Andrew Wilkinson: Tiny Holdings

Summary

Podcast Summary: The Knowledge Project – Andrew Wilkinson: Building an Empire

Host: Shane Parrish
Guest: Andrew Wilkinson, Co-Founder of Tiny
Date: July 26, 2022

---

Episode Overview

In this episode, Shane Parrish sits down with Andrew Wilkinson, co-founder of Tiny, a holding company owning over 40 businesses including Aeropress. The conversation dives beyond business tactics into the psychology and philosophy behind Wilkinson’s journey—covering topics such as mimetic desire, dopamine addiction, leadership, wealth, raising children, living outside major tech hubs, and the importance of structure, discipline, and community. Wilkinson openly discusses his mental health struggles, learning from failure, addiction to achievement, and building a meaningful life not just in business, but in family and community.

---

Key Discussion Points & Insights

1. Dopamine Addiction & Technology Detox

• Wilkinson’s Burnout and Digital Detox:
  Wilkinson describes a period during the pandemic when he became addicted to social media validation and business stimulation, leading to profound anhedonia (inability to feel pleasure).

  • “I just kind of hit a wall. I woke up one day...and I just didn’t want to get out of bed...All my usual tricks didn’t work.” (02:18, Andrew)
  • He rebooted by putting away all devices and spending a month at his lake house, experiencing withdrawal-like symptoms and later a reset in his baseline for pleasure (03:40–05:14).

• On Dopamine Addiction:

  • “If you eat chocolate cake once a month, it’s really pleasurable. If you eat it daily, your brain starts demanding it hourly. And if you do that, it’s just miserable. And I think we all do that with phones, devices, food, drugs.” (05:17, Andrew)

2. Mimetic Desire and Comparing Yourself to Others

• Unpacking Mimetic Desire:
  Inspired by reading Luke Burgis’s "Wanting", Wilkinson explains mimetic desire—the tendency to want things simply because others do.

  • “Whatever the people you surround yourself want, you end up wanting as well. But what’s fascinating...most people don’t intrinsically want those things.” (06:34, Andrew)
  • Shares an anecdote about billionaires still experiencing envy: “This is insane, right? Like, where does this end?” (07:53)

• Intrinsic Motivation vs. External Validation:
  Wilkinson details how chasing externally modeled desires leads to dissatisfaction and a lack of appreciation for one's own achievements (08:32–10:34).

3. The Need to be Needed & Perpetual Dissatisfaction

• Entrepreneurial Drive and Discontent:
  Wilkinson identifies the double-edged sword of always needing to improve things:

  • “James Dyson...says, ‘I’m perpetually 20% dissatisfied with everything’...I think I always feel that way.” (11:26)
  • “Most successful people are just an anxiety disorder harnessed for productivity. And I’m certainly that case.” (12:36)

• Delegating & Stepping Away:
  Despite building strong management teams, Wilkinson struggles to fully detach:

  • “I’m addicted to feeling important, to problem-solving, to brainstorming, to talking to young entrepreneurs, to being necessary.” (15:44)

4. Advantages & Challenges of Building a Business in Victoria, Canada

• Operating Outside Silicon Valley:

  • Lack of easy access to capital led to discipline and a focus on profitability: “It forced me to actually run a profitable business.” (16:13)
  • Insulates from the pressure of mimetic desire (“I don’t need to go and buy a $100 million house and a super yacht because I don’t compete with those people.”) (17:44)

• Competing Against Venture-Funded Companies:

  • Learned hard lessons about trying to compete in markets where capital is king (e.g., losing $10M building project management software against Asana): “He was the American military and I was like the Fijian military.” (18:29–21:09)

5. Hiring CEOs & Building Effective Teams

• Recognizing Different CEO Profiles:
  Outlines how different stages of a company require different types of leaders (scaler vs. maintainer) and the priority for ethics and cultural fit.
  • “Would I let this person babysit my kids?... Am I nodding along with what they’re saying?” (24:24)
  • On relinquishing control: “You can’t dictate to a CEO what the strategy needs to be.” (25:42)

6. Wealth, Meaning, and Happiness

• Spending Wealth for Meaningful Life:

  • Wilkinson prefers spending on experiences and learning from interesting people, rather than material luxury:
    • “The typical path for wealthy people...buy a plane, buy a yacht...What I have realized that drives me is all I want...is that I can just meet interesting people.” (27:31)

• Community Engagement:

  • Uses wealth to build community in Victoria (local news, restaurants, hotel), believing it’s easier to have a lasting impact as a “big fish in a small pond.” (29:40)

7. Learning from Failure in Tangible Businesses

• Restaurants and Tangible Projects:
  • Openly discusses early failures, like losing ~$1M on a restaurant, and how sticking "forks in electrical sockets" leads to learning. (“We made every conceivable mistake.”) (30:41–32:39)
  • Finds satisfaction in bringing ‘boring’ but community-rooted institutions to life.

8. Structured Conversations and Entrepreneur Forums

• Value of Entrepreneur Forums:
  Wilkinson relies on several confidential entrepreneurial peer groups for support and structured self-examination:
  • “What you end up with is this kind of impartial board of directors and great friends that you end up bonding with.” (34:06)
  • Advocates for “structured conversations” using prompts or cards to induce deeper connection (36:24).

9. Health, Self-Experimentation, and Behavioral Change

• Health Obsession:

  • Tracks biometrics compulsively, funds health research, and recognizes the irony in becoming anxious about health optimization:
    • “It’s kind of like porn for anxious people, right?...I wear a glucose monitor. I wear my Apple Watch, I wear Oura ring, all that stuff.” (37:40)
  • Funds scientific studies, such as depression treatment with saunas, to bridge lab findings and real-world impact. (37:40–39:59)

• Self-Binding and Environmental Rules:

  • Avoids temptation not by willpower, but by designing his environment (“self-binding”), e.g., not keeping ice cream in the house. (65:52–67:05)

10. Raising Children and Generational Wealth

• Challenges of Raising Privileged Kids:

  • “My kids will be those rich kids and I don't know how to create in them that same kind of drive or hustle yet.” (43:10)
  • Struggles to balance providing opportunity with instilling appreciation and grit; concludes, “Your kids need to know that you’re there and you love them. And I hope that’s enough.” (45:32)

• The Value of Learning:

  • Hopes to instill a love for learning and curiosity over a relentless need to hustle for money (45:51–47:14).

11. Approach to Fund Management and Public Investing

• Stress of Managing Others’ Capital:

  • Raised a $200M fund during COVID but realized he doesn’t enjoy “owing people things or letting anyone down.” Prefers losing his own money to losing someone else’s (47:55–50:12).

• Investment Philosophy:

  • Admires Warren Buffett and Bill Ackman’s business-holder approach. Pershing Square Holdings is his sole public investment, reflecting trust in philosophy and people, not just numbers (50:35–55:58).

12. Taking Companies Public & The Impact of Tickers

• Experience with Public Markets:
  • Wilkinson talks about taking WeCommerce public and learning on the job, crediting mentorship from Bill Ackman and Charlie Munger.
    • “My net worth would increase or decrease by $20 million on any given day. And that scared the hell out of me. But...unless you’re selling, it just doesn’t matter.” (59:48–60:07)

13. “Forcing Functions”: Habits for Entrepreneurial Success

• Making Things Real:

  • Advocates talking about ideas early and often to give them momentum and create social accountability (61:31–62:46).
  • Encourages hiring quickly and learning hands-on (even from the wrong people) to avoid paralysis by analysis.

• Habits and Rituals:

  • Prioritizes sleep and routine, acknowledging that physiology—especially fatigue—fundamentally shapes one’s ability to deal with stress (63:59–65:32).

14. Boundaries, Environment, and Avoiding Bad Deals

• Self-Binding Examples:

  • Uses technology restrictions, public commitments, and even silly incentives (like an embarrassing hat) to change behavior (67:30).

• Negotiation Lessons:

  • Emphasizes ethics and avoiding deals with bad people, quoting Munger: “When you find yourself over a stinky sewer, just plug your nose and keep walking. You don’t need to climb down.” (68:52–70:17)

15. Defining Success and Legacy

• On How He Wants to Be Remembered:
  • “I just want my kids to love me at the end of the day. I know that’s kind of cheesy, but...I don’t care what people say about me after I’m dead, because I’ll be dead. But my kids are part of me. Right. And I want them to know that they were loved and taken care of.” (70:34)

---

Notable Quotes & Memorable Moments

• On the curse of achievement:
  “Most successful people are just an anxiety disorder harnessed for productivity.” (12:36, Andrew)
• On mimetic desire:
  “These are the people that have reached the very top. And they’re all still striving, they’re all still looking up, they’re all still comparing.” (07:53, Andrew)
• On community:
  “When you’re a big fish in a small pond, you can actually [make an impact]. So I’m having a lot of fun with that.” (29:40, Andrew)
• On learning from mistakes:
  “Chris and I like to joke that we take forks and we stick them in electrical sockets, and then we learn and we start calibrating.” (30:41, Andrew)
• On success and legacy:
  “I just want my kids to love me at the end of the day.” (70:34, Andrew)
• On negotiation:
  “You can’t make a good deal with bad people.” (70:17, Shane)

---

Timestamps for Important Segments

• Dopamine addiction and detox: 02:13–05:14
• Mimetic desire and billionaire envy: 06:22–08:32
• Entrepreneurial dissatisfaction: 11:17–13:56
• Advantages of building beyond Silicon Valley: 16:13–17:44
• Lessons from competing with venture startups: 18:17–21:09
• Hiring, trusting, and empowering CEOs: 21:11–26:49
• Wealth, meaning, and community: 27:22–32:39
• Restaurant failures and tangible projects: 32:39–34:06
• Value of entrepreneurial forums: 34:06–36:24
• Health, wellness, and behavioral science: 37:30–41:15
• Raising kids with wealth: 43:02–47:14
• Raising and running a fund: 47:39–50:12
• Public company lessons: 56:01–61:18
• Habits, sleep, and forcing functions: 61:18–67:05
• Negotiation and bad actors: 68:47–70:20
• Defining success and being remembered: 70:26–72:31

---

Conclusion

This episode is a candid exploration of the often unseen personal, emotional, and community dimensions behind building, leading, and sustaining a business empire. Wilkinson’s openness about his struggles, his disciplined approach to business, and reflections on meaning, family, and impact provide timeless lessons for both entrepreneurs and anyone interested in living a reflective, intentional life.

Transcript

[A]

James Dyson. I read. So James Dyson is the guy who started the Dyson Company. They make fans and hair dryers and vacuums and all sorts of stuff. He has this great quote. He says, I'm perpetually 20% dissatisfied with everything. Right. He's 75 or something and he still feels that way. And I think I always feel that way.

[B]

Welcome to the Knowledge Project. I'm your host, Shane Parrish. The goal of this show is to master the best what other people have already figured out. To that end, I sit down with people at the top of their game to uncover what they've learned along the way. Every episode is packed with timeless ideas and insights that that you can use in life and business. Today I'm speaking with Andrew Wilkinson, co founder of Tiny, a holding company that owns over 40 individual businesses, including brands you might be familiar with like aeropress. Andrew is a longtime friend and business partner. We have multiple investments together. I'm an investor in his fund and one of his companies, Metalab, has sponsored the Knowledge Project for years and will continue to do so in the future. We talk about mimetic desire, exploring why at one point Andrew found himself in the midst of wondering what he wanted and why and feeling unhappy and lost. We also talk about his need to be needed. Building a business out of a sleepy Canadian city, competing with venture backed companies who are not focused on profit, hiring CEOs, why he wants to build something tangible and not just software based, and the mistakes, losing millions of dollars, hiring the wrong people and so much more. We also explore why it's important to just get started and not get caught in the endless loop of research and never doing. It's time to listen and learn. Last summer you woke up feeling hollow.

[A]

Yes.

[B]

And life sort of lost its meaning. Can you talk to me about that and what was happening?

[A]

Yeah. So I'd had this very strange last couple years where, you know, it was Covid. I hadn't really talked about what I did. So we had kind of quietly been building a company up here in Victoria, Canada for 15 plus years and been very quiet. You know, we had a few people who knew what we did, but I never talked about it publicly. And I started going on podcasts and tweeting because I was bored and. And I ended up going down a total rabbit hole where I was becoming like an influencer. Like suddenly I was posting every single day. I was comparing myself to other people with more followers on Twitter. I was beating myself up for not writing a tweet a certain way. I was Getting misinterpreted on Twitter, like, just everything was. Was about that. And I also took a company public, raised a fund, had to make a bunch of really difficult decisions around personnel, hiring and firing people. And I just kind of hit a wall. I woke up one day, like, August 1, 2021, and I just didn't want to get out of bed. And it wasn't that I was depressed. It was like an ahadonia. Like, I just. All my usual tricks didn't work. Drinking a cup of coffee wasn't pleasurable. Going for a walk wasn't fun. Fun. You know, playing video games wasn't fun. I couldn't find anything I liked on Netflix. My phone gave me no pleasure. And I was like, I have no idea what's going on, but all I know is I've just got to stop this and reboot. And so I put my phone in a drawer. I went up to. We have a lake house up at Shonagan Lake, about 30 minutes away. And I didn't touch my phone, email, music, podcasts, anything for about a month. And for the first couple days, I was, like, drug addict, in withdrawal. I was incredibly miserable, angry at my wife, a huge jerk. And then after that, I started being able to actually have the ability to sit and look at a view without having to take a photo and share it. I started being able to engage with my kids for an hour and just play with them. And I kind of realized that I was kind of like a drug addict, but with phone and stimulation and business. And so I did that for about a month. And I remember after a month, I walked into a cafe, and there was some very tame kind of crappy music playing, and it was like an orgasm. It was, like, amazing. And I realized I just kind of reset my benchmark, but I didn't really know what happened. And around that time, I randomly listened to a podcast about opioid addiction, and they talked about people who are. You know, opioids stimulate dopamine, and dopamine can be triggered by anything. It could be your phone. It could be chocolate cake. It could be heroin. And I realized I'd basically done a heroin detox just for business and dopamine addiction. And so it was incredible. I just totally rebooted my brain.

[B]

How did you come out of that and not go back? Like, fall right back into it?

[A]

Oh, I did. I mean, like, anyone. I mean, I. It's like anyone who's ever quit sugar, right? You go through three, four days of difficulty, and then it's totally fine. For six months. And then you have one bite of ice cream, and your brain just starts firing off. And every single time you're in a restaurant, you say you'll look at the dessert menu and you start ordering chocolate cake all the time. And what ends up happening is that if you eat chocolate cake once a month, it's really pleasurable. If you eat chocolate cake once a week, it's pretty good. If you eat it daily, it's okay. But then your brain starts demanding it hourly. And if you do that, it's just miserable. And I think we all do that with phones, devices, food, drugs. For some people, anything. And too much of a good thing is always a bad thing.

[B]

And the feedback's immediate and visible. Right? Like it's people liking you and retweeting you and validating your thinking.

[A]

Totally. Totally. So it's all extrinsic. None of it was actually internal. And, yeah, I just. I've. I've really. I mean, frankly, I haven't really done any podcast interviews until this one. Right. For the last six, seven months for that exact reason.

[B]

Talk to me about that. External versus internal. Because this is something we've talked about before through phone calls and dinners, where you find yourself wanting things that you don't actually want. You want them because other people want them.

[A]

Well, there's this. I think you did an interview with Luke Burgess, who's the guy who wrote this book called Wanting. And I read that book this summer, actually, and it kind of blew my mind. It's about the idea of mimetic desire and. And mimetic desire. It's very simple. Imagine we're in a bar and you're thinking, you might want a beer. And then I order a gin and tonic. I've modeled that. A gin and tonic is a great drink. Maybe you change your mind. That's the simplest form of it. The more complex form would be you're in a social group where those who are in that group are all into wine, or they're all comedians and they all want a Netflix special, or. Or they're all musicians and they want to play live in some big arena. Whatever the people you surround yourself want, you end up wanting as well. But what's fascinating about it is most people don't intrinsically actually want those things. When you actually talk to them about why they want them, they actually just want it because other people have modeled it as a desirable thing. And so what happened for me was that I. Before I got home, and I did that reboot, I had spent a year going through the world of high finance, meeting all these billionaires, super successful people, meeting people on Wall street, all sorts of successful entrepreneurs, and realizing what made me sad was that these are the people that have reached the very top. And they're all still striving, they're all still looking up, they're all still comparing. I remember I once spoke to a person that's worth $2 billion and he made an offhand comment. He goes talking about some other billionaire who's worth 20 billion. He goes, oh my God, he's so rich. And I said, hold on a second, you're worth $2 billion. What can he do that you can't do? And the guy just kind of goes a bit glassy eyed and quiet, and he goes, he can buy a super yacht. And I was just like, this is insane, right? Like, where does this end? Right? And I think that's mimetic desire at its worst. It's envy and it's driving people to not appreciate what they have, no matter how much they have.

[B]

How did you decouple sort of like your external desires? And what was pushing you from like, what you really want? What is it you really want?

[A]

Well, that's an interesting question. I think at the end of the day, what I want is a sense of safety and security. I think that's what has always drove me. In my family, we never had enough money. And it wasn't that we were hard done by, we weren't on food stamps or anything, but money was just always a sense of. It was something that created a lot of tension in our house. And I just didn't want people to be tense. I didn't want people to be anxious. So that always drove me to want to make money and kind of take care of everyone around me. And that still drives me. I still have that fear. I have almost 1,000 employees now and I'm constantly going like, yes, the numbers are bigger, but now I have more people to take care of. Now I have kids. The equation's always changing. And I think the fascinating question is, at what point do you switch from waking up every day and making something of the day versus waking up and enjoying it? There's that great E.B. white quote. And I think I really struggle with that because I wake up every day and I feel like the way I would put it is the way I started my business was that I found it very relaxing to go and chop wood in my backyard. So one day I start chopping wood in my backyard and my neighbor pokes his Head over the fence. And he says, andrew, I have a wood burning fireplace. Can you chop some wood for me? And I say, absolutely. And he goes, I'll pay you 20 bucks. And suddenly a hobby became a business. And before I knew it, I'd hired three of my buddies and we're a merry band of wood choppers in my backyard. And we're suddenly selling door to door all through the neighborhood. And then one day, 15 years later, I wake up and I own 10 sawmills. And I just sit in a little box at the top with glass. And I look out at the sawmill and all the machines and all the workers do their work and. But I still feel the need every day to wake up and chop wood.

[C]

Shopping is hard, right? But I found a better way. Stitch Fix online personal styling makes it easy. I just give my stylist my size, style and budget preferences. I order boxes when I want and how I want, no subscription required. And he sends just for me pieces, plus outfit recommendations and styling tips. I keep what works and send back the rest. It's so easy. Make style easy.

[A]

Get.

[C]

Get started [e-mail] Spotify. That's stitchfix.com Spotify.

[A]

Why do I need to do that? Right. Like people, I find every entrepreneur has that inherent drive where they have to achieve and even when it's not really necessary to achieve. So I think I'm kind of struggling with that right now.

[B]

We were talking last night at dinner, and one of the things that you said was the things that make you successful also prohibit you from enjoying that success. Do you want to elaborate on that?

[A]

Well, I think it's exactly that thing, right? It's that need to. James Dyson. I read. So James Dyson is the guy who started the Dyson Company. They make fans and hair dryers and vacuums and all sorts of stuff. He has this great quote. He says, I'm perpetually 20% dissatisfied with everything. Right? He's 75 or something, and. And he still feels that way. And I think I always feel that way. I always want everything to just work better, whether it's my house, you know, does. How does the dog get fed in the morning? Can I make a system to make sure that happens without me having to remember it to a massive business, you know, in Aeropress going, Can we make the box 30% smaller so that we can ship it more cheaply? I just like systems. I like making things work better. And. And so if you have that desire, then it's hard to just be satisfied.

[B]

With your Day to day life and you're never done. Right. This is the curse and the blessing of the entrepreneur. Right. Like there's always room for improvement. There's always something you can be doing when you're not at work. You're always thinking about, oh, I could be working, I could be doing something, I could be getting better.

[A]

Well, and it's, it's what's fascinating. Like I, I like to say, like most successful people are just an anxiety disorder harnessed for productivity. And I'm certainly that case. Right. I wouldn't say I'm a dysfunctional, anxious person. I'm somebody who has a lot of anxiety and then I harness it by ticking off to do's. And about a month ago I was sitting with my wife watching a movie and you know, it was a Sunday night watching one of the Oscar movies or something and I'm sitting there with my fists bald going, oh, I didn't send that email and I need to do this. And you know, what about that project? And, and then I'm going, oh, my wife's going to be mad at me. Like, you know, there's a lot of anxiety. And so recently I've been going, you know, how do you turn that voice off? Can you ever turn that voice off? Right. Can you do it chemically? Can you do it via exercise? Can you do it by changing your goals? I don't know.

[B]

Do you remember David Sokol who used to work at Berkshire Hathaway with Warren Buffett? He wrote a book that a lot of people have never heard of, but the title of that book sort of like sums up this, which is plenty of Pleased but not satisfied.

[A]

Huh. Crazy. Did he, Was that before the conflict and everything that happened? Oh yeah, I should read that.

[B]

So I always like the title of that book because I think it speaks to the mindset that we're talking of where you're pleased but you're never satisfied. So you're always driven.

[A]

But there's a fetishization of that. Right. You know, I think in a capitalist system, people like me or you or that are just that have that dissatisfaction, they, they can drive it. And that might work well for the economy or for your employees or whatever, but at the end of the day, does it actually make you happy? Right. And I don't know. I'm not unhappy. I'm pleased but not satisfied. Right. It's fascinating.

[B]

Well, it's definitely different than sort of like going home and checking out. Right. Or not being able to think about these things and like parking Work at work. Because like you have how many companies now?

[A]

40 that I wholly own.

[B]

You always have a problem, right? There's always a problem. There's always like an employee doing something or CEO that might be quitting or somebody's upset, not happy and so you can't actually get that space. It's interesting that you went to the lake house and just like turned it.

[A]

All off one month. You know what's fascinating is I went away for a month and I, I put up an autoresponder on my email.

[B]

Which is still there to this day.

[A]

It's still there actually to keep my email down. But I told my assistant, you know, look, just respond to anything you need to respond to, reroute anything. And I got back after a month and actually nothing bad had happened and a lot of really excellent work had happened. And so it made me realize I have a great team. I'm like the wood chopping guy who owns all the factories and it has, every single factory has incredible management. And if I leave for a while, things continue to go. And at the end of the day, the way that I've structured my business is that I am ultimately just making decisions around capital allocation and there's not that many to make a year. And so I should be able, technically I should be able to remove myself from a lot of that stuff. But I think I'm still addicted. I'm addicted to feeling important, to problem solving, to brainstorming, to talking to young.

[B]

Entrepreneurs, to being necessary.

[A]

To being necessary. So it's a double edged sword.

[B]

Talk to me about some of the advantages to being in Victoria, Canada. When people think of building a company or thousand employees or holding company or something like that, this is not the first place they think of. And yet here you are in Victoria and similar to Toby who's in Ottawa, people don't think of building, you know, Shopify, coming from Ottawa. And so what are the advantages to being here?

[A]

Well, the two main advantages. One is I was, I had no access to capital, which, which sounds like a very negative thing, but it forced me to operate with a lot of discipline. So when I ran my first business, I didn't have venture capitalists pursuing me. I didn't have access to venture debt or bank debt or anything. I couldn't even get a credit card. And so it forced me to actually run a profitable business. And it's amazing how most Fortune 500 businesses, traditional business, everyone understands having a profit. But for some reason in technology, it's this very foreign concept where you raise massive Amounts of venture, you take all this risk, 5% of them work, and then maybe 15, 20 years down the line, you have a profit. And we just started entering areas of technology where we could run profitable businesses where nobody thought you could. And so, and I didn't know that was unique. I didn't know what I was doing. I didn't start my business with an MBA however, no idea that I was even starting a business like the wood chopping example. It was a thing I did and that gave us a lot of discipline. So even today we only focus on profitable technology and now some brick and mortar businesses. The other thing that's been great about it, going back to the idea of mimetic desire, the people that I'm surrounded with are mostly people who have chosen to live in Victoria because of the lifestyle of or completely disconnected from business. And so while I've got a wonderful network of amazing people like you and people in New York and L. A and all over the place who I can talk to when I want to talk business or finance or something, I don't live amongst those people. So I don't compete with them. So I'm not. I don't need to go and buy a $100 million house and a super yacht because I don't compete with those people. I'm just out of the pond. And I think that's been a huge blessing and it's enabled me to be quite content despite whipping myself for the last 10, you know, 10 or 15 years.

[B]

Talk to me about that forcing function that you mentioned earlier about running profitable. But you're competing sometimes against venture where profits aren't the motive and growth is. How do you operate in that world?

[A]

Well, that's a lesson I learned the hard way. So my first business was a company called Metalab, which I still own. It's a product, product design agency now works with Fortune 500 companies and startups and stuff. And that was an agency and that was a business that I could run profitably from day one, right. I was doing the work myself. If I knew that it was going to cost me, you know, $40,000 to do a project, I could bill $80,000 and make a $40,000 profit. Very straightforward, simple business. Around that time I was profitable and I was stacking up cash and I was trying to figure out what to do with it. And I started reading about these guys, Jason Fried and David Heinemeier Hanson at 37 Signals and Basecamp. And they had this thing where they had built this software to help them run their agency and they charged monthly for it. It was an early SaaS business and I got hooked on this idea of going to sleep at night and waking up in the morning and having made money from versus having to go fight for every dollar like you do in an agency. And so I decided that I was going to build project management software to help me run my agency. And I built a product called Flow. And what I didn't realize was that I was going into a hyper competitive market where capital mattered. So at the same time that I started my project management software business, the co founder of Facebook, Dustin Moskovitz, started Asana. He went off and he raised venture capital and it was a little bit like he was the American military and I was like the Fijian military. Right. I just had this tiny little force and very few resources and I just couldn't go up against Goliath. And so because I didn't understand those market dynamics and the fact that, you know, even if you have an inferior product, not that I think their product is inferior, but if you can outspend and outmarket, you can win the battle in the venture world. And so frankly they just outspent us and eventually they had a much better product than we did. And I ended up losing $10 million doing that. So I've done that scar tissue. And now I really focus on businesses where I think that I can predict the outcome where with reasonable certainty and I'm not having to compete with the venture folks. So I don't want to get into AI and drones and vaccines. I don't want to get into areas where you need massive amounts of risk and capital. I want to jump over the one foot hurdles. I want to fish where the fish are. So most of our businesses are kind of off the beaten path and many would consider them kind of boring. But I think boring is beautiful.

[B]

There's riches and niches.

[A]

Exactly.

[B]

One of the things I want to explore with you is sort of the difference between hiring a CEO at an established company like Aeropress or a startup like Supercast. How do you think about the skills necessary and what lessons have you learned from hiring hundreds of CEOs?

[A]

Yeah, I think think about a business like Chipotle. So there was the person that created the original burrito, right. That was the innovator. And then there was the person who said, oh, we should take the burrito and we should do that in a fast casual style. That's the founder of Chipotle. Then there's the person who says, hey, we should take this to instead of five locations to 100 locations, that's a profile of someone who's aggressively going to take a concept, take an ember, pour gasoline on it and scale it. And then there's finally the kind of steady state CEO who takes over and they kind of slowly grow it from there. And so those are the different profiles. I think that a later stage company, you really just need to implement best practices. So what I look for in a later stage company profile is I say I want to hire someone who's really kind of done this before in a similar or adjacent industry and they've run a business that's at least double the size. And so for example, when we bought Aeropress about six months ago, we hired the CEO, former president of SodaStream and he had scaled that business to over 200 million. And it's a very similar, it's different in some ways, but very similar consumer packaged goods business. And so as I talked to him I just found myself nodding along with all of his assumptions. And he wasn't saying we need to be radically innovative, we need to introduce new material science, we need to spend a bunch of money on R and D. It was really hey, this business, you know, we need better logistics, we need more warehouses, we need better relationships, we need better E commerce. Those are kind of base hits and that's the kind of stuff I generally like to do. Not that we won't do innovative things as well, but I like to focus on those base hits first. With the early stage company that's much more complex, especially in this market because you have so many people who go off and found their own companies. What I look for typically is somebody who's not founder risk averse. Like a founder will just run into battle, they just want to go raise their own money and do everything themselves. I look for someone a little more risk averse who is maybe a number two or a number three at another at scale company. And, and I go to them and I say look, I've already created this startup, I've got the concept, I've got the money, I can raise the money for you if you need it, I can provide all the resources you need, but you need to take this ember and scale it. And so they're like the person who takes it from Chipotle from one location to 20.

[B]

Let's dive into the AeroPress one a little bit more. I want to know like take me behind the scenes. Like I remember at the final stage you had two very different candidates in mind for the business You. You ended up selecting the. The person that you have now. But, like, what questions did you ask? How did you determine which CEO you were going to go with? Because that was a fork in the road. Right? You had two very different final candidates.

[A]

So I had a really. I've gotten really fortunate to get to know Charlie Munger over the last couple years. And I was on the phone with him about a year ago, and I kind of told him a few stories about different experiences we'd had with CEOs. So in one example, a CEO came to me and he said, hey, I want to spend a million dollars, and I want to try building this new revenue line. And I said, I think that's a bad idea for all the following reasons. And I'd had that experience. I'd actually tried to build a similar business. And he said, no, I really think this is important. I really want to try it. And in that moment, I had a choice. I can either be the dictator and say, no, I have majority control of the business. Sorry, you're not doing that. He. He resents me. Maybe he builds a narrative that he didn't hit his growth target because I disallowed him from doing it. And so I actually had to let him go and light a million dollars on fire to go do that experiment. Now, fortunately, it was a large business, and that didn't really matter in the grand scheme. And he built scar tissue. That was awesome. But I've learned. And so I relayed that story to Munger, and he said, I've never, ever had any luck changing anyone's mind in my whole life. People come to their own conclusions, and they have to go and have those experiences. And I've found that to be true. And so when I'm talking to a CEO candidate, the number one thing I'm looking for is, are they ethical? Right. I've also learned that lesson before. I really want somebody that I completely trust. The heuristic that my business partner, Chris, and I use is, would I let this person babysit my kids? Right. Or would I be okay if I got stuck on a cruise ship talking to this person for, like, three days? Right, Right. And if those things are true, that's great. From there, it's really. Am I nodding along with what they're saying? Because at the end of the day, what I've found is, to a man with a hammer, everything looks like a nail. And if they have a certain thing that they want to do, you kind of have to just let them go and execute on that strategy. You can't dictate to a CEO what the strategy needs to be. And so in the case of the CEO candidate we chose, I just found myself constantly nodding along. And every email he sent me, I went, yes, that is so logical. And I wouldn't even have thought of that, but that makes perfect sense. And to me, you know, he's ethical. I like talking to him. He's a good communicator, and I agreed with his vision. So that was how we made the decision.

[B]

So are you asking sort of like, okay, well, here's the situation. What's your plan for the company? How would you run it? What does that look like? What are those questions look like?

[A]

Well, it's kind of, hey, here's everything we know, so we'll share. You know, we've got all the financials. We kind of know who's in the business. We might let him talk to someone who's senior in the business to get a bit of color on it. And from there, it's really. Yeah, what do you make of this? And, you know, a lot of what we had seen, he saw, too.

[B]

Oh, that's. That's reinforcing, right?

[A]

Yeah, totally.

[B]

Talk to me a little bit about how you use wealth to create a meaningful life. And some of the. You have some counterintuitive ideas around this that I think.

[A]

Well, it's been fascinating. I mean, really, only over the last couple years, I've been compounding so aggressively. I've been taking basically 80 or 90% of every cent I make and reinvesting it for a very long time. And over the last couple years, I finally kind of realized, like, hey, I should try and make my life more interesting, because if I just compound until I'm dead, that's kind of boring. And. And the typical path for wealthy people to make their lives interesting is buy a plane, buy a yacht, buy multiple palatial estates all over the world, Faberge egg collection, you know, get into sports cars, whatever it is. Those things I've found. I've tried a few of those, but they don't really fill me up. I don't find them that interesting. What I have realized that drives me is all I want, and part of the reason I like business is that I can just meet interesting people. And business is such a wonderful skill set because you can apply it to anything. So, for example, over the last two years, I've gotten into biology and health, and I can use money to talk to the world's expert on any medical condition or thing that I'm passionate about. I can just say, hey, I want to donate to your lab. Can I chat with you? Can I come visit? Can I come learn from you? I'll also bring interesting people to town. I mean, that's how we met. We. We hosted an event with Farnham street, like, five years ago. And we do that with all sorts of interesting people. And so to me, it's just about meeting fascinating people. And that's both globally, you know, events, travel, bringing people to Victoria, as well as trying to foster that in my own community. And what I've realized is that people seem to think that all the beautiful people are in, you know, LA and New York and all the most interesting people. But I realized that there's fascinating people here in Victoria, and they might be running a very radically different business than mine. I mean, I remember when I joined Entrepreneurs Organization, which is like a. It's kind of like YPO kind of thing. I was in a business group with people that ran a puzzle company, a woodworking shop, a popsicle business, a mapping company. Those are now some of my best friends. And. And I learned so much from just getting together with them. So those are the areas that I really invest in. And then separate from that, also just trying to manifest what I'd like to see in my own city. One of the beauties of living in Victoria is that there's not that many people really trying to make an impact here. And so, for example, I started a news business trying to replace the local newspaper here, which now is read by one in five people in Victoria. It's kind of the newspaper of record. Um, you know, I'm working on building a hotel right now. I own a whole bunch of restaurants. I really want to make a larger impact in the city. And when you're a big fish in a small pond, you can actually do that. So I'm having a lot of fun with that. But the answer is still hazy. Right. All those things are fun, but I still don't know what actually leads to happiness.

[B]

There's several rabbit holes we're going to go down here. One is why restaurants, which are notoriously not. Not great businesses.

[A]

So I have this whole thing about you got to hire the right. The wrong person before you hire the right person. And I've always been fascinated by restaurants and food. I started my career as a barista and working in restaurants, and I've always loved them. And I think every, you know, originally I was a designer, and I think every designer loves the idea of creating a physical space. If you've spent your entire life building ephemeral websites and apps that disappear after two years. The other. The idea of building something tangible is really appealing. And so maybe about seven years ago, I started a restaurant with a friend of mine. And it was a directional thing. I knew I wanted to do it. Everyone told me I was going to lose all my money, and I did. I lost almost a million dollars. And I hired the wrong people. We had managers that were. One of the managers was sleeping in the restaurant and drinking all of our beer, and employees were stealing, and the concept was all warped and our lease was bad. We made conceivable mistake. But, you know, Chris and I like to joke that we take forks and we stick them in electrical sockets, and then we learn and we start calibrating. And so what happened was I started learning the best practices of restaurants. And then about two years after that, I got approached by a guy who owned a bakery in Delhi, here in Victoria, where my brother had worked. I used to fix his computer when I was a kid. And he goes, I hear you buy businesses. Do you want to buy my deli? And I kind of went, okay, I kind of understand this. I know how to assess this. And when I looked at the books, I went, hey, this is a good one. You know, I had a bad one, but now I know what a good one looks like. And so I bought it. And I've just continued to take the money we made from that and buy more and more restaurants. And the idea is that we really want to buy institutions. We're not going to do a bunch of startup restaurants or something. We just want to make sure that the businesses and the restaurants in town that are. Are kind of iconic. Stay there.

[B]

I like that approach. Talk to me about the hotel.

[A]

Well, the hotel. I mean, it comes down to this idea of, you remember, like, 10 years ago, Portland became cool. And if you actually think about why was Portland cool? It was very simple. It was like Voodoo Donuts, which is like a funky donut shop. Everyone would go there and take photos with the donuts and talk about it and the Ace Hotel. And obviously there's a bunch of other reasons it was cool, but it kind of became a meme. Portland was this thing. And so when I thought about it, I was like, well, how do you do that in Victoria? How do you make Victoria cool? Maybe it's creating the Ace Hotel of Victoria. And so I just started talking to a friend of mine who's a real estate developer about that, and now we're working on it. And I Have no idea where it's going to go. I'll probably lose another million dollars or $10 million or something. But directionally I think that sort of thing is worth losing money on. And I think I can crack it over time. And if it results in the city being more interesting or bringing, you know, more interesting people here, it'll benefit the city, it'll benefit me. I like to meet interesting people. Um, so, yeah, I'm just kind of experimenting.

[B]

I like it. I'm eager to see the results of this. What's with this group that you get together with that you were talking about, the entrepreneurs group, where you talk about your problems? Walk me through that. Because that doesn't strike me as something that you would have signed up for and then enjoy as much as you do.

[A]

Yeah, so a friend of mine, so, so, I mean, I started my business about 17 years ago. Victoria is not a very entrepreneurial place. At least it wasn't then or I didn't know them. I was pipsqueak, 19 year old, you know, with acne all over my face. And I, I met some random guy and he goes, hey, you should, you know, you've got a business, you should join this thing. EO and I show up at some event they put on and it's all these guys who are in their 40s and they're wearing suits and kind of serious. And I just felt like I was out of place. And so as I was leaving, my friend grabbed me and he says, look, I know this seems kind of stiff, but just join this thing called forum. Just stick with this. And I kind of, I was like, okay, fine, I'll do one. And so EO has this thing where once a month you meet with six other entrepreneurs and you go into a room, you go into a conference room, usually at someone's office. And it's completely confidential, so it doesn't matter what it is. Could be you say you're going to Hawaii, or it could be that you're going to break up with your wife or your, you know, business is bankrupt or anything. Anything that's said in that room, completely confidential. And you give an update on your personal life, highs and lows, family life, highs and lows, work life, highs and lows. And it's kind of structured, so you go around in a circle. Everyone's on a timer, it's moderated. And at first no one trusts one another. Everyone's nervous, everyone's kind of puffing their chest and presenting the best. But you do this year after year after year. To the point where I'm still in a forum with one of these people. No, two of these people, 14, 15 years later, one of them is the executor of my will. Right. And so what you end up with is this kind of impartial board of directors and great friends that you end up bonding with. And I still do this. I have four of these groups. I do one a week. And in general, I'm just fascinated by the idea of structured conversation because it can take you places that you don't wouldn't otherwise go with people you think you know. So you know some of these people in forums. I've had great friends who I've been friends with for 10 years. I invite them into a forum and I learn what's really going on in their life. So I absolutely love it. I recommend more entrepreneurs. Try it.

[B]

What do you mean by structured conversations?

[A]

So, you know, right now, you and I could sit here and, you know, you put your book away and we just start shooting the shit. That's unstructured. You could have an agenda that would be structured. What I love is either having. Having prompts, so, for example, you know, the personal, family, business prompts, or actually using cards. And so I bought these boxes of cards from School of Life, and there's cards on friendship, on relationships, on family. And so when I. When I go out with friends to. For dinner, friends I've known for a very long time, sometimes I'll bring these boxes along and we'll draw cards at random, and it'll be, you know, deep, probing, weird questions. What's your greatest regret in life? In what ways are you dissatisfied in your personal life? What's something you want to do before you die? And it ends up creating these fascinating conversations that just go so much deeper than they would otherwise. I highly recommend everyone check those cards out. They're amazing.

[B]

I like that. Let's go up one level. We're going to come out of this rabbit hole in a second. But you're obsessed with biology and health. What have you learned?

[A]

I've learned that really, at the end of the day, one thing matters, which is exercise and eating well, obviously. Personally, I. Being an anxious person, I think it's kind of like porn for anxious people, right? You listen to health podcasts and you go, oh, my God, I need to take that supplement and I need to work out on this schedule. I need to do this form of intermittent fasting. Um, so I kind of. I think I like that. I like monitoring myself. I wear a glucose monitor. I wear My Apple watch, I wear oura ring, all that stuff. That's more me just kind of being a nerd and into that stuff. What's been really fascinating is over time as I've met more and more of these scientists and doctors, I've heard their frustration around certain things that are discovered in a lab but don't make their way into business. Right. They don't turn in, they don't become something that's in clinic. And, and so I've started funding science through my foundation for the last couple years. And that's been incredibly satisfying, realizing that, you know, you can apply a business skill set to biology and science and by being creative, you can achieve pretty incredible things. I mean one, one example, my friend, Dr. Rhonda Patrick, she told me about a study that needed funding out of UCSF where they have people with treatment resistant depression. They've tried everything, serotonin, reuptake inhibitors, tricyclics, you know, shock therapy, you name it. And they can't get over their depression and they put them in saunas for very, you know, very, very hot sauna session for an hour. They have a probe, rectal thermometer. So not, not very pleasant. But you do this brutal hour long session and with a few sessions they have, you know, major remission of their depression. And so you start thinking about that and going, wow, this is just a hot room, you know, with a hot box. Can you, you know, help people with treatment resistant depression? Think about how many people that can apply to. Now that's kind of an odd example, but that's something that I go, wow, that's amazing. I want to help validate that. I want to help that bring, bring that to the world because people that can't afford it can just go to their rec center and maybe they can help their depression. Right? That kind of stuff I find fascinating.

[B]

So, so you take this a bit to the extreme though. Like you monitor everything. At what point does that hinder your health? Like you wake up and you're like, oh, my sleep score is only 60, I'm gonna have a bad day today. Even though if you had not looked at that, you would have had probably a decent day.

[A]

I think it's a double edged sword. I mean I doing all that stuff last night we had dinner and because I'd had ice cream recently, I said, let's look at the dessert menu. And I ate two things of ice cream and I woke up this morning and I didn't feel great. And when I looked at my blood sugar, my blood Sugar had spiked all night. My heart rate had spiked all night. So to me, I might have woken up and gone, I don't know why, I don't feel good. And then I might have eaten ice cream again tonight because I had a bad sleep. I go, okay, I'm going to correct that behavior. So I think that's the good side of it. The bad side is exactly what you said where you, you get obsessed and you say, oh, I didn't take my, my vitamin D supplement today. I wonder if I'm going to get cancer. Right? It's, you know, all that stuff. I think a friend of mine put it well, he goes, the right amount of science reading and podcasts is 80, 20 spend, you know, an hour a month reading all the summaries and then don't think about it again.

[B]

Yeah.

[A]

And I think he's probably right.

[B]

That's sort of my approach, too. Like, once a week, I'll sort of, like, go into my eight sleep and I'll check my sleep for the week and try to make some correlations. But after you've made those correlations, like, you know, eating ice cream is going to cause you to have a bad sleep, and we're still going to do it tonight.

[A]

But the trick, yeah, probably the trick is, though, when I can talk myself into the fact and say, oh, I didn't sleep well for some other reason.

[B]

Right.

[A]

Because I saw it, I will go, I know for a fact, it's that actually I'm going to on camera right now assert, I will not eat ice cream tonight. I'm making a public declaration and you can shame me if I do. So, you know, you can create incentives like that. Right? Right.

[B]

But you will, you'll forget and you'll have it again next week or the week after. Or you went six months, a cold time, and then you, you went back to it.

[A]

Totally. Yeah. Like anything, though, just like my dopamine fast or taking that month off, you slip, right? So I went from fully refreshed. I was, you know, driving in silence, not listening to music, no podcasts. You two months go by, I listen to a podcast just like the chocolate cake example. That was the best thing I'd ever heard. But then four months go by and now I'm back down the rabbit trail and I need to do another one. Right. And the same thing is true with any kind of addiction. I think I just hope that I'm never doing something that is so addictive that it ruins my life. Right.

[B]

What scares you the most with health?

[A]

Well, I have chronic acid reflux. And I worry that I'm going to have esophageal cancer. That's my. Whenever, because I'm anxious, whenever I get it, I go, okay, I have a 1 in 800 chance of getting esophageal cancer. Right.

[B]

And so it's always in the back of your mind.

[A]

Yeah.

[B]

Coming out of the rabbit hole a little bit here and going back to sort of wealth. Let's talk, how do you raise kids with wealth?

[A]

Yeah, I think it's a really difficult thing because they talk about this idea of immigrants to wealth. So I'm, you know, I, my extended family, my mom came from a well to do family on the west side of Vancouver. Vancouver is very affluent and she came from a wealthy family, but the money was kind of gone by the time she was an adult. And so she liked that world. She knew all of the players, she liked living on in a nice neighborhood, but she wasn't rich anymore. And I think that was really difficult. So what my parents ended up doing is even though my dad was a struggling architect and had a very small income, they bought the worst house on just the outside catchment area for the best public school in, in the city. So I ended up going to school with all these really, really rich kids. And that, that made me, I was like, I was a secret. I, I knew how to speak the language, but I was kind of an immigrant. I didn't have any of the things they had and I wanted all those things and then I fought for it. So I, you know, I, I went out, started all these businesses, was hyper focused on getting all the things I thought I wanted that all the rich kids had. I got those things. My kids will be those rich kids and I don't know how to create in them that same kind of feeling of, of drive or hustle yet. And I think at the end of the day, you know, as we talked about last night, the idea of making your kids work to achieve things and driving home that, you know, this is something I have, you're coming along for the ride, but you actually need to start fresh. But I don't know. And I'm really struggling with it, to be honest, because I see examples in friends where they grew up around a lot of wealth and their parents basically said, yeah, you're going to inherit everything and you have a great responsibility. And they've turned out amazing. And I've seen it work terribly. And on the flip side, I've seen people cut off their kids and say, go earn everything yourself. And it doesn't work out and they resent them. And then it also works really well. At the end of the day, I think you just need, your kids need to know that you're there and you love them. And I hope that's enough.

[B]

I hope so too. Yeah, but how do you think of like spoiling them and the opportunities available to them and sort of like the type of person they become when they're surrounded by so much?

[A]

Well, I think my greatest hope is just that they. When I was growing up, I didn't have a love of learning. So when I went to school, I wasn't inspired by the teachers. They, they, they all seemed kind of miserable, right? They all seemed a little depressed and they didn't really explain to me why I'd want to use the tools they were teaching me. And so I really hated school. I kind of stopped reading in high school and only by chance I kind of started. When I started getting into business, I picked up a book again because I was so desperate, I was so clueless about what I was doing that I started reading. And thank God I did because I ended up having a love of learning and realizing I could read about anything I wanted and going down that path. And I was always very. While I started my business at, you know, 19, I, I do have a regret of not getting to go to university and having that kind of knowledge vacation that so many people got to have. And so I hope that my kids can love learning in elementary and high school and maybe go to college and have those four or five carefree years learning whatever they want. And then if they want to be, you know, a Greek scholar or something, they can do it because they don't have this subsistence farmer whipping on their back where they, their thing they have to make money. But it's, it's, it's a fascinating question.

[B]

I always envy those kids who had four years of like learning in university. I remember struggling between a full time job and full time school and like failing at both at several points and being envious of people with all their free time and the frat parties and all of that stuff. Just enjoying life.

[A]

We have to appreciate it by watching American tv. Now I'm going to live, watch euphoria and go, oh, that could be been me.

[B]

The fund, you mentioned the fund. What's it been like? Because this is your, you know, we, we've done joint deals for a while, but like this is your first sort of like big fund with lots of investors. Talk to me about the pros and cons as you've, you've seen them.

[A]

Well, what happened was that when Covid hit in March 2020, Chris and I looked at each other and we went, oh my God, this could be something where there's, you know, every startup in the world is going out of business. I think there's, you know, going to be a lot of deals to do. And we went out and raised the fund. And to be honest, I mean, like I said, we've, we've been building the business for 17 years. We've been compounding our capital at, you know, very high rates and we built up a great network of people, but we never asked them for anything. And so finally when we said, hey, we're going to raise this fund, we had immediate demand from all sorts of incredible investors and we raised this 200 million dollar fund and then we did nothing, Covid, you know, I mean, the Fed kicked in, the markets went back up, there was crazy irrational exuberance all around. And so we were, you know, we were going, oh my God, did we make a mistake? You know, we frankly didn't need to raise the fund unless there was a big, a big opportunity. And there's a lot, you know, a lot of distress. And so we did nothing for about a year. And then we bought aeropress. We just did another deal that we haven't announced yet. Psychologically, I think it's been good for me to know what it's like to be a good partner, how to be, you know, I'd obviously had partnerships with you and others before, but to really understand that kind of limited partner and investor dynamic because I now invest in funds, right? So I think it, you know, you become better by doing the thing that you, you want to do. I'm a better businessman because I'm an investor. Better in this investor because I'm a businessman. Same thing with fund management. But psychologically, I think over the very long term, I don't like owing people things or letting anyone down. And so I don't know that I'll raise another fund. All of our investors have been wonderful. We've had no issues. People have been very supportive. We've done good deals. They're all probably going to make a lot of money. But I don't think I want to be in the fund management business. I'm somebody that when I lose money, I want to lose all my own money. Right? When I lost money, doing the pizza restaurant didn't phase me at all.

[B]

No other investors.

[A]

But if I had raised money for that, I think I would be really, really struggling psychologically. So for me, that's been. That's been interesting.

[B]

Do you know who else I heard talk about that recently was Bruce Flatt from Brookfield. And what he said is, we always prove the concept internally with our own capital before we ever invite other investors into the deals.

[A]

He's super smart.

[B]

Yeah, they're. They're really turned on. What do you do for your. Your public investing? Are you okay disclosing that? Like, what do you. What do you do outside of sort of the companies that you own in the public markets?

[A]

Yeah, I mean, I. It's really funny. So. So I started Metalab. I took the profits from Metalab, and I started a variety of other businesses. And one in particular worked really well, which was Pixel Union, which was a partner to Shopify. I met Toby and Harley from Shopify that now today is a public company. But a lot of the businesses I started failed. So I mentioned flow, lost 10 million bucks. I started a online DJ, school cat furniture business, skin care company, all sorts of silly stuff, kind of sticking forks and electrical sockets and learning. And then what ended up happening was in 2013, I sold my first business. I was kind of burnt out, and a friend of mine just said, hey, look, why don't you just sell one? Take some money off the table de risk a little bit. And so I did that. And. And suddenly I had, you know, over $10 million sitting in my bank account. I had businesses that were spitting out profits. And I started reading about Warren Buffett. I didn't really know anything about him. I just knew that he was a smart investor. And I'd always thought stocks were boring. You know, it's gambling. Didn't understand it. And when I read about Buffett, everything just kind of clicked for me. The idea that you could be one of the wealthiest, most successful people in the world, but you could delegate out everything to CEOs and managers was fascinating. And so at first, I applied that lesson by creating Tiny, our holding company, spinning out all of our businesses, and hiring CEOs. But I started considering, you know, really acquiring businesses and investing in the public market. And for a while, I became fascinated by it. But. But I realized that the private markets were far more inefficient. There were much better deals and opportunities, specifically in our niche where there was all these founders that owned exceptional businesses they wanted to sell. But to be blunt, they didn't want to sell to some Wall street douchebag. Right? We would have people try and buy our businesses, and they would show up bragging about their assets under management. They're wearing gold cufflinks, they're wearing gucci shoes, suits. They speak about ebitda, all these terms that founders don't care about. A founder wants to know, how much am I going to get? When. When am I done? Am I. Are my employees going to be taken care of? Are you going to embarrass me and destroy my business, or will it exist in 10 years? And so we could go to them and say, hey, look, we're normal people. We'll buy our business. We're not going to change anything. Your employees will be happy, and we're going to hold for the long term and continue to run it sustainably. And that really resonated. And so we started buying these private technology companies. And so I didn't really think about the public market after that very much until I discovered pershing square holdings, which I know both you and I are investors in. And I'd kind of followed Bill ackman from a distance and watched him on YouTube, and I just found myself always nodding along. I love the way he communicates. I find him quite fascinating. And I ended up watching that stock. So he has this publicly traded holding company, which effectively is just a holding company that owns a bunch of stocks, and it owns chipotle and, you know, hilton and howard Hughes and, you know, a bunch of very conventional blue chip businesses. And I realized that it was trading at about a 30% discount to net asset value, which means that if there's $100 of stocks, it was trading at $70. And so I went, oh, wow, that's an incredible bargain. And I think bill's really smart. But to diligence Bill, I really wanted to meet him. And so what I ended up doing is I spent $60,000 bidding on a charity lunch where I'm like, okay, I get to donate charity. I get to meet this interesting guy. And my plan was that if he was an asshole, I would sell all of it as soon as we got out. And if I liked him, then I'd keep it and maybe buy more. And so I ended up meeting Bill, and Bill just blew my socks off. We just totally hit it off. We spent like three or four hours meeting each other. I ended up meeting the whole team at pershing Square, and I really, really liked him. And at the end of the lunch, he also said, hey, look, you know, I know you invested in my thing. I'd love to invest in anything that you do, so nudge me if there's ever the opportunity. So he Ended up investing along with you in WE Commerce, which is our public company focused on Shopify. He invested in our fund. We've done a couple other deals together. So basically, Bill is my only public holding. So that's my kind of backup retirement plan. I just keep stocking my money in Pershing and let Bill handle the public investing. And he's done pretty incredibly well over the last two years. He had one bet where he bet $25 million, and it turned into, what, 2.5 billion or something?

[B]

Yeah, I remember you and I were texting about this in March 2020, right in the world, and they have to publish their net asset value weekly. And he had said that he put on this asymmetric hedge, and you could see as the markets were tanking, the net asset value was increasing even though the share price was decreasing. And it just got to these absurd levels. I think at one point it was about 50% of sort of like nav.

[A]

It's crazy. I wish I had invested more.

[B]

Yeah, you and me both. You mentioned Pixel. So Pixel became E Commerce, but, like, you sold it and. And then after that, how did you feel? And tell me the story about reacquiring it and then walk me through going public.

[A]

Yeah, so I was on a walk in 2013 with a good friend of mine, and I was just saying, you know, I'm overwhelmed every day wake up and there's, you know, a million people grabbing me, and I. I just have endless problems. And he stops me on the path and he just says, look, why don't you just sell a business? And so I said, well, I've never done that. I don't know how that works. He ended up introducing me to an investment banker, and we ended up selling the business to a family office in Vancouver. And the family office in Vancouver took over the board. I kept 20%. And so I kind of stayed involved in the business. I helped them choose a new CEO, who I really, really love, this guy named Ben Moore. And Ben did an incredible job. He just kept growing the business. And the family office decided that they wanted to get out of owning private businesses. They kind of signaled that to us. And so two years ago, we said, look, we love the business. We obviously know it intimately. We would love to buy it back. And so we ended up buying it back from them. And we started a new holding company called WeCommerce. So We Commerce, owned Pixel Union, and then we started making more acquisitions there. And the thesis was very simple. You know, we're not macro traders, but we knew that E Commerce was on an upward trend. That was just very obvious to us that it would double or triple over the next 10 or 20 years. And we knew that Shopify was the best platform for independent retailers. We knew that over the long term people are always going to want to control their data. They weren't going to want to be only on Walmart or Amazon or something like that. And we felt they were the best platform. We looked at all of them and we also had been there super early. We had great relationships with Harley and Toby. And so yeah, we started acquiring businesses in that space. Bought a company called 460 and then we took it public via a reverse merger which is kind of like the baby version of a SPAC up here in Canada. And it was crazy. I mean, got to go on cnbc and you know, me and Bill worked on it a whole bunch with you and you joined the board and so been this crazy experience. So yeah, it's been, it's been wild.

[B]

Would, would you change anything about that? Like what have you learned through that process as you think about taking companies public or running a public company? And by running, I don't mean sort of like the day to day CEO, but obviously you're on the board and you're a major shareholder.

[A]

I think that Charlie Munger has been fascinating to watch from a distance with the way he runs Daily Journal where he doesn't overdo all of the crafty public company stuff. He really just focuses on allocating capital well and buying great businesses. And so we've focused on the same thing. And I think in the early days, just like my example of starting the restaurant, we had a very successful reverse takeover ipo, but we had no idea what we were doing. I mean, we were learning on the job multiple times. Bill kind of grabbed us and was like, what are you guys thinking? Like, of course you have to do it this way or communicate it differently and stuff. So when you do something for the first time, it's just incredibly stressful. Now we're working on other go public opportunities. We have a playbook. We know what kind of CFO we need to hire, we know how to structure the board. We just have that, that rep is kind of done. The muscle is built. So it's more, it's more that, you know, if I could go back, I'd tell myself all the stuff to do better. But overall I actually think it's gone very well.

[B]

Do you find that like you get a mark on that every day now, right? So like you're in a Way that was non visible before. So you, you don't have like all these other businesses you own. You don't get this like your house, right? You don't get a note in the mail every day saying it's worth X today. Has that had any impact on your psyche?

[A]

Well, I think tickers in general make you miserable, including, you know, a Dexcom glucose monitor and Oura ring. It's that same effect. And I generally, you know, it was, it was a total trip. I mean, my net worth would increase or decrease by $20 million on any given day. And that scared the hell out of me. But once I thought about it, I realized that unless you're selling, it just doesn't matter what the stock price does. And that over the very long term, as long as you grew the earnings of the business, the market price will probably reflect that. So now I don't even look about it. I don't look at it, I don't really think about it. I maybe look at it once a month or something like that, but for the first three to six months it really slapped me in the face. And frankly, it forces you to kind of contend with like, hey, you're, you know, hey, you're rich. Like, you know, we had hundreds of millions of dollars of stock, which I've had in private businesses, but like you said, there's no ticker. You just make up evaluation and you know, it just, it's paper money. It's very different. Um, so it affected my psyche in terms of making me realize like, oh, wow, we've built this big business that we didn't quite realize was so big.

[B]

You know, do you have any forcing functions in your life that sort of put you on the path to success? Like, what are the little things that you do that sort of like guarantee that you have a good day or put you in the best possible position to succeed?

[A]

I think the biggest thing that I look for now in anybody that I work with that made, made things work for me was a crazy sense of pace. So I have a lot of habits, but you know, one of them, so I just did it on camera, is asserting to friends, hey, I'm doing this thing right. So if I have an idea, I will actually just start talking about it. That boutique hotel idea, I started talking about that three weeks ago. It's still a PDF and we have an architect kind of going through plans. I'm going to start talking about it because talking about it makes it real. Giving something a name, making a logo. I'm very good at that kind of 0 to 1 and pushing that forward. And that's been incredibly helpful for me. I also think this idea of hiring the wrong person first. Right. I see this so many times with young entrepreneurs where they go, I need to hire a VP of marketing. And they labor over it for eight months. And I just go, God, you should have just hired the wrong person first. And then you can learn, you know, you can let them go if it's not a fit, but just get moving. So many people, they try and use that saying that carpenters use measure twice, cut once, but they just end up perpetually measuring.

[B]

Yeah. And it prevents them from like taking any action. Right. Like, and then the longer you, you're inactive, the sort of, the longer it goes before you, like, the harder it is to start being active.

[A]

And it's not real. Right. It just goes back to like, there was so much value. Even though I lost a lot of money on that restaurant, there was so much value in saying I'm a restaurateur. Right. Like, stupid as it is, it's like you just, you make it. And same with, you know, doing the foundation or anything. I was like, I am donating money to science. Even when it was like 10 grand, I just started talking about it and making it real.

[B]

Because then you're attaching it to your identity too. Right. And then you want to succeed.

[A]

Totally. So it's those kind of, I think a lot of those kind of hacks of like not letting ideas die on the vine, forcing it to become real, creating social shame if I don't actually execute on it. And again, that's a double edged sword as well because you get into consistency and commitment. There's been businesses that I've talked about publicly that were stupid and I shouldn't have done and I feel the need to continue them on because I've shared it. But most of the time I think.

[B]

That is very effective when you're stressed. Like, what is the most important thing to remind yourself.

[A]

That I'm probably under, under, slept. I find that when I'm tired, a pebble turns into a boulder. And when I'm tired, when I'm well rested, a boulder turns into a pebble. As long as I'm surrounded by good people, no problem. You could tell me right now, you know, all your businesses are bankrupt. If I'm well rested, I will be kind of excited. I'll, you know, I'll be in warm war CEO mode, but I'll be kind of pumped up. If I'm tired, I'll Just start crying, right? I will just be a wreck. So that, that's a huge thing. I think. You know, physiology defines almost everything. At the end of the day, we're just bags of chemicals. And if your chemicals are wrong, you're not going to feel good. Everything in your life can be right. But like, you know, the example when I Woke up on August 1st, you know, I made hundreds of millions of dollars that year taking a company public. I'd met all my business idols, had a great life, two healthy kids, you know, you name it, and I was miserable. And that was because my physiology was off.

[B]

I find it interesting because, like, I know that sleep is important to me, but. But I also can't in the moment. I don't feel like I'm responding based on sleep because my mind is like, oh, like you're, it's not that you're tired that you're responding this way. It's just the situation sucks. Or like, you know, you make, you take that pebble and you make it into a boulder. And so like one of the things during COVID for me is like just routine, like sleep.

[A]

Totally.

[B]

And it's totally like ritualized for me now almost.

[A]

Well, you have, you have kids and they're a little older now, but I have a 2 year old and a 4 year old. So they're very recently babies. And, and one of the things I think everyone realizes when they have a baby is that if bedtime is at 7, you put them down at 7, because 727 30, that's going to be a really bad night for you.

[B]

Yeah.

[A]

And what I realized was, oh my God, I'm just, I'm the exact same. So now I try and have a ritual where, you know, at this time I watch TV and at this time TV goes off. Then I read a book, then, you know, I turn on a low light and I'm always asleep at exactly 9:30 every single night. And like last night I broke it. I stayed out late chatting with you and ate ice cream, got home late, started talking to my wife, couldn't sleep until 11:30. Right. So I think it's just about this concept of there's a. There's a really great Stanford doctor named Dr. Anna Lemke, and she specializes in addiction and dopamine. And she talks about how you are not strong enough to not eat the bowl of ice cream. So if you put the bowl of ice cream in front of me, I'm going to create. My brain's going to create every reason to eat it. So what you have to do is self bind. You have to remove that stimulus from your life completely. Can't be in the house, can't have easy access, you know, don't ask for the dessert menu, etc. And so I just try and self bind. I just try and create an environment where I just can't do those things. And as soon as I'm given, you know, I'm like a hamster. If you put those things in front of me, I'll go down the maze.

[B]

Well, I think we all are. Right? And so, like, your unconscious mind is way more powerful than your conscious mind, and it's driving your behavior most of the time. And so you need these sort of, like, rules, environmental impacts. For like, not like a rule, for example with ice cream is I don't eat ice cream, then I'm not making a decision every time that I'm out for a meal. Which is very different than using willpower, which I think is overrated. Like, we all think we can plow.

[A]

Through this, but, like, well, I did this. I wanted to eat a good diet, and I said, okay, I'll do the Paleo diet. And I went to my best friend and I said, look, I want you to come up with a shame. I want you to come up with something embarrassing. And if your job is, if you catch me, I have to do this. And so he found this really ugly baseball cap that said wee wee baguette. Right. And it's like, just stupid. Like, if I saw someone wearing this hat, I'd be like, that guy's an idiot. Right. And I didn't break because I didn't want to wear the hat. Right. Just creating these little incentives for yourself can be incredibly effective. And I think, you know, you've had that fascinating interview with Daniel Kahneman, and he in that interview says, I know all these things. I still can't prevent myself from being affected. You know, I'm sure that if you. I know, for example, all about price anchoring and negotiation, but over and over and over again, I find that if somebody anchors me low and then, you know, sends me a number that's higher, I feel like I've won. Right. I can't remove that from my brain. And so what I have had to do in my personal life is turn on screen time on my phone. Yeah. And give my wife the passcode. Not have ice cream in the house. You know, all those things. Treat myself like a, you know, alcoholic or something. When it comes to these stimulus devices.

[B]

What'S been the toughest negotiation you've ever been part of.

[A]

Well, the. The hard ones are not always the ones that take a while. I always think that when there's good people at the table who are just emotional, that's fine. Right. What's hard is when you have people who are acting in bad faith and manipulating. And so, you know, we've had negotiations where there was a. You know, it seemed like a good deal, but it was with bad people. And it was more just dealing with bad people, dealing with the cognitive dissonance of somebody lying to you or something. I find those very uncomfortable. But, for example, I just did a deal with a founder, and he was very emotional, and he snapped at me a couple times. Like, there was moments that were quite strained, and people on my team said, we shouldn't do this deal. And I said, no, no, no. He's a nice guy, but this is his baby, and he doesn't want to sell his baby to someone who's going to mistreat it. And you know what? We should have followed through on our word. You know, we had said we'd deliver him something by this date. It took us a little longer. He got angry. That's okay. That's good faith. What's hard is when somebody is manipulating you, acting in bad faith, obscuring numbers, going legal, you know, all that kind of stuff. And I've had enough experiences with that stuff that, you know, Munger has that great saying when you. When you find yourself over a stinky sewer, just plug your nose and keep walking. You don't need to climb down. Right?

[B]

Yeah. You don't need to make. You can't make a good deal with bad people.

[A]

Totally.

[B]

And even if in the moment it looks great, it always, inevitably backfires.

[A]

Yeah.

[B]

Tell me about how you want to be remembered. Like, what is success for you? And what do you want people to say about you when you're 90?

[A]

I just want. I think I just want my kids to love me at the end of the day. I know that's kind of cheesy, but, like, if I actually go to the core of it, I don't care what people say about me after I'm dead, because I'll be dead. But my kids are part of me. Right. And I want them to know that they were loved and taken care of. That. That's about it. Honestly, I used to be. I remember sitting down with my dad. My dad is very entrepreneurial. So he. When I was a kid, you know, I would start a lemonade stand, and he'd say, okay, great. Now what? And I'd be like, what do you mean? I have a lemonade stand? And he'd be like, no, no. Like, why don't you start three locations and we'll hire kids. You pay them. Pay them five bucks, and then you make seven bucks. And, you know, he always was pushing me forward to entrepreneurial stuff, but he personally doesn't necessarily. He's not entrepreneurial. He's just read all the books and stuff, right? And he, He. I remember sitting down with him and saying, dad, like, you know, did you ever just want to get stupidly rich? Like, did you ever just want to see your name on a building or whatever? And I remember him saying, like, oh, no, I don't have an ego. I don't need to do that. And I kind of. Early on, I wanted all that, right? I was like, I want to have a Ferrari. I want to have a mansion. I want, you know, I want to have my name on a building. All that stuff. And then I realized that that stuff is all filling a hole in your heart, and it doesn't do anything to you, you know, wouldn't satisfy you in any way. And in fact, it actually just puts a target on your head, right? Everyone loves to hate on the person that is the loudest. Who. What's that? Great quote. The tallest blade of grass is the first to get cut. And then the other one I like is whales only get harpooned when they surface. And so I think being loud in the wrong ways and, you know, inviting people to think you're an when you're not. I just want to avoid all that stuff.

[B]

I think that's a great place to end this conversation. Thank you.

[A]

That was awesome.

[B]

Thanks for listening and learning with us. For a complete list of episodes, show notes, transcripts, and more, go to to FS Blog, Podcast, or just Google the Knowledge Project. Recently, I've started to record my reflections and thoughts about the interview. After the interview, I sit down, highlight the key moments that stood out for me, and I also talk about other connections to episodes and sort of what's got me pondering that I maybe haven't quite figured out. This is available to supporting members of the Knowledge Project. You can go to fs, check out the show notes for a link, and you can sign up today and my reflections will just be available in your private podcast feed. You'll also skip all the ads at the front of the episode. The Frontam street blog is also where you can learn more about my new book, Clear Turning Ordinary Moments into Extraordinary Results. It's a transformative guide that hands you the tools to master your fate, sharpen your desire decision making, and set yourself up for unparalleled success. Learn more at FS Blog Clear until next time.