011: Big Ideas, Bootstrapping, and Balance with Sam Parr

I find it quite addicting to come up with an idea and turn it into reality. And then the other half is just like proving every like high school bully and girlfriend who dumped me wrong.

And it's a very honest answer. Attention is power and creators harness it better than anyone else, but they're not using that attention to create the biggest impact possible and are vastly undermonetized. Hi, I'm Rachel Rogers. My co-host Nathan Barry and I believe you can be a billion-dollar creator. Sound impossible? Over the last 10 years, we followed each other on our own quest to build billion-dollar companies. We've studied creators and seen how entrepreneurs build traditional audiences and use them as a launching pad for a massive business. And it got us thinking, if it can happen for them, it can happen for us. And if it can happen for us, then why not you? Billion Dollar Creator is a show teaching creators how to capture attention and turn it into real wealth. We will deep dive into brands, celebrities, and entrepreneurs who have done it before and show you how you can apply it to your business as an everyday creator. Join us weekly as we learn from both the wild successes and the missed opportunities, the grand gestures and the integral mistakes, and through that, help you become an expert at building your audience on your journey as a billion-dollar creator.

We were all just having a chat and, uh, You know, talking through things and we're like, oh, we're supposed to go up. We were having a good time. But I think a lot of things with, you know, the podcast, the idea for it is like, if we just have a good time and then we bring people on that we're going to have a fun conversation with, then that's the whole thing for the show. And so you guys get to participate in that. So thank you for coming out.

That was our trick to get ourselves to do it consistently because we're not good at being consistent, but we are now.

Nathan wanted an excuse to fly private, which he's doing. On his behalf. I can't believe you're doing that.

You did have to bring that up. But you know, if you're honest—

I was joking with your coworker. Look, here's the thing. You are so far on the spectrum of a wonderful person that you're able to do a lot of douchey stuff and still be a wonderful person. You know what I mean? Like, you've built up enough goodwill that you could get away with a lot.

Yeah, I could see that. So as my new— wait a minute, wait a minute.

Is flying private exclusively douchey?

No, but if you brag about it, which if he ever wants to do, he's got it built up, he's allowed to do it.

Okay, so is this official permission that I can brag about?

Do you think you've built up so much goodwill?

Okay.

Well, he doesn't just fly private. If we're going to talk about it, he actually owns a plane.

So that I fly myself.

Yes, that he flies himself. So there you go.

I was not expecting that this is how we were going to start the podcast, but you know, it is talking about billion-dollar groups. If anyone wants to know, we did charter a plane to come down here, and then I'm actually having my flight instructor bring my plane, which is a much smaller plane. To LA and I get to fly that back to Boise.

See, it doesn't sound lame when you say it.

What part of it would sound lame normally? All right. So with this show, we're talking about the idea of a billion-dollar creator is taking an audience which is insanely valuable and many people don't monetize it in the best way or they monetize it in a fantastic way. But then I don't realize like how much more valuable that is. And so, Sam, one of the reasons that I wanted to have you on in addition to your rugged good looks and your ability to start a conversation with somehow roasting and complimenting me simultaneously, is I think with The Hustle, you built an incredible business in a very traditional way. And then in selling it to HubSpot, they're actually playing that billion-dollar creator playbook where they realize this audience is insanely valuable to them because of the lifetime value and like the enterprise value of HubSpot as a business. So each subscriber to The Hustle is worth significantly more to them than it was to you as a media business, I believe. I'm curious what you think about that.

Yeah, so I'll give you guys a little bit of background. I started this thing called The Hustle. We started it— I originally started it as a conference. It was called HustleCon. It was an event. It was like a TED Talk, but we would have like the founders of Casper and Away Travel or whatever startups were really big and cool in 2014 to 2016. And in order to make that popular, I created an email list. And in 2016, one of my best friends, Neville, wherever he is, he was always bragging about how awesome newsletters were. And I was doing the math and I was like, "Look, if we get a million people to subscribe to this and we send daily news, I think we can make like, I don't know, $20 or $30 million a year." I was just doing the math. And so, we launched The Hustle. I sold it in year 4. My goal was to get to $100 million in revenue. I sold it before we got there because I was like, I didn't have a lot of money when I started the company and I had a chance to have financial security. So I was like, I should just take it. And we sold for many tens of millions of dollars. I was given a bunch of HubSpot stock and the HubSpot stock like tripled in price in like 6 months, which very meaningfully changed the deal. But then it like went way back down. So the target that we sold for was a bit moving, but it was mid-eight figures. And when we started, I thought advertising was a cool business. It's not. It sucks. It's a shit business. It can do well. One of my best friends now is this guy named Austin Reef who founded this company called Morning Brew, and he only sold a portion of his company recently. He didn't sell the whole thing, so he's still running it. They're doing like $80 million in revenue. So the economics were such that we could have got there. I think the hustle in year 1, we got 150,000 subscribers and we were emailing 6 days a week. Year 2, I think we were at 500,000. Year 3 was 1 million. Before when I sold it was like 1.8 or something. Now it has, I think the last I heard it was 3.7 million subscribers and the open rate is still like 50 or when I ran it, it was 50%, but I think Apple changed a bunch of stuff.

Yeah. It's confusing now.

Now it's like 60%. So I don't, I don't know how that compares to what, when I ran it, what it was. And so I guess if you do the math, that's what, 1 point, maybe close to 2 million people a day opening it. Maybe at 3.5 million subscribers, I forgot, what could we do in revenue on that? Maybe 50 or 40, maybe 40 million.

With that, because it's not just about the number of subscribers, it's how often you're emailing. So those total impressions, there's a lot of them.

Yeah. So there's a lot. I think when I sold it, we were sending, I think it was 70 or 80 million emails a month. So anyway, my whole vision for the business was let's build up this huge audience and make them love us, and then we'll create stuff and sell to them. The first iteration of that was this thing called Trends, Trends.co. And it's kind of funny, I was doing all this research on what stuff to make to sell to them. In my research, some of my friends thought it was pretty good and they go, "Just sell that." And I was really stupid because I did that, but I charged $300 a year when I should have charged probably $30,000 a year and sold it to companies because the same amount of work that we were putting in for this $300 a year thing is like the same amount of work that a lot of people are doing for $20,000 a year. And so, I really screwed that up. That was a dumb mistake. And that worked really well. Within 10 months, maybe, I think we were doing $500,000 a month in subscription revenue. So we were on like a $6 million run rate. And I think it was only 10 months old when we sold. You can go back and find all this, but it, the plan would've worked. And now HubSpot bought us and they were the first company to really go all in on this idea of they're, they, Dharmesh and Nathan Barry are good buddies. And they went on this idea of let's own these brands because basically HubSpot has many millions of people coming to their blog every month and they were They were like, we're probably, I don't know if this is true, but they were like, we own everyone searching for anything related to what you would buy, what you would look for before you bought HubSpot. And they were like, we just gotta own this damn thing. And that's why they bought us. And they were the first to do it. And I know a little bit about the numbers. I don't know too much. I haven't worked there in a couple years. Their plan worked. It worked really well. And what they bought us for, in my opinion, was a steal. And like, if you look at the revenue that they've made from it and how much they're, I think they're valued anywhere from $8 to 20 times revenue, they got a hell of a deal. And I think now, I think, I don't know for a fact, I'm pretty sure they only have like 4 people running The Hustle.

Yeah. One question I have for you is it sounds like you were thinking like a billion-dollar creator when you created Hustle. Is that, was that your first business, The Hustle?

So I owned hot dog stands in Nashville. So I had that and then I had a roommate matching app before that and it was like Tinder but for roommates. And that's really stupid. I should have done Tinder for Tinder because when we launched it, Tinder wasn't even popular. We were— it was like swiping for roommates. And I think I made like $100 grand when I sold it. And then I started HustleCon and then I did The Hustle.

Okay, so you were thinking like, let me build a really big business from jump.

What I wanted to do was I wanted to have financial security by the age of 30 because I didn't have a lot of money and I wanted to have— I had a scarcity mindset and I was always afraid of being homeless.

Yes.

So what was financial security to you at 20 million by the age of 30? That was my number. I met a rich person and they told me that they spent $60,000 a month. In my head I was like, 4% would be like 20 or $25 million.

You did your FIRE math.

Yeah. And, and so I just made up that number when I was 21 and that's what I wanted to do.

Yeah. Awesome. Okay. Uh, why do you think so many people start out building really small businesses instead of going for the big idea?

Like, well, it's just intimidating. It's intimidating. And you typically, if you're like, I lived in San Francisco and it was awesome because I got to meet all these people that were like working on Bitcoin in 2013, even though it felt silly, it felt like some grand idea. Or I had people that were helping make Airbnb huge. But if you live in St. Louis where I'm from, or maybe Boise a handful of years ago, you don't know that many ballers who are like reaching big. And I think that's the reason why, even though oftentimes it takes similar amounts of work to be really huge. Typically, I do think you often have to raise money if you want to do it in a fast way. And I think there's a lot of stress that comes with that. But I still think you could build a pretty big bootstrapped business fairly quickly. It helped to have a role model who you're friends with and you're like, oh wow, you're not that much better than me, but you're so much more successful than I am. Now I have faith and confidence in myself. And that takes like being around other people.

Yeah, I agree. And that's one of the reasons why we started this podcast is because we want people to dream bigger. Right? And think about this. I agree with you, and I love that you said that, that it takes the same amount of effort. I know for a fact that I worked way harder when my business was making $250,000 a year than I do now. And it's an 8-figure business.

You know, we did this survey. I have this new thing called Hampton, and it's like a peer group for CEOs. And we asked them what their net worth was, and it ranged from like, your business has to do $2 million a year in revenue in order to get it. So whatever that you'd value that at, all the way up to like, there's a bunch of people in the $800 million range. And the, the median, the medium hours per week was the same for all categories of net worth.

Wow.

What was it?

In fact, we had a category of $100 to $100+. We're going to publish this in the next handful of days. The $100 million+ people who had the net worth, they on average were working like 40 hours. And then like the $1 to $10 million people were actually working a bit higher in the 55-hour range.

That sounds right.

But it was like the— it was very close to the amount of time worked.

Yes.

What do you see in that of— I mean, you can't trend the data over time. Later on, you will be able to as you do the survey, you know, year after year, I imagine. But do you think that's the trend where when someone's building that company from, say, $1 to $10 million a year in revenue, they're having to work a whole ton? And then as they get to scale, they're able to back off? Like correlation?

Yeah, a little bit. But also, in order to get big, you need to hire hire really high-quality people and delegate. And if you don't do that, you work harder and you don't get big. And so the confidence issue that I had that I don't have as much anymore was I'm embarrassed to hire someone who's older and better than me. And so a lot of times I would hire someone who's like younger and worse than me because I'm like, I'm like, I'm like, why would this person listen to me? You know what I mean? Like, what the hell do I know?

Because you're paying them. I mean, and they agreed to take the job. No, I—

You sound very emotionally stable. Congratulations. That's not an attribute I rank high in. If we were a video game, emotional stability would be like a 4 out of 10.

I mean, I relate to that, especially starting in business really young. I remember going to like my first Chamber of Commerce events when I was 18, doing web design, like running a web design freelance business. And then all the way along, I was just always the youngest person in the room. And you talk to people and you're like, wait, you want a job here? But then like, I would tell you like, okay, you could tell me what to do, that's fine. You know, like, it's a real thing to, to have to get over.

Yeah, that's interesting. Forever.

I did not have this problem, not at all. I don't know why, but I did not.

You sound like you have very healthy parents. I mean, I don't know what to say. Like, well, you've done well.

I don't know how healthy my parents were, but I went to law school. Maybe that has something to do with it. And I was building a law practice first, and then I got overwhelmed with work, so I hired an admin to help me, and then I hired another lawyer. And so I— and also, it might have had to do with my first job out of, like, being done with college and law school was clerking for a judge, and they just give you a ton of responsibility. You just graduated, and I'm like, I'm telling these lawyers who have been practicing for 30 years what to do because I work for the judge. And I was like, why are they letting me do this? So maybe that's actually where I learned how to delegate and manage people even if they're working.

I would be in charge.

Yeah.

I guess so. We used to do these events. We had this thing called HustleCon. We did it for 4 or 5 years. And I remember I used to, I had a lie that I would tell people. I would say, you're speaking at 3, but you've got to come at noon for the mic check. Just like this event, there is no mic check. Mic checks at conferences, they work. Okay. But we had a green room and it was just my opportunity to hang out with these amazing people. And so I would get to hang out with like the founders of Grammarly or back then when we thought WeWork was awesome, the founders of WeWork. And I said like Casper and Away Travel and like all these like multi-billion dollar companies, I got to hang out with them. And what I noticed was that they would be maybe 10 or 100 times more successful than I am. They would freak out still. For example, Sam Yagan, he's the guy who started OkCupid. He was the CEO of, I think, Match and now the company that owns Match. I forget. It's a public— I, It starts with an I, IAC. Yeah, IAC. And he was pacing back and forth in the green room and I was like, hey man, do you need something? Can I get you some water? And he was like, snapped at me and he was like, just leave me alone. And I was like, hey, look, Sam, I can help you. You seem really nervous. And he was like, I'm sorry, I'm just nervous to speak in front of these people. And I was like, but why? You have like 20,000 or 10,000 or something employees. And it gave me so much confidence that the people that I admire that were like ballers, they were freaking out all the time. And I remember like I hung out with this, I remember when I hung out with this other company and they had just raised a thing of funding and they were in the New York Times and they were like, this woman was like the it girl. She was like so cool and successful, whatever. And she was telling me that she didn't fire this one person for the past 12 months, even though this one person was imperfect for the role because she was just afraid of the conflict. And I was like, what? Really? Like, I admire you so much and yet you're— and so it was almost as if I had bad eyesight and I finally was putting on eyeglasses and could like see, like, I was like, oh, this is awesome. Like I could be like really uncertain and not brave about certain things, but as long as I do it anyway, it'll be okay. So that gave me so much confidence because there was very few people that I met that were like 10 times smarter than me. There were a few that does exist, but like for example, the founder of Grammarly, when I would hang out with this guy, I was like, oh, we just don't have the same amount of horsepower. There's no nothing I can do that I can keep up with you. But there was many others where I'm like, we're in the same ballpark.

Yes, that working in the government did that for me. I worked for Hillary Clinton for a time, and seeing what a hot mess the office was, like every Senate office, and like if you go to any of the congressional buildings and see how the setup is and what a mess it is, it will make you be like, oh, okay, I see first of all why this is a mess. And then also it makes you feel like you can kind of do anything because it's You know, important people doing important stuff and there's mess everywhere. So, you know, thinking that you have to do it without the mess is all wrong.

It's awesome to see your heroes screw up and like be insecure and stuff.

Yes. And be regular. Like they're just normal people.

Yeah.

With their own stuff. Yes. I met a podcaster recently that has an enormous following, like millions and millions, tens of millions. And this person has a lot of like social anxiety and won't do public speaking and won't go on other people's podcasts. Even though they have this super successful podcast. So it's interesting, you know, we all have our quirks, right? We all have things that are challenges for us.

Do you try to design around those quirks and let— or do you try to go straight through them and say, I'm going to overcome these?

Yeah. Oh, so I'm definitely of the mindset that I'm going to double down on what I'm great at and do absolutely none of what I'm bad at as much as humanly possible. So I hire for the things that I'm terrible at. Like, I'm not good at organization or building process and systems. Like, I know this is— I know I want a system, but I don't know how to build that system or what the steps are. So I have a lot of operations people on my team because I suck at that. You know, I literally have worked myself out of every part of my job that is not what I'm great at.

I heard that you don't log into Slack anymore, like the company Slack. I think I overheard this the other day. And so you're just not in the day-to-day anymore at all?

Yeah, I— well, I took it off my phone and here's the hilarious thing. So I took it off my phone because I was trying to scale. Stop. I have the president of my company who runs the day-to-day, and— but I kept meddling. And I was like, I'm not going to be involved. Like, it's fine. I'm just going to let you do it. But then I would see stuff and I'd be like, ah, don't do that. Do it this way or whatever. And I kept inserting myself. And then when I looked back, I'm like, they didn't need that note on that graphic. Like, just shut up, you know? But I can't trust myself to not intervene. And so in order to like let her do it, I had to take myself off of Slack. So I just took it off of my phone. And then I tried to log in on my laptop today just to see what was going on. And I literally couldn't get it to load because I haven't been in there for so many days and there's so many messages every day that like it was—

your assistant changed your password.

Yes, it was struggling to load. So I was like, this is my sign to just keep minding my business, you know? But this is the thing that I want y'all to understand. Like at an 8-figure business level, I don't need to be there every day for the business to run, for people to have success, for clients to get results. I don't need to be involved. I'm not even— not only have I outsourced the task, but also the decision-making, you know, like even my husband, who's the CFO, tried to come to me today with like an important decision that needed to be made. And I was like, that sounds like a financial decision. And I'm like, that sounds like it's in your department. I'm going to go shopping. Talk to you later. Let me know what you do.

It's a different kind of financial decision.

But one of the things I will say that has been great for me, and I think this is where you're at. You're post-revenue, right? Well, at least that's how I think of you.

Like, what's that word?

Post-revenue or post-worrying about money?

Because it's economic.

Yeah, post-economic. Yes, that's, that's the phrase that I was looking for. But I think part of my freedom comes from like my lifestyle is of a size that I don't actually have to worry about the revenue of the business to just like take care of myself. And that actually allows me to take some of the pressure off. And not worry so much about growth. Like there was a couple of years we went from $2 to $5 million, $5 million to $10 in like a 2-year period, which was very stressful. We had to scale the team very fast, all those things. And I think I'm just in this phase where I'm like, I'm not worried about it. We don't have to grow. We don't have to double revenue every year because it was all ego, you know, like that's what part of it is, impact. Part of it is wanting to serve as many people as possible. But if I have to go so fast, it was somewhat ego-driven. And so therapy helps. And like being ambitious, but also being able to wait for the results and not feeling like— it's actually much more abundant to say, I'm going to get there and it doesn't have to happen tomorrow. Like if you're so desperate that it has to happen tomorrow or the next week, that's actually not thinking abundantly. That's like scarcity, right? Like there's not enough time, right? It's going to go— the opportunity is going to go away. There will always be another opportunity. So anyway, therapy is the point.

Sam, I'm curious for your side. Are you the person who sees like what you're great at and or any of those?

Yeah, I only got good at that recently.

Okay.

And like the last 2 years, I tend to— the things that I suck at, I actually try my hardest to learn how it's done and what excellence looks like, even though I can't exactly execute it. For example, like the year we did like $12 million in revenue, I didn't know the difference between cash flow and revenue. Like, which is like a huge deal. That's like really bad not to know.

I just saw Jay here in the front row put his head down for a second.

Yeah, that's like a massive issue. Like, I didn't know the difference between the two and I didn't know the difference between a lot of different things were. And so actually Kat, my friend Kat, she told me to take this thing called the 4-Day MBA. And I, uh, has anyone with Keith Cunningham? Yeah, it's awesome. It's like an accounting class. And so like I try to learn, like even though I can't actually do the accounting on my own, but I actually try to learn how to do it. And I'm something I'm very good at. I'm really bad at a lot of stuff. I know how to hire really well and I know how to get them going and doing the right shit. And so I hire wonderful people and then I just like, I know enough hopefully about many things that I can kind of know that I'm not being like stolen from or something. You know what I mean? Like, it's really important for me to understand that.

Yeah, I think that I have been in the model of whatever I don't know or whatever I'm not good at, like that's a skill that I'm going to hone and improve. And because early in my career I was trying to do like be a designer, a developer.

You were a great designer. Do you guys know how I know Nathan Barry? He had this book called Authority in 2013. Yeah, that's— Was it '13? And I went and saw him speak at the Gumroad office in San Francisco in 2012 or '13. And that is how I knew you because you were designing icons, I think, right?

Yeah. iOS apps and all of that.

I thought you were great at design.

Well, thank you. This makes up for the comments earlier. So what I always had that approach of trying to overcome all of the things that I wasn't good at. And now I think I'm starting to make that shift where I'm saying, I don't know if it's like I'm stopping growing in those areas and I'm like, I'm going to hire other people or the growth that I actually need to do is to say this has to go beyond much more beyond my skills. And so, you know, the growth to say, you do that, I'm not going to be involved.

Yeah. And just stay in your lane. I also wonder if you have to— I've had people say that to me before, like, I need to know what the team member needs to do every day in order to manage them. And I'm like, no, you don't. Why do you need to know? I don't know crap about design. I can't even log into Photoshop. I don't know.

Well, I typically, I like to understand a little bit because I want to know, like, can I push them harder? Like what's reasonable and what's like on the far edge of reasonable? Because like when you run a company, there's times when it's like, all right, I'm gonna push 'em super hard to, to get to, they're gonna be borderline quitting. And then like next month we're, it's okay to chill. Like I know that like we're executing a bit slowly, you don't, you need, I have to feel that pulse, but I always try to study that shit so I know like, all right, this is unreasonable, let's go there.

Okay. So two things that I do. One is just KPIs, right? Like you just track every team member needs to have, KPIs that they're tracking for. And so that's one thing. But the other thing is hire two. So like, you can think like you might hire one person and you think they're amazing. This happened to me in my law firm. I hired my first attorney. I thought she was the bee's knees. I just liked her, you know? And then she also was executing. She was very smart, but she also like pushed back on everything and disagreed with me on everything, was very slow to get work done a lot of times. Then I hired my second attorney. And I was like, the first one sucks. You know what I mean? But I didn't know that until I hired the second one. And the second one is crushing it and like executing so much more, so much easier to manage. And I'm like, oh, actually this employee thing is not that hard if you hire the right, the right person. So that was advice that I got from an older lawyer who was running like this multimillion dollar practice. He's like, you need to hire two of everything, right? And when you hire the second one, that's how you know whether the first one is good.

This is something that I had not heard before. I was talking to the guys who run sales for Ramp, the credit card company.

Yeah, they kill it.

They're very, very good.

And so I was—

The guy who started that company, that's going to be a big-ass company. That guy's amazing.

That's awesome. So it was like 3 different sales leaders in the company. I think it was the chief of staff and 2 sales leaders that I was talking to, and I was asking them how they structure their team, how they commission, all of those things and the different roles they have in their sales pipeline. They were also trying to convince ConvertKit to switch to Ramp. And so, you know, it was I was trying to extract as much information from them as I could. But in that, I said something about our migrations and implementations team for ConvertKit, how we have one person run that, she's amazing. And they were like, "Hold on, that sentence doesn't work." And I was like, "What do you mean? We have one person that runs it and she's amazing." And I truly believe she's amazing at her job. And they're like, "You can't know that she's amazing if you only have one person doing it." They're like, "Have a second person, compare them against each other, they each have their KPIs, and then you'll know." if it's actually amazing. And so they were saying that in a, like, a revenue organization, so sales, implementations, uh, account management, they're like, you always have to hire 2 people. And I hadn't heard that before, and now I've heard it twice in 2 weeks.

So now that's your new focus.

There you go. Or I'll actually— I'm just going to talk to my chief revenue officer.

But that's the other thing too, is if you hire 2, they push each other, right? They motivate each other, and they also have like a work partner that they can connect with, bounce ideas off of. And also, I think healthy competition is good, you know, so you have some competition of like, okay, I'm going to push because this person's really good and now I want to get on their level.

Yeah, I like it. I'm also interested in this idea that you have of like finding where the edge is for the team, because I think a lot of people— not that you want to push people to burnout, but you also want to help sometimes.

Okay, sometimes you do, right? Like, look, like, great. You know, they always say it's like, people are like, you know, it's a marathon, not a sprint. You ever try to run at world record marathon pace? It'll feel like a sprint to a lot of people who aren't good. You know what I mean?

What I've heard is it's a marathon, not a sprint, but professionals run marathons at 4.5-minute miles.

Yeah, it's really fast. So like sometimes you do, but then there's also chill time, you know, company, the energy will ebb and flow and you have to be good enough to understand that.

But I think there is a balance of trying for yourself and the team that you've built and helping each person individually know what they're capable of and building that, that resilience. And fitness is an interesting example for it because if we were all to go out and say like, okay, we're going to run a 7-minute mile, I'd be like, oh God, I don't know. You know, but if someone said, hey, a year from now, like we're going to build up to this point, whatever this fitness goal is, we're going to train towards it and build that resilience. And absolutely you get to a point where it's like, okay, that, that is easy because we worked up to it. And so having people on the team who, want, who know what they're capable of now, and they as individuals want that bar to be higher, and they're saying, hey, I'm not going to, you know, get there tomorrow and absolutely kill myself in the process, but I'm going to see where the goal is and methodically work towards that. Like, that's a really good team.

I think that's very true, and I find that most people, especially like A-players, when they want to get better at their job and they want to be able to produce more and like have wins, so I think giving them that feedback and pushing them to do more, you know, is good and they want that. I think people will leave if they get bored in their job.

Does everyone here work remote? Does anyone here go to— raise your hand if you work at an office. That's wild, right?

We have 3 people. 3 people.

3 people. I am nervous that people— because I like, I feel like I slack off so much, like working remotely. I'm very curious about how— this is the first fully remote company I've had. I'm very curious as to how, like, you figure out the limit and shit from like being remotely. I feel like a bum working from home. I'm going to go back to the office.

Yeah, I've had a remote team for a long time and I can tell when someone's slacking off because you just—

I can tell.

Yeah, you can tell. There's like a— there's a sense and a vibe and you're like not seeing the output of their work.

It's just lame is what it is working remote. I hate it. It's just super lame. I feel like such a bum. I thought it was amazing, and in many regards, there's so many awesome stuff about it, but I just feel like— I feel disgusting. I'll wear like gym shorts half the time, and I'm like, I have to put something nice on. I have to comb my hair. I've got to like do something to feel special. And like, look, I'm a simple man. And my wife, like, we live in New York half the year. She'll like— she goes to the office and she's like, I love getting dressed up nice. I love walking around the street. I love looking at people and being seen and all this stuff. And so this is the first time in this whole post-COVID world where I'm like, yeah, I need an office. And I'm wondering how that's going to impact our productivity. WeWork.

I like WeWork.

I don't know if that's going to be a thing, but I like WeWork. But yeah, like I loved remote at first. Now I'm like, I particularly for men, like I'll go 2 weeks without seeing another person in real life. You know what I mean? I'm lucky that one of my best friends, Neville, lives 2 doors up, but I won't see another human being for like 2 weeks because I'll just be in my room the whole time. Sorry, I don't know how we got on this.

I'm going to leave it to you to decide where we go from here.

Well, I'm a big fan of remote work, but I do run into those things where I will say like, oh, other than taking the kids to school, I have not left the house in 3 days or something. But I think that, I don't know, there's tradeoffs in that. I like honestly the the deep work at home for a long period of time and then like batching, you know, things like this travel. Yeah.

And I agree, like when you have school-age kids, you leave the house every day, you know, because you got to get them to school.

Yeah. There's been 2 weeks where I just haven't left the house and I literally have 600 steps. You're right.

That you launched the health app and it just says like, no, man.

No, you just—

maybe just go for a walk in the morning, you know, to start your day, just to get outside.

Neville, you need to help this man. I know you're trying, but, uh, try harder.

You want to talk about the— one of the prompts was which brands that are doing the creator, the billion-dollar creator thing that you like, because I had asked you, are there any good B2B ones? Did you have any answers?

Well, I— not to put it back on you, but I think you're doing it really, really well with Hampton, and we'll talk about other creators.

I need you when you ask me for an example.

Okay, so this is just a It's a wonderful bromance that we have going.

And I'm stuck up here with these two.

I'm sorry, Rachel. Like, we'll get a better guest in LA.

I apologize.

So with Hampton, I think is an interesting one and we'll brainstorm some other, other creators in a second. But what you've done of taking the audience that you have from The Hustle and then from My First Million, and obviously it's monetized through ads and these other things, but then you've said, okay, this attention that I have, I'm going to bring it together into a community of entrepreneurs. And you're basically building YPO or Vistage for the current generation of entrepreneurs. Is that the right way to put it?

Yeah. So, I'll give you guys background. So, my new company is called Hampton. It's about a year old. And I screwed up trends. It was this research thing. It was $300 a year. And the day before I launched it or we launched it, I created a Facebook group. And people love that Facebook group. But $300 stinks because I couldn't make enough profit to provide a really high-quality service. The P&L didn't work out. P&L, you see, keep coming in, getting those accounting terms in there.

Yeah, that accounting class is paying off.

So I studied this company called YPO, and has anyone here heard of Vistage? So it's not very popular. Some people have, but it's not very popular, but it's a company where it's mostly middle America, but it's basically like someone who owns like an $8 million a year plumbing or HVAC company or something like that. You may not have a lot of peers who are doing that. So you meet once a month with other people in the services industry or whatever industry you're in. And it's like business group therapy. You talk about your challenges. And I saw that they were acquired for about $2 billion, I think, 2 years ago. And I was already ruminating this idea of I wanted to do trends but the right way. And I called the banker who— Gridiron Capital, I think, bought it. And I found the phone number of the banker. And I go, "Hey, man, I'm going to sound really blunt and rude here, but I just want to let you know I mean it with nothing but respect." But I'm gonna build a company that is gonna compete with you, and I think it's gonna be really successful. And I think it'd be wise of you if, if we became friends now. And I know that sounds really douchey, but I just think that that's what will happen. And would you be willing to talk to me? And he did.

That's awesome.

I love that. Yeah. And we became friends and he kind of told me how the business works a little bit. I told him my plans and he started listening to the podcast. He's like, oh, okay. I, I think you might be able to do it. Could we just buy you before you launch? And I was like, no, but I told you we were gonna become friends. And so he explained to me how the business worked. And so with The Hustle, the, my biggest weakness was that we had all of these customers, but we made such little revenue off of what I felt was the impact that we had. And basically like the, in my mind, media is like an equation. It's the quantity, the number of people that you reach multiplied by the amount of influence you have over them multiplied by the, the spending dollars. So for example, let's say you're BuzzFeed and you reach just like most all of America and it's just an article that they're reading and it's news. So like you're not exactly gonna influence them that much, but you are reaching a lot of people and they're not gonna buy that much stuff. Like versus you have a newsletter or a podcast or something that talks to 1,000 people who make decisions for Boeing or some other plane company on which product to buy for manufacturing the plane. You only need to influence like 30 or 50 of them and they'll make decisions worth tens or hundreds of millions of And so you have to find that equation. And I was doing the equation in my head of how many people I impact, what I could influence people to do. And I was like, I need to create something so valuable that I can charge someone more than $300 a year. And so I loved the idea of community and peer groups. When I started the hustle, I told— I won't say his name, but I'll tell you guys privately when we're not on the record, but there was this CEO of this media company that you guys all know who they are. And I pitched him the company I was starting because I really admired this guy. He was my hero. I really looked up to him and he took the time to talk to me. I was so thankful. And he goes, "You know, look, this is never going to make more than $2 million a year, probably only $1 million a year." And it hurt my feelings so much. I was like, "Oh my God, dude, you're my hero and you just insulted me. I'm worth nothing." And so anyway, I just made all of these mistakes with media that I wanted to create something really, really good and with community. And that's when we launched Hampton. My podcast, My First Million, we have between 2 and 3 million downloads a month now. When we launched Hampton, we got roughly 5,000 applicants in the first 30 days maybe. Now, that's cool and all. Not all those guys are going to convert. Not all of them are even qualified to join. But it was a lot of people that went through this really long application. So hypothetically, that's what, $50 million of pipeline? That's not realistic, but you get the idea. Quite good. And so that's what I was thinking about. And so my opinion is it's not a matter of if, it's just a matter of when, when we're going to get 10,000 people spending $10,000 a year, or maybe it's going to be like 7,000 and 15,000, 7,000 people, $15,000. I'm not sure how that equation is going to work, but with this business, it's, I have 100% confidence that it will get there. It's just a matter of is it going to happen in year 6 or year 15?

One thing I wanted to point out, you, so you said you called this guy your competitor for this new business that you're starting. We're not exactly competitors.

But sort of. Hampton is for tech-enabled company, which means like you could be a DDC company. It's not quite a tech company, but that's who we are. That's who our customer was. This is just more blue-collar companies.

Well, the reason why I wanted to mention it is I did something. I did the same thing. I don't think it was douchey, but—

Well, you could come off like an idiot. And I was like, what I'm going to say is going to make me sound stupid. I promise you, I only mean it with the utmost respect. I'm trying to be straightforward.

Yeah.

Well, I didn't necessarily say I'm going to be your competitor and you're going to have trouble. But, but what I did was when I started my law practice, I wanted to start a virtual law office, which was brand new back then. It was like not a thing. And there were a few lawyers who were doing it. And so I just called them. I just cold called them and said, hey, can you tell me how you're doing this? And like, is it working for you? And I basically was just doing market research and they were all willing to talk to me. Some of them spent like an hour on the phone with me giving me the whole rundown.

Yeah, particularly if you're younger than them and they're like, you're like you're a serious person, they'll like, they'll be like, oh, that's so cool that you care enough to like do this.

Yes.

They'll spill the beans.

They really will. So anyway, pro tip, just call people who are already doing the thing that you want to do. And surprisingly, they will be willing to often talk to you and help you out. So it's a way to shortcut the journey.

I actually had this experience with Ben Chestnut from Mailchimp. So they were—

Is he a good guy? I can't tell.

I think I've only talked to him once.

I've only read about him.

Yeah. He seemed like a great guy.

Really?

So he—

He seems quirky and I like that. Yeah.

I think he's definitely quirky. Creators, entrepreneurs, like it's pretty much a given. Yeah.

He seems like he had the good type of weird. Yeah. But I wasn't sure if it was the good type only.

TBD. We'll see. But, uh—

I'm not saying he does. I just—

It's an open question. Yeah. So they were Inc. Magazine's like company of the year. And we were at the Inc. 5000 event that year and I saw that he was speaking. And so I emailed him and I was like, hey, I'm going to be there. I'd love to get coffee, you know? And I said a little bit about ConvertKit and he was like, oh, I know ConvertKit. Like, you guys are doing great things. Like, I don't know, like, we'll see. And I followed up. He said, like, follow up during the event and we'll see. And I sent him a note halfway through and was like, you know, hey, like, your talk was great, whatever, if you have a chance to meet up. And he just said, like, yep, I'll be in the hotel lobby. I'm checking out at this time, my flight's an hour later, and so I'll be in the lobby at this time if you want to meet for a bit. And he was fantastic. He started to break down— we were thinking about launching a free plan, and so I was like, "Hey, when you launched a free plan, what was the landscape like?" What'd he say?

Don't do that?

No, he said that that was absolutely amazing for them.

Really?

And that— no, he talked about all aspects of it where they launched at a time where there wasn't another free plan. One thing that I didn't realize is how small they were when like 10 years in, they were still a pretty small business.

How big?

Like $3, $4 million a year in revenue.

How big were they when they sold recently?

They were a billion ARR.

Goddamn.

Wow.

Wow.

So was it totally bootstrapped?

Yeah, it was 100% bootstrapped.

Amazing.

That's got to be like a top 30 biggest bootstrapped software companies.

I think so.

Top 10 maybe. Like Bloomberg would be up there or something like that.

Yeah. So I mean, they exited for, I think, $12 billion.

Goddamn.

So there were so many things. First, I learned— so there's actually 3 co-founders, not 2. And they had someone who— they were running an agency and they'd built this like MailChimp thing and they were running both. And they had a bit of a disagreement of like, should we build this software product where people just like buy credits to send emails or should we keep going with the agency? And they ended up like going their separate ways. And 2 of them went with the little software thing and 1 of them went with the agency.

Man, I feel sorry for him.

But it took a long time. Like, they launched Mailchimp in, I think, 2001. And I think when they launched their free plan in 2009, 2008, 2009, they were making single-digit, like, millions of dollars a year. And so one thing that I realized, like, okay, stick with it for a long, long time.

When did they exit? In 2020?

Like a few years ago.

2021, I think.

2021. So 20 years it took them.

Yeah, I think it was 20 or 21 years that it took them to—

but that's a nice— if you think about, like, if I think about my parents and what they did for 20 years, you know, and that's a nice exit, right, to show for your 20 years of effort.

Ben was probably— I don't— you know them more than I do. I bet they were making 9 figures a year in income, or—

yeah, they, they did very, very well—

or net cash flow.

So, but one thing that was interesting about the dynamic with Ben is he was totally willing to talk to you about anything. And then at one point the editor-in-chief for Inc Magazine comes up and he's like, hey Ben, just want to say hi. Like I worked on your article and all of that. And they talked for a minute and he was like, oh, by the way, do you know Nathan? He's trying to kill my company. And like, and he said it was this big smile on his face and like they laughed. He was like, no, but seriously, you should do a story on ConvertKit. And I was like, Okay, that's awesome.

That's pretty awesome.

So maybe that answers your question about what kind of person Ben is.

I was only joking, by the way. I have only read like 2 articles about him and he seems awesome.

Yeah. So anyway, I think the takeaway from that is whether it's competitors or whoever else— actually, another competitor story. There's a company in the creator space called Flodesk that does email marketing in a similar industry. They're also bootstrapped. And I was speaking at a conference in Chicago. Where Rebecca, the co-founder and head of product for Flowdesk, was also speaking. And I just shot her a note and was like, "Hey, do you wanna—" I can't remember even what I said. Like, I sent her a note like, "Hey, I'd love to say hi at the event." And she was like, "Yeah, let's grab breakfast beforehand." And we had a great conversation. And the way that I left it was like, "Hey, if you're ever going to sell this company, make sure you call me first." And she's like, "Yeah, I can do that." And so just that idea of hang out with your competitors, the people you want to learn from, like so many people are willing share. And they're all like, all these companies are run by great people.

Another person for as an example of this, like the billion-dollar creator thing. Have you guys ever heard of More Plates, More Dates? Raise your hand if you've heard of this person. A lot of people. That's crazy. It's all men. I was like, I got nothing. So have you ever heard of this person? No. His name's Derek. We had him on the podcast recently. He does a really good balance of being like, like bro science where he makes like a dick joke, but he's also like, He comes off quite serious, like he's well-read and well-researched. He does, he does a really good job of balancing that, like being silly and dumb and being not dumb. And he only has 2 million subscribers on YouTube. That's a lot, but that's not that much for— he came on the pod and he has, it's a More Plates, More Dates is a fitness-ish YouTube where he talks about steroids and he would like, here's Brad Pitt in this movie, here's him in this other movie. Here's what I think the supplements he was taking. And then he would get a little bit more into like, men, you're losing your hair. Here's like some ways that science has shown that you could help yourself. And then he eventually launched a supplement brand, but he also launched like a men's health clinic. And he came on our pod and on 1.9 million subscribers, I think he had, he said he was doing around $8 million a month in sales at the moment.

And what's the main driver of the revenue?

So he has 3 supplements. Yeah, he has 3 or 4. One brand is like a pre-workout/protein, which is a very common thing. The second one is like a men's clinic, which means they'll— you can get, if you wanna get hormone therapy, so testosterone, or if you wanna get other types of like therapies that you need a doctor to give you, he has a team of doctors so you can go to and you pay anywhere from $100 to probably $500 a month, I guess, depending on what, what you get. Now he's actually creating fragrances, perfumes, colognes, because a lot of young men are like, I want to be more handsome. I wanna attract more women. And I guess I don't know how that— He somehow decided that's his thing where he's going to do cologne. And so he has a fragrance company coming out. It's one of the more impressive— I think he said on the podcast, I think he's 30 years old and these businesses collectively are doing about $8 million a month and it's growing like a weed. It's one of the more impressive content turned commerce business that I've ever seen.

Well, I mean, so just to be clear, $8 million a month is just shy of $100 million a year. He would need $8.3 million a month to get to $100 million a year. That's like absolutely mind-blowing to do off of a YouTube audience of 2 million. Yeah.

Which isn't like that crazy. I mean, if you're really talented and you're good and you give it 4 or 6 years, like it's conceivable that you could be in that ballpark, you know, after, after a bit of time.

So maybe if we look at a couple other YouTubers, like Ali Abdaal is a friend of mine and he has— he's talked publicly about a bunch of his numbers. He's got 2.5, 3 million followers on YouTube, maybe even more. A lot in the like productivity, somewhat in the business space and all of that. He's talked, he shared his numbers publicly. He's making about $6 million a year, which is an amazing business, like absolutely mind-blowing business. But then when you think about like the scale.

Yeah, because it's that equation, you know, of what I was saying earlier, you really need to figure out how you can boost those numbers if your goal is to maximize that revenue. So another example is Doug DeMuro. Does anyone know who Doug DeMuro is? He's like, his His whole shtick is that he's like a geeky, nerdy, funny, lovable guy, but he reviews cars, but he does it like he'll review a super fancy $2 million car, but also a minivan. And he's very lovable and you like watching him. And so he created a business called Cars and Bids and it's sort of like eBay Motors. It's a car auction website for car enthusiasts. That's his tagline. And so there's like cars from the '80s and '90s and early 2000s that aren't particularly valuable, like $40,000 or something. Even $30 grand, all the way up to millions, that people who are car enthusiasts, they're like, "Oh, I used to see— my uncle had one when I was a kid. I totally want to get one of those." That's the type of car that you would see there. I bought my car off of it. And there was another business in the space called Bring a Trailer. Bring a Trailer recently exited for rumors around $600 million, and it was a similar style business. I think they were selling close to $700 or $800 million of cars worth a year. And so anyway, Doug started Cars and Bids, and I remember before he started it, we started talking about it on the pod and I was like, Sean, this guy, I think he's gonna launch something and it's gonna be great. And I found out because I stalked him on LinkedIn and I saw that he was hiring for this thing. So this guy's gonna launch something, it's gonna be the best. Then he launches it and we're like, it's gonna work. And then after only a year and a half or 2 years, he sold a portion of the business to TCG, the Churning Group, and He told us in the pod how much money he made, but he sold a portion of the business at around, I think, an $80 million valuation. And I think that marketplaces are one of the harder businesses to start, but once they work, they're one of the hardest businesses to destroy, hence Craigslist or eBay, which still crush. And I think that his business will be potentially a billion-dollar outcome in the next 10 years. And I think that's a really good example of someone— his audience when he launched it wasn't particularly big either. It was big, but not Well, I think there's something to being adjacent to an expensive transaction, right?

Or dealing with a high-value clientele that matters a lot. Where if you're taking a small cut of a $100,000 transaction or a $50,000 transaction, that matters a lot. There's one that I came across recently. There's this YouTuber named Mike Patey who he's out of Utah. He maybe like 15 years ago got into aviation. And so he learned to fly and he's like a machinist and like understands, I think he's an engineer. And so then he started like modifying planes and then building his own planes. And now it's a whole bunch of world records for like, they call it short takeoff and landing. Like, have you ever seen a plane like roll down, you know, like maybe 20 feet and be in the air flying, but it's like a, you know, a plane that holds multiple people. Like that's what it is. Or if you saw the Red Bull, right where Red Bull landed The plane on that little helipad, it's that kind of thing. And so he is in this world. He's got 300,000 subscribers on YouTube, very much into aviation, doing these crazy things. And he started this other company called Best Tugs, which is a weird T-U-G-S.

All right. Boats, right?

Yeah, not quite. So there's this thing with a plane where if you've ever been, you know, if you're at the airport, you see like that car that comes out to push the plane around, like the big airliner, the tug. That's called a tug. And so at the very smallest planes, you come up and you have this little tow bar that you like hook onto the front wheel and you just push the plane around like a little Cessna. And the big planes have like a car that pushes around, but you get these like small to medium-sized planes that it's too big to move around by yourself, but it's not big enough to move. And so off their YouTube audience, they made this product that is basically a little motorized thing. You just walk behind it and hook it up. And this thing costs $6,000. I know because I just bought one for my airplane. Right? And if someone's spending $500,000 or $1 million on a plane, right? A $6,000 transaction is very, very cheap. And so he here is selling this product that they can sell for a huge amount of money off of the YouTube audience. And another friend who's a pilot came over and we were flying together and he was like, "Oh, you've got one of Mike Patey's tugs." Like, "Oh, that's amazing." Right? Built this epic business off the YouTube channel because they're adjacent to like a very high dollar amount of transaction.

There's one downside to this whole like creator turned billion dollar thing. I mean, it's, it's the creator still has to do the work. And so like I'm on a content treadmill at the moment. I took a 3-week break these last few days and that was the first time I've had in a long time. But does anyone know this person named Craig Fuller? Do you know Craig Fuller? Oh, FreightWaves. FreightWaves. So you guys should check this person out. He's real low key. He never brags about himself. Off, but it's this guy named Craig Fuller. He started this thing called FreightWaves. For some reason, I have no idea why, they reveal all of their revenue and all of their profit, just like you. But I don't know why they do it, but they treat their company like they're publicly traded. And so you can just Google FreightWaves. It's a software and media company. But his side hobby that this guy has done, it's wild, is he bought this— he calls it a magazine. I guess that it is still literally a magazine. He bought flying.com, which is a very small niche website for flying enthusiasts. Then he bought, I think, 80 acres of land in— I think it's a lot more than that. Is it 800? Did I get it by a factor of 10?

To fit a runway on it, it's got to be big.

I forget the number. Whatever the number is, I think he spent mid-seven figures, I believe, on buying this land. And he was like, "I'm going all in. This is a big deal for me." And what he's doing is he's creating basically like a— You know how there's communities where there's houses around a golf course. His whole thing is he's doing it around an airline, like a strip. And I think I heard about that in an airplane hangar. And he's creating like a flying club. So if you're, you know, Nathan and you like, I would love a home that has a strip, this is what I'm going to do. And he's using flying.com, his audience now, which I don't think it's very big. I would imagine it's like 300,000 to 800,000 monthly uniques if I had to guess.

Yeah, maybe even less than that.

Maybe less. And he put the money down for the land, which was a big deal. And then he pre-sold plots of land and now has made his money back and he's selling it to the flying.com audience. Now recently, I think he went and bought— how many more titles did he buy? Like another like 5 or 10?

They bought a bunch of stuff.

So they bought more. So they bought like the flying.com of the trucking industry. They bought the flying.com of the yacht industry. The yacht industry.

And so I, I The trucking industry would be what? You drive your truck into— You want to park your truck?

I don't know what the scheme's going to be on that one, but he bought a bunch of them. And so what he does is he makes profit. So if I had to guess, he buys them for 4 to 8 times EBITDA and he makes profit to hope to pay back the money it costs to purchase the titles. And he runs the company and then he'll either raise money, which he did in this last deal, to buy either property. So the yacht one or the marine one, that's a very easy one to make here. And we're going to make both homes around a nice marina, but that's his whole plan at the moment. And I think it's going to work wonderfully. That's interesting. I think he's going to— his name's Craig Fuller, F-U-L-L-E-R, and he talks about it, but he has a pretty small following.

Yeah. I think a couple thousand followers on Twitter. It's not— maybe it's 100% going to work.

I think horses would be another good one.

That's where My ranch was purchased from a community that was supposed to be built around equestrians, right? So like it was all these plots of land and it was like it has a room for a stable so that you, if you are a horse enthusiast, you want to have your horse at your home instead of—

1,000 times better than selling a $20 t-shirt, you know what I mean?

It can be, but this was actually a failed community. Like it didn't work.

And so the risk is huge. Yeah.

So then basically the The people who owned my property before I bought it bought like 5 of the plots and put them all together and then turned it into this like 50-acre property.

Well, so I wonder what distribution the failed one had, right? Did they have—

Right. They didn't have a community, right? They didn't have a YouTube channel for horse enthusiasts, right?

Or they didn't own the biggest flying magazine, which is a pretty small niche still. But right. I think it's fascinating going in and buying, you know, a flying magazine and saying, okay, Here's a business. Let's evaluate it at face value. Okay, we've got advertising. Yep. This is cash flow positive.

You don't need that many people to see, to spot trends. I remember when the Hustle Zoom, the company Zoom advertised with us before the company went public and I saw how many clicks we drove them and I was doing the math and I was like, a lot of people must be buying this stuff. This is insane. And I bought some of their stock, like right where they like IPO'd and like you. And at the time I think we only had 500,000 people. You don't need that many people to start seeing like really interesting trends where like people are buying this, this is wild. And, and that was a big learning for me.

One of the things that's interesting for some of the examples, not necessarily the flying one, but it doesn't actually have to be this really unique thing. Like Hampton is not that unique. It's not unique at all. Even ConvertKit is not that unique, right? What I'm doing is not that unique either. So I think sometimes people think like in order to come up with that billion dollar idea, it has to be like, like some, some idea that comes down to your head from God. And it's like, sometimes it's just like, oh, I see a version out there. Like basically my business was because I went to conferences where everybody who was speaking was a white guy and I was annoyed that there were no women and there were no people of color on the stage. And I went a couple of years and then I finally decided, okay, I'm going to stop being pissed and just create the competitor that's better, you know, and that's, that is, has diversity and inclusivity at the center of it. So I just created my version of it, which has, you know, taken off because it was a need in the marketplace. So it actually— it's like the same business that so many people have, but just the, the one unique insight or the one unique perspective is what helps it to take off. So you don't have to come up with the most amazing idea. You can just see what's out there and see like, how could I do that a little bit better? Or just come up with an offer like in Ali's case, right? He's a productivity expert. So like he just needs to come up with either a software or planner or something. And when he does, that's going to take off too.

Well, and sometimes people stick with it for a long time before they find the thing, right? Does anyone drink Element? Like Element tea? So Robb Wolf was like one of the pioneers of the paleo movement, maybe the main pioneer of it, right? He did a bunch of different businesses over time. He tried a lot of different things and they've been working on Element for 5, 6 years now, and it is now really, really taking off. And that's a fantastic business. Also, a little side note, Jill Runyon and I were nerding out about, about this. But if you think about like different brands and the pros and cons of it, right, we have Liquid Death here up on stage. This is a very expensive product to ship, right? Like we're, we're shipping water around. This is very expensive to move. But if you think about Element as a business, right, We're shipping little tiny packets of salt, right? These are electrolytes. And that is a much, you know, there's no shelf life. It's very, very stable. It ships very cheaply. And so there's a lot of these attributes. I guess the first point I was making is sometimes it can take a long time to find the right business, but that will eventually pay off. And then the second thing is there's a lot of these attributes that really do matter. And it's easy to be, to say like, oh, this person did this and it worked and that. But you like really pay attention and find the trends of, okay, what actually made something a good business instead of a tough business? Like this business is very challenging with margins when you're shipping it, but if it's sold in stores, okay, all of a sudden it's a really solid business.

Supplements seem to be huge. I was saying earlier about Nicole Cain, who is— she used to have a blog called Nicole Bitchy, which was like a gossip rag. Has anybody heard of it who's here? No. Okay. Well, anyway, it was a celebrity gossip blog and it was extremely popular. She sold advertising, made a ton of money, and then she decided she didn't want to be associated with, like, gossip about celebrities. And so she changed the model. She just closed that and created a new media site called XO Nicole, which is, you know, like wellness and lifestyle media company, like just creating content and geared towards, I think, mainly women of color. And that did really well. She sold it. I don't know exactly how much she sold it for, but now she's created a supplement business called My Happy Flow. And it's all about like, you know, hormones for women and basically managing your period so that it's less painful and less stressful, whatever. All these benefits to the supplement. Anyway, that business seems to have taken off and it's a subscription model too. So you like get it delivered, you know, and she works 2 hours a day, she told me. And she's got like somebody who ships it out, like a company that does that part and It's very low effort and she makes a lot of money from it.

One thing you touched on of it being a subscription business, almost all of these that you see are businesses that have a recurring or a repeat purchase. There are exceptions, right? Like the airplane tug, you're going to hopefully buy that one time, should last for a very long time. It says it's the best tug, so it should.

Or buying a plot of land to fly in, although you could repeat that in different locations. You could.

Yep. And there's different things you could do there. But another example of someone who's doing this right now, like we've talked on the show about Paleo Kitchen, right? And they had this big exit, you know, blog to consumer products company. But someone doing it right now is Suzy Bullock, who has a blog called Hey Grill Hey. And so she is doing all these recipes, barbecue, grilling, built a massive blog making over $1 million a year off the blog. And then now she is building her own line of barbecue sauces and rubs and getting distribution in stores. And like, I don't know her revenue. I'd say it's like, if I had to guess, I'd say it's like mid-single-digit millions. So maybe $3 to $5 million a year. But it's one of those things where I'm like, okay, you have the audience, you've got the angle on the content, you're just starting to get the retail distribution. Like, I see how this plays out. And it's a product that if you like it, you're going to be buying it every couple months or every month. And I think that one is absolutely going to kill it.

Yeah. You know what's interesting to me? Coworking spaces. Like, obviously we worked in and do well. The Wing, they failed too, didn't they? They did. But it's interesting. I was just at an event for Miss Skittles is her name on Instagram, but her name is Mary Seats and she has a coworking space called The Bakery in Atlanta and it's It's focused around women, mainly women of color, and it does really well. It's very successful. And so her plan is now to scale it and now build a bakery in different cities. And this is like the fastest growing segment of entrepreneurs is women of color. So I'm interested to know, like, have y'all seen a coworking model work well? Because it is a subscription. And then she also does events there. She said it makes a lot of money.

I have not seen it do well. I just want to compare for a second the margins between like a coworking business and like, okay, I'll pay $300 a month, $500 a month, I don't know, to get access to this. But they've got to have a full building. They have to have staff. There's so many things. It's got to look nice. And then if we compare that to Hampton as a business.

Yeah, I would never get into real estate. It's just like it takes money to make money with that. Whereas the way you win in your dollars Yeah.

The way you win in real estate is that you buy the buildings and then you lease it to the company, to WeWork. And so it's basically what Adam Neumann did. It's like, well, here's what's interesting.

And it's a totally different skill set. Yeah. Of like being like a financial analyst versus like inventing things on the internet.

Well, one of the— what she did that's different is she's not like in downtown Atlanta. She's a little bit outside of Atlanta, which means that there's a lot of great parking. It's in a place that that's gonna get less traffic and I imagine it's less expensive to have the space there. Yeah, that helps. So it's interesting. I don't know. I mean, she seems to be doing really well and plans to scale it. So I'm excited to see her do it.

Yeah, that'll be good. One thing I'd love to do is take some questions. We've got a mic that we can pass around. Who's got something that you wanna ask or if you have an example of a creator making the shift right now that you'd love to share, we're down to hear it.

Thanks, guys. So I know Nathan and Sam, you guys both work a lot around like email and talk about the importance of distribution. I'm curious how you see distribution developing over time, namely like inbox service providers or Apple or Google basically taking more control. And then on the other side, social media, you know, obviously there's been a lot of movement. So how do you see distribution in the future for creators? And is it a problem where it's something that there needs to be alternatives, or do you think the existing tools get the job done? I'll give a very short answer. You're better to answer this. The first month that we made $1 million in revenue, I got this tattoo on my leg and it's a pirate ship and it says Boldfast Fund because that was like our motto. And I used to say that The hustle's a pirate ship and every email subscriber is just a little bit of wind in our sails. And the reason being is that my opinion at the time, and it still is, was that email was the most— was the channel that you could own most, but you don't actually own it because Gmail accounted for— you would know the numbers— for us, I think it was 50 or 60%. Yeah, that sounds about right. And if they made a change, which thankfully the only change that Gmail has made in the last 20 years is they've done promo What are the 4 like folders? Updates, inbox, promo updates. That's like the only change they've made really. I hated that update. Yeah, that's like the only thing they've done. But if they made another one, I would have been screwed. So my opinion is email's still number 1. I forget all the other questions that you had asked.

I'm sorry, but you can remind me. There's some really—

I mean, there's a lot of, you also asked about social media and stuff like that.

You don't have to explain. Excuse yourself, Sam. You're good. No, so email is interesting because there's not a single inbox provider, but Gmail does absolutely dominate and then Apple Mail.

How much of ConvertKit is Gmail?

Of the subscribers? It's hard to say because you don't know about the number who are using like Google Apps for Domains, which is effectively Gmail. But it's— if someone said it was 50%, I wouldn't be surprised.

And then Apple's like another 25%? Apple is huge.

And then a lot of those Gmail addresses are actually opened in Apple Mail. And so you get a huge range of things. So you're having these shifts, right, where the inbox providers— and this might be too nerdy, but the inbox providers are both saying keep your list very clean, unsubscribe anyone who's not actively opening, and then they are actively destroying access to all of your data in order to do that very thing, right? So Apple doing their privacy protection stuff where they're automatically opening a bunch of emails there's things you can do around to try to understand, like optimize for clicks more than, than opens. But it's definitely a changing landscape. The thing that you still have, one is that direct access to the audience and right for Gmail or Apple to remove that access, they're actually hurting their customer, right? Because if you think about it, they don't want to leave a door open for someone to come in and displace Gmail, right? So they need to make sure that they're keeping each Gmail user really happy. But then the other thing is, I don't think those algorithms are going to change in a meaningful way because people aren't really— like, if it's not broken, don't fix it.

And of all the channels, in my opinion, email is the easiest to acquire customers repeatedly and quickly and cost-effectively, which wasn't the case when we started. Right. Now it's different. It's way easier.

There's no other channel that lets you actually segment your customer base. right? You can't really say, hey, I'm gonna put this Instagram reel, but it's just for the business owners in my audience. It's not for the people who follow me for my fitness content or productivity, right? But email, you can 100% do that. Like, imagine in Instagram if you put out a reel and it was actually different, like the middle section was different or the call to action at the end was different based on who was consuming it. You can't do that, right? But in email, you absolutely can. So I think we're gonna hold on to a lot of that like ownership and value for a long time.

One of the things we're doing is we text as well. So like emails and texts, I feel like you almost have to like 360 surround your audience, you know, like so social media and then also text, then also email. It's like, how can I show up? How many touchpoints can I have with the same information? Because people are ignoring a lot of it or missing it or whatever.

So I would add into that to do retargeting. If you have email addresses for people, right? Say if you're selling a course and you know everyone who clicked through the sales page, retarget them down your funnel with more content about it. You know, they've been to your sales page, you know, they're a subscriber. You can send them like very targeted content across the social platforms tied exactly to where they're at in the funnel. You have to pay for it. And some people are saying like, why would I pay for that when I can email and reach this person for free? It's like, well, like you get to hit it from a bunch of different angles.

Exactly. And I find that, that we have to do that. Yeah, but I do. I love abandoned cart sequences. It's like my favorite thing.

Yeah, there's all kinds of different things.

It just works so well. I don't know why, but they kill it. All right. Who else has a question? Rachel and Nathan, thanks for your time. Sam, quick question.

Congrats on your baby, by the way.

Thank you. You're welcome. When you were talking about monetizing your newsletter and you gave that equation, like number of people you reach times your influence Can you share how you thought about quantifying your influence? Yeah. So I'm like a nerd and I like started thinking about this math a lot. So it's so funny. I was just like drawing this out today. There's like a sub-equation of influence and I'm trying to work out what it is. Cause I like these like framework. I try to oversimplify some things and it's fun, but typically the amount of influence you have on someone, I think it's often correlated with the amount of time they've invested into you. Consuming your thing. And so, an example of that is I used to think YouTube was the number one best channel to influence someone. I've since changed to podcasting because I'm in someone's ears roughly 2 to 3 hours a week and it's very intimate. And I have noticed that I will do little Easter eggs where I'll say something in the middle of a pod like, "Contact me if you heard this," something silly. And way more on podcast. And so for influence, it's a really easy way to test it is how many people will show up to an event. That's a hard test in, in the sense it's hard to pull off, but it's very straightforward. But usually it has to do, I think, with the amount of time they've spent consuming your content and how far they go down that slippery slope. So usually, not always, it's like a book. Someone who spends 8 hours reading you will probably love you more than someone who has listened to you for 2 hours versus who has just seen one tweet. And in fact, I know a lot of friends that are famous on TikTok when they try to sell stuff, they don't sell anything because they only have 15 seconds of someone's attention.

That's such a good point. That's why I think books are really powerful. I mean, books definitely— my book definitely blew up our business. And I think it's somebody has spent that much time. Most of the audiobooks sold 3 times the amount of the hardcover. So you're in someone's ear for 8 hours. I'm reading the book and people tell me all the time that they listen to it like regularly, like they've listened to the audiobook multiple times. So that's a lot of influence if you think about it.

So yeah, I think it's a time thing. Yeah.

And that's where like a podcast is great, just the sheer amount of content that you're producing, right? You can't produce that many books, but you can come out with new content every single week.

Well, that's one thing to think about, like what are you giving your audience to consume? Right? So if you're not regularly creating newsletters and a podcast and, you know, maybe you're doing events occasionally and you're on social media or whatever it is, right? Like, what are those touchpoints that you're giving your people so that they can regularly be consuming something from you and learning from you or just getting value from you in whatever format? So that's one of the reasons why this podcast exists, because I would tell my people all the time, like, always have something positive in your ears. Always have something that's like motivating you so that you can kind of stay motivated even when business is hard. And then I was like, well, I'm not really creating anything to help with that, so I'm just sending you to other people's podcasts. So maybe I should get back to actually doing it consistently. Yep, I like that.

I think you got the mic right back here. Hey Ethan, thank you guys so much for sharing your wisdom. Honestly, question more of big picture. So you guys have been entrepreneurs and creatives manifesting your dreams for years. And I'd love to hear your insights about like what the meaning is when you accomplish these things. How do you stay grounded? How do you continue to build something new when you've already done what 10 years ago you would have said is it all, you know? Do you do meditation? Yes. Yeah, I'm a yoga instructor.

So I'm, I love I love your vibe.

Yeah, I'm very curious about your answers.

Well, I'll say for me, I have a big mission. And my mission is to close the wealth gap for women and entrepreneurs of color. Thank you. So that's what motivates me because otherwise I'd be like, why do I work? I mean, honestly, I think we all want intellectual pursuits. So I think I would still write books and do things. But what gets me to show up and— I, you know, want to keep going with my business. And what has gotten me through the really hard parts is having that mission and knowing that if I stick with it, I'm going to continue to impact more and more people and help more and more people, you know, close that gap for themselves. Like, it's one entrepreneur at a time. So I think having a strong mission and why, it keeps you motivated long term and makes you want to keep creating.

For me, it's a lot about— I just, I find it quite addicting to come up with an idea and turn it into reality and hope that I can kind of like kick my dent in the world. I find that to be a very addicting thing to like bend reality into how I want it to be. I find that to be— it's almost like exercise. You're like, I want to lift this much weight. You train for 3 months, you hit it, and you're like, that was so exciting. I'm so proud of myself. I want to do it again. And then the other half is just like proving every like high school bully and girlfriend who dumped me wrong. And making up for like years of feeling inadequate. And it's a very honest answer. There's definitely bottles of champagne of all the grudges that I hold. And then whenever I, whenever I do something, I can rub in their face. I pop one of those bottles.

I'm just imagining in your house, Sarah's like, why do we still have these? And you're like, they know why. Yeah, I'm plotting. Yeah. I think for me, it's just fun, right? Like the game of business that we're playing is, I just thoroughly enjoy it. And I really, I think about setting a big enough goal that achieving that goal is going to force you to change and become a different person. Not in the way of like, oh, now you're a douche or you've sold out in some way, but in the like, I had to become the person that can achieve this level of thing. So I had this experience at our very first team retreat where we had 21 people on the team. We got together for the first time. We're in this big living room in a cabin outside of Boise, and it was a great moment. I was sitting around looking at this, people were meeting for the first time, and I was like, "Wow, I love this." And I realized they were all waiting for something. And I'm like, "What are we waiting for? What are we— Oh, you're waiting for me to say something and lead this company." And so, in that moment, I had to shift from being like, "Oh, I'm just behind the scenes. I'm just working on these things," to, "Oh, I have to show up and lead this company." I had to learn new skills and level up in that way. And so, when I think about building the business to $100 million in revenue, which is the goal that we're working towards right now, I'm realizing I'm going to need a couple more step functions of those to learn new skills and entirely level up. I'm excited for that in the same way of like the way you talk about a fitness goal and achieving that. Like, I'm excited to figure out how I'm going to need to change to do it. And then also on the mission side, like the mission for the company is we exist to help creators earn a living. And so I—

Is that your number one motivating factor? What's that? Is that number one or is that like number five in things that like motivate you?

I think it is number one. And if I like told those stories, I would cry on stage. And so like Alexis is sitting there, she was at that team retreat. She knows, you know, all of those stories. And so, but yeah, it's definitely number one. It just would get into like sharing a bunch of stuff that, you know, there's a documentary that you can watch for that.

You want to do one more?

Yeah, let's do one more. Who's got it? That would be me.

Oh, you've got it right there. Hi, thank you for your time and big powerful missions. I really appreciate what you do.

I'm one of those— Hold that up. The mic in. Hold the mic to your mouth. Yeah, give her the book.

Hold the book too. Okay. Okay. My question— I had so many questions, but I'm going to narrow it down. So I'm a recent empty nester of 3 kids. They are off, you know, in the world now. But I always felt like running a business was pushing up a boulder up a hill as a woman in the household and having— I don't think that's— I don't think that's wrong. Okay. I wasn't going crazy. Sounds accurate. Well, I would say starting a business is like pushing a boulder up a hill. For sure. It's been, it's been 10 years. It's always been like, but because of all the, the cultural, I guess, pressures that automatically go on the woman and when the male is in their, their career and it's just, it's a lot. But I'm asking because even though I'm 2 months into this, I'm still curious, how do you all balance family and business? Without feeling like you are pushing that boulder up a hill? Yeah, well, sometimes I do feel like I'm pushing a boulder up a hill with balancing both, and there were definitely times where it took a lot. I mean, I just had an arrangement with my husband where he didn't like his job, I loved my business, and so he stayed home with our kids, and he was great at it for the time that he did that, when— before they were like school-aged. And that was our— that was our deal, and that's how we did it. But the way that I do it is with lots of help. So I higher, higher, higher. I, I would rather have less money and never cook and never clean and never do all the things that I don't have to do. So I have a chef and I have a house manager. I have a team at home that allows me to do my work, and then when I'm home, I'm 100% just focused on my family, or unless I'm taking time for myself. So I don't have to like go home and cook or go home and run errands or go— I don't do any of that. I hang out with my people when I'm home, you know? So that's, that's how I balance it. And then also hiring a team in my business so I'm not doing everything. So I've given up— I could take home a lot more money if I didn't have a team, but I also wouldn't be building a potential billion-dollar business. But yeah, so team is huge. So I hire and hire early and as fast as possible. That is key for me to be able to have that balance. I have 4 children. And I started having babies 6 months in. I just decided I was going to become an entrepreneur. 6 months later, I accidentally got pregnant. 19 months after my first child was born, I accidentally got pregnant again. So good at business planning, terrible at family planning. And then there's a third accident, and my first child is my bonus daughter. So yes, 4 kids, and I built this business the whole time I've been a parent. For, you know, from 6 months in. So it's very doable, but you have to hire help. That's, I think, the key. And then also have strong boundaries and say no to a lot of things.

Yeah, I think I have two different answers to that. One is early on when Nathan also has 50, 11 kids, so 3 to be specific.

Yeah, but you had kids at a really young age. Yeah, I was 21. You had kids before you even started ConvertKit, right? Yep. Which is— I always thought that was very impressive.

Yeah. And so there are two, like, there's basically two different phases for us of having kids where the first two kids we had when we were really trying to get the business off the ground. And that was really challenging at oftentimes because first I had to be very deliberate about the amount of time that I could spend and how intentional I was about it because I was used to being able to just throw a huge amount of time at any problem. And then once you had kids, you realize like, oh, I can't do that anymore. And so my like messing around of like, yeah, yeah, I'll spend 6 hours to solve this problem. I couldn't do that. And so I had to actually be super focused.

Well, that's what I was going to say. It almost gives you a superpower because you're really intentional and you're like, nothing is wasted, you know? Like, I'm not going to sit here and screw around on Facebook. I'm going to sit here and get shit done because I know I got to be done by a certain time. Yeah.

So I think when my first son was born, the next like 2 and a half years was that where I was really intentional with my time. I was on it. I was writing a whole bunch. I made sure I wrote 1,000 words a day. And that was the most important thing. If I didn't get that done, or like everything else was negotiable, but that was the one thing that always had to happen. Now, when my second son was born, I was trying to take on even more. And I was thinking like, okay, I got that figured out. We'll do this next one. Like, I can take on even more. I've leveled up as an entrepreneur or whatever. I actually got so stressed that I got shingles. And like didn't work for 6 months and it was a terrible thing. So I tried to like push through that and, and it didn't work. And so I think early with kids, before you have the money to spend on help, you have to be realistic about like what your appetite is and what— like how you spend your time and just be super, super disciplined. Later on, like my youngest is 4 now, so I have a 5-year age gap between my older 2 and, and my youngest. And it's kind of a cop-out answer, but like a lot of problems can be solved with money, right? And hiring— So true. Hiring help, you know, and having a nanny come and all these other things. It's just like this makes things so much easier. And then being able to step away from the business, right? In the early days of ConvertKit, if the app went down, I had to be either helping get that back up or answering tech support or whatever else. And I had an experience a few years ago. We actually had a team retreat where We had an issue and a bunch of people gathered around. I'm like, wait, there's like 25 people standing here who are more qualified to deal with this than I am. Like, I could add nervous energy to this, or I can go sit down and have a conversation with someone else who's equally useless in this situation. And so that comes with time. And so I had an entirely different experience raising my youngest because we had money. We were not stressed.

The same was the same. We had a 5-year gap between my two the two in the middle and the youngest. And it was— it's night and day. Yeah.

Sam, as a 3-week father, what would you say about this?

I had the greatest advantage I felt when I started my company was I had a girlfriend who I'm now married to. I didn't drink, I didn't work out, I just worked like a lot. Like, I didn't have any— I just explained to you, I don't— I would not leave my house for 3 weeks at a time. Now I like barely did anything, so I didn't have balance. Months. And I paid for it with my health. I had high blood pressure and I don't think I was emotionally in a good place. But I'm thankful I had a strong girlfriend who kept me going. But no, I didn't have balance. I kind of think when you're getting started and you're just trying to make it work to get to the point where you could hire people, my realistic opinion is I don't think you can have balance. I think it sucks. I think it sucks. I mean, that's the truth. But you're paying the price for 1 or 2 years to hopefully not pay the price for the next 10 or 20 years. I would tell myself a lot of amazing things have been built from midnight to 3:00 AM. And this is just going to be another example. And I just didn't have balance. Now, I have a ton of balance. I work a normal 40-hour work week and I feel happy. But I was unhappy then. And I'm happy I was unhappy then so I could be more happy now.

There's a phrase that I might have said it before on the podcast. I'm not sure. I actually heard it from Catherine. Catherine, do you remember the Rudyard Kipling quote? Do you remember it on the spot if I give you the mic?

It might not be exact quote, but it says something like, you can have anything you want, and if you don't get it, it means you either didn't want it or you tried to bargain over the price. Yes.

So like that stuck with me. You can have anything you want in life, and if you don't get it, it means you either didn't really want it or you tried to bargain over the price. And so when Sam's talking about like not having that balance, it's not saying you have to live that life. It's just saying, do you really want it? Like this, this goal that you're setting out, you're saying like, oh, I really, really want this. Oh, that's what it costs. Ah, I'll pay this. Like, this is what I'm willing to put in. And sometimes that is actually what it costs. But other times you're like, okay, that means that you're not going to get that thing. And so I think as we talk about this idea of building a business at this scale, right, we're talking about something that is immensely hard, right? All of these people, everyone who's built an audience, is now trying to tackle this next mountain that's even harder. And we're saying, I think we can do it. You know, I owe it to our audience, you know, or I have this chip on my shoulder that I have to prove something. And so like, this is what I really, really want. And it's like, all right, be honest with yourself about what the price is and if you're willing to pay it and, you know, what the terms are going to be. And then if that's not what you want to do, like, that's totally fine. Go pursue something else, right? Like, you're in this room, you've probably had some meaningful level of success and you can do but don't ever have it where you're sitting back and saying like, I wish I would've done that and I wish I hadn't bargained over the price. So that's all we have for you tonight. Thank you so much for coming out.

Thank you for tuning into this episode of Billion Dollar Creator. If you enjoyed this episode, please like and subscribe, share it with your friends, and leave us a review. We read every single one. If there is a company you want us to profile on Billion Dollar Creator, send us a message on social media and we will consider it. Thank you, and we will see you next time.