Keeping it Real

Two weekends ago, I traveled to Boulder, Colorado with a group of other venture capitalists for one of Reboot’s Bootcamps. Reboot is a newish organization launched by Jerry Colonna and they’ve led a few of these retreats for startup CEOs with good success, but this was the first time doing it for VCs. There were 14 of us from both coasts, some seed investors and some from larger funds, with a widely varied assortment of backgrounds and life experiences. Interestingly, most people there had been in the business for at least a few years and had achieved some level of success. The theme for the weekend was:

Practical Skills + Radical Self-Inquiry + Shared Experiences = Enhanced Leadership + Greater Resiliency

In the open, trusted and safe space we created, several themes emerged and repeated themselves. Since the time together was explicitly confidential, I can’t share specifics, but I came away from the experience feeling that as human beings broadly and members of the tech startup ecosystem specifically, we have some work to do on authenticity. The idea of imposter syndrome repeated itself several times during the weekend. Imposter syndrome refers to high-achieving individuals marked by an inability to internalize their accomplishments and a persistent fear of being exposed as a "fraud”. Reading that definition resonates for me, as I imagine it does for other high-achieving individuals reading this post. One of the ways many of us perpetuate the imposter syndrome in our day-to-day dialogue with friends and colleagues is in how we respond to common greetings. Q: "How are you?” A: “Awesome” "Great!” “Terrific!!” The notion that things are always awesome and that we’re all “crushing it” every day, all of the time is obviously not true and therefore, rings hollow when we try to perpetuate it. This mask that we’ve all been guilty of occasionally wearing prevents real connection and makes it difficult to help each other.

When an entrepreneur comes to pitch us, one of the things we look for is authenticity and honesty in the opportunities and challenges that lay ahead. We want to get to know how a founder thinks about problems and if all we hear is “we’re going to drive right through that mountain”, that feels artificial and lacks thoughtfulness. Over the past few years, some founders that pitch us have followed a fundraising playbook of sorts, taking advice from many startup-focused blogs that guide founders on how to build a deck, how to tell a story and, in some cases, how to speak. This can have the effect of making pitches sound rote, without any differentiation or special sauce. When this happens, we have a hard time getting a feel for the uniqueness and individuality that makes a founder who they are, which is the essence of what makes a founding story compelling. Not being yourself creates dissonance and/or a lack of passion in a pitch setting, and sometimes leads a VC to question whether the person is an entrepreneur or wantrepreneur. That distinction is relevant today, because it’s more fashionable than ever to start a company, but not everyone has the resolve to build so we as VCs are forced to have our radar up around this issue. As my friend, Bryce Roberts, explained so perfectly in this podcast “Be yourself. Everybody else is already taken.”

Steve posted a great writeup of the bootcamp weekend and the first takeaway on his list is the importance of 'connecting our inner and outer selves'. Said differently... be real. I know there’s pressure to put on a happy face, particularly in first meetings with VCs, but try to do so as authentically as possible because, otherwise, the dissonance that you risk creating can be deadly in a pitch. More important than the pitch, perpetuating that dissonance over time can lead to a general disconnect of our psyches and, in some cases, depression. For the good of all our mental health and emotional well being, in addition to maximizing the quality of experience with each other, we gotta change this behavior. Being authentic opens up possibility.

So what happened when 14 high-achieving VCs came together for three days of sharing in an open and safe space and made ourselves vulnerable? We established genuine connections, came to understand each other in a deeper way than we often get to experience in business relationships, and made some quality friendships that I imagine will last a long time. This is the power of authenticity and the reason it pays to keep it real.