Businessman and investor Andrew Wilkinson has made a successful career out of channeling his entrepreneurial spirit, but he knows that sometimes that energy can be a double-edged sword. On this episode, Wilkinson goes in-depth on the lessons learned from a career that’s seen him build a business empire of nearly 40 companies, but also why he’s had to re-calibrate his personal goals after struggling to find happiness in the summer of 2021. He also discusses mimetic desire, building a business in a small Canadian market, competing with venture-backed companies, strategies for hiring CEOs, the mistakes that have cost him millions of dollars, and so much more.
Wilkinson is the co-founder of Tiny Capital, which owns over 35 different companies including AeroPress, MetaLab and Dribble. He is also the co-founder and chairman of WeCommerce, a holding company that starts, buys, and invests in the world’s top Shopify businesses. He is based in Victoria, British Columbia.
Here are a few highlights from our conversation:
I find every entrepreneur has that inherent drive where they have to achieve, and even when it’s not really necessary to achieve.
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.
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?
I think 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 the example, when I woke up on August 1st, I made hundreds of millions of dollars that year, taken a company public, I’d met all my business idols, had a great life, two healthy kids, you name it, and I was miserable. And that was because my physiology was off.
And so much more.
Timestamps:
00:00 – Intro
00:37 – Andrew’s dopamine addiction
04:48 – On mimetic desire
06:58 – What Andrew’s working towards
09:13 – Your strengths = your weaknesses
13:46 – Advantages of being in Canada
16:14 – How Andrew runs his company
19:08 – Lessons learned from hiring CEOs
25:18 – How Andrew uses wealth to live his life
31:48 – Andrew’s community
35:28 – What Andrew’s learned about biology and health
40:50 – How to raise kids with wealth
48:32 – How Andrew invests in public markets
54:00 – The history of WeCommerce
56:22 – On running & taking a company public
59:15 – Andrew’s habits for success
01:01:49 – How Andrew deals with stress
01:03:05 – Other self-improvement hacks
01:06:44 – Toughest negotiation Andrew was been a part of
01:08:23 – What success looks like for Andrew
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