DP+ Founder, Owner and CEO Mark Petrosky has been leading the full-service marketing and service agency for 24 years. He spent about a decade buying his partners as he navigated the company toward a sale process. It was time to sell, he decided, after an event required a business valuation.

"And as we started to look at it, I’m coming off three giant years, which from a timing perspective obviously makes a lot of sense. And with my age — I’m 59 — it started getting to the point where I had to get my chips off the table, so to speak, and start getting my retirement funded and take a look at succession."

While he had a qualified plan as source of part of his retirement funds, the proceeds from the sale of the company made up a larger portion.

"I would tell my 30-year-old self now, you were crazy to rely so much on the assets of the business selling, especially in the marketing advertising business," Petrosky says. "There's a lot of risk and there's a lot of volatility. I probably rolled the dice way too long on taking money and buying out partners and investing in the company. I would have probably been better off balancing it. But the bet paid off. So, to future owners I would probably do a better job of balancing that act."

The process leading into a sale took close to two years. He says it started by sitting with financial advisors and trying to figure out what he needed get out of the sale to generate the income he wanted to live off of. At the same time, he was looking to his business evaluation folks to see if the company was ready to go to market.

"We started the process very conservatively in terms of probably close to 60 percent of what my team that was going to take me to market thought it was going to look like," he says. "And we did all the tax connotations with that and so I got comfort from the financial planners what my number needed to be."

Tax, he says, is such a big component of estate planning. His primary focus, though, was on ensuring his own retirement. Passing along generational wealth was secondary since planning had already been done around his adult children and they're both working.

Petrosky says he had done some basic estate planning prior to the decision to go to market but as soon as he and his advisers started to get a framework of what go-to-market could look like and the amount of money that it looked like it was going to generate, a whole new level of sophistication had to be looked at.

"I completely switched to a whole new firm and that became very important," he says. "It's so complex. I highly recommend anybody thinking about it, you have to do it. And then we started looking at generation skipping and gift trust and all the complex issues that could be done prior to the sale that you had to get in place with enough lead time before the sale for it to pass muster. So, fortunately I did that and we did all kinds of things to put in more sophisticated estate planning eight months before the projected sale. And if I knew the numbers earlier, it probably would have been better if I did it two years before the projected sale."

Petrosky, along with Cendrowski Corporate Advisors' John Alfonsi and Pitcairn's Andy Busser spoke at the Chicago Smart Business Dealmakers Conference about how a seller's approach to the pre-planning and execution — including taking the impact of taxes into consideration — may be the difference between a deal's success and failure. Hit play to catch the full panel discussion.