Eric Siu interviews Greg Isenberg, the CEO of Late Checkout, delving into the nuances of community building. Greg, a master in this domain, shares insights on fostering online communities for substantial growth. They explore the future of programming, the importance of design skills, and the power of social media. Greg also discusses the role of AI in entrepreneurship and the challenges of diversity and inclusion.
Watch the full interview here: https://youtu.be/kdnX63OEP5I
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All Right, Marketing School listeners, this is a twenty to thirty minute segment of a full interview I've done with an amazing.
Founder, entrepreneur, creative visionary.
You're gonna get a ton of insights from this, and if you want to listen to the entire thing, go search for leveling Up with Eric Sue. That's the entire podcast that you're going to find, So you can get twenty to thirty minutes here, and if you want the whole thing, you can just search for leveling Up with Eric Sue And without further Ado enjoyed the episode.
All Right, Greg, how's it going?
Man? Go well, Man, I like my T shirt. I like your T shirt. You know where'sus from? This T shirt is from HRUs because it's the same.
Yeah that makes sense. Yeah, 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 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 twenty years, and I've started and sold three companies before the age of thirty, all using the same community based approach. And 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. And yeah, I've created small communities in the in the dozens. You know, people think of communities, you know, you can't monetize them, but you can, you know, you actually can. You can have a community of a dozen people and make twelve million dollars a year. Or you can have a community of one hundred and twenty thousand and make one hundred and twenty thousand dollars a year. So I've built million, 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 LA. You're 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 off to SF, we're just talking, we're just talking about this pre show or you 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 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 this?
Because I one thing I love doing is throwing dinners with people that I really respect. So and I tried to cap it out like eight to ten 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 in everything just kind of 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 twenties trying to like build my network, I would throw dinners all over the world. You know, I was living in Montreal, Canada at the time, but I wanted to bootstrap my network and I wanted to meet, you know, the most successful people I can 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 and yeah, you want to make it easy on people, so.
You pay for it.
But you know, if you're paying one hundred dollars ahead and there's twelve people there, it's twelve hundred dollars, 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 have been seventeen years old, and I somehow was able to have drinks with four other people, one of which was of extremely famous entrepreneur, and we get three rounds of drinks and we were at.
A hotel called Hotel cost.
I don't know if you know it in Paris, probably one of the nicest hotels in Paris.
I'm a teenager, what the heck?
Yeah, so I take all my money, I know, I go, 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 VOD castas. We're having Vod castas and at the end the bill comes and it's like right in front of me. Of course, I like thinking to myself, like I have to pay right, I'm not going to be like I gotta go to the bathroom. It's like right there, So I put down my credit card bill comes back. It was like sixty five euros 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 ever 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, well.
And yeah, you know, I I'm glad I did because there are a lot of situations where I did things like that and not suggesting people get into debt to yeah to 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 than 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, there were finance internet communities and.
I was at loeb too.
This is in you know, mid two thousands, 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. Now.
Did I go up to a bunch of people who turned me down and stuff like that? Absolutely, But I just so happen to be lucky to 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. Two 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 you from originally, I'm from Montreal, Canada, and what I mean, and you know, it's a great city. I don't mean it like literally get out of my hometown. But I meant like, provide a better situation for myself and you know, gain freedom and gain wealth and create impact.
That's what I was trying to do.
I remember one dinner that I did this is like an SF and that from that, there 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 it, like a deal with Liquor. I believe that before they were required by Google. You just never know, like there was 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 yeah. So when I was twenty two 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 seven pm and I was in Montreal at the time. I think it was like eight 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, I'm gonna I'm gonna go. 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 met 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 said, you know, 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 stumble Upon, which was an old social network, which I was sort of like, yeah, for you know, almost like the for you page, TikTok for you page before TikTok, Do you remember like.
A little after. It reminds me of dig a little bit, you know.
So, yeah, it was Ogre you know at the time, it was you know, well one of the largest social networks at the time. So he's like, kind of reminds me of stumble Upon, 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 stumble Upon. He's right there. So he introduces me to the CEO of stumble Upon. Four days later, I get an offer to buy my company from from from stumble Upon.
Wow.
All from that experience, I'm assuming you sold. I saw, yeah, we sold, you know, but yeah I sold that business. Yeah, and it was from taking that plane ticket.
Yeah. Well 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 off, 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 free show like you're here for a reason on the West because she's living 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 and and come back with feeling more motivative 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 what are they thinking about, how how to use AI in their businesses. We've We've incubated a 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.
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.
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 you're well. I think the networking piece is one piece of your learning stack. 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 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, you know, I'm in one with like the my first million guys and Sahel Bloom and Nick Nick Kuber 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. 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. The inspiration I get is a reminder of.
They all have kids, yeah, the 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 group think, group think. 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. I think your boring marketer will tell us. Yeah.
So our thesis is that community based products outperformed 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 you know, so I'll give you an example. So we we 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 twenty thousand 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 when amos one hundred people now.
And you're so you're doing the community agency thing. Can 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 hold Co, the hold CO will do is an eight figure hold go 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 because Sosahill 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 ninety nine percent of people or sorry, not productize the influencer led agencies. Yeah, right, And so that this is good to talk about because I know he's using a guy that that's operating 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 is 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 Systeed or AI you know tech stack basically to implement content creation and SEO optimized stuff. Well, that could be spun out as a SaaS business, you know, So I'd rather go and focus on building that business then going saying hey we should go build a completely other one. Yeah, yeah, I think it's that's how we see it.
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 revenue 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 it so 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.
Speaking of multipreneurship, 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 ten million dollars a year in revenue. You could, but you're the single point of failure, Like you have to check the you know, the bank accounts and you have to check, you know, make sure your taxes are filed and if they're, aws go down or something happens, like 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, is is you're sharing that responsibility with others. Sure you don't have one hundred percent 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 there. 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 hundred k 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 you know the one percent or point one percent that you know create an AI app. Let's say that's generating seven million dollars a year and it's just them, But I would argue that that's high stress. What I'd like about multipreneurship like 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 cool thing in like twenty twenty twenty twenty one 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 ten or fifteen percent, 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 that NNGM that sucks and it doesn't work out. And then I think you can hire 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 hosts an example. So nine Figure Agency and their template is literally just hiring people from like eye Prospects, right, and like these people have been there, his MN A person from my prospect, right, his CEO I prospect. 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 pair. It's almost like a pramid 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, yeah, I mean I also think that that's what's tough. That's what's honestly tough about advice in general.
Yeah, is like.
What 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 only like sharing experience experience sharing.
Exactly 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, yeah, I mean the proof is in the pudding. I also think there's a lot of like fakers out there. Yes, there's a lot I don't I don't want to name any names, Like, yeah, it doesn't matter.
We don't need a 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, And so for example, like you know, just because you were at Facebook in two thousand and six 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 gonna 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 things you were doing before, like you had the there's the fund, 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 like checkout in June twenty twenty, 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 where 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 me 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 fifty percent of a business that became Boring Marketing.
And you plug this CEO in Yeah, okay, got it.
No, sorry, there was a business that existed, like a seven figure business. We bought fifty percent of it, and then that business incubated Boring Marketing.
Got it.
Yeah, So I think that's smart, right, Like you're buying into business, so you bought fifty percent. You said, yeah, Like I have a I have a friend that he mostly buys businesses at like thirty three percent, 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 from 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. 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, one hundred 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. 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 lay checkout than it does in recent Horowitz.
What do you mean by that?
I know you like a spicy take, So that's why I'm given to you what I mean by that is in recent Horowitz and I don't want to pick on indrecent Horowitz, but insert big name VC is going to write you a check and the value is, you know, ninety percent 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 built some of the biggest communities on the Internet, sobuilding 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,