Intentional Growth

#181: Selling a Company Twice: Once to a Strategic Buyer & Again 10 Years Later to a PE Firm

Intentional Growth
#181: Selling a Company Twice: Once to a Strategic Buyer & Again 10 Years Later to a PE Firm

80% of deals that go to market don't close. Gayle McCann defies all odds by selling their firm two times and to completely different buyers... and neither of the exits were planned. 

Out of the blue offers happen all the time and the chances it works out as planned are very slim. This episode is a story about two out of the blue offers and how all the stars align more than once.

 Gayle shares what she and her husband, Pat, learned through each of the exits and what the process was like. In addition to that, Gayle and I talk about the different kinds of people it takes to run, sell, and buy back a business, and the different strategies Gayle and Pat used when they were running their business together.

 Tune into Gayle's journey on what it's like selling the same company to two different types of buyers. The more stories you hear of how people have grown and exited, the more you'll be able to intentionally grow your company with the end in mind.

What you will learn:

  • Gayle’s history and background
  • How Gayle and her husband started and sold their business the first time to a strategic buyer
  • What their attorney included in their sale agreement that allowed them to buy back the company four years after they sold it
  • How Gayle's professional advisors structured the deals
  • Stories on what it was like merging three agencies that were bought by the Private Equity fir
  • What it's like working with three other companies and CEOs post-closing
  • How Gayle and Pat were able to maintain a health marriage while staying business partners
  • The differences between a Strategic Buyer and a Private Equity Firm exit
  • Gayle’s experience, transitioning out of the business and handing off her role and clients


“The more you learn about the different things available, the more you’re going to figure out what you want.” - Ryan

“We did something very innovative, that no one else had ever done; we actually hired an underwriter from an insurance company because we wanted to focus on having a set-up of support people that were the top in their industry, that were going to give our clients A+, level 10 care.” - 

“You don’t need--to live the life you want to, doesn’t take as much as people think.” - Ryan


Learning from other people’s journeys can help you refine what you want. This will help you be able to approach the out-of-the-blue offers and your eventual growth plan with the knowledge to be able to create the options you want.

Links and Resources:

Gayle McCann, LinkedIn 

ARKONA Boot Camp

Reach out to me if you have questions about the boot camp! 

You can also reach out to me via email at or on my LinkedIn

About Gayle:

Gayle an experienced executive and entrepreneur with a demonstrated history of working in the employee benefits industry. In 1984 Gayle co-founded an employee benefits brokerage, Johnson McCann, that grew rapidly until 2012 when they merged with 3 other brokerages making them the largest independent insurance brokerage in Minnesota. Their division continues to specialize in employee benefits insurance. Gayle’s skill was chief strategist for our clients in managing their benefits package while managing our employees and the business. Gayle’s client niche markets were working with medical groups and hospitals, non-profits, public and private education institutions, and specialized businesses.

Brought to you by Ryan Tansom of Intentional Growth