Don't Cash Out

I coach a lot of leaders, and 2020 was a beast for many of them. As I sit here thinking about what separated the leaders who thrived from those who lost ground, one thing keeps coming up: how they think about the finish line.

I talk to a lot of successful leaders in the twilight of their careers. They've worked hard, paid the price, and many of them are, quite frankly, tired. A lot of them are holding on to hit that certain number whereby they can retire and live the lifestyle they want. Many are looking to sell their businesses to make that happen — hence the rise of the Private Equity market: a 400% increase in the number of PE firms since 2000, with $8.2 trillion currently under management.

“Leaving a thriving company for the next generation to lead is its own sign of success.”

PE-run companies have a much higher stress, much lower employee satisfaction rating. It's pretty obvious why. PE firms buy low-risk companies with established markets and then squeeze in the name of "efficiency" and short-term profits. That's the game.

I want to speak to the folks who are thinking about selling to these PE firms. You've perhaps been sold the idea that early retirement is a sign of success. I want to offer a different sign of success: leaving a thriving company for a next generation to lead.

This takes planning and intention. But it's not impossible. I know plenty of twilight leaders who have planned for this. These next-gen minded leaders are still tired. They sometimes want to give up, sell out, and ride off into whatever sunset they can afford. But there's a joy and purpose in their heart. They are pouring out their wisdom, their time, and yes, even their own money, to give the next generation a fighting chance.

My message is simple: don't cash out. I know you're tired. I know you have your eye on that mountain home or that beachfront property. But please keep fighting. The next gen needs you.

This is the center of the heart behind why I started Rootstock. We want to help legacy leaders be wildly successful, human-rooted, and thrive for generations.

With love for the next gen,
Tony Woodall
Founder and Managing Partner, Rootstock