This year my articles have centered around how a horse race is like selling a business. We began at the starting gate, describing the first steps in selling a business and how deal flow works. As we proceeded through the months, we talked about what happens when the offer to buy the business is accepted, how the deal is consummated, and the moment when the keys are handed to the new owner.

We’re at the end of the race. The business is sold. Now what happens? For owners who take the important step of planning this phase before selling their business, the “now what” question has been addressed in advance.

Many selling owners use the period after the sale of the business for relaxation, hobbies or a part-time job. Some sellers intend to buy, build or invest in another business. Others are ready to seek new adventures.

Of the “seek new adventures” category, I’d like to talk about one owner with whom I worked recently. He and I worked on his business for two years before its sale.

Pat Crann was interested in selling his business himself. As founder of Shout Out Loud Prints in Columbus, OH, USA, Pat was emotionally ready to sell his apparel screen printing operation. He had a small staff and the proper equipment, but he did not have anyone qualified to succeed him at the management level. We talked about finding a strategic buyer who was interested in being an owner-operator.

At first glance, I felt Pat would be leaving money on the table if he sold the business as it sat. After completing the valuation and going through our analysis, Pat understood the potential.

Although he wanted to sell the business himself, Pat knew there were key parts of the process he didn’t understand yet. He needed someone in his corner who had the knowledge and experience to guide him. He turned to us.

From our discussions, I sensed Pat had the right personality and intelligence to successfully build and sell his business. The question was, did he have the heart and patience to do so?

Pat expressed to me that, even though he was only in his mid-30s, after 18 years in the business he was exhausted and overwhelmed. He was leaning toward exiting right away. He knew there was room for the business to grow, but he thought he might leave that part to the new owner. He did, however, want to make sure his employees and customers would be taken care of. He worried that if the business was not strong enough to survive under a new owner, he would be letting down the people who relied on him. He wanted his employees to be well trained and empowered so they could support the new owner through the transition.

It typically takes 18 to 24 months to grow and sell, sometimes longer. As we developed Pat’s roadmap, we customized it so he could move faster when he was able, and slower when the demands of the business and personal issues needed attention. The approach gave him flexibility but also structure, which was important for an entrepreneur who has so much to do within a small business.

With the roadmap, Pat could see light at the end of the tunnel. He could see a future free from the worry and responsibility that was weighing him down. With a fresh outlook and the support of our experienced coaching team, Pat systematically executed our recommendations. He worked on team building, sales strategies and operational efficiencies. He put his financial house in order in preparation for the sale. Pat flourished in our coaching program, adopting the LCG values of trust, transparency (truth), and timelines.
Not every entrepreneur can manage the sale of his or her business in this manner. It’s a full-time job to sell a business on top of running the day-to-day operations. Pat had to trust his team and learn to step back.

When it was time to look at prospective buyers, we knew we had to focus on more than a transaction. Yes, the buyer had to be financially able to acquire and run the business. However, when founders put their heart and soul into a business, they need to be reassured that the person taking over has what it takes to carry on the legacy. We identified some promising buyers, had those heart-to-heart discussions with them, and located an entrepreneur who had the will and commitment to lead Shout Out Loud Prints.

The sale of Pat’s screen printing business came together during the early months of the pandemic. We feared the sale would be sidetracked as financial institutions struggled with workloads and working virtually. Pat’s entire team of sell-side advisors persevered. Pat kept his buyer engaged and motivated to close. Although it was challenging to bring all the players to the table, Pat showed maturity, confidence, wisdom and patience. His buyer and his advisors hung in there and worked creatively to complete the sale.

Once the sale was complete, Pat’s new life plan went into effect. He was ready to hit the road with his wife, Rachael. Since then, Pat has sent me photos from their adventures in the remotest corners of North America. The planning was worth it. Pat and Rachael’s smiles tell the story of freedom, optimism and renewed vigor.

Over my years in business, I have helped many owners do the deep planning required to turn the page successfully, but working with Pat was one of the most satisfying for myself and my team.

As we wrap up this year’s horse racing theme, I think about how Pat won the race and chose to walk away from the racetrack to start a new life. His vision, supported by a solid plan for growth and transition, allowed Pat to achieve the future he always dreamed of.


Envisioning your life post-sale
As you think about selling your business and what life might look like after the sale, here are some questions to ponder. We recommend you write down your answers and refer back to them periodically. You will find that things change as you approach financial and emotional readiness. 

1. Are you interested in taking time off after the sale?
2. Do you wish to relocate?
3. Does your spouse know about your thoughts?
4. Are you on good terms with your spouse and family?
5. How does your family situation affect your decisions about the sale and life after the sale?
6. Will you want to continue to have some role or financial part in the business once it’s sold? Are you inclined to retain your business in some way so you can preserve or continue your family name and legacy?
7. If not, would you want to be retained as a consultant to assist the new owner?
8. Are you addicted to being busy? Would your family say you area workaholic?
9. Do you have a personal identity that’s separate from your role as the owner? Do you have a social support system, including friends, your church or social groups? Do you have hobbies and interests outside work?
10. Do you know others in your circles who have successfully sold their businesses? Have you talked to them in detail about their experiences?
11. Do you ever feel guilty, fearful or angry about how your life has gone? Have you ever talked to a family counselor, therapist or other professional to help you visualize your future without the business?
12. Are you healthy? Do you have the energy it takes to sell the business yourself or would you need more help?
13. Do you regularly consult with professional advisors about finances, tax implications and wealth management to get proper advice?
14. Do you know what your ideal life would look like if you sold the business? Have you envisioned it down to the details? Are there pieces that need to be laid in place now? Do you need to change or evolve personally to make this happen?
15. Do you have a trustworthy and experienced advisor or coach who can keep a watchful eye and warn you of pitfalls?
16. If you are emotionally and financially ready to sell your business, is there anything standing in your way?