521 How Sam Parr Builds Businesses

Sam Parr founded The Hustle, which he eventually sold to Hubspot for tens of millions of dollars.

The Hustle was born from a conference he started, called Hustle Con, that showcased non-technical startup founders and their strategies for success. The Hustle ended up garnering an audience of millions of subscribers and was able to operate profitably as a new media startup that was not overburdened by outside capital

In this interview, Sam and Aaron discuss the early stages of Sam’s career, his tips for selling, and finding meaning after selling your company.
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Sam Parr’s Challenge; Monday night, make a list of 50 people who you wish you could get in a room with and develop a strategy for reaching out to them consistently.

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Watson: Hey, what's up, you're going to love this interview with Sam Parr, the founder of the hustle and the host of my first million.
We discuss. The stair-step approach that Sam has taken to selling consecutively larger deals throughout his career. And a little bit about the scatterbrained all over the place, entrepreneurial mind and how to lasso it.
So, uh, do you have the easy name to pronounce of like any entrepreneur. 
Parr: I do. It's good. Sam, Sam Parr. My full name is Samuel. Joseph par, very Catholic, very, uh, Midwestern name. 
Watson: I really like the only error that one would make is giving you one R instead of two on last name. Right? 
Parr: It doesn't happen a lot.
It doesn't happen a lot, but yeah, I've got, I've got a good, uh, easy. 
Watson: I feel like that's, um, that's definitely an advantage. It's not like, I've know another Sam par, but it's simple and distinct enough that everyone gets it. Right. That's good. For a branding standpoint, I struggled. There's a country singer by the name of Aaron Watson.
Who's like considerably larger than me. So I have to, you know, start figuring out and I can't even wear like a crazy hacks. And I'm just like the Aaron Watson that doesn't wear a cowboy hat. 
Parr: No, I'm lucky. I don't know. The only say empire. I know of there's a state park in Illinois called Sam Parr state park, but the guy was like alive in the 18 hundreds, so I'm good.
Watson: Nice. Um, so we have a concept on the show. We'll call it deal climbing, uh, you know, uh, other folks have, have different names for the same idea, but I feel like it's. Uh, helpful framework, particularly for people that are just ambitious, they're trying to climb. And if they're climbing from doing $10 deals to a hundred dollar deals where they're climbing from doing $10,000 deals to a hundred thousand dollar deals, it's the same stair-step approach that everyone has to go through in some way, shape or form whether or not they're even in a sales position position, which is learning how to not only deliver more value, but get someone to sign on the line that is.
At a higher ticket price. Um, you started off selling hot dogs and, uh, to my knowledge, the biggest deal that you recently closed was the selling of your company for tens of millions of dollars. And I don't know if you remember, he actually commented on our video where we like speculated on how much you, you sold the company for when that happened.
Um, but. Uh, we were like trying to back into like what the minimum was and you were like, not wrong, but not right. Like you were like, basically like you're, you're in the, 
Parr: what was the minimum? What number did you say? 
Watson: Um, I think we had said that it was over $20 million and then like shortly after I saw Tucker max commenting on a Twitter thread that someone had made the same speculation.
He was like, that's not quite. 
Parr: It was for sure. Over $20 million. So that's, I'll say that it was, yeah. And also I own a lot of HubSpot stock and the stock market is really shitty today, but, uh, Yeah. At its peak, it had tripled, uh, from when we are well, uh, maybe 2.5 X from when we'd sold. So, and it, but I did that like within weeks or months of us selling.
So the price kind of almost changed rather significantly. 
Watson: So, um, we're going to get into that cause it's an amazing thing. I'm not particularly technical. I'm not going to write the code that like builds the next software product, but having a substantial stake in a technology company is, uh, uh, a way to.
Draft off the trends of technology generally, but let's, let's go back. You were selling hotdogs, you had to figure out how to get someone to, you know, how much were you selling hotdogs for? 
Parr: So my prices in the, in the afternoon were different than my prices in the evening. Surge price evening prices you double because it's drunk people.
So evening prices, eight to $10, $10 for a polo, a quarter pound pole, or a third, a pound pull a sausage with a drink. So 10 bucks, and then in the day half that. And so 
Watson: you were, uh, you know, after you. Decided to really make the jump and try to start a company you were before getting to the hustle. What were you selling where you're selling yourself as a freelancer?
You selling yourself as an employee, 
Parr: you know, So when I was in college, I started tinkering with the internet and I made like an online store that was making like a thousand dollars a day at one point. But I didn't like do all the things correctly. Uh, like I didn't like, like, I didn't know anything about filing taxes, getting business license and like, things like that.
And so I kind of shut it down. The lawyers at my college were like, yeah, you kind of need to start over and get this thing. Right. But like, I was like, well, all right, I feel you, but that's kind of cool. I learned how to. Tens of thousands of dollars selling stuff on the internet. And so, um, I basically left school because I cold emailed this guy who owned a company called air bed and breakfast in San Francisco.
And I was like, I think this thing's going to be huge. I'll can I come and join you? And he said, yeah. And I got a job offer at Airbnb, but back then it was like brand new and I get there and I dropped out of school, moved up. And I got the offer taken away because I had gotten in trouble, um, and had been arrested before I used to be, uh, not the most awesome person.
And I did some stupid stuff that I regretted and they, I lied about it. I didn't tell them that I'd been arrested. And they were like, dude, you just told us, like we would have, we would've it's okay. But you lied, we can't hire liars. And they're totally right. So I got out there and I had. So I met a guy and we started a company and we sold it.
We made, I made like a hundred grand from it, nothing substantial. What were you selling that company? It was a roommate matching, uh, app. It started as I did it in like in person, I would basically host like roommate parties. And so everyone at that party had the same preferences. You know, they were like a single person by themselves in San Francisco, but getting a one bedroom was prohibitively expense.
And so they would help people team up in groups of twos, threes, and fours, and get an apartment. And we've made money from that. And 
Watson: what, like what was being charged for that service? 
Parr: I don't remember entirely, but in the ballpark of three or $400 per room 
Watson: to step up from selling hotdogs, what was similar and what was different from those two sales?
Parr: Uh, the, uh, $10 and 300. Uh, it's mostly the same, um, in my experience, um, it was mostly the same. The difference though, is the value that what I learned is like, it's about it's about value given. So the value you get from one meal, isn't significant, the value that you get from. Finding a place to live is quite high.
So the name of the game is provide as much value as possible. And just still just take like a small take of that and your take will be higher if it's a higher value thing and 
Watson: theoretically a roommate's going to be impactful for a year. Whereas you're saying the meal's gonna be impactful for an afternoon or anything.
Parr: Exactly. Yeah, yeah, yeah. So it was about how much value you can provide and you just take a fraction of that. So the reason the sale was easy. $300. It was like a no-brainer like people and we kind of had an honor system. We just said, find a place. And afterwards, if you find it through us, call me and we'll come pick up money.
And it was so simple. But then we, uh, as we made money, we transitioned and we made it an iPhone app. So it was kind of like Tinder, but for roommates, and this was right when Tinder was like, barely. And like, which is stupid. We should've just done Tinder for Tinder. Right. Uh, but we did Tinder for roommates and, uh, yeah, it, it was, it was, it was hard, but okay.
Of, uh, it was a good first swing. I 
Watson: think you sold that company. You made a hundred at that, uh, about a hundred thousand dollars or so you probably, 
Parr: I basically got like a good job and with bonuses and I saved my money and I was there for one. And that was pretty much it. 
Watson: So selling that company, that's a substantial jump up from selling something for hundreds of dollars.
What was the difference or what was the kind of gap there in terms of selling a 
Parr: company? Um, I think I was devalued, uh, undervaluing myself. I think, um, I started thinking in terms of hundreds of thousands of dollars. And I, I was like, oh, that's a ton. What I didn't understand until actually like this year is that big companies need people like me, people who move quick and make stuff because big companies struggle with that.
And I didn't understand how valuable that was. And so. The biggest thing that I did then was I probably didn't do a good job of like negotiating. Um, I was pretty bad at, I was pretty bad at negotiating and probably still am. So now I have people that do it for me, even if it's just like my wife, she's good at it.
But, uh, yeah, I undervalued myself I think for a long time. 
Watson: And then did you start the hustle shortly 
Parr: after that? No, I left that place after one year and one day I was 20. Some age between 23 and 25. I think I was 20. I don't remember. Uh, it was in 14, so it was 24. And, um, I was like, I need to find something to do.
I don't know what I'm going to do, but I'm going to run this event called hustle con and hustle con was like non-technical entrepreneurs, giving talks and I was. At we're at, at best I'll break. Even at worst, I'm only going to lose $10,000 hosting this event, but hopefully I'll meet someone who I could partner with or something like that.
And I hosted this event. I decided to do it. I made the decision to host it on May 1st and I launched it like it became an event on like June 14th, or I forget the exact time, but it was six weeks. So at six weeks from decision to it going live and it made like 60 grand in profits. And it made profit because I created an email list and I would write cool stories about the speakers.
And I was like, huh, that's kind of cool. I didn't expect that to happen. So I basically just lived off that 60 K for like eight months and traveled the country on a motorcycle. And then I did it again and I did the same strategy of just creating a newsletter running about the speakers. And this time it made like two to $300,000 in profit.
And I was like, all right, cool. I dig this. Um, I'm not going to be a conference person. I don't like running this business. This is hard, but I've been able to get a lot of people to notice my writing let's create a media company because I L I, if you see on my walls back here, I've got. Uh, I'd like three or four of them are media people and I've always liked those guys.
I was like, well, fuck, they could do it. I can do it too. So I decided to start a media company and I just researched what the best way to do it was. And I settled on starting with email and that was, um, the email thing went live, uh, uh, basically four 20, 2016. And so 
Watson: you were selling tickets to those events that you had to also be selling sponsors?
I would imagine. 
Parr: Uh, yes. And years on the newsletter as well. Well, it took like a year to like, get real sponsorship revenue, the way sponsors work. They want to say it, you could pull it off. So I was just living off the ticket revenue to be honest. But, uh, yeah, so like, by the time we had done that, maybe like once we got to like our third event, we were doing three or 400,000, I think in revenue.
And it was like half sponsors have. And then we launched the newsletter and we had, we got that newsletter already had like tens of thousands of people just from the conference and we just kind of switched it over. And then through a bunch of blogging, I got us to a hundred K really quick. So basically we went from like zero to a hundred K on the.
And we started adding ads. Uh, I I'm going to ballpark the numbers. We started having sponsors in the newsletter, some number between 50,000 and a hundred thousand. I don't remember exactly, but I do remember, uh, I was my goal with staff and all the events that we were hosting. We were spending like $25,000 a month and I was like, I'm going to go out and get sponsors for $30,000 a month.
And that $5,000 profit will give us enough profit to hire a sales. And so I did that. It took me about two months and I did that. And then we hired a salesperson and like within two months that went to like a hundred thousand dollars a month, uh, in, in monthly, uh, ads. 
Watson: So it's great to hire someone who can move the needle like that.
But as you were just selling enough to keep the business afloat, what was the same about all these past sales, hotdogs, tickets, uh, roommates, and what had to, what was new that had to be like. 
Parr: Um, the same as I always kept things real casual. And as you grow and get bigger, you actually, they're not, they're not casual.
So we've closed multiple seven figure deals at the hustle. Those are not casual. Those are process driven and those are really hard. But when, when I was, I would sell, like when I first started, I would sell something for my first sponsor was law trades and wealth front, and I charged him a thousand dollars and it was just like, kinda like hood, like.
Kind of like, it was kind of like done like a street style deal where I'm just like, dude, just give me a grant. And if it works, you advertise again. If it doesn't, you've only lost it gray and just like, Venmo me. I like, it was like really like not done the right way. And um, maybe they even sent a check. I don't remember, but they like were like, yeah, whatever fine, dude.
We'll, we'll give you a shot. And we did that. And then eventually I was like, all right. What's an N they're like, all right, send us an invoice. I'm like, what's an invoice. So I had to Google it and I like got some invoice software and it said, Invoice 0, 0 1. And I was like, oh, screw that put like 0, 0, 3, 5.
Uh, like, so it's like, this is our 36 and I don't want them to know this is my first time I've ever sent an invoice and then like, learning, like, alright, great. You ran the ad. We'll pay you in 30 days. I was like, wait, what? You don't pay me right away. That's crazy. Um, so like learning about that was different.
Watson: But I, I feel like that's the only way to do it. So I almost have a, I have a very similar story in the first year of my company. Uh, one of the fortune 500 companies here in town reached out to help with, uh, producing their internal corporate comms podcasts. And literally the exact same thing. They're like send us an invoice.
And I literally like it's invoice generator.com or.net or something. And it's literally like the exact same thing. It's like this can't be 0, 0, 1. We're going to like put a 1, 2, 3 or something. And they're the 
Parr: biggest. Yeah, that's what I had to do to look more legit. And then at first, even to get sponsors, I put like Ford in there as a sponsor, even though I've never talked to them in my life, but I was like, man, if they see Ford, so there, they're going to know we're legit.
And that's probably illegal actually. But. Yeah. So, 
Watson: but so maybe not recommending that to someone getting started, but the like pure hustle of like, just get a deal in the door that is legitimate, that is paid for in some way, shape or form, even if it's not super process 
Parr: driven. And it was not, process-driven 
Watson: having also conviction that, like, there's something there, like it wasn't like you had a pretend tens of thousands of persons list.
You had a 
Parr: meal list and we were under again under sold hard. So early on, I was like, I don't care. I like. I'm like guys, I even said to him, like, we're going to send your email 50,000 people pay me whatever you want. Pay me two weeks after you could see the clicks. Whatever's fair. Just do it. I don't care.
And that's what they did. And it came out to be like, oh, I could charge like 20 to $30 per CPM. So like, after like the first 10 clients, the next one, I was like, all right, it's $25 per CPM. And the results for our past clients are here. You could see them. So that like, it was like really. The the early folks, and this is actually good.
If you're an advertiser, you find people like me who are early and you take advantage of them because they're going to take, you know, it's a mutually beneficial relationship. I'm getting someone to trust me, even though, like there's no necessarily a good reason to trust me because I'm a newb and they're going to get a good deal.
So it's like a really mutually beneficial relationship. So I was happy that they were willing to do that. And they were happy that I gave, they got under. Advertising. So it worked out really well. We both won. It's kind of 
Watson: rare that, but that's a really good framing of it is, you know, a venture investor or some just any like a skilled investor in financial markets is looking for those young upstart companies that haven't necessarily been realized or appreciated yet.
It's rare that you think of media buyers in that way, but it really does that. It really is kind of what the elite at the JOL Republic 
Parr: do it. If you're a good media buyer, that's what you do. You find something that has a small following and you buy one year's worth of that. 
Watson: And then you get it on the backend with all the growth 
Parr: that they're going to.
Exactly. It's, that's one of the best ways to do it. You'll get screaming deals that way. I 
Watson: think that you would be fantastic if that was like the position that someone just put you in because from listening to my first million, like you put me on to, uh, Huberman and Hormoz easy who are literally like my two favorite, uh, shows that like must listens now.
You definitely have, and it probably comes from producing media. Uh, ability to appreciate when someone's kind of got it before the rest 
Parr: of them are for sure. Yeah, yeah, yeah, yeah. I definitely have that. And a lot of people have that, but when you, when you see something that is like interesting and dynamic, I mean, if you look at the people that we've hired, we've hired a ton of nobodies and they are not.
Very much somebody we have about five people that are like big shots now. And when we hired them, they didn't even have a Twitter. So we've done a really good job. I think it's spotting talent. Um, and so, but a good media buyer should be good at that. 
Watson: So after you started getting advertisers for the hustle, the next things that you sold in my recollection where the trends groups, that was a kind of research paid community.
Parr: Um, but that didn't happen. Two years. So like our ad business was doing like, I don't remember exactly 500,000 to a million dollars a month. Um, I hate the ad business. I hade because they limit, they limit what you can say. And I don't mind losing money in order to have free speech. But the problem was is that my coworkers who were selling the ads were quota carrying.
And if I said like, you know, F Goldman Sachs, I'm writing, whatever I want. I have no problem hurting Goldman Sachs. I've got no problem hurting myself, but I, it pained me that Katie was now going to lose money. So I was like, Ugh, this I'm in this conundrum. So I really didn't like. And so we decided to launch trends like two or three years into the business, and that was a paid subscription in a paid community.
And that took off like that did really well right away. And, uh, I mean, it did kind of well right away. 
Watson: And what was new about that sale? Cause it's recurring subscriptions, um, which is different than a lot of the other things that you've articulated. Although I guess an advertiser relationship could be similar, but it's, you know, a consumer sale.
What, what did you have to learn to be effective there? That wasn't necessarily true. 
Parr: Past sales. So with selling big ad deals, you know, we would S I started selling a thousand dollar deal. Then my team started selling tens of thousands, hundreds of thousands, and then millions. And the time it takes the bigger, the deal, the longer it.
And, uh, that's what I learned. So like, if it's like a $500,000 deal, there's like many meetings, many process, you have to use a lot of jargon, you've got to fill RFPs and you got to fill, you gotta become an official vendor. You got to get approval for this thing. And that thing, and that is hard. Enterprise sales are hard, which is what we were doing with a $300 deal.
Um, I learned a lot about pricing. Two major things there. One copywriting, I think is the most important skill. Not only in business, but life, a good copyright. If you are, if you learn copywriting, you'll, it'll help you meet a wife, a husband like copywriting basically means understanding what motivates people and manipulating them to do what you want them to do.
So. Um, I want you to, I want, I want, I want to convince people slavery's bad. I'm going to use like what motivates other people. And I'm going to like, make them feel and agree with me that it's bad. I want them to buy this product. Then I'm going to appeal to their emotions and appeal to their logic and get them to buy this, you know, w whatever I want to meet this woman, I want her to like me.
I'm going to figure out like, what motivates her. I'm going to try and get her to like me. That's what copywriting basically. So I think everyone should learn it and I am a hardcore copywriter and I use that for trends and so trends. Copywriting all. That's what sold it. And we actually had $50,000 in pre-sales just from like a word document that explained what it was and it killed it.
And the second thing that I learned was pricing. So the 2 99, we charged $300. At first. I should've charged either $99 or 2000. 3 99 or 2 99 is no man's land. That's that's bad. You want to charge either cheaper because 2 99 is not an impulse buy, but the person paying 2 99 very likely would probably be willing to spend one to $2,000.
And so it was a bad pricing, but we scaled that business nicely, regardless, even though that was a pretty huge mistake. That was almost a, that's almost a game changer mistake. And 
Watson: when did you realize that? Because I I've looked at trends and it's still. Roughly in that price range. 
Parr: Yeah. And for two reasons, well, one day when we sold like HubSpot doesn't care about revenue that we make.
So frankly, I think we should, I actually am going to talk to them if it doesn't be like you're making $99, just make it cheaper. Um, but yeah, I, if I was, if I owned it, it would be different. Um, 
Watson: and then. Was there another big sale before selling your company to HubSpot? Or is that the kind of here? 
Parr: No, we had this thing that we were about to launch called trends guides, and we are charging, uh, I forget the exact price, but it ranged from 10, uh, two to $10,000.
And it was a research thing. And so basically companies who wanted to know, so Trent, the hustle tells you about news trends tells you about specific trends and businesses, and then guides was one level up. And that was like, we're going to tell you about very specific niches and, and one very specific business model in that niche.
So if you want to, if you're a media company, You pay 10 or 20 grand a year and we're going to break down like how the hustles doing blank. So you, big media company at Warner can just like, know exactly what they're doing and stay on top of it. And then you can meet the other buyers of that. So you can meet like the cool young media companies.
You can meet the older media companies, your peers, and we can all talk about the tactics that we're learning. So, um, and it's almost like a gardener. And so we actually, pre-sold a bunch of those. Um, we had, um, probably, I don't remember exactly tens of thousands or a hundred thousand in pre-sales on that.
And, uh, that was mostly the same as selling a 2 99 thing, except the only differences is that, uh, the buyer had to get some type of approval. So 
Watson: I guess, I guess we should. Tell the story of sound to HubSpot. And then I have a question that we'll come back to this trends thing. Cause I think that there's some meat on the bone there, um, selling your company second time, selling a company biggest sale that you've ever done.
You're not going to give me the number here, but we can say tens of millions of dollars in a life-changing personal sum of money. What? Yeah, but you know, what, in what ways was the combination of these past sales? I'm sure it was very process-driven like these seven figure advertising sales that you did.
What to, what degree did you have to, um, I don't know, utilize those versus learn new skills. 
Parr: I made one huge mistake early on and I've benchmarked the price. Someone was like, what number are you looking for? And I said, these companies typically sell for two and a half to six times. Obviously, they're going to start at two and a half.
And right when I said that, I was like, fuck, fuck, fuck. I can't believe I said that. So that was the big mistake, but I did one thing really well, which is I've been courted a little bit to sell and they emailed me and I was polite, but blunt. And I said, they sent me an email saying, Hey, we want to partner with you.
And I'm like, but I, and the title of the person was in corporate development and I'm like, Hey, look, let's just cut to the chase. Are you wanting to buy us? If yes, say yes, if no. You know, great. We can talk about something else, but if yes, um, I'm going to email you a list of all the reasons why you shouldn't buy us.
And if any of those are red flags, we can continue talking and they go, yeah, we want to buy you. And I go, great. Here's a document that explains everything. That's bad about us because I know you most likely know what's good about us. I'm going to show everything is bad. And if that's a deal. Nope, no problem.
And I sent that to them and they go, no, these are the, none of these are deal breakers. So I was like, boom, got them. And so after that, I was like, they they're going to buy us. The only thing is pricing. And that 
Watson: also takes their potential negotiating leverage off the table for later when they'd be like, oh, well, we just found out that you guys, you know, don't wear hats when you 
Parr: write or something.
Got it. That's a good one. I showed them. I got like, like I like showed them all the bad stuff right away and nothing was that bad. Um, but I, like, I was like, I don't want to get any, I want to make you say no fast where'd you 
Watson: get that strategy from? Cause you study all the different entrepreneurs, you read the biographies, where'd you get that?
Parr: I made that up because, um, it's kinda like when you're dating in your thirties, like you got friends that date in their thirties, like on the third day, they're saying like, Hey. Do you want to have kids? And do you see me as, as the woman or man that you want to have kids with? And when you have, like, when you, when you got, uh, you know, it's not, you're not 22, you know, you can't just like, kind of.
Yeah. Spend six months and like, oh, I hope it works out when you're, you know, like 37 years old and you're trying to meet a mate. It's like the second date. You're like, Hey, so are you looking for marriage? Are you looking for kids? How many kids? Like you get down to business? Cause you both, like, you're both active.
And so I was like, I'm going to use that approach. So I'm just going to be like, Hey, cut to the chase. You're trying to buy us. Okay, great. Here's why we suck because you still want us. And I just wanted to, I didn't want to waste time. So. 
Watson: Going through that arc, this is something literally light bulb only came on as I was talking to you with you.
Um, there's all sorts of stories like this through business history, where someone will build a company, they will sell it to a larger company. And then, and I'm not saying that HubSpot is mismanaging the hustle, but they're not focusing on trends as a business. And, you know, Michael Rubin who, uh, you know, as a, as a minority owner in the 76 ERs and started fanatic.
Like sold his company and then rebought it back from the company that acquired it or rebought back part of it to run the company. When he, I would, I 
Parr: would buy back, I would buy back the hustle, the, 
Watson: the entire hustle or specifically trends, 
Parr: whatever they would, let me, whatever they'd be willing to sell.
Watson: Interesting. Cause I w I have to imagine that. If trends, revenue isn't particularly meaningful for the bottom line and they're selling like CRM ops software. So there isn't a super linear, like cross selling connection between those two communities. I have to imagine that if you could almost like step away from the nuts step away from the newsletter and the podcast, but know that that has this whole infrastructure behind it.
And just hone in on the repricing, the copywriting, the thinking through the strategy there, that seems like a. Uh, if I was, you know, placing a bet, I don't know, above 10 to 20% probability for 
Parr: sandbars future, I wouldn't, I can crush that business and I, I'm still gonna launch that one day, like a research business.
I can make that into nine figures in revenue for sure. And our advertising revenue would have been tens of millions of dollars this year as well. Um, I don't regret selling though because given the information that I had at the time and the mindset that I was in at the time and the goals that I had for myself, Is the right move.
But yeah, we would have been way bigger now in terms of revenue. Um, and, uh, I could crush trends. I could run that business really well and I'll do it eventually. Uh, 
Watson: what is a major takeaway from Ted Turner? I know he's one of the media icons that you've got. What's something that you've just internalized from.
Parr: Move really fast. I think that like small companies, we really only have two advantages over big companies, which is speed and focus. Um, and he would move really fast. He also, um, what's an outsider, so he was from Georgia, but he, you know, uh, time Warner is, uh, the time Warner center is like in the heart of Manhattan.
And so I think people dismiss them because they kind of talked with the Twain and was from the south. And so I was really inspired by how this outsider can just do it. He also just kind of clawed his way up. He started with billboards, he owned a really small billboard. And then he bought a small radio station and then he bought a local TV station.
And then after like 25 years, he created CNN and that took like 10 years to work. So it took a long time. So the biggest thing is, um, if you're gonna do something, it's a pretty good competitive advantage to be willing to dedicate 30 or 40 years to it. I've. 
Watson: So I've done hundreds of podcasts, interviews like this.
I've spoken with so many different entrepreneurs, all sorts of different industries. Um, devouring that information probably to a fault, probably to a fault of like taking as many actions that I needed to particularly early in my career. Um, but that's just like the way, I don't know if it's school or the way I was parented or whatever it is, how I've tried to figure out the lay of the lands that I could make good decisions.
And I'm not saying that you didn't take action, but you are similar in that you have. Like your whole show is just, Hey, I was like researching this obscure business in order to try to understand how these things work. Do you get bamboozled when you talk to other entrepreneurs who that doesn't even like really cross their mind as part of their process for getting things going?
Parr: Not exactly. Because for two reasons, one, I recognize that there's a lot of ways to get it done. And number two, I think a lot of the people who say they don't, they do a lot more than they, they, they, I think in China, I have a whole, my here's, I have a very strong philosophy on that. And so there's a few things going on here.
So I researched and read like crazy because a, I want to, I want to not repeat the same mistakes that they, that they made and you could actually find recurring mistakes and was like, all right, boom, don't do that. So I'm like learning a strategy to there's this phrase that you are the average of your five, most friends are your five best friends.
I feel like I'm the average of the five people I read and think about. And so that definitely helps me three. If I study how other people do things and the big things that they've done, really innovative things that done's done, it breaks my mental frame. So for example, When Roger Bannister broke the four minute mile, um, people were like, oh man, you did it.
And then like within five months, like four other guys did it. And there's a reason why, which is when one person sees what's possible. They have faith and they have hope and they work a little bit harder and it. Makes it the norm, the reason why I lived in San Francisco, I have a bunch of friends that are like huge deals in terms of business.
And at this point it's regular to me. And so when I think about what I can achieve, it's no longer can I do that. It's more so just like, do I want that? If I want that, I, I can do that. I can pull that off because it's just normal, you know, it's like, uh, Normalized. And so that's why I research like crazy and learn from other people.
Um, and also it just inspires me, which is like a little fluffy, but I get pumped up and I get inspired. It makes me feel good. And 
Watson: probably speaking to the, I mean, anyone that's stuck around this long into the interview is to some degree shape or form similar in that they're trying to figure out what other people are up to, 
Parr: but, and you also, it's, it's fun.
I find it fun. It's just fun for me. Yeah. But 
Watson: when. So you said that you think that folks that say they don't do that or don't acknowledge that maybe just don't realize it or don't think about it that way. Can you elaborate on 
Parr: that? Yeah. So my friend Goggin started this company called Udemy, and now he has this new company called Maven.
I heard his, his co-founder Wes. Alicia. Yeah, she's lovely. She's great. And Goggin used to tease me. He's like, dude, you research so much. And I was like, bro, I go. What have you dummies competitor? I forget their name. It's a big course company, but I was like, Hey, what was Teachable's revenue? And, uh, he told me and I go, why did they do so good?
And he, I was like, you know, what were they different than you to me? And he told me, and I go, uh, what about, uh, your Udacity? How are they doing? And he, and he knew exactly like how they're doing and what the revenue is. And he goes, he's like, but the reason they're different from us is they're going after this.
Well, bro, you're like researching like your competitors, like, you know, like you're, you're on top of it. Like, you know, what's going on. So like we're kind of doing the same thing. And he was like, well, I didn't think of it that way. So I was like, well, it is, it is the exact same way. So like any, a lot of co founders, they'd like, if you're beyond me, like, you know, like what impossible is doing and you know why it's good, why it's bad, why it's different.
Why could be great, whatever you're you are on top of it. So one of the time, and so it's the same thing. 
Watson: So one of the. Timeless lessons that most entrepreneurs have to learn at some point is to focus and to not be trying to like do these 10 different experiments and get all these things. These things done when one thing is working and if you just quadruple down on it, your revenue's going to grow sales, cures, all, all those kinds of things.
Inevitably, you had to learn that lesson at some point over the last. Decade as you were building companies, but now, you know, you have the podcast, you have whatever the kind of out is or structures within HubSpot that, that has you sticking around. But how have you tried to manage your focus in a situation where there isn't maybe the same financial impetus to have to get it figured out?
And you actually have like the resources and time to go run all these different experiments and explore. 
Parr: I don't do that many experiments, even. I know a lot of people think it seems, they think it seems that way, but basically when I was running the hustle, we didn't even have a, uh, like a Twitter page for like the first two years we had a meeting every single week, it was called the numbers meeting and it was.
Let's talk about our email list grow by 3% this week. If yes. Why? If no, why? It's like all I cared about. That's all I cared about for four years. I was very, very good at focus. I was like, Nope. We're like, uh, her Keller, the guy starts Southwest. He was like, we're going to be the cheapest airline. And someone came to him and goes, Hey, should we offer a salad?
And he goes, is that going to help us be a cheaper. And then you'll note, and then he goes the, no, we ain't doing it. Like, it's all about the low cost airline. So I got really good at that saying, and you just say no all the time to be honest. Um, and you just focus on that one thing. And, uh, that worked really well because if you look at it for a lot of people, There's a lot of people now, like Warren buffet or something like that, or whoever, some tycoon who is wealthy and they've got their hands in lots of different stuff.
But if you try to, like, if you backtrack and look at how a lot of people made the first amount of wealth that they were able to snowball, I mean, getting that first nut is like a really big deal. That first thing typically it's like an 80 20 thing where it's like, maybe you accumulated a little bit from the third thing, but nine out of 10 times, most, most all of it came from.
Um, and so I recognized that and I was like, all right, I just gotta focus on this one thing that will give me enough money where I don't ever have to worry about money again. And after that, then maybe I can like expend time exploring and having fun. And then I'll find the thing I really liked and then go all in and focus.
Does anything that's worth doing it's worth overdoing. I think we've got to focus. Um, and you just basically have to say no to everything. And after 
Watson: you'd accomplish that though. So, so we, uh, interviewed, uh, uh, entrepreneur had a very similar story. He built a robotics company over eight years. And it was day and night.
It was everything. It was the focus to the point that he made it. It was like some crazy thing, like six years without losing a single employee because of just the culture that he'd built and the maniacal commitment that he had given to what he was building. And then he sells the company and is a drift, like literally feels lost because in your case, I didn't have the 3% meeting where I know that it's this number that maybe doesn't define whether or not I have a good week.
Significantly influences whether or not this was a good week for us. Like, did you experience any part of that? Even though it was like, he, he, I think he sold the company for $275 million or something like that. Like, it's still this loss of partially how your identity was structured, partially. How you 
Parr: kind of, well, I still do it.
So like the first year after it's only been a, it's been a year and a month or something since we sold the first year, I was like, I'm just going to focus on my. And so it was all about, um, like I had body goals, so I did the same thing. I just transferred it to a new, um, I was like, I'm not going to focus on business at all.
All I'm going to do is the podcast. And all I'm going to do is. My body fixed my body. And then I started angel investing and then I set goals. I was like, all right, we got to deploy this much capital with an inside. Did the same thing and the same thing. Now I'm in Explorer, exploration mode a little bit where I'm just like following my heart.
I'm just doing whatever seems fun. If I like, it's like a dog walking down the street, they like catch a smell. I explore it. So I'm reading a lot. So I'm chilling because I know that. Uh, um, you know, like, have you ever met a veteran? Like, uh, like a soldier? Yeah. It's got some of my family and a lot of times the people that I've hung out with at least they'll say it was really hard.
It was scary, but man, I miss it. And that's how I feel where I'm like, um, I was, I was exhausted. I was tired. I needed time off. I needed a break, but real soon, I'm going to get, I'm going to go to war again. Um, just because I need that. I've just liked to fight. It's just fun, you know, so I'm going to do that eventually.
And now I'm just plotting, I'm plotting, I'm reading, I'm consuming and I'm just preparing. And, um, so I don't have too much focus now except on that. 
Watson: And it's also probably to some degree, you know, that you have the operational executional abilities and identifying the, you know, 10 out of 10 opportunity as opposed to the two out of 10 opportunity where there's the leverage to make that happen 
Parr: as.
And I'm still doing little two out of 10 opportunities just to keep my, my skillset skill set sharp. So for example, uh, I launched like a little copywriting course. It's only like $89 and it's killing it. So make it like a grand a day. Uh, and people are like, why are you selling this $89 thing? And I'm like, I gotta stay sharp.
You know? So I I'm like doing little things like that. 
Watson: What did you have to either get reminded of or learn in order to sell that $89? 
Parr: Uh, I wanted to get back into copywriting. You could find it if you could go to, uh, try, copy that.com. Um, I basically taught myself how to become a copywriter by this, using this learning methodology called copy work, which isn't very popular, but I think it's the best.
And so I just teach people that methodology. And by the end of the two weeks, they become much better at writing and, uh, you can see the landing page. It's like just, just texts. And, uh, I wanted to see if I could do that. I was like, let's see if I can get this to be a 4% conversion rate on this landing page.
And it is what, and I get so much joy out of that. I get more joy out of that than selling a company for a lot of money. 
Watson: That's, uh, that's funny that I think that that's a edifying and relatable for a lot of, uh, other folks out there that it's about the journey and the tinkering and the exploration 
Parr: there.
Yeah. I'm like that. Like I wake up in the night just to check the Shopify conversion rate, just to see what it is. 
Watson: One of the thing that paralyzes people from starting new. Projects is worrying about the tool. So like, I want to start making videos, but like what camera, or I didn't want to start a website, but like what provider?
And you've seen the tools that it takes to scale to millions of subscribers, to the hustles newsletter and things like that. Um, so, and you referenced Shopify here, which is a super robust, large platform for selling things online nowadays. How do you think about the tools that you use when you're building something and what are you optimizing for in terms of like, this really matters and like this stuff really just 
Parr: doesn't move.
So I have a disdain towards people who do that. And so like, for example, people who collect domain names, they piss me off people who say like, I can't do this without this domain name. So the copy of that thing that I showed you, I made 20 grand at first. Um, and I didn't tweet it. I just went to Facebook groups and I posted it.
People didn't know who I was and it was on a Gumroad page with no custom URL and it made $20,000. Um, and so I do that on purpose because I'm like, I don't need fancy tools. I don't need any of that. It's completely irrelevant. Now if I'm starting a company and I know it's going to be big, and I know that because I have a little bit of experience and things like that, then yeah.
Selecting the right tools early on is important, but for the vast majority, and it's even not that important because you can always switch out of it. Most of the times you can switch out of it. But for the vast majority of people, basically everyone listening to this, I would even say that. It doesn't matter what you use.
It doesn't matter if you use convert kit MailChimp. It does. It matters not one single bit. It doesn't matter if you record with your iPhone or with this fancy camera that I'm using. It doesn't matter at all. And in nine out of 10 cases, I would say, use your cell phone. Don't even use a camera because my goal is two things.
One, I want to reduce friction. So if I can't figure out how to upload video from this fucking camera, which I don't know how to, I'm just never gonna run. I'm like, this is too much. I don't know how to do this. I had to pay a guy to come and set this up. I don't know how any of this works, but what I do know is I know how to use my phone and I know how to say cool shit to a camera, and I've done that.
And so like, I'll get views because there's zero friction between me and creating. So I look for zero friction. The second thing is momentum. So I'm like, if I have an idea and I want to do it, I got to pursue it with. And if there's any type of things that get my way about momentum, I ain't doing it. So sometimes when you buy a domain name to get it set up on WordPress, it takes like 20 minutes.
Like, no, no, no screw that. I'm just going to use like, you know, generic name dot Squarespace dot. That's just all I'm going to use and it's going to work just fine. So I like, I I'm, I really force myself constantly to reduce friction and to create momentum. And I cannot stand when people use that they need a certain type of technology in order to, um, start.
I think that those people are losers and that's a loser attitude and you really need to get out of that attitude. 
Watson: Amen to that. Um, Sam has been awesome. I want to move towards wrapping up. Uh, before I ask my standard last questions. What were you hoping to share today that I didn't give you a chance? 
Parr: And you guys can, uh, follow me on Twitter though.
Sam Parr. Follow me on Instagram. Thus Sam Parr. I just did that thing. Copy that. So try, copy that.com. Let me know what you think I'm promoting it. Um, Um, oh, oh, duh, listen to my first million. That's my podcast. That's like my biggest thing going right now. Me and my cohost, Sean, we're, we're killing it. We're doing a really good job.
Listen to that podcast. 
Watson: You have said that that was the, one of the hardest things you've ever had to grow. Um, what would you tell Sam of two years ago about growing a podcast that you know now other than hiring Ben? 
Parr: Yeah, so, um, I don't the reason, like, I don't know why it's. So like if you asked me how to get big, it's like 2 million monthly uniques now, monthly downloads, which, um, I have to think.
Top five, most listened to podcasts this podcast. And I don't know what we did. I have no idea why it works. There's a couple of things that did work, but I don't know if they actually moved the needle. I think what would work and we're starting to do now is you buy ads on other people's pockets. And you spend a lot of money and do it with a lot of people.
And I think that's a surefire way to grow. The problem is is that if you're not good, you're not going to retain people. The thing about podcasts is it's the hardest thing to bullshit. I can bullshit a DTC company by creating really cute photos and copywriting and getting you to give me your credit card information.
You may not buy it again, but I can get you to buy it first. Um, with a tick tock video, I can make a 32nd video. That's pretty good with a video on YouTube. I can make a five minute video. It's pretty good. Three podcasts a week that are each hour long. It can't really hide bad. You know what I mean? So you gotta be on top of your shit and you gotta be really talented and really skilled folding and good.
And I think that we are Shawn, my partner is very, very, very talented. And so that's why it's hard to grow because you can't fake it, which you can fake a lot of other things. 
Watson: Do you think that that's also tied to the copywriting thing where you're being a good copywriter in written form translates into your skills, a podcast or?
Parr: Yeah. 100%. That's I, that's why I think it's the best thing people can learn. It's basically what you're doing. All you're trying to learn is how to influence people and we're all trying to influence someone. So yeah, it's really important. 
Watson: Well, we're going to link all those digital coordinates that you referenced in the show notes for this episode, people can check it out.
Uh, but before I let you go, Sam, I'd like to give you the Mike one final time to issue an actionable personal challenge to the audience. 
Parr: What time of day does this episode air typically? 
Watson: Uh, Monday mornings. 
Parr: Great. By Monday night, you have to have this whole thing completely done. If you're listening to. By Tuesday, you got to get it done, completely done by the end of the night, make a list of 50 people, no less than 50 of 50 people who you wish you could get in a room with.
Whether you want to learn from you want to do business with you just want to become friends with, do you want a date? It doesn't matter. Make a list of 50 of them and do it in a spreadsheet. And Oncom one put the names column to put the. Column and find their emails and find their Twitter handle. It's really easy.
You can use like email Fox, email hunter just do like email finder, plugin, so easy. Find their email. And then in the second, uh, sorry, the third column put messaged and then do that like eight times. And what you're going to do is you're going to cold email, these people and DM, and I'm on Twitter and you're going to put an X if they didn't reply.
And then if you did get a reply, you put reply. And then like put notes about what happened and you're gonna do that with 50 people, and you're not going to stop following up with them until they basically tell you to F off or just know. And so if they don't reply until number eight, doesn't matter, keep going, you keep going.
And you use that, put those Xs in that mark and you, and you start doing that today and you follow up with them every two days until they tell you to F off. And, uh, that's what, that's, what you should do. It will change your life. 
Watson: And when you've done that. So as to not waste the opportunity with these people that you really want to get with, like, what's your, I guess it's wildly different.
If it's like someone you want a date of birth, somebody want to be in business with, but what's your strategy going in? So that they're just not like this is a, a 
Parr: weirdo. If I don't have like a determined, um, outcome, like I want this person to give me money. I want inevitably the answer for me in most, or in most cases, the answer.
Inevitably in some period in our career, I want to, I want this person to give me money. I want to give them money. Uh, I want to do business with them. I want to learn from them. So most of the time when I do this, I'm just trying to get on someone's radar. And you, if you're a young person below 30, you have a huge amount.
Here because people who are successful love and admire young people who are just trying to hustle and get shit done. And so if you're writing an email flattering, an older person who's successful and new, let them know, by the way, this is what I'm working on. Things are going well, you know, I don't even need a reply from you, but I'm going to send you an email every couple of weeks.
Just an update on what I'm working on and maybe you'll dig it and just getting a reply, like, yeah. All right. And then I've done that with dozens of people. And by month, six month eight, they go, Hey, I'm going in town. Yeah, I do. And now I'm great friends with a lot of these people and, and, and then it's like, uh, Hey, um, so I did this with the guy who started Gilt business, insider and Mongo DB.
And I, I emailed them all the time. I said, Kevin, what's going on, man? I got a, I got a question I need to ask you. Um, or I'll say, Hey, what's your opinion on X, Y, and Z. Now we're friends. And now we're associates. I've done this with the founder of Pandora. I emailed them like 50 times before we replied. Now we go out to dinner with our families.
So like, like it works really well. 
Watson: Right on well, inside baseball, this is the year in which I've been the most systematic about the people that I wanted to talk to on the podcast. You were on that list and we were continuing to knock them off through the remainder of the year. So we'll see that played out for folks that maybe this is their first time listening because of Sam.
Uh, you can hit subscribe here as well to check that out. But, uh, I think that's a fantastic challenge. Everyone should act upon 
Parr: sick. Hopefully. Hopefully it works. 
Watson: Thanks for coming on the podcast, man. I appreciate. 
Parr: No problem. I hope it's a whole. We 
Watson: just went deep with Sam Parr. You're out there has a fantastic day.
Hey, thanks for watching to the end of my interview with Sam Parr. If you're interested in an interview with another top digital marketer, check out our recent past interview with Tucker max, all about the concept of Dumor optimism. Tucker was an initial investor in Sam's company, the hustle, and has had his own string of entrepreneurial and writing success.
Check it out.

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