Dan Dunn

Only 3 posts last month – yikes. You’d think being unemployed, I’d have nothing to do but write, but it didn’t work that way at all. It was a very busy few weeks. I spent a few days helping Paul out in his apartment. I helped get my grandmother moved into an assisted living facility (with the daunting task of the house still looming). I caught up a bit on my unread book pile. I did some organizing around my house, including filing 6 years of Town Meeting paper. I dogsitted for a couple weeks, and visited Brian and Su in Newburyport.

I went to New York and visited Glen, the first time I’d seen him since Doug’s wedding. I similarly caught up with Amy (When Amy was here, we ended up doing shots with the just-championed Celtics under the bleachers at Fenway before they threw out the first pitch – a scene that cannot be described even with pictures).

When I left HP, I told people (and myself) that I wanted a leisurely June, and then start a job search. But back in May, even before I left HP, I got an email from Brian Halligan at HubSpot. I went in and visited him and his co-founder, Dharmesh Shah. We had a very interesting discussion. I liked both of them, liked the way they asked and answered questions, and liked their business idea. We followed up in email, and I came in to meet a second set of people. It continued to feel like a really good fit and they agreed.

Still, I was conflicted. I’d been aiming for something really risky, like starting a company or finding a really early-stage company that I could help grow. HubSpot was more established – 30ish people, two rounds of funding, hundreds of customers (!), etc. It wasn’t as small/early as I had been thinking of. The role they were trying to fill was right in my wheelhouse – improving the customer experience through analytics, UI improvements, feature selection, and QA. And the people were good. And the idea was good. And they had traction in the market. You can see the appeal.

I talked it over with friends and former co-workers, from founders to followers. Ironically, Dharmesh was providing his own argument for me to pass on the job: “Be an entrepreneur, not a wannabepreneur,” he wrote. I talked to Jason Butler as he’s starting up at Serendeputy. I had a couple dozen great conversations on the decision – it’s great to have friends and colleagues to help you sort out your own thinking (thanks, everyone). In the end, it felt silly to pass up a prospect like this just because it didn’t fit “the plan.” I couldn’t go wrong with a good team of people working on a good idea.

So I started on Monday – I’ve had four days of work so far. My days have consisted of meeting with person after person while they dumped as much information on me as they could in the hour or two that was allotted. I’m putting it all together in my head as quickly as I can before it leaks out. The business has more complexity than I had expected, both in strategy and in technology. There are a lot of moving parts. I’ve identified many places where I can help. The trickier part will be to figure out which ones are the right ones to tackle.

When I went to bed on Tuesday night (after day 2), I realized that I was looking forward to going to work in the morning. It was a great feeling.

HubSpot is in Kendall Square. Here is the view from my desk, and from the window: