I’m a Self-Made Millionaire: These 3 Money Mistakes Have Made Me a Smarter Investor
Written by
G. Brian Davis
Edited by
Kristen Mae
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Kris Dehnert likes to laugh that he’s “one of those lame guys who named his company after himself.” But these days, he’s laughing all the way to the bank.
His primary business — the eponymous Dehnert Media Group — helps small businesses scale with better marketing and sales. But he also occasionally partners with his clients when he sees a fun, promising niche business. For example, he joined as an owner and executive at Dugout Mugs, which has earned more than $52 million selling coffee and beer mugs made from baseball bats. Fun, right?
But the road to riches comes with plenty of twists, turns and tough lessons. Dehnert has made his share of mistakes along the way — and says those missteps have made him a smarter investor. He now warns others to watch out for these three common pitfalls.
1. Investing in Ideas Rather Than People
People come up with clever business ideas all the time. You’ve probably had a few yourself.
What’s infinitely harder than a great idea is great execution. And that requires a great leadership team.
“At the end of the day, people are everything,” explains Dehnert. “Sometimes the idea turns out to need some refining, but you can just tell the person behind it is a warrior who is going to figure it out.”
2. Making Long-Term Investments Based on Today’s Conditions
The military has a saying: Generals are always preparing for the last war — not the next one. Investors fall into the same trap.
“Too often investors put cash into an opportunity that is fixing a current problem versus fixing a problem that is on the horizon,” Dehnert says. “Wayne Gretzky had a great quote: ‘I skate to where the puck is going to be, not where it has been.’ That’s a relevant lens for investors.”
Dehnert adds that he only makes large investments in businesses that he can directly impact. But he draws a clear distinction between taking ownership stakes in private businesses you help operate — which blurs the line with active income — versus your broader portfolio of passive investments.
Jeremy Savory, founder of the citizenship and residency service Millionaire Migrant, expands on that point: “A big money mistake is failing to diversify beyond what made you money in the first place. For instance, many crypto millionaires held too long and got wiped out in downturns.”
3. Making Overly (or Morally) Complex Investments
Ultimately, Dehnert prefers investments that are simple to understand and aligned with his values.
“I only invest in things that I can easily explain to my children, and that they would be proud of me to be involved in,” he says.
In addition to the baseball bat mugs and his media businesses, Dehnert helps run Bigg Golf, which makes not just golf balls but fun accessories like golf ball bottle openers and golf-themed board games.
“Making money is great, but leaving a legacy to those who matter is priceless.”
Looking to build a legacy? Check out our Life to Legacy guide for expert advice and smart moves you can make today.
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