My First Million Podcast #65 — Q&A with Andrew Wilkinson (Co-founder, Tiny)

Release Date: April 15, 2020
Host: My First Million, HubSpot Media
Guest: Andrew Wilkinson

Episode Overview

This special AMA (Ask Me Anything) episode features Andrew Wilkinson, co-founder of Tiny, answering audience questions submitted via Twitter. Andrew shares candid lessons from building and acquiring companies, investing, hiring, reading, and more. Sam Parr and Shaan Puri mostly step aside, letting Andrew provide deep, unfiltered insights into business, investing, and personal growth.

Key Discussion Points & Insights

1. Sourcing and Hiring Great CEOs

[01:35]

• Andrew describes a two-fold method for sourcing CEOs:
  • Internal referrals from trusted executives and CEOs in their network.
  • Hiring proven operators: experienced leaders who have already succeeded in similar roles or industries.
• Quote:
  “If you were going to go and build a new deck on your house, you wouldn’t hire somebody who you thought could probably figure it out... you would go and hire a red seal carpenter who had built hundreds of decks.” — Andrew ([03:14])

2. Inspiration from Buffett and Munger

[05:35]

• Andrew is a huge Warren Buffett fan but is “far more fascinated” by Charlie Munger, who popularized the concept of a “latticework of mental models.”
• He explains incentive-caused bias, using share buybacks as an example of misaligned incentives.
• Listens to and recommends both men’s speeches and writings.
• Quote:
  “Munger has what he calls a latticework of mental models... ways of thinking about problems that help you shortcut your thinking so that you can say, oh, that’s one of those.” — Andrew ([06:10])

3. Company Building: Art or Science?

[10:15]

• Starting companies is “kind of black magic” and involves a lot of guessing, but growing companies is highly repeatable with common best practices.
• Emphasizes pricing strategy, marketing basics, incentive-driven performance, and negotiation as universal levers.
• Quote:
  “Brent Beshore from Permanent Equity calls it the ‘everything tastes like chicken’ part of business.” — Andrew ([11:17])

4. Recommended Biographies

[13:54]

• Andrew shares favorite business and sports biographies:
  • Shoe Dog — Phil Knight
  • Buffett: The Making of an American Capitalist — Roger Lowenstein
  • Tiger Woods — Jeff Benedict
  • Open — Andre Agassi
  • The Gambler — William Rempel
• Gives context on the value of seeing behind-the-scenes sacrifices in biographies.

5. Biggest Failure: The Restaurant Venture

[17:16]

• His foray into the restaurant business was a humbling, expensive failure; underestimating operational difficulty and the realities of low-margins.
• Valuable lesson: brick-and-mortar is very different from scalable tech.
• Quote:
  “The difference between making money and losing money in the restaurant industry is like how many towels you buy for the bathroom.” — Andrew ([20:56])

6. Key Personal Attribute in Hiring

[22:20]

• Prioritizes scrappiness; looks for urgency and the drive to overcome obstacles.
• Scrappy people are great for early-stage, but he balances them with “Steady Eddy” types for long-term execution.

7. Making Entrepreneur Connections Outside Tech Hubs

[23:22]

• Living in Victoria, Canada, he connects with both tech and non-tech entrepreneurs, finding universal challenges.
• Advocates for cold emails; shares a story about meeting Dan Gilbert (Quicken Loans) through a simple outreach.
• Quote:
  “I’ve gotten pretty good at figuring out what people’s email addresses are... I’ll just write them a two line email...” — Andrew ([25:20])

8. Investing Approach: Own Capital vs. Outside Money

[27:00]

• Majority of Tiny’s investments are with their own capital; limited outside investors for larger deals.
• In the process of raising a fund to tackle more opportunities given market changes.

9. Growing Design Agency (MetaLab) and Getting Clients

[29:13]

• Focused on doing exceptional work, sharing it publicly, and being slightly controversial (e.g., open letter to Zappos CEO).
• Targeted high-quality clients from the outset, not “working their way up.”
• Quote:
  “If you want to work with the world’s best companies, you need to start by working with the world’s best companies and really focusing.” — Andrew ([31:31])

10. Reading Habits and Advice

[34:18]

• Loves Buffett’s advice to read 500 pages/day, but admits that after becoming a parent, most of his current “reading” is via Twitter, audiobooks, and before bed.

11. Personal Evolution and Perspective

[36:15]

• Once obsessed with external rewards (clothes, travel, possessions); discovered happiness was more about routine, family, friends, and community.
• Observes his Persian grandmother-in-law’s massive dinners and vibrant family as a happiness template.
• Quote:
  “She’s cracked the code... she just looks happier than anybody else.” — Andrew ([41:31])

12. Building Capital from an Agency

[43:35]

• Benefited from servicing SF-based companies while being based in Victoria, allowing for higher margins due to lower costs.
• Remote work and location arbitrage proved pivotal.

13. Delegating — From One Business to Many

[45:10]

• Effective delegation relies on tolerating initial mistakes, then empowering others once they are trained.
• Formula: Trustworthy people + aligned strategy + proper incentives.
• Quote:
  “I call that the delegation barrier... when I broke that down... I realized that I could just teach somebody something once or hire somebody who’d already done it and let them do that thing.” — Andrew ([46:32])

14. Most Critical Lesson for His Kids

[48:14]

• Wants his kids to develop the instinct to teach themselves anything—Google, read, watch, experiment, and iterate.

15. Frustrations Building a House

[50:02]

• Highlights incentive problems with the general contractor “cost plus” model; contractors are incentivized for the project to go over budget.

16. Advice for Skipping the Agency Step

[52:15]

• Warns that success as an investor requires hands-on business experience. Avoids “spreadsheet business” thinking detached from reality.

17. Best and Worst Business Advice

[54:02]

• Worst: Taking blind, massive risks when young (e.g., betting all on startup stock options).
• Best: Build a boring, profitable business first; get into the habit of regular reading and learning.
• Quote:
  “There’s no greater freedom than having your rent and your food and your basic needs taken care of, especially in a business that’s easy to run or automated.” — Andrew ([55:56])

Notable Quotes & Memorable Moments

• On delegation:
  “Teach a man to fish and he’ll eat for a lifetime. I think the same is true with delegation.” ([45:55])
• On risk:
  “I really just don’t think that they [young people] would do it if they understood the true odds. They’d never buy a house that had a 95% chance of failure.” ([54:14])
• On biographies:
  “One of the things I love about biographies is that often all you see is the success... what you don’t see is the sacrifice.” ([14:18])
• On family:
  “All that matters is friends, family, kids, day to day habits, community.” ([40:18])

Useful Timestamps

| Topic | Time | |-----------------------------------------------------------|--------| | Sourcing/Hiring CEOs | 01:35 | | Buffett vs. Munger & Mental Models | 05:35 | | Repeatability in Company Building | 10:15 | | Book/Biography Recommendations | 13:54 | | Biggest Failure: Restaurant | 17:16 | | Core Hiring Attribute | 22:20 | | Connections Outside Tech Hubs (Dan Gilbert story) | 23:22 | | Investment Sourcing: Own vs. Outside Capital | 27:00 | | Agency Client Growth & Marketing | 29:13 | | Reading Habits | 34:18 | | Personal Evolution (Materialism to Meaning) | 36:15 | | Building Agency-Generated Capital | 43:35 | | Delegation Mindset Shift | 45:10 | | Lessons to Instill in Kids | 48:14 | | Frustrations Building a House | 50:02 | | Jumping Directly Into Investment Holding Companies | 52:15 | | Best/Worst Business Advice | 54:02 |

Episode Tone

Conversational, candid, and practical. Andrew shares stories and advice with humility—emphasizing lessons learned, mistakes made, and actionable wisdom. The tone remains informal and approachable, peppered with personal anecdotes and humor.

In Summary

Andrew Wilkinson’s AMA delivers a treasure trove of practical insights for entrepreneurs, business owners, and aspiring investors. His pragmatic approach—learn from direct experience, focus on incentives, delegate, avoid unnecessary risk, and read voraciously—provides a grounded roadmap for success. Whether you’re building your first business, aiming to scale, or just refining your personal philosophy, there’s plenty of actionable advice throughout this episode.