From Exit to Investor: How to Build and Protect Wealth After the Big Win

You’ve spent years, maybe decades, building a business from the ground up. You led a team, made tough calls, and poured everything into making it a success. Then, one day, the exit deal closes. The wire hits. You’ve officially made it.

And then… silence.

The emails stop. The meetings disappear from your calendar. For the first time in a long time, you’re not building—you’re holding capital.

That’s exactly where my friend Dr. Tony Jacob found himself not long ago. As a doctor and CEO of a thriving multi-location optometry practice, Tony spent years scaling his business before selling it. After the sale, he transitioned to full-time investing through RORHRO Ventures, a family office focused on real estate, private equity, and alternative investments.

In this post, Tony shares what life looks like after the exit — the highs, the challenges, and the lessons every entrepreneur should know about building, managing, and preserving wealth once the business chapter closes.

Life After the Exit

As soon as Tony sold, he stopped receiving emails. It was great for two or three months. Then reality set in. “What am I going to do with myself?”, he asked himself.

It’s a common theme among entrepreneurs after selling their businesses. When you move from full throttle to wide-open space, you can feel disoriented.

For Tony, he had built something remarkable. He had over a dozen thriving locations across Texas. A strong team. A reputation that attracted private equity firms’ attention. So, it was perfect timing for him to speak with an investment banker about exploring growth options.

By 2021, he’d completed the sale before market conditions changed and valuations began to fall. He says the timing was fortunate. From doctor to CEO to chairman and finally to exit, it was like being on a rocket ship.

However, the real challenge wasn’t selling, but what followed.

The “Now What?” Phase

After selling, Tony took a full year off. No new deals. No rush. He used this time to decompress and learn.

He admits that he was inexperienced in investing. Although he knew how to run a business, this was different. Once again, he had to become a student.

The transition from wealth creation to wealth preservation is among the biggest mindset shifts successful entrepreneurs face. When it comes to investing, the skills you use to build a business (speed, confidence, intuition) actually hurt you.

That’s why I always tell new members of The Lifestyle Investor Mastermind the same thing:
Don’t rush into deals. Rush into education.

The goal isn’t to deploy capital quickly, but to make wise, strategic decisions aligned with your goals and investment criteria.

Building a Family Office (Your Way)

After his exit, Tony focused on structuring his family office — an idea he had not even heard of.

Essentially, a family office provides the infrastructure to manage assets, investments, and your financial strategy. You can create one just for your family (a single-family office), join a multi-family office with dozens or hundreds of others, or even share costs with a few friends.

Tony learned that there is no one-size-fits-all model. According to him, you can decide which part of your portfolio you manage yourself and which is managed by others. To find what is right for you, you need to consider your lifestyle.

After a big exit, he advises anyone sitting on cash to do the following:

It’s OK to wait a year or two before investing. Get to know the landscape. Take the time to understand what you’re signing up for. And, size your bets carefully.

Patience pays off in the end. Markets shift. Opportunities evolve. In addition, Tony noted that even simple treasury and cash instruments deserve your attention before you branch out into more complex ones.

The Shift from Creation to Preservation

Most of your wealth is tied to your business as an entrepreneur. As a result of that concentration, both growth and risk are created.

With an exit, the focus switches to diversification and preservation.

According to Tony, entrepreneurs focus on what they do best. However, diversification and preservation call for a completely different approach.

As a result, he started exploring various asset classes, including:

• Venture capital. Watching startups grow by planting small seeds.
• Private equity. Scaling or repositioning established businesses through acquisition or investment.
• Private credit. Offering consistent returns on structured lending.
• Real estate. Plays both actively and passively (LP or GP).
• Oil and gas. Another form of “real estate” that caught his attention.
• Public markets. Especially for liquidity and stability, it’s still a part of the mix.

Before investing in a bucket, the smartest investors take time to understand the level of risk, return, and involvement involved.

Avoid This Rookie Investing Mistake

As Tony began investing post-exit, he fell into a trap I see every day.

It’s called “spray and pray.”

After taking a chunk of money, he just started making deals. It all sounded great. However, he didn’t know how to do diligence properly, so he assumed it would be good if many other people were involved.

It wasn’t just him. Every new investor feels a fear of missing out. There’s a lot of deal flow in your inbox, friends are investing, and it’s tempting to believe that more is better.

That’s not the case.

Tony quickly learned that lesson. He found managing K-1s and tracking all those deals to be a headache. He now takes his time. It’s okay if he misses a deal. More will follow. More importantly, he adheres to the number one investing rule from Warren Buffett: don’t lose money.

However, the goal isn’t to avoid every mistake — it’s to make smaller, smarter ones that you can learn from. Over time, your winners will outweigh your losers.

Why Masterminds Matter

Getting involved in peer groups and masterminds with investors was one of Tony’s biggest game changers.

Tony says he wishes he had known about these groups ten years ago. There is, however, a challenge in finding capital allocators you can trust. Once you do, everything changes.

That’s something I emphasize constantly. To grow their businesses, entrepreneurs invest heavily in masterminds, but few join wealth-building groups.

And yet, that’s where the biggest growth happens.

In groups like Lifestyle Investor, TIGER 21, or Strategic Coach, you’re surrounded by people who’ve been there — people playing the wealth game at a high level. You learn how to approach deals differently, structure them smarter, and manage capital more strategically as a result.

Additionally, you start asking better questions:

• What kind of impact do I want to make?
• How should wealth be structured for future generations?
• Beyond money, what does happiness look like?

In Tony’s opinion, wealth continues to grow, but what truly matters is family, health, friendship, and fulfillment.

The Evolution of an Investor

Today, Tony consults with a network of trusted peers and mentors to gain insight and accountability from his own “board of directors.”.

He’s still learning and evolving. However, he does it intentionally, surrounded by smart people who give him challenges and inspire him.

And that’s what lifestyle investing is all about.

The key isn’t just to make money; it’s to build freedom, take control of your time, and surround yourself with the right people.

True wealth isn’t measured by how much you earn or how much you keep.
Ultimately, it’s measured by your life, your relationships, and your legacy.

Final Thought

Whether you’re planning an exit or already have one under your belt, wealth preservation is an entirely different ballgame. But if you have patience, education, and the right network, you can win in the long run.

Key Takeaways

• Pause your exit. Before redeploying capital, you need time to recalibrate.
• Educate before you invest. It’s important to make informed, not impulsive, decisions to achieve the best returns.
• Avoid the “spray and pray” trap. Don’t choose quantity over quality — trust, diligence, and alignment are more important than deal flow.
• Build your family office intentionally. You don’t need to have a massive strategy — just one based on your goals.
• Join wealth-focused peer groups. Put yourself in the company of people who are better at the game than you are.
• Redefine success. Having wealth is not the goal; it’s a tool.

Featured Image Credit: Pixabay; Pexels: Thank you!