Devon Kennard, a former NFL linebacker, defied the odds that see most players broke within five years of retirement. While playing for the Giants, Lions, and Cardinals over eight seasons, Kennard built an impressive portfolio of over 50 rental properties and 50+ syndication investments. Now, he shares his insights on how high earners can deploy their income wisely to secure their financial future.
Kennard’s story is a testament to the power of disciplined investing and strategic planning. His approach to real estate investing, developed during his NFL career, offers valuable lessons for anyone looking to build wealth through property.
Building a Rental Portfolio Amidst a Demanding Career
Kennard’s journey began with the purchase of his first rental property as a rookie. Despite the demanding schedule of an NFL player, which often exceeded 80 hours a week during the season, he managed to build his portfolio through disciplined time management and strategic decision-making.
“You don’t find more time. You make better trade-offs with the time you have,” Kennard advises. He emphasizes the importance of focusing on one market, building a reliable team, and accepting that initial deals may not be perfect. “Five OK rentals beat one perfect rental that never gets bought,” he notes, highlighting the value of taking action over endless research.
Kennard’s strategy involved dedicating five to seven focused hours a week to his real estate endeavors. This disciplined approach allowed him to purchase one property a year, gradually building his portfolio without compromising his NFL career.
The Pitfalls of Lifestyle Inflation
One of the most common mistakes Kennard observes among high earners is the tendency to treat lifestyle inflation as a reward rather than a financial burden. “They treat lifestyle inflation as a reward instead of a tax,” he explains, noting that increased spending becomes a permanent baseline, trapping individuals in a cycle of higher expenses.
Kennard witnessed this pattern firsthand in NFL locker rooms, where players would upgrade their lifestyles with new cars and homes, only to find themselves financially vulnerable when their next contract didn’t materialize. “A $1,200 car payment is a $1,200 monthly hole,” he points out, contrasting this with the potential income-generating benefits of investing the same amount in real estate.
“Most high earners don’t have an income problem. They have an allocation problem,” Kennard asserts, emphasizing the importance of redirecting income towards investments that generate returns rather than merely maintaining a lifestyle.
The Rental Property vs. 401(k) Debate
When asked to choose between maxing out a 401(k) or purchasing one rental property a year, Kennard opts for the latter. “The 401(k) is fine for what it is,” he acknowledges, but highlights the unique advantages of rental properties, including the ability to see and manage the investment, add value, and benefit from tax deductions.
“A rental gives you all of that. Plus, something nobody talks about—when you buy a rental, you become a different person,” Kennard explains. The experience of evaluating deals, managing tenants, and understanding markets builds valuable skills that compound over time, setting investors on a path to long-term financial success.
Kennard’s approach underscores the importance of active investment strategies that not only generate returns but also enhance the investor’s financial acumen.
Evaluating Deals with the Four C’s
As Kennard transitioned into private money lending, he developed a framework for evaluating deals based on the Four C’s: Character, Capacity, Collateral, and Capital. This disciplined approach ensures that investments are made with careful consideration and minimizes risk.
“Character: Have they done this before? Have they paid back loans cleanly? Do they communicate when things go sideways?” Kennard asks, emphasizing the importance of a borrower’s track record and communication skills. He also stresses the need for borrowers to have the capacity to execute, adequate collateral, and sufficient capital to cover down payments, interest, and rehab costs.
Kennard’s commitment to his own investments is evident in his lending practices. “Would I put my own money in this deal? Because I do,” he states, highlighting the importance of skin in the game and personal accountability in investment decisions.
Shifting from Income to Asset Building
Kennard’s journey from NFL player to real estate investor illustrates a crucial mental shift: from earning income to building assets. “Your job is not your wealth strategy. Your job is the fuel,” he emphasizes, encouraging individuals to view their income as a means to build lasting wealth rather than merely sustaining a lifestyle.
This shift in perspective is particularly relevant for high earners who may be tempted to spend their income on lifestyle upgrades rather than investing it. Kennard’s advice to his 25-year-old self underscores the importance of disciplined investing and the long-term benefits of treating income as seed capital for building wealth.
“Luck isn’t a strategy. Discipline is. And discipline at 25 looks like boring at 45 and rich at 55,” Kennard concludes, offering a powerful reminder of the value of disciplined, long-term investing.
