Patrick O’Shaughnessy interviews Andrew wilkinson

Patrick: Real privilege of mine to close this. out with a short interview of Andrew Wilkinson. I love finding stories of unusual talent who build something in an unusual way that then becomes the envy of many others, who then attempt to copy, like, sort of the end state of the thing. Um, but I like digging into the, the path that, that led to what Tiny has become today.

So please join me in welcoming Andrew Wilkinson to the stage.[00:01:00] 

Andrew: I just wanted to say to Brent, um, Thank you so much for having Scott ahead of us. It's like having, like, Radiohead play the opener and then Kenny G comes on at the end. This is, this is great. So I'm gonna try and be as good as Scott, but I really doubt I will. So maybe 

Patrick: we just have to work hard to keep it interesting, uh, since we can't compete with that.

What are the five worst kinds of businesses? 

Andrew: I don't know about five. I've got, um, I've invested and started a lot of really terrible businesses. I've started about 15 businesses in my life, and maybe three of them have been successes. And so my story is, I don't know if you guys know, but I was a barista.

One day, these two guys came into the coffee shop and they sat on their laptops drinking espresso. And I kind of asked them, like, don't you guys have jobs? You're here every single day. And they said, we're web designers. And I asked them how that worked. And I realized, hey, I know, I know HTML, I know CSS. I think I can make a website.

And so, I walked into a pulled pork [00:02:00] barbecue joint after work. I pitched the guy who ran it. I said, hey, I'll build you a website for 500 bucks. Um, flash forward 20 years, and now I own a public company with 40 companies. I started a web design agency that was profitable. And I started starting companies.

And I stuck a lot of forks in a lot of electrical sockets. So, I've been through everything from, um, you know, e commerce furniture. I started a cat furniture business. Failed. I started a skin cream business. Failed. I've started, um, a, uh, project management software business. I lost 10 million. Um, Finally, I started a pizza restaurant, which is the hardest business that I've ever been involved in.

And, I think like if you contrast the business I started with, which was metal lab making websites, very simple business and a flowchart, you know, my job is to be charming. Uh, I go and I, I pitched someone [00:03:00] say a startup or something. They say they'll pay me 50 grand for a website. Uh, I just have to find great design talent and engineering talent.

And I, you know, take a spread on that. Very simple. I need the internet. Nerds, keyboards, that's it. Very profitable and simple. And that's what I stumbled my way into, thank God. Doing a restaurant is like going into the gym when you've never lifted weights and trying to deadlift 300 pounds. If you think about how many things have to go right in order just to put a plate of food in front of somebody and, um, you know, someone has to have woken up in the morning and done prep, you have to make sure your service is incredible, it's pristine location.

The ambiance is perfect. Like, just hundreds of different things. And I like businesses, I've realized, that, uh, are very simple. Where there's, like, three steps. I don't like stuff that's complicated like a restaurant. And, by the way, I lost a million dollars doing that. What are the three steps? The three steps to what?

You just said you like things with three steps. Well, so okay. Um, here's an example. We own a [00:04:00] business called we work remotely. It's a job board. Very simple business. Um, people want to hire, uh, remotely. This is, you know, we've had this since 2016 before remote work was a big deal. Um, people post a job on there.

And people apply for those jobs. When you post a job, it's a blue link on a website. We have one developer, two marketing people, simplest business in the world. A couple years ago, that business did four million dollars of EBITDA in one year. 

Patrick: If you thought about, like, the enterprise value of Tiny, and had to attribute it to some skill of yours, and there's many skills that go into, like, buying well and building businesses, like, lots of different skills.

But if you had to sort of stack rank and pick the couple two that you and Chris, you think, shine the most on? What 

what 

Andrew: couple would you pick? Well, I think that we're very good at being normal. So over the years We had all these wonderful businesses and before we started buying them We would constantly have private equity guys showing up at our office and wanting to meet us And they would, you know, we'd do the [00:05:00] initial call and they'd start saying words like A U M and E B D A.

And they'd wear suits. And they're kind of like, you know, they're just weird. They're like lizard people. I don't understand them. They don't, they don't speak my language. They're different from me. They've never run a business. And they always look at my business like a spreadsheet. So they're like, oh, Andrew, um, you know, your OpEx margin on X line, uh, that is 22%.

In another business I looked at, that's 24%. And I'm just like, okay, my business is not a spreadsheet. It's a group of people, and it's really complicated. And so, through going through that experience, Chris and I realized there was a great opportunity. That when you're a founder, and you can speak founder, it's a superpower, right?

I can sit down with someone and say, I know what you're feeling. And I've been through this myself and I can convert all the finance speak, which frankly is kind of bullshit. Like most of these words like EBITDA and all this other stuff, it's just designed to make people feel stupid, right? I felt stupid when people did that to me.

And then when I'd [00:06:00] read the books, I realized, oh, they just mean profit, you know, before tax and other stuff, right? So, um, yeah, I'd say that's, that's the superpower that we've had. If you 

Patrick: think about the, uh, the path that Tiny took, it's very unique, right? Like, it's very different to just, like, fill a holding company with a bunch of cash and then, like, invest it.

You know, that's a fund. Like, that sounds very similar to a fund. Talk about the path dependency. Like, how much of what makes it what it is today is the result of this kind of weird, winding Path that it took it's unusual 

Andrew: origin. Well, it's fine. I mean, you know, like I said, I started out as a barista And I remember when I was a barista, I said I want enough money to buy a six pack I want to wake up whenever I want.

I want to buy a steak dinner pay my rent without worrying Those are my aspirations and you know, it's never enough like I was talking about this in the Q& A earlier You talk to anyone and they always want double and I'm no different. And so I just kept wanting double and the really big inflection [00:07:00] point that we had was going from operators to investors.

When I think about what we were doing in the early days, it was akin to if someone said, okay, I want to get from Seattle to Hawaii by water. And I was going down to the beach. I was grabbing a bunch of buddies who didn't know anything about boats. And I'm saying, hey, let's get 20 logs and we'll zap, you know, we'll zap strap them together.

And we're gonna hit the ocean. We're gonna start paddling. You're probably gonna die, right? That's not a great strategy. And then I read about Warren Buffett. And I was like, oh my god, Warren Buffett finds a cruise ship. And he goes and he buys a ticket on the cruise ship and he rides it to Hawaii. That's so much better.

You know, the ticket is just equity. And so, when I realized that, um, that massively changed everything for us. And we realized that that's business on easy mode. 

Patrick: You told me this story about, uh, a sawmill. Maybe you could retell that story, which I, and I have a 

Andrew: follow up question. Sure. So, um, you know, I love meeting young entrepreneurs.

And I was sitting down [00:08:00] with one of them. And, actually I'll tell another story first. So, I was in Ireland about 12 years ago, and I went to Killorglin, which is in the south, southern tip of Ireland, and the client, uh, at the time, he had sold his business to Getty Images for 300 million. So, you know, in New York, it'd be a pretty big deal, but in Killorglin, Ireland, this guy's the fucking man.

And we are walking through this village, tiny little village of 10, 000 people, and his name is Jerry. And every single person, Hello, Jerry! Oh, Jerry! Like, all the girls are, you know, stroking their hair and stopping to talk with him. And I'm like, this guy is the man. This must feel amazing. And so, we go to the pub, and we start drinking, and I say, like, what is it like?

Like, at this point, my net worth is like, you know, in the hundreds of thousands, or, you know, maybe a million bucks. What's it like to have all this money and admiration and respect? And he goes, I'm drinking the same pint you are, right? [00:09:00] Like, at the end of the day, he's just a normal guy. And, so, um, anyway, I've realized that these, these things are not, um, It just never ends.

It keeps on going and going and going. 

Patrick: But you're not, you don't think of yourself as normal, do you? 

Andrew: No, I think I'm very, very abnormal. I think that whenever I've ever seen someone doing better than me, I'm not competitive in the, like, nasty, aggressive way. I'm competitive in when I see someone doing something that I deem, you know, more advanced than what I'm doing, I just go, how do I reverse engineer this?

I want the cheat codes. I want to learn from them. Befriend them and figure out what they're doing, and then use it for my advantage, not in a harmful way to them. Maybe I'll, 

uh, 

Patrick: tell the quick version of the sawmill thing. Sawmill. Or you 

Andrew: can. I can do it. So, so, so anyway, so. When Jerry said that to me in Ireland, I got distracted there, so when Jerry said that to me in Ireland I was like, that's propaganda, ignore it.

For ten years, I put that out of my head [00:10:00] and you know, I started my business and I got to this scale where I was very abstracted away from the tools and this kid asked me, what's, you know, what's it like? So suddenly I'm Jerry. And I said to him, you know, it's kind of like I like chopping wood. I do it in my backyard because I enjoy it.

It's just relaxing, and I have a wood fire, so I do it after work. And one day a neighbor pokes his head over the fence and says, Hey, I'll pay you 20 bucks. Can you do, uh, can you chop some wood for me? And suddenly my passion, this thing I would already do anyway, Becomes my job, and I'm making money, and I start hiring my friends, and we're going around the neighborhood knocking on doors, we're joking around, we're going out for beer after, it's wonderful.

And then fast forward 15 years, I own a sawmill, a massive industrial complex, I sit in a little air conditioned box doing Excel spreadsheets and email. And I said, that is what it feels like to build a really big business. Your hands are off the [00:11:00] tools. And there's this sadness to it, because When I set out, you know, I never wanted my hands off the tools, but if you're going to succeed, if you're going to scale, if you're going to give your employees opportunity, at the end of the day, you need to delegate to that level of abstraction.

And so I always struggled. Do I admire, you know, Jiro, you guys know Jiro dreams of sushi, the amazing sushi chef, or do I admire the guy who created Chipotle? I don't know. Talking 

Patrick: to the other night, it's clear that like something maybe you can't turn off or have a hard time turning off is seeing a business.

And sort of intuiting how to make it better, how to make margins go up, how to improve marketing, how to do anything, like it's sort of, it just seems like you're very naturally good at that. How do you, how do you balance this like air conditioned room sawmill problem? Because it sounds like maybe that's happened a few times, right?

That like, you've gotten back to the ground level and then you're in the air conditioned room again, which sounds like you probably don't enjoy as much. You even said, like, you'd be in Photoshop designing stuff if it was up to you, your designer. So how do you, [00:12:00] how do you balance, like, your own satisfaction with, like, not wanting double, not wanting to be in the air conditioned room?

This seems like a hard tension, given the natural talent. Well, I 

Andrew: think, I think doing the Buffett thing, being in the air conditioned room, reading all day, thinking all day, It's not a bad way to make money. It's a great day job, but you got to have hobbies. And so I kind of start businesses for fun now. So when I have a, uh, someone asked me this in the Q& A, and we started a couple businesses where there was a problem that we had.

Um, where we just wanted it solved. So, for example, Chris and I, my business partner, when we were running our company day to day, we were ruthless about negotiations. So, we buy a table, we get, you know, four bids from different suppliers, we pit them all against each other, we grind down the margin. Like, we were just, like, coffee, beans, everything.

And We, um, um, we stopped doing that over time. The numbers got big, right? [00:13:00] A million dollars became the number where we started negotiating. Suddenly, then it was five million, then ten million. And so, we stopped paying attention to the little stuff. And so we said, Why don't we create a business that is negotiation as a service?

We'll hire a bunch of professional negotiators. We'll tell all of our companies if they want to use them. You know, send leads there, and these guys will call, and they'll spend three hours grinding a landlord on a lease term, or whatever it is. And we made that business, and we ended up selling it for millions of dollars, didn't want to sell it, but the guy we started it with wanted to.

And so I still get to scratch that itch, the entrepreneurial itch, I still start stuff, but I look at it as my hobby, it's not my day job. 

Patrick: How do you balance the percent of time that is spent on, or what is the percent of time spent on stuff that really Excites you, gives you energy. It's fun is fundamentally 

Andrew: fun.

Yeah, I think that's a really hard question because, um, there's a lot of things like so, for example, um, I was talking to a friend and I told him, you know, [00:14:00] life's not fun right now. Work is not fun and we're in the process of going public and when you're going public, you know, you're signing like. phone book size legal documents that will define your future forever.

There could be some legal liability. Your employee stock options could be, you know, misallocated in some way or something can go wrong. And so, Chris and I were spending all this time with lawyers and, you know, going back and forth on terms and talking to the exchange and all this stuff. I didn't like my life very much at that point.

And the hard part for me is to evaluate. What are the critical things that I need to be involved with? And what do I not? And I think for the most part, other than when we have those freak moments like going public, I am very removed from all that kind of stuff. I'm not doing that many things I don't enjoy, but the problem with running a hold co as it seems like a lot of you guys do, or if you're an investor is if you have enough businesses, there's always a ceo who's pissed off, there's always a [00:15:00] ceo who's leaving.

There's always somebody who is not happy with their comp and wants to negotiate. There's always a deal going sideways. And so, how do you delegate those things? You know, if you're a capital allocator, and you're allocating 50 million dollars, you kind of need to pay attention. Or if the business has 10 million dollars of earnings, you know, you gotta talk to that CEO.

So, I think that's the challenge. And I, you know, I've Talked to Charlie Munger and Warren Buffett, and like, I just don't know how they do it. They seem to say like, oh, I tap dance to work and everything's great. I just don't know how that's possible. 

Patrick: You just bought a business that I think took you a long time to buy where you loved the company.

I want to tell that story, but I also want to understand how often you, whether you care whether or not you love, or how much you care whether or not you love a company that you're buying. 

Andrew: So I'd say almost all of our investments, Or our best investments are driven by passion or deep understanding. So, for example, um, you know, I was an up and coming designer, web designer, [00:16:00] about, you know, 15, 20 years ago.

And there was a social network called Dribbble. And that was where I found a lot of my early work. I hired a lot of my early people. I would always go, as you mentioned, like, seeing every business and looking at the optimization, I'd always think, wow, there's so much more they could do with this. And it was actually started by a guy who I really looked up to in the design community, and we had met at conferences.

And so, I started Dennis the Menacing him. I started emailing him every month. Hey, I know I'm being annoying, but I love your business. Is there any way I can invest? And one day he said, sure. And so when we bought that business, we were able to massively grow it because I knew what the opportunity was because I was a user of that social network.

And so that same thing is true with Aeropress. We own the Aeropress coffee maker company. I was a daily user. I was a barista. It's something I really care about. Um, uh, and then we just bought Letterboxd. I'm a film buff. My happy place is in a darkened theater surrounded by other [00:17:00] people. And so I love when it's stuff I'm passionate about.

We also do buy what I would call, to use the boat analogy, broken down oil tankers that are slowly sinking. Once in a while if they're cheap enough and attractive enough, we will don our scuba deer scuba gear We will buy the tanker for 500k and we will extract 10 million dollars worth of oil, but it's not my favorite 

Patrick: When you find those, how do you find those the the broken down oil tankers?

Andrew: Um, usually it's just some random vc calls us up and says hey, we've got this business Uh, we need to offload and usually they don't value it because venture capitalists I don't know how many of you guys are in vc but Typically you make 20 to 100 bets and you expect that only a few will have these billion dollar outcomes.

And so you don't care about the in between. You don't want to invest in a company that's growing 20 percent a year and profitable. And so often we'll find these businesses where They've raised the crazy [00:18:00] valuations. Um, they've had crazy valuations, or sorry, crazy valuations, huge amounts of capital poured in from VC.

And the venture guys have just backed out. They don't want to back it anymore. Doesn't make sense. And the founder has run it for insane growth. They've pounded cash into it. And so, to them, They're not happy, the founders aren't happy, and we can come in, buy out the venture guys, and just run it like a normal business.

And over and over and over again, we've been able to buy these businesses that lose money and are just not well executed, and just normalize cost. 

Patrick: I thought it was pretty interesting that the range of price measured by like multiple, like even to multiple or something, profit multiple. Um, it's pretty wide, and I'm curious for something like Letterboxd or something else that is much cheaper in a multiple basis.

Do you have heuristics for how you think about The price you're willing to pay in a given 

Andrew: business. Yeah, it sounds really stupid and simple. Um, so I don't think in DCFs, [00:19:00] I'm not that kind of investor. What I think about is, how do I get paid back in five years? If everything goes okay, I want my money back in five years.

And so that means that if I pay 10x, and one of the misconceptions about tiny is that we're cheap, Our first deal, we actually paid 10x for a business. Um, but if I pay 10x, I gotta double the business pretty quick because I want to make my money back in five years. If it's, you know, I buy it at 3x, I just want it not to, not to, to decline too much.

And if I buy it at 5x, nothing needs to happen. Um, and it's very simple. Now, obviously, we hope that, you know, that's the bird in the hand scenario. Two in the bush, you know, and we can kill it. We can, you know, paracels back in two or three years or something, and sometimes that happens. Um, but usually we're shooting for five years.

If I was to 

Patrick: walk around tiny and talk to everyone there that works with you, maybe even the, you know, survey the CEOs or something, and try to get a sense of like the culture of the place and the just like the [00:20:00] personality of the place, how do you think the people would describe it? So is that just you and Chris like, you know, writ 

Andrew: large?

Totally. I would say that our number one priority is hiring humans, not lizard people, right? So, um, you know, we've, our number one screen when we're working with someone or we're buying a company is do they sweat? Do they talk about their family? Are they a normal person? Do they make jokes? Are they somebody that we would want to elevator with and not be too upset about it.

Um, so that's the first thing and you know, generally, everyone at Tiny is kind of nice and down to earth. Um, number two, I think that, what can I say? The radical autonomy. So, I got into business because I Okay, I'll be honest. I had a mom who was very controlling, right? If I was, my mom would always say, Andrew, um, you know, please clean the kitchen.

Why won't you clean the kitchen? And then I would clean the kitchen, and she'd go, Oh, let me do it. And she'd shove me out of the [00:21:00] way. Or she'd say, oh, you know, this dish is still dirty. My mom is a lovely person, but she's, you know, a little complicated, like many people's parents. And so, I think my weird reaction to that was, Nobody can tell me what to do.

And so, I just assume that everybody else feels the same way. And so, with my employees, always, from day one, I've said, show up whenever you want, work as much as you want, uh, total autonomy. Right? Even in an agency, there's no start times, we minimize meetings, um, you know, you don't want to show up on Friday because you're hung over.

That's your prerogative, and we're gonna measure you 100 percent based on output. And so we do that both with employees and also with CEOs. So if a CEO, so when someone joins Tiny, when, you know, we hire a CEO or we have a founder join, we say, you're gonna have to send us monthly financials, and if you want to talk to us, we're here.

And if you don't, that's fine. And so there's CEOs for pretty big companies that we run that I haven't talked to for three years, [00:22:00] some of them. Right? So, very similar to Buffett. We just stole all this stuff from Warren Buffett. And, oddly, I just think that not that many people seem to have the personality where they can allow it.

Whereas, I think I'm a bit lazy. I don't like having to talk to 40 different people and keep their problems in my brain. So, for me, it works really well. 

Patrick: Is there anything that you want Tiny to be, or become, that it's not 

Andrew: yet? No, I don't think so. I mean, I've never, I've never had any success predicting what will make me happy.

Right? Um, you know, I talked to a guy today, Troy, who, somewhere out here, and he said, I'm gonna buy, um, what was it, like a football team or something like that. Right? People have these huge goals and they're working towards something. I've never really had that because I've never been successful at predicting, you know, if you'd asked me that 15 years ago, I'd say I want to win a bunch of design awards or I want to win a, you know, a Webby or I want to be a big, I want to have [00:23:00] Nike as a client and none of those are necessarily things that now I want.

And so. What I've really focused on is staring at my feet, walking, you know, forward. And then every once in a while I look up and I go, Oh my God, I climbed a mountain. And isn't this beautiful? So I'm not really thinking about that. 

Patrick: If you shrunk it down to just like a daily basis, what do you want to do more of?

Like what would make you excited to do 

Andrew: more of? I think it's the thing that gets me the most excited is when I meet a founder. And I connect with them on a personal level and I like them. So I just really, so like, um, you know, I was in New Zealand and I met the founder of Letterboxd and we kind of knew each other.

We'd met at South by Southwest ten years ago. We're both designers and just on a human level, like we weren't I didn't even think I was going to buy the business. I was actually there for a conference. And we just hit it off. We talked about all the people we had in common. We talked about design. We talked about kids.

I like connecting with others and then building a family of interesting people around me. A constellation [00:24:00] of these wonderful people that I get to work with and do things that I'm passionate about. So for me, I actually love buying businesses and that's been one of the sad parts about the last couple years is anyone who's a value investor will know there wasn't that much to do over the last couple years.

So I'm actually excited again for the first time in a couple. 

Patrick: One of the defining things about tiny is your partnership with Chris. Can you describe how and why that's worked for quite a long time? 15 years at least, right? What's 

Andrew: what's behind that? Yeah. So, um, partnerships are like marriage, um, they're really hard.

And Chris and I, we kind of have seasons. So, sometimes we're, uh, totally copacetic and wonderful, other times we're distant, other times we're fighting. And, to be honest, I think the number one thing that's worked is just radical honesty and treating it like a marriage and doing the work. So we actually have gone to couples counseling multiple times.

We follow the John Gottman method for fight resolution. [00:25:00] What's that? Uh, it's basically you let the one, you let the, you know, you say, Hey, you're pissed at me. You explain exactly why I repeat it back. You know, it doesn't matter how mad I am. I can't argue with you. Repeat it back. And then you do the same for me.

And we found oddly that just kind of resolves things for us. And then the other thing is going back to that sense of autonomy. If Chris wants to go off and focus on a part of the company and just have his own little fiefdom for a while, that's fine. And so often we're, you know, Chris is off dealing with WeCommerce and I'm dealing with a different business or something like that.

And so we just kind of come in and out of one another's lives and Changes over time. When you 

Patrick: approach a new business for the first time, and we talked about it a few nights ago, and again, the thing that was so interesting is like how quickly you start to like kind of get your fingers into it and figure it out and figure out how it 

Andrew: could be improved.

I started telling you how to improve your business. Yeah, which, anyway. He has a great business, to be clear. 

Patrick: [00:26:00] Describe that process. Like, what does it feel like, as best you can describe it, to do that? Like, what are you thinking about in that example or another? As you kind of process a business for the first time.

Andrew: Well, I think every business is a machine and when I see a machine, so for example, you know, if you own a sawmill and you spit out a bunch of wood pellets at the end, I would be pretty annoyed if those wood pellets just got picked up and thrown out. So I like the idea of like, hey, can we build a machine to form these into, or sorry, the sawdust.

Can we form the sawdust into wood pellets and sell it to other people? Right? I just love, I don't like inefficiency. I like everything to work well. I mean, I'm the kind of person where I get outraged when I go into a restaurant and I see that they're using 300k bulbs, blue bulbs, right? Just cause the emotion it's gonna give the diners.

It's gonna feel stressful like you're in a Walmart. Like that's how anal retentive and miserable I am.

Patrick: Does it give you, uh, [00:27:00] some sort of pleasure to maximize margins, like, as soon as possible? Or how do you balance that against, like, what might be a different long term decision, like, short versus long term capital allocation within a business with your 5X and, or what was it, money back in five years kind of heuristic in mind?

How do you, how do you think about that? Like, if you have to get your money back, how do you make sure and protect against, like, Making great, you know, internal CapEx decisions or something. Yeah, I 

Andrew: mean, I think you've got to feel good about it, right? So if, if I know that I can charge 5x on my price, So, for example, there's all these businesses that are heavily regulated and you have a monopoly.

And if you can jack up the price, you know, it's like a question of like, well, is that ethical or good or is that the way I want to make my money? I want to make sure that I've Happy customers and happy employees. And I think it's easy to have happy employees, but not have happy customers if you're just jacking up the price all the time.

So I don't like that. [00:28:00] I want to make sure and also in our many of our businesses, their communities or marketplaces and it is so easy to fuck them up. Right? I, I have this model of, um, communities and marketplaces are like airports. So think about an airport. There's one airport in Columbia, Missouri. If you want to get out of here, everyone has to go to the airport, and you're probably going to have to sit there for an hour.

And while you're sitting there for an hour, I can sell you a massage, I can sell you a hot dog, I can sell you a magazine. Um, these social networks we buy, like Letterboxd or Dribbble, there's a lot of people congregating in one spot, and I can sell them a lot of different things. But those things better align with their values.

If I go to, uh, the museum, and I start selling people, you know, super expensive pizza, I might piss them off. They may not like my museum. So I think it's about being respectful. Maybe 

Patrick: as a fun way to close down the conference, you could tell the story of a charming small business that you own, which is the bakery.

Andrew: Sure. Why you did it. Sure. So, um, [00:29:00] when I was growing up, my brother worked at a bakery that was just down the street from where I grew up. So about a block away, there's an Italian deli and bakery and, um, my brother worked there and I was kind of a computer nerd. And so, uh, the owner would always call me in and say, Andrew, look, I'll give you, you know, free croissants if you'll come and repair my computer.

And so I grew up hanging out there and I just loved it. I, and yeah. You know, even as an adult, I would go on a Sunday, listen to a podcast and just have a coffee and sit. I love this place. And about seven years ago, um, the owner said, Hey, would you want to buy this? And I'm going, Oh my God. Like, you know, especially, especially seven years ago, I had no experience in food and beverage other than losing a million dollars, uh, starting a pizza restaurant.

And I really, I really didn't know what to do with it, but I felt like if I don't buy this, maybe someone crappy will buy it. And so, I actually own now four restaurants, and, you know, they're hard businesses, but I [00:30:00] think they're institutional, they're important, and I like the idea of protecting them. So that's another example of my day job is capital allocation, you know, buying these incredible internet businesses, or, or, you know, starting to get into more brick and mortar a little bit.

And then my hobbies are like starting companies, restaurants, I own a news business, like, all that stuff is just for fun. Sorry, 

Patrick: I thought of one more that you mentioned the other night that I think is really interesting, which is Being aware of like scary things on the horizon that might affect a lot of your businesses.

So we're in a really interesting technology time. You just, you spark my memory with a little, little bit more into brick and mortar. So just talk about, you seem like a very optimistic, creative business builder and buyer. But what's, what's the, what's the watching, you know, the horizon piece of what you 

Andrew: do?

Well, so I'm optimistic, but I'm very, very anxious. And I'm always thinking about how everything can go wrong. I mean, Chris would say I'm chicken little. Like, I'm always, for the first like 10 years, I was like, we have to sell. Like, what are we [00:31:00] doing? This is all gonna go away tomorrow. There's no way it can keep going.

That's my default. And I think that's partly why I own 40 businesses. I found that the diversification is never enough. That voice is very hard to, um, to quiet down. So, um, sorry, what was the question? What 

Patrick: you're watching on the horizon that might affect a lot of your 

Andrew: businesses. So, it's really interesting.

I think that investing in technology is like you're building sandcastles on the beach. And the tide is coming in very fast. And so, um, Think about Google. So a year and a half ago, if I'd come to you and said, Google, the most powerful business in the world, one of the largest, um, technology companies, has the most incredible moat in the world, they make insane free cash flow, those guys are, you know, their search business is actually under assault.

You'd be like, good fucking luck. There's no way. Now, I haven't used Google in three months. I use ChatGPT exclusively. Now, we can argue all day whether Google's moat is actually eroded, or [00:32:00] they'll be fine, but you can't predict that. And that's the best technology business in the world. And so, I think what's a little bit interesting for us is, uh, and partly why it's so important that we underwrite to five years, is because you really can't predict how long a technology moat will exist.

And so, that's one reason that we're thinking about brick and mortar, um, and just being very careful about underwriting technology. 

Patrick: Andrew, thanks so much for your time. Thanks, Patrick.

This transcript was generated with Descript AI

Previous
Previous

How to Hire | Tim Ludwig

Next
Next

What I Wish I’d Known Before Getting Into Small Businesses | Trish Higgins