Why Learning Optimism

I am not an optimist by nature. It’s the one gene that I would have loved to get from my father, but didn’t (my mom is squarely in the not-a-natural optimist camp with me.)

The other day I had lunch with my dad. He is also an entrepreneur (a scientist-turned-entrepreneur) and his company has been going through one of those extremely stressful new-strategy-new-CEO periods. He was anxious and worried, but as we talked about it, he had this strangely-peaceful look on his face. “I tend to believe that things will work out in the end,” he said and there it was: That’s the gene I didn’t get.

For the past five years I was a Managing Director with an early-stage venture capital firm. I spent my time learning about different technology companies and business models, meeting with entrepreneurial teams, evaluating companies for investment, and working closely with the companies that were part of our portfolio. One thing I learned was that even if I had been an optimist, spending five years in venture capital would have knocked it out of me cold. I saw too many companies and business models fail, lose money, or go out of business to believe that things will work themselves out in the end.

Someone whose thinking I’ve come to respect recently said that the difference between venture capitalists and entrepreneurs is that pessimism makes a good VC and optimism makes a good entrepreneur. I agree, but I take it a step further. Optimism doesn’t just make a good entrepreneur; without some degree of optimism, it’s not possible to become an entrepreneur.

And that is why this blog is called Learning Optimism. It is what I am now doing. After five years I left the safety — and the large paycheck and big office and many nice lunches — of venture capital to become an entrepreneur and explore a completely unknown to me world of social media and blogging.  I started a company called Work It, Mom!, which is now the leading online community for working moms. I became a blogger and not a horrible one at that. I’ve recently joined an awesome new startup, Daily Grommet, as the Chief Community Officer. Yes, I am drinking all the Web 2.0 and social media Kool-aid in big gulps.

The experience of getting a start-up off the ground on a tiny amount of angel capital, in one of the toughest economic climates in history has been incredible, amazing, and excruciatingly difficult all at the same time.  Along the way, I have discovered many skills I need to sharpen learn, sometimes from scratch. And one of those skills, perhaps one of the most important ones, is optimism.

I know that optimism is not usually referred to as a skill, but that’s how I think of it. It is not something I naturally possess but it is something that I absolutely need to learn to succeed survive in my new career path as a social media entrepreneur and professional. Oddly enough, I feel like I am getting the hang of it already.