The Dangers of Burning Your Ships Behind You

By Glen Hellman

A question asked by a rookie start-up CEO: “Should I hedge my investment in my company?” I’m sorry, but that question forces me to pull out my nerdomness by quoting my favorite coach and mentor:

Master Yoda, “Try? There is no try; there is only do or do not!”

If you are leading a company and you are thinking about hedging, then here is the best hedging advice I can give you:

  1. Find A Ferociously Driven Replacement CEO — Hire him to replace you because you are not the right person to be leading your company to success.
  2. Get Out Of The Way — If you stay with the company all of your income and all of your future wealth based on company options are tied to one company. Go diversify your income and get a job. Being the CEO of a successful start-up isn’t a job, it is a quest, a calling, a passion. So go get yourself a job. Get out of the way of the CEO and go let him make you rich while you punch a clock.

You know that expression, “Don’t burn your bridges behind you?” That’s hedging your bet. When Cortes arrived in the new world, he didn’t hedge his bets; he burned his boats, totally committing himself and his team to finding El Dorado.

As the CEO of a start-up, your team needs to see you display the same dedication to success (which is not to say you should go out in the parking lot and burn their cars). They need to believe that there is an El Dorado. and that you will have the vision and the drive to take them there.

Your unquestioned dedication to reaching your goals must never be in doubt by your team. Sure, some days, you’ll question your sanity. Some days you’ll have doubts … that’s natural. But if you want your team to follow you through the fires of hell, that’s only going to happen if they believe in you, your vision and your commitment to make it happen. And that belief is not going to happen if you’re even thinking about hedging your bets

Glen Hellman is an angel investor, serial entrepreneur, and has worked for venture capitalists as a turn-around specialist. He’s a principal at Driven Forward, board member at the University of Maryland’s Dingman Center for Entrepreneurship, a Vistage coach, and a mentor at the Founder Institute. You can e-mail Hellman at
Originally published: Dec 12, 2011

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