Life after selling a startup for $200M

Thought I’d do a fun one this week. A fellow founder privately shared insights into his life after selling a company for an undisclosed amount (likely over $200 million).

He requested anonymity, so I’ll keep personal details out.

Here’s a peek behind the curtains for motivation. I end with my thoughts on a freedom number and what I’d do with the money.

“Enough to Fly First Class… But Not Buy a Jet”

In 2017, this founder sold his company. Within 3 years, the earnout was done and the financial freedom was real.

He didn’t share the exact amount but hinted it was “enough to fly first class forever,” though “not enough to buy a jet.” Based on clues, ChatGPT estimates it’s likely between $30 and $50 million. 🙂

Here are 8 Things Things that Changed

1. The Big Move to Texas

“I moved to Texas before the deal closed to avoid owing California taxes,” he said.

This saved him a significant amount, and Texas became a strategic hub for new opportunities.

His advice? “If you can optimize where you live, do it.”

2. Best Investment Ever: A Specialist Accountant

He hired a pro who specializes in tech founders. “He’s my highest ROI investment,” he noted.

The accountant even suggested Puerto Rico for additional tax savings, but he declined.

I’ve personally considered Puerto Rico, too. It’s beautiful and just a 40-minute flight from my home in the Virgin Islands where I grew up. But right now, the Silicon Valley network outweighs the tax benefits.

3. Leaning into Startup Investing

“I became an LP in seven VC funds,” he shared. “They were modest checks to GPs I’ve known for years because they invested in my prior companies.” He also gets separate deals from VCs and has invested in a dozen startups this way.

The lifecycle of a successful founder almost always ends in startup investing. It keeps them in the game, allows them to give back, and happens to be very lucrative.

4. Family First: “I Wanted to Give Back”

Helping family was one of his biggest priorities.

• Bought houses for his parents and an older sibling.

• Paid off student loans for other siblings.

• Set up a monthly stipend for his parents.

• Offered full college rides for nieces and nephews who get into top-100 schools.

5. Ultimate Convenience: No More Chores

“I have no chores,” he laughed. With a personal assistant, handyman, cleaner, lawn care, pet-sitting, and even a driver for his dog to get to pet-sitting, his daily life is chore-free.

His personal assistant helps him with everything from getting his car washed to hanging souvenirs.

“This is my second-favorite thing on this list,” he admitted.

Freedom from chores is something all physicians could do if we wanted given our hourly rates.

6. Chasing New Passions

With the freedom to pursue interests, he dove into hobbies he’d always wanted to try.

• Cycling Coach: “My coach shows up at 6:45 AM. No excuses.”

• $2M Plane: “I earned my commercial pilot’s license and bought a small plane. It’s pressurized and flies at 300MPH, but costs a fifth of what a jet costs to operate. This is exactly as awesome as I dreamed.”

7. Real Estate Reality Check

“I bought several rental properties and promptly regretted it.”

“They are the furthest thing from passive income, even with property managers.”

8. Back to Business – Building the Next Venture

“A week after my earnout ended, I started a new company,” he shared.

His reason? “I love the challenge. I’m still just as hungry to win.”

Most people think freedom means lounging on a hammock and are surprised when ultra-wealthy people keep grinding. But the truth is, they’re wealthy because they love the grind.

Freedom is simply doing what you want—which, for some, means working on what they love.

What Hasn’t Changed

Despite newfound wealth, some things stayed the same:

• The Hustle: “I still work 60-70 hours a week. I love it.”

• Simple Lifestyle: He still wears $20 blue shirts from Amazon, bought in bulk, and hasn’t splurged on luxury cars or vacation homes.

• Family Dynamics: “Nobody asks for handouts,” he said. The only exception was a short-term loan for a sibling, repaid with interest.

My Own Thoughts on a Freedom Number

There’s a real danger in chasing money—you’re never satisfied. If money is the only goal, those extra purchases won’t add lasting happiness. That’s why I admire how this founder prioritized spending on meaningful experiences.

For me, my freedom number is about what I truly want out of life.

I felt semi-retired, content, and fairly free before my latest startup. That freedom made me feel like I could dive in. I already had enough to live comfortably and splurge on my one luxury: travel.

But since then, my dreams have grown.

On a material level, I’d love to buy my parents an extra place within walking distance and to fund annual group vacations with friends and family. And yes, I occasionally dream of a small stake in an NBA team and sitting courtside.

But the real goal isn’t material. After experiencing how tough it is to build an impactful startup while balancing profitability, a big payday would give me the freedom to pursue high-impact projects without the need for profit.

I’d assemble a high-caliber team to tackle moonshots—projects aimed at expanding access to education, healthcare, housing, and essential resources in underserved areas.

Reply to tell me your freedom number, and what would you do with it.