Nearly a decade ago, a member of my Executive Team walked into my office with a no-win situation.

Here’s what it looked like:

I either restructured his ownership in the company, essentially doubling what he had been granted already — or he packed up his bag of tricks, shook some hands, wished everyone well…and quit stage left.

Providing him the equity he was asking for was impossible; he would end up with more ownership than any other executive. Not to mention it would require a Board Vote, an increase to the option pool, and dilution for every single person in the company.

He was valuable but, well, not to everyone else’s detriment...