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I have seen many owners benefit from multiple bites of the apple.

What does this mean? Well, an owner begins a sale process, but doesn’t sell 100% of the business. He or she stays in for some percent of the equity and benefits from value growth in the next few years. In some cases, the owner stays in again after the second sale and benefits again in the value growth resulting in the third sale.

I know of one owner who did this four times. How does this happen? Well, let’s address the key considerations that could lead to this wonderful set of events.

The Owner/Leadership Team

By far, the first consideration is the owner’s interest in staying engaged, interest in selling less than 100% of the business, willingness to accept new ideas, strategies and changes to the leadership team, as well as his or her competency.

Second would be the team developed by the owner/CEO. Roles and strategy can dramatically change with new ownership. Generally, the pace of growth expected far exceeds the historical results. If the owner and leadership team have been involved in multiple M&A transactions, this would be a real plus.

The acquirer may also want to add talent to the team like a new CEO or CFO. The owner’s role may be more in the M&A area; will the owner be comfortable is this new subservient role? Also, will the existing leadership team work well with the new leaders added by the acquirer?

The Buyer/Partner

To me, the only type of acquirer that would make sense here would be a private equity firm. Certainly, strong growth could occur with another type of buyer, but strategic buyers generally prefer to buy 100% of the company.

On the other hand, private equity often prefers the owner to stay in for a material portion of the equity. The owner needs to get comfortable that the private equity firm has generated strong historical growth success in acquiring and assimilating tuck-in acquisitions, as well as working positively with both the former owner and the new leadership team.

Key aspects of this growth plan could be much larger access to capital than what may have existed prior to the sale and the talent available to you from your private equity partner.

The Business/Industry

It’s also a huge plus if the company being sold has posted strong growth, successfully acquired in the recent past and is in an industry with significant M&A activity.

This would set the ideal conditions for the opportunity to obtain multiple bites of the apple.

Also, it can be a lot of fun. You have taken most of your equity off the table on the first sale and it’s safely tucked away. So, part of the fun is how much more aggressive you can be in growing the business with the partner assistance and additional capital available.

Shocking to many is that the second and third bites of the apple can be larger than the first sale.

R. Louis Schneeberger is executive chairman at Proformex. Over the past 40 years, he has played a lead role in more than 100 acquisitions, as well as the sale of more than 30 companies, public as well as private. He has done turnarounds, mergers and public offerings.


Related: Lou Schneeberger’s advice to first-time buyers