Greg Isenberg: How to Successfully Build a Portfolio of Companies

Tim Stoddart: Hey, everyone. Welcome to the Copyblogger podcast. My name is Tim Stoddard. Thank you so much for joining me. My guest today is Greg Eisenberg. Greg, what's up, man? Thank you so much for coming on the show.
Greg Isenberg: It's a pleasure and an honor to be here.

Tim Stoddart: Stop, I'm not that cool. I promise you.

Greg Isenberg: All right. It's not about you, Tim. Actually, it's about Copyblogger. You know, I've been following the the the amazingness for Uh, I don't know, 15 years. Is that possible?

Tim Stoddart: Yeah. That's how long I've been following it. I only took over. Well, took over in bits and pieces. You know, I bought like chunks of equity at the time, but I'm the full owner of it as about five months ago. So, um, I really appreciate you saying that. Thank you so much. It's an honor for me as well. You know, I think it's always like pretty funny because, uh, it's, is one of the good, the great things. And one of the bad things about the internet where it's like, I'm still the same person that I always was, but now like I'm the guy from coffee blogger and all of a sudden, you know, people want to talk to me. Um, so that's, that's pretty hysterical, but, but nonetheless, it's, it's an important brand and like, I take it really, really, really seriously. It, it, it changed my life. And so I really, I feel like I'm, I'm carrying the torch for, for the next round of writers, if that makes sense.

Greg Isenberg: It does. It does. I look forward to seeing what you do with it.

Tim Stoddart: Thank you. All right. Well, I'm going to start at a little bit of an unconventional place because, um, one thing that is a little bit unique about you and your business is your website, your late checkout dot studio website. I gotta tell you, man, I've never seen anything like this before for anyone who's just listening to it. Um, The website is basically like a 3d interface that kind of looks like a theme park. I think that's what you were going for a theme park, like a, a town, a town square. And then as you scroll over the front of it, these little buildings kind of pop up and these buildings essentially turn into the links, which link out to. To the different brands and the companies that you own. So I know it's like kind of a weird place to start, but I just, I got to know about this website. Did you come up with this idea or did somebody put this together for you?

Greg Isenberg: So I came up with this idea at Disney World in Orlando. And I was walking through Disney World and just noticed how incredible everything was designed. The smells, the buildings, the neighborhoods, just everything was really thought of, well thought of and well placed. And Later I watched the Imagineering documentary about the Imagineers, the people who actually come up with the concepts for the rides and stuff like that. And they take it really, really seriously about immersion and creating a space that people want to stay a while and that they sort of, you kind of lose sense of where you are. And I wanted to do something similar with the website. So when you go to the website, You know, it feels different. It feels like a place. It feels like a place that you can explore. And because Late Checkout is a holding company, meaning we're a business that owns multiple businesses, I wanted people to, yeah, just treat it as like, you know, the the quote, buy the ticket, take the ride. It was almost like you were buying a ticket to the experience. And this is just the tip of the iceberg. We're actually like adding a ton of new Easter eggs and immersion to it. So stay tuned. But and then I will say it doesn't hurt that we have a innovation agency called Late Checkout Agency, which I just went to them one day and I was like, hey, what would a website that looked like Disney World look like? And because they work with the largest brands in the world, like Nike and Shopify and Dropbox, they were like stoked. It's like my own like digital Imagineering team. And I will say, I'll say this, I'll say that While it might look like the website isn't a conversion machine because it is not standard, the brand and the word of mouth that is built has 100% driven, you know, millions and millions of dollars of revenue just from that website. So highly recommend. If you're looking to build a website, think about, and you're looking to build a brand, think about how can I make this unexpected.

Tim Stoddart: Yeah. What's the expression? Like, don't be better, be different. It's, it's certainly different. I've never seen anything like it. Um, okay. There was a bunch of places that I was thinking about going and talking to you. You and I just recently started chatting through Twitter. There was a tweet. It's more like an essay. Now that Twitter's or X, excuse me, is a little bit more long form now. And so I want to talk about that, but before we get there, man, um, You mentioned late checkout being a holding company, and this is a theme from last week's episode. And it's basically what I'm doing with, with my own career, where you no longer have to be like a private equity firm to build a portfolio of businesses. You know, like you can be a person, you can basically be like an individualized. I like to think of it as, as kind of long tail, right? Like every person is a media company. Every person is sort of turning into their own. their own holdings company. Was this the plan for you all along? Did you always have this vision of you being like just an individual entity that would start businesses and gobble up equity stakes and other companies? Or is this something that just kind of happened?

Greg Isenberg: This actually, I had this idea, um, and, you know, 15 years ago. Um, and I had a name for it and it was called islands. And the idea was. I was going to have these different businesses, different islands, so to speak. And I had recently moved to San Francisco, Silicon Valley, and gotten to know these pretty well-known venture capitalists. And when I pitched them the idea, I was like, oh, my dream is to build this holding company and we're not going to raise money. We're just going to have a bunch of businesses. And they told me that it was a bad idea, basically. And I was naive. And I listened to them because, you know, I looked up to these people. These guys were my heroes. And I ended up actually, a few years later, ended up turning islands into a venture-backed startup. So I actually created a venture-backed consumer social app called Island, which sold to WeWork. And that was a whole other chapter in my life. But it was only until COVID. I think a lot of us had this epiphany during COVID where it was like, life is short and anything could happen. And you want to be doing your life's work if you can, if you have the privilege to work on your life's work. And I remember thinking to myself, that original concept of islands, like, I want to do that. And I wrote a blog post in early 2020 called, Why the Future of Startups is Product Studios, or our product studios. And I talked about what what basically became the blueprint of what I call multi-preneurship, someone who builds multiple companies under one brand or people call holding companies, some people call it personal holding companies. So I brought back that idea and I will say that it's been the most fun I've ever had career wise.

Tim Stoddart: I certainly relate. I'm going to stick on to this because it sounds like We had similar journeys just in terms of our mindset. I read a book years and years ago called the one thing, which is a pretty. Popular book these days is written by, um, something Keller, right? I forget his name. He's the guy that had that huge, like real estate company and the whole book was just about focus and about only working on, on one thing. And so for the last 10 years, I've, I've really took that book seriously. I don't know why just the thought of like coming up short. When I had this one thing that I knew, if I just focused on that, that could really be a winner for me. And, and it has been, it's an agency that, um, most people know this. I got sober years and years ago and I created an agency that like specializes in working in behavioral health. And it's been like, great. I mean, it's, it's been hugely successful. Probably the reason why I've been able to do a lot of the things that I've been able to do, but somewhere along the line, I had a similar epiphany. It wasn't necessarily. COVID related, it was like family related. There's just a family experience I had. It was like, you know what? I like working on different stuff. I love working on my behavioral healthcare industry. I like writing creatively, you know, copy blogger was a huge part of my life. I like being in the content marketing space. Um, some other things that are healthcare related. I like, and so. It was, yeah, it was like a real fucking moment where it's like, why not? Am I going to look back at this and like regret? not doing the things that I always wanted to do. And I think that this thought process isn't necessarily unique to you and I. I think a lot of people are starting to see this where it's like, wait a minute, I can do this. There's like a world of possibilities out there. And I think we just got to go for it. Right.

Greg Isenberg: Yeah. I think human beings, whether we like to admit it or not, seek to do things that are high status and When I was in my 20s, doing a venture-backed startup was high status. Raising money from Sequoia or Andreessen Horowitz, that gave you the stamp of approval that you're doing something cool. Getting a big check from a venture capital fund was really cool. And seeing your valuation go up and up and up and up was high status. All these things were high status. The interesting thing is where the alpha is, meaning where the opportunity is, is actually things that are low status that turn into high status. So. When I started a holding company, you know, three and a half years ago now. It was very low status to do it bootstrapped, especially, you know, maybe if I would have raised millions of dollars, it would have been medium status or medium high status. But my point is. Well, first of all, I agree with you, we all have we all, you know, process life and have these crossroads and then have these realizations, especially as we get older. Memento Mori, meaning like, you know, you. You understand that you have more, you know, a certain amount of days in this in this life. And you're kind of like, I want to go do what would be the most fun and most fulfilling to me. And if that's something that's low status, I don't care. And I'm okay with like going to a cocktail party or a dinner party or wherever and being saying, I'm the CEO of Late Checkout and we own a bunch of internet communities and we own a bunch of agencies, design, growth, and being OK with it, you know, versus, hey, I run a billion dollar venture backed thing that has raised two hundred fifty million dollars, but has like two weeks of runway left. So it's like on the outside, it looks like I'm killing it, but on the inside, it feels like you're on this treadmill. And that was my big realization, having moved to Silicon Valley had that huge experience, been a part of WeWork. You know, my last company sold to WeWork, and WeWork is like the epitome of when venture capital goes wrong, what happens. And yeah, my only like takeaway from that, I mean, I guess my biggest takeaway from that is, and this sounds like very tacky and corny to say, but do things that feel fulfilling and do things that potentially are low status that you think will be high status in five to 10 years.

Tim Stoddart: Both of those things are huge staples for what I've, I've been learning, man. There's like, you're a very thoughtful person. I can tell that you think carefully about what it is you want to say. And so many of, so many of the sentences that you had, I'm like putting little bullet points in my mind to come back to. Because the idea of finding an industry or a niche or a lane that is low status now, that might be high status in the future. I think about this. I don't even know how much, like 40 times a day, every time I'm on Twitter and I see people talking about the next AI thing or the next whatever thing I'm thinking. You're all going where everybody is going. And that's like the worst place to do it because we're already seeing it with AI, just as an example. The only thing that you can really do to make it better is make it cheaper because everybody's doing the same thing, right? It's like very difficult to rise to the top when it becomes commoditized. And me being in, you know, something like behavioral healthcare, super boring, super clinical. Nobody ever looks at this and thinks to themselves, Oh, wow. Like that's a move. I'm seeing these things everywhere. Something that's just like super boring that nobody wants to do. And has huge, huge business potential behind it. And so like, I don't even necessarily have a question here. I'm just kind of reflecting back to what you say. I feel like everybody else is crazy right now because everyone's just flocking to these things where it's like, oh, this is so cool. I want to be a part of this. I want to be a part of this. I'm looking at it. Like, so an example, right? I can't, who knows how many electrician plumbing businesses. Uh, local retail stores. I just wrote a blog about this the other day on my website are going up to sale. Now the boomers are all starting their businesses. Right. And the amount of numbers, or excuse me, the, the data that shows like how few people want to buy these businesses. It's crazy. All of these businesses are cashflow positive. They're all profitable. They've all paid off their bank loans because it's like government loans from 30 or 40 years ago. Right. I see that. And I think go there. There's money there, but you're not going to get a lot of Twitter followers by buying or starting low status, high profitable businesses that way, which is so ass backwards. Hey there, it's Tim. And I need to take a moment to tell you about this show's sponsor. It's a product called Hype Fury. When I was able to speak to Janik, who is the CMO, one of the founding partners of Hype Fury. And he agreed to sponsor the show. I was so thrilled. And the reason is because I have personally used Hypefury for the last three years, and it has allowed me to build my social media following and my personal brand to over 70,000 followers. 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Greg Isenberg: Like I understand why people are driven to high status things. Because I think we all are impulsively. And the thing with business building, which is different from a lot of other things in life, is business building is very long term focused. So you only see the rewards of your work usually after years, years of pain generally. And With things like Twitter, for example, you know, you can tweet about, you know, I tweeted about AI yesterday, I had 1.4 million people who saw my tweet, and I had, you know, 4000 or something likes on that tweet. That made me feel good. That really made me feel good. And subconsciously, I might be like, you know what, I'm going to tweet more about AI now. These are the short term dopamine traps that you can get into, which I think as builders and entrepreneurs, we have to be very mindful of. Are we doing something because it feels good? Are we doing something because other people like our parents or our friends think it's cool to be doing this? Are we seeking validation? Or are we doing this because we think that this particular tweet, idea, business is what's most authentic to you and what you should be doing. So for example, with myself, I really feel is like checkout is like the in so many ways is like the expression of, you know, creative expression, I should say, of a lot of my endeavors. Um, so like I created an innovation agency with my team, of course, incredible team, but I created that because I am that person who loves to like, look at, um, you know, we'll say a Dropbox as a company and being like, if we were to redesign Dropbox, from the beginning, what would that look like? And how can we make it so interesting and different and unique and community focused? So then like, cool, build a business around that. I've always been interested in organic search. So we built a business called boringmarketing.com, which is actually started off as a piece of AI software to build SEO optimized pages that we were just using for our own products. And then we're like, oh, there's probably a service business here. Other businesses can use this. And then we built that business. You probably need a robot.com, which is like an AI and productivity community. So you can just name. Thank you. So I think, you know, the point is the point I'm trying to make, I'm just using this as examples is The cool part about holding companies is you can use it as a way and a venue to express yourself.

Tim Stoddart: I agree completely. It's been, the other thing that you said earlier is it's the most fun that you've had in a long time. This is the most fun I've had building shit that I really can ever remember. And wow, now that you mention it, like it is a representation of all the things I'm into, you know, like I have my whole recovery based media brand. Now that I just bashed AI for a while, like I'm an SEO and we built an AI. Article writing tool, which is going really well. Um, copy blogger, obviously, which was like my education, you know, I'm, I didn't get an education other than, than reading copy blogger, a couple other projects. I'm not, I'm not here like talking about my book. I'm just reflecting on what you said where, yeah, it's like, it's, it's. It's a representation of like the creative aspect of what I, of what I think is interesting, which is also, I'm not, I'm not really sure if there's like a big point there other than for me, it's, it is possible to build, to do the things that you love to do and not get stuck in this thing that you do just because you need to get the paycheck.

Greg Isenberg: Yeah, I mean, that's the point. Like, that's the point you're making, which is. Or that we're both making, I guess, which is like. If we can do it, you can like you, you didn't have formal education, I'm a college dropout, you know, like I. I grew up in Canada, which isn't exactly like New York City, you know, like I didn't you know, you can do it from anywhere. You need an Internet connection and you need the ability to You need to pick a lane that you feel. You're. You know, basically, and and, you know, or you want to know and you have the curiosity to. Be learning in public and. That's what fires me up about the Internet just in general, like even after all these years is like. It's well, I was watching just before this, I was watching like an Instagram reel of this comedian, Andrew Schultz.

Tim Stoddart: Yeah, of course. So he's all over now because he's promoting his his Madison Square Garden thing that he did.

Greg Isenberg: Exactly. So there's this. There's this video of him, like he's in the subway and like Frank Sinatra is playing and he's just like. Getting out of the subway and He's you can just see him like almost like Rocky, you know, climbing up the steps. You know, he's just like so stoked. He's so stoked. And you hear the music is getting louder and louder. And he comes out of the subway and he's in front of Madison Square Garden. He walks into Madison Square Garden and he's like so triumphant. That's how I feel every single morning when I like open up my laptop and I log on to the Internet. Like, yeah, the Madison Square Garden. is the internet for everyone. Like you don't need to be at Madison Square Garden. You just need the ability to pick the lane and find your own Madison Square Garden on the internet and good things will happen.

Tim Stoddart: I want to talk tactically for a second, because this is something I've been thinking about a lot recently, where it's pretty easy to say, if you have a laptop, you have an internet connection, you can do what we're doing. You can create multiple companies, you can buy and or like earn your way into equity of other companies. But I've come to realize that one of the things that is like fundamentally required in the beginning is cash, right? Is cashflow. And I've never raised a dollar in my life. I've, I've never been in that world. It's still kind of fascinates me a little bit. I think it's so weird how it's like a good thing to raise money. Even though your businesses are profitable. I always look at that. Like how did that even become a thing? Right. Um, but I had my agency and although agencies like aren't like we talked about, like high status kind of cool tech products, they're very good in terms of cashflow because they're just instantly profitable. Right? Like as soon as you get your first client, I mean, I suppose you could lose money on it, but it's, it's unlikely. Like you, you're probably have a little bit. little bit of profitability once you have your first client. So I've been thinking a lot about that infrastructure and how it is like, in my case, that boring, heavy cashflow type business that has allowed me the flexibility to pick and choose other markets. Like you have options, right? Uh, correct me if I'm wrong. I, I think I heard this somewhere when you were on, um, on Sam's podcast a while ago where that was your first business, right? Like you got started with. an agency with the service business. And has that happened for you? Has it been that cashflow that you generated that allows you to have other options?

Greg Isenberg: Yeah, I think what's great about a service business or an agency business is, you know, you can build it in a day or less, right? Think about it. You need a brand, a name, a domain and a landing page. That's all you need. That's cool. And then to your point, you get some margin to produce a service. The trap with agencies is as you get bigger and bigger and bigger, sometimes that margin gets smaller and smaller. And there's lots of, I think the average agency probably You know, it doesn't make very much money and is probably around 5 to 10 percent EBITDA, which is not very great, especially considering how much risk you have at that point. If you have 100 employees and you're making 7 percent EBITDA, just like that's scary. You're flying too close to the sun. But yeah, I started off in services because it was the most low status, old school way to build some cash flow. And then from there, instead of reinvesting to build the biggest agency in the world, how do you build more software or other types of businesses that can scale better than a service type business? That's the way to think about it. I think the way to think about it is I'm going to take the cash flow from an agency to build other things that could be more scalable. So, for example, with Late Checkout, the innovation agency, I think we only have 12 clients or something a year, 12 or 14 clients. And we actually max out the amount of clients that we want because we're not trying to grow it to be the next IDEO. You know, someone on a call before this, someone was like, hey, you guys are kind of like an IDEO, but, you know, But, you know, focused on like community based design. I was like, yeah, but in my head I was thinking, yeah, IDEO is like hundreds of employees. I would never want to run that business. So. That's just something that I learned as an entrepreneur building service based businesses is. Write down when you're when you're starting your business, how big, how big or small do you want this business to be and what does success look like? And that might sound obvious, but, you know, you'd be surprised how not only don't don't just write it down, actually, in the beginning, like check in with yourself every three, six, 12 months, you know, because you. You might be growing, growing, growing and then realize, oh, man, like I didn't all of a sudden, I mean, champagne problem, but all of a sudden I'm running this massive agency and like this isn't what I signed up for. What happened to like. The multi printer goal that you were after.

Tim Stoddart: I don't think it's easy to say champagne problem, but I think a lot of people do fall into that trap that you're talking about. I just, I think it's a matter of failing to replace yourself because that's, that really is the trap when it comes to agencies is like you think, and you feel more importantly that like, nobody cares as much as I do. And it's a real thing, you know, it's definitely a real thing and I've certainly been there, but. You got to get out from under it and like continuously replace yourself. If you want your margins to, to be healthy enough to where it's like an actual business that makes money. And the reason why I say that is because I don't think it's uncommon for people to do exactly the opposite when it comes to service businesses, where like you work more to make less. And how do you get out of it? You have to just work more. Right. It's, it's, it's almost like once you get to that point, You can't get out from it because you can't replace yourself without losing a bunch of clients. I've been grateful and fortunate. Like I'm a, I'm a reader. Basically I read all the time and, uh, I've just read a couple of books that I feel. I can't really even claim credit for it. Like it was just the right book at the right time, the right message at the right time. And so I felt like I was always one step ahead of, of falling off the cliff in that way. But I advocate anybody to do it because. Exactly. Like you said, it's almost like you've created an internal funding mechanism to make it so that that cash that you generate and correct me if I'm wrong, by the way, I'm, I'm assuming this is what you're telling me, but that cash that you generate, that you can then deploy to a more scalable type project to where all of a sudden, you know, you're 10 X saying maybe even a hundred X thing on your time.

Greg Isenberg: Yeah, it's exactly what I'm saying. And like the way I see it is like. If you're making a million dollars a year, that's one seed round per year. If you're making five million dollars per year, that's five seed rounds. If you're making 10 million, it's 10 seed rounds. So that's the way I see it, is you're essentially, you're becoming your own VC. You know, when you talk about venture, the word that often comes up is portfolio. VCs talk about their portfolio. And you're doing the exact same thing. here because you're incubating or buying other businesses. The only difference is when a VC writes a check into a seed business, they're buying 10% or something around there, 5, 10, 15% of that business. But the cool thing about this whole multipreneur world where you can reinvest cash flow and stuff like that is, well, you can actually own 70, 80, 90, 100% of these businesses like your holding company can, which is really, really cool because then all of a sudden you have one business and it sort of starts to take off. Then you get this like acquisition offer and maybe someone offers you, you know, eight times profit or 12 times profit, or, you know, maybe it's a fast growing SaaS business and they want to give you 40 times EBITDA, and all of a sudden, you're making life-changing money on selling one of your assets, which I think you're going to see a lot more of over the next few years. You're basically going to have this multi-preneurship movement grow. More and more people are going to become these multi-preneurs. Some of these businesses are going to work. Some of them are not going to work, obviously. Some of these businesses will have to close down. But you'll see more examples of some of these higher beta software type businesses and selling for millions of dollars. And even if they sells for seven million dollars, let's say, you know, that's sounds great. It sounds great. Right. Like, you know, if you actually do the math, like, let's do the math. Let's say you start, you know, here's the VC Silicon Valley way. So. You start, you start a business, you raise, you know, a million dollars in your pre-seed round, 15% dilution. Well, first of all, let's say you have three co-founders and it's a third, a third, a third. Because, you know, in Silicon Valley, they, they look for co-founders.

Tim Stoddart: They need that, you know, and you need to get the top sales guy, the product guy, the operations guy or girl.

Greg Isenberg: So exactly. So you have, you know, you're at, you're at a third and then you lose, you know, In every round, you're losing 15 to 20% dilution. So maybe you go, you know, do a seed, a series A, a series B, and your 33% now is worth 10 to 15%. Again, maybe you raise $75 million, but you sell the business for $200 million. So you sell the business for $200 million, 75 goes back to the investors. It takes 10 years and you're seeing 10% of $130 million. Now, that's a lot of money. $13 million is great, but it's way easier, honestly, to go and build something, scale it, sell it for $5, $7, $9 million. There's just way more buyers at that level, too. And the hurdle is a lot. So I think it's an option. The reason I like speaking out about this whole way of doing business is because I think it's when I was building Island and when I was building my previous company, I never really considered that this was a viable option, but it really is.

Tim Stoddart: I'm glad that you like talking about this because you've been involved recently somewhat recently with, with communities, it seems like online communities is an avenue that you're kind of finding your lane in. And I know you've had a lot of success with that. So I was thinking like, man, he's probably really wanting to talk about his community side business. It was like, ah, you know what, this website is so cool. It seems like we're really similar. So I'm, I'm, I'm glad I touched on this. Cause I can tell you're passionate about it. I want to touch on one of the downsides though, and get your viewpoint, which is. I do think there is something to. the concept of like spreading focus out in a bunch of different ways. I have my own kind of opinion on it, and maybe I should say my own, like how I mitigate that. But what are your thoughts on that? Do you think that is something that could be troublesome for people? And how have you made it not so?

Greg Isenberg: Yeah, I think it's a mistake that someone can make is being like, okay, I listened to Tim and Greg speak and I want to be a multipreneur and I'm going to go build five businesses this year. And I think that's a mistake. I think, you know, you mentioned community, like to me, to me, like community is just like a method in order to build attention and build trust. Like that's why I love Internet communities. So I pick a niche. I build attention via social products, Twitter, Instagram, TikTok. And I funnel those into different communities, get to know them better, nurture them. And then I build products for those people. And that's my method. It's like, you know, but I think we do it one lane at a time. You know, we, so for example, like when we started Le Checko, we said, we're just going to only focus on the innovation agency. We focus on the innovation agency. got it to a point where it was self-sustaining. And then we kind of like, we're still involved in the business, of course, but we have leadership there that is taking it to the next level that allowed us to focus on the next business. We focused on that. We got to product market fit. Then we slowly, you know, move from a day to day to an advisory and support level. So We do that one step at a time, you know, one at a time. And that's the key, I think, like the key is don't do five things at a time, because then you're just it's so hard to get product market fit that you're just. You. You're you're lowering the probability of basically getting product market fit, so that would be my recommendation to folks.

Tim Stoddart: I thought you said that lowering the probability. I think about, I try my best to think of things in that way. It's like very Buffet monger-esque. It's just, if you look at things in probabilities, then you don't actually have to make the right decision that much. You just like try to continuously make the next highest probability decision. So that's cool that you're thinking that way. I do too. I'm curious, man, you've talked about a bunch of different things and this is a little bit of an off the cuff topic. What is it that you enjoy doing the most? Like you obviously have a skill set and a bunch of different avenues. If you could just chill at home for a week and tinker around on a thing, what is that thing? What do you like doing?

Greg Isenberg: I mean, like a lot of people, I'm always evolving, you know, so my interest changes over time. Like if I, you know, recently, for example, I've gotten into tennis and So like, would it be crazy if we built, like Checkout built, like some media business and community business around tennis? Not crazy at all. I think. You know what I'm into changes over time because I'm learning and I'm I'm I'm following my curiosity. But if you're asking me right now, like I had a week off and I could go tinker, I'd be like, yeah, like what would be You know, I'm very interested in media, media brands, like what kind of media can I build in a few niches that I'm really interested in? And what's an underserved, you know, I'm just using tennis as an example, but like what type of tennis player or tennis even viewer feels like they're underserved right now? And what's something that I can create for them, build media for them that ultimately they start trusting this brand, And then from there I can go and, you know, build some product for them, which is really cool for me because then I'm like, as a person who likes tennis, I'm like, cool. Now I have this like business. It's almost like an excuse to go watch Wimbledon or, you know, go to a certain event. And it makes my life a lot more full.

Tim Stoddart: Do you have a hard time? Actually, I'll make this about me. I. really struggle to shut that part of my brain off. Because it seems like everywhere I look, it's like, Oh, this is a cool community. This is a cool community. This is a cool community. I mean, it could be about anything. I've been a Muay Thai trainer, basically for a long time. And as popular as Muay Thai and martial arts have gotten over the last 10 years, there's still like, very few legitimate, like professional online communities about it. And so Every day, I just can't help it. I'm thinking like, that's an easy one. That's an easy one. That's an easy one. How are you at keeping your brain not running away from you and really like saying no to more things than you say yes to?

Greg Isenberg: I'm actually quite good at saying no to things like my default is no. Yeah. I'm I'm very like, I understand that time is like my number one resource. So I'm always like, I hate when my time is being wasted or I'm spending it the wrong way. So I'm very no, no, no. But in terms of turning off my brain, like at nighttime and stuff like that, it's a constant struggle. I was like taking sleeping pills every night, prescription sleeping pills to fall asleep because I can fall asleep. Ended up finding like that. Ended up finding like now I use something called beam, which is like melatonin plus. Reishi mushrooms and a few other things. that like combine, you know, is all natural and like that, that puts me right to sleep. Um, and, uh, yeah, that's, I need, you know, if, so I need things like that to shut down basically, you know, it's, it's difficult.

Tim Stoddart: Um, four sigmatic mushroom tea is, is definitely my go-to that shit knocks me out. Um, And it's all natural, which, which I really like as well. I think, man, I think you and I have like a whole lot in common. It seems like you're viewing this landscape much in the same way that I am. Um, we're kind of running out of time and I'm going to bring up one last little topic, which could probably be a podcast within itself, but I'm, I'm interested to see your viewpoint about it. This idea about communities. Are you looking at communities as a product within themselves? Are you looking at communities as more just like a brand building mechanism so that people share your ideas for you? I think this word communities has gotten like a lot of buzz around it. Like it's, it's cool all of a sudden to have a community, but it's no different than it always was. Like communities are foundational to who we are as people. I think the difference is now. Software has come around, which make it a whole lot easier. to create paid communities. And so I'm just curious, is that a model that you're playing in with paid communities, or is it more so that just community building will build a brand, an idea, and a business for you?

Greg Isenberg: So it's both. So first of all, I define community-based products as either the community itself is the product, or the community enhances the product. So either you're building a product that the community enhances. So, for example, like the example I like using is Soho House. Like if the membership of Soho House gets poor, not good, like you're going to on your way out, you're going to cancel your membership. But if it's really cool and interesting and you meet high quality people, you know, you might show up more often and get more value out of it. And community is the product could be something like a paid community. So what's cool about paid communities as a business model is. It's got that same. Software as a service like revenue model, monthly membership, but you don't have to build any software. So, for example, I have a paid community I run almost as like. A way to. to meet people interested in building community-based products. I use a platform called Skool to run it. People join it and I just launch it. I have 200 people paying $100 a month, $99 a month. It's bringing in $20,000 a month of revenue. The truth is I'm not doing it for the revenue. We actually pay for it. When you buy When you buy it, you actually get free admin to create, you basically get a free $99 a month school subscription. So we partnered with them. So it's like, I'm not making really any money, but if I wanted to, I could charge $300 and make it. And people would still pay it because they're getting so much value learning on how to build their own community based businesses. And my point here is being, is that I think what you're going to see is a lot more people setting these like memberships. $99, $199, $300, $500. And you're going to start to see them make like $20, $50, $100 grand a month. And all of a sudden you're making a million dollars a year and it's like 98% profit. Yeah. It's crazy. So I think as software has now matured and there's platforms like school and stuff like that, where you can just set it easily, they handle the payments. It's a pretty interesting time to be building paid communities right now.

Tim Stoddart: I agree totally. I think one, when I created Copyblogger Academy, I was in I was surprised on how important the actual software product was. I first built it on. Member press just cause I was a WordPress guy. Didn't really like it. And then I went to mighty networks. I know some people like money networks. I did not like it at all because the landing page is like static. You can't customize your landing pages. Um, so it was like difficult to figure it out, but I landed on circle. I think circle is like really awesome. It's a perfect fit. Schools to school is cool as well. That's the, um, the consulting.com guy. Right. Isn't that, yeah, he went out and built that thing. Um, and man, like it takes a bit, it's kind of like pushing a boulder down a hill because it's hard to get a community going that doesn't have a lot of action on the inside. But then once it's going, you know, the whole thing just takes off and your, your monthly expense never changes. And so like, once you get your nut covered. All of the charges that come through are just all profit. And I think communities are cool as well, because they are like really great. You know, the people inside them love being there. You get conversations going. There's like something to it where you're making money by also providing a thing that everybody is getting a lot of value from. And so I, I totally agree with you. I think it's like a perfect business model for most people.

Greg Isenberg: Yeah. And it's, it's interesting, like in that personal community that I run, like I've run it before and, you know, I've invested in, in, in some of the people, you know, you end up meeting people and investing in them, hiring them. So there's also these. Other benefits besides just like the cashflow from, from paid communities, which is like, you're at the center of the community. And because of that, you get some really interesting opportunities.

Tim Stoddart: Yeah, for sure. A lot of unseen opportunities. Greg, I mean, man, I really loved our conversation. Um, I hope one day you and I can hang out face to face. We can keep shooting the shit about what it is that we're building. Um, what's, what, what's the best place? Just late checkout.studio. I think it is. Right. Did I get that right?

Greg Isenberg: Well, yeah, I guess check out late checkout.studio just as like a website that you might learn from in terms of like developing unexpected websites. You can also check out communityempire.co, which is just a free five-day email course I have around turning strangers into customers using things like audience and community. So if that part of the conversation interested you. And then gregisenberg.com, personal webpage, which I'm putting up tomorrow. And then I'm on Twitter at Greg Eisenberg. I don't know. Fine. You can find me. I'm on the internet.

Tim Stoddart: Yeah.

Greg Isenberg: And I have a podcast too. So check, check my podcast where it happens.

Tim Stoddart: I'll definitely link to that. All of, all of these pages will be linked in the show notes of the episode. You can find the show notes as long as the video and all of the transcripts of the episode on copybloggerpod.com. Thank you so much for listening, Greg. Man, thank you so much for your time. I know you got a lot going on and you took an hour out of your day to come sit here and shoot the shit with me. So I really appreciate it. I hope we can meet in person one day.

Greg Isenberg: Yeah, that was a lot of fun. Thanks, Tim.