Andrew Wilkinson built a successful design agency in his early 20s. But in 2008, the stock market crash, paired with an untimely client refund request, nearly wiped him out. At 27, he sold his business for $7M. He's since built a $200M+ stake in WeCommerce alone, co-founded Tiny, and authored Never Enough: From Barista to Billionaire.
Hear Andrew’s financial ride, why he says an anti-anxiety med has helped him more than any amount of money, and his thoughts on giving it all away in this week’s episode of MoneyWise.
Listen— and check out the recap— below.
HERE'S MY TAKE
In his early 20s, Andrew Wilkinson started a design agency.
His income grew rapidly: "Whatever was left over at the end of the month went to me. Over time, that became $5,000, then $15,000, then $30,000, then $50,000. The number just kept increasing, and it reached a point where I couldn't spend it all, and I had to figure out what to do with it."
Andrew's Financial Journey
- Built a successful design agency in his early 20s
- At 27, sold a business for $7 million
- Experienced significant losses, including a near-bankruptcy in 2008
- Built a portfolio of businesses, including WeCommerce, which after going public, left Andrew's personal stock worth over $200 million
The Reality of Sudden Wealth
Andrew's first experience with substantial liquidity came at 27 when he sold a business for $7 million.
He recalls: "I remember going to the ATM, printing out the slip, and seeing this huge number with a bunch of zeros on it. I thought, 'Oh, my God, I'm done. I can retire. I can do anything I want. I never have to worry about money again.' Obviously, that's not what happened."
This moment marked a shift in Andrew's spending habits, but he discovered that many of these luxury items didn't provide lasting satisfaction.
What's Worth Spending On (And What Isn't)
Reflecting on his spending habits, Andrew said: "I would be so excited to buy a new laptop a couple years before. Suddenly, I just bought a new laptop because I felt like it, and it was kind of empty. I was very consumeristic, and I'd go on these shopping sprees, get home, and think, 'What am I doing? Why do I have all this stuff?'"
However, he did find value in certain investments:
- A beautiful primary residence: "There's something really lovely about investing in an amazing space for you and your family."
- A nearby lake house: "Not because it's a second house or flashy, but because it's not about anything except for family and friends."
- Private air travel: "There's something just so magical about rolling up and getting on a plane and going."
The Mental Health Aspect of Wealth
Andrew shared a profound insight about the relationship between wealth and personal well-being:
"Wealth is a little bit like travel. Everybody fetishizes the idea that they'd be so happy if they just moved to Hawaii or traveled to Europe, thinking everything's better there. The problem with travel is that your brain comes with you, and your brain is what causes feelings of anxiety."
He further emphasized the importance of addressing mental health directly: "Taking an SSRI, an anti-anxiety medication, has helped me more than having any amount of money."
Giving and Wealth Distribution
On giving money away, Andrew says: "Giving money away is joyful, right? It actually feels really good to shed it and help others. Why wouldn't you want to do that in your own lifetime?"
When asked if he's going to give all his money away before he dies, Andrew replied: "That's the goal. I want to die with certainly no assets to myself or close to."
On whether he plans to pass his wealth along to his kids, Andrew says:
"I think I'd give them proportionally a small amount. I don't know what that looks like. I think the goal would be to effectively give them a really awesome version of Social Security, where they always know that they're gonna have a house and medical care and all those basics, but ultimately they're on their own. But as of right now, I don't think I'm gonna give very much to my kids at all. I think it's all gonna go in the foundation."
OTHER KEY QUOTES
- "Going from making $6.50 an hour to suddenly having this design agency and making tens of thousands of dollars a month was incredible. Not having to worry about my rent, being able to go buy steak dinners, pick up the bar tab, everything else pales in comparison to that. That is the best money you'll ever make."
- "You think businesses need to make their employees happy, their customers happy, and their shareholders happy. And I think one of the mistakes a lot of people make is they don't really make the shareholder happy, and that's themselves. I mean, ultimately, you're the one doing all the work. And I've always felt that you should get paid well."
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