On Authenticity

Being authentic is difficult – for anyone and in any role. It is especially true as an enterprising person in any industry surrounded by strong personalities. Take for example first jobs out of undergrad or career changes, although more broadly it’s anything where you’re not Bill Gates or Warren Buffett.

It’s especially true because we’re taught to have role models.  We’re taught to have mentors.  We’re taught to ask for feedback, constructive criticism, and assessments.  All of these processes are meant to further our skills and balance; but I’ve learned they can also divert attention away from our individual strengths and greatness. There is a fundamental lack of focus on embracing who we actually are (although good mentors will further self-awareness).

Last week, I was fortunate to hear Andy Rappaport, founding partner of August Capital speak about authenticity.  Early in his career, he received feedback that he was too nice, would get run over, couldn’t negotiate hard enough, etc. And so he changed his tune – became hard lined, tougher, and grittier. In retrospect, he related, those were some of the toughest years of his life, and (although luck plays a large role) some of the poorest performing investments of his career. He reverted back to his authentic personality.

In my own career I have been the most confident – and most successful – when I relied deeply on my core values and instincts. When I joined Buzz Marketing Group way way back in 2003, I wore band tee shirts to meetings with executives at MTV and Sony (before it was cool!)  I remember asking my boss at the time if she was uncomfortable with my dress as she dressed formally. Her response made an impression on me, effectively – “We’re trying to project a credible image of a firm in touch with today’s youth market. So since you’re living in it, don’t pretend to be outside it.”

As I’ve entered the Venture world I’ll admit that my personality has begun to change. I’m naturally excitable and optimistic but I was taught that great VCs need to be cautious and pessimistic. I am naturally too nice, empathetic and giving, but, like Andy Rappaport, was warned I had to toughen up. In meetings, I’m typically on the quieter side, taking in a lot of data points, but making my words sharp and precise when I do speak (I learned this both from my father and poker), but was challenged to be more active and forceful.

Although there are definite truths in the feedback, I struggle pretending to be someone I’m not. This doesn’t mean we shouldn’t strive for improvement. But I do think it means we should aim for balance, relying on our personality strengths that make us great, while enacting barriers to prevent a weakness from hurting us.

For example, I can’t help it that I love getting excited about startups and new ideas. There are some meetings where I want to jump out my seat and hug the entrepreneur because their project fits my thesis perfectly (I don’t – maybe I should?). The balance for me is surrounding myself with colleagues who will quickly challenge me on holes I may have overlooked, as well as being upfront with entrepreneurs that while on first pass I’m enthusiastic, I have a lot of thinking and research to do.

Over the next few months I’m committed to focusing on self-awareness and how my values and strengths can be an asset to myself, my firm, and the companies we work with. But it’s also a balancing act – avoiding complacency in growth, or, worse, ignoring vital constructive criticism. In my view, it’s about losing the ego while remaining confident. I hope that’s the key to authenticity and I’m sure will find out over the coming decades.

About the author

Ezra Galston
Ezra Galston

Consumer focused hustling @Chicago Ventures, Young Entrepreneur @Foundation Capital, Class 18 @Kauffman Fellow, and Chicago Booth MBA. Former professional poker player, with 4 years experience doing marketing/biz dev in the online gaming industry. Launched a "poker hedge fund" in 2011, a record label in College, and produced a festival screened short film in 2006.

  • Nice post, Ezra.

    A lot of what you said certainly resonates with me. I think it’s especially tricky for someone who is trying to change career paths or enter a new industry. Culture-isms imbibed over years become part of a person’s personality and contribute to how they react to their environment. At the same time, they need to adapt to the expectations of their new environment while trying to stay true to themselves. Definitely an art.

Copyright © 2014. Created by Meks. Powered by WordPress.

Get BreakingVC To Your Inbox

Join hundreds of other operators & investors who get BreakingVC updates directly to their inbox.
Email address
Secure and Spam free...