Finding Strength through Vulnerability

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I was with an industry colleague the other day and they asked me about my recent post “On Communication”. This is someone that I’ve known for over a decade and they had no clue about my verbal difficulties. They expanded a bit upon my openness and remarked about how different I seemed from when we first met. They asked what happened, what changed me?

The truth is…I broke. My past is full of a lot of self-doubt and a lot of doubt from some of the folks closest to me. I won’t go into that, but my path to where I am today was not straightforward. Over those years, I hardened. I put armor up to protect myself from the inevitable disappointments. Who was I to believe that I belonged in this world of venture capital - full of folks who had gone to the best schools, worked at the best firms and to have done so seemingly effortlessly, whereas even the most miniscule of progress felt so impossibly difficult to me. I worked my ass off, kept my head down and felt I was always one inch away from being exposed as an impostor. I felt that the best I could do was replicate the practices of others to hold onto my seat for as long as I could in a world where I had no right to exist.

Over COVID, my ability to hide all of this broke down. I was exhausted. I was a new parent with a new fund. After nearly 2 years of raising Equal 1 (which was a brutal process), we announced our fund in the beginning of March 2020 only to see the world collapse mere days later. There was no break or reprieve – just straight back into madness. My mother-in-law was battling pancreatic cancer and my wife/I decided it was important to shelter in place with her in the event that something happened. Today, she is alive and well, but there were many times during both our fundraise and that first year of Equal where that seemed like a near impossibility. After going through a brutal fundraise and the traumatic near-death experience of a loved one (that included several weeks in a coma during our fundraise, unbeknownst to even our closest LPs), the pandemic hitting the week after our fund was announced felt like a knockout punch.

Because my mother-in-law was immunocompromised, our family sheltered in place with extreme caution and isolation. It was hard. Amidst one of the endless Zooms I was on, someone asked me how I was doing and instead of saying the usual benign response, I told them how I was actually doing…”To be honest, I’m really struggling.” We stopped talking shop and we unloaded on each other about what was actually going on in our lives. We ended up pulling together a small group of peers and agreed to meet monthly over Zoom. Perhaps it was through sheer exhaustion, but our group became remarkably honest with each other very quickly. This felt like a huge weight off my shoulders, the first time I could be my true self with the people I worked with. Simultaneously, I had been running the Emerging Manager Circle and progressively started opening up to members of the group, realizing many of them were dealing with the same challenges I was. I had read and re-read Reboot by Jerry Colonna and asked him to do a session with me in front of the group. Jerry opened the session asking, “Who thinks I can get Rick to cry in the first 5 minutes?” He succeeded...in front of over a hundred fellow emerging managers. I was done carrying the armor…I let go and stopped trying to pretend to be what I thought I should be and started being the person I was.

What I was, was different from a lot of other VCs. For better or worse, I had a different set of experiences and networks. I will never stop learning from the best practices of others, but recognized I was pushing a boulder up a hill playing a game where I wasn’t positioned to win and that left me feeling inadequate. I felt that myself and our team had to find ways to play our game, not theirs. My peer group helped me discover what that was and embrace it. They were the ones who told me to start writing given some of the communication struggles I had (up until then I had written only a few generic blog posts), the ones who encouraged me and our firm to share our research (rather than fearing judgement of others) and the ones to encourage me and our firm to lean in on what made us different. While not everyone would accept this, some (far more than I would have guessed) would.

I believe both myself and our firm are stronger for that. Not because our playbook is better than others (lots of ways to play this game), but because we are being ourselves. I am imperfect in so many ways. To hone back to the “On Communication” post that prompted this, I will never be the orator I wish I could be, it’s just not something I was blessed with. My faults and deficiencies beyond that are endless. But rather than hide them under the covers, I’m trying to embrace them to be the truest version of myself. With that, I believe the ability to lean in on what is authentic to oneself creates a compounding effect…to get just a little better each day. Myself and our team are trying to build the strongest version of ourselves, rather than chasing the endless onslaught of advancements by others. Myself and our firm can’t control where we started, but I believe this process has given us greater agency and effect to where we are going and slope matters a helluva lot in this business. If nothing else, I no longer feel like an impostor. Whether we win or lose, we’re playing our own game, not someone else’s.

With Thanksgiving this past week, I’ve thought a lot about what I’m thankful for. There are so many things. I have a wonderful family with two beautiful children and an amazing wife (who has always believed in me and has patiently helped steward me through this wild journey). I work with amazing people every day across our firm, portfolio and LPs. I have a blessed life. But for some reason, it struck me how thankful I am for the ability to be authentic to myself and to work with folks who embrace that. To be able to embrace my vulnerabilities (and presumably some relative strengths), rather than to hide them and conform to the mold of others that I will never match up to. To not have to worry about carrying the weight of the armor I did for the first 35 years of my life (I’m now approaching 40). To be myself. I know there are endless others (in our field and others) who feel they still need to carry that armor, so regardless of whether my vulnerability was the consequence of intention or exhaustion, I’m thankful for it.

I hear that “the only way to build muscle is to exhaust it to the point of failure”, so I’m oddly thankful for my failures. Every knock out punch that was thrown my way led me to where I am today - absent of the armor, but stronger for it.

I believe there is strength in vulnerability. Stepping out like this (and as I’ve done progressively a bit more over the last few years) is terrifying, but often necessary. I’m hopeful that sharing a bit of my journey will help others with their own. If any of this resonates with you, I would encourage you to unveil the armor and share more of your authentic self with the folks you work with. We’re all humans and we’re all unique snowflakes. When you embrace that, you might just be surprised at the support you get from others. If nothing else, you’ll have the peace of mind that you’re playing your own game and being the most authentic version of yourself.