How To Grow A Small Agency Into A Billion Dollar Company, Shaan's $15M Miss, And More

His company, which is called Tiny, which buys businesses. It's going public. And Andrew owns roughly seventy one percent of the shares and it's going public at a nearly billion dollar valuation. Who knows what it's gonna actually trade at, but if it trades at what they want it to trade at. That's about seven hundred to eight hundred million dollars.

That Andrew will have from it all starting with a bootstrap agency. And I wanna walk through his journey. And I think this is amazing. It's pretty mind blowing. Alright, let's do it. I'm um Fancy shirt. Fancy shirt. All I gotta say is fancy shirt. I've n I now do this thing where if somebody does anything that's like

I feel like they left the house today feeling good about that or they you know, they got a haircut. I'm not subtle about it. I'll just I act like a Like a dog barking. I'm just like, nice haircut. You got you you changed your face. The thing that the audience is gonna call me out on. Is I I couldn't find my other glasses, so I have to wear these glasses.

The problem with them Is that asshole Jeffrey Dahmer? Decided to wear the same one. So it looks like I'm gonna ask you like Do you wanna come back to the apartment to take some faithful pictures and have some beers? It'll be real nice. Like uh that he ruined it for me.

Some people are into that. I have a meety one, another publicly traded company. This is a big deal. And it kinda has not been made a big deal in the media because It's I guess not that big a deal to them. It's a billion dollar company. But basically our friend Andrew Wilkinson. Friend of the pod.

friend of ours. We're gonna be with him in Vancouver on February sixteenth. So if you want to come see us uh live. He Basically And by the way, I gotta preference this now that he's a publicly traded company. Everything that I'm gonna say, I just Googled it. This is all just from Google. I didn't ask him anything, and a lot of it's guesses, but not all of it. He basically had a company that was publicly traded called We

We commerce and it was not doing great. It like peaked at like five hundred million, went down to eighty million. Anyway, he's doing a reverse takeover. No, sorry, he's doing a merge. And he's his company, which is called Tiny, which buys businesses. It's going public. And Andrew owns roughly seventy one percent of the shares and it's going public at a nearly billion dollar valuation. Who knows what it's gonna actually trade at. But if it trades at what they want it to trade at

That's about seven hundred to eight hundred million dollars. That Andrew will have from it all starting with a bootstrap agency. And I want to walk through his journey. And I think this is amazing. It's pretty mind blowing. Okay, uh the by the way, the billion dollars is this uh one problem, by the way, is that all of his numbers were in Canadian dollars. It was all CAD. Instead of USD. So is this a billion cat or is this a billion US D? Everything I'm gonna say is Canadian. And I don't know what the conversion rate is of monopoly money to USD, but like it's it's somewhere close enough that we're still in the same ballpark. Yeah. So I think it's I think it's a little bit more like seven hundred million is the the the number that basically just discounted something like twenty, thirty percent. Andrew's in

Cad is Canadian. Andrew's in Canada. If you ever really want to inflate something, right? Like Mm. If you're five nine. You're you're 5'11, Cad. So just just go CAD and you'll you know get that extra get that little extra that you feel you've been missing your whole life.

So dude. This story, it's really impressive. And Andrew comes on the pod and we mess with him. But like This is We treat him like he's one of us.

He's pulled off is like not one of us, man. It's pretty epic. He's the Brian Scalabreedy of Rich Guys. You know what I mean? Like this is the He's the worst billionaire I know, but he's The best millionaire I know. Yeah, for sure. I mean, he's killing it. So listen to this. So Basically the company that is taking public it at this point has and this now this stuff is actually uh public. Uh it's doing about 150 million in revenue, 50 million in EBITDA.

And so here's the story. So Two thousand six, Andrew was I think nineteen. He started a web design agency called Meta Lab. And Meta Lab is like The core of all this. In year one, it had two hundred fifty thousand dollars in revenue. And basically what he's doing is he's doing like design stuff. So uh one of his big famous clients was before Slack was Slack Stuart Butterfield. He

you know, reach out to Andrew and said, Hey, help me design Slack. And like I don't know it's web interfacing, which frankly I don't even know entirely the the whole Scope of that work. But like more than logos, but including logos, I believe, right? More than locus. That should be their tagline.

No, it was definitely We draw good. We draw good plus more. Logos and more. No, it was it was web interfacing. So it was actually fairly technical. But in year one, it did two hundred fifty thousand in revenue with a fifty percent profit margin. In the year two uh two thousand nineteen, so th three years in. It was doing about a couple hundred thousand in profit. And it doubled uh for a couple of years and then grew by thirty percent a year. So two thousand twelve, you're six years in.

Only three million in revenue. Not like Right. Crazy out of this league. Like You know, he's he's kinda like what people say about us is You're relatable. And whenever people say that I'm like

I don't want to I don't want to be relatable. I want to be way out of your least. Yeah. They say you're so you're so authentic. You're so relatable. What I like about you guys is you're not that successful. Yeah. And you're pretty dumb. So it just feels good. You guys can so That that's exactly how I feel. So he he was relatable. So in year six Three million in revenue. But after that it grows thirty percent a year. Which by which if you add up thirty percent annual growth by two thousand twenty, you're at something like twenty million revenue. By two thousand twenty three, you're in like the forty or fifty range.

And The reason why Andrew's agency works so well is And I actually think this won't work. This doesn't work as much anymore, is he's based out of Victoria Uh w I don't even I'm such I'm so ignorant. I don't even know what state Province. Minnesota, but a little higher. Yeah. Yeah. Yeah. He's in like yeah, he's in like b the boise of Canada.

Yeah. Upper Idaho, I guess. Our software is the worst. Have you heard of HubSpot? See, most CRMs are a cobbled together mess, but HubSpot is easy to adopt and actually looks gorgeous. I think I love our new CRM. Our software's the best. HubSpot. Grow better. And so what that means is he's paying those wages But he's charging Silicon Valley pri British Columbia. Ben just corrected me. There you go. British Columbia, whatever that is.

Uh, I don't know what piece that is on the Monopoly board, but it's somewhere around there. And so he's charging Silicon Valley prices to like the slacks of the world. So these high end prices, but he's paying Canadian wages. So that margin is fat. And so that's why he's able to take make all this uh profit.

And he starts taking his profit and he starts launching companies. And it doesn't work so well. He launches one little software company Uh, I forget what it was called, flow, I think. It was basically like an Asana competitor. Does it work out. He's like I invested too much money, goes Fuck this. What if I just buy a company? He reads a book on Warren Buffett.

And he's like, Yeah, yeah, yeah, I could do this. And that's his new hero. He turns into a a buffet guy and he starts buying businesses. And he buys a coup that are doing okay. But then he buys one that becomes like the crown jewel of this whole business. So this whole thing tiny There's I think there's two crown jewels. There's Meta Lab, which

it we can guess is doing forty or fift million in revenue, twenty million in profit. That's the cash flow engine of this whole thing of being able to buy these companies, then he buys Dr uh Dribble. Which is basically like GitHub or designers. So designers go to this website.

And they upload their portfolios, other people's can uh share your portfolio. You send it to employers, they can comment, you get inspiration, whatever. Now, I don't have all the details on this, but I if I had to guess, Dribbble was launched by two founders who weren't very business savvy and it had a lot of traffic, but they're like, dude, we don't know how to like make money off this. And Andrew buys it from them, I imagine I had a guess. I bet you he buys it for

five to ten million dollars. turns this thing into a behemoth making now it's making many tens of millions of dollars. If I had to guess it's worth Two hundred million dollars or higher. I'm this is just pure guess. And that becomes the crown jewel of this company, Tiny. And so now he's got these two agencies or uh Meta Lab and Dribble. And then he's also has now, what do they own? Like 15 other companies. And he's taking it public. And throughout this whole period, he's bootstrapping this thing. So Meta Lab is the one that's paying for everything. He hires the CEO to run Meta Lab. And because of that, he basically owns like ninety percent of Meta Lab, and now he owns

What did I say? 70% of these tiny shares. And then his other partner in the business almost like 10%. So him and Chris is his partner. own eighty percent of this publicly traded company that's hoping to go public in the billion dollar range. This is just a crazy fascinating story. And uh I can't believe he's pulled this off.

Yeah, I gotta be careful what I say because I invested in Tiny recently When it was private. Um So I kind of know More of the numbers, but

I don't know what's public versus what was private. Wait, am I in the ballpark of everything? Yeah, I think you're in the ballpark. Um I think the maybe the dribble valuation may be a little bit high. Um But you're right that those two things make up Like, you know.

It's like'cause i I guess here's my here's where this kind of broke for me and this is Maybe not that interesting, just a my personal Framework. Broke in a good way. Broke in a good way. In a good way, which was uh I thought he'd been around doing this for way longer. It was actually twenty sixteen when he started like

buying other companies. And um That's not that long ago. I met him in I wanna say twenty twenty. Yeah, that's four years in and it was But I had known about him. He was like a personality. Yeah, exactly. He always had this like cool looking avatar. His pictures always look cool. He was like a designer, so his hair was always slicked back. And he had this like where we all look like Dorks. He was like kind of good looking in his pictures and stuff like that.

Yeah, it just shows what a good head of hair can do for you. And um you know I think that's the real takeaway, number one. Um number two number two, this segment is brought to you by HIMS. Number three. Uh no, so so I think that that was the first thing which was wow, this was actually built up in a vr uh a relatively Like On one hand, it's a long period of time'cause he's been started Meta Lab a long time ago. So that part you gotta give credit for. Oh wow, two thousand six and then he grinded it out year after year, building the service business up.

But on the other hand. The portfolio side of things was relatively new. So I thought that was really interesting. The second thing. I assumed that the portfolio was a lot more a lot flatter, a lot more parody, so maybe like

There were Um you know. five to ten companies, all of sort of equal value, pitching in each one, like you know five to ten percent of the overall value of the pie, and that's how you get like, you know, seventy percent or something like that. And the rest was Metal Lab. And in fact it was kind of like

Like a venture portfolio in a way. where a couple of the companies were really the standout ones that were driving most of the value. And I think for them it was actually three. There was the The one they s took they originally took public, so uh WeCommerce, which is basically their Shopify apps roll up. Uh so the Shopify app roll up, I think was was one winner, Dribbble is another winner, and Meta Lab is another winner. And to me Everything else is nice, but now that those are such big winners the

They make up so much revenue and so much EBITDA that the others are almost like rounding errors. At the moment. Uh that's a little bit harsh, I would say, but like yeah, so maybe that's maybe that's a little too harsh, but just comparatively, it wasn't like this portfolio of a dozen equally sized companies. Um

Which maybe Was I never should have assumed that in the first place. But when you hear somebody's doing a portfolio, you sort of think Okay, it's gonna be sort of more smoothly distributed out. But but it was actually a little bit

more concentrated in a few key key winners that just really kept compounding at a high rate. And um so yeah, so I think that's that's amazing. I think what he's done is amazing. Like um To build this level of a of a

sort of empire in this short of amount of time is uh It's pretty awesome and I the the biggest thing is I love that he did it his way. Like there really wasn't Anybody doing it. Exactly what he was doing. Um, of course there's private equity, right?

But he wasn't doing it like private equity because he wasn't looking to flip. He's looking to buy and hold. So then you have sort of okay, okay, who's doing permanent equity, who's doing a buy and hold strategy. Okay, there's some people doing it, but they all raised money. He used his own company's profits. To do it.

So that's pretty dope. And then he branded it and was more public about it versus these kind of more under the radar It's like oh you you're part of like Maple Oak Capital? What is that? Uh you know, I go to your website, it's got two lines, it just says we acquire software companies and it's like okay, I I don't know what this means. Whereas he built kind of like a sexy brand out of it. So I think There was a bunch of things he did that were pretty cool. Like even his

Term sheet. He's like, Oh, I read that Warren Buffett Basically. You know, we'll meet a company, understand it, and then write a one sheet A one page, you know, like term sheet for them to just Yeah, are they gonna take this deal or not? He doesn't do this like

complicated lawyer process. If he could buy a billion dollar company with With a one or two pager, then I should be able to buy this three million dollar company with a one pager. And so he took you know, he took that approach and I think did a good job branding what he was doing along the way. Yeah, and so here's a few more takeaways and then I want to hear yours, uh if you have any extra ones. The first is that you said that he did this quickly.

Yeah, kinda. But he also did it really slowly. The acquisitions part only. Yeah. The acquisition part, but He basically started in 2006 and then he didn't really hit his stride until 2016. So that's 10 years. Of having an agency. Now he didn't run the agency the whole time. He ran it for a little while and then he also hired people. And so I'm I'm sure he was managing it to some extent. But slow is good in some cases. And the second thing is that He didn't raise money for an agency. And because of that, he had so much freedom. The second you raise money, that that your cap table is one of the few things that you can't reverse.

Or or it's really hard. And he didn't raise money for a company that sh Meta lab should not have raised money, and it did not raise money, and because of that He was able to use the profits to invest in shit versus if you raise money, they're like, No, don't use those profits to do other things. reinvest them and make this thing bigger.

The next thing is financial maneuvering. Like, you know, I joke that I like don't know anything about finances. It's kind of uh Like his like thing. I think I think he's built that skill up over time, right? Didn't didn't know it initially, but But yeah, has he can create a lot of value. A lot of people do this now, but they can create a lot of value by increasing their financial IQ.

Like Um Taking WeCommerce public via S back in twenty twenty when the timing was perfect. Um required Some combination of

Being prepared with a good business. Secondly, um, you know, identifying the timing and saying now's the time go aggressively. And third, is like just having the financial IQ. To go with the balls to be able to actually go pull something like that off. One hundred percent. The next thing is where you live. It can actually matter a lot. Now I think that this gap of Silicon Valley wages

And Victoria Canada wages might be closed a little bit. It's closer, at least, than it was before. That gap is smaller. But this still exists in other places. I know I have friends that have built pretty big businesses, are building them right now and they're using Indian talent versus American talent and they're getting great products. That's what you do with this podcast. Guilty. Um, and then the final thing is hiring and negotiating. The way he negotiated with his CEOs and kept them happy. Well also retaining equity, so I don't know like how he pays people I I I imagine he pays them with

Just tons of cash. Uh so that's like You're like, Well, that's easy. You just pay overpay people. But Anyway, it's still like really impressive how he's able to negotiate and hire and manage people. I've heard from a bunch of his CEOs where they're like

When things are going fine I don't ever hear from them and I love that. And then of course I imagine there's times when things are going fine. He's like, All right, dude, come on, we gotta we gotta like push this a little harder. But he's done a really good job of hiring and uh Anyway, this whole thing. That he's pulled off.

I messaged him and I was like This sounds like an insult. Yeah, we gotta clap. We'll we'll clap for him. I was like, dude. This sounds like an This sounds like an insult.

But do you ever just sh sit with like a shit eating grin? And just laugh at like a little evil laugh and be like Got him. I pulled off this caper because that's kinda what it feels like because He makes it look easy. And of course, it's never easy. There's like there's times where he'll message me and he's like, dude, I feel like I'm in the dumbs or I feel overwhelmed. He's human. But he's done a really good job of doing it his way.

Almost to the point where I'm like, dude, you gotta be smirking right now. Like it's that feeling like when you get successful and you think of all your ex girlfriends who like made fun of you. It's like you you've you fucking Oh, me only that thing. Yeah, you know that thing. No no no I got you, bro. No don't worry. You know like you know like that you know that that that shelf you have with like the names of all your enemies marked on like champagne bottles. You know like when you pop that cork off whenever you like. Yeah, dude. What are you talking about? But

He's pulled it off. Let me Let me also say another thing. You know that um There are people that are masters of engineering, you know, people that are um

You know, fantastic leaders. But you know I'm the dawn of storytelling. And Andrew is A great storyteller. So people should go read is dribble two point oh blog post. It's on medium. So uh just Google

Double two point oh Andrew Wilkinson. And Here okay, Sam. How do most people announce an acquisition? Um

Yeah. Just uh give me your generic thing. Yeah. There it's like uh we're so brought we are so press release. We're so pleased they built a really nice business and we're happy to be stewards of this business and we're really looking forward to the future. And then like the sellers like You know, we were looking for a nice home for Triple partner. This is a perfect partner and we're excited for the future. Just nonsense.

Not the absolute Absolute soulless drivel. So here's here's what he he did and said. So here's I'm just gonna read a little snippet of this because I think People should pick up on the storytelling too. I think that helps. So he goes. When I first started Meta Lab

Dan Cederholm was my hero. A great opening line. I'm going to go'cause I don't know who this guy is, and now I'm like, Why is this person your hero? He goes. The Bulletproof Web was the first book I read.

I used to reverse engineer his style sheets on simple bits to learn his CSS tricks. Anything he did, I did. And I drove my front end developers nuts trying to get them to implement Every little one pixel detail that I learned from Dan. So already you're like, Okay, this is interesting. He's basically setting the context of like That's the guy who started dribble and he's like

It's not just I bought dribble And I'm pleased to to, you know, raise prices in six months. He's like, you know, I uh I've admired this guy. This guy's my hero. I learned from him. And so when he uh so he so let me uh keep going so he goes. I rem I'm I remember meeting another favorite designer, Dave Dave Shay, at a conference back in two thousand eight.

He mentioned that he knew Dan on my floor my jaw hit the floor. Wait, what? Those CSS drop shadows, the court logo, he's the best. What's he like? I was gushing. Um blah blah blah. I wasn't just a fanboy. I was his web standards fanboy.

Uh blah blah blah. Then he keeps going. He goes. one of the projects that Dan did was Dribbble, which he co founded with whoever Uh I had used it. Blah blah blah. Which is why I'm excited I'm extremely excited to share the big news. Right. So just that little paragraph. Of setup.

it it draws you in in a way that like he could have just done a standard boring I roll press release and instead he decided to do it this way. And then he he talks about kinda like That it wasn't just like W therefore we've acquired it and it's done. He's like, I was bugging him and bugging him. I kept emailing them every month, asking them if they would let me in.

He's like this September if my Moxie finally paid off. He emailed me thinking saying they would think to do that they might do it. They cared about these three things. I wouldn't mess it up. I have a long term view and I want them to stay involved and own a piece of the business. We shook hands and made a deal. Um blah blah blah. And then he tells the rest of the the you know, then he then he does the standard stuff about we're excited, it's gonna be great. And um

I just thought that was just a way better way of doing it than the average person would do it. And if you add up A lot of doing things better than the average person would do it, you end up with this type of exceptional outcome. Yeah. It's just great, man. I I have a lot of respect from him.

There there's always like This little bit of envy in me. Uh when I talk to Andrew because he's my friend and uh I consider us peers. And but I then then he'll make jokes about like what he's doing on the weekend and then like oh that's sick. And uh I then

But I'm proud of him. I feel like I feel a lot I feel a lot of pride like On his pulled kind of for him. And uh I'm very happy that he's pulled this off. And I think it's really impressive. And I think that it's Badass that people

that there are people that are bold enough to do things their way. regardless of what the nerds and vests in from Stanford tell you the way you should do it. And I imagine that along the way, he got a lot of flack. Making fun of him.

From being in Canada. Uh for not raising money for buying these little quote little things and I guess that's the fucking name of the company, Tiny. But he just like

pulled it off and I appreciate that gumption and I appreciate that boldness. And I find it inspiring and I'm happy that like we have him in our life. So that's a little my little love note to Andrew. Good job. Love letter to Andrew Wilkinson. Yeah. And if you wanna it we're going to Canada. We're gonna be there February sixteenth. And Andrew, if you're listening to this, You wanna fly us up there, private?

That's cool. If you want to celebrate We know how much money you have now. So Look, let's celebrate my friend invite another over. Yeah, yeah, yeah. Let's celebrate by flying private together, except Will be like you don't have to be there. And Sean and I will each be in different planes.

Uh. So Can we have an allowance? Can he just send us a card with just an allowance? That would be tough. Um anyway, that's my breakdown of tiny. He deserved it. Dude, I got roasted so badly. by my daughter uh last night. I was like, Oh man, this is your four year old daughter rusted you so badly? Nice. Three. Three years old. We play so so she she can't play many games. We play um Rock, paper, scissors, but she always throws scissors. So that's like you know, fun for for her, not for me.

Um She plays hide and seek, always hides in the same spot. There's like kids do this. They just like play the game but they they don't know how to play. And then she so the so I taught her I spy. I was like, Oh, here's a game we can play in the car. Um Ice Spy. And so she loves I spy. So she so I'm like, I spy something green. She's like, Is it the tree? I'm like How'd you get it? It's always the tree. That's right.

And she goes, I spy something yellow. And I'm like looking around the house. I'm like what is it? Yellow? I I don't see anything yellow. She goes, Your T Oh she's not aware that that's the sickest burn that anybody's done to anybody. Hey, I spy an asshole. Yeah, exactly. I was like, wow, that is just like natural. That's a natural burn. That's good. Can I tell you about something cool that you probably know about and I saw it and I can't stop thinking about it. Have you heard of the scaling? I don't know about this. Tell me about this.

All right, this is th you know, I don't pay attention to sports. This is your league. So uh you don't you know Brian is Brian Cal Oh oh Scalabrini. Okay, I didn't know he called it the scalage. That's a good name. Well, ex explain who he is. People don't know probably. So Brian uh Scalabrini, he played for the Celtics. He's like a redhead. He's six nine. He's huge. But I think He looks like uh Will Farrell But actually was an MBA NBA player. Yeah, so easy to make fun of. What?

I think he was like okay, right? Or was he always Yeah, he he was okay, but then like it was okay, but he was a he didn't take himself too seriously and over time, you know, like he had a kind of a few years where he actually played, but most of his career he's on the bench as a scrub. And uh yeah, yeah, Bar Shop's his nickname. Yeah. Kobe was the black mamba. He started calling himself the white mamba. And so, you know, he was a goofy dude. Who was basically a bench warmer for like the last whatever seven years of his career.

Uh but it was a great, you know, great locker room presence and and you know, a warm body, so people kept him around. And I think at one point he called himself, I don't know if it's a joke or what, the worst player in the NBA. Obviously it was a joke. But anyway, after he retired. So I guess he retired from the NBA somewhat recently ish, but he's still six nine and athletic and whatever. Or athletic for uh, you know, he's a basketball player, but he compared to the other guys, he wasn't like that athletic.

But he starts playing rec leagues. And like he would score, you know, rec leads like at the YMCA and on uh playgrounds, and he scores like sixty points a game, you know, just crushing these guys. And he doesn't like brag about it too much, but then like online at one point he mentions like yeah, I got I got sixty points last night my recly. And then just people online just start chirping at him hard. And they're like

Dude, you suck. I could beat you. Or you I don't even know how you made it in the NBA, you know, yada, yada, yada. They start chirping at him. And he goes, Wait a minute, no. I maybe suck compared to Derek Rose, but I don't suck compared to any of you guys. And so he starts doing this tour where he goes to like uh all these basketball courts. He goes, I want to go to the the the the hoodest of the hood basketball court. I want to go to the best YMCA. I want to I'll go all around the country. And he starts doing this And he crushes these guys and he's he challenges people, he says, Come play me one on one. You think I suck?

Come play me one on one. Yeah, and he and he and he destroys them and there's he he's like I'm not even gonna do this for social media, but some people recorded a couple of these things and he would beat them like ten nothing. He was like, I let'em get one point just to figure out what they're gonna do, but I just destroy these guys. And he's got this awesome quote that he goes He said this to like one of the kids. It was like a eighteen year old kid who like plays against him in the any any any

crushes this kid and he goes, let's get something straight. I'm closer to LeBron than you are to me. And I thought I read that and I go, This is the greatest thing I've ever heard. This is awesome. It's such a good story. And he called it the scaling. And I thought it was so good. It just shows, you know, there's levels to greatness. Yeah, there's levels to this I think is the the perfect

The perfect takeaway from that. And also he's hilarious. He is so good. Um I don't remember this, by the way. We were When we did our our Camp M FM Getaway. Um

The the guy who came to train us, he's he trains like a bunch of NBA stars. So he trains Kyrie Irving, he's changed Trey Young. And so he was there and his wife Is in the W NBA. And uh she's like one of the best players in the W NBA. We're talking about the W NBA and how like

They're you know, the players are awesome, but they also don't It like high viewership. Like the league doesn't do that well. It's kinda like subsidized by the NBA. It kinda loses money. But you know it it It's good overall for the sport for there to be a women's league.

And so We were like, Yeah, well we had kind of a an impromptu brainstorm of like the same thing everyone says, which is can I beat her up? You know, like it's like when everyone says not beat her up, just beat her. Can I kick her ass? Yeah, what would happen if I fought her, yeah, exactly. Uh so basically we did a brainstorm of like what would you do to to Get ratings up or to like

If you were to launch a different women's league, like how would you get people interested? Because the problem is Uh, I think I saw this this crazy TikTok. It was like some team whoever won the championship last year, I don't I have no idea. Maybe it's like the Atlanta dream or something like that. And they came home to do their parade in the city. And it literally just looked like You know

If I walk to my bus stop here and there's like three people kinda loitering around, there's like a bum. And then you know, that was the parade. There was nobody there for the parade. And the the team was going down in the bus. And it was just like Other people were like why is this what is this Why is this bus here? What oh you you guys play a sport? I I didn't really realise that. So

There's this TikTok that went viral making fun of it. Um and yeah, the idea that That we all landed on was Basically the three or four three, four, five best players. should basically go on tour, like it's the An one mixtape tour.

And go city to city and challenge, you know, Eddie Five, you know, go play pickup. With any with dudes at any of these and live stream that Um or like cut that into clips. of them basically punking punking guys. Yeah, like beating guys who think they could beat them. And

Uh yeah, put some respect on their name. So so that was kind of the the marketing idea, but Yeah. If if the CMO of the W A is listening. Welcome. Dude, I love these challenges. There is another one where

Like uh uh when you're watching running, running's not a popular sport, but I love it. It's my favorite sport to watch. Uh Next to the UFC. And People were like they're not that they're like a two hour marathon. You do you remember that when the guy Elu Ew kept choking, he ran two hours. And he just looks so smooth. He looks closer to an animal than he does a human. Like his body is just like

He just you know, running a hundred miles a week for probably twenty years, he's just like his You look at his calves and you're like, I I can't believe that you and I are like the same. We're both humans. It just it's not even fair. He looks graceful when he runs. He looks beautiful. And it doesn't look that fast. And so they put a treadmill at the same speed.

And they go, Here's doing it with ease. He's doing it with ease and he does it for two hours. And they go, see if you can do this. For fifteen seconds. And they have this treadmill and like people can't do it for just twenty seconds.

They can't even run that speed. It's basically like Four minutes and thirty seconds a mile, which is like I don't know, would that be like sixty miles an hour? Yeah, yeah, yeah. It's like a sprint.

And um it's a sprint for most people. And uh it was really funny. No one could keep up with it. So I love these like that's actually one of the tenets of making content viral, which is it made you have to make something made to stick and you can make it stick by comparing it to real tangible. things that everyone can understand. And when you put one of these treadmills at that speed, you're like, Oh, I can't keep up with that for Ten seconds, let alone two hours. Totally, totally. Somebody said this about the Olympics. They go, The Olympics, there should be one civilian in every event. Just

A normal fit guy from the gym. And it should just be like just as a baseline comparison. Here's the average person, uh here's even like an above average person, and then here's the Olympians. Like let them all just let them line up in lane eleven. And see what happens. Dude, I would love that. I would love that. I have uh I've got I've got a big meaty topic. What do you have?

Alright, so I this is a story of A Multi million, easily multi million, pop. And t type in the chat how do the calculation of how much I I lost doing this. Let's see.

I would have invested at a company at five million And it's now a three billion ish company. Um, so you know, I I basically turned I missed out on a chance to probably turn something like twenty five K into Tens of millions of dollars. Yeah. Um okay, so here's what happened, but it's it's kinda there's kinda some some interesting things baked into this. So it's not just that oh I missed it, big deal.

Uh everybody misses misses opportunities. This is uh an interesting one. So back in Twenty fifteen. Uh, which is kinda when we met. Um, I was not a angel investor. But I liked the idea. I thought it sounded cool. I was a founder of a s uh of a company.

Uh and I was making I think T one hundred a hundred sixty grand a year. So hundred sixty grand a year. Back then you told me you're making one sixty and I was like, Oh, you're the richest person I know. I remember you told me you're making one hundred fifty thousand dollars. I was like, Oh my God. Yeah. I I mem I remember I was like, Man, find uh find somebody who looks at me the way Sam looks at me right now.

And the way the Sam looks at my pay stuff. And so um So yeah, I I I w was making one sixty a year, but in in California, you know, th you've kind of After taxes, now you're at like one ten, you're netting, you know, and then you pay for life, it's pretty expensive, blah, blah, blah. You you don't save much. So I didn't have much of a bank role, but I like the idea of being an angel investor and people Because our office was so dope.

When a founder would come, they would think that I'm a lot richer than I was, but just because our office was so Fancy. Which was only fancy because Our main investor owned the building and decked it out for himself. And like that's why the office was so fancy. It had nothing to do with me.

So anyways. I um I meet this kid. We're building a product. And I meet this kid, he's thirteen years old. And he uses our app every day. Our app was like a clubhouse type of app. He used to use it every day after school. Come home, use the app.

And he's hanging out in the Silicon Valley chatrooms, and we're like, dude, you should be like going and Go try to have a kiss. Like you know that should be your mission, not like Sitting in on this room talking about raising your series A. And um And so two things happen. One, he's like, dude, I wanna come work with you guys. We're like, dude, you're in middle school. Like I can't

Your parents are gonna kill me. I can't help you work for us. Oh, here's Here's what you can do. He goes, I want to be a scout. I said, Okay, go ahead. He'd be a scout for me, he goes. Um he goes he goes, What do you want me to do? I go, Every week

I want you to send me a company. That you think is awesome. And that you think I should invest in. And just write why you think I should invest. And send me the company. Now I have zero hope or really even zero plan to read this email. At the time.

I'm just basically giving this kid a homework assignment. I'm like, Yeah, this will help you Thing and most likely this is gonna be too much work for you. You might do it once. You might do it twice, but you're gonna give up by the third time, for sure. So I give him this homework assignment. Very first company he sends me

Is a company called A Plyboard. And so here's uh This was the second this is sorry, this is the second week. Hey Sean, here's the second company I want to introduce, Applyboard. What they do. They help international students find the right university for themselves and apply there on their behalf.

They have eleven schools contracting to pay them a commission for every uh for a student that gets that signs up. And they have fourteen more schools in the funnel. They have over fifteen hundred students signed up, hundred sixty thousand Facebook likes and this is all with ten dollars in paid marketing. It's actually pretty interesting, right? Like that's actually a a kind of a

A really good analysis and that's you know, simple, two lines. So I'm like, wow, this kid's thirteen, he's like you know, he's This is a good find and he's explained it well. He goes, Why you should invest. Now this is where he got a little off, but that's okay. He goes They started four years ago with offline consulting and then pivoted into a software business. They know the space well. They have four co founders. They have a very, very diverse

Skill set, blah blah blah. Um They have an algorithm, something something, and he says Um, their customer acquisition costs only a few dollars and their L T V is thousands, so they have sustainable growth. Uh, he goes, I'm trying to correct my shots so that one day I can hit the bullseye for you. If you have any feedback on the company, I would love to hear it. Cause the first one I didn't even respond. I always said like this is bad.

Um So this is his second one. And I'm like You know what? This is actually pretty good. I'm gonna take this meeting. So Guy is in San Francisco. He comes to my office. Love him. Super charming. This guy Martin.

Um You you've probably met like a bunch of these guys who are like there's there's something that's really just like uh I don't know, charismatic or charming about Dudes from like, you know, Israel or something like that. Like anyone who's like Israel, Persian, Turkey, there's like

It's like They're just so goddamn charming. Like they're just dripping with sauce. And uh What's Cliff's company? Effortless. What's our buddy Cliff Cliff W, uh Cliff uh Whitesman. Yeah, the um it's the audio one. I I I think he's uh Middle Eastern. I met him uh when when he was just starting. And I was like

It and he had Oh, he's Israeli, actually. Uh it he had that same vibe and in the office. I go, What's interesting about you or something and he goes, I can do a backflip. I got All right, well friends. Yeah. I said uh

All right, well, uh move that chair over. There's enough room here. Go, do it. And he did a backflip in the middle of my office. And uh his company now, Speechify. It's It it's in the unicorn territory. And I didn't invest in it, but that like he had that same care charisma when he came to my office, he lit up the room. I should I should have I should have known better. Yeah, he's got amazing energy. And uh

And so yeah, this is the So so he so I meet this guy, he's got the Israeli swag, I'm loving it, and then And again, I have never at this point I've never angel invested in a company, but I'm like, this seems like a great idea. And what they're why this is a great idea for people who don't know, it's kind of a effed up part of the system, which is Colleges in the US just have like surge pricing for international students. So it's basically like

If I'm a if I'm a state resident I get like cheaper tuition at state schools. Okay, but if I'm a US resident, I pay you know, f what I thought is full price. So maybe I'll pay twenty five K. uh to go to school at this place.

But an international s student will have to pay two or three times more than that. So they'll pay fifty to seventy five thousand for the same exact thing. They just charge them more. It's kind of insane. I don't really know even how they are able to justify this. But they do. And um and so you remember in s San Francisco University, was that what it's called? University of San Francisco? I I dated a girl that went like had ties there, and I remember walking around campus and it was only Chinese students. And and it's and it's not even good schools like University of San Francisco or USF or whatever, it's not even that good of a school. And so it's actually

It's uh it's actually a bit of a trick. It's like um international students just want to come to America. They can't differentiate between Uh you know, University of Utah and you know Um you know Columbia or whatever, like these different schools, they don't know the the lay of the land that well. They don't know that the school's in the middle of nowhere. They don't know that it's

not actually considered that prestigious or whatever it is, it's just expensive. But uh so it's actually a lot of these other schools that really take advantage of this. and have a huge percentage of their population coming from international, which makes up A disproportionate amount of revenue. So that's kind of like why the schools are interested. So they went to him and they were like, Yeah, we'll give you

Three thousand dollars if you can get somebody to sign up. He's like three thousand dollars? Oh, that's pretty good. And I think now they take a lot more than I think that now they take, you know, ten percent or something of the of the overall tuition. So it it's gone up since then. But um Anyways, so he pitches and I'm like

Dude. I just get yeah, I get I get caught up. I like the idea. I love this guy's personality. I'm like I'm in. He's like you're in? I'm in. He said, Fantastic. I haven't really talked to anybody else yet.

Uh, so I don't know all the round details, I said brother. Amen. And uh he's like all right. Love it. You're you're the first guy I met in Silicon Valley. You're my champion on this. And I thought I'm the first guy you've been Oh wait, hold on. I don't I didn't want to I didn't I didn't really wanna be the first guy in like you know first the dance floor is kind of like not not exactly the position to be in. So

Then he goes on to where he goes, starts pitching people and he starts coming back to me with And he He's a nice dude, he's an honest guy. Trust me, he says And they're saying no because of this. And I'm like, Oh, these guys are idiots. Don't worry about them. They they don't get it.

Next one. They came back, they said no because of this. And I by the third one, I'm like Maybe I should have been saying no. So I start to doubt my uh my conviction in this thing. But I'm still like brother, I told you I'm in.

I'm in. And uh Anyways, it takes him a little time. Dude, if you if the end of the story is you backed out on him and you were calling him brother. I wasn't calling him brother. In fact, I think he was calling me brother because that was like you know, it's like the Kabib thing where they just they just say brother a lot. Uh dude has knifed him in the back. Well, I didn't actually knife him in the back. I th I don't know I don't know exactly what I don't know I don't remember exactly how it played out, but I definitely

uh was stout. So so basically takes him a little time to raise the round. He eventually does get the round together. And I'm supposed to you're right, uh twenty five K check. Not even like some crazy amount of money, but to me at that time that was like It's like all right, well

It's kind of like My entire like savings for this year is gonna go to this one random Israeli guy's company. All right, uh, you know. I I I could lose this, but I would really hate to lose this. And I start thinking about, you know, am I am I ready for this? I don't know. And so I kind of just I don't back out.

But I don't uh I from what I remember, I didn't back out, but I didn't reach back out either. And so I think he probably emailed me once. I was like, Yeah, okay, let me know when it's time. And then he probably emailed me like three or four weeks like yo, it's time And I just like didn't reply to that thing and I I don't think anything really happened. But anyways, long story short, I don't invest. Um

Fast forward, you know, five years, I get a email from that same kid, Sarouche. And Sarusha's like Hey. Remember this email? Yeah, Plyboard's a unicorn now, huh?

And uh you know Well what do you know? Curious what you think about that. And I was like, I think I was an idiot. And I uh I think I was a total idiot. And there's actually a few kind of like takeaways in this for me. So the few takeaways are One.

Um Don't be a wuss. If you say you're gonna do something, just do it. That's just a a lesson for myself. And I think, you know, for most people Uh yourself included, that's that's rarely a problem. For me, that's more of a problem. Second.

Um I actually think I was correct that I was not ready to be Angel Investing at the time. Um And so I I should have either You could have done like a five thousand dollar check. Yes, exactly. So what I should have done is I should have said, All right, look.

I don't have the bankroll to place twenty bets, which is kind of what you'll need. You need twenty to thirty bets for, you know, angel investing to work. And so it's like, you know, I don't I don't realistically, I do not have the bankroll to do this. But that's okay. That doesn't mean I don't do what I want. It means I gotta be resourceful and find a way. So either Let me come in at a smaller check size that make it my version of you know, if an angel investor writes

Twenty five K. When they have five million dollars. then I need to write the proportional check for me and see what happens. Or I should have gone to somebody and said Hey, I actually found this deal I think is really good. You have the money.

Uh, which is what I did later with Lambda School. It was like, Hey, I like this company. Uh They haven't really raised much money yet. It's not proven, but like I think it's worth a shot. And I convince somebody else to write the check and give me some carry. So that's really what I should have done. To make this happen. But at the time my fear

Overroad. My like um Yeah, the the Yeah, not even ego. The fear overrode my like uh Ability to think like

From uh th just think like with a clear head and say, Okay, well, sounds like there's just a little obstacle here. And let's figure out how we're gonna get around it. I pay. A lot of people are embarrassed. They're say like Well, can I do five thousand? Like I remember doing a deal. I d I did a deal for fifteen or twenty five thousand when I didn't have a lot of money. Thankfully on paper it's turned into a a bit.

But I remember thinking like That's I wanna ask him if I could do five K if I don't want to look like a punk. Right. Yeah. So so I think I I should have found a way. And that's I think uh has been a common theme in my life, which is like A lot of good opportunities come my way.

And I say, I don't have the time, I don't have the money, I don't have the skill, I don't have whatever, and I rule it out. Even though objectively I'm like, this is a great opportunity. And the real answer is Find a way to Get the time or find somebody who does have the time. Finding a way to get the money or find somebody who has the money to help you out. Right. Like do do one of those things to get there.

Uh and this is not like a Small thing like Just doing the difference between doing that and not doing that. Would have been Again, tens of millions of dollars in this case, when it in the result case where it it worked out.

So that's one takeaway. The second is This guy's Sarouche. is like now become a general strategy for me. Which is

I always want to have like I don't know, four or five people who are kind of like way It's like it's like an anti mentor. Like you know, it's a mentee or something like that, right? It's like I wanna have people that are Young

Hungry And ignorant. Uh naive. Uh But that's an asset for them because they're young and hungry. Um, I want to have them more in my orbit.

And I need to find some excuse to have them in my orbit and hang out with them and and hear what they think is interesting and Meet their friends and and whatever. Like That is um You know, I think that is a an actual strategy that most people miss out on. Everybody wants to To s sort of climb up.

They're like, oh, how do I meet the person who's done more than me? Or is more successful than me, has more money than me, whatever. And they're focused constantly on like reaching up and trying to like Pull themselves up. And instead I found

so much benefit out of just having a crew, a small crew of like eighteen to twenty one year olds that I'm like, okay. You guys just think differently than me. You're worried about different things and um You're excited about different things than me. How do I have that In my life in some way.

And so that's actually become a a more core strategy. Do you do anything like that? Yeah, so listen to this. So we had this kid By the way, thank you for not making like an uh Epstein joke. I felt like I was treading I was like what you need is like Fourteen year old dudes that you hang out with all the time. It's like Yeah. No, I I so I'm thirty three.

I'm just now hitting the age. Where I'm no longer the youngest guy in the room, and I'm just hitting the age where I've got 15 years or so of experience, and I'm seeing younger people, and I'm like, oh. You're full of energy. You're gonna do something, but you're making an air here. And I'm just gonna let you I'm just gonna watch you make that air because it's good for you. I'm just now getting to the point where I'm able to be a little wise. And I'm seeing the importance of surrounding yourselves with young people. Here's an example. A year ago, Sean and I did this thing where we offered

five thousand dollars to someone who made a TikTok video from our Podcast and shared it. One kid in particular, his name was Michael. At the time, he made these videos that reach tens of millions of people for us. And we gave him the five grand.

And I went to email him and I was like, dude, you should do this full time and I asked him what his email and it was like You know, Michael at University of Michigan dot E do And I was like, Wait, who are you? He goes, Yeah, I just recorded this in my dorm room. I'm like, Oh, you're gonna be you're you're onto something. You're gonna be a superstar. Just start turn this into a company. Turn this into a company. Uh I guess R five K was the first money.

He makes Tens of thousands of dollars a month. eventually sells it to Morning Brew. Um Michael, what's Michael's last name? I don't even know. Sican. Sican. Yeah. And He comes over to my house and uses the studio and I just he'll

means Sarah will be in the kitchen. And I'll just I go, Mike, come out to the kitchen, have a coffee with me. And me and Sarah won't say a word and we'll just let him talk. And I'm just like I'm just here to s'cause he's

twenty two maybe. I'm like I'm gonna come to the kitchen, have some chocolate milk. You want some potcoal. Yeah. Sit on my lap, too, while you're at it. And like He just talks. And About sixty percent of the stuff that he says is nonsense.

40%. Absolute nonsense. Not just him. Anybody who fits this category, you have to Literally just immediately throw away sixty percent of the words. But when I say to him, I go Michael Most of what you're saying is bullshit and I think you might know it, but look, here's the deal.

Even a blind squirrel finds a nut a nut once in a while. Keep on swinging. You'll hit a home run soon because you're swinging. You're in the game. And I appreciate that about you. And if you ever want to know what you're saying is bullshit, just ask me and I'll tell you. But I'm not gonna call you out. I'm gonna let you get away with it all because I I like I like this gump shit. And he tweeted something the other day that was hilarious. He tweeted Got bad news. Just got back from the chiropractor. They said the chip on my shoulder's permanent. How funny is that? And I was like, this is why you're gonna make something of yourself. Now you might ruin it by saying dub stuff and you're gonna cost yourself a whole lot of money and you're gonna have a lot of headache throughout the years until you learn to be calmer.

But you know he was feeling good about that line too when he tweeted it. Oh you're feeling good But I appreciate that this is a young kid. So I have I have he moved to Austin. I invite him over all the time and I go just talk, man. Just just just Talk. I wanna hear what you gotta say. And he's telling me like and I'm just like learning about what like the younger generation feels about this and that. And he's like, Yeah, we're gonna He's like He has a birthday party coming up on Saturday and we're taking some like new weird version of Uber. I don't even know what it is. Like a party bus company. I don't even know what it is. But he's like, This is what all this is what we're all using. I was like, All right, cool. I'm in. I just want to experience this stuff. So yes, long story short, I totally I am experiencing this where I have young people around me. Sounds weird, but let's get past that. No, the young blood strategy is a real strategy. And uh and actually this is my reminder to myself. I need to refresh my my young bloods are now like

twenty four to twenty five and rich. They like made it. Like okay, so Michael is one example. Um the other guys who set up our initial studios here and then created that uh agency clip. They've th they do over a million dollars a year in revenue off their off their thing and now their their content is going going nuts. Their short form videos are going nuts, like millions of views.

Um And I had to like reprimand reprimand Henry all the time. I was like, hey, Henry, just so you know. You shouldn't talk like this when you're in this meeting or something. And then eventually I was like, you know, I'm not gonna give him advice. I'm just gonna let'em learn. But I saw the same thing where I'm like you're making a bunch of mistakes, but you're taking a ton of swings. You're gonna, you're gonna, you're gonna hit. Uh the g the kid I talked about, Sarouche. uh probably has more money than me now from crypto. The guy has made an absolute killing in crypto over the last few years and so done done incredibly well.

Uh the guy who was my intern to start this podcast. Uh Ishaan who was just like doing the video editing and like created the initial brand name and all that stuff. And did he like invest all of his money into like a short stock, a short position on a penny stock? No, not a short not a short one. He he went all in. He took basically he had like a hundred grand saved up after a couple of years of working for me, and then for for a friend I introduced him to. And he took the hundred grand.

And he just bought Th there was a stock that got delisted on a stock exchange. So all the shareholders were like, damn it, what do we do with this stock that we can't trade anymore? It's like illiquid. And so he bought it all for like Ten cents on the dollar.

being like, I don't know, I still believe. And then that ran up to be worth a few million dollars. Uh his his hundred K basically turned into like a two to five million dollar stake. At that time. Now now I think it's gone down a little bit, but Um There's articles about him in the Australian Post or whatever now. And I'm like, dude, this is crazy. Who and another one, Steve Bartlett.

I hired Steve when I w when he was uh eighteen, nineteen years old, maybe. I maybe that's a little maybe a little maybe he's twenty at the time. Um And I was like this guy again just dripping with swag. And I was like, I just want to be around this guy. This guy's like cool. I don't know. He wears like rings and he like says words I don't know and

Like for some reason he his Tweets go viral. Uh I don't know, uh like Mine don't, so like what does this guy know? And sure enough. ends up creating this social media agency, ends up taking it public.

has this great podcast that's super popular. He's a shark on the shark tank of Europe. Like th this guy's like now he's like he's the black Gary Vee now. And so it's like There's a It's like dude that's I just thought of six in the last fifteen seconds. Like I don't even there might be even more that I'm not even remembering that are like come from this same batch.

And uh I need a I need a new batch. My little personal Y C. This is good that you're talking about this. So I was talking to a friend yesterday. So uh producer Ben, you can leave all this live, but you're gonna have to uh bleep out what I'm about to say, but I want Sean to know what it is.

So um My friend I was talking to He said uh He he just mentioned it cat he we were talking about something totally different and he's like Yeah, you know, like you know, I made thirty million dollars from an angel investment and um

Yeah, yeah, so this is how I found my accountant. I did this, this'cause I was asking him uh for a good accountant. And I was like Like the I made the rewind sound. I was like you know, scratch the record. Reverse. He goes.

Yeah, basically I was uh you know like president of like a smallish startup that wasn't doing so well. And a twenty two year old got kid who worked for me, he quit. to start a company. And I was, you know, frustrated at first, but like he was real promising. And so I invested five thousand dollars. uh at a three million dollar valuation.

The company went public. Like a year or two ago, and it was a fifteen billion dollar valuation. It was called a market cap. It was called h the this is the part you gotta bleep out. It was called You know that company? No.

But okay. It's a boring Nothing special like B to B. Whatever. Um and uh

He he's like, Yeah, I had seventy five thousand dollars at the time. Uh, when I was running my first startup, I didn't have a lot of money, but I decided to invest all of it into startups, and I did it in sizes of ten and twenty five thousand dollars. And that one check that I did of twenty five thousand dollars, it turned into thirty million dollars. Um and And I was like, Are you kidding me? He goes, Yeah, basically like

I knew this kid was strong. And I wanted to be part of just whatever he was in. I wanted to surround myself with young people and I thought he was promising. And uh in fact it it it it worked out really well. And I made so much money off of this one deal. And he goes the and then the other one he said made like a 10 X return as well. And he just got super lucky on that one and it totally worked out.

So it's crazy story. And I'm like, well, I've invested in a bunch of companies. I'm waiting for that to happen. That'd be nice. What what what part do I do for the thirty million? Is there a line for that? Am I in the right line? Yeah, so it worked out. It it's a crazy story. Um That was good. Um all right, I had another one, but let's let's save it for the next uh let's save it for the next episode because it's getting a little long now. All right, that's the pod. I think that was a banger. Uh we forgot to remind people, if you made it this far, there is a gentleman's agreement. This content that you're listening to, it is not free. We're like one of the only places on YouTube actually where the content's not free.

You have to pay. What do you have to pay with? That's your cue, Sean. Oh oh I was enthralled. I was ready for you to just keep going. I thought you were on one. Go ahead. Keep going. You have to pay something in order to listen to this channel. If you've listened to more than one thing. Yeah to do me a favor. Go to the YouTube page and click subscribe because that like helps us. Or you know what?

What I'm gonna ask people to do. If you're listening to this on like Apple or um Spotify, share this. Share it on Twitter, LinkedIn, all that stuff. And and we're even. So you listened to us. I just spent hours on this research, by the way. And you spent

fifteen million dollars of lost money in order to make this content. To tell that story. Yep. I tell that story. I believe in front of you. So uh You've seen my blood subscribe to the channel. Yeah, this is not a this is not this channel is not free.

You have to click subscribe on YouTube because we're trying to build up a YouTube and You have to click. subscribe and follow on the spot podcast. And by the way, what I like, people go in the comments on YouTube and they just say they honored the gentleman's agreement and I go to each one and I just say firm handshakes. Firm handshakes to you. From handshakes to you too. So that's what you have to do. And by the way, I read every comment on those YouTube things.

Alright, we're out of here.

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