Five Years as an Angel

I woke up recently to the realization that I started doing this angel investing thing five years ago to the month. Motivation back then was to build a network and find a C-level position in an exciting startup. I did that dance with a couple of companies, but realized that I really didn't want to invest all my time in one highly risky endeavor, and also that, gee, that was a boatload of work!

So I've been doing the investing thing full time and pretty much full tilt. I've invested in more than 25 companies, most of which are still running. Three have officially closed their doors and three have had positive exits, none of them huge. A couple more are probably on their way out, while one or two will probably yield returns this coming year. Overall a pretty happy portfolio.

Last year I made six investments. Two were with Boston Harbor Angels, two with Walnut Ventures, and two were on my own recognizance. I'm proud to say that I was responsible for bringing three of the four group deals in. This happened primarily because I try to get myself in front of every entrepreneurship event possible: I speak at every opportunity (128ICG, TCN, CIC, Mass Challenge, Babson classes, etc), I mentor a bunch of companies and they refer their friends to me. And I'm willing to talk to any entrepreneur and give frank, and sometimes difficult to hear, feedback. And so far I've gotten nearly universal positive reaction from entrepreneurs.

So to return to 2012, I invested in Mosaic Archive, Kitsy Lane, SETEM, eSight, CoachUp, and Digital Life Technologies. I'm on the board at Mosaic, an observer at Kitsy Lane, and an advisor to SETEM. 

At the end of the year I found myself so busy with meetings that I decided that I needed to drop my membership in one of the three groups to which I belonged, so, with some regret, I chose to drop out of Launchpad. But I still keep in touch with many of my former colleagues there, and I'm sure we'll be collaborating on deals.e

I've learned a tremendous amount about investing and business since I started doing this. I have to say that I love learning new things every day. But that's the second best thing about my job. Topping that is the great people I've met and have the privilege of working with, from the great CEOs of the companies I see, to my colleagues in the investment community, to all of the people who are involved in the thriving ecosystem that is the Boston startup scene.

Small Investor with a Big Mouth

Boston Harbor Angels has a tradition of having everyone in the room introduce themselves at each meeting, which makes a lot of sense since BHA welcomes so many guests each month. A couple of years ago I began introducing myself as "a small investor with a big mouth." By now I feel that really is an accurate description of who I am in this ecosphere. 

My investment dollars will not move the needle on the required funding for a company; but sometimes the fact of my investment will be an indication that I've helped the company refine its pitch to the point that others will invest. I can say proudly that I've been followed into a few deals. Sadly, I can also say that I've led fellow angels to slaughter in at least one deal, but, unfortunately, that goes with the territory.

Copyright 1997-2018, Ben Littauer