Realistic Optimists

I am not sure who to credit for this saying, but I love it: “pessimists sound smart, optimists make money.”

Venture capital is an industry for optimists. It is about betting on the potential, on underdogs, on progress. We consider what a company can become, not simply what it is today. That requires a belief that the best is yet to come.

There are countless reasons why something won’t work, but optimists see the potential, run the experiment, and try to make it work. Experiments often fail. That failure is a lesson.

Thomas Edison made thousands of attempts to invent the lightbulb. In response to his missteps, he said, “I have not failed 10,000 times—I’ve successfully found 10,000 ways that will not work.”

Optimism and realism are not mutually exclusive, rather complementary. Most startups fail. The best understand the risks, welcome criticism, and have rigor and discipline behind their decisions. They know when to walk away or pivot. They look for opportunity, while seeing the world as it is and preparing for challenges.

Realistic optimism is a superpower. One of the most talented founders I work with, Tara Viswanathan, embodies this. Her optimism is infectious. It infuses the Rupa team and culture with energy, motivation, and hustle. Even customers, candidates, and partners feel the energy right away. It is powerful. Tara is also extremely realistic. She faces the facts head on, adapts quickly, and welcomes – even seeks out – criticism, with genuine desire to learn from it and improve. This is an invaluable competitive advantage. I learn a lot from Tara.

It is easy to fall victim to pessimism. The macro markets are uncertain, layoffs are happening left and right, and it can be hard to see the light at the end of the tunnel. But pessimism is a choice. And it usually leads to the status quo and mediocrity.

As I was writing this, I saw Tara’s latest tweet and smiled because it was so perfectly in character.

I am lucky to be in an inherently optimistic industry. It is both good business and a more pleasant mindset.

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