If This VC Sold His Company Today, He'd Do These Things Differently

Five years ago, I sold my startup and started working in venture capital. And while that sale made me very happy, it didn’t make me all that wealthy -- especially not compared with the deals I see now, where big funding rounds and lucrative exits carry the day. So sometimes I wonder: What would I have done differently in my company if I could go back five years? Now that I’m working in VC, what bits of wisdom do I have now that I wish I had then?

Related: Know When and How to Sell Your Business

Here’s the first insight: Define “success” very early. Is it money? Changing the world? What do you want -- and what, realistically, do you think is possible? I had built a company that sold gift cards over the internet; it was a fine idea, but not a world-changing one. It was never going to be the next Facebook. When I finally realized the limits of my company, the truth was hard to swallow. But it didn’t need to be! I wish I had taken the time, at the very beginning, to put my actions in context. I had found a smart new way to sell an old product, and it was going to make me a few bucks. There’s nothing wrong with that -- unless you’re not willing to accept it.

So let’s say that, five years ago, I had defined my success. What should I have done next? This: Figure out what it would realistically take to get there. Again, I did this all wrong: Because I never defined success, I also never bothered to go out and beat my drum to find the appropriate financing to realize that success. It was a decision made out of fear; I didn’t want to be held accountable by anyone else. But without outside money, I couldn’t grow as big as I wanted. When an entrepreneur sets a goal, they need to be realistic: How much money will it take, and what percentage of your company and control are you willing to relinquish?

Related: 25 Tips for Having Meaningful Relationships

And here’s my final piece of advice to my younger self: Keep everything in perspective. Some people are consumed by their companies; they are their work, and nothing else. For them, I suppose, nothing else matters. But for everyone else (including me), that separation should matter. There were times while running my company that I realized the business was actually running me. I’d make compromises that would affect my happiness, or the happiness of people around me. I’d forget that these people -- and my relationships with them -- would be around long after the business closed. More than anything, the past five years as a VC have taught me the value of relationships: The ones I formed as a startup founder were important. Take care of the people you work with, and they’ll take care of you whether you succeed or fail.

I did OK. I certainly could have done better. But you, knowing all this, can now go out and do great.