The Time Jiu Jitsu Saved a $400M Real Estate Deal

A few years into training Jiu Jitsu, I put my practice on hold and moved to the East Coast to pursue a career in real estate. Moving to New York was a massive leap outside my comfort zone, but it changed my life. I landed a job at a real estate startup on Park Avenue, chasing my dream of becoming a real-life Bud Fox. Everything was clicking—I thrived at work, loved the city’s energy, and even met my wife on my morning commute. Looking back, Jiu Jitsu undoubtedly played a role in giving me the confidence to take those steps, but I didn’t yet realize how directly it would impact my professional life.
A Hard Lesson in Management
After a few years at the startup, I left over a disagreement in management philosophy. To me, the issue was black and white, but my bosses saw grey. Rather than compromise my values, I walked away. The company skyrocketed to the top of the real estate world—until, in my opinion, the very issue that made me leave ultimately brought them down.
I returned to Chicago and partnered with a longtime friend to start our own real estate firm. By the end of our first year, we had closed our first deal. From there, we hit the gas. Within a few years, we were managing a massive pool of client assets and aggressively searching for new opportunities. That search led us overseas, where a portfolio of properties was up for sale by a large institutional seller.
The deal wasn’t a perfect fit as-is, but we had a plan to put the properties under contract and renegotiate the leases directly with the tenant during our due diligence period. We would put the signed lease extensions in escrow before closing and they would take effect as soon as we funded. It was an ambitious plan, but we had a strong relationship with the tenant and had already worked out an agreement.
The Art of Problem-Solving
Around this time, I had returned to Jiu Jitsu training and was working toward my blue belt at Serafin Jiu Jitsu. My game revolved around playing from the bottom—flexibility and a decent triangle choke made rubber guard a natural fit. Plus, I was lazy. I figured I wasn’t a good enough wrestler to guarantee top position, so I’d better learn how to attack from my back.
What I didn’t realize was that playing guard properly is exhausting. Good guard passers move side to side, pin your hips, and make you suffer. That’s when I discovered one of the simplest yet most effective tools in Jiu Jitsu: the stiff arm.
A fully extended, locked-out arm can be a powerful weapon. Whether it’s a running back palming the helmet of a charging linebacker or a Jiu Jitsu player stiff-arming an opponent to maintain distance, the principle is the same—create space, control the tempo, and get back to an offensive cycle. The best guard passers don’t fight the stiff arm head-on. They stay patient, adjust angles, and find a way through.
The $400M Stiff Arm
A few months into the deal, everything was lining up. We had a purchase agreement with the seller, and the signed leases were in escrow. The last step was for the tenant to officially waive their Right of First Refusal (ROFR)—a clause that allowed them to match our deal and buy the properties themselves.
We weren’t worried. We had met with them in person, shaken hands, and received verbal confirmation they wouldn’t exercise it.
Then, I got the call.
“They exercised the ROFR!”
I was on the train when my partner called, his voice filled with rage. A $400M deal—one that would take our firm to the next level—had just evaporated.
“I’m going to call them and tear them a new one,” he seethed.
At that moment, the image of being stiff armed flashed in my mind. We weren’t out of the game—a significant obstacle had just been put in our way and we needed to find a way around. If we lost our temper and fought it head-on, we’d lose everything. But if we stayed calm and adjusted the angle, we could still win.
“Hold on,” I said. “If we go nuclear, we’re done. Can we sweeten the deal? More properties? Better terms? Anything?”
That brief pause snapped my partner out of his fury. He immediately shifted gears. “I’ll call you back,” he said.
Twenty-four hours later, the deal was back on. We agreed to buy a few additional properties the tenant owned and adjusted their lease terms in a way that made sense for both parties. Win-win. We closed later that month and continued our own ascent to the top of the real estate world.
Jiu Jitsu in Business and Life
I’ve heard countless people talk about the benefits of Jiu Jitsu outside the gym. “It’s like 4D chess.” “It’s extreme problem-solving with dire physical consequences.” And while I don’t disagree, the simplest way to describe what I’ve learned from my practice is:
When you hit an obstacle, you either quit or you find a way through.
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