Life After the League: How Athletes (and High Earners) Can Win at Wealth

I love meeting amazing people who make a difference — not only in their professions, but in how they think about freedom, money, and life.

Devon Kennard is one such example. A former NFL linebacker, Devon is now an author, investor, and advocate for financial education for professional athletes. His story is one of discipline, foresight, and smart investing – the same principles that guide lifestyle investing.

Our paths crossed through the Pro Athlete Community (PAC) — an organization dedicated to helping athletes become better stewards of their money. Thanks to Devon, I was able to spend time in Scottsdale with over 250 athletes learning, networking, and building financial confidence. To see a room full of competitors focused on their next chapter, rather than the next game, was inspiring.

In this post, Devon explains the costly mistakes athletes and high earners frequently make, how he built a hands-off investment portfolio that pays consistently, and how he turned setbacks into opportunities.

From NFL Star to Lifestyle Investor

Before we met, Devon was already a Lifestyle Investor.

Before he learned about lifestyle investing, he felt he lived the lifestyle-investor mindset. He just didn’t have the right community around him.

Devon already owned assets and invested in syndications as a real estate investor. However, he often found himself translating advice from generic finance books that didn’t fit his world. Having found “The Lifestyle Investor” book and podcast, he finally felt like he was speaking his language.

It was that discovery that marked a turning point. As a Lifestyle Investor, he had the option to own assets that generated cash flow, buy back his time, and invest intentionally.

Facing Reality: “You’re Being Replaced”

One of Devon’s most powerful observations was how the NFL exposes job insecurity like never before.

“When you’re playing pro sports, it’s in your face more than any other industry that you’re going to be replaced,” he says. “Don’t buy all the things that you want today and put yourself in a position where you can’t buy them down the line.”

It’s not uncommon for a team to bring in new players the next day after a bad game or injury. This is a stark reminder that earning and investing are limited.

As Devon points out, this lesson applies to everyone, not just athletes.

It’s the same for W-2 earners — you just don’t see the job as clearly, he explains. It doesn’t matter if it’s artificial intelligence (AI), automation, or younger, cheaper labor: you’re replaceable. As a result, you should create a portfolio you can walk away from on your terms, not theirs.

It’s a message that hits home. Financial independence isn’t just about wealth — it’s about freedom. Rather than being forced into decisions by circumstances, you can decide when and how to work.

The Harsh Reality of “Big Money”

There is a common misconception that professional athletes are financially secure. Devon quickly dispels that myth.

Suppose you make $15 million, he said. You might end up keeping only around $7 million after taxes, agent fees, and other costs.

That may sound like a lot, until you realize that many players spend $30,000 to $100,000 a month on their games. Without passive income, running out isn’t a question of if, it’s a matter of when.

Additionally, he emphasizes the deceptive nature of NFL contracts. What if you had to follow a contract 100%, but the other party didn’t? That’s basically the NFL. He says a ‘three-year, $15 million’ contract might only guarantee $10 million if you’re injured or underperforming.

It’s a lesson that applies far beyond sports: never count on income that isn’t guaranteed.

Fast Money vs. Slow Money: Knowing Where You Are

Devon uses a framework he calls “fast money vs. slow money.”

In most cases, fast money investments generate cash flow within a year. Investing in slow money tends to produce delayed returns, such as in development projects or venture capital.

Devon says he’s in the fast-money stage right now. His goal is to replace his NFL income and build a consistent cash flow to sustain his lifestyle.

When a professional is considering a career change or nearing retirement, fast-money investments offer flexibility and stability. On the other hand, early-career earners might focus more on tax-advantaged investments.

Clarity is the key: find out where you are in your journey and make the appropriate investments.

The Importance of Due Diligence With Money

As with many investors, Devon had to learn some lessons the hard way. An example of FOMO he shares was about a deal he jumped into out of fear of missing out.

He recalls being on a panel with a guy who made a lot of money. Despite this, he jumped right in without vetting first.

In the end, the deal was unable to get off the ground because of rising interest rates and poor debt structuring. He learned a valuable lesson from it. When someone’s scaling too fast—doubling assets under management — quickly, that’s a red flag. He believes they are probably overleveraged.

Now, he seeks out teams with a consistent track record, long-term partners, and fixed-rate debt. It’s not in Devon’s interest to invest in property managers or contractors who keep changing. It’s all about execution.

This kind of insight can only be gained through experience — or by learning from others’ mistakes. Oftentimes, I say, the “stupid tax” is the most expensive education.

Don’t Outsource Your Financial Education

Some many athletes and professionals entrust their money management to “experts” without understanding how they make money.

There are many misalignments in the financial services industry. Even if you don’t make money, advisors make money.

As Devon points out, financial education can’t be outsourced. Help is okay, but you need a solid foundation. But it’s helpful to know what a good deal looks like.

That’s why at PAC, every athlete receives the Vetting Deals Course and Passive Income Roadmap to help them evaluate investments and avoid common pitfalls.

Living Good Forever, Not Just for the Moment

During his rookie season, Devon had a memorable experience. Unlike teammates who drove Ferraris or Bentleys to practice, he drove his old 2005 Kia Sorento.

However, the moment that stuck with him was when he noticed quarterback Eli Manning driving a modest Toyota Sequoia — one of the highest-paid players on the team.

Devon says that was something special. Quiet wealth. Even though Eli knew he had it, he didn’t have to show it off.

That moment shaped Devon’s philosophy: live well forever, not for the moment.

As a result, he now teaches athletes (and anyone who will listen) the importance of delayed gratification — enjoying life without filling it with excess vices. If you enjoy traveling, that’s great, he says. Spend there. However, you don’t have to have a car, jewelry, or parties as well. Decide what’s most important and cut everything else.

Money Lessons That Go Beyond the Game

As Devon’s story demonstrates, smart investing is the key to achieving freedom, security, and purpose. Still, it also serves as a roadmap for any investor seeking to build these same foundations.

In every field, the Lifestyle Investor mindset applies: own assets, generate cash flow, protect your downside, and create a life you enjoy.

For Devon, living well is not just about living for now; it’s about living for good forever.

Every investor, entrepreneur, and professional should take that message to heart.

Key Takeaways

• Don’t rely on a paycheck. There is always an expiration date, even for the biggest or most profitable of jobs. To mitigate risk, diversify your investments, and do not put all your resources into one opportunity.
• Focus on cash flow (“fast money”) before long-term bets (“slow money”). Using this approach, you can generate a steady stream of income to cover expenses and reinvest in future opportunities. Once your cash flow is stable, you can shift your focus to long-term investments that yield higher returns.
• Vet deals thoroughly and beware of over-leveraged operators. Before agreeing to any deal, verify the operator’s financial health and track record. Overleveraged operators may have difficulty meeting obligations, increasing the risk of losses. To make informed investment decisions, review financial statements and understand the operator’s debt-to-equity ratio.
• Never outsource your financial literacy — understand your investments and opportunities. Financial literacy allows you to avoid costly mistakes, make informed decisions, and build wealth strategically. It’s possible to create a secure and sustainable future if you take control of your financial education.
• Spend intentionally. Living within your means will allow you to choose what you value most in life.

Featured Image Credit: Joe Calomeni; Pexels: Thank you!