30 March 2023

Trey chats with billionaire entrepreneur and investor, Mr. Andrew Wilkinson. They discuss various topics, including self-care and parenting, as well as exciting deals he collaborated on with Bill Ackman and Howard Marks.

Andrew is the co-founder of Tiny, which has been called the Berkshire Hathaway of Tech companies. Andrew turned his first business, MetaLab, into a not-so-tiny conglomerate in a similar fashion to how Buffett turned an old textile mill into the juggernaut Berkshire is today.

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  • The philosophies behind Tiny and how it operates.
  • How he partnered up with Bill Ackman and Howard Marks on some exciting deals.
  • Andrew’s insights from his conversations with Warren Buffett and Charlie Munger.
  • What it means to set “Anti-goals”.
  • Andrew’s thoughts on parenting, philanthropy, entrepreneurship, investing and a TON of amazing resources.


Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off-timestamps may be present due to platform differences.

[00:00:00] Trey Lockerbie: My guest today is Billionaire, entrepreneur and Investor, Mr. Andrew Wilkinson. Andrew is the co-founder of Tiny, which has been referred to as the Berkshire Hathaway for tech companies. Andrew turned his first business Me Lab into a not so tiny conglomerate in a similar fashion to how Buffett turned an old textile mill into the juggernaut Berkshire is today.

[00:00:24] Trey Lockerbie: It is truly remarkable what Andrew has, Bill and is building, and we touch on a wide range of topics. In this episode, you’ll learn the philosophies behind Tiny and how it operates. Andrew’s insights from his conversations with Warren Buffet and Charlie Munger, how he partnered up with Bill Ackman and Howard Marks on some exciting deals, the art and science of self-care, de-stressing and delegation, what it means to set anti-goals, Andrew’s thoughts on parenting, philanthropy, entrepreneurship, investing, and a ton of amazing resources, most of which I  was unfamiliar with. All of that and a lot more.

[00:01:04] Trey Lockerbie: Andrew is one of the clearest thinkers I’ve chatted with in recent memory. He’s extremely thoughtful and intentional with how he runs his life, his health, and his businesses. There is a lot to learn from this one. So without further ado, please enjoy this conversation with Andrew Wilkinson.

[00:01:23] Intro: You are listening to The Investor’s Podcast, where we study the financial markets and read the books that influence self-made billionaires the most. We keep you informed and prepared for the unexpected.

[00:01:35] Trey Lockerbie: Welcome to the Investors Podcast. I’m your host Trey Lockerbie, and like I said at the top, I am here with Andrew Wilkinson. Andrew, this has been a long time coming. I’ve wanted to do this interview for a while, so I’m really happy to have you on the show. Thanks for coming on.

[00:01:57] Andrew Wilkinson: Thanks, Trey. It’s great to be here.

[00:01:58] Andrew Wilkinson: I’ve actually been listening for years, so it’s really cool to be on. 

[00:02:02] Trey Lockerbie: I wanted to kick things off with a little bit of your view of the markets, only because there’s a lot of noise happening all around us. Banks are starting to fail here in the US over in Europe, etc., etc. This environment where funding has become scarce, valuations are declining, interest rates are going up.

[00:02:25] Trey Lockerbie: I was just thinking to myself, I imagine someone like you might be one of the few who are currently on offense, right? Because these kind of scenarios might create opportunities or businesses that you’ve been looking at for a while become attractive, all of a sudden are either affordable or potentially illiquid and needing help.

[00:02:47] Trey Lockerbie: So as an acquirer, is this something that you are kind of viewing as, not a positive, let’s say, but opportunistic in some degree for this

[00:02:57] Andrew Wilkinson: Yeah, I mean, we really have long periods of inaction, so in many ways for the last two or three years, with a few exceptions, we’ve mostly been sitting on our hands.

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[00:03:07] Andrew Wilkinson: And the beauty of my business is that at the end of the day, I don’t have a ticker for every individual business. I own about 30, 30 plus companies. I don’t know what each of them is valued other than whatever. Chris and I kind of do math in our head, and so we don’t get caught up in the macro. We mostly just focus on the micro, and at the end of the day, we examine every individual business and…

[00:03:32] Andrew Wilkinson: Each business has some kind of competitive advantage or something that we like about it. And so we’re quite happy just to hold the business. We can’t panic, sell and freak out as someone would traditionally with a stock portfolio or something like that. And I think that’s been wonderful for us.

[00:03:49] Andrew Wilkinson: I always, whenever I talk to friends about this, I always say, okay, what’s your biggest investment? And invariably they’ll say, unless they’re a professional investor, that it’s their house. And I say, okay, well your house goes up in value and it goes down in value depending on what’s going on in the market. But you don’t see it every day. You never panic sell your house. You know, you’re not counting your eggs before they hatch. You might have a rough sense that it’s gone up or down, but you know, it’s not down to the penny. And so I think that’s one of the nice things about owning a lot of different businesses is you don’t have tickers like that.

[00:04:38] Andrew Wilkinson: So yeah, we’re just kind of sitting and waiting and getting excited to start buying businesses again. Which we really haven’t done much of for the last couple of years.

[00:04:50] Trey Lockerbie: For those who don’t know, you’re building what many have considered to be the Berkshire Hathaway for tech, and that may or may [00:05:00] not be evolving to different sectors, but I know that’s kind of how it originated.

[00:05:05] Trey Lockerbie: Using this analogy, what is your source of float? Is it simply the cash flows from the underlying portfolio companies? Because I imagine a lot of companies who are relying on funding, as we kind of alluded to earlier, are running into trouble, whereas your companies hopefully are cashflow positive and positioning you guys well to potentially pursue more acquisitions.

[00:05:29] Andrew Wilkinson: Yeah, I mean, with a few exceptions, almost every business that we have ever acquired or operated has been profitable. And we started out that way, not because we set out to be bootstraps, but because we knew no other way. So when I started my business, I was in Canada. I didn’t know what a venture capitalist was. I couldn’t have gotten a bank loan if I tried. And so at the end [00:06:00] of the day, I had to bring in more revenue than my expenses.

[00:06:04] Andrew Wilkinson: In the early days, I barely understood accounting. But what I did understand was that if my bank account balance was larger on day 30 than on the first of the month, things were going well. And so that was where we started almost 20 years ago. And we followed that thread.

[00:06:26] Andrew Wilkinson: What ended up happening was we built quite a few bootstrapped, highly profitable businesses, but we always thought our businesses were terrible. Every business internally, as a dumpster fire knife fight where you’re just trying to stay alive. And over time, as we got to know more and more business owners, we realized that many of them actually were just not operating with best practices. They weren’t operating with the same discipline that we had learned out of necessity.

[00:06:57] Andrew Wilkinson: As we started seeing those businesses, we realized a lot of those founders were exhausted or they wanted to sell their business, and so we would buy them and really just implement those best practices, hire a CEO, and have the baton pass to.

[00:07:15] Trey Lockerbie: I want to touch on that bootstrapping history of yours, because I’m curious if there are downsides to that. I saw a tweet from our friend Alex over at Morning Brew the other day, and he said, scrappiness is a gift and a curse. So it’s a gift because you learn every skill before you delegate it. It forces you to default to an action mindset.

[00:07:34] Trey Lockerbie: You can stretch every dollar, but it’s a curse because it creates a scarcity mindset, which is not often helpful. You risk taking on low leverage tasks and you feel every part of the emotional rollercoaster. I dunno if that last part goes away at any point, but the risk of taking low leverage tasks is something I really resonated with when I saw that.

[00:07:52] Trey Lockerbie: It’s hard to be strategic sometimes when you’re so reactive on the bootstrapping path. So I’m curious, how did you grow out of that? How did [00:08:00] you learn? Get beyond maybe the limitations of bootstrapping. 

[00:08:05] Andrew Wilkinson: A lot of really disastrous hiring and a lot of really sleepless nights and a lot of misery. To be honest,

[00:08:11] Andrew Wilkinson: The way I think about this is like if you own a bakery, and let’s say that you’re the number one place in Los Angeles selling croissants, and there’s a line down the block and you have one oven and you need to go and spend $200,000 to buy another oven in order to actually be able to service your customer.

[00:08:31] Andrew Wilkinson: But you’re capital constrained. Of course, it’s logical in that world to go to the bank or to go to an investor to buy another oven because you have excess demand and you need to keep your customer happy and you know you can maximize the business that way. I think everybody understands that, but I see a lot of it.

[00:08:50] Andrew Wilkinson: Tech entrepreneurs who have that same situation, they have the line down the block and they just won’t deploy the capital required to serve the customer or to maximize the business, usually out of fear. People get into this mindset and I used to have this mindset of I need to own a hundred percent of the pie.

[00:09:08] Andrew Wilkinson: It’s not worth giving up 5% because I can’t have anyone else in the business or that creates a risk or something like that. But I think it’s very logical to have a slightly smaller slice of pie in order to have a larger pie in the long run. And so what I ended up realizing over time, Was that I was limiting my businesses by not investing in r and d, not buying capital assets, that kind of thing.

[00:09:33] Andrew Wilkinson: And we kind of came to this realization over time, it’s a lot easier when you’re at scale. So for example, when you own five businesses and you have one that has a big opportunity where there’s a lever you can pull to five exit, it’s a lot easier to do that when it’s one of five eggs. But when it’s your only egg, it is terrifying.

[00:09:54] Andrew Wilkinson: And I was sitting in a board meeting with a SaaS software business that I’m a large investor  in a couple years ago. And I remember talking to the founder and he said, oh, we’re doing really well with paper per click on Google. And I looked at the p and l and they were spending $10,000 a. And they were getting a $20,000 payback within a month or two.

[00:10:13] Andrew Wilkinson: And I said, well, why are you only spending $10,000 a month? And he said, well, because that’s what we budgeted for it. That was their kind of conservative thing. And I was like, Hey look there’s a hundred dollars bills lying on the ground. You need to pick up as many as possible. But for some reason that conservatism, that bootstrapper mentality held them back from doing that.

[00:10:33] Andrew Wilkinson: And so we see a lot of that and I really empathize with it because I’ve been there. I think bootstrapping is a bit of a blessing and a curse, but I’ve been surprised by how big some of our bootstrap businesses have been able to become with very minimal reinvestment. 

[00:10:49] Trey Lockerbie: Another company that’s been a huge success for you is WeCommerce and there is a merger underway where Tiny and We Commerce will now both be public and  Howard Marks and Bill Ackman and some other folks are somehow in the mix here.

[00:11:03] Trey Lockerbie: And I’d like to kind of talk through why the move to merge and go public and how you got investors like the titans of industry behind you on this move. 

[00:11:14] Andrew Wilkinson: Yeah, well, the story actually goes back to about 2010. So at the time, I was running MetaLab, my original agency. I was experimenting, incubating a few SaaS software businesses, and other stuff, and I was at a conference when I met Harley Finklestein, who is now the CEO of Shopify. At the time, Shopify was just this tiny little Canadian software company doing e-commerce. He said, “Hey, we need someone to build themes.” They wanted an easy way for merchants to sign up and then select the theme. For example, let’s say you’re an electronics manufacturer, and you want to sell online, you’ll want a different template than somebody who’s selling a skin [00:12:00] cream.

[00:12:00] Andrew Wilkinson: And so we would create a variety of templates and sell them in the Shopify marketplace. We were their first partner in their theme marketplace, and that ended up turning into a wonderful business. We would build a theme in a matter of months, and we could sell it for years. It’s a digital good, very high margin, and our only cost is really maintenance and updating it, doing bug fixes, and then doing support. So that business took off, and in 2014, I received an offer to sell that business. At the time, I was not an investor. I didn’t really understand finance in a major way, and so I ended up selling what was really an exceptional business with a huge tailwind. This was the kind of dominant theme seller on the Shopify platform.

[00:12:54] Andrew Wilkinson: And Shopify was growing at a wild clip and had just gone public, [00:13:00] but I ended up selling the business, and for the first time, I had this large sum of money. I had millions of dollars in my bank account, and I decided I needed to read a book, you know, about investing. I needed to finally figure that out. And the first book that I picked up was The Warren Buffett Way. And as soon as I read that book, I realized, oh my God, I’ve made a mistake. I shouldn’t have sold this wonderful business, but I still own 20% of it. I stayed on the board and I used the knowledge that I learned from Buffett to start Tiny, and I continued to follow along with that business as it grew. And the folks that we had sold it to, they were a family office and they decided that they wanted to sell. And so I said, okay, well, can I buy it? And so we ended up buying back the business, and I had met Bill and Howard in passing over the prior years. And at one point, Bill kind of pulled me aside and said, Hey, if you ever want to do a deal, I would love to partner with you. And having been a bootstrapper and having never raised money, I figured, hey, this is an interesting experiment, a great way to work with someone that I really respect and try raising capital. And so we did that with Bill and Howard and a handful of other investors, and we ended up buying more businesses within that platform.

[00:14:44] Andrew Wilkinson: And then we took it public in 2021. And that business is still a public company. And over the last year, Chris and I meanwhile had built this very significant portfolio of other businesses and we decided that we wanted to take that public. And so we thought, Hey, what better way to do so than to merge into e-commerce and have a single stock where we can allocate capital across all the different entities in one place.

[00:15:11] Andrew Wilkinson: And so we just announced that merger about a month ago. 

[00:15:15] Trey Lockerbie: Congratulations on that. It’s very exciting. The Buffet book is interesting, for obvious reasons. He’s one of my big references and I know that we both study him and there’s a lot about Tiny that resembles Berkshire. But something that stood out to me that may or may not resemble Berkshire in a way is that tiny seems to be almost agnostic to existing management when you’re looking at acquiring a company and you seem pretty confident in the idea of placing a proper leader at the helm if you need to.

[00:15:42] Trey Lockerbie: And I’m curious, how many, or have you found many founders that can make the transition from leading what they call pirates to sailors? Right. Or do you find that it’s often best to find a more seasoned person to put in place to run a much larger operation and maybe best not to leave it to the  founders?

[00:16:01] Andrew Wilkinson: Well, I’d say there’s really no rules. There’s only experience. I think for myself, I realized pretty quickly that I was a great zero to one person. I loved starting things, but, and I really loved operating at large scale, but I didn’t like the in between. And for me personally, I actually didn’t like managing large groups of people.

[00:16:23] Andrew Wilkinson: I loved managing a 20 person company, but I don’t really enjoy managing a hundred or a thousand person company. And so it was much better for me to hire CEOs who enjoyed that phase of growth and operations. I often think about a business like, just to use an example, Chipotle.

[00:16:39] Andrew Wilkinson: So if you think somebody invented the burrito, right? That was one person, another person came up with the concept of a fast casual burrito joint that was the founder of Chipotle. Somebody else scaled or he scaled it to five locations or something like that.

[00:16:56] Andrew Wilkinson: And then he likely brought on a president or CEO who had experience in fast food, who took it to a hundred locations and then perhaps handed the baton to somebody else who took it to a thousand locations. And I think each of those baton passes, each of those different CEOs or leaders is a different skill set.

[00:17:13] Andrew Wilkinson: Now, are there exceptions to the rule like Bill Gates or Mark Zuckerberg? Absolutely, but I think they’re few and far between. And if you look at someone like Mark Zucker. He still hired Cheryl Sandberg, who is an experienced executive who had scaled a very similar business at Google and had basically already done it.

[00:17:32] Andrew Wilkinson: And so effectively what we tell founders is that if they want to stay on, they’re absolutely welcome to and will leave them alone. And they can keep operating the business as long as they like with minimal interference. Some of those founders want us to help. They’ll say, Hey, I really need a COO, a CFO new team member, and we’ll help them with that.

[00:17:53] Andrew Wilkinson: But a lot of the time they’ll just say, Hey I just want to keep running my business and I want to go with you guys because you’re [00:18:00] easy to deal with and you leave me alone. Then there’s other founders who just want to sail off into the sunset. They want the easiest deal ever. 30 day, 30 day deal cash in the bank on day 31 payment sign the documents and you’re done with a little transition period.

[00:18:15] Andrew Wilkinson: And we do both. So we have really great experiences with some founders who have stayed on, grown their business significantly, and then we’ve also brought in CEOs to run the business. And typically the way we think about that is just we want to find somebody who’s done it before. So, like I said with the burrito example, if I have a 50 location, fast casual business, I want to find someone who’s grown a similar business from 50 locations to 200 locations with similar values.

[00:18:48] Andrew Wilkinson: And so we basically find people like that. We plug them in and we leave them to it. 

[00:18:53] Trey Lockerbie: That quick 30 day deal is super interesting to me because one thing I’ve really admired about Buffet over the years are how he [00:19:00] simplifies almost everything and it’s, there’s a certain beauty to that. And I know that he’s done a few deals just over a handshake and you seem to follow the same sort of, I guess, philosophy.

[00:19:09] Trey Lockerbie: So I’m curious how you really ultimately decided to do that and how hard it might actually be to do that. Because while it all sounds very simple, that’s a lot of work probably in a very short period of time, a lot of hard, big decisions to make pretty quickly. So maybe walk us through what a 30 day deal really looks like.

[00:19:26] Andrew Wilkinson: So I’d say there’s no set timeline. At the end of the day, the founder is the one who sets that. If somebody comes to us and they say, look, I’ve got an incredible deal. Here’s everything you need to know. I want to transact in two weeks. My lawyers already drafted the purchase and sale. Here you go. We could totally get that done if we love the business and we love the person.

[00:19:50] Andrew Wilkinson: And then at the same time, often the founder has advisors, they have a lawyer. The lawyer really wants to dial everything in. Sometimes that takes three to six  months. So there’s really no rhyme or reason. Sometimes they take a long time. Sometimes they go really quick and we don’t pressure people to close in 30 days.

[00:20:08] Andrew Wilkinson: It’s more kind of an indication that if they’re comfortable and they want to move quickly, we can do that. From my perspective, you can’t do a good deal with a bad person. And if you need a contract and you have to rely on it. , that’s not a good sign. So we do have a general counsel and obviously we draft all the requisite contracts and that kind of stuff.

[00:20:29] Andrew Wilkinson: But at the end of the day, if somebody is going to defraud you or something like that’s going to happen regardless of a contract. And a contract. You know it, it gives you legal protections, but you have to go to court. It takes, it’s a five year process. So, to be honest while we do all that stuff, I’m really trying to examine the quality of the person and do a lot of qualitative analysis of this person.

[00:20:52] Andrew Wilkinson: Are they authentic? Are they nervous? Do we have friends in common? What’s their pattern of behavior in the past? Do we trust them? Would we let them babysit our kids? There’s a lot of these kinds of qualitative checklists that we go through and yeah, that’s how we’re assessing people in terms of these deals.

[00:21:10] Trey Lockerbie: In my recent conversation with Christoph Goche, he highlighted a study that showed that people are incentivized by remuneration, but more motivated by equitable remuneration. So in other words, people essentially weigh being paid fairly more than the actual wage itself. From your experiences, what have you learned about incentivizing and motivating so that you can increase delegation?

[00:21:35] Trey Lockerbie: Going back to this Berkshire model. 

[00:21:38] Andrew Wilkinson: So I used to in the early days of my agency business, I had this feeling like, why am I the only one that cares? Or why am I the only one that’s excited? And I think that. People obviously work for the work. There’s people that are intrinsically motivated that love what they do, but at the end of the day, if you are winning, I think everybody  needs to win together.

[00:22:01] Andrew Wilkinson: And so we found that as soon as we actually figured out incentives, we started bonusing people in line with the numbers that we cared about. So for example, free cash flow or net profit or EBITDA or whatever makes sense in that particular situation, that alignment of incentives, as long as the employee or C E O understood how they won, had some control over those numbers and understood the numbers, we found that people all pull together and achieve whatever needs to get done to hit those numbers.

[00:22:31] Andrew Wilkinson: And so that’s worked really well for us. And we try to ensure that we don’t have any kind of lottery ticket incentives. So if the quarter doesn’t get hit perfectly, they’re still getting paid, right? We don’t want somebody to be dejected and punished by rewards. 

[00:22:46] Trey Lockerbie: Can you say more about that? I’m curious about the lottery system there.

[00:22:51] Andrew Wilkinson: Well, so for example, let’s say your stock price is $20 and you issue and employ a hundred thousand dollars of stock options. And then the business let’s say the stock price drops to $15. Suddenly that employee went from being in the money on their options to their options being worth absolutely zero.

[00:23:10] Andrew Wilkinson: It’s completely binary. Whereas an owner they would’ve gotten, they would have the equity at $20. Their equity would become worth a little bit less as it dropped 15, but they would still care. They’d still have something to lose. And so we try as much as possible, avoid those kinds of lottery ticket incentives.

[00:23:29] Trey Lockerbie: Very interesting. So buffet and delegation seem to go hand in hand. He apparently, we were talking about before how we’re kind of still curious in scratching our heads how he lives this very stress-free life and has nothing on his calendar and apparently doesn’t do email. So from what I’ve learned about you from some of the other interviews you’ve done, is that the latter is a bit of a struggle or still a struggle, and I think for most of us it is.

[00:23:51] Trey Lockerbie: So it’s not just you. I relate. What has worked and what hasn’t worked for simplifying your life and trying to de-stress it  as you continue to delegate. 

[00:24:02] Andrew Wilkinson: Well, ultimately, the number one thing that’s worked for me has been taking every single piece of responsibility for a subsidiary business. And it shrinks somebody who’s responsible for it.

[00:24:14] Andrew Wilkinson: At the end of the day, there’s no way I could keep all the businesses in my head. And so I have to rely on a wonderful group of CEOs to operate those businesses. And so that covers off most of the. Day-to-day fires, right? When I was running my agency, I would get a phone call every day saying, oh, this client won’t pay us and this employee is quitting, and each of those required an actual next action.

[00:24:38] Andrew Wilkinson: I had to immediately respond to the client and get on a phone call or whatever. My problems now are much more high level, like, it’s kind of like are we going to buy this business or not? And I’ve got 30 days to decide are we going to restructure our debt into an X or Y facility?

[00:24:56] Andrew Wilkinson: And there’s a lot of time for analysis, so it’s much slower.  That said, I still, as you mentioned, struggle to not have a full calendar, an email. And to be honest, I don’t know how Buffett does it. I think that, I mean it’s, I think it’s real. So I once got an introduction to Buffet via email. And I got a response from his assistant the next morning and it just said, Mr. Buffett’s in his office, here’s the number to call him right now. And he immediately picked up and he talked to me for an hour and a half. And I don’t understand how that happened or why he decided to make time for some random kid in Canada. But he seems to be pulling it off. And I don’t know what the secret to that is.

[00:25:38] Andrew Wilkinson: Maybe it’s not doing email. From my perspective I’ve tried a lot of different stuff. I have an assistant who reviews all my emails and flags the most critical ones. So if I don’t want to look at email, I can just look at the three or four that are kind of. Burning or time sensitive. But I struggle with this like anybody else.

[00:25:56] Andrew Wilkinson: And I always joke I’m tough on tasks. If there’s [00:26:00] anything that comes to me, I’m allergic to it. I want to delegate it. But I still somehow manage to have a lot of stuff to do.

[00:26:07] Trey Lockerbie: Can you tell us more about that call? I mean, you had a little bit of time maybe to prep, but you knew you, you had to call right now, it sounded like.

[00:26:12] Trey Lockerbie: So there wasn’t a lot of time to think what was going through your mind and what questions maybe were you able to ask Buffet that you were maybe hoping to and were you surprised by anything he said in response? 

[00:26:23] Andrew Wilkinson: I think there’s that whole idea of not wanting to meet your heroes because they’ll let you down.

[00:26:28] Andrew Wilkinson: And Buffet Absolutely did not. I’ve met both Charlie Munger and Warren Buffet now, and he was just so high. I was struck by how high his EQ was. How he really listened. He mirrored back. He clearly was listening to what I was saying. He asked a lot of really great questions and I got the sense he was talking to a lot of old people and they’re not, they’re not aware of you.

[00:26:53] Andrew Wilkinson: They’re not really kind of digging into what you want to talk about. It’s just them talking about whatever they want to talk about. [00:27:00] And I felt that he, yeah, really took the time to see me and understand me and ask really good questions. And I got to ask him a lot of questions, primarily around raising children and money and philanthropy.

[00:27:10] Andrew Wilkinson: That was fascinating. But the interesting thing about Buffet is that he’s very public with his opinions. And if you’ve listened to all of his public interviews and you’ve read all of his letters, you pretty much know what he’s going to say on any topic. Munger, I find. So if Buffet is like classic rock, you can kind of know how it’s going to go.

[00:27:31] Andrew Wilkinson: Or 12 bar blues. Munger is like jazz; he’ll just spout off about any topic. You never know what he is going tosay. I mean, if you’ve seen the Daily Journal, annual general meeting, you’ll know this. Right? You never know what he’s going to say next. And it’s fascinating. But I’ve really enjoyed talking to both of ’em.

[00:27:50] Trey Lockerbie: One of Buffett’s quotes about raising kids that I’ve come across is that he wants to leave them enough to do something, but not enough to do nothing. You’re now wealthy individual raising parents and what have you, what philosophies have you crabbed on to, either from Buffett or others that have helped direct you with raising your own kids?

[00:28:07] Andrew Wilkinson: I think it’s really challenging, and to be honest, I haven’t really come to a conclusion at this point. My kids are five and three, and I imagine if you are, you come from a long line of farmers and you are the generation that created a large industrial farm that can feed an entire town, is it logical for you as someone in a farming family to then go teach your kids how to grow root vegetables?

[00:28:38] Andrew Wilkinson: Or is it better to say, “Hey, here’s how you can run this large business,” or “here, help me give away the money to everyone in the town,” or “hey, go play violin and study philosophy,” or should I say, “Hey, all this is mine. You go start your own farm from scratch.”

[00:28:59] Andrew Wilkinson: And I think every single one of those has a pitfall, and I don’t really know what I’m gonna do yet. I’m still trying to figure that out, but I’m trying to explain it to my kids. I think that one of the mistakes that I’ve heard is not talking about wealth, not exposing them to it, not helping them understand it.

[00:29:24] Andrew Wilkinson: So I’m as best I can with a five-year-old, I’m trying to explain all the different businesses I own and how we make money. And whenever we go to a cafe and we buy something, I try to explain what came outta my bank account and what we walk through, how I made the money. But yeah, it’s a really hard decision and it has pretty serious consequences.

[00:29:44] Trey Lockerbie: One thing I’m really curious about is how you’re thinking about teaching them about investing, because you mentioned earlier you kind of had a windfall at one point and you said, okay, what do I do with this? You went and bought a buffet book and curious about maybe how you’re thinking about starting someone out earlier than maybe 

[00:29:59] Trey Lockerbie: you did.

[00:30:00] Trey Lockerbie: Well, I think that everything I’ve ever become passionate about, I was just slapped in the face by, or there was a really important reason why I wanted it. So when it came to investing or starting businesses, I grew up in a family where we didn’t have a lot of money. We weren’t super poor, but money was always a really tense topic in our house.

[00:30:22] Trey Lockerbie: My parents were in a lot of debt. My dad’s business was failing, and so I just didn’t want everyone to be stressed out. And so I always told myself that I was going to make a lot of money so that I wouldn’t have to deal with that anxiety. So that’s what fueled me starting businesses and getting into investing really out of fear.

[00:30:43] Trey Lockerbie: In the same vein, I never wanted to play a musical instrument. My mom would try and set me up with piano lessons or singing or any of that stuff, and I just didn’t see why I should care. And then I had pressure on a girl and she really liked this guy who played guitar. and I was like, oh my God, I need to  learn guitar.

[00:31:00] Trey Lockerbie: So I taught myself guitar really quickly to try and impress this girl. Of course it didn’t work, but I had an incentive to do so. And with my kids I really don’t want to pressure them into getting into investing. I’d rather that maybe I talk about it passively or they just notice that I have all those books and one day they crack one.

[00:31:22] Trey Lockerbie: Or I take them to a Berkshire AGM or something and see if it resonates with them. But I really don’t want to push it on them. And I think that at the end of the day, they need to find their own passions and get obsessed with something. And that’s going to have to happen naturally. 

[00:31:37] Trey Lockerbie: That monger quote.

[00:31:37] Trey Lockerbie: Right? Show me an incentive. I’ll show you a result that comes to mind. There’s another Munger quote that comes to mind too, which is attributed to Munger. Often I don’t, not sure if it’s something he picked up, but it’s, all I want to do is know where I’m going to die, so that I never go there. And with this in mind, everyone’s familiar with this idea of goal setting, and that seems to be a big problem.

[00:31:56] Trey Lockerbie: Part of what it takes to become successful, but I know that you and  your partner have developed a practice that you call anti goals. So can you talk to us about what an anti goals is and how you go about doing something like that? 

[00:32:10] Andrew Wilkinson: Yes, we read that Munger quote and it really resonated. And a couple years ago, Chris and I were feeling really unhappy.

[00:32:17] Andrew Wilkinson: On paper we were very successful financially. We had wonderful businesses, we had a lot of freedom on paper. But our actual day-to-day lives were really stressful. And so we started kind of looking around. and saying what actually makes us miserable? It’s really hard to think about what’s going to make you happy.

[00:32:36] Andrew Wilkinson: You might go, oh, when I have a Ferrari and a mansion and a private chat, I’ll be happy. But in reality it’s hard to predict. But you know for sure that you don’t like being really tired, overbooked on your calendar in a back to back meetings and phone calls, a lot of business travel, et cetera.

[00:32:55] Andrew Wilkinson: And so we made this list of anti goals of things we didn’t want to do, and then we kind of reverse engineered it from there. And that was very instructive for us in terms of hiring. So who could we hire? For example, let’s say that Chris was spending a lot of time with our banking relationships. Who could we hire to go and do that for us?

[00:33:15] Andrew Wilkinson: And then finding someone who loves doing the banking relationships will do a better job than Chris, and in doing so, we’ll free us up to not have to do the things that we hate. So we found that very instructive. I actually wrote a medium post. If you search the Power of Antigo on Google, it should come up as the first result.

[00:33:31] Trey Lockerbie: So as Carl’s icon is known to say your valuation, my terms, and a lot of people think of acquisition simply, it’s just the price, but there’s a lot more to it than that. And the structure of a deal is almost just as important. So a lot of nuance can go into a deal, but I’m more curious about where you started, how you refined your approach, and what resources you use to kind of educate yourself on how to create deal structures.

[00:33:56] Andrew Wilkinson: Well we were really country bumpkins, like we had no clue whatsoever. Chris and I were really good operators. We knew how to read a financial statement, but we didn’t know anything about deal terms or structures or cap tables or anything else. And so in the early days I, the way I kind of think about it or thought about it in the early days, and I still kind of think about it, is if I buy this business, how do I pay myself back in five years?

[00:34:21] Andrew Wilkinson: So that can be, I pay five times earnings, right? And the business just stays flat. Pay myself back in five years. Let’s say that I pay 10 times earnings. Let’s say it’s a business that’s growing a little faster, I’ve gotta double the earnings. Well, how hard is that going tobe? What levers can be pulled?

[00:34:38] Andrew Wilkinson: So, for example, when we bought Dribble, which is our social network for designers, we looked at the business and we said, okay, we’re going to pay, I think we paid about 10 times earnings for the business, and we identified two or three kind of low hanging fruit opportunities within the business where we were confident that in the first two years we could pull those levers  and that we could double the earnings.

[00:35:02] Andrew Wilkinson: And so that’s kind of how we think about it to this day. So even if I’m paying 20 x, I’m still thinking about whether I can grow the earnings appropriately to get to the point where I can pay myself back in five years if I was cash flowing the business. 

[00:35:17] Trey Lockerbie: I noticed that there’s, I think you’re under what, 30 fully owned companies now and there’s something like 90 that you’re a minority investor in.

[00:35:23] Trey Lockerbie: Is there often a path where the minorities are something that ultimately become majority or the minorities have bigger pies already that you’re just wanting to ride along with? 

[00:35:33] Andrew Wilkinson: Well, it’s interesting, so being an entrepreneur, I have a lot of entrepreneur friends and they often start companies. And so as they’ve started companies they’ll come to me and say, Hey, I’m raising money for my company.

[00:35:46] Andrew Wilkinson: And we’ll throw in 50 or a hundred grand. And I kind of look at it as roulette chips. It’s not our primary business. It’s fun. We get to engage with great entrepreneurs and we put down a whole bunch of chips and now, and then we win. [00:36:00] I think we’re up at least on paper we’re up a reasonable amount and it’s fine and it gives us some market intelligence.

[00:36:06] Andrew Wilkinson: We get to see kind of what’s happening in the startup world. And occasionally we will buy a majority stake or buy one of the startups. That’s quite rare. I’d say that’s probably. One in 50 that we’ll follow on or buy majority in our core business is buying majority stakes in cash flowing businesses.

[00:36:24] Andrew Wilkinson: And I think that’s like playing poker. You actually have an advantage and skill matters. So that’s the primary focus and I think it’s like 97% of our capital or something. I’m making that number up, but it’s something very significant that’s in the majority of deals. And it’s the venture stuff that is a very small percentage of what we do.

[00:36:45] Trey Lockerbie: I know Buffet does this and Tom Gainer introduced me to it as well. They’ll sometimes own tiny little pieces of hundreds of companies and it’s sort of to just get their appetite wet. Like they’re sort of put a little bit of money into it. They’re all of a sudden that much more interested in it,

[00:36:59] Trey Lockerbie: So I was kind of curious. 

[00:37:00] Andrew Wilkinson: It’s almost like a screener on the other Right. A screener with a little bit of money on the table. 

[00:37:04] Trey Lockerbie: Exactly. With that in mind and your relationship with Munger, he obviously is the right hand man of Warren Buffett, but he’s made his own choices along the way and his own investments.

[00:37:14] Trey Lockerbie: Have you picked up anything from being around him that has sort of informed you on where his mind takes him or why he’s opposed to certain deals or on certain deals? He loves Costco. He loves Alibaba. He loves certain companies that buffet for whatever reason, isn’t invested in curiosity if you’ve seen something that differentiates them that may or may not be obvious to the public.

[00:37:35] Andrew Wilkinson: The thing I love about Munger is just his level of patience is staggering. He’ll buy one. I think he had a great quote. He said, I read Baron’s magazine for 40 years and I bought one stock from it. And on that one stock I made a hundred x. He just sits on his hands year after year, and he does not do anything that he does not want to do.

[00:37:56] Andrew Wilkinson: So he does not interact with shareholders. He [00:38:00] runs Daily Journal exactly the way that he wants to run it. He’s just a, he’s a total character. He lives a life that is truly tailored for him, himself, and his own interests. 

[00:38:10] Trey Lockerbie: From what I understand, you were moved to Victoria. You’ve mentioned it a couple times and I know you had this really deep love, it seems for Victoria, from what I can tell.

[00:38:18] Trey Lockerbie: And but at first it seemed like you were kind of kicking and screaming being brought over there, but you’ve stayed there, which is just kind of something I find really interesting because you’ve also managed to stay in Victoria, but create your own luck. And I want to kind of explore this idea. You didn’t seem.

[00:38:35] Trey Lockerbie: Feel the need to go to some major metropolitan area and network and do things. You’ve been more on defense I would say, in a way. But you’ve managed to create your own luck and I’d like to see if you agree with the philosophy of creating your own luck. And one example I would bring up is actually bidding to have lunch with Bill Ackman, right?

[00:38:52] Trey Lockerbie: Knowing that you wanted to meet him and taking that opportunity to put yourself out there and do that. Are there other examples that [00:39:00] you found have helped you create your own luck and build relationships or especially being based somewhere not super remote. I mean, it’s crossed from Seattle now too, but you know what I’m saying, like it is, it’s almost that Omaha reference with Buffett we brought up earlier.

[00:39:14] Andrew Wilkinson: Yeah, so I moved here when I was 15. I grew up in Vancouver. Vancouver’s about two and a half million people. City Victoria’s about 300,000. So it was very small and I hated it. I was 16 years old, and did not want to move here. And over time I really wanted to move to a bigger city, but I always had a girlfriend.

[00:39:33] Andrew Wilkinson: My business was here and I ended up falling in love with the city. And I still would travel to Los Angeles and New York in San Francisco and I’d go to business conferences and stuff and meet all sorts of interesting people. But I found that I got a lot of independence by being in Victoria because there’s not a lot of business people that I would be interacting with.

[00:39:57] Andrew Wilkinson: And there’s not this kind of mimetic desire. [00:40:00] I was just in Los Angeles last week and I visited a house, this beautiful house that my friend had rented, and I asked him how much the house was worth and he said 70 million. , and I think that’s just the next level of competition. A world where the best house costs 200 million in Victoria, the best house costs 10 or 12 million, which is a lot of money, but that’s for the best house in town.

[00:40:23] Andrew Wilkinson: And so I think the level of competition is much lower. I feel that I’m quite an anxious person and I think that my anxiety is just lower, not having to be surrounded constantly by people talking about business and all competing. And so I really enjoy the quiet pace of life in terms of networking and stuff.

[00:40:41] Andrew Wilkinson: We’ve been fairly really lucky with some of the people that we’ve been able to connect with and it’s been a strategy of either really targeted reach out or it’s been getting into the right room. And so the way I would think about that would be a lot of people. Will kind of say, okay I’m not going to go to davo,  so I’m not going to go to Ted.

[00:41:01] Andrew Wilkinson: I’m not ready for those. I’m going to start at little small conferences, and I paid $15,000 to go to TED when I was a nobody. And I knew that if I put myself in a room with all those amazing people, Consistently year after year for 10 years. Eventually I would befriend people and connect with them and do business with them.

[00:41:21] Andrew Wilkinson: And so via conferences like Ted, I ended up meeting all these fascinating people, building my business, meeting amazing philanthropists and billionaire business people and all that kind of stuff. And then otherwise I would really study people from a distance. So Buffett and Munger I read everything I could for seven or eight years before I met them.

[00:41:38] Andrew Wilkinson: Ackman, I studied for years. Howard Marks, the all people that I’ve connected with since. But I would study them and when I really wanted to meet someone, I’d try and find a clever way to do so. So for example, with Bill Ackman I’d followed him for ages. And I just happened to see that he was doing a charity lunch.

[00:41:59] Andrew Wilkinson: And so I decided I was going to win that charity lunch, and I did $60,000 to go out for lunch with him. And I had no idea what to expect. I had actually invested in his publicly traded company. And so I looked at it as diligence. I had a very large position in it, and I said, okay, if Bill’s a jerk, I’m going to sell at the end of the lunch.

[00:42:18] Andrew Wilkinson: And if I like him, then I’m, maybe I’ll buy more and I’ll hold. And Bill was lovely. We spent three or four hours together. I ended up meeting his whole team at Pershing Square and we really connected. And at the end of the lunch he said, Hey, let’s find a way to work together. We should do business.

[00:42:36] Andrew Wilkinson: So I’ve done a lot of stuff like that and it’s worked out really well. But I didn’t go into that lunch with Bill expecting that something would happen. I mean he’s somebody that invests in railways and huge real estate multi-billion dollar public companies. I just wanted to learn from him, and that’s really been the approach that I’ve taken with all of the people I’ve met as just how do I get as much outta their brain as I possibly can 

[00:42:59] Trey Lockerbie: Talk  to us about.

[00:43:01] Trey Lockerbie: Bill Acme, because he’s not someone we’ve actually studied all that much on this show. He’s had, I wouldn’t say spotty track record, but he’s definitely been in the headlines and outta the headlines. He’s been very active, he’s been more quiet. He’s had losses and these massive wins actually fairly recently.

[00:43:16] Trey Lockerbie: What is it about him that sets him apart from maybe the other people you studied? 

[00:43:22] Andrew Wilkinson: So first of all, I’d say Bill, if you actually look at his track record, I think it’s mostly wins with a huge few huge losses. And the problem is that the big losses that he’s had have been very loud. And I think that Bill, because he formerly was an activist and was quite loud, I think the tallest blade of grass is the first to get cut.

[00:43:44] Andrew Wilkinson: So when things don’t go well, everyone loves to dunk on Bill, but he has an exceptional track record and I think he’s an amazing investor. I think what impresses me about him, what made him stand apart from a lot of the other value investors is. Most value investors, they effectively are buying a ticket on a cruise ship.

[00:44:03] Andrew Wilkinson: So what I mean by that is, let’s say you want to go to Hawaii there’s a lot of different ways to do it. So. You could go and build a boat, you know yourself by hand with some logs on the beach and try and sail to Hawaii, but you’ll probably die or drown or get sunburnt and maybe you make it one in a hundred times, but it’s probably not going to work.

[00:44:21] Andrew Wilkinson: That’s like starting a business. So that’s a venture. Then you could maybe go buy a speedboat or something like that. You’re going to arrive battered and bruised. That’s when you find a difficult business or a turnaround or something like that. The cruise ship would be you find a cruise ship that’s sailing to Hawaii.

[00:44:39] Andrew Wilkinson: The course is charted. It’s a reputable cruise line. It’s been operating for 20 years. You buy your ticket, a stock certificate, and you go and suntan on the deck for the entire time and you enjoy the ride. That’s what a lot of more passive investors like Buffet might do, or Guy Spear or Monish, pare.

[00:44:57] Andrew Wilkinson: They’re really buying the business. They’re trusting that the business is going to go where management says it’s going to go, and they kind of let the business do what it’s going to do. Bill, on the other hand, is much more entrepreneurial. So historically, when Pershing Square buys into a business, they actually have a thesis around change and in some instances it’s been mismanagement historically.

[00:45:19] Andrew Wilkinson: I think they’ve done a lot more of that kind of turnaround stuff like they did at CP Rail where they felt that the business was just not being operated well and had the wrong board, et cetera. I think they’ve since evolved to seeing opportunities in businesses that are already wonderful. Where they think that they can perhaps influence them in a positive direction from the board, but in a much friendlier way.

[00:45:43] Andrew Wilkinson: But what I like about Bill is that he’ll actually wrestle with the universe to try and see the outcome that he sees come to fruition. And I really like that. I think that he manifests things more than other investors. And so I find that very inspiring. As someone who’s an operator. [00:46:00] 

[00:46:00] Trey Lockerbie: I imagine having that much spotlight on you can be difficult.

[00:46:03] Trey Lockerbie: We’ve touched on this a little bit, but I happen to know that from some of your other interviews, that you’ve been into self-care in certain ways and you’ve gone as far as taking a month long sabbatical, a digital detox if you will, a couple years ago. I’m curious if you were able to do that again late last year, if you saw the same effect.

[00:46:19] Trey Lockerbie: Is it becoming something you’re really proving out to be helpful for you? And is there something that you maybe even picked up from these people that you’re around and learning from that’s helped you understand? because that’s one side of the equation that’s not often talked about. You see these people maybe get kicked around in the headlines or every move they make is scrutinized, but that’s so stressful.

[00:46:40] Trey Lockerbie: I’d have to say. Yeah. And no one talks about how they manage it. 

[00:46:43] Andrew Wilkinson: Well I think someone like Bill is incredibly tough. Right. Bill talks about falling down and. Brushing yourself off and getting back up. And Munger talks about that too. I think that the people who get back up are the people who continue to do well and they learn lessons and they become better investors or better business people as a result from my personal experience.

[00:47:04] Andrew Wilkinson: So one of the things I realized is that, At the end of the day, I’ve only got so much dopamine in my brain, right? So every email you read, every decision you make, you are depleting some chemical in your brain. And I think most people will observe that when they wake up, they’re the most full of ideas and excitement and forward momentum and quality decision making, and that kind of fatigues throughout the day.

[00:47:29] Andrew Wilkinson: And so what I’ve tried to do is make as few decisions as possible to abstract things away as much as possible, to remove time constraints and time pressures so that there’s nowhere I have to be. I can always cancel appointments, I can make a decision later. There’s no burning fires. But like I said earlier, I still struggle.

[00:47:49] Andrew Wilkinson: The feeling of overwhelm. Now they’re wonderful problems, right? I have all these fascinating businesses, each with their own unique opportunities to dig into.  But I feel a little bit like somebody with a Netflix queue that’s in the hundreds, right? There’s too many good movies to watch. There’s too many TV shows I want to watch.

[00:48:09] Andrew Wilkinson: There’s too many great books to read. So that’s what I struggle with which I think is a good problem to have, but it’s very difficult and I let anyone else swing into periods of excitement where I’m doing a lot, and then I get overwhelmed and I dial everything back, and then I start to get busy again.

[00:48:26] Andrew Wilkinson: And I just seem to repeat that pattern annually. 

[00:48:29] Trey Lockerbie: That last point resonates because when I was a musician, I was lucky enough to have this year I’d made enough money and I was like, okay, I have, I can not worry about money for a while. And every day was actually kind of torturous because I would wake up and not know what to do with my time.

[00:48:43] Trey Lockerbie: Do I practice scales? Do I read poetry? Do you name it. And I would end up just going to get a sandwich because I was like, I don’t know what else to do. Yeah. So do you find at the helm when you get to this level where you’ve delegated and if you’re not someone who just enjoys reading and maybe you are like a buffet for six, eight hours a day, how do you manage that?

[00:49:02] Trey Lockerbie: It’s actually something that’s probably harder than people even think about. They think it’s probably fairly easy to do, but I found it to be quite tortuous. 

[00:49:10] Andrew Wilkinson: Yeah, it’s surprisingly hard. So when Chris and I first started Tiny, at the time, we owned about five or six businesses that we had started.

[00:49:18] Andrew Wilkinson: We delegated the operations to CEOs and really we said to all the CEOs, look, don’t call us unless you need us. So the phone stopped ringing. We went from getting hundreds of emails a day, solving people problems, getting texted constantly to absolutely nothing. And at first it was bliss. We were thinking that we would become a young Buffett and Munger, we had this tiny little office and we would just sit there in our lazyboy chairs reading 10 Ks.

[00:49:45] Andrew Wilkinson: And I realized that I do not have that capacity. I think I can read for maybe one to two hours a day and maybe if I’m really obsessed with something a little bit more. But I am very social. I like to meet people. I like to be out and doing things and.  I do struggle with that. I find that there’s currently, at our scale, enough going on that every single day there’s still kind of two or three priorities or things that I’m pushing forward.

[00:50:13] Andrew Wilkinson: But a lot of what I’m doing is texting people and saying, Hey, remember that thing we talked about? How’s that going? Checking in. And then otherwise unless A CEO calls me with a critical problem, which doesn’t happen that often these days, I’m not getting into the actual underlying businesses.

[00:50:31] Trey Lockerbie: So when you talked to Buffett, you were talking about philanthropy, I think you mentioned as well and his initial game plan was to just compound until he died, basically. And I think luckily for everybody, Bill Gates at some point convinced him to start giving back with a warmer hand. And I’m curious what he impressed upon you with philanthropy, how you approach it, and maybe what causes, if any, motivate you the most?

[00:50:55] Andrew Wilkinson: Well, yeah, I was talking to him about the giving pledge and I really like the idea that any wealth that you build is just going back to society because it allows you to reframe from a kind of greedy mindset. I’m maximizing, I’m getting as much as I can to go buy a super yacht, to instead saying, you know what?

[00:51:13] Andrew Wilkinson: I’m the world’s best fundraiser for philanthropy, right? So saying that every dollar I make from this point on basically is going to go back to society at some point. I think there’s quite a nice way to reframe, because at a certain point I described earlier in the interview that my family didn’t have a lot of money, and so I just wanted to get rich.

[00:51:33] Andrew Wilkinson: I wanted to solve that problem. And I’d say probably almost 10 years ago, I had enough money where I could retire. . And then I had enough money that I could retire very comfortably, and then I had enough money that I could have my whole family retire. And at that point I was like, okay, well what’s the point?

[00:51:49] Andrew Wilkinson: And I ended up feeling a bit empty. So it wasn’t until I actually decided to give away most of my money that I was able to reframe and get excited again about working. 

[00:51:58] Trey Lockerbie: Is that around the time you? I’m trying to find the time when you spoke with Buffet and were seeking advice. Were you coming from that place of knowing or trying to figure out what to do next exactly? 

[00:52:09] Andrew Wilkinson: Yeah, totally. I think it was January, 2021, right after we took e-commerce public. And the interesting thing about that was that before that moment, I only owned private businesses. So while I had a lot of cash flow coming in I was almost constantly reinvesting the cash flow. I never had any real sense of what my businesses were worth or how they’d be valued in the market.

[00:52:32] Andrew Wilkinson: And when we took e-commerce public, that was actually only a very small percentage of my net worth. and those shares very quickly were worth tens and then even hundreds of millions of dollars depending on what the stock price was doing. And so it was kind of slapping me in the face. I was like, okay, I gotta figure this out.

[00:52:50] Andrew Wilkinson: And I had a bit of an existential crisis. I talked to Buffett, I interviewed a ton of other wealthy people to ask them what they were doing. And one of the frustrating parts of it is that everyone does something slightly different and all the advice seems to kind of counteract one another.

[00:53:04] Andrew Wilkinson: So, yeah, it was quite interesting to try and figure out. 

[00:53:08] Trey Lockerbie: What else keeps you grounded? I mean, we talked about living in Victoria. I imagine you might have friends, you’ve known your whole life to a degree just from growing up there. Have those relationships changed over time and is it hard to relate to people?

[00:53:21] Trey Lockerbie: Or is having that around you actually, what is grounding for you? 

[00:53:26] Andrew Wilkinson: Yeah, I mean, I still have a lot of great old friends who roast me and bring me back down the size, so that works out really well. It does change things and it’s such a blessing and a curse I think that being known as a successful investor and business person is wonderful as an extrovert, because I will be sitting in a cafe and I’ll have some random business person walk up to me and say, Hey, I heard you on a podcast last week.

[00:53:51] Andrew Wilkinson: Here’s my business. And wow, I just made a new friend. But I also find that it. Can sometimes convert you into a meal ticket for people. [00:54:00] People will email you constantly asking for things, people wanting loans. It just changes that stuff. Whereas before, before we went public the first business went public when we were kind of quiet and private.

[00:54:15] Andrew Wilkinson: No one really knew. I was just some guy in a hoodie working out of a cafe. And so it’s, yeah it’s a double-edged sword, no, don’t cry any tears for me. I’ve got a great life. But it does, it is an interesting dynamic to try and figure out 

[00:54:29] Trey Lockerbie: what would be some of your favorite books or resources that you recommend to people who are just getting started?

[00:54:35] Trey Lockerbie: I’m curious where you would push people to start learning, either about investing or starting a company, or simply just living a good life. 

[00:54:43] Andrew Wilkinson: Okay, so I’m a dropout. I went to journalism school for three months and then dropped out, and then I became a barista. And then there were two guys that kept coming into the cafe every day who were web designers, and I was looking at them and they would just sit in the cafe all day drinking espresso that I had made and going on their laptops.

[00:55:02] Andrew Wilkinson: And I was like, well, that seems better. So I became a web designer and just stumbled into it, and then my web design agency was doing well and was profitable, and so I kind of had to learn business. Then I started multiple businesses, and so it was very organic. One of the things that I noticed was that, Every job I ever had, I wanted to shove my boss outta the way and take over.

[00:55:24] Andrew Wilkinson: I just didn’t get why they were doing things the way they were. I thought I could do it better. I was kind of unemployable, which is the quality that so many entrepreneurs have. When I talk to kids who say, I want to be an entrepreneur, I’m going to go to school for entrepreneurship, it sounds a little bit like someone’s saying, I really want to be an Olympic athlete.

[00:55:43] Andrew Wilkinson: I’m going to go read a book about running. And it’s like, no, if you want to become a cross country runner, you should start running tomorrow. And that if it’s not completely slapping you in the face, that you don’t feel the urge that you have to do it. Then you probably shouldn’t because being an [00:56:00] entrepreneur is a very difficult life especially in the early days.

[00:56:03] Andrew Wilkinson: It’s really hard. It’s extremely exhilarating for the right type of personality, but it’s really hard and stressful, and the failure is brutal. So I would say, first of all, don’t start a business unless you feel compelled to. Don’t do it because it sounds good, or your parents want you to do it. Do it because you feel you have.

[00:56:20] Andrew Wilkinson: From there, the best resources for me were there’s a variety of business books that I love. The best one is a book called How to Get Rich by Felix Dennis. The title is not great. It’s really cheesy looking. It has a photo of him sitting on a golden throne on the front, but it’s really, he’s a publishing magnate from the UK who built a fortune.

[00:56:43] Andrew Wilkinson: And it’s a fascinating book because he kind of says, here’s everything you need to know in order to start a business and to get rich. And I’d say it’s quite accurate. I’d say followed many of the steps, but then the last quarter of the book is about why you don’t want to get rich and how miserable it made his life.

[00:56:59] Andrew Wilkinson: So it’s  a fascinating book. That was kind of my first book that really inspired me. In terms of learning, accounting and finance, like as someone progresses Khan Academy is amazing. You could probably spend two hours doing the finance and accounting course and learn everything you need to know. The E-Myth by Michael Gerber is amazing about delegation.

[00:57:18] Andrew Wilkinson: When I first started my business, I was imagine if I owned a bakery and I was trying to bake bake all the baked goods in the back at two in the morning and then work the till on the front and then run back and forth, covered in flour, trying to do a little bit of everything.

[00:57:35] Andrew Wilkinson: And the EMyth was the book that allowed me to kind of see that my business isn’t me. My business is a machine, and you have to build a machine built up of processes in people in order to scale. So that was a breakthrough for me. And then investing the Dondo Investor by Monish Bry, I think is the best kind of manual on value investing.

[00:57:55] Andrew Wilkinson: Just basic value investing. And then there’s the final book I’d recommend would be the Tau of Charlie Munger, which is much more qualitative. I always think of Munger as a wonderful qualitative investor. So Danto investor is here’s how to buy a dollar for 50 cents.

[00:58:10] Andrew Wilkinson: Munger is much more about how to examine business quality psychology and incentives, which you come to realize is far more important than any of the numbers stuff. 

[00:58:20] Trey Lockerbie: On that last point, I’m just curious if Munger Buffett, Bill, anyone has put a book in front of you that was maybe interesting. I had dinner with Buffett once and he gave me a couple Adam Smith books to read.

[00:58:32] Trey Lockerbie: And for me that was eye-opening to this idea of owning a business vehicle in the book that they describe as peeling off equity to create liquidity and things like that just stuck with me, the visual. But it was this idea of how people grow and make a living off of a business. And I’m curious if there’s been references from anyone like that, that maybe have stuck with you as well.

[00:58:53] Andrew Wilkinson: The most important book that I’ve probably ever read is influenced by Robert Salini, which Munger is a huge fan of. He’s the reason why I discovered that book, and effectively it’s like an encyclopedia of every kind of cause of psychological misjudgment. Charlie Munger also has a really great speech that he did at Harvard called The Psychology of Human Misjudgment.

[00:59:15] Andrew Wilkinson: He made it in the nineties. It’s kind of this old crackly recording, but it summarizes all the kind of key ways that people don’t think through stuff properly. That book is incredible. I still use all the skills I learned in that book every day. 

[00:59:27] Trey Lockerbie: Fantastic. Well, Andrew, I’ve learned so much from you today and I have a whole laundry list now that I’m so excited to go dig into because a lot of these I’d never even heard of before.

[00:59:36] Trey Lockerbie: So really exciting and I, we will list all of these resources in the show notes. Thank you so much for taking the time to speak with us. And before I let you go, I would love it if you could share a little bit more with the audience about how they can learn more about Tiny, because it’s a really fascinating thing you’re building.

[00:59:51] Trey Lockerbie: And just if you want to direct them anywhere to learn more about it, please do. 

[00:59:55] Andrew Wilkinson: Yeah, so the best place to learn more is to [01:00:00] go to tiny.com, our website. You can see a high-level overview of all the businesses we own and how we buy businesses. I’ve done a lot of podcast interviews and I often go on My First Million.

[01:00:14] Andrew Wilkinson: That’s more off the cuff brainstorming, more entrepreneurial. I’ve also done a couple of interviews on the philosophical side with Shane Parrish on the Knowledge Project. Then, I did one on 20 Minute VC, which is like a really good summary in 20 minutes of exactly how we invest and how we constructed our business.

[01:00:36] Andrew Wilkinson: But yeah, Trey, thank you so much. It’s great to finally come on, and as a long-time listener, it’s very cool.

[01:00:45] Trey Lockerbie: Thank you so much again.

[01:00:46] Andrew Wilkinson: Of course. 

[01:00:47] Trey Lockerbie: All right, everybody, that’s all we had for you this week. If you’re loving the show, don’t forget to follow us on your favorite podcast app. And if you’d be so kind, please leave us a review. It really helps the show. If you want to reach out directly, you can find me on Twitter @TreyLockerbie. And don’t forget to check out all of the amazing resources we’ve built for you at theinvestorspodcast.com. You can also simply Google TIP Finance, and it should pop right up. And with that, we’ll see you again next time. 

[01:01:25] Outro: Thank you for listening to TIP. Make sure to subscribe to Millennial Investing by The Investor’s Podcast Network and learn how to achieve financial independence. To access our show notes, transcripts, or courses, go to theinvestorspodcast.com. This show is for entertainment purposes only. Before making any decision, consult a professional. This show is copyrighted by The Investor’s Podcast Network. Written permission must be granted before syndication or rebroadcasting.


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