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Lee Jacobs—There Is Always a MoveAround two years ago, I spoke with a portfolio CEO who started his company at the same time I started Colingo. Though eight years had passed, he told me that his business wasn’t yet working. This conversation made me reflect on how seemingly so many of our peers have had incredible financial success.  Feeling a bit bad for myself, I expected him to share my sentiment.

Instead, he looked at me and said with a straight face, “I don’t worry about that at all. I know I am going to succeed.”  

He meant it. I left the conversation wondering how he could work on this business for eight years with no success and still believe in himself. Today, he is one of our most successful founders.

I recently met Ajay Ramachandran from Happiness Ventures and I was struck by his business model. At Happiness Ventures, Ajay aims to invest in happy entrepreneurs, as he believes that they have historically been the most successful. Five years into early-stage investing at Edelweiss, I reflected on what I have learned and found that Ajay really crystallized an idea that had been a foundation of my investing to date. I share Ajay’s basic philosophy, but rather than happiness, I have decided to call it optimism.  

I never really believed dramatic stories of companies on their last legs saved by a miracle from the founder.  But this scenario can happen! I can think of two situations where companies were literally weeks away from death and somehow a founder has pulled a rabbit out of a hat and sold the business for great outcomes.

I do believe the best companies are started by people that have a generally optimistic outlook. As a mentor of mine constantly reminds me, quoting Ben Horowitz from his book The Hard Thing About Hard Things, “There is always a move.”

Obviously, it is insanely hard to start a business, and most companies do fail.  Of course you aren’t going to be always be cheerful, but I think it takes a belief that there is always a move even when there may not be.