Jerry Colonna’s Psychological Insights For The Entrepreneurial

I’d never heard of Jerry Colonna before yesterday. Apparently, he was a good VC. I was in the car for a long time Saturday morning, so I fired up Swell and @Jason’s episode came up, and I listened [audio episode]. This was a different style of interview, and I was hooked pretty early on because Colonna started with a historical perspective from the first wave of Internet investing, and was very open about his own personal and professional failures. For the next 80 minutes, Jason and Colonna had a terrific conversation — open, thoughtful, emotional. It’s so good, in fact, I listened to it again this morning in order to capture the main points Colonna discussed, because I believe this is extremely important for anyone working in/around startups to pay attention to yet is not often discussed or articulated so well. Below are my main takeaways, and thank you again to Colonna for his insights and to Jason for making this happen:

  1. The randomness at which luck is “distributed” is unsettling. It applies a kind of uncertainty that scares people, especially entrepreneurs who think they can will things into existence. We believe in our primal, intellectual ability to figure out everything, but it doesn’t always work that way. We like the idea we can be clever, but the distribution of luck oftentimes doesn’t care about how clever someone is.
  2. Many cover their anxiety with aggressiveness, especially struggling CEOs and VCs with struggling companies. One of the biggest mistakes founders make is not telling their investors their truth, and investors are complicit. One of the biggest mistakes investors make is acting aggressively when an investment isn’t going well, which is usually motivated by an anxiety that they will lose money.
  3. For the most-driven people, oftentimes their motivations are driven by fighting childhood demons. They go so far to suggest that investors are even looking for people with an insane level of drive, people with neuroses (the good kind).
  4. Many entrepreneurs who make it or could have a shot to make it may experience “Imposter Syndrome” – I’d never heard of this before. Fascinating.
  5. There’s a magic and risk when fully blending one’s self with their work. The magic is that the sum becomes more powerful than the parts, that serendipitous things happen that can launch a career or business. The risk is that we can ignore our health, our happiness, our relationships, and everything else.
  6. Adrenaline does not help creativity, it helps humans in specific fight or flight situations.
  7. True leaders own their narrative, recognize their own motivations, and are then able to lead diverse groups of people because they can make emotional connections to motivate others to realize a bigger goal. This is kind of cliche, but the way he explains it is great.
  8. Finally, my favorite: We must not confuse resilience with stubbornness. Resilience is obviously important for entrepreneurs. Resiliency is the ability to withstand the vagaries of everyday life, whereas stubbornness is about saying “I’m going to keep doing what I’m doing” no matters what others say, what the markets say, and what the facts say, which is all problematic because it’s too easy to overlay this mode of thinking on top of the tiny fraction of entrepreneurs who succeed. This can make others become more arrogant, more brash, and more in denial. Stubbornness is not changing your mind when the conditions change, while resilience is having the intellectual capacity to not be phased by changing conditions, but also to thrive in them, to thrive on the uncertainty and to transform it into opportunity.