On Imposter Syndrome — Letting Fear Drive You, Not Define You


Co-Founder / General Partner at

Equal Ventures

One of the more challenging items I’ve dealt with as my career matures is the feeling of belonging.

While it might be a surprise to many, the state where we are as a firm and where I am in my career has already wildly exceeded anything that I ever expected. To be clear, that is more a measure of my expectations than anything else. I was never the brightest student in the room and struggled academically. In college, I didn’t exactly have myself put together (at least, nowhere near the level of many folks in the industry or any of the folks I’ve hired). As I interviewed for various roles coming out of college and afterward, I remember hearing, “Why would I hire from the University of Richmond / Deloitte when I can get Harvard / McKinsey?” Simply put, if someone told me 10 years ago that I’d have the opportunity to sit on boards of incredible companies and be part of founding a firm like Equal, I simply wouldn’t have believed them. Sure it was my dream, but so was playing for the Yankees, who actually gets their dream?

Earlier this week I attended a summit for founders and investors that was surreal to me. Whilst there, I had lunch with one of my investing idols. To put it into context, this felt like the equivalent of the 8-year-old version of myself getting to play catch with Mickey Mantle. Admittedly, I was starstruck and nervous, hoping for nothing more than to not seem like a complete idiot in front of an investor that I’ve serially read and quoted countless times over the last decade of being an investor. I texted my wife about it and even she got emotional knowing how much an interaction like that meant to me.

I was fortunate to be with a few of my other founders at this particular event and later that evening, one of my founders said to me “Growing up, I never even knew anything like this existed, let alone believe that I would ever be part of it.” I replied, “Same here.” Much like this founder, ambitions for greatness weren’t realistic when I was growing up. I think back to all the times I was told “You don’t deserve this” or that I was a fool for pursuing something that I was so obviously out of reach. Today, those expressions have a material impact on me. As my career and our firm progress, I’m increasingly working with and/or competing against the firms and individuals that I’ve idolized. This is incredibly polarizing, simultaneously feeling that you’ve “made it” while feeling the nagging fear that you don’t belong. For many, that “fear” can be paralyzing.

To be honest, I almost didn’t meet this investing idol. I didn’t have the courage to go up to him (“what would he ever want to talk to me about?!”), I just got lucky that he decided to sit down at my table and strike up a conversation. I’ll be the first to admit that I have let that sense of fear inhibit opportunities. If I hadn’t been so incredibly lucky to have him sit down at my table, I would have missed out on an opportunity that I would have regretted for years. Am I working on it? Yes. Am I embarrassed by it? Of course. But I know countless others are as well. If nothing else, I want them to know they are not alone. We live in an industry driven by bravado in 90 seconds increments. But it’s who I am and if the pandemic (and Jerry Colonna) taught me anything it’s to be real about who you are. This is something that I, my peers and many founders/VCs FAR more successful than myself have struggled with, which is why I wanted to talk about it.

Along the way, I’ve learned that you can’t control how you feel, but you can control what you do with those feelings. Am I going to let fear define me or am I going to let it drive me? I want to be as grateful as I can for every second I get to do this job and to be vigilant as I can to earn my rightful place. When I entered this industry, I was happy to be just a part of this, but I’m choosing to let “fear” drive me towards a higher objective. I encourage the founders and VCs that I meet to do the same. I don’t want to hide the fact that I don’t feel that I “belong,” I want to rightfully earn my place amongst the established. As Equal matures, I think we are well on our way, and I know that I will work as hard as anybody in our business to earn our place in this industry. I NEVER want to feel comfortable — comfort is one step away from complacency. I want that imposter syndrome to drive me to work harder, be a better partner and help founders accomplish amazing things they otherwise wouldn’t. Ultimately, I know the only way I will overcome these fears and feel like I belong is by proving it and that is far more productive than pretending those feelings don’t exist.

While I recognize that likely means I’ll often remain nervous, awkward, over exerted. I will never have the coolness of Jobs, the courage of Musk or the charisma of Branson. But neither did Charlie Munger. All I can do is do my best to make up for that with the passion, sweat and resilience of being myself. Along the way, I get to approach each day being starstruck by the amazing founders, investors and stakeholders I get to work with every day. I’m going to treat every day in this job like I’m an 8-year-old getting the chance to play catch with Mickey Mantle and that feels pretty damn special.

NOTE: This article is just as much for those who struggle with impostor syndrome as it is for those who have ”made it.” Know the impact of your actions on others. A small gesture on your end can go a long way for someone struggling for their first inches of success. If you have the chance to help someone’s life, why would you not do it?

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