Recently, I had the honor of moderating a roundtable discussion with a group of experienced founders who have each been through the life-changing process of selling their businesses. Many assume that selling a company is mostly a financial transaction, but this conversation revealed a much richer reality. Founders grapple not only with negotiations but, perhaps even more, with the emotional journey of letting go of something they’ve built over years or even decades.

Below are some of the most profound takeaways from the discussion.

1. The Emotional Rollercoaster: “It’s not just a company—it’s part of you.”

One of the recurring themes was the emotional toll of selling a business. As one founder put it, “Selling isn’t just handing over the keys; you’re letting go of a piece of yourself. It feels like losing part of your identity.”

Another shared his own experience of selling his company after 15 years. “You think you’re prepared,” he said, “but once the ink is dry, you realize you’re not just walking away from a business; you’re walking away from the community, the daily problems, and the wins that kept you going. That’s tough.”

Another founder compared the experience to raising a child. “You nurture it, watch it grow, and then, at some point, you have to let it go into the world, hoping you’ve done enough to ensure it thrives without you.”

2. Planning for Life After the Sale: “I didn’t think I’d feel so lost.”

The emotional void after selling a business can catch founders by surprise. One founder shared a cautionary tale about not planning for what came next: “I thought selling the company would be the happiest day of my life. But within a few months, I found myself feeling aimless, almost like I was grieving.”

Another added, “It’s essential to have something lined up after the sale. Whether it’s another project, time with family, or even just travel—anything to fill that gap. Because if you don’t, it can leave you feeling lost.”

One founder turned the post-sale uncertainty into an opportunity for growth. “I threw myself into advising other entrepreneurs and started speaking at events. It gave me a new sense of purpose, and honestly, it kept me from falling into that post-sale slump.”

3. Choosing the Right Buyer: “It’s not just about the money.”

The founders agreed that it is crucial to find a buyer who aligns with your vision. One recounted his experience of turning down a higher offer because it didn’t feel right. “We had an offer that was above what we expected,” he said, “but the buyer’s culture didn’t match ours. I couldn’t shake the feeling that they would dismantle everything we built, and I didn’t want my team to go through that.”

This was echoed by several founders, and I reflected on my experience in coaching several founders through this process.

“You’re not just selling a company—you’re handing over your legacy. It’s important that the buyer not only sees the financial value but also respects the culture, people, and mission you’ve worked so hard to build.”

One advisor described a founder who regretted selling to a buyer who prioritized profits over people. “A friend of mine sold his company, thinking the new owners would maintain the culture. Instead, they stripped it down, cut staff, and turned it into something unrecognizable. It left him with a sense of regret that the money couldn’t erase.”

4. The Art of Letting Go: “I wanted to hold on to the reins forever.”

One of the hardest parts of the process for many founders is learning to trust the new leadership team. Townsend summed it up well: “You can’t keep your hands on the wheel forever. There comes a point where you have to trust someone else to drive.”

Letting go can be particularly hard for founders who have been involved in every detail of the business. One confessed, “I stayed on as an advisor after the sale, but I found myself micromanaging the new team. At some point, I realized I was holding them back. They needed the space to make decisions without me constantly looking over their shoulder.”

The consensus was that transitioning out of leadership requires founders to step back and allow the new owners to take control. “It’s about setting boundaries,” said one. “I told myself that I would give advice if they asked, but I wouldn’t interfere unless it was absolutely necessary.”

5. Learning from Mistakes: “Surround yourself with people who’ve done this before.”

Throughout the discussion, founders reflected on the missteps they made during their exits, offering invaluable advice for others contemplating the sale process. One founder admitted to rushing into a sale without fully understanding the tax implications. “I was so eager to close the deal that I didn’t take the time to consult the right advisors. It cost me millions in taxes.”

Greg Head emphasized the importance of building a trusted team early on. “Surround yourself with people who’ve done this before—lawyers, financial advisors, even other founders who have sold their companies. Their experience will help you avoid costly mistakes.”

Several founders agreed that rushing the process is one of the biggest mistakes you can make. “It’s easy to get caught up in the excitement and pressure of selling,” Townsend noted, “but you have to take your time. Don’t let anyone rush you into a decision you’re not 100% comfortable with.”

Going Deeper

Selling a company is about far more than dollars and cents. It’s a deeply emotional and complex experience that requires careful planning, both financially and emotionally. Whether you’re choosing the right buyer, planning for life after the sale, or learning to let go, it’s essential to surround yourself with people who can guide you through the process.

These founders’ stories serve as a powerful reminder: selling your company is the end of one chapter, but it’s also the beginning of a new one. The more intentional you are about the process, the better you’ll be prepared to navigate the journey ahead.

I’ll be posting clips from my event, “The Other Side of the Exit: Is There Happiness Beyond the Deal?” over the next few weeks. Keep an eye out for them on LinkedIn and other platforms.

And if you would like a copy of the full recording, or to be considered for the next event, be sure to DM me or make a comment below.

 

 

Exiting a business is a significant event for any entrepreneur, but what surprises many is not the money, but the personal transformation that often accompanies it. My recent conversation with Michael Showalter provided an eye-opening perspective on the lessons learned from navigating an exit. Here are a few key takeaways from his exit:

1. Letting Go Can Bring You More

One of the most powerful lessons from Michael’s story is the counterintuitive reality that letting go can open doors. Michael shared how, once he stopped striving for titles and accolades, opportunities seemed to come his way naturally. In 2015, he aggressively pursued a CEO role and didn’t get it. His frustration led to a lot of soul-searching, and the realization that his actual enjoyment came from the work that he was doing and not the title he had while doing it.

That led him to seek a role that offered him more fulfillment. And when he truly let go of needing more recognition, he was offered the CEO position at his next company. It was a vote of confidence from the outgoing CEO, the founder of the company. He knew that Michael would be the best steward going forward, because he was focused on the company and not his own needs.

2. Success Without Stress

Michael’s story also illustrates that success doesn’t have to be fraught with stress. The company’s exit wasn’t a result of cutthroat tactics but a series of thoughtful, strategic decisions. They kept investing in technology when their competitors didn’t, leading to a four-year advantage. The team did the hard work without attaching undue stress to the outcome, resulting in a smoother exit and a more successful outcome.

3. The “Why” Behind the Exit

Michael spent a lot of time reflecting on the “why” behind his desire for an exit. Many founders pursue an exit thinking it will fill some personal void—whether it’s proving themselves, achieving financial security, or gaining respect. Yet, Michael emphasized that any feelings of fulfillment you’re seeking through an exit are already available to you now. The satisfaction isn’t in the exit itself but in running a business you love and doing meaningful work each day.

For Michael, the exit emerged as simply the best thing to do for the business, not as a personal or financial goal for him. In fact, he pointed out that there were several people at the firm who got more financially than he did.

4. The Fallacy of External Happiness

One of Michael’s biggest realizations came from his first attempt to become CEO. When he failed, it hit him that the role itself was not going to make him happy, and that nothing outside of him—a role, an amount of money, or any other kind of achievement—could do that. He was making himself a victim of his circumstances. He could choose a different internal experience no matter the outer situation.

Many of us believe that once we hit certain financial milestones, we’ll feel fulfilled. Yet, Michael realized that lasting happiness isn’t tied to a financial number or professional status—it’s an internal state. You don’t need an exit to feel successful; but feeling successful in and of itself can lead to a better result.

5. A Change in Perspective

Ultimately, the biggest shift Michael experienced preceded the financial reward of the exit. He discovered that his self-worth wasn’t tied to professional achievement. This allowed him to lead more effectively, as he no longer needed external validation. He could focus on the needs of the business, even when it was difficult personally.

It’s a reminder to all of us that our external circumstances—be it an exit or a promotion—don’t define us. It’s how we view ourselves and our circumstances that really matters.

Final Thoughts

An exit is more than a financial or business transaction. It’s a personal transformation. Whether you’re building towards an exit or simply growing your business, consider this: Are you chasing an external event for fulfillment? Or are you already fulfilled in the work you’re doing now?

I’ll be posting clips from my interview with Michael. Be sure to check them out on LinkedIn and YouTube.

What insights resonate with you as you think about your own business journey? Let me know in the comments. And if you’d like to be included in my event for founders who are within three years of an exit, send me a message or comment “Invite” below.

#founder #entrepreneur #leadership #exit #transformation #ceo

Three of my clients have had exits in the last year.

All of them got checks in the range of $20-50 million. Combined enterprise value is north of $400 million.

But they had very different experiences. Before, during, and after.

That started me asking some questions—

What makes for a good exit? What would each of these folks have done differently? How is life post-exit better or worse than what they envisioned? What will they do differently NEXT TIME—and they all are working toward another exit.

The more I talked to my network of founders and advisors, the more I found that founders had no one to talk to about this.

So I found some top notch people to put in a virtual room to offer their perspectives to founders within three years of an exit.

Founders like you.

A Stellar Panel of Experts on All Things Exit

Townsend Wardlaw first had his own less than glamorous exit and has since coached and advised over three dozen founders to the point of exit and beyond.

Greg Head likes to say that he had “1-1/2 exits” in the SaaS space and today helps bootstrapped SasS companies build and sell in a way that brings purpose and freedom without buying into the VC game that works for so few founders.

Michael McAllister had his own life-changing exit in early 2024 and has seen that the entrepreneurial journey is about the founder facing both their strengths and their fears. He continues that journey today as he builds a renewed and healthier sense of purpose.

Anastasia Koroleva(invited) had her own 9-figure exit and then built and sold three more companies. Her own struggles with meaning and purpose on the other side of the exit led her to start a community and a podcast, “Exit Paradox” that focused on the lessons, personal and otherwise, that founders learn during and after exit.

Virtual Invitation-Only Event on September 17

On September 17 at noon Eastern time, you can have access to all of us—to hear about the experiences we have had, the lessons we’ve learned, and the questions we still have.

And you will have full access both to ask us any questions you have, and to connect with a group of founders just like you.

If you want to be live in the room, and you are within 3 years of an anticipated exit, please respond “INVITE” or send me a DM

I’ll ask you a couple of questions about what you want to create and then send you the invite.

Have a great week!

#founder #founders #exit #freedom