As I’m sure any entrepreneur would love to do, I’d give anything to step back in time 12 years and have a chat with my 21 year old self. And while I can’t do that I do love to share lessons with as many young entrepreneurs as I can. I’ve spoken a bunch at colleges and other organizations for young entrepreneurs. I love passing along lessons while realizing that my experience is far from complete and I have many lessons yet to learn. Still, here are 5 things I’d tell myself if I could step back to 1997 and take myself out for coffee (yes, I know that sounds strange…)

#1 – Take as much risk as you can as early in life as you can. My choice at the time was to either be an investment banker or start a company with some friends. Starting a company sounded way riskier. Which is the main reason why I think I took it. Yogi Berra may have said when you come to a fork in the road take it but I’d merely add when you come to a fork in the road take the riskier path.

I’m not talking stupid risks. But smart, calculated ones. Look, at some point in your life you’ll have kids and a mortgage and a spouse who might not be super understanding of your crazy business ideas. But when you’re young you usually don’t have any of those things. Which means you can swing for the fences. Please do so. I promise you won’t regret it. Read the rest of this entry »