This past Thursday night, the Massachusetts Technology Leadership Council held their annual awards. See Scott Kirsner’s blog for a full list of award recipients.
I was very happy to learn that my friend and colleague Doug Levin, the CEO of Black Duck Software won the award for CEO of the year. Doug wrote a post about winning the award — interestingly titled “My Psalm.” It’s nice to see Doug credit Team Black Duck for his award.
I’ve known Doug for more than five years now. We met at the University of North Carolina, where he taught a class on entreprenuership. I actually didn’t take the class, but I reached out to him privately to get to know him. I was moving to Boston within the year, and Doug and I had similar backgrounds and interests.
What followed over the next few years was a number of breakfast meetings, where we traded stories and talked about technology. Before Black Duck began, Doug was interested in the open source community as a whole and we talked about how the software industry would change as a result of open source. During that time I got to know Doug pretty well.
Here’s the deal with Doug: if you can’t take the honest (often brutal) truth, you shouldn’t hang out with Doug. He tells it *exactly* like it is from his point of view, often using descriptive analogies to illustrate his point. He does not mince words — if he thinks you’re doing something stupid he’ll tell you. Be prepared for him to quickly point out your faults with extraordinary detail, and suggest an alternative path that often seems unachievable.
Allow me to illustrate: Doug and I met for breakfast in mid 2006 when I was trying to get Punchbowl off of the ground (just checked my notes: it was 6/28/06). We had gone for a while without meeting — he was knee-deep in Black Duck, and I didn’t feel like I was ready to talk to him about Punchbowl. At that meeting, I described to Doug our progress to date. I was proud of what we had done without any funding — and was ready to show him the plan. Doug took one look at it and point-blank told me that I needed to upgrade the plan to make it attractive to potential VC’s. Then he challenged me to go get someone like Intel Capital to say that they would be interested in being involved in a Series B. I left that meeting feeling frustrated. He hadn’t really acknowledged our progress to date, and had suggested a path that seemed entirely unachieveable.
Looking back, I wish I had pushed Doug after that meeting to help me more. I didn’t know at that point how to “upgrade the plan.” I didn’t know how to get VC’s really interested. Doug suggested that I try to get Intel Capital interested in a later-stage round of funding. But I was looking for seed-stage money. How could I engage Intel at this early-stage?
What transpired over the next 12 months was a steep learning curve and lots of starts and stops. I met with lots of seed-stage investors, was rejected more times than I care to admit, and faced an everyday challenge to keep my head up. If I had met with Doug again, he could have helped me upgrade the plan. He would have shown me a path to success faster than I could on my own. He would have given me the brutal truth.
Eventually I got an introduction to Intel Capital on my own, and the rest is history. Here’s the ultimate irony: I just checked my notes: it was one year to the day from that breakfast meeting with Doug when we finally received a term sheet from Intel. Wow. With our closing on October 1st, it took me 15 months to make the unachievable happen.
There is a reason that Doug won the CEO of the year. He knows how to accelerate success. He thinks big, and does not mince words. He has the ability to evaluate a situation quickly and offer ideas and solutions. But most of all, he tells you the brutal truth — even if it takes you a while to figure out how to achieve the seemingly unachieveable.