Startup Grind
derek andersen
Charles River Ventures
George Zachary

Should You Trust Your Gut? The Answer Is Yes.

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Editor’s note: Derek Andersen is the founder of Startup Grind, a 30-city event series hosted in 15-countries that educates, inspires, and connects entrepreneurs. He’s ex-Electronic Arts and the founder of Commonred.

A few years ago I asked a successful entrepreneur for advice on what I should do with my latest product idea. His reply was simple. “Trust your gut. What does your gut tell you?” I confidently replied, “That this is a $100MM business.” To which he added, “Then go for it.”

So that’s exactly what we did. We went for it and a year later we didn’t have a $100MM business or even a $10MM business. We didn’t even have a….ok I’ll stop there. But how did I get it so wrong? Is my gut untrustable? Was I wrong to follow it? Or was my stomach just acting up after a recent trip overseas? I recently sat down with Charles River Ventures Partner George Zachary who has had his fair share of big successes.

In his 17-year venture capital career, he has had over $1B in returns on $150MM in investments. He is an investor in companies like Twitter, Yammer, Playdom, Jambool, and a lot more you’ve heard of. This subject is one George has preached for a long time.

“Listening to my gut is the right thing to do for me. It doesn’t mean it’s going to work out.  But it does mean that’s what I should follow,” he told me a few weeks ago at Startup Grind in San Francisco. “That’s my passion. When I’ve done that it has worked well. When I’ve followed my brain and not my heart it’s resulted in disaster and failure every time. I’ve had no success operating from making a rational decision or a decision based on fear. It’s all come from listening to my gut and intuition.”

George isn’t the only person with this creed. Steve Jobs famously said at the Stanford Commencement Address in 2005, “You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”

But that’s Steve Jobs. For the rest of us normals some times it does let us down or so it appears. Like when your gut tells you that you’re building the next great product of this generation, and after 3-months you have 1,000 users, most of which were college friends, extended family, and creepy ex-girlfriends who still can’t let it go. You know who you are.

For someone with his level of success, George is surprisingly honest and frank about his failures. Despite their friendship, George didn’t invest in one of Elon Musk’s early companies X.com which he says was a mistake. He had an opportunity to lead Twitter’s Series A at a $25MM valuation (eventually taken by Fred Wilson at USV), but he did invest a smaller amount.

“A lot of the mistakes I’ve made at acting out of my gut, led to important things that I’ve needed to learn to get better. I’m not so sure there’s any divine purpose or anything behind it, but what I do know is that by learning through my mistakes I’ve tended to get better,” George says. “There’s no science to it, there’s no 64,000 variable algorithm to investing. If there was then I’d be doing it and so would everyone else. My investing algorithm is: Do I feel more energized at the end of the meeting than at the beginning of the meeting? That is all it is. There is nothing more.”

In 17-years of investing, his gut is a solid bet. George was a founder of Shutterfly which eventually went public. He was one of the few Odeo investors that managed to also invest in Twitter. He backed David Sacks at Yammer and Geni. He’s an investor in Millennial Media. Early in his career he even nearly managed to convince his firm to invest early in Google but was outvoted by the other partners. His gut approach is working just fine.

So back to my original experience. Yes I followed my gut, and yes I failed at building a massive company with it. But I learned all sorts of things. I worked with a dozen engineers refining my product management skills. We had lots of small wins which taught us we have what it takes but this was the wrong mixture. I solidified my relationship with my co-founder and we’re battle scarred taking on the next thing. I earned my startup education through blood, sweat and tears, and we were able to eventually sell the product at a small financial but massive moral victory. Not a $100MM, but it was the right decision for me at that time and my gut was still right. So next time you’re in doubt about the right decision, remember George’s advice on the cause of his success, “It’s all come from listening to my gut and intuition.”