VC 100

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
Magazine Contributor
Entrepreneur Contributor
3 min read

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. 

More from Entrepreneur

Grow Your Business at Entrepreneur LIVE! Join us on Nov. 16 in Brooklyn, NY, to learn from legends like Danica Patrick and Maria Sharapova, pitch our editors, meet with investors, and potentially walk away with funding!
Register here

One-on-one online sessions with our experts can help you start a business, grow your business, build your brand, fundraise and more.
Book Your Session

In as little as seven months, the Entrepreneur Authors program will turn your ideas and expertise into a professionally presented book.
Apply Now

Latest on Entrepreneur

My Queue

There are no Videos in your queue.

Click on the Add to next to any video to save to your queue.

There are no Articles in your queue.

Click on the Add to next to any article to save to your queue.

There are no Podcasts in your queue.

Click on the Add to next to any podcast episode to save to your queue.

You're not following any authors.

Click the Follow button on any author page to keep up with the latest content from your favorite authors.