Wearing Multiple Hats

Yesterday, I was honored to be asked to play the role of “Coach” at a start-up pitch event at CSpace in the Atlantic Wharf building in Boston called, ironically, #UNPITCH. I have attended a couple of times as a “friend” or co-sponsor through Boloco, but this is the first time I had my own table and a sign with my name and the title “Angel”. With 9 current investments in start-ups, and one successful exit under my belt, I guess it’s appropriate now. It was neat to see something other than “Boloco” underneath my name.

Of course, Boloco did sponsor the event. And I loved watching people stand in line to dig into Erin’s Goloco beautiful catering set up. I caught Erick G. setting up and he had so much pride in his work. I got a quick shot of him here.

In addition to being an Angel and a Sponsor, most of the time I’m actually just another Entrepreneur like the 60+ other entrepreneurs who showed up to get advice and coaching from Angels like me. So even as I did my best to provide good counsel, and I think I was able to for the most part, I was learning from them, too. With my second group of two entrepreneurs, we ended up spending our last 5 minutes talking about Worthee and they shared their thoughts with me. Mostly they probably realized that even with experience we are all still foggy on how to succeed… many incredibly successful entrepreneurs struggle to do the right things for entire careers. It’s part of the journey, part of what makes it such a thrill, for better and sometimes for worse.

It was good to see Scott Kirsner from boston.com and Phil Beauregard, both founders of the event. And to meet and spend time with Nick Belsito from OpenCity which I just made a small investment in through Branch Venture Partners. Kyle York from DYN and I recounted our last meeting in 2015… at Murphy’s in Hanover, NH where we ended up having a few too many with Matt Rightmire (Borealis Ventures) and Tony Florence (NEA) who joined us. The companies I met were all super interesting… Upper Glass, Plump Plum, Green City Growers, and Woodpecker. I hope to stay in touch with all of them and help if and where I can. The passion that founders bring to the table, literally and metaphorically, is contagious and I left feeling super motivated.

$42 for 2 HOURS… WTF?!

After paying the nose-bleed high $42 parking fee as I exited the garage of Atlantic Wharf (Boston Properties really isn’t my favorite), I put on my favorite hats of all: Husband and Dad. Maggie landed at Logan at 2:30pm after an exhilarating 2 week trip to India… she came back with a nose ring which took me all of 30 seconds to notice. It’s startling, at first, but its quite beautiful. This is who I married. We got home nearly 3 hours later to learn that Bo really likes the nose ring, but unfortunately Izzy rushed out of the room crying when she saw it. To each their own 🙂 But my hat of being a Husband and a Dad was the perfect way to end the day.