Estate planning, says Wholesale Supplies Plus Founder and Retired CEO Deb May, is complicated. There are a lot of options to consider — not just with the planning itself, but the attorneys who help with the planning all approach the process differently.  

For May, among the priorities for her and her family was to minimize taxes, not wanting to pay more than required, and then to protect their nest egg for future generations. They’re straight-forward goals, but achieving them was complicated.

“Money was always taboo for us growing up,” May says. “My parents didn't talk about it, my aunts and uncles, grandparents — so I didn't really know where to turn.”

She says she ultimately leaned on her accountant, interviewed a number of other service professionals to find the right fit. And ultimately she found the right fit in a legacy trust for her daughters.

“It's really easy to look at the money you get from selling your company and think, ‘I'm going to do this, I'm going to do that,” May says. “But we really have put an emphasis on respecting the money, nurturing it, growing it and being a shepherd of it for future generations.”

However, she says she wishes she would have done her estate planning before selling the business. That might have enabled them to take advantage of options that weren’t available post-sale. But the lessons she learned from her liquidity event she’s been able to pass along to Chris Copley, a friend and CEO of Capital Anesthesia Solutions, who’s still working in his business.

Copley says he and his family hadn't contemplated any estate plans until recently because he had his head down and focused on building the company, which grew extremely fast. When he and his family looked up, they realized it had become something much bigger than what they anticipated, and they started to be approached by companies about a potential sale.

“That got me to thinking, maybe I need to start looking at this in a more prospective way as opposed to getting to a point where, like Debbie had mentioned, looking back retrospectively saying maybe I should have done something different,” Copley says.

He reached out to May, he says, to get her opinion about how she approached estate planning, knowing that at some point a sale is going to be an option. He wanted to know how he could start planning ahead to set himself up to make the most of the benefits a liquidity event could bring for his family.

“A lot of it revolved around, do I need all these things right now? Not necessarily,” he says. “We have plenty of things that I have to think about and give consideration to that would have to be included even at this point in life that are very important to think about. I mean, our assets,  college for our children and how we can benefit them and generations to come.”

May and Copley, along with UBS Managing Director William Murphy, spoke at the recent Cleveland Smart Business Dealmakers Conference about their family businesses, estate planning pre- and post-liquidity event, as well as how to pick the right estate planning adviser. Hit play on the video above to catch the full discussion.