Why I Became a VC and Joined PJC

Today I’m excited to announce that I’ve officially joined PJC as a General Partner. I’ve thought about becoming a VC for a long time. In fact, back in 2011 I was talking to my head of Sales at Backupify and we were discussing “doing what you love.” I talked about how what I really loved was business models. I loved the complex systems aspect of business – how go-to-market and product and customer segment and team all have to line up in the right way, and all the different levers you can pull to influence the business and the market. “That sounds like you want to be a VC” he said. I didn’t realize it at the time, but he was right.

When Backupify got acquired I was 38, and so was a good profile to become a VC. I like to write and network. I had founder/CEO experience, and had a good exit. And I was young enough to do it for a long time. Several firms approached me but it didn’t make sense at the time. So I decided to start Talla and do some angel investing with my friend Todd Earwood, through an entity we formed called Half Court Ventures.

Talla took much longer to get to product/market fit than Backupify, and in the process, I learned that I don’t really like the CEO job. At Backupify, I liked learning the CEO job, I didn’t actually like the things you do in that role. It’s a lot of culture building, a lot of people-stuff, and I’m a mediocre people manager.

On top of that, to be a good CEO, you have to have to like that feeling of walking into the office and being THE guy/gal that everyone wants to talk to. You go to an event and everyone wants your attention. You have a press release and everyone wants to talk to you. While I am not shy, I am a heavy introvert, and I get energized from reading, writing, thinking, etc, so, the social/political burden of being CEO, the people stuff, it weighed on me. I’m happy to be moving to a role where I can play supporting cast instead.

But what I learned making 74 angel investments with Todd over the past 5 years is that I really really loved the investing side. I often have unique insights about markets and as an entrepreneur I could act on one of those insights. As a VC I can act on many of them. And being a natural contrarian, very comfortable going against the crowd, VC is a better fit. As a CEO, trying contrarian tactics is a difficult thing to get a team to swallow. As a VC, betting on a company you believe in that everyone else doesn’t can get you a big win.

This summer, I decided it was the right time to hire a CEO for Talla, and was able to find an excellent candidate (stay tuned for the announcement). I talked to a few firms but, PJC was the right fit for a few reasons. First of all, PJC was a small firm that wants to build. It piqued my entrepreneurial nature to grow something, and meant I could go in as a legitimate partner and do deals, not be a junior partner who had to spend years proving myself.

Secondly, PJC is one of those Boston based firms that does deals everywhere. A lot of firms are focused just on Boston, or just the East Coast. I like the flexibility of finding the best deals anywhere. About half of my angel deals are west coast, so I am excited to maintain an investing presence there.

Third, PJC is a very flexible firm that will do many types of deals. Some VC firms have very narrow ownership targets and deal criteria. While we do have those at PJC, the range is a lot broader than most funds.

VCs get a bad rap, for a lot of reasons. And while I too have had some bad experiences with VCs, I’ve also had some fantastic ones, and I hope I can be one of those helpful VCs, rather than one that is draining to work with.

I’m excited to start this new chapter, and so if you are building early stage AI or B2B companies, please reach out.

I also want to thank all the people that helped me get here. There are way too many to mention but a few who stand out are my partner at Half Court, Todd Earwood, who was always free to discuss and debate business ideas (he is joining PJC too as a operating partner). Jamie Goldstein from Pillar taught me a lot about investing by letting me be a venture partner there for 2 years. David Orfao, Rich Levandov, Brady Bohrmann, and Rudina Seseri were all mentors of sorts who taught me pieces about investing. Dharmesh Shah and Jason Calacanis were instrumental and supportive of my early angel investing and gave me great advice about how to go about it. Jeff Bussgang was one of my biggest advocates years ago when I moved here from KY in 2010, and helped me get plugged in to the Boston ecosystem. Kent Bennett and Eric Paley were helpful as I thought through the transition from Operator to Investor. Phil Beauregard always challenged me, pushed me, debated me, and showed me some good deals along the way as I was angel investing. Vivjan Myrto started investing in AI even earlier than I did so meeting him convinced me I wasn’t crazy to focus on AI back in 2015. And of course I want to thank David Martirano and Matt Hayes for having me join them in their partnership.

I think I’ve also knocked heads with everyone on that list above at some point, and so, have been very lucky to have the kinds of supportive people who tolerate strongly opinionated people around them. So thank you all for your help getting me to this point, despite that fact that I have aggravated the hell out of all of you at times.

I’ll be writing more about the specific theses I have and where I am investing at PJC, in addition to a final advice post for entrepreneurs that I want to write before I am gone too long from that side of the table. Stay tuned.

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