What I Would Have Told My Former Self

I often picture this Marty McFly moment where I'm sitting across from my 18-year-old self, this skinny pimply-faced kid who thought he could start an Internet company, and trying so hard to impart the wisdom that cost me decades to share.

It makes me wonder whether there could have been a directional shift if only someone was helpful enough to provide just the right advice at just the right time. It's what I've dedicated my whole life to in helping my fellow Founders, but still, I wonder if I could have helped myself.

If I only had three things I could tell this young fool — what would I say, and how do I think he would have taken it?

Lesson 1: "You have 50 Years"

I never realized how much time you really have to make an impact. When I was 18 I thought if I hadn't accomplished every life goal by 30, I was a wash-out.

What threw me back then was I hadn't had enough years on the planet (yet) to understand how many years we really do have, or more importantly, how to make use of the whole 50+, not just a single decade.

In 50 years, you can pretty much accomplish anything. But we're an impatient lot, and in the beginning, we don't realize what the cumulative effect of making forward progress over a long enough time can do.

Lesson 2: "Relationships Really Matter"

I never appreciated how important it was to build and maintain great relationships until I had enough decades to prove how invaluable they were. I'm constantly amazed at how often the perfect person I need to hire is someone I ran into 15 years ago, or the professional connection I need happens to be the best friend of a college buddy.

At first, I didn't see this one because my network was small, and I didn't have any opportunities to see how it paid dividends. But then, as my network grew, I soon had the ability to be "one degree away" from almost anyone in some bizarre manner. It's not because a whole bunch of people wanted to know me, that's for sure; it's because I made it a point to want to know everyone else.

I actually did a pretty good job of building relationships almost by accident, but if I had to do it all over again, I would have made cultivating and sustaining those relationships my primary goal. It's probably the one thing that has accelerated every aspect of being a Founder, from raising capital to staffing to always finding sage-like advice. There's nothing like it.

Lesson 3: "You can say 'No'"

When I was growing up, I never learned that you could say "No." If someone had work for you, you just took it because you needed money. If your boss worked you twice as hard, you just assumed that's what you were supposed to be doing.

Saying "No" was never in my vocabulary, and therefore "Yes" became the cost of being a Founder.

I should have said "No" a million times. To working with people I couldn't stand. To running my body into the ground over and over. To putting my personal finances at risk to make sure everyone else was safe but me. What I needed was someone to tell me how valuable saying "No" really was (to her credit, that was one of my wife's greatest achievements with me).

But it all begs the question — would I have listened? Nope. I wouldn't have. I would have looked at this old grizzled curmudgeon of a man, thanked him for his wisdom, and then blissfully ignored it all while taking countless years off my life. Hey, I said I wish I could tell my former self, I never said I'd be smart enough to listen!

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