By Nana Muazin 
The statistics regarding professional athletes and their post-retirement finances are as sobering as they are predictable. Within five years of leaving the National Football League (NFL), an alarming percentage of players find themselves in dire financial straits. This phenomenon has become so pervasive that it is often treated as a tragic, inevitable backdrop to professional sports. Players command massive contracts, adopt extravagant lifestyles, and hit a financial wall the moment their playing careers—typically ending in their late 20s or early 30s—conclude.
However, Devon Kennard, a veteran linebacker who spent eight seasons with the New York Giants, Detroit Lions, and Arizona Cardinals, stands as a notable exception. Kennard didn’t just survive the transition from professional athlete to civilian life; he thrived. By treating his NFL salary not as a lifetime annuity, but as "seed capital," Kennard retired with a portfolio of over 50 rental properties, 50-plus syndication investments, and a thriving private lending business run alongside his wife, Camille.
His new book, It All Adds Up, serves as a blueprint for high earners—whether they are professional athletes, doctors, or software engineers—on how to deploy income effectively while it is still flowing.
The Chronology of a Portfolio
Kennard’s journey into real estate did not begin after his retirement; it began while he was still a rookie. Recognizing the volatility of a career in professional football, Kennard made a conscious decision to start buying rental properties immediately.
Throughout his eight-year career, he balanced the grueling 80-hour work weeks typical of an NFL athlete with the demands of building a real estate business. His strategy was simple but disciplined:
- The Early Years: Purchasing his first rental property as a rookie, he established a habit of reinvesting his income rather than inflating his lifestyle.
- The Mid-Career Build: As his contracts grew, Kennard scaled his operations, focusing on market deep-dives and team building.
- The Transition: By the time he officially hung up his cleats, his "machine"—his real estate and lending portfolio—was already generating significant cash flow, allowing him to shift his identity from "athlete" to "investor" without the psychological or financial collapse many of his peers experienced.
Breaking Down the "80-Hour Work Week" Myth
One of the most common excuses for those failing to build wealth is a lack of time. Kennard argues that the issue isn’t time; it’s trade-offs.
Mastering the Market
Kennard advises against the "analysis paralysis" that traps many would-be investors. "Most people burn six months researching 15 markets and buy nothing," he notes. His methodology involves picking one market and learning it "cold." By narrowing the focus, an investor can make high-quality decisions in hours rather than weeks.
Building a Team Before the Need Arises
Kennard emphasizes the importance of building a "boots-on-the-ground" team—comprising a property manager, an agent, and a lender—before the actual deal is found. By having this infrastructure in place, he was able to act with speed and precision, even while preparing for game day.
The Power of "OK" Deals
Perhaps his most provocative piece of advice is that "five OK rentals beat one perfect rental that never gets bought." Perfectionism is the enemy of progress. Kennard suggests that by aiming for consistency rather than the "perfect" home run, investors can realistically acquire one property a year, eventually building a significant portfolio through steady, disciplined action.
Lifestyle Inflation: The Hidden Tax
Kennard posits that most high earners do not have an income problem; they have an "allocation problem." In the NFL locker room, he witnessed the cycle of lifestyle inflation firsthand. A new contract would arrive, followed almost immediately by a luxury car payment and an expensive lifestyle that necessitated the next contract just to maintain the status quo.
"Lifestyle costs don’t go away—they become the new baseline," Kennard explains. He defines the most expensive mistake high earners make as treating a raise as a reward rather than an opportunity to invest. When an individual spends $1,200 on a car payment, they have created a monthly "hole" in their budget. That same $1,200, if directed into a cash-flowing asset, would generate income, build equity, and offer tax deductions.
The 401(k) vs. Real Estate Debate
When asked whether a high earner should prioritize a 401(k) or rental properties, Kennard is definitive: "One rental property a year."
While he acknowledges the utility of tax-deferred, hands-off retirement accounts, he argues that they lack the transformative power of real estate. "You can’t see what you own, you can’t add value to it, you can’t refinance it, and you can’t write off depreciation in a 401(k)," he says.
Moreover, Kennard highlights the human element: the investor. Buying real estate forces an individual to learn how to evaluate deals, manage tenants, and understand market cycles. This knowledge compounds over time, creating a "moat" of experience that no standard retirement account can offer. By the end of a decade, the person who invested in 10 properties has evolved into a skilled capital allocator, while the person who relied solely on a 401(k) has simply accumulated a balance.
The Four C’s of Deal Evaluation
For those entering the world of private lending or partnership, Kennard provides a rigorous framework known as the "Four C’s." These are the non-negotiables for any deal he considers:
- Character: Is the borrower reliable and honest?
- Capacity: Do they have the ability to execute the project?
- Collateral: Is the underlying asset secure?
- Capital: Is there sufficient cash to see the project through to completion?
Beyond these metrics, Kennard applies a "Skin in the Game" test. He asks himself, "Would I put my own money in this deal?" Because he often does—using his personal capital as the primary funding source for his loans—this filter has ensured that his business has never suffered a principal loss.
Implications for the Future
The core of Kennard’s philosophy is a fundamental shift in identity. Many professionals define themselves by their work—the doctor, the engineer, the athlete. Kennard argues that your job is not your wealth strategy; it is merely the "fuel."
The psychological danger for high earners, particularly those in high-intensity careers, is confusing the source of their income with their identity. When the job ends, the identity collapses. By viewing one’s career as a funding mechanism for a broader "machine" of assets, the individual remains stable regardless of their employment status.
A Call to Action
For anyone reading this, the path forward is clear. Kennard challenges readers to audit their last three years of income and compare it to their current net worth. If the net worth has not grown proportionally to the income, the individual is likely paying a "lifestyle inflation tax."
The solution is a return to disciplined, boring, and intentional investing. As Kennard poignantly concludes, "Discipline at 25 looks like boring at 45 and rich at 55."
The "financial cliff" that claims so many former high performers is not an inevitability—it is a choice. By prioritizing asset accumulation over lifestyle upgrades, treating income as seed capital, and focusing on the long-term compounding of both wealth and skill, high earners can ensure that their financial future is defined not by their last paycheck, but by the assets they built while they were still earning it.
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