the daily email, and then afterwards, for the first like four weeks or three weeks or something like that, the new hire would just have to copy word for word what we had sent the day before.
Ross 4:32 ↗
Makes sense. And that process essentially allowed, I'm sure, great person plus process of applying copy work is what you felt kind of helped the thing scale.
Sam Parr 4:44 ↗
Yeah, and because the premise of the company, so The Hustle was a daily newsletter, and it was sort of like a Wall Street Journal style content, but for like a twenty-nine-year-old, and mostly focused on entrepreneurship, tech, small business, that type of thing. But it was fun. It was like funny. Like we would make jokes, but they weren't, but you were still professional. Like, you know what I mean? Like the whole theory was like you can be silly and smart at the same time.
Ross 5:12 ↗
Yeah, no, makes sense. I mean, kind of a dovetail off of that, I saw you bring that up in something else, but you mentioned hiring great people. That is a good sentence. I'm curious if there's any more detail in exactly how you did that.
Sam Parr 5:27 ↗
Yeah, so testing. I hired lots of people who were blogging for fun or who were like, back then when I started The Hustle, I started working on it. Originally it was a conference, and the way that I made the conference work was I would blog about the speakers, and the blogs would go viral, and then people would hear about the conference and buy tickets. And then after doing that for two years, I was like, conferences suck. Let's, I have this email list of people, and I got them to come to my conference via content. Let's just make content the only part of the business. And that happened in 2016. And in 2016, Twitter was just getting popular, but it wasn't really that popular. Substack had just launched right around then. And I would find people who were like product managers or some job title at a tech company, but they clearly loved to blog because they did it in their free time. And I would be like, hey, come do this like for a full-time job. And that's how it worked. Or I would find these young kids who they did aspire to be a Wall Street Journal reporter or something like that. And a lot of our guys went and did amazing stuff like that. But I was like, hey, this could be like a three-year pit stop. And the reason it's going to be awesome for you is because let's say I had five hundred thousand subscribers, I would be like, you're going to talk to five hundred thousand people every single day, and your name will be on it. And you can like, I'm a stepping stone. So like you use me, I use you. Like this is a great trade. And so that's what we did. And I would hire these people, and I would always pay attention to, A, are they blogging and creating content in their free time? And B, I did this thing called the bottom fourth of the resume. So I would look at the bottom of the resume, like where they studied, what they studied in school, what their clubs and hobbies were. And then I would just be like, oh, you studied philosophy. Like, what was your favorite class and why? And if they could like entertain me, then I loved it. If they spent like four years studying something and they couldn't like tell me an interesting story, I was like, you're a loser, and I don't want to be around losers. Like you're like you're you're an uninteresting human being. Like I can't believe you just dedicated all this time and money to doing something and you aren't passionate about it. That's not cool. And so I would seek out these people that were like eccentric or just wildly passionate about the most unique, odd things.
Ross 7:44 ↗
Is there, I hear that, and I go to the instinct of many great writers tend to be this kind of insulated stereotype, is they insulated, introverted people that on an interview might not come through necessarily. But I don't know if that's also a copywriting attribute that you found, that they maybe are a little more extroverted.
Sam Parr 8:04 ↗
On our best writers, our best journalists or writers were weird people who I enjoyed, but most everyone else would not enjoy being around. Yeah, okay. Like they were a combination of, some of them were super hyper. So we had this one guy named Trung who now has like something like a million followers on Twitter. He was a nobody when we found him, and he was like, he would yell all the time. Like when you talk to him on the phone, I'd be like, dude, Trung, please quit yelling, because he would get excited. He was like so excitable. He would get so excited and he would go a mile a minute. Or we had this other guy named Zach, and Zach's probably the most viral guy on the internet in my opinion, like with articles. And he was always in a bad mood, and he looked like he hated you. And like he was really quiet, and he wouldn't ever tell you his opinion. Like you would have these personality types where the more brilliant and effective they are at their job, typically the more challenging, or it wasn't for me, but it was a lot of outsiders would be like, this person's a pain in the ass.
Ross 9:08 ↗
I can see that. That makes sense. So you kind of had the lens of being able to kind of see through those two differences, and passion could be a...
Sam Parr 9:15 ↗
But I liked it, by the way. Like we had a joke at our company, it was The Hustle, where you can let your freak flag fly. Like I loved hiring weirdos. I liked eccentric people, and we gave them, we were very clear about the canvas that they have to create on, and we were very clear about the rules, but they could go crazy within those rules.
Ross 9:33 ↗
Didn't, I swear I've heard Noah say something similar that you said you're your best friends with Noah. Wasn't that one of his kind of okay dork philosophies?
Sam Parr 9:44 ↗
It could have been. Noah and I are also, he's one of my best friends, and we're very similar where, you know, he's a weirdo. I think I'm kind of an oddball, and we love just being around eccentric people. And so it's, if you look at a lot of the people who worked for me and what they're doing now, and the same with Noah, we did a, we do, I'm, my world-class talent is buying people's stock before it appreciates. I'm great at that, and it's by finding people that are wacky.
Ross 10:12 ↗
So on that, one of the things I was thinking as you were talking about that process, it sounds mostly outbound. Like were you posting on Craigslist the job description or is it just like...
Sam Parr 10:23 ↗
Yeah, yeah, but okay, yeah, it's, yeah, like we had some, yeah, like we would, you know, the cool thing about our readership was like a lot of our people who worked at my company were readers. They were fans, so that made it easy. So that was like an unfair advantage. But yeah, so a bunch of them were outbound, and then, but then a lot of times like if you know this woman named Steph Smith.
Ross 10:46 ↗
Yes, I've heard you, I think I've listened to a podcast episode with...
Sam Parr 10:51 ↗
Yeah, so Steph's like an investor at Andreessen Horowitz. She's like this amazing woman who, she's still probably less than thirty, so she's got, she's doing amazing stuff in her life, and she's already doing amazing stuff. But she had a blog post called, uh, To Be Great, Just Be Good Consistently. And I was like, that's such a brilliant headline and brilliant article. And I just DM'd her and I said, you're fantastic, but you're doing this part-time. Do you want to talk about doing this full-time? And I would do that with people all the time. I would find people who are bloggers, and I would just be fans.
Ross 11:26 ↗
What was the company size of The Hustle at the end in people?
Sam Parr 11:30 ↗
We were going to do roughly twenty million in revenue, and I think we had a combination of freelancers and full-time people because we had some people who were overseas or whatever, or in Canada. And so we had roughly forty people who were full-time people.
Ross 11:50 ↗
Makes sense. I think when I hear you describe that, I think of, I'm not sure how much you listen to Bill Simmons and The Ringer, but it feels like a very similar process where, to my understanding, he's kind of like this draft junkie where he's listening to these micro podcasts, listening in on them, and like crafting, finding that perfect person. That you seem very similar to that in that way, and obviously both have worked out for you.
Sam Parr 12:15 ↗
Yeah, like if you look at like of the forty people, I bet you fifteen of them have gone on to start companies that have made them millionaires. And like, there's still guys that I keep in touch with that are now doing other stuff, and I'm like, hey, whatever you're doing next, I'm involved somehow. So it's kind of like having like little bets floating around. And I'll be like, look, like, don't you, like this guy Jacob Cohen is one of my guys who worked at my company. We hired him when he was twenty-one, and he's now only twenty-six. And I'll be like, dude, whatever you do next, you don't have to do it with me. You don't have to take my money, but please promise me that I get to, you ask me if you accept money or whatever. And so I have like twenty people like that.
Ross 13:00 ↗
Nice, that's quite the network you've got going. So you talked about headlines a second ago. I mean, something that stood out to me about My First Million and for sure at The Hustle as well is just your skill with that. There's many different places you're great at copy, but I read the headlines and it doesn't even feel like there's a formula there. There probably is from different variations of...
Sam Parr 13:23 ↗
There's less than you think, but I can explain a little bit.
Ross 13:26 ↗
Yeah, so I'd love to hear you, if you're comfortable, just talk through some recent ones. I'm not sure if you even kind of came up with them, but you probably have a sense. If that sounds good, I could kind of say it out loud and then hear you describe it, or...
Sam Parr 13:38 ↗
Yeah, describe it. And what you could do is if you go to, if you type in thehustle.co Sam Parr, you could probably find articles that I was an author on. And those titles, I wrote the headlines for all those because I don't always write the headlines, or I don't write the headlines for a lot of stuff anymore, but I teach people how to write them.
Ross 14:01 ↗
Nice, okay, makes sense. So I see this, 'Entrepreneur convinced investors to pour one million each into a brand new town.' Now that would be a good one.
Sam Parr 14:13 ↗
So the way that I, a lot of, so I do a few things with headlines, but the biggest thing that I like to do is I like to make the headline a sentence. And when I think of what that sentence is going to be, I imagine you're, so a lot of my content starts with the headline. And the way that it works is imagine Ross and Sam are sitting at a bar and they're like, I just listened to this podcast with Warren Buffett and it was all about being patient. And in fact, he mentioned how he didn't actually like, no, he mentioned that like he made a bunch of money at the age of forty, but actually the majority, I think like ninety-nine percent of his net worth, it actually came after the age of fifty-five. So that's like a sixty-minute podcast and you just remembered that one line. And so in my head, I'm like, well, the title needs to be like, here's how Warren Buffett made ninety-nine percent of his wealth past the age of sixty. And then I use the meta description or the sub headline. I use the word meta description because I'm like typing in WordPress, but the sub headline is like on Facebook when you post an article, you see an image, you see the headline, and then you see the sub headline. And then the sub headline is a play off of the headline. And oftentimes it's going to be continuing the conversation. So I'll be like, the headline will be like, Warren Buffett made ninety-nine percent of his net worth after the age of sixty. So the meta description or sub headline is going to be, The Secret? Patience. In this podcast, he dives deep on exactly how long it takes and what being patient means. So does that make sense?
Ross 15:54 ↗
Yes, yeah. So you're kind of continuing the thought from that. So is that how you're doing that in practice? Like you're recording a podcast, My First Million, for example, or even maybe you're not doing as much anymore, but you would immediately think back, like how would I summarize the thing I would tell people about that podcast in some...
Sam Parr 16:13 ↗
Yeah, but it's very cyclical. So like, it starts like, it's more of an art than a science, but basically I go into something with a headline in mind and then I start doing the work and it either is exactly the headline or deviates a little bit and I find a new headline. But I'm constantly thinking in terms of just how do I explain this in literally one sentence to someone that I'm just talking about this over dinner with. Do you know what I mean?
Ross 16:38 ↗
Yes, that makes sense. That's kind of a conversation. That's a good framing.
Sam Parr 16:45 ↗
Yeah, and then typically the way of importance is I believe headlines first, picture second, sub headlines third.
Ross 16:54 ↗
Interesting. Okay. And this is across networks or you're thinking about YouTube in particular?
Sam Parr 17:00 ↗
I am not a YouTube expert, so I can't, I will never, I can't claim to know anything about that. I'm referring to articles.
Ross 17:08 ↗
Got it. So this could be like The Hustle email newsletter would apply to that.
Sam Parr 17:12 ↗
Yeah, but I do think that if I had to bet, YouTube follows that same premise, but there's like the nerds on YouTube are so much better at this than I am, and I would not say I'm an expert on YouTube at all.
Ross 17:27 ↗
So you said number two is the photo, which I mean, I definitely see the thumbnail portion. Or is there anything about how you think about that for, I mean, it's not technically copy, but same kind of concept?
Sam Parr 17:38 ↗
Yeah, but you know, a picture tells a story, or was it a picture is worth a thousand words? So like it is sort of copy, but copy to me, copywriting is just taking what's in my brain and putting it in your brain, or it's manipulating, it's getting, it's manipulating you to feel or do the thing I want you to do, feel. Now what that means is I could be Martin Luther King and I'm giving a speech on why civil rights are important, and I'm going to make you buy into this cause. It could be I'm going to convince you to go on a date with me. It could be I'm going to convince you to buy something. It could be I'm going to convince you to join my company. And so it's all about taking what's in my brain, putting it in your brain, and getting you to do some type of action, whether that's feeling a certain way or doing something. And a photo is just one attribute or one medium to make that goal come to fruition.
Ross 18:36 ↗
Makes sense. Yeah, I see on one example from your articles on The Hustle that I'll screen share here on YouTube, you have 'Why Buying a House Is a Bad Idea' and then the thumbnail is you holding a little anti-house club image, which is pretty funny and good.
Sam Parr 18:53 ↗
And then scroll down. So scroll down and go to the, like, I'll give you a good one. So type in, type in The Hustle Soylent. That one went crazy viral. I could do a breakdown of that one. And then after that, I'll show you another article. But the preview image on this one was that before and after photo. But yeah, and like they're not that different, but before and after photos, even if they're not different, they are, they're very catchy. But the headline on this one performed well. And in fact, I believe when I did it was the Soylent. So right for the listener, this is an article about how when Soylent, which is basically like SlimFast for nerds, it's like a drink that's like a food, it went popular five years ago, I don't even remember, ten years ago, and I had a guy live on it for thirty days. And the headline was, 'What Happened When I Went Thirty Days Without Food.' However, that was for social. The search headline said, 'Soylent: How I Went Thirty Days Without Food,' because when people Googled Soylent, their website came up number one, and then we came up number two. And that worked really well. We got so much traffic on that one. And then the sub headline is, 'I spent the last thirty days eating nothing but Soylent, a new age power meal replacement. Why would I do something so stupid? I'll explain. But first, if you aren't familiar with Soylent, here.' So when this got transferred over to HubSpot, they kind of screwed up that part, but that's like the part where the sub headline is continuing the story on the headline.
Ross 20:28 ↗
So in your course, you mentioned the AIDA model. Are you consistently, like no matter what you're doing, referencing this model? And like, is it present here? Is it in your post structure templates?
Sam Parr 20:40 ↗
It's, yeah, yeah. So the way that it's present here is the photo is attention grabbing, and so is the headline. And then the interest, and the interest is the sub headline. And then oftentimes I'll, this could have gotten screwed up a little bit when they transferred. So we used WordPress. It looks like this got transferred over to HubSpot. But like, I'll be like, 'Here's how you can implement this as well,' or something like that as like a desire and action. But yeah, I think of attention, interest, desire, action oftentimes. But basically I'm always thinking, how do I get your attention? And here's another one. So on The Hustle, type in Pandora. This article was the very first article we wrote. I think it was the very first one, but it was close to it. This got something like, no, can you do Pandora's founder? No, Pandora founder pay something where he convinced his employees to work without pay. Is there? Yeah, there it is. So this was one of the very first articles I ever wrote. I think I did, I wrote it in the summer. I can't see it. It was the summertime of like fifteen. And this article got a million views, I believe, in the first week of us in business.

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APA

Parr, S. (2025, January 27). How Sam Parr Mastered Copywriting for a $27M Exit [Interview transcript]. Content and Conversation. CEOInterviews.AI. https://ceointerviews.ai/interview/3016544/

MLA

Sam Parr. "How Sam Parr Mastered Copywriting for a $27M Exit." Content and Conversation, 27 Jan. 2025. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3016544/.

BibTeX
@misc{parr2025_3016544,
  author       = {Sam Parr},
  title        = {How Sam Parr Mastered Copywriting for a $27M Exit},
  howpublished = {Interview transcript, Content and Conversation. CEOInterviews.AI},
  year         = {2025},
  month        = {jan},
  url          = {https://ceointerviews.ai/interview/3016544/},
  note         = {Speaker-attributed transcript with timestamps}
}