Q&A with Chuck Templeton

Chuck Templeton is a serial entrepreneur, founder of OpenTable, and former Director of Grubhub. He has started and advised numerous companies that are helping to build the kind of world that the Collaborative Fund envisions. We caught up with Chuck to get a quick history lesson on his journey building OpenTable and what led him to invest in Collaborative Fund.

Who was the first investor in OpenTable?

Sean Schickedanz. He wrote me a $75k check in our crappy office that was located down a back alley near 5th and Market in San Francisco. We had a one-room loft that was in the back of the building looking out into the alley and my other teammates were watching over their keyboards and computer screens,waiting to see if he would actually write (and hand over) the check! It was a great and vivid moment that I remember like it was yesterday.

At what point did you realize OpenTable was going to be a success?

We probably didn’t know until 2005 or 2006. It was a long time coming. You could see it working in some markets. (San Francisco, Chicago and NYC) but there was some concern on how far down to smaller markets it would travel. We all knew the model worked at scale, but the challenge was proving it could be taken to scale and still have cash in the bank.

Was it hard to transition from CEO to board member?

No, this was not a hard decision. While I was deeply passionate about the company, it was also the right time to transition. I didn’t have the experience nor the mentors to help me do what was needed for the sake of the company. I wanted to do whatever I could to “get it right” vs. “being right.” This was a very expensive business to build and we needed capital at a time when young CEO’s were going out of fashion and getting “grey hairs” into the business became important. Investors wanted to see more experienced people at the helm and I had no problem finding that person. Do I have any regrets? Not really. Could I have led it to the success it has seen today? Again, it is hard to say. But, I do know we had some amazing people like Thomas Layton and Jeff Jordan leading the company to the next level. I am happy with how it turned out.

What was it like to go public?

Really fun. It is amazing to see this idea that you started in your bedroom, sitting in your boxers writing the original business plan and seeing it flashing across screens in Times Square. But by that time, I was out of the company, so I didn’t get to see what the internal impacts were. I know that there were a lot of people who added a lot of value who didn’t do as well in the IPO as the value they provided to the company; and some people who got a lot more than the value they actually added. To some degree, that is how the markets are.

With hindsight, would you have done anything differently during the time of the IPO?

I would have tried to make sure that those who were there from the beginning, who did a lot of the heavy lifting, had a little bit bigger piece of the pie. I certainly was lucky, I could have been washed out, but a few people in the process made sure I wasn’t totally taken for. I am grateful. Again, that to me is the biggest problem with how these events work. But, the senior team and ultimately Jeff Jordan did an awesome job getting the company ready and out. I give them a lot of credit and thanks.

Let’s talk about today, do you think we are in a bubble?

It is hard to say. I am a bear, so I think every day the sky is going to fall. The difference with today is that most of the high fliers out there actually have revenue models and are making a ton of revenue. There are still some that are pure speculation, but the stakes are high for the winners and losers. As many of these ‘winner take all’ markets continue to grow and the consolidation of wealth continues to happen, some of these companies will have huge commercial value. If you can be part of those companies the value is high. So for the winners, no bubble, but for the losers, yes, big bubble.

What is your favorite Collaborative portfolio company?

This is a hard one. While I sit on the board of Getable and sat on the board of TaskRabbit, I can’t rightly pick either one of them. Both are great companies with great opportunities and great leaders at the helm. But I don’t know, there are so many cool ideas trying to make the world a better place. I just love the idea of Collaborative and what you stand for. Call me a Collaborative groupie.

Why did you invest in Collaborative?

I invested in Collaborative Fund because Collaborative is at the intersection of two areas I love: impact and start up. I think that the world needs some huge disruption and that old status quo of a carbon based economy, with greed and money at the center of it, is broken. We need every company to have impact weaved into the business model and fabric of the company. We must find new ways to be an inclusive equatable economy, where we work with each other instead of in competition of each other. As individuals, we only need to take what we need to survive. Nothing in nature, (which is older and certainly wiser) takes more than it needs. There is no waste.

Who is your favorite person to follow on twitter?

After @collabfund of course, it is @billmckibben and @350 for the great work they do on fighting climate change. They are fearless and courageous leaders out there on the front lines and pushing them forward. If the human race prospers beyond the next 25 to 50 years (see the Bear in me), it will be because of the great work of these two and others like them.