Have You Had a Career-Defining Moment?

I’m keen on learning about my professional connections and what led you to your current career. Why did you choose your career? Was there a person or defining moment that led you to this point?

Here’s mine and what I learned from it:

When I was 40 years old, I was working for one of the hottest startups in Seattle. In addition to my regular duties, I was also incubating a new product idea with the permission of my boss. It’s one of the great perks of working for certain technology companies, being allowed to spend up to 20% of your time pursuing your own ideas.

The idea proved viable, but it did not fit the strategic objectives of my employer. ?My boss gave me a choice. Spin it out as its own company with them taking a small equity position or forget it and get back to focusing on the mission at hand. My employer had designs on going public and I would do very well if the rollout was a success.

Right then I was contacted by a headhunter. Another hot shot startup that had just raised $40M was looking for a VP. Would I be interested? Why not, I thought. Keep all options open. I was offered the job at almost double my current salary and a boat load of stock options to boot. My wife and I were raising three young kids and could sure use the money. She said, “Don’t even think about it. Take the bird in hand!” There was no way to know if my employer would IPO or if my idea would get funded.

What do you think I did? What would you have done?!

Well, to everyone’s surprise, I opted to spin out my idea and start a company. No funding. No salary or benefits. Just a compelling idea that consumed me. It worked out very well in the end. It led me to an amazing career as a serial entrepreneur, angel investor, and mentor to many other startups.

The powerful lesson I learned from my defining moment is this:

Trust your instincts and stay true to YOUR dreams so you don’t end up devoting your life to someone else’s dreams.

I would love to hear YOUR defining moment!

P.S. My employer sold the equity they had in my spinout company for $1M, which gave them the cash they needed to cover their burn while negotiating an acquisition by Microsoft. It worked out well for them too!?