What athletes made great investments?

I don’t know who invented donuts, but I really do love them. It’s impossible to be sad and eat a donut.

We’ve all seen the stories: athletes making tens of millions during their career only to retire broke a few years later. The combination of short career spans, lifestyle creep, and poor financial advice has wrecked more bank accounts than any opponent ever did.

But there’s another side to the story. Some athletes have made incredible investments outside their sport, setting themselves up for generational wealth. This week, let’s look at some of the smartest money moves athletes have made off the field, the court, and the ice.

Note: Michael Jordan isn’t on this list. Yes, he’s one of the greatest athlete-investors of all time. But his Nike deal was deeply tied to his basketball stardom, and we’re focusing here on investments outside direct sports endorsements.

Patrick Dovigi – Green for Life (GFL) Environmental

Patrick Dovigi is a former minor league hockey goalie who was drafted by the Edmonton Oilers in 1997. He only played professional hockey from 1995 - 1999 before starting an entrepreneurial career. In 2004, he was working with an investment firm and was put in charge of overseeing the clean up of a waste transfer station that the firm had a controlling stake in. This planted the seed for him starting GFL, a waste management company (who picks up my trash!) with over 15,000 employees. For the record, I have zero evidence to support that claim. I am just connecting some dots.

Wow Scale: A+

One man’s trash is another man’s treasure? Patrick is the reason for this saying with a net worth of $1 billion thanks to GFL. His NHL career was just a rest stop on his path to wealth. I am starting off strong because unlike everyone else on this list, Patrick built GFL from the ground up.

LeBron James – Blaze Pizza

LeBron may have a weird tendency to lie for seemingly no reason, but he also has made some smart investment decisions. In 2012, he invested in Blaze Pizza turning a ~$1 million stake into a business now worth hundreds of millions. In 2015, he doubled down on it by leaving his McDonalds marketing contract to start advertising for Blaze Pizza. 

Wow Scale: B+

From everything I can read, it sounds like LeBron did “take a chance” on Blaze Pizza by turning down millions from McDonalds. He says he wanted to take equity and go all-in on Blaze instead of getting a paycheck from McDonalds. 

Serena Williams – Serena Ventures

Serena launched Serena Ventures in 2014 during a second peak in her career ranked #1 in the world. The firm has invested in over 60 startups including fintech, health, and e-commerce companies with 5 successful exits. The firm actively seeks women and underrepresented founders. Today, her portfolio is valued in the hundreds of millions.

Wow Scale: A-

Serena gets a high rating because she started this firm during a record breaking 186 weeks as the World #1 Tennis Player from 2013 to 2016. She said she wanted to work on her plan B during plan A. That takes some serious drive.

Shaquille O’Neal – Everything (Seriously)

Shaq might have the most fun portfolio in sports. He invested $250,000 in Google in 1999, owned dozens of Auntie Anne’s, Papa John’s, and Five Guys franchises, and has stakes in everything from car washes to nightclubs. His business mantra? “If I don't like your product, I can't take your money and sell something I don't like to the people.”

Wow Scale: B

Look, Shaq has one of the most impressive portfolios of any athlete… His Google investment is top notch. His portfolio is diverse and believes in all his products, which is the big lesson here. However, his involvement and control is hard to gauge. 

Roger Staubach – Real Estate Empire

The former Dallas Cowboys QB with two super bowl victories turned his NFL salary into a commercial real estate empire. He founded The Staubach Company, which became one of the most successful real estate firms in the U.S. The company was in commercial and residential development in Dallas. They also represented commercial clients looking for office space which was apparently more lucrative during periods of excessive vacant office space. He eventually sold it to Jones Lang LaSalle for $613 million.

Wow Scale: B+

Staubach is the OG athlete-investor. Not only did he have a record breaking NFL career, he then grew a real estate empire for 30 years. 

Takeaway

The common thread here? These athletes didn’t just rely on their paychecks or their brand endorsements. They put money into boring, scalable, income-producing assets (real estate, waste management, pizza) or into early-stage companies with huge upside (Google, Blaze Pizza, Serena Ventures).

So what’s the takeaway for us retail investors? Don’t chase the meme stock hype with any substantial amount of money. Invest in low cost, indexed ETFs each and every month. Be boring today to be wealthy later. 

Debrief on Deck

Next week, we debrief September. Time is fake. How is it going so fast??

As always, please reach out to us with any questions or comments you have. You can reply directly to this email or find us on Instagram.

Until then, stay the course.

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