How He Built a $100M Network In His 20s | Greg Isenberg

So when I was a teenager in early 20s trying to like build my network, I would throw dinners all over the world.

And you were a teenager?

I'm a teenager.

What the heck?

Yeah. And by the way, I didn't have the money when I was a teenager to do those things. And I wanted to meet, you know, the most successful people I could possibly meet.

How did you get in touch with these people?

I would just like go up to people and be like, hey, my name is Greg. I'm working on this. You know, like shoot your shot. I would describe myself as someone who has been building internet communities for the last 20 years.

If people want to get started with building a community, I mean, how can they think about it like you do?

Well, I think I—

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 Ahrefs because it's the same.

Yeah. That makes sense. Now it all makes sense.

Yep, that's how it works. But yeah, Greg, for those that don't know you, I mean, how would you describe 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've started and sold 3 companies before the age of 30, all using the same community-based approach. And I have a podcast, so people might know me from my podcast, or I write 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. And yeah, I've created small communities in the dozens. You know, people think of communities, you know, you can't monetize them, but you can actually, you know, you actually can. You can have a community of a dozen people and make $12 million a year.

Yeah.

Or you can have a community of 120,000 and make $120,000 a year. So I've built millions, you know, communities with millions of people in it. I 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 know, you're in L.A., 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. You're going up to SF. We just talking— 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. You 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 8 to 10 people or so. But, but for me, usually I like to just pay for the dinner. And just because I found it like, you know, trying to get it split and everything is kind of a pain in the butt. So 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, it's, 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.

Hmm.

So what I would do is I'd say, oh, I'm coming to New York, or I'm gonna be in LA, or I'm in Paris, and I would throw these little dinners. And yeah, you wanna 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.

Yeah.

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 have been 17 years old, and I somehow was able to have drinks with 4 other people, one of which was of Extremely famous entrepreneur. And we get 3 rounds of drinks. And we were at a hotel called Hotel Costes. I 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?

Okay. So, I take all my money. I go to Paris. I was there for LeWeb conference in Paris. And we're having these tequilas— uh, it was vodka sodas. We're having vodka sodas. And at the end, the bill comes and it's right in front of me. Of course, I'm like thinking to myself, like, I have to pay, right? I'm not gonna be like, uh, I gotta go to the bathroom.

Yeah.

It's like right there. So I put down my credit card. Bill comes back. It was like €65 each cocktail. And we had a lot. And I just remember thinking, like, 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 gonna pay for dinner after this? You know, like—

Oh, you're paying for dinner too?

Yeah. Okay. Wow. And yeah, you know, I'm glad I did because there were a lot of situations where I did things like that. And 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 were a teenager, what was the context of you setting up that bar meeting, then the dinner? And like, how did you get in touch with these people? Like, share more about that.

So, you know, I was helping build this— these internet communities at the time. They were finance internet communities. And I was at LeWeb to— this is in, you know, mid-2000s. I was there to meet other people, you know, get out of my hometown, meet the biggest people in the industry. And I would just like go up to people and be like, hey, my name is Greg. I'm working on this. You know, like, shoot your shot. And 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.

Yeah.

Um, 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, that's how it happened.

So what I'm hearing is it's one, there's a lot of persistence there, right? 2, you have 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? Did you even know what you're trying to get out of it?

I was just trying to get out of my hometown.

Where are 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, you know, gain freedom and gain wealth and create impact. Yeah, that's what I was trying to do.

I remember one dinner that I did. This was like in SF and That from that, it was like a bunch of like tech marketing leaders there. And eventually that led to a deal with Lyft because one of the people ended up moving over there and that led to like a deal with Looker, I believe, before they were acquired by Google. You just never know. Like there's no expectations from it. It's like, no. Oh yeah. You know, 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, you have to say yes. You know, 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 7:00 PM. And I was in Montreal at the time. I think it was like 8:00 AM. And I was like, oh my God, should I go? And I 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.

Yeah.

So I booked 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 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, I said, what do you do? Like, 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's kind of like a little after. It reminds me of Digg a little bit.

Yes.

You know, so yeah.

It was OG. You know, at the time it was You know, one of the largest social networks at the time. So he's like, 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. 4 days later, I get an offer to buy my company from StumbleUpon.

Wow.

All from that experience.

I'm assuming you sold.

I sold. Yeah, we sold, you know, but yeah, I sold that business.

Yeah.

And it was from taking that plane ticket.

Yeah. Wow. That's such a good example. And so the— did you, did you want to sell at the time? Like, I mean, like, I'm assuming they were buying just to like prevent a new competitor from sprouting up, right? Like—

At 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 like we just— we talked pre-show, like you're here for a reason nonetheless, because you live in Miami right now. Yeah, but you're a man on a mission. So 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.

Mm-hmm.

So, that's why I'm here, and I'm particularly interested in talking to people about What, what are they thinking about how to use AI in their businesses? Yeah, we've, we've incubated an innovation agency called LCA where we work with the largest companies in the world to help them, you know, build and innovate their businesses. And a lot of people are asking about AI right now. Got it. Yeah.

So do you think that 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. Yeah. I mean, If you want to be— 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, you know, 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.

Yeah. So I think, look, you're— well, I think the networking piece is one piece of your learning stack.

Yeah.

And obviously you're learning from reading, podcasting, you know, 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, I'm in 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. You know, I'm in one with like the My First Million guys and Sahil Bloom and Nick Huber, Sweaty Startup, people like that. Um, and I get, you know, inspiration from that. I have inspiration from my old high school buddies kind of group chat.

Interesting.

Yeah.

What inspiration do you get from that one?

Oh, just like, you know, it's a different— it's a different set of inspiration. Uh, the inspiration I get is a reminder of—

They 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, your businesses. So how is, how is everything structured right now? You have LCA. There's like a bunch of— you have, I think you have 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. So, it's literally free essentially to start one of these things. And then based— so, I'll give you an example.

Okay.

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 and from that we created an agency. So that's how we start. And yeah, it's, it's going pretty well. We're almost 100 people now.

And you're— so you're doing the community agency thing. I think you've revealed this on Twitter, but like, what are the— or X. Yeah.

What are the rough sizes of these businesses? So the holdco, the holdco will do— is an 8-figure holdco. In terms of, you know, profit, I think we'll do mid-7 figures in profit.

Okay, great. And you know what's interesting? I mean, this is a great place to go then, because Sahil was sitting in that spot a couple of months ago, and I was like saying, I don't think this productized agency thing will work for like 99% of people. Or sorry, not productize the influencer-led agencies. Yeah, right. And so this is good to talk about because I know he's using a guy that's, that's operated in the agency space, but he's spinning up agencies like 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. Strip mall to me is, you know, a bunch of different stores. A skyscraper is you have something that working and you build on top of it. So, I'll give you an example. So, with Boring Marketing, we built a bunch of AI-assisted or AI tech stack basically to implement content creation and SEO-optimized stuff. Well, that could be spun out as a SaaS business. So, I'd rather go and focus on building that business than going and saying, hey, we should go build a Completely other.

The next one.

Yeah, exactly. Yeah, yeah. I think it's— that's how we see it.

Yeah. So 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.

Exactly. And, and I, you know, our belief is that we call it multipreneurship. So we believe that the future of entrepreneurship is multipreneurship, which is this idea around You build multiple products, multiple companies, and we— but we want to— so Boring Marketing might be its own holding company, but 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.

Yeah.

Speaking of multipreneurship, why does solopreneurship not work?

I mean, it works for some people if you're looking for a high-paying job. I think solopreneurship is a trendy word right now. It's quit your 9-to-5 and become a solopreneur. And for some people, that's cool. I'm not saying you can't build a solopreneurship empire that is doing $5 or $10 million a year in revenue. You could, but you're the single point of failure. You have to check the bank accounts and you have to check, make sure your taxes are filed. And if the AWS goes down or something happens, you're on the hook.

Mm-hmm.

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, is is you're sharing that responsibility with others. Sure, you don't have 100% of the upside, but you're sharing that responsibility. And so, I think there's a few types of solopreneurs. I think there's some people who creating projects that aren't going— they wouldn't be able to quit their job to do it. That's number one.

Mm-hmm.

I think there's some solopreneurs who 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.

Yeah.

What I like about multipreneurship 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, similar to how like a Berkshire Hathaway works or Constellation Software, which is a SaaS software conglomerate.

I have some thoughts around that. So the, 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. And 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— I mean, that's been my experience. So, 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. Yeah, 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 9-figure agency. And their template is literally just hiring people from like iProspect.

Right.

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 and 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 3 or 4 times that I've done it, it's come back to bite me. But again, it's just one person's experience.

Yeah.

Yeah.

I mean, I also think that that's what's tough. That's what's honestly tough about advice in general.

Yeah.

It's 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. Like, 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, there's a lot. I don't, I don't want to name any names, but like, 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, we're 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.

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. Like it's a nice funnel, right? Is that the primary thing? Because you used to do— there's a couple of things you were doing before, right? Like you had the— there's the fund, a couple of 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. Cool. 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, that fund is like, we're still investing.

Mm-hmm.

And we're still acquiring businesses too. Yeah. 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 7-figure business. We bought 50% of it and then that business incubated Boring Marketing. Got it. Yeah.

So I think that's smart, right? Like you're buying into a business So you bought 50%, you said? Yeah. Like, I have a, I have a friend that he mostly buys businesses at like 33%, right? Just because then he doesn't have to operate it. Yeah. And then like 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. Like you kind of serve as the executive chairman and you go around, hey, what do you need exactly? And you're going around coaching. Is that what you're doing?

Yeah. Yeah, I think I do that. And I think we'd like to be a bit more involved because because we think we can, you know, we want to add value. And also because we have now, you know, almost 100 people, designers, engineers, analysts, researchers, we can, you know, let's say with Boring Marketing, go to them and be like, hey, like, let's go build your brand. Let's go build a community. We have these people here.

Yeah.

So I think that that's a bit of the future of like people, 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.

What 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've built some of the biggest ad campaigns, maybe 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. That makes a lot of sense. And so, I mean, the community aspect, that's a huge selling point, right? The private equity aspect is like you guys have like a You know, main office and all that. And then, you know, obviously you have the money. I'm curious, like, your— how does your day-to-day look? Like, let's say on a Monday or Tuesday, like, is it like— because my friend, for example, he's got a similar type of setup where it's like there's a bunch of— well, I won't say what type of business because that reveals who he is. But he will look at a scorecard for all the businesses on like a Monday. And whatever is not doing well, then he'll just hit them up and be like, hey, like, let's have a conversation, right? But there's no like set schedule or anything, but he's just kind of playing free safety and looking around to see where he needs to jump in. How do you look at it?

I don't do it like that. So, and I don't do it like that because I feel like if someone needs me, they're going to reach out to me and I don't want to be like, hey, I see that.

You don't want to hover?

Yeah, I don't want to hover. It's not like That's lame. And it doesn't feel good for me either. I want people to feel, and they should feel like they're driving the businesses. And if they have a question, hopefully they— and they want my feedback, hopefully they'll reach out. I focus on new bets. What are new areas that I think that we could be investing in, double-downing in? What are companies we should be buying? How do we reach out to those founders and connect with them? Should we fly them out to Miami and, you know, have a crazy dinner? And, and like, I'm just thinking about how do I grow the business? That's what, that's what I'm thinking about. And then that's part like business development, these deals, and then part like products.

Yeah.

What are the products and communities that we need to be building and what does that look like? And that's like sketching it out and getting into Figma and pushing pixels.

So when you wake up, it's the main question is how do I grow this thing? Right. And then you just will look around and if you have an idea, if inspiration hits, then it's like, okay, you're going to have that conversation.

Correct.

Okay. Yeah, got it. And I think everyone should know too, like you have a— correct me if I'm wrong, your background mainly comes from design, right?

Yeah. Although I did go to school for computer science, I'm a traditionally trained computer science person.

Yeah.

Yeah.

Well, yeah. So you got both there.

Yeah.

Which is interesting too, because you think about growth and so you could argue that you have a marketing mind too.

Yeah.

Yeah.

I mean, if I was starting off right now, I would, I would try to teach myself design, marketing, and engineering and get good at all those 3.

Yeah.

Because that makes you deadly.

This message is brought to you by Leveling Up Founders. And Leveling Up Founders is an invite-only event for founders. It happens once a year, usually during August. And past attendees include people such as Ali Abdaal, Cody Sanchez, Neil Patel, Vanessa Lau, and the list goes on and on. And ultimately it comes down to the quality of the group of the people. We try to keep the group high caliber. That's why it's invite only. So if you are a founder at the top of your game, you can go to levelingup.com/founders to learn more about it. And you can apply and we'll see you on the other side. Well, speaking of Deadly, I want to go back to the community thing. How, like if someone wants to start a community from scratch because you've helped The TikToks of the world, the Reddits of the world. Did you say Reddit?

Yeah.

Okay. So biggest communities in the world. How do people get started? Like you just mentioned offhand, you're like, yeah, you know, we just started this community, 20,000 people, right? So like people are like, how do you do that?

I use a framework called the ACP funnel— audience, community, product. So I'm not— I don't start a community first. I always start with the audience. Now, there's a difference between a community and an audience. People will call an Instagram page a community when it's an audience. People call a TikTok page a community, it's an audience. An audience, generally, the way to think about it is— the way I think about it is, how do I create a category of one? No one was talking about boring marketing. before we created boringmarketing.com. People were talking about boring businesses. That was a trend that was coming up. So it's trying to think, how can you own a word? And owning a word is really important to me. I think—

who wrote that? Who wrote that book? Christopher Lockhead. Remember that book?

What was it called?

I'll find it. You go ahead.

So I try to, I try to figure out how can I own a word and, and focus on a particular niche.

Mm-hmm.

People into SEO, people interested in AI and productivity, whatever. Once I've built, let's say, 10,000 followers in that niche, I try to think about what are the different rituals and programming that I can create such that an enclosed community of these people will be a really interesting, almost lead magnet, right? Because what you don't want to have is you build a big audience on TikTok and/or Twitter, Instagram, and then the algorithm changes, and then all of a sudden you have to start from scratch. So your goal then becomes, how do I convert some percentage of these people into an enclosed community where you get their phone number or their email address, and also you turn them into a raving fan. So how did I create, you know, a Discord, let's say, with 20,000 people? Was, well, I built a Twitter audience at the time of like 35,000, and I converted a lot of those people into this free community. And I understood the different events and programming that these people really wanted.

Right. And when you get people in, it's not just, okay, you're done. No, the work actually starts.

The work actually starts. Yeah. Yeah. And I think that's why 95% of communities are— 95% of digital communities are zombies.

I'm not gonna lie. I've created a lot of those. Yeah. Yeah. It's like there's like a burst of energy from me for like a week or two.

Yeah.

It's just like, so how do you keep it going?

Well, I think I, I know that you— the ritual, the rituals is the biggest part. You know, what are the things that you are gonna create within this community such that people come back. And I use the word ritual because a ritual is almost like a religious term. It is a religious term. And I try to almost make the experience like a religious experience.

So what are some of those rituals?

I mean, oh, well, I'll tell you. Sorry, I was just gonna go on a tangent around— Like, I think every great community is similar to like a religion. Like, if you think about religion, you know, you have the Bible, which is, you know, a textbook of all like the stories of a particular culture, things to do, things not to do. There's short-term goals, there's long-term goals. You know, long-term goal might be go to heaven. Short-term goal.

Don't go to hell.

Yeah, exactly. You know, these are the things, right? Like, what is religion? Religion is basically this incredible way of bringing community to people and for them to act, act like good people.

It's a good operating system.

It's a good operating system. If you want to build a community that sticks, you need an operating system. And you have to take it seriously. So, like, you know, there's a reason why a lot of people go to church every Sunday. What is, you know, what is the equivalent of your church on Sunday?

Right.

And each community will have a different thing. Someone— I was just meeting with someone right before this, and he was like, he showed me a graph that apparently, like, half of Gen Z doesn't believe in religion anymore. Have you seen this?

I've seen it. There's been an uptick in talk about this in the last week. Like Joe Rogan's like, we need Jesus, you know what I mean? So it's like, I get what you're saying. Continue. I do think it's probably a good thing for most people because most— there's like when you don't have direction, you just start doing all kinds of stupid stuff. So.

Well, first I'll say that, though, you know, those 50% is your market. The people that are looking for connection, that feel disconnected, that are looking for ways to connect, be a part of something bigger than themselves. Yeah, that's a huge opportunity for, for you to build a product or service that brings people together. Yeah. A community-based product.

Yeah. So like what— and I think I've DM'd you about this before, like where can— well, okay, before I even ask that question, what are some examples of some of those rituals?

Right?

It's like, oh yeah, we're going to meet every Wednesday and we're going to do like a live Q&A. Like that's an example. I'm sure you got some better ones than that.

Yeah. I mean, you know, I'll give you one example, you know, a few examples. Well, you know, we have a private, you know, we can talk about this, a membership. You know, we like to say that memberships is the new internet community.

Yes. Let's talk about that.

And we have this membership called Community Empire.

You can shill one of my investments.

Oh yeah? Yeah. Shill away, man.

No, but I believe it.

Is it?

Well, no, I mean, you shilled it.

Oh, perfect.

Continue.

Um, I'm not even meaning to shill, you know. I just, I actually believe that, um, oh yeah, going back to membership, right? So Community Empire, and you know, one thing we'll do is this like punch you, we have a punch you in the face meeting. And it stems from a meeting I used to have with a friend of mine, Julian Smith, New York Times bestselling author, where we'd meet every Monday at 7:00 AM in the cold, like we were living in Canada.

Wow.

And he would say, what did you do last week? And we would hold ourselves accountable. I would say, what did you do last week? We'd try to make sure we hit our goals. So that's an example of a goal-setting meeting that would be helpful for a community of people building internet businesses or membership of people building internet businesses. So I think that one of the reasons why people fail in terms of building internet communities or memberships is they make it all about the leader and not enough about the peer-to-peer.

Right.

You're in YPO, aren't you?

Mm-hmm.

Tell me about that community experience.

It's interesting. So like the main, the main thing you value in EO or YPO is like your forum, like the 10 of people, the 10 people that are your brothers and sisters. And this is the stuff that you share everything with, right? Like these are— this is like the 5% of things that you can't share with your spouse or your friends. You share it with this group and it goes really deep. A lot of experience sharing. And ultimately, I believe a huge amount of the value from YPO and EO is actually just the forum. And then, yeah, they have events around the world and all that. But it's to get high performers together. Like, that's the community.

Yeah. So yeah, and I think I'm not a part of either of those communities, but I think—

Come on in. The guy that has this office, he's YPO, and then there's a YC poster over there. So he came out of YC. Yeah. So you can have multiple communities, you know?

Yeah, totally. And I think like those are both examples of great communities. Like, I'm looking at the YC poster there. Just make something people want. And the YC logo, like, chef's kiss in terms of like, how do you get people to feel connected to a mission bigger than themselves?

Yeah, that's so well said right there. That is the premise of YC. But it's like, you know, the way I think about community— you play any games growing up?

Counter-Strike.

Yeah, it's like clans and guilds, you know what I mean? And like, When we were in high school, like, that's what we thought about. Like, we wanted to go back and like get with our clan because like we felt valued.

Well, that's how I, that's how I got into this internet community stuff to begin with.

Yeah. So you were like on IRC back in the day?

Yeah.

Okay. Same here. The, all the forums, right? Yeah. Yeah.

I was like, okay, what makes this clan better than that clan? Like each clan had like a brand associated with it and they had like little websites and like, you know, who managed their IRCs, which are these like essentially pre-Discord Discord.

Pre-Slack.

Pre-Slack.

Yeah.

Yeah. Yeah. I just realized like how powerful, how powerful community is, right?

I mean, obviously, I think, you know, you as the leader of the community, you starting it out, there's going to be a nice push.

Yeah.

But you can't manage it forever, right? So the question I asked you back in the day was like, where the hell do you go to hire amazing community managers, right? And the thing is, like, even when I was going through this Web3 phase that we're both going through, like, I was just like, These Web3 community managers are just getting destroyed. Like, I can see they're like— and I don't use the phrase mental health much, but I can see their mental health like deteriorating. Yeah. So that's a whole nother thing. But first, where do you go to hire amazing community managers?

So this is a controversial, controversial take within the community management space, what I'm about to say, which is you hire within the community, you find— you find people who are super active within your community that are just inherently, organically doing a good job at being engaged. And you say, hey, I know you're a dentist, or I know you're a marketing manager at Coca-Cola, but would you be willing to join as the marketing— as the community manager at Y Combinator?

Yeah.

Those are the best people because they understand your mission. That's what people don't get about internet communities is They'll spend like a year trying to like build an internet community, but they don't have the right mission. The mission doesn't— is not potent enough.

How do you— how do you pay these people?

How do you pay a community manager?

Yeah, because, okay, dude, and like a lot of these like Discord Web3 managers were getting paid like $10, $15 an hour. I'm like, how do you survive?

Yeah, so, well, I think a good community manager is worth his weight in gold. You know, we—

they kind of are the product a little bit.

They are. Yeah. You know, we have a community manager. I even feel weird calling him a community manager because he feels like—

What do you call him?

I think he's head of community of Community Empire. And he— like, I just jumped in a Twitter Space with him like earlier today and he just— he cares so deeply about every single person who comes into the community and he has like an onboarding call with every single one and he's thinking about them 24/7.

Unprompted.

Unprompted.

Wow. You know, just doing it right.

When you find people like that, you got to hold on to them.

Okay.

Yeah.

So how much should a head of community be paid?

Oh, I mean, at least whatever you're going to pay like a marketing manager or social media manager, like 30 to 50% more than that.

Yours sounds pretty experienced and I'd say that's probably like anywhere $150-ish, $200.

I mean, yeah, I think you can expect to pay a lead community person 6 figures.

Yeah.

Yeah.

Got it. Makes sense. Yeah. And I think that's a, that's a good tip because like there's, I think there's— did you start— what was that? There's a community SaaS app. Do you know what I'm talking about? Comm, C-O-M-M or something?

C-O-M-M? No.

I don't remember, but they had like these forums and everything and there's like a— there's another guy that had like a— he was known, he wrote a book about community and it just— it's still incredibly hard to find people from those boards and those forums.

Yeah.

So I do agree. I feel like what you're really saying is, you can correct me if I'm wrong, you as the founder or founders, you're going to start it up, you're going to get it going, and then eventually once you have a couple of people, Just find from within.

Exactly.

Yeah. And do you find it pretty— the ones that are most active, from like a recruiting standpoint, it sounds like they're way more likely to convert because they're already bought in.

They're bought in. Yeah, they, they're excited to talk to you.

That's like a recruiting hack, actually. Like if you can build a community of the best marketers, just try to pick them off because they already know who you are. They know, like, and trust you.

I mean, 90% of the people who work at Lake Checkout are like in our communities or follow.

That's a hack. Yeah, that's a good hack. That's a great recruiting hack. Everyone should build a community. So that's cool. Well, okay, let's move up a level or a couple levels. Where do you go to hire CEOs and GMs? What's the Greg Eisenberg way?

It's one of the reasons why I'm here. You know, like, I feel like you need to— I mean, if you're going to hire a CEO or a GM, that's a partner.

Mm-hmm.

And if you want to find a partner, it's difficult just to do it through the DMs. You want to like break bread. You want to, you know, you're marrying this person. So that's how I take it really seriously. And that's because like, I don't want it to end prematurely. I don't want to, you know, have someone quit their job and then it doesn't work out with us, you know? I want to ensure this works. So, how I find them is generally I reach out to people on the internet. I literally cold DM people that I find interesting. Like for example, I was just tweeting with this guy Cody Schneider. Do you know him?

I've seen that name.

Yeah.

C-O-D-Y?

Yeah.

Yeah.

He— I don't know him. Never spoken to him. Just, I follow him on Twitter and I think he's funny. Funny and interesting.

Yeah.

And he, you know, my business partner tweeted out, oh, we're going to— me and Greg are going to SF, you know, who should we meet? And Cody responded and he's like, he's out of town. He's like, you know, on the mountains in powder, deep in powder in Colorado. And That's like a guy who I was like, damn, like, I really want to hang out with you, you know. I guess in my head, what I'm trying to say is in my head, I have this like shortlist of people who I find really interesting from the content that they create. Yeah, even if it's just once a week or once every 2 weeks. And going back to like shooting your shot and not being afraid, I just reach out to people all the time.

I mean, it's like the Getting Things Done dude, David Allen. It's just like, You know, just take— if anything takes less than 2 minutes, just go ahead and do it. Like, a DM takes you like less than 30 seconds.

It's also free.

Yeah.

Like, DMs are free.

Yeah.

Like, what are you doing? Like, what are you listening to this right now when you could be DMing someone?

Yeah, you should pause this and go DM someone right now.

And it's not— don't do like a—

Creepy DM?

Creepy DM, or don't do like, you know, there's also an art to writing a good DM.

Yeah, tell us that art. What's the art to writing a good DM? That gets you millions of dollars?

Record a video. It's not text. Why? Because text is what everyone else does. You record a 30, 60-second video and you tell a story.

Like a Loom.

You write a Loom.

Yeah.

You do a Loom.

Dude, back in the day there was no Loom available and it was really hard to find emails. You had to use data.com and I would spend like 20 to 30 minutes making each video. But eventually I was like 24 or 25 at the time, but eventually that led to a deal where they were paying us like $30,000 to $40,000 a month just because one of the videos hit. And so like nowadays there's no excuse. Loom, you just download the extension, do it 30 to 60 seconds, give some good insights and you're good.

That's it. Yeah. And I'm surprised more people don't do it.

Yeah. Well, most people want to win, but they don't want to put in the effort.

So, and they're afraid of What if they don't respond?

Yeah.

Um, I got to meet 2 of my heroes last, last year, 2023, just by DMing them on Twitter.

Can you reveal those heroes?

Well, one, I'll reveal one of them. Yeah. And this one is gonna sound like lame.

Okay, we'll see.

Maybe.

Go for it.

But you know the Virgil Abloh quote? I think he says like, Something around how do you make your 16-year-old self proud? Something like that.

I didn't know it was from him, but yeah.

This would make my, like, 16-year-old self proud. So Rivers Cuomo from the band Weezer. Oh, okay.

Yeah.

I just— I tweeted something. I think I said the, the internet used to be an escape from reality. But now reality is an escape from the internet.

Yeah, I remember that. That's a good one.

And all of a sudden, I see Rivers Cuomo likes the tweet. And you have like 1 second. You have like 10 seconds. So I saw he liked it, sent him a DM right away. And I said something like, big fan. You know, I should have done a video, but I knew I had like a few seconds. Yeah, big fan. Uh, would, you know, would love to meet up sometime if you're in Miami. He goes, I'm actually gonna be in Tampa in a few weeks if you're ever around there. Book a flight. For, you know, all of a sudden I'm hanging out with one of my heroes backstage.

That's awesome.

He invited me backstage. I had a backstage pass, hung out with him, had a really great conversation. And felt inspired from it.

Did you do dinner with him as well or anything like that?

No, it's just, just—

Just a hangout?

Just, we hung out.

That's cool.

And he's like my friend now. We text. Yeah, you know, it's like crazy.

What, so what do you guys text? I mean, this is your childhood hero. Like, I remember, you know, I remember listening to Weezer. So like, what do you guys talk about?

Rivers is actually You know, from my conversation with him, like, he's kind of like a nerdy type guy. And he's really interested in like bots and AI and, and because he's a musician and, you know, he actually ran a Discord, like, he likes community too. Yeah. So he's not just, you know, these people aren't just 2D, like, they're 3D. They have a bunch of different—

Well, you guys have things in common.

We have things in common.

Yeah.

Yeah.

It's not— yeah, it's, uh, and like you guys are able to get something from each other.

That's right.

And like no matter what people say, we are looking to get something from each other.

That's true. There is some transaction in that sense.

Yeah, got it. But let me back up a second. So, um, how good were you at Counter-Strike on a scale of 1 to 10?

8.

8? Okay. There was a guy sitting in your spot a couple weeks ago, and then we're just talking about Counter-Strike, like some elite clans. He's like— I was like, You know, there's this clan called Skilled in Killing, right? It was like one of the top Kalai clans. He's like, I was in Skilled in Killing. I was like, what the? And so, but like my point of saying all this is like the gaming, like if you're good at gaming, it translates over into entrepreneurship. Like even the community building piece.

Totally. So yeah, I think I was like Cal M and Cal P.

I was Cal M. Yeah.

Yeah.

Yeah.

So we were like pretty good.

We're pretty good. We weren't like top, you know what I mean? No. What was Cal P?

Cal Premier.

Oh, okay. All I know is Cal M. So Well, let me— let's go back to the CEOs and GMs. So what do you look for in the CEOs and GMs? Because it seems to be working for you. I just don't think it works for like a lot of the people tweeting about it. So yeah.

Maybe because a lot of them are in a rush and I'm not in a rush.

Yeah, you seem just chill.

You know, what's the expression? Slow is steady and— or slow is smooth and smooth is fast. Is that what it is?

And you also got to go slow to go fast.

Something like that. Yeah, I don't know. All I know is that whenever I focus on short-term, instant gratification type things, the more it hurts me. And the longer— the more I think about long-term, doing things in the long-term, and look out into the distance instead of looking right in front of my face, the more things seem to go my way. So, What I look for in a CEO or a GM or a partner really is someone that I could trust with a bank account, someone who I will never have to hover over, someone who doesn't need to have all the answers, but could is good at, like, finding answers, very resourceful. And often these people are not Stanford people, they're not Harvard people, they didn't grow up in New York, they didn't grow up in San Francisco. They're kind of like similar to me in the sense they're, you know, I grew up in a French-speaking town, like a bit different, you know, or a small town, or like just something— someone who has something to prove.

Yeah. Chip on the shoulder.

Chip on your shoulder.

Got it.

Yeah.

How do you— okay, so when you think about your— all the CEOs and GMs that you have, what percent of them have actually been there, done that?

Probably like half.

Okay.

Yeah.

And so now you, you break it down, like, does that half— does that cohort perform meaningfully better?

The people who've been there, done that perform better than the people who don't. Like, I think going forward, like, I'd rather essentially pay up for the people who've done it. Yeah, that's the lesson, right? Like, the lesson is like, if you've done it once, you probably could do it before. You probably can do it again.

Dude, if you did a case study on that, I think it would be fascinating. It's like people have been there, done that, like perform X% better. Yeah, I will download that. And so you just kind of brought it up, but how do you think about structuring comp? You don't need to give exact numbers, But like typically, how would you structure the base and then equity and all that? If you even give equity?

I mean, it depends like the person, like, and how much experience they have. Like if you— and also the stage of the business.

Let's say it's like, you know, 7-figure business, does a couple hundred grand in profit, you know, 10, 15 employees or something?

I think—

I'm assuming this is like a smaller business for you. Yeah.

I think like the general philosophy I have is if I'm eating, everyone should eat just as much, if not more, right? So, like I want the person who's driving to feel that they're getting that they're getting the good end of the stick. And that depends depending on who that person is. But I think that like if you have a business making a few million dollars a year, like, great, like, go— like, I want you to make half a million, $1 million.

Mm-hmm.

You know what I mean? Like, that's great. But if the business is making a couple hundred thousand dollars, like, you know, or $500,000, like, okay, it's fine to like break even for some amount of time, but We're— we are focused on building profitable companies because we don't— we've never raised venture capital.

Got it.

Yeah.

In general, though, how do you structure like equity? Are you doing 10%, 20%?

Yeah. I mean, like—

They're not having to buy in, right?

Yeah. No. Like, as an example, just like Boring Marketing. Yeah. Like Boring— the Boring Marketing team owns 50%. And that is Like the CEO basically, you know, decides how much.

That's very nice.

Yeah.

Yeah.

And, you know, one of my team members was like, that's, that's a lot. Like, why are we doing that? You know? And I was like, no, no, no. Like, this is like, yeah, could we, could it have been 30%? Yeah. But, you know, I think one of the reasons why it's winning is because of How much that team is incentivized.

That is— I would love to continue to see the progress of that. I think that's an amazing case study. So 50% is for the CEO plus the employees or just the employee share?

CEO and the employees.

Okay. And then the other 50% is you?

Yeah.

That's great.

Oh, no, sorry. No, no. So I'll explain how it actually works. And this might be interesting to people, actually. Late Checkout's the holding company. If you work at Late Checkout, you get a share of the profits. No equity, a share of the profits. If Boring Marketing, for example, sold, it's a separate company. Those profits— and I don't know if this is like too technical.

No, this is great.

Yeah, I love this stuff. That profit flows to Late Checkout. Every 6 months we give a profit share. that particular 6 months, let's say we sold it for $50 million, would be a very good month— or sorry, would be a very good 6 months, and then we distribute that to our team. Now, if you work on specific companies, some of those companies will give equity away too. And the CEO decides how much of that equity they want to give.

Mm-hmm.

So for example, with boring marketing. Late Checkout owns 50%, which basically means the whole team, the 100, you know, the teammates get a profit share based on their seniority and how much they contributed to the project. Like, are they involved in it or not? And the direct team as well.

Got it.

And so that you have the— so you have 50% equity Plus you have this profit share. Yeah.

Oh, cool. So it's like you get to double dip.

You double dip.

Yeah.

Yeah.

I'm imagining you haven't shared— this sounds like a pretty sophisticated model, but it sounds like it works too.

And I don't know, you know, holding companies like internet-based holding companies are relatively new. I mean, people have been doing it for years, but not at this scale. The amount of holding companies that have been created in the last 12 or 18 months, probably as many as have been created in the last 10 years in internet, in our internet world.

It's like the cool thing now.

Yeah. So I think like we're still figuring it out, frankly. We're still figuring it out. But I will say like it feels like our team, you know, feels excited. And I also think that, you know, I sold my last company to WeWork. WeWork is the greatest example, or one of the greatest examples of venture capital going wrong.

Worked out for the founder.

You know, what'd they raise, like $22 billion? Something like that. Something like that. And I remember meeting people right before we were going to go public at WeWork, and people were like, yeah, next month when we go public, I can't wait to buy this house in Laguna Beach and renovate my house. Or retire my parents or— so I think a lot of people got burnt by getting equity in venture-backed startups that now working at some, like a place like ours where it's like, hey, you're gonna, you're gonna get a profit share.

Yeah.

Like, that's pretty cool. You're, you're, you know, like you're gonna get a check every 6 months versus, hey, go wait 12 years and maybe in 12 years your equity is gonna be worth something. If all these things align, like the market is right or the company didn't raise too much money or etc., etc.

It's how the media used to market this equity, right? It's like, oh, like if you, you know, were at Microsoft or Google, you were making millions of dollars. And so everyone automatically thinks, oh, that's what's going to happen, right? But that's not the reality versus like, oh no, you're actually going to get like a check. Yeah, every— yeah, that's like way more tangible. Yeah, right. Your profit sharing, is it like, is it like a 10% pool, 20% pool?

I honestly don't know.

Okay.

Yeah. Got it.

Yeah, because usually when I think about all my founder buddies, it's usually like 10 to 20% or so. So just trying to confirm.

Yeah, it's like in that ballpark.

Got it.

Yeah, cool.

By the way, Neil and I have an agency owners group called the Agency Owners Association. All you have to do, just go to marketingschool.io/agency. Once again, it's marketingschool.io/agency. To learn more. And now back to the show. Now I want to— let's go back to the memberships thing, because when you talk about the new internet community, the thing you shilled, which I thank you for shilling, is Skool. So, like, is your new community built on Skool?

Yeah, we've been actually building on— we have like a ton of Skool communities. We've been building on Skool for the last maybe 18 months. So for a long time.

Why do you like Skool?

Why do I like it? And I've used everything, right?

It's cheap.

It is cheap.

Yeah.

So, but that's not why.

Yeah.

So, you know, here's why I like it. The gamification is good. Like the fact that you can set it up such that if you do these things, you unlock certain content or rituals, for example, like maybe you get, you know, one-on-one calls or access to certain events. I think having just gamification that unlocks certain things, like the more active you are, the more things get unlocked to you, and turning your community from a community into more of a game. Yeah.

Yes.

Is really, really powerful. Like when I look at Community Empire, like I think it's 90. Yeah, 90% of our community is active weekly.

That's high.

Wow.

If you're any SaaS app, it's like, that's amazing retention.

Yeah, I was going to take my phone. I don't have my phone on me, but I would like— I would show you the receipts. Like, it's—

Yeah, sure.

Yeah.

We're grabbing his phone right now. That's the pause.

My IBM jacket.

Oh, that's old school. Did you get that on eBay?

Got it in Tokyo.

Nice.

All right, school.

I just think the more things we gamify, the better. Like, why did we play so much games growing up, you know?

Totally. I mean, that's probably why we like it, right? Yeah, because we know the power of games.

Business is the ultimate game, and it just never stops.

Let's see, metrics. This is honestly like, I can't even believe this. So in the past 30 days, your group grew to 334 members. Cool. And 329 members, 99%, were active. I actually can't believe this.

Wow. Look, it went up. It went up.

The graph keeps upward going up.

Yeah, that's crazy. So what kind of rewards are you offering to people To get to the next level? Is it like the highest level is like you spend a day with Greg?

Okay, it's all right. I'm looking. I just— and from a weekly perspective, we're basically around 60+%— so 60% are logging in weekly. And, you know, people say, oh, people are gonna— you know, people aren't gonna go to another social network. Yeah, they're already on Instagram, they're already on—

People go to what they care about.

They go to it. They go to what they care about. And if you produce value, they're going to go to your thing.

Dude, can you let me into that community? I just want to see how it is. Yeah.

You want to check it out?

Yeah, I'm going to join later.

Yeah, no worries.

By the way, have you met Sam Ovens?

I met him once. Yeah.

You know, he's in L.A.

El Segundo. I went over to the office.

Yeah, yeah, yeah, yeah. I was going to say, I'm happy to put you guys in touch. But so speaking of community, You know, you're— I mean, we were both in Miami for a bit. I'm back in L.A. now, obviously. But do you think Miami is still the spot for— do you think it's still the next, like, tech community? Because there's so many people going home. Yesterday I was talking to someone. His boss is thinking about going back. Pomp has gone home, right? Like a handful of people have gone home. So what's your take on it? Because I was just like, Miami's just so good for personal life.

Yeah, but go ahead. I mean, I never moved to Miami because I thought it was going to be a tech hub. I moved to Miami because I think the weather is really good and I find it fun and I enjoy it. And I wanted to be on the East Coast.

East Coast is such a hack, huh?

Yeah. Like, it's— I woke up this morning on the West Coast and—

You felt like a loser.

I kind of felt like a loser.

Yeah. When I first moved back here, I messaged my friend because we had both moved back from Miami. He's like, Yeah. When you wake up on the West Coast, you're automatically behind and that's for losers. And I'm like, damn.

Yeah. So I, I do like being on, on the East Coast. I also like being on— I don't want to be— there's something about being in a city that's on the come up that's really cool.

You can feel the energy.

Feel the energy. Yeah.

Because as much stuff that happens in L.A. or S.F., it's like, well, no, S.F. has the energy, right? That's the AI energy right now. LA, it's very like, I'm from LA. LA is very broken. Um, I can say that because I'm from LA, but yeah.

I can't say it?

You can say it too, I guess. No. Yeah, but no, continue. It's so like, I think you kind of mentioned like you're, you're a lifer for, for Miami.

Yeah, I'm a lifer.

Yeah.

I mean, assuming it doesn't go underwater anytime soon, which—

Not soon.

Yeah.

Yeah. You're good for a while. Yeah. Um, Okay, well, I'm with you on that. So we talked about being— how being a solopreneur sucks. And just so everyone knows, a solopreneur is like, like Justin Welsh, for example, right? Like he does well for himself. I think he does like $3, $4 million a year and he crushes it. Yeah, great business. But I think to your point, again, it's just, just to reinforce that we can move on. It's, it's, it's hard. It's tough. Like you can unhard the business just by hiring great people or working with great partners.

It's I also get energy out of working with people. Like, I love working with people. I love getting to know them.

It gets depressing just soloing. Like, I don't know if like if you play any MMORPGs, but when you're soloing all the time, like, it gets kind of depressing.

Yeah, so I mean, I'm one of those people that like the reason I played Counter-Strike is because I like multiplayer, not single-player. Yeah, and for some people, they might listen to this and be like, you know what, like, single-player sounds really cool. Like, what Justin is doing sounds really cool. And I respect that. I really do. But for me, I think multiplayer is a lot more fun. Playing with other people, sharing responsibility, learning, and being able to take a long vacation without, you know, being—

Things breaking.

Single source of failure. Solopreneurship also means single source of failure.

It's a lot of pressure. And you had a quote here, there's no middle class for solopreneurs, VC-backed entrepreneurs, or creators. Think about it. What do you mean by that?

I mean, I think you're either Justin Welsh and you're crushing it, or you're essentially a freelancer type person that's a solopreneur. I don't think there's much in between.

I agree with that. So yeah, you choose your suck. Both have their, you know, their suckages. Yeah, both are great in their own way. But here's another one from you. The size of the software market will tend to 100x due to AI being easy to create spinoff software. What do you mean by that?

People are going to press a couple buttons and duplicate SaaS startups and software. And for a lot of people, that's going to suck. Because essentially everyone is going to become a programmer. What is a programmer? A programmer is someone who could create software. And if you can just essentially drag and drop, copy and paste, then there's just going to be a ton of competition for software. So, my thinking is, how do you stand out?

Right.

The only way you're going to stand out is by brand, a brand that people connect with, design. Design that like feels really good. Community.

Dude, I want to go to design in a second. I actually didn't have design in my notes here, but like, it's interesting because I was talking to one of my developers the other day. I was like, you know, the last year and a half, how much more effective have you become? They're like, 8 times.

Wow.

And I'm like, wow, 8 times, really? And this is just the beginning right now with all these people using Copilots and things like that. And remember Jensen Huang was like, You know, the CEO of Nvidia, he's like, yeah, screw teaching your kids to code. That's not going to matter anymore. Like, what matters is like, you know, social skills or leadership, communication, um, you know, design, right? So yeah, I think it makes sense.

Yeah, I think he— I mean, yes, he's right, but at the same time he's wrong because, you know, it's not about learning how to program. It's learning how to think like a programmer. It's, you know, understanding, like, I ended up dropping out of computer science school, but I only had 3 computer science classes.

But that was still enough to get you thinking.

I kind of like, yeah, it got me thinking. It's like, okay, like, it also gives you cred when you talk to engineers because you kind of like speak their language.

So you like half agree. It's like, hey, at least take a couple of computer science courses.

Exactly.

Yeah.

You might not need to take like a 201, but a 101.

Yeah. Like, okay, that makes me feel better because that's what I did. So yeah. Yeah. How about, okay, so on the design side, because the, the, everyone go check out Greg's stuff, but like the design is pretty damn good across the board. Um, and, you know, I'm just like, we work with a lot of great designers. They're really good at copying, right? It's like, you know, if I, if I want a new landing page, I'll just go to landbook.com or something and just say, I like this one, this one, this one, and then boom, Like a duplicate comes out, right? But I think, you know, to actually have original designs, that's very difficult. So, how does someone level up their design skills? Like if they're like an entrepreneur, right? They have like no design skills.

I think, you know, I'll just say like, I think probably thinking— if I had to think like a designer or think like a programmer, I'd rather think like a designer nowadays. And learning how to think like a designer is really important.

Why?

Well, I just think that going back to like the AI software thing, it's like if every— if you believe that software will be duplicated and, you know, let's just say the last 10 years was the year of the engineer, I think the next 10 years will be the year of the designer.

Hmm.

Like taste, you need taste to know to create like essentially a mood board of interesting— you start with a mood board, right? What are the different ideas and design inspiration? You put it on this board, and then from that you distill what it would look like from a product perspective and a product design perspective.

Yeah.

So I think like what I would suggest to people is like learn, learn to think like a designer, create mood boards yourself, and And then get into the pixels.

Dude, I've bought so many like design books. I've just never opened them. So like, what's the one design book people need to read to think like a designer? Do you have any?

No. You know, you know, I think like, I, I think we're building like a something like this, like a, just a quick, you know, here's some, an email course based on this, how to think like a designer. Um, but like, no, I think like the way to do it is like you actually do it. Um, like the way to, you don't read a book, you go into the pixels. Like you push pixels, you don't turn pages.

I like that.

Yeah.

I like that. That's a good quote. Push pixels, don't push pages. Where do you think Sora fits in with all of this?

I mean, Sora's really cool. I mean, it's amazing, especially considering like—

How new it is.

How new it is. How 12 months ago we were in Will Smith's Spaghetti Land videos, and now we're in like Hollywood-style videos. So that's really, really cool. But I still think that like taste is the— is what's going to separate good Sora videos from not so good.

Because the thinking guides the execution.

Exactly.

Yeah, makes sense. You actually had a tweet here on how to build a $25 million revenue business with just one person. So this is like— but this isn't exactly— to me, this is much more highly leveraged solopreneurship because I'm assuming you're leveraging a lot of AI. But go ahead. I don't want to put words in your mouth.

Well, yeah, I think, I mean, you can't do it on your own, right? Like, you're not going to be able to do it exactly on your own. This is almost like micropreneurship, you know? It's like, it's like a micro team. It's like you and a couple of people or you and a bunch of AI to facilitate facilitate what you're doing. And I think, you know, right now, let's say you could create a, you know, $5 million a year Justin Welsh style business. But I will say in like 5 years with AI, that'll 5x.

Yeah.

Yeah.

You actually had a thread on— so like BuiltWith, we know, and this is your thread, $17 million a year with one person or $14 million or something. And then I think you had a gaming company in there that does like $300 or sold for $300, $500 million or something.

Yeah, it's like, it's doable. Yeah, it's doable. And it's only become more and more of a thing.

Yeah. And you have a, you have a, you have a tweet here. A viral post can change your life. It has, it has changed mine. Yeah, but it's basically a casino. Luck is involved, but it's more poker than it is roulette. And I like to call social media— I'm like, all these reels that we're posting right now, it's like a slot machine. You don't know what's going to hit.

Yeah.

And the ones— it's like the stupidest ones that hit too. So please elaborate.

Yeah. I mean, Of course, there's best practices. Posting every day, good practice. If you're creating videos, getting people to watch the whole video, good practice. Calls to action, good practice. Asking questions within a video, good practice. All these things, right? That being said, the algorithm is kind of a black box.

Yeah.

And sometimes it giveth and sometimes it taketh. Sometimes just like I'll go in spells of just posting and no one sees my stuff and I have to be okay with like, you know what, I'm gonna wake up this morning and I'm gonna post something.

Yeah.

And it's the same thing we were talking about earlier, shoot your shot. Like, you're not shooting, you're not hitting. You need to shoot. And so yeah, it's a slot machine. And you kind of have to pull the lever. Yeah, keep playing and realize that you're playing a game. Like, this whole thing that we're doing— likes, followers, content—

This is a game.

This is— it's a game. Yeah, like, why— how isn't this a game?

Yep.

How isn't it a game? You know, like, the followers were like collecting Pokémon.

Mm-hmm. Everything's a game.

Everything's a game.

Yep.

Like, why didn't anyone tell me this?

That's honestly how I see life. Like, literally wrote a book on it. But like, every single thing you do, like even Brad's computer over there is a gaming computer, right? Like everything. So what is, I mean, your process? Because you have some posts where you have like millions of views on it or like hundreds of thousands. What is— and your main weapon of choice right now is Twitter?

Twitter.

Okay. Can you talk to us about What your schedule looks like there? Like, what is the process? Like, how often are you writing? Are you like jamming it all on a Sunday, or like, what are you doing?

I have a notes file on my phone. Mm-hmm. And it's called Ideas, and it's just a bunch of ideas. Mm-hmm. And tweet ideas and stuff like that. So I'll just like go on life, like I'll have a conversation with a friend and it'll spur something and I write it down. Mm-hmm. And then on Fridays I'll spend like half a day combing through it and then writing content based on that. And that's it.

Is it when you think about the ideas too, is it like you look at it and be like, whatever one riles you up a little bit or you have like a hot take, is that how you pick it or how do you select?

Sometimes I'll like, I'll post something and I just want genuine feedback. So sometimes I'm like, I'm interested in talking about how like how there's like some internet communities making 8 figures a year. And I'm just gonna post it and see, maybe other people will post other examples, and that'll get me to think about a longer post I'll do on my newsletter.

Hmm.

So the newsletter that I've been doing has been like a really good outlet for me too, 'cause I take like my, my little tweets and then I'll just expand upon it. So what my, my process is like, go on with life, Don't force it, right? Just like have ideas, get that creative inspiration via podcasts, meeting with people, going for walks, working out, whatever. Allocate a certain amount of time, call it a couple hours, 3 hours once a week to comb through those ideas and expand upon it. Post them. Ones that are hitting well, go deeper on the weekly newsletter.

Got it. So you're— I mean, it sounds like you're just You're not doing like every day. You just, when you find the right one and you're feeling good, that's when you let her rip.

Yeah. And that again goes against like best practices. Best practices says post twice a day on Twitter. No, I'm not going to do it.

Yeah.

Why? Because I don't want to— I want people to see my post and be like, babe, wake up.

Yeah.

Greg posted on X.

Has that ever happened before?

No, no. But that's like, you know, I think that's what every content creator should be.

Yeah.

Aspiring to do that. Like every post feeling like a drop, not a post, like, like a huge drop.

Like a shoe drop or something.

Yeah, exactly.

You know, it's interesting. So like Alex Hormozi does that, but he goes hard, like whatever, like stream of consciousness from Twitter. And then that guides the video, that guides like whatever, and then that guides email or whatever. And then, you know, podcast co-host Neil started copying that and everything comes from that. And the best performing tweet leads to like a webinar. And then good performing ones maybe go to like a newsletter, right? So it seems like it's kind of going more in that direction now because Twitter/X is more forgiving because they don't, they don't like limit your reach based on how many times you're hitting it.

Totally. Yeah. And it's just like, it's easy.

Yeah.

Like you can be standing in line for coffee and just—

Yeah. Your, your content team. So in general, when I ask this question, people are spending around like Anywhere from— a lot of them are spending like $100,000+ a month or so on their content teams. Like, how is your content team structured and how much do you think you're spending per month?

I was spending, I think, $7,000 a month on short-form video and I just cut the cord.

Yeah. Wasn't doing it for you?

It wasn't doing it because it didn't— like the thinking at the time Was like, everyone was like, well, if you're doing a podcast, you just like cut it up and, and then you can take those clips and just like, you're doing it anyways, just post it.

Yeah. You're like, yeah, it makes a lot of sense.

Makes a lot of sense. Let's do it.

Yeah.

So I'd been doing it for like a ton of time, like over a year.

Mm-hmm.

Didn't get any traction. And the reason why I didn't get traction, I think, because my podcast is I only talk about startup ideas.

Yeah.

So I just say, I bring people, it's called the Where It Happens podcast. People come on and I'm like, what are some startup ideas you have? And we just talk about it. That sort of content format doesn't actually, it's not like the viral moments that actually hit for short form. And for that reason, it lends itself better to long form. So you have to ask yourself, If you're creating short form, is this a babe, wake up moment?

Yeah.

And it wasn't for us. Yeah. So I actually don't spend a lot of money on content. I spend like a few thousand dollars a month on—

That's the best deal.

On podcast editing. And then I write my own tweets and I post my own newsletter and that's it.

Got it. And your pod, you're doing it mostly remotely, right?

I'm doing mostly remotely.

Got it. How many hours do you think you dedicate to writing? So including the tweets plus the newsletter?

5 hours a week.

Okay. Yeah, that's a good amount. It's not a crazy amount. It's a good amount. Yeah, it's like, you know, an hour a weekday or something.

I mean, it helps me clarify my own thoughts and clarify my own takes.

Do you ever, um, do you ever just like test your idea out there? That's like you have a controversial take and you just want to see someone like break your thinking?

Totally.

Yeah.

Yeah, sometimes I'm in that mood. Like, I have moods, right?

Yeah.

And I— that's the other thing. Like, I don't want to be a robot on the internet. You know, I want to be like, I'm a real person.

Yeah.

With like, uh, real feelings and real, you know, sometimes I'm happy, sometimes I'm sad, sometimes I feel like this, sometimes I feel like that. And that's what I want people to get from my content also.

I think that the way your company is structured too, it works out because you're not like a day-to-day operator.

Yeah.

Like, you know, when we record the Marketing School Podcast, I'm pointing at Brad. It's like, it's— I'll try to goad Neil into a hot take about something, and I'll go off sometimes. But he holds back because he has like his enterprise clients, right? And he's like very much the face. I am kind of the face of my company too, but it's like he has to hold back a lot more. And then afterwards he'll be like, man, you know, I want to jump in sometimes.

Yeah, I think, you know, we've got enterprise, we've got Tons of Fortune 500s that we work with.

These are like $10-20 million deals. They hurt.

Our average deal size for our innovation agency is 7 figures.

But you're not the face, right?

Well, I'm not the CEO.

Yeah, there you go. So you have more freedom to say what you want.

Yeah, I'm not the CEO, but I am a co-founder in it. And some of the reasons why some of the clients want to work with us is because I'm attached to it. And they get some of my thinking and methodology. But I think, I don't know, I think like if I, you know, I think people want authentic, honest opinions.

Okay, here.

And I think that you can't lose by being yourself and being honest.

I'll give you a hook right here. This should do well. So, you're an entrepreneur. What do you think about DEI?

DEI, like diversity inclusion?

Uh-huh.

Well, first and foremost, I'm a white Jewish guy. So, that is a whole— I don't know. Some people see me as white. Some people see me as Jewish.

Some would say you're a double oppressor.

Why would some people say that?

Well, okay, it's like, for example, everyone, Asians are actually considered oppressors as well. There's like oppressor and oppressed, like this whole model, right? Now, if you're white, you're considered oppressor, but then Jewish people are also considered oppressors, right? I'm not saying, by the way, we're not saying we agree or disagree. Some of my best friends are Jewish, by the way. So none of us have any problems, right, with race. But anyway, that's, you know, that's the, that's how it's understood. With, uh, in public.

Yeah, I mean, I think it's, I think it's horrible that anyone doesn't, who wants to do something, is limited by their race or their religion, period. Like, full stop. I think it's And I connect with it, like, honestly, because, because I'm Jewish and because it's a cause I care about. And we're investors in the space too. Like, we invested in Debut Capital, which is a fund that invests in Black and Latinx founders.

Mm-hmm.

So, so we put our money where our mouth is there. And so what do I think about DEI? Like, I think that's— I think—

Do you think it's helpful to business?

Well, so, so the, so the first question is like, I think it sucks that it's horrible that race and religion play a role in 2024. It's like insane. Like, I thought by this time, like, we would be Gucci. Yeah. You know, like, can't we all agree that, like, we're just all people?

Yeah.

And we're actually connected.

Or maybe we've gotten older and we're just like, this will probably never be fixed.

Isn't it ridiculous? Yeah, it's absolutely ridiculous. Yeah. You know, and then so the question is, how do we best solve this problem? And the question is, is DEI, like having like, you know, a lot of these, you know, Stanfords and Harvards have like DEI, I don't know, you know, I'm sure you know this, quotas and stuff like that. Is that the way to solve the problem? No, probably not. Yeah. Yeah.

Well, we were talking about this pre-show, but I think the only form of discrimination that's acceptable is based on merit. Right. And like all the other stuff to me is just noise. Yes, it sucks that like people are discriminated based on like their religion or the color of their skin. But like at the end of the day, in business, what matters is your output. That's it. Everything else is just a bunch of So, how do you—

so, how do you— like certain groups don't have like equal opportunity, right? So, the problem is you'll have a group that just doesn't have the opportunity. So, when they get to the point of applying to Harvard, they, you know, might not score as well on a test as a white kid. person, for example, that grew up in an affluent neighborhood. So how do you deal with that? Right? How do you, how do you deal with that?

So you follow Thomas Sowell at all?

No.

Okay. This guy's amazing, by the way. I'll tell you more about him afterwards. But okay, so Thomas Sowell actually said this. So he's a, he's a, he's an African-American. And he, in the '70s or '80s, he's just like, affirmative action is a bunch of baloney, right? Because, you know, at Harvard, they were actually letting in, you know, So they let in the white kids. But then he's like, dude, they're letting in African-Americans, Blacks, but they can't compete. So they end up failing. They end up flunking out on like a lot of the tests. And you are actually better off sending them to another school where they probably would have done pretty good, but they just can't compete. And so they end up getting screwed over because of affirmative action. So I do agree with, with equal opportunity, but like, you know, stuff like that sometimes ends up not working out. So, for example, maybe 10 years ago or so, when I was in college, right? There's a period of time where Asians actually, like, you— we couldn't get into anywhere, right? Like, I had pretty good SAT scores. My GPA wasn't amazing because all I did was play games. But like, you could see a graph where for Harvard kids, for Asian Americans, like, the number never went up. Like, if you're Hispanic or Black, 44%, you're getting in, 55%, you're getting in. And they have white kids, maybe like 15%. Asians always like 11%, 12%. Number really never got better, right? So I think as good as the affirmative action stuff sounds, it like, it's been proven it doesn't really work and it ends up screwing the kids that, that we try to create equal opportunity for. So do I have an answer for what you're asking? Like, no. But like, am I for equal opportunity? Like, all day.

Mm-hmm.

Yeah.

I mean, I wonder also if like you go earlier in the life cycle of people, you help them earlier versus like at the point of applying for jobs or at the point of, um, applying at schools. I wonder if that is like the key to actually creating a more equal world.

Yeah, or I think I'm pretty sure you look at it this way too. Like, I've hired people out of high school Right? They didn't go to college. I've hired, yeah, I've hired, you know, brown people, yellow people, black people, white people, trans people, like everybody, right? I think sometimes it's just about giving them the shot. Like, if you have a good radar for it, you just give them the shot. And so it's like, but that's a very subjective thing, you know? Like, I feel like you probably give a lot of people shots.

Oh yeah. I think, I think at least half of our—

On paper, they're probably not qualified.

I think at least half of our team is people of color.

Yeah.

Like, I grew up with all sorts of people. So to me, like, it's weird when—

That becomes a thing?

That becomes a thing. Yeah. And it's weird to be in, like, I think that's what's cool about Canada, actually. Like, you know, cities like Toronto, Montreal are so cosmopolitan. There's all sorts of people together. So, um, yeah, I, uh, I don't have an answer, but I don't think that we're going— I mean, what's happening right now isn't working. Like, the world is more divided than ever, right? So, sucks.

Yeah. This message is brought to you by Single Grain. Single Grain is a marketing agency ran by yours truly. Single Grain does paid media, SEO, creative, conversion rate optimization, and has worked with a handful of companies such as Uber, Amazon, Airbnb, Salesforce, to startups, venture-backed startups, a lot of different companies. And ultimately our mission is to do innovative marketing that drives customers. If you want to learn more, just go to singlegrain.com. Again, it's Single Grain, grain like wheat, and we'll see you on the other side. I have one final question to ask you here. So what other ideas are you excited about? Because you literally have a podcast where you talk about ideas. So give us the, like, the top 2.

I'll give you, uh, okay, a couple that come top of mind. One is, do you know Coffeezilla? Yeah, yeah, yeah. So Coffeezilla is crushing it.

Do you want to explain who he is real quick?

He basically is an investigative journalist, so he'll like go and research, you know, I think, uh, was it Logan Paul? He had like—

Yeah, his NFT project.

His NFT project. It was called, uh, CryptoZoo.

Oh, that was his game that he made. But then he had, uh, there's another one called like 99-something. Like, he takes a picture every day, 99 pictures.

So what Coffeezilla will do is he'll, he'll look into who's scamming people and do a really good job actually at, um, of, of basically like, here's what's—

High production.

Yeah, incredible. Yeah, incredible. And he's been able to amass like a 2 or 3 million person Minimum subs, sorry, 2 or 3 million subs, I think, on YouTube. Um, I think there's an opportunity to be the Coffeezilla but for technology.

Oh, wow. Yeah, interesting.

So Coffeezilla for technology, and actually Coffeezilla for X, yeah, in general is a huge opportunity. Now, a lot of people don't want to be that.

It's tough because every— like, so many people hate you.

So many people hate you.

Yeah.

So if you can get past that Yeah. You can build a really big business on TikTok.

We will invest in you. Yeah, but just don't list us as investors.

Yeah. So, there's— that's one idea for you. Another idea is I was looking at James Clear launched an app called Atoms. Did you see this?

I saw it from your posts.

Yeah. So, James Clear, New York Times bestselling author, Launches an app around habits. That's his whole thing. He's about, you know, get 1% better and tracking habits and stuff like that. So he built an app specifically for his community. And I was checking the App Store yesterday and it, you know, it's beating Spotify, it's beating Netflix, it's beating HBO. It's—

Your screenshot when you showed it was like number 17. What is it now?

Number 13. Like, you know, it's going, it's going up and up. Yeah. And now granted, just because you're charting doesn't mean, as you know, that you're, you know, you're gonna last. But I think there's something really interesting here around how do you partner with a creator and build software. So, um, in that particular James Clear example, Tiny, which is the holding company from Andrew Wilkinson, partnered with James. I think they actually— I saw that they negotiated the deal via text message.

What, do you know the, the splits?

60/40.

Okay.

60 James, 40 Tiny.

Pretty significant still for Tiny.

Yeah, still very significant.

Yeah.

And Tiny's gonna do the operations, and James obviously is like the talent.

Yeah.

I think there's like 100+ opportunities similar to that. And I'm particularly interested in partnering with people like that and building out these applications.

I mean, there's 2 more examples like Ali Abdaal, like all of a sudden I see like a keyboard coming out, like, and then you have MrBeast with ViewStats. Yeah, that like most people don't know, ViewStats is pretty awesome for thumbnail testing and headline testing. So yeah, we're going to see more and more for sure.

Yeah, but I think like I love Ali Abdaal and he's a homie, so I would tell him this to his face.

Yeah, you're gonna tell him what I'm thinking.

I wouldn't— I personally wouldn't be building a keyboard company because of like the headaches with like supply chain and—

He probably should just do an app too.

He should probably, yeah. And I wouldn't be surprised if he did.

Yeah.

Yeah.

All right, well, I think this is a great place to end, but where can people find you online?

gregisenberg.com.

Just my name. And @gregisenberg?

Yeah, @gregisenberg. I-S-E-N-B-E-R-G.

All right, thanks so much for doing this.

Thanks, man. It's been real.