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What I Learned as an EIR at Underscore VC

A number of months ago, I sat down to write a blog post for Underscore VC about the awesome opportunity I had around becoming the firm’s first Executive In Residence (EIR). Here I am, almost seven months to the day of that first blog post, and I’m writing again. This time, the reason is to look back at these great seven months I have had with Underscore as it is time for me to move on to my next opportunity as the Chief Customer Officer of Buildium, LLC. here in Boston. It is not a great surprise for me to be writing this blog post at this time because the EIR role, by definition, is one that is temporary. Thus, moving on at this time is the ‘normal’ next step for me. The fortunate thing for me, though, is that when I look back at my experiences, that is probably the only ‘normal’ aspect of being an EIR for Underscore that I experienced.

What An Incredible Time These Seven Months Have Been

When the Underscore team asked me to join their firm as their first EIR, I had a general idea and understanding of what an EIR “normally” did. Lucky for me, the team had some creative ideas and, just as they are doing with their overall firm, threw out the “normal” EIR book and allowed me to create an experience that was anything but normal. The experiences I have had surpassed all of my expectations and have allowed me to learn so much about the venture world, early stage companies and their founders, and, well, myself. Underscore opened up the firm to me and allowed me to soak up and contribute as much as I wanted. From the very first minute joining the firm, I felt like an integral and important part of the team and not just a temporary member. In fact, I should have known that things were not going to be ‘normal’ when Michael, on what was probably one of his most important nights — that of Underscore’s “unveiling” party, out of the blue asked me to step up and say some words to those in attendance who just so happened to be some of Boston’s most important entrepreneurs, investors, and corporate leaders.

Thanks to the Underscore team essentially throwing away that book as to what a ‘normal’ EIR tenure was to be, I have been able to create so many great memories over these seven months. I will cherish the memories of meeting an incredible number of entrepreneurs and working with them on their challenges, opportunities, and concerns. I will call on the flood of new learnings about the venture world and how this new and innovative venture firm (Underscore) is aiming to disrupt how the venture model operates. And finally, I will continue to grow and maintain the great friendships I established along the way with such a tight and special group of incredible professionals, leaders, and operators at Underscore.

The Takeaways From Seven Months

In addition to the memories, there are several key takeaways from my EIR time that I have added to my professional inventory on which I will most certainly call as I begin my next journey.

People and Relationships Matter Most — Reaffirmed Yet Again

I’ve always regarded the importance of people and relationships as important cornerstones of my leadership mantra. Before joining Underscore, I did not have a complete idea as to where people and relationships ranked in the venture world. In fact, if I’m being truly honest, I probably assumed that in the venture world people and relationships took a second seat to the prospects of huge returns and innovative ideas. Yes, I had heard various leaders in the venture world declare that people mattered; however, I was probably a little skeptical as to if this was true or simply “marketing speak” to make firms seem more personable and approachable. Well, I am a skeptic no more. I was truly flabbergasted (there is no hyperbole in that word here) with the amount of time that every single member of the Underscore team spent with the leaders and key members of prospective portfolio companies. I MEAN A LOT OF TIME. Over these past seven months, I have seen Underscore make decisions to NOT invest in companies doing really innovative and incredible things with the prospect of notable returns mainly because the leaders were not aligned or ‘in it for the right reasons’. I know these were very hard decisions for the team to to make — most certainly when they saw other venture firms investing in these companies later. However, they simply would not short change their belief that it all begins with the entrepreneur and his/her team. This cemented my own cornerstone leadership beliefs for if people and relationships mattered this much even in the venture world, their importance throughout industry is only reaffirmed.

No Template For Success

Over the past seven months I have been asked the following many times by founders: “Tell me how Constant Contact did it and let’s just apply it to my company.” Not. So. Fast. There is no one business model template that will guarantee success. Yes, if a company’s business model is SaaS based, there are key foundational elements, metrics, and processes that can be learned from the success we experienced while growing Constant Contact; however, the act of simply applying all of these to another company does not in any way guarantee success. The only “template” set of activities that can help increase the possibility of creating an enduring and successful company revolves around the idea of fully understanding your business model, your market, and how your solution can deliver incredible value to your customer. It falls to both the entrepreneur and the experienced leader to understand this and do everything that is needed to become the expert around their model, market, and product to develop their own appropriate template for success.

There is Always An Opportunity For Learning

Reading the above might evoke a “duh” reaction. However, these past seven months have been one so dense in learning that this idea most certainly merits its place on this takeaway list. My views and understanding as to entrepreneurship, early stage companies, venture, leadership, and personal development have been so augmented and enriched over these past seven months. It reminded me that no matter your experience, your level of success, or your career position, the opportunity for learning and improving yourself is always right there for you to take and it’s up to you whether you decide to take it or not. Underscore provided me an environment to take advantage of so many new opportunities that, as stated above, I feel I am now more ready than ever to take in on my next challenge.

There you have it. The time has now come for me to again thank the Underscore team , and all of the great leaders and entrepreneurs involved with Underscore for an incredible seven months. It has been a great honor to be the EIR for Underscore and I know that I will be a better leader and a better person because of my time with them all.