In short
Podcast Summary: How He Built A Billion Dollar Network From Scratch | Greg Isenberg
Podcast Information
- Title: Marketing School - Digital Marketing and Online Marketing Tips
- Hosts: Neil Patel and Eric Siu
- Guest: Greg Isenberg, CEO of Late Checkout
- Episode Description: Eric Siu interviews Greg Isenberg about community building, the future of programming, design skills, AI in entrepreneurship, and diversity challenges.
- Listen Here: [Full Interview](https://youtu.be/kdnX63OEP5I)
Key Themes and Insights
- Community-Building Expertise
- Background: Greg Isenberg has been building online communities for 20 years, creating and selling three companies by age 30.
- Community Sizes: He has built communities ranging from dozens to millions, emphasizing that even small communities can be monetized effectively.
- The Importance of Networking
- Building Relationships:
- Greg shares anecdotes from his youth, such as hosting dinners to meet influential individuals.
- He highlights the value of attending events and saying "yes" to opportunities, as they can lead to significant connections and opportunities.
- Entrepreneurship and Innovation
- AI Interests: Greg discusses how his innovation agency connects with large companies to leverage AI in their businesses.
- Business Starting Approach: He often begins new ventures as social media accounts or community platforms (e.g., Twitter, Discord) to gauge interest and build an audience before monetizing.
- Solopreneurship vs. Teamwork
- Team Benefits: Greg argues that solopreneurship can be limiting; having a team distributes responsibilities and leads to better outcomes.
- CEO and GM Hiring: The conversation touches on the challenges of hiring experienced personnel and the importance of finding the right fit to ensure business success.
- Future of Venture Capital
- Changing Landscape: Greg envisions a future where venture capital evolves into a model that combines financing with tangible support, as seen in his agency model that offers strategic resources along with investment.
Detailed Time-Stamps and Discussions
- (00:00) Introduction to Greg Isenberg's community-building experience.
- (06:24) Anecdote about a teenage dinner he hosted to network.
- (10:02) Discusses his experience with StumbleUpon and selling his company.
- (12:19) Insights on AI and its relevance to his work at LCA.
- (14:44) Approach to starting businesses as Twitter accounts/Discord communities.
- (16:49) Discussion on influencer-led agencies and the depth of business focus.
- (18:25) Critique of solopreneurship and benefits of teamwork.
- (20:28) Challenges of hiring CEOs and GMs.
- (22:23) Emphasizes the importance of experience in giving advice.
- (27:26) Greg’s perspective on the future of venture capital, focusing on added value beyond funding.
Conclusion Greg Isenberg's insights provide a comprehensive understanding of how community-building can drive substantial business growth, the importance of networking, and the evolving landscape of entrepreneurship and venture capital. His experiences serve as valuable lessons for anyone interested in digital marketing and community-driven business strategies.
Call to Action
- Subscribe to the Marketing School podcast for daily marketing lessons.
- Follow the hosts on social media for more insights:
- Eric Siu: [X @ericosiu](https://twitter.com/ericosiu)
- Neil Patel: [X @neilpatel](https://twitter.com/neilpatel)
Feedback Listeners are encouraged to provide feedback on topics for future episodes or to leave reviews to help grow the podcast.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:28All right, Marketing School listeners. do enjoy the episode. All right, Greg. How's it going, man? It's going well, man. I like my T-shirt. I like your T-shirt. You know where this is from? This T-shirt is from H-Refs because it's the same. Yeah. That makes sense. Now it all makes sense. Yeah. That's how it works. But yeah, Greg, for those that don't know you, I mean, how would you describe you yourself and what are you known for? I would describe myself as someone who has been building internet communities for the last 20 years. And I started and sold three companies before the age of 30, all using the same community-based approach.
1:13And I have a podcast, so people might know me for my podcast or I read on the internet. Okay. The sizes of the communities that you've helped build, can you give people some context there? Totally. Well, I used to be an advisor to TikTok, Reddit. So those are super big platforms.
1:34And yeah, I've created small communities in the dozens. People think of communities, you can't monetize them, but you actually can. You can have a community of a dozen people and make$12 million a year. Or you can have a community of$120 ,000 and make$120 ,000 a year. So I've built communities with millions of people in it. I've built communities that are a few people in it and everything in between. Yeah, and you're kind of ahead of the curve. I mean, you're in LA. You're at the event that you threw or that you're throwing. I don't know if you did it already, but it was capped out pretty quickly.
2:10You're going up to SF. We're just talking about this pre-show. You're already capped out there too. So you have a knack for doing it. And you moved to Miami around the same time that I did. so that was like where community was like a new community was forming right so if people want to get started with building a community I mean how can they think about it like you do because you have a knack you have a nose for it be a good host you know I think you don't have to in life you don't actually have to overthink a lot of things this is good maybe this is good advice for business it's good advice for anything it's just what is being a good host it's like having the right food, having the right music, having the right amount of people, inviting the right amount of people.
2:53You know, you don't want to go to an event where there's no one there. You want, you know, the right amount of people there. So how do you do that? Oh, maybe you throw a dinner right before so that, you know, so it's just thinking, putting yourself in someone else's shoes is, is what you got to do. Do you have a budget for that? Because I, one thing I love doing is throwing dinners with people that I really respect. So, and I try to cap it at like eight to ten people or so. But for me, usually I like to just pay for the dinner. And just because I found that, like, you know, trying to get it split and everything is kind of a pain in the butt.
3:25So, like, how do you think about it? Are you paying for everything? If so, like, how are you budgeting and all that? I feel like buying these dinners is... It's the best money you could probably spend. So when I was, like, a teenager in early 20s trying to, like, build my network, I would throw dinners all over the world. I was living in Montreal, Canada at the time, but I wanted to bootstrap my network, and I wanted to meet the most successful people I could possibly meet. So what I would do is I'd say, oh, I'm coming to New York, or I'm going to be in LA, or I'm in Paris, and I would throw these little dinners.
4:05And yeah, you want to make it easy on people, so you pay for it. But if you're paying$100 a head, and there's 12 people there, That's$1 ,200. Like, do you think that, of course, you'll be able to monetize that if they're the right people. So I think it's, and by the way, I didn't have the money when I was a teenager to do those things. And I remember one time I was, I won't say who it was, but I was in Paris. I don't know. I must've been 17 years old. And I somehow was able to have drinks with four other people, one of which was an extremely famous entrepreneur. and we get three rounds of drinks and we were at a hotel called Hotel Cost.
4:51I don't know if you know it in Paris. No. Probably one of the nicest hotels in Paris. And you're a teenager? I'm a teenager. What the heck? Yeah. So I take all my money. I go to Paris. I was there for a little web conference in Paris. Yep, yep. And we're having these tequilas. It was a vodka sodas. We're having vodka sodas. And at the end, the bill comes, and it's right in front of me. I'm thinking to myself, I have to pay. I'm not going to be like, I've got to go to the bathroom. It's right there. So I put down my credit card. Bill comes back. It was like 65 euros each cocktail. And we had a lot.
5:35And I just remember thinking, I had that bad feeling in my stomach. right? But you just, if you do these things, you just kind of have to be long-term focused. And I think that's what being a good community person is. It's about being long-term focused. That was every, was that all your money at the time? It was, I was like thinking about how am I going to pay for dinner after this, you know, like, Oh, you're paying for dinner too. Yeah. Okay. Wow. Um, and
6:03yeah, you know, I, I'm glad I did because, uh, there were a lot of situations where I did things like that. I'm not suggesting people get into debt to do this, but I think that these types of things go a long way. So when you're a teenager, what was the context of you setting up that bar meeting, then the dinner? And how did you get in touch with these people? Share more about that. So I was helping build these internet communities at the time. They were finance internet communities. And I was at LeWeb to, this is in mid-2000s. I was there to meet other people. Get out of my hometown, meet the biggest people in the industry.
6:49And I would just go up to people and be like, hey, my name is Greg, I'm working on this. Shoot your shot.
6:58And I met one guy who was with this other well-known person. And I just rolled with it. Like, I just like, you know, they're like, do you want to go for drinks? Like, yes. The answer is yes. Now, did I go up to a bunch of people who turned me down and stuff like that? Absolutely. But I just so happened to be lucky to have met someone who was friends with someone. And that's how it happened. So what I'm hearing is it's one, there's a lot of persistence there, right? Two, you had a lot of thick skin for that age, too. Like you didn't care about the rejections. No. Yeah? No. And what were you trying to get out of it at that point?
7:42Did you even know what you were trying to get out of it? I was just trying to get out of my hometown. Where were you from originally? I'm from Montreal, Canada. Okay. And what I mean, and you know, it's a great city. I don't mean it like literally get out of my hometown. Yeah. But I meant like provide a better situation for myself and gain freedom and gain wealth and create impact. That's what I was trying to do. I remember one dinner that I did. This was like an SF. And there was a bunch of tech marketing leaders there. And eventually that led to a deal with Lyft because one of the people ended up moving over there.
8:21And that led to a deal with Looker, I believe, before they were acquired by Google. You just never know. There's no expectations from it. It's like, oh, yeah, we'd like to get some business from you afterwards. It's just like, no, we're just here to connect great people. And eventually, people come back to you, right? Yeah, and I think you just have to say yes. When you have these opportunities, you want to say yes. So when I was 22 years old, someone invited me to a party at one of the co-founders of PayPal's house in San Francisco. And that party was at 7 p.m. And I was in Montreal at the time, I think.
8:54It was like 8 a.m. and I was like, oh my God, should I go? And I'd look and the flights were crazy expensive and I had a million other things I had to do and stuff like that, but I'm like, you know what? Screw it, I'm going to go. If I book the ticket, you know the expression like buy the ticket, take the ride. That's what I did. And I get there and I get to this house and there was like an indoor swimming pool and it was just so like, it was crazy. I couldn't believe I was there. But I didn't know anyone. I had just randomly got this invite and I'm at the bar and I think I was just ordering like a sparkling water and someone, I went up to the person next to me and I said, you know, what do you do?
9:34Like, tell me about it. And he asked me what I did. And I was showing him this app that I had built and built with my team that I was working on at the time. And he was like, that looks like, kind of like StumbleUpon, which was an old social network, which was sort of like, you know, almost like the for you page TikTok for you page before TikTok do you remember it? It reminds me of Dig a little bit it was OG at the time it was one of the largest social networks at the time so he's like it kind of reminds me of StumbleUpon but for video and I was like yeah that's kind of what we're doing he's like you should meet the CEO of StumbleUpon he's right there so he introduces me to the CEO of StumbleUpon four days later I get an offer to buy my company from StumbleUpon all from that experience I'm assuming you sold I sold that business and it was from taking that plane ticket wow that's such a good example and so did you want to sell at the time I'm assuming they were buying just to prevent a new competitor from sprouting up, right?
10:49At the time, mobile was a question mark. So you had all these, it's I guess similar to how now everyone's thinking about AI. There's like the AI question mark. At the time, there was the mobile question mark. And desktop and web-based companies were kind of thinking about what's my answer to being mobile? And, you know, luck played a role into it. You know, I think we were at the right place at the right time. Got it. Yeah. Makes sense. So what are you excited about right now? Because we talked for your show, you're here for a reason in the West, because you live in Miami right now. But you're a man on a mission.
11:25So let's talk about that. What am I here for? First of all, I believe it's really important to have these doses of inspiration. So I'm a creature of habit. I love staying in Miami. but the action is here in Los Angeles. The action is in New York. The action is in San Francisco. And you got to get out of your house sometimes. So I make it a point, even though I don't really love leaving my city, to go and throw events, meet people, and come back with feeling more motivated and inspired, even though I might be a bit more tired. So that's why I'm here. And I'm particularly interested in talking to people about what are they thinking about how to use AI in their businesses.
12:25We've incubated an innovation agency called LCA where we work with the largest companies in the world to help them build and innovate their businesses. And a lot of people are asking about AI right now. Got it. So do you think that's, I mean, the inspiration goes always, right? Like it could lead to new deals or whatever, but also guides the products that you create as well. Totally. I mean, if you're creative and you want to build the best products you can possibly build, you have to draw inspiration from different places. Because if you draw inspiration from one place only, like let's say you're in this habit, this routine on autopilot, you're checking Twitter, you're checking different newsletters you're subscribed to, podcasts, and you're not like pushing yourself, I'm just not sure that you're going to produce the best possible work.
13:17Yeah, so I think the networking piece is one piece of your learning stack. And obviously you're learning from reading, podcasting, other people's tweets and all that. Are you in any other, like what else is in your learning stack? Are you in other groups? Yeah, I mean group chats. Like I believe group chats is the new social network. Interesting, okay. so yeah there's a bunch of group chats I'm in one with like the My First Million guys and Sahil Bloom and Nick Huber's Sweaty Startup people like that and I get you know inspiration from that I have inspiration from my old high school buddies kind of group chat interesting what inspiration do you get from that one oh just like you know it's a different set of inspiration The inspiration I get is a reminder of...
14:09They all have kids. Yeah, they all have kids, families. And it's also a reminder of where I come from, you know? I think it's a mistake to have just only draw inspiration from one place with one type of person. Because groupthink. Groupthink. Yeah. Yeah. Got it. So let's talk about your businesses. So how is everything structured right now? You have LCA. There's like a bunch. I think you're a boring marketer. Tell us. Yeah, so our thesis is that community-based products outperform non-community-based products. So we start every business as a Twitter account or as a Discord community. And that's our minimum viable product.
14:57So it's literally free, essentially, to start one of these things. And then based, you know, so I'll give you an example. So we started a Twitter account called You Need a Robot about a year ago. And it was just around AI productivity tips. And from that, we created a Discord. And 20 ,000 people joined the Discord to talk about AI. And then from that, we created an agency to help implement automation and AI for companies. We did the same thing with, you know, we started a Twitter account called Boring Marketer to talk about AI-assisted SEO and stuff like that. And then from that, we created a community.
15:45And from that, we created an agency. So that's how we start.
15:53And, yeah, it's going pretty well. We're almost 100 people now. Got it. And you're doing the community to agency thing. I think you've revealed this on Twitter, but like what are the, or X. What are the rough sizes of these businesses? So the Holdco, the Holdco is an eight-figure Holdco. In terms of, you know, profit, I think we'll do mid-seven figures in profit. Okay, great. And you know what's interesting? I mean, this is a great place to go down. So Sahil was sitting in that spot a couple of months ago, And I was saying, I don't think this productized agency thing will work for 99 % of people.
16:31Or sorry, not productized. The influencer-led agencies. Yeah. Right? And so this is good to talk about. Because I know he's using a guy that's operated in the agency space, but he's spinning up agencies every month or so. Right? So what are your thoughts on that? You know, our thoughts are we try to build skyscrapers, not strip malls. A strip mall to me is a bunch of different stores. A skyscraper is you have something that is working and you build on top of it. I'll give you an example. With Boring Marketing, we built a bunch of AI-assisted or AI tech stack basically to implement content creation and SEO-optimized stuff.
17:17Well, that could be spun out as a SaaS business. you know so I'd rather go and focus on building that business than going saying hey we should go build a completely the next one I think it's that's how we see it you're really going deep and then yeah to your point if you do productize it later like you could you know you could scale the revenues pretty significantly and I you know our belief is that we call it multi-preneurship so we believe that the future of entrepreneurship is multi-preneurship, which is this idea around you build multiple products, multiple companies. But we want it. So boring marketing might be its own holding company.
18:03But again, it'll go deep. So I can imagine a world where there's boring ads, boring marketing, but it'll go deep within the boring ecosystem versus creating a completely other company. Got it. Speaking of multi-preneurship, why does solopreneurship not work? I mean, it works for some people if you're looking for a high paying job. Like the best, you know, I think solopreneurship is a trendy word right now. It's, you know, quit your nine to five and become a solopreneur. And for some people, that's cool. Like, you know, I think you, you know, I'm not saying you can't build, you can't build a solopreneurship empire that is doing five or$10 million a year in revenue.
18:47You could. But you're the single point of failure. You have to check the bank accounts, and you have to make sure your taxes are filed. And if the AWS goes down or something happens, you're on the hook. And I think what's cool about having a team, one of the reasons why it's cool, besides just like it's fun to work in a team environment,
19:14is you're sharing that responsibility with others. Sure, you don't have 100 % of the upside, but you're sharing that responsibility.
19:24And so I think there's a few types of solopreneurs. I think there's some people who are creating projects that aren't going, you know, they wouldn't be able to quit their job to do it. That's number one. I think there's some solopreneurs who, you know, cap out around the 100K a year range. And it's a lot of stress. and they basically quit a job to get even a more stressful environment. And then, of course, there's the 1 % or 0.1 % that create an AI app, let's say, that's generating$7 million a year, and it's just them. But I would argue that that's high stress. What I like about multi-preneurship is it's actually low stress because the way it's structured, like our holding company is like we have CEOs and GMs for each of our businesses.
20:13similar to how like a Berkshire Hathaway works or Constellation Software, which is a SaaS software conglomerate. I have some thoughts around that. So the cool thing in like 2020, 2021 was to hire like a CEO or GM. And then I've seen like the office that you're sitting in right now, as a matter of fact, went through the same thing, right? It's like, okay, we hired a lot of experienced people, right, even GMs. Didn't work out, CEO had to step back in. Same thing for me. hired a GM. In fact, tried it a couple of times, didn't work out. And then I had to get really involved. Right. And we've seen the trend happen a couple of times.
20:52And so I like my take on it is like, it probably doesn't work for everybody. I think it works for some people if you get it right. But even right now, like I'm seeing some of the GMs and CEOs being hired. They don't, they've never kind of been there, done that before. And, you know, at the end of the day, even if they're given 10 % or 15%, is that really enough to make them perform at the highest level? So that's been my experience, but it's good to talk about it. I mean, I think it can go both ways. Like I think you can hire a CEO and GM that sucks, and it doesn't work out. And then I think you can hire a CEO and GM that works, and it does work out.
21:33Yeah. I think I've seen both sides of it. So I think you, I mean, the question I think I would have is how do you, if you're trying to hire for that person, like what do you look for? Yeah, I'll give you an example of it working well. So let's use my podcast co-host as an example. It's a nine-figure agency and their template is literally just hiring people from like iProspect. And like these people have been there, his M &A person from iProspect, right? His CEO, iProspect. And then the bigger agency game is like, oh, like, you know, they have a Rolodex of people that they'll recruit with them.
22:12And then they'll have like a book of business too, right? And so it's like a pyramid scheme. But main point is like they've actually been there, done that. I think, you know, I'm very optimistic. Like I want to give people a shot. But I found that like for me, the three or four times that I've done it, it's come back to bite me. But again, it's just one person's experience. Yeah. When I first started my business, the overwhelm was real. I didn't have the tools to help me scale. If only I had Shopify from the start to handle all the behind-the-scenes work. Shopify is the platform behind millions of businesses globally, from huge names like Mattel and Gymshark to the smallest brands just getting started.
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24:27Ready to build a site that looks hand-coded without hiring a developer? Launch your site for free at framer.com and use code MS to get your first month of pro on the house. That's framer.com, promo code MS, framer.com, promo code MS. Rules and restrictions may apply. I mean, I also think that that's what's honestly tough about advice in general. is like what works for you might not work for me what works for me might not work for you everything is so case dependent that's why I only like sharing experience experience sharing exactly you know what I mean for me like the CEO of Boring Marketing for example like I would trust him with anything he sounds like he's been there done that that's true you know like when I look at his writing I'm like yeah he knows what he's doing yeah you can't say that for everyone yeah so yeah I mean the proof is in the pudding I also think there's a lot of like fakers out there yes Yes.
25:18Yes. There's a lot. I don't want to name any names, but yeah. It doesn't matter. We don't need to name names, right? Like the point is there's a bunch of people who say they've done something and they haven't done it. Yeah. And there's a bunch of people who were like, were just around other people who had done stuff, right? So for example, like, you know, just because you were at Facebook in 2006 doesn't mean like you helped grow Facebook to a billion users. Mm-hmm. No, it makes total sense. So, man, well, there's a lot to go down, but I'm just going to focus it on you. Okay, so I'm going to rewind a second because right now you have the main focus, it seems, is you building community-led businesses and it leads into agency.
26:03Like, it's a nice funnel, right? Is that the primary thing? Because you used to do, there's a couple things you were doing before, right? Like you had the, there's the fun, a couple things. So can you walk us through your thinking there on like how you decided to refocus your efforts? Yeah, I mean, we started... So we started late checkout in June 2020. And the idea was, let's create this studio where we incubate ideas. Community-based ideas. And the first idea that we built was this innovation agency. We're just like, companies need innovation. We're going to go and do it. We have this method, this community-based method.
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26:39Cool. Then that started taking off. And then we're like, oh, let's go invest in companies. So we created a fund. And then we started investing in community-based companies. And it's just sort of like, you know, that fund is, like we're still investing. And we're still acquiring businesses too. Like Boring Marketing actually came, I don't think I've really said this anywhere, but like it came out of an acquisition. Interesting. We bought 50 % of a business that became Boring Marketing. And you plugged the CEO in? Yeah. Okay, got it. No, sorry. There was a business that existed, like a seven-figure business.
27:15We bought 50 % of it, and then that business incubated boring marketing. Got it. Yeah. I think that's smart, right? Like you're buying into a business. So you bought 50 % you said? Yeah. Yeah, like I have a friend that he mostly buys businesses at like 33%, right? Because then he doesn't have to operate it. Yeah. And then he just lets them continue to do their thing, and he kind of just coaches them from here and there. here and there, I should say. It kind of sounds like you do the same thing too. You kind of serve as the executive chairman and you go around, hey, what do you need exactly? And you're going around coaching.
27:48Is that what you're doing? Yeah, I think I do that. And I think we'd like to be a bit more involved because we think we want to add value. And also because we have now almost 100 people, designers, engineers, analysts, researchers. We can, let's say with boring marketing, go to them and be like, hey, let's go build your brand. Let's go build a community. we have these people here. So I think that that's a bit of the future of, like people are talking about venture capital is dying right now. And I think the future of venture capital looks a lot more like late checkout than it does Andreessen Horowitz.
28:29What do you mean by that? I know you like a spicy take, so that's why I'm giving it to you. What I mean by that is Andreessen Horowitz, and I don't want to pick on Andreessen Horowitz, but insert big name VC is going to write you a check. And the value is 90 % in the check, let's be real. Versus someone like us, let's say you came to us and you had a business that you wanted to sell or partner, we can actually accelerate that business, not just through financing, but actually through, I mean, we've built some of the biggest communities on the internet, so maybe building a community. Maybe it's, you know, we built some of the biggest ad campaigns.
29:14Maybe it's building ads, optimizing ads, SEO, all that sort of stuff where we work for our equity. And so I guess what I'm trying to say is the future of VC kind of looks more like a mix of venture capital meets private equity meets a studio. Right.

