Most NFL players are broke within five years of retirement. The statistic gets repeated so often it’s become background noise, but the numbers are real, and the trajectory is brutal: big contracts, bigger lifestyles, a career that ends in your 20s or 30s, and a financial cliff that arrives faster than anyone planned for.
Devon Kennard isn’t one of those statistics. He played eight seasons in the NFL as a linebacker for the Giants, Lions, and Cardinals. He also bought his first rental as a rookie, kept buying throughout his career, and walked away from the game with 50+ properties, 50+ syndication investments, and a private lending business he runs with his wife Camille out of Phoenix.
He’s now the author of It All Adds Up and one of the most thoughtful voices in real estate on how high earners should actually deploy their income while they’re earning it. I asked him six questions about building a portfolio while working 80-hour weeks, the most expensive mistake high earners make, and what he’d tell his 25-year-old self.
His answers are the most useful financial advice you’ll read this year if you have a W2 and a paycheck you don’t know what to do with.
1. How to Buy Your First Five Rentals While Your Job Eats Your Life
Q: How do you buy your first five rentals when your job already eats 60 hours a week?
“You don’t find more time. You make better trade-offs with the time you have.
When I was playing in the NFL, my in-season schedule was closer to 80 hours. I made three moves that changed everything.
One: I picked one market and went deep. Most people burn six months researching 15 markets and buy nothing. Pick one. Learn it cold.
Two: I built a small team before I needed it. Property manager, agent, lender. When a deal showed up, I made a decision in two evenings, not two weeks.
Three: I accepted that my first few deals would be OK, not amazing. Five OK rentals beat one perfect rental that never gets bought.
With five to seven focused hours a week, you can buy one property a year. That’s how you get to five. Not by quitting your job. By being disciplined with the time you have.”
The line that should be on every aspiring investor’s whiteboard: Five OK rentals beat one perfect rental that never gets bought.
The single biggest reason high earners with money to deploy never deploy it is the trap Devon describes in move No. 1. Six months of market research turns into a year. The year turns into “I’m waiting for rates to come down.” Two years later, they own the same zero properties and have read 40 books about real estate.
Five to seven focused hours a week is part of the answer worth sitting with. That’s not a hobby, commitment, or a side hustle. That’s an hour a day, Monday through Friday, with weekends off. Anyone reading this can find an hour a day if they’re honest about how they spend their evenings.
Your move
Pick your market this week, not next quarter. Then book three calls in the next 10 days: a property manager, an investor-friendly agent, and a local lender. The team comes before the deal, not after it.
2. The Lifestyle Inflation Tax Most High Earners Pay Forever
Q: What’s the most expensive mistake you see high earners make with their money before they discover real estate?
“They treat lifestyle inflation as a reward instead of a tax.
Every raise becomes a bigger house, nicer car, and better vacations. It feels earned. But lifestyle costs don’t go away—they become the new baseline. You raised your floor permanently to enjoy something temporarily.
I saw it constantly in NFL locker rooms. First real contract: a new car payment within 60 days and a lifestyle that required the next contract to maintain. Then the next contract didn’t come.
The expensive mistake isn’t spending money. It’s spending it in ways that don’t generate more money. A $1,200 car payment is a $1,200 monthly hole. That same $1,200 in the right property generates income, builds equity, and creates tax deductions. Same dollar. Completely different trajectory.
Most high earners don’t have an income problem. They have an allocation problem.”
“Most high earners don’t have an income problem. They have an allocation problem.”
Every high-income reader of this newsletter should screenshot that line and put it on their refrigerator. It explains why the doctor making $400K and the engineer making $180K can both end up in the exact same place at age 55: comfortable but not free, with a paid-off house and a 401(k) and nothing else.
Devon’s locker room example is the version of this story most BiggerPockets readers haven’t seen. The pattern is identical to what plays out in tech offices, sales floors, and law firms. The only thing different is the size of the numbers.
The mechanism is the same: a raise arrives, the lifestyle expands to absorb it, the new lifestyle requires the income that bought it, and now you’re trapped at a higher level instead of free at any level.
Your move
Look at your last three years of income and then your net worth today. If the second number didn’t grow proportionally with the first, you’re paying the lifestyle inflation tax and don’t know it. The fix is redirecting the next raise into something that pays you back—not just earning more money.
3. The 401(K) vs. Rental Property Question, Settled
Q: If you had to pick one, would you max out your 401k or buy one rental property a year? Why?
“One rental property a year.
The 401(k) is fine for what it is. Tax-deferred, employer match, hands-off. But you can’t see what you own, can’t add value to it, can’t refinance it, can’t write off depreciation, and can’t pass it down with a stepped-up basis.
A rental gives you all of that. Plus, something nobody talks about—when you buy a rental, you become a different person. You learn to evaluate deals, manage tenants, and read markets. That knowledge compounds in ways 401(k) contributions never do.
After 10 years, one path leaves you with 10 properties and real skill at allocating capital. The other leaves you with a bigger account balance and the same skills you had a decade ago.
I’d pick the properties every time.”
The part of Devon’s answer that’s easy to miss is the second-to-last paragraph. Most of the debate around 401(k) versus real estate focuses on returns and tax treatment. Devon’s saying the most valuable output of buying rentals is that you become a person who knows how to allocate capital.
That skill is the actual moat. A person with 10 properties and 10 years of decision-making experience can pivot into any kind of deal flow. One with a $400K 401(k) balance can max out next year’s contribution. Those are not the same financial trajectory, even when the balance sheets look similar on paper.
The standard financial advisor objection to Devon’s answer is risk. Real estate isn’t passive. Tenants are messy. Properties break.
All of that’s true. It’s a feature, not a bug. The friction is what builds the operator.
Your move
If you’re maxing out your 401(k) and not buying rentals, redirect the difference between your current contribution and the employer match minimum into a rental property fund for the next 18 months. Most people will be shocked at how fast that hits a down payment.
4. Devon’s Four C’s for Evaluating Any Deal
Q: You’ve moved into private money lending on top of owning rentals. What does a deal have to look like for you to actually write the check?
“The Four C’s.
- Character: Have they done this before? Have they paid back loans cleanly? Do they communicate when things go sideways? I’d rather lend to a B-credit borrower with great character than an A-credit borrower with a history of disappearing.
- Capacity: Can they actually execute? Money doesn’t fix execution problems.
- Collateral: What’s the property worth today? Not what they say, not what an old appraisal says—what my wife Camille, a Compass agent in Phoenix, tells me. Max loan amount: 70% of after-repair value.
- Capital: Do they have enough cash for the down payment, monthly interest, and to front rehab costs themselves? If they’re stretched going in, they’re broke coming out.
Then one more question: Would I put my own money in this deal? Because I do. My personal capital is the largest single source of funding in every loan we make. If I wouldn’t risk my own dollars, I won’t risk anyone else’s.
That’s why we’ve never had a principal loss.”
The Four C’s is the most concrete, shareable framework Devon has put on the record, and it’s the kind of thing that becomes a reference document for any investor who wants to evaluate deal flow with discipline.
If you’re the one trying to raise private money, Devon just gave you the exact rubric your lender will score you against: Character, Capacity, Collateral, Capital. Build a track record on each one, in that order, before you ask anyone to write a check.
The “would I put my own money in this deal” filter at the end is the part most lenders skip. It’s also the part that explains why Devon’s loans don’t go bad. Skin in the game changes how you underwrite every time.
Your move
Whether you’re lending, borrowing, or evaluating a real estate partnership, run it through the Four C’s. If any are weak, the deal is weak. Don’t paper over a missing C with a higher interest rate.
5. From Earning Income to Building Assets
Q: You went from locker room to landlord. What’s the mental shift most W2 earners never make?
“From earning income to building assets.
In the NFL, your job is to perform. You get paid for what you do in this game, this season. Your identity is wrapped up in what you do. Most W2 earners are the same—they’re a teacher, an engineer, a sales rep. Their identity is their work, and their income comes from doing it.
The shift is realizing that what you do is just the vehicle for what you build. Football wasn’t my goal—it was the funding mechanism. By the time I retired, the machine I’d built mattered more than the football did.
Most W2 earners never make that shift. They identify with their work, spend most of what they earn, save the rest in a 401(k) they don’t understand, and hope it works out at 65. Their entire wealth strategy is ‘keep doing my job.’
Your job is not your wealth strategy. Your job is the fuel. Those are two different things. Confusing them is why most high earners hit middle age still feeling stuck.”
“Your job is not your wealth strategy. Your job is the fuel.”
That sentence is doing more work than almost anything published about personal finance this decade. It reframes the entire question of what a job is for. Not “the thing you do that defines you” or “the source of your identity.” It’s the funding mechanism for the actual machine.
Devon had a uniquely visible version of this problem because the NFL forces the question on every player by their early 30s. The game ends, the income stops, and the identity collapses. The asset base either exists or it doesn’t.
Most W2 earners never get that forcing function. The job just keeps going. The decade passes. The next decade passes. And the question of what they were actually building underneath all that earning never gets asked until it’s too late to answer.
Your move
Write down what you do for work, and then write what you’re building underneath it. If the second list is shorter than the first, you have your 2026 project.
6. What Devon Would Tell His 25-Year-Old Self
Q: Most pro athletes are broke five years after retirement. What did you do differently, and what would you tell a 25-year-old version of yourself?
“I bought my first rental as a rookie. By the time I retired, I owned over 50 properties and had invested in 50+ syndications. My wealth didn’t need the next contract.
Most athletes go broke because their identity, lifestyle, and income are all wrapped up in playing. When the playing stops, all three collapse at once.
What I’d tell my 25-year-old self: The money you’re making right now is not your money. It’s seed capital. You’re not a millionaire—you’re a kid who got a once-in-a-lifetime opportunity to build something that outlasts your career. Don’t spend it like income. Deploy it like investment capital.
The worst financial decisions you’ll make are the ones that feel like rewards. The lifestyle upgrade that proves you’ve made it. Those feel like victories in the moment and look like mistakes in the rearview.
Luck isn’t a strategy. Discipline is. And discipline at 25 looks like boring at 45 and rich at 55.”
This is the part that lands hardest if you read it slowly: “The money you’re making right now is not your money. It’s seed capital.”
Apply that filter to every dollar that arrives in your bank account this year, and a lot of decisions get easier. The new car and bigger house become harder to justify, and the investment property becomes easier to justify. Seed capital wants to be deployed, not spent.
Devon’s closing line is the headline of the whole interview if you had to pick one: “Luck isn’t a strategy. Discipline is. And discipline at 25 looks like boring at 45 and rich at 55.”
You can’t market that line any better than it markets itself.
The One-Line Takeaway From All Six Answers
The W2 earners who get rich aren’t earning more than everyone else. They’re allocating differently.
Devon’s career is the proof of concept. The same NFL paycheck that made other players broke at 35 made him free at 32. The difference wasn’t talent or contract size. It was treating the income as fuel for the machine instead of as the machine itself.
That’s the framework. The question is whether you’ll deploy it before your next raise hits your account or after.
Devon Kennard is a former NFL linebacker, founder of 42 Solutions, and author of It All Adds Up. He invests in real estate and runs a private lending business in Phoenix with his wife, Camille.
Follow Devon: devonkennard.com
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