As a business owner, selling your company can feel like jumping out of a plane at 12,000 feet— exhilarating, risky, and full of uncertainty. Brett Rose, a seasoned skydiver and tech entrepreneur, learned this the hard way during a jump that nearly cost him his life. His story offers valuable lessons for entrepreneurs preparing to sell their business, highlighting the importance of preparation, timing, and contingency planning to ensure a safe landing.

The Jump: A Business on the Brink

Brett Rose had made over 1,000 jumps as a skydiver, often telling nervous first-timers, “Skydiving is safer than driving your car to work on I-95.” But on a cloudless Saturday in May, high above Palm Beach County, Brett’s confidence was put to the ultimate test. At 3,500 feet, his main parachute malfunctioned, leaving him in a freefall with the ground approaching faster than he could think.

For business owners, the decision to sell can feel just as disorienting. You’ve built your company through years of hard work, much like Brett’s dedication to skydiving while growing his construction company. But when the time comes to exit, unexpected challenges—like a parachute that won’t deploy—can threaten everything. The key is to prepare for the jump long before you step out of the plane.

Lesson 1: Prepare Your Business for a Smooth Descent

Brett’s story underscores the importance of preparation. Just as he checked his gear before every jump, you must ensure your business is ready for sale. Clean up your financials, document processes, and reduce dependency on yourself as the owner. Buyers, like Brett’s reserve parachute, are your safety net—but they’ll only invest in a business that’s well-organized and low-risk. Start preparing 12–24 months in advance to maximize your company’s value and avoid last-minute scrambles.

The Freefall: Timing Your Exit

As Brett plummeted toward the earth, he felt the familiar rush of freefall turn into panic. His main chute had failed, and at 1,000 feet, he knew he had to act fast. He deployed his reserve parachute just in time, landing safely on shaky legs that didn’t settle until long after.

Timing is just as critical when selling your business. Brett waited until the last possible moment to pull his reserve chute, a risky move that nearly cost him his life. Similarly, waiting too long to sell—or selling during a downturn—can jeopardize your company’s value. Brett’s business, a construction company worth $5 million, was a success because he knew when to push forward. But he also knew he couldn’t hold on forever, especially with a young family to consider.

Lesson 2: Sell at the Right Moment

Monitor market conditions and your company’s performance to identify the optimal time to sell. A strong economy or high demand in your industry can drive up your valuation, much like a clear day makes for a safer jump. Highlight recent growth or untapped potential to attract buyers willing to pay a premium. Don’t wait for a crisis to force your hand—plan your exit when your business is soaring, not spiraling.

The Aftermath: Protecting Your Legacy

After his near-fatal jump, Brett didn’t tell his wife, Orit, about the malfunction. He was 33, with two young kids and a third on the way, and he couldn’t bear the thought of worrying her. He also kept the incident from his employees, knowing that news of his risk-taking could spook the team and hurt his company’s value. Instead, he quietly visited friends Jenna and Kyshia, reflecting on what mattered most: his family and his legacy.

Selling a business isn’t just about the financial payout—it’s about protecting what you’ve built. Brett knew that if he died, his company’s value would plummet, leaving his family vulnerable. He also knew that selling to the wrong buyer could erase his legacy, much like a bad jump could erase his story.

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