I sold my business. What’s next?

Business owners pour time, energy and effort into building their companies and helping them grow. It makes sense that after the “I sold my business!” moment, people experience complex feelings, from pride and accomplishment to anxiety and sadness.

We spoke with Lynne King Smith, Jay Steinfeld and David Lyon, leaders who have sold thriving companies. They shared their thoughts on what came next, how they stay fulfilled and engaged and why mentoring adds meaning to their post-sale lives.

Understanding flexibility and resilience

Lynne King Smith and her husband built the technology firm TicketForce, which provided ticketing software for event venues. TicketForce had 30 full-time employees and supported $110 million in ticket sales by the time they sold.

In the days after selling TicketForce, King Smith says, she was exhausted, excited and “still pretty focused.” She had a management contract with the buyer, so she was concentrating on the transition.

Then, the COVID-19 pandemic hit and shut down the events industry, so her exit became much different than expected.

King Smith decided to dive into another venture: running for mayor in her town of Gilbert, Arizona. She earned an impressive number of votes, but another candidate ultimately won. Then, days later, she received notice that “essentially [her] whole family was laid off” when TicketForce’s buyer decided to end her management contract early and lay off more staff.

After a brief period of deciding what to do next, King Smith and her husband took their AirStream on a six-week trip, visiting national parks in the West, one of the only travel options during COVID.

King Smith says, “I remember riding along at one point saying to my husband, ‘Wow, we worked for 17 years, sold our company all to go camping in Utah??’” But the trip provided many miles to think, rest and talk about their future.

A few months later, King Smith put her focus on mentoring CEOs and joined Vistage Chair Academy.

Mentoring others is part of King Smith’s purpose. “I love what I’m doing, and I look at being a Vistage Chair as being a community builder, because if I’m able to impact business leaders,” she says. “Then ultimately, I can create a positive ripple effect that reaches many people, including their employees and families. This, in turn, helps to strengthen communities as a whole.”

King Smith’s advice for business owners who intend to sell is to “have a clear idea of what your vision for your life is outside your business.” Instead of being defined by your company, she says, determine your core values and purpose. Then, you can ensure your next moves align with that mission.

Knowing your true purpose

Jay Steinfeld founded Blinds.com, the world’s first and leading online retailer of blinds. Starting the company by himself in his garage, Steinfeld eventually grew Blinds.com to 500 employees. In 2014, Steinfeld sold the business to Home Depot.

Steinfeld didn’t experience the anxiety and depression that some business owners do after selling. “I felt accomplished, gratified, proud,” he shares. He believes that the reason some struggle is that they don’t know their true purpose or have a plan to continue fulfilling that purpose. “They’re like the dog that catches up to the car, and now they don’t know what to do with it.”

Before leaving Blinds.com, Steinfeld made sure he knew what his next goals were — and that he was already achieving some of them. He had also ensured that his team could thrive following his departure with his identified successor. Taking these steps helped Steinfeld feel ready to transition.
Now, Steinfeld finds fulfillment in staying involved with his old team. They sometimes ask him to come to meetings, and he recently joined them for their 10-year “orange-iversary,” the anniversary of the sale to Home Depot.

Steinfeld advises business owners preparing for a sale to start thinking about how to make a difference, whether for future or current entrepreneurs, their community or a cause they are passionate about.

As a mentor, Steinfeld says, “I’m advising people, and I’m giving back by serving on multiple boards and teaching in the business school at Rice.” By staying “in the game,” he stays mentally fit and sharp.

Most importantly, Steinfeld is now spending as much time as possible with his family and eight grandchildren. He’s looking forward to bringing his three-year-old grandson to swimming lessons on Tuesdays. “It’s going to be awesome,” he says. “That’s going to be my favorite day.”

Realizing who you are

David Lyon has sold two businesses. The first was a digital marketing company that helped small and medium-sized businesses transition from traditional to digital media. He started with three employees. By the time of the sale seven years later, they had close to 300.

Lyon’s second business was a venture-backed software-as-a-service firm that helped enterprises with organizational culture and employee engagement. That company had 20 employees.

After the first sale, Lyon felt exhilarated. He and his team were at the right place at the right time, and they did all the right things. He had thought that the most meaningful part would be the money, but instead, he says, “What really stuck with me was what we had accomplished as a team.”

His second sale, on the other hand, was “a hard-fought win.” He felt a lot more apathy and fatigue after closing.

Looking back, Lyon says that more preparation would have gone a long way in ensuring a smooth sale process and transition.

In addition to preparing for the sale, Lyon says preparing yourself for what you’ll do next is vital. Like many business owners, his identity was wrapped up in his company. “I didn’t ask myself the question that I now know to ask people, which is: Who are you apart from the business?”

He adds, “I invested so much of my time, energy and attention on the business that when both of these transactions were done, I didn’t have the same structure that the business gave me.” Finding that structure is critical to filling the void a sale can leave behind.

After a significant transition, people have an opportunity to understand what’s most important in life. For Lyon, this meant prioritizing his family and finding ways to help the next generation of business leaders, finding the latter as a Vistage Chair.

Now a CEO coach and mentor, Lyon says, “I’m giving back as an entrepreneur, sharing some of the hard-fought lessons that I learned.”

Living life after the sale

After selling their businesses, King Smith, Steinfeld and Lyon had very different experiences, but how they approached life follows a similar path. They have each focused on staying true to their vision and purpose and understanding their true selves. They spend time with their families. Ultimately, they found that mentoring allows them to give back to their communities while finding fulfillment and joy.

Related Resources

10 critical factors to evaluate before selling your small business

Planning your business exit: Asset protection for the sale [Webinar on demand]

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