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.