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

He did well, but could have done better.
If This VC Sold His Company Today, He'd Do These Things Differently
Image credit: Getty Images/Lee Woodgate
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This story appears in the December 2016 issue of Entrepreneur. Subscribe »

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. 

Edition: March 2017

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