Big risks can lead to big rewards in the C-suite

In this THINK Leaders podcast, he shares his journey to the C-suite, big career risks he has taken and why you should never get too comfortable at your job.

If you could name a seminal moment in your career, what would it be and how did it shape your path?
(1:54 – 2:55)

Probably a seminal moment would have been when I decided to leave working for a very big, well-established company and go across the country for a startup in Silicon Valley. Throwing caution to the wind and not knowing if that company would be there a few months later and that was a big risk for me—a calculated risk, but a big risk for me.

And of course now looking back I am very glad I did it and it turned out very nicely for me. But in going from a very large established company to something that was small, growing very quickly, where as the CIO/CTO I had to do every job because there was nobody to delegate it to. You learn how to do a lot of different things, you learn how to do them quickly, and you learn what’s important and what’s not and how to cut to the chase very quickly.

What was holding you back from taking that risk?
(3:09 – 3:40)

The fact that the job might not exist and you might have to look for a new job before you are ready to. But one never knows how these things might turn out.

Prior to that I turned down some really big names in the Internet that we would all recognize today and I’d be a really rich guy, but I was thinking a little too conservatively and analytically. And then I decided later that the moment was right and I just kind of jumped into the deep end of the pool to see how it would work.

What sacrifices did you have to make to reach this station?
(3:58 – 4:20)

This particular job was in Silicon Valley and I live in Chicago, so rather than move my entire family out to Silicon Valley and maybe accentuate the risk, I decided to have a commuter lifestyle. Which worked fine from a work standpoint, but it means you are away from your family for long period of time, which is not ideal either. But that is a conscious trade off I made to try and build for the future.

What advice would you give future leaders aspiring to be in the C-suite?
(4:21 – 5:50)

Never get too comfortable, because if you get too comfortable in your current job, some people might like that, but I think then you’re not learning and you’re not challenging yourself. During the course of my career I’ve moved from companies in the same industries, companies in different industries, always seeking new challenges because I wanted to constantly push the envelope on what I was capable of doing and how I could add value.

How has your role as CTO changed since 1998 when you took on your first position?
(5:04 – 5:55)

The major thing that has changed, and as technologists we all know this, is that technology is changing and the pace at which it changes continues to increase. It makes it very exciting but it also makes it very hard to make the right decisions at the right time. To know when to pass on something, know when to jump on something early rather than wait to see it’s proven, and balance all the costs and risk associated with making a decision or not making a decision.

I’ve said that in some of the jobs I’ve worked that some of the things that we need to do are like an extreme sport. It’s not for everybody, but boy, the adrenaline rush is really great and hopefully most things work out.

What three adjectives would your employees use to describe you?
(5:55 -6:10)

I would say, in no particular order, smart, goal-oriented or result-oriented and funny.

And what qualities would you seek in employees?
(6:22 – 6:47)

I’m looking for people that are talented and look at their jobs as more than a paycheck. They really want to succeed personally, both for them (for the satisfaction of succeeding), and for making the company successful. When you have a team like that, that wants to make sure everything works to best of their ability, those are great people to work with.