Most entrepreneurs dream about their big exit. They picture the moment they sell their company and ride off into the sunset. But here's what they don't tell you: exits aren't just about money. They're about legacy, people, and what happens next.

Over the past 30-plus years, I've been through five different exits. Each one taught me something different about business, leadership, and what really matters when you build something valuable. Today, I want to share these lessons with you so you can think beyond just the dollar signs when planning your own exit strategy.

Why Your First Exit Should Focus on Growth, Not Cash

My first real exit wasn't actually selling to a stranger. It was moving from side hustle to full-time business owner through a strategic merger.

I had been serving customers part-time while working another job. When the opportunity came to merge my small operation with a larger company, I jumped at it. Instead of taking cash, I took equity in the new venture.

"I merged my company where I had been serving on a part-time basis, a group of customers, and was able to move that into an equity position in a new company."

This decision changed everything. Suddenly, I could serve my customers full-time and build something much bigger than what I could create alone. We grew that merged company from $1 million to $32 million by doubling in size year after year.

The lesson here is simple: your first exit doesn't have to be your last. Sometimes the best move is to combine forces with someone who can help you grow faster than you ever could on your own.

Key Actions for Your First Exit:

• Consider equity over cash when you're young and can take more risk

• Look for partners who bring resources you lack

• Focus on growth potential rather than immediate payoff

• Keep serving your customers at a higher level

How Cash Flow Problems Force Smart Exit Decisions

By the time we hit $32 million in revenue, we faced a problem that sounds good but feels terrible: we were growing too fast for our cash flow.

"We just didn't have the cash to continue to fund a hundred percent year over year growth. And so we knew we were gonna have to take capital in some way, shape, or form."

This forced our second major exit decision. A firm from Palo Alto wanted to buy our internet service provider division, but during negotiations, they realized they actually wanted our main business.

Within one month, we sold both companies.

The beautiful part? I stayed on as a partner in the acquiring firm. This gave me front-row seats to 18 additional acquisitions as we built a national company. At 23 years old (the average age in our company), I was learning about mergers and acquisitions at a pace most entrepreneurs never experience.

What Fast Growth Really Costs:

• Your personal cash reserves get stretched thin

• You need outside capital to maintain momentum

• The right buyer can solve your cash problem and accelerate growth

• Sometimes selling is the smartest way to keep growing

The Power of Stock Options and Employee Wealth Creation

Here's where most entrepreneurs get it wrong. They think exits are just about making themselves rich. But the smartest exits create wealth for everyone involved.

When we built our national company, we created a stock option program with vesting schedules. This wasn't just nice to have - it became incredibly valuable as we continued growing.

"We also had the opportunity to build a stock option program, with a vesting schedule. Which later on became incredibly valuable for the employee community as we walked through this journey."

By the time our next buyer came along - a fast-growing company in Silicon Valley going through an IPO - we had over $350 million in stock options across our division.

But here's the critical part: I didn't just hand out stock options and walk away. I educated our team about diversification. I taught them how to maintain wealth outside the company while still participating in our growth.

Why Employee Wealth Matters:

• Happy employees work harder and stay longer

• Stock options align everyone's interests with company success

• Teaching diversification shows you care about their future

• Wealthy employees become loyal advocates for your leadership

What Public Company Life Teaches About Leadership

Our fourth exit brought us into the public company world, and this taught me lessons I couldn't learn anywhere else.

"I got inside exposure to the quarter by quarter nature of public companies. It was very interesting to go from, I'll say, an entrepreneur led and founder led organization to a managing partner in a national, but still privately held company to a publicly traded company."

Moving from founder-led to private equity to public company showed me three completely different approaches to business. The quarter-by-quarter pressure of public markets creates a unique intensity that shapes every decision.

But through all these transitions, one thing remained constant: the relationships I built with employees. They knew I cared about their outcomes, not just the company's performance.

Public Company Lessons:

• Quarter-by-quarter thinking changes how you operate

• Relationships matter more when everything else is changing

• Employee loyalty comes from genuine care, not just compensation

• Different ownership structures require different leadership styles

Why My Last Company Was Built Around Servant Leadership

My final exit was different from all the others because I had learned what really matters in business: people.

"This last company was the most employee centric company of all of the ones that I built. And I think it was because as I've gotten older, I've gotten a deeper appreciation that companies are fundamentally about people."

After 12 years of building this company, we merged with another firm to create more diverse offerings and accelerate our growth back to that 100% year-over-year pace I love so much.

But this time, I approached leadership completely differently. I became a servant leader. I looked at people as team members, not staff. I admitted when I didn't have answers and said, "We're going to figure it out together."

"I had developed a sense of, I'll say, confidence that I didn't need to have all the answers I could. Tell people, I'm not sure, but we're gonna figure it out together."

This happened during COVID, which made everything more stressful and complicated. But because we had built a culture of genuine care and mutual support, we not only survived but thrived.

Servant Leadership Principles:

• Admit when you don't know something

• Focus on team success over personal recognition

• Show up grateful for the opportunity to lead

• Care more about people than processes

The Emotional Reality of Letting Go

Here's what no one prepares you for: the hardest part of any exit isn't the negotiation or the paperwork. It's letting go of something you deeply love and care for.

"I had to pass it to someone else to continue to care for both the entity and the people in the entity."

Going from founder to employee to completely disconnected from your creation is an emotional journey that catches most entrepreneurs off guard. You put your heart and soul into building something, and then you have to trust someone else to take care of it.

Some transitions go well. Others don't. But that's part of the process when you build something bigger than yourself.

What Each Exit Taught Me About Success

Looking back at these five exits, here's what I learned about building valuable businesses:

Start with growth over cash. Your early exits should focus on building something bigger, not just cashing out.

Solve real problems. Whether it's cash flow issues or market expansion needs, the best exits solve genuine business problems for everyone involved.

Take care of your people. Employee wealth creation isn't just nice - it's smart business that creates loyalty and drives performance.

Stay flexible with structure. Different ownership models require different leadership approaches, but relationships always matter most.

Lead with humility. The most successful companies happen when leaders focus on serving their teams instead of building their own egos.

Your Next Steps for Planning Better Exits

If you're building a company right now, start thinking about these questions:

1. What legacy do you want to create beyond just financial returns?

2. How can you structure employee ownership to align everyone's interests?

3. What would make your company attractive to strategic buyers?

4. How can you build systems that work without you being involved in every decision?

5. What kind of leader do you want to be remembered as?

Remember, exits aren't endings. They're transitions that create new opportunities for everyone involved. The goal isn't just to build something valuable - it's to build something that creates value for everyone who helped make it possible.

Your next exit might be your first, or it might be your fifth. Either way, make it count for more than just the money. Make it count for the people who believed in your vision and helped turn it into reality.Title