After an awesome community-building party at Bessemer, I chatted outside in the cool of the night with an entrepreneur. Now, I’ve written before about this person (see “VC Arrogance: Inevitable?”). He is incredibly sharp. He mentioned something I’ve never heard before: “It’s very hard to have trusting and open relationships with other entrepreneurs.” He thinks
Category: Entrepreneurship
“How Much Money Should I Raise?” (and the Race between Fear and Greed)
An entrepreneur I know is thinking of leaving his current company to start a new one. He asked me how much money he should raise. I told him he should either raise a small amount of money or raise a very large one. A small round will be easier to raise, as you need only
Venture Cafe Office Hours on Oct. 18
I’ve long admired the work that Tim Rowe has done at the Cambridge Innovation Center (CIC). He does great stuff for entrepreneurs and the community. I remember he started the CIC just after the Web 1.0 Crash happened. People were literally rushing out of start-ups. Founders were dropping the “.com” suffixes from company names. Tim
Need Some Input: Coffee Connect with a VC?
I’m helping the New England Venture Capital Association (NEVCA). They lowered the bar, and I’m now on the Board. I’d like to come up with some events that entrepreneurs will find helpful. For me, the criteria are: open and inclusive, and helpful to the entrepreneur. Ideally, an entrepreneur spear-heads this, but I’m happy to do
Harvard, Rowing, and “Play to Win, Learn to Lose”
I had a Skype video with an entrepreneur last week. His company isn’t in a space we know well, but he came referred by a highly-regarded friend. So, I wanted to connect and try to help. I’m glad I did. Our conversation delved into sports. He used to row a lot. Think of large crews
The CEO Job Is the Loneliest
I was connecting with one of the TechStars companies recently. We were brainstorming about team dynamics and the dozens of Mentor pitches each company is doing right now in a compressed period. It is an intense time. “The CEO job is the loneliest,” I said. You see, you’re the firewall between the management team and