The more I interact with entrepreneurs, and the more I try to learn, the more the recurring dark cloud of what cognitive scientists call the knowledge illusion comes to haunt me. This is the idea that we get convinced our opinions are fact, and once we accumulate a bit of knowledge on a subject, we start feeling like experts. Don’t get me wrong, I truly believe there are true experts in every field. And I also tend to subscribe to the notion some adhere to that states that to become an expert at something you need to devote 10,000 hours to it. That amounts to a bit over 19 years, if you devoted 10 hours a week to the subject at hand. Going full time at it, it would take you about five years.

Last week I stumbled upon a friend entrepreneur who I can recall I last saw maybe 2 or 3 years ago. By most accounts, he would be categorized as successful. As he recounted the story of his life up to now, after a 9 month stint in a tech Fortune 100 company over 15 years ago, he has built a number of businesses, all in the SaaS space, and even when he has not had what he would call a home run, he has been able to call his own shots, and although with ups and downs, has been able to provide well for his family.

I first heard of him some 8 years ago, when he won one of the few if not the only business plan competition that existed in South Florida – the most high profile, at least – and I saw his picture and read his story in the paper. It caught my attention back then because we had similar backgrounds & upbringing. Not many months later, I ended up in a meeting with him as he had presented a software development proposal for a weather media company I co-founded. We did not engage in the contract, but since then, we have stayed in touch and continue to “stumble upon” each other every so often.

When I last had seen him, it was to seek his advice as an expert in a certain online traffic monetization strategy my partner in another startup and I wanted to pick his brain on. We listened intently, I absolutely considered him an expert at what we were meeting him for – and still do – and we did well to follow his advice. In my view, he is an expert in a number of areas, and I value highly his friendship and openness to share his knowledge. He has devoted the last 15 or so years testing, building, pivoting, and rebuilding a number of business models with a single focus on scalability. He has worked with the same technology partner entrepreneur for all those years. He is a digital marketing expert. He has tried it all, he has experienced it all. Constancy, and focus on experimentation and validation have been the hallmark of his entrepreneurial life.

As I mentioned in the beginning, I stumbled upon him last week. We had a great conversation. He had arrived at the event via Uber, and I even gave him a ride home, as we live within 2 miles of each other. I was shocked when he told me that after all his experience as an entrepreneur, he had come to the conclusion that the one element that separates the big winners from the also ran is plain luck. I could not believe what I was hearing.

I firmly believe that you make your own luck. I also know some of the big winners. They are insanely focused on their business, but at some point they need to engage in the contact sport that entrepreneurship is all about to really be able to turn a validated scalable model into a home run winner by attracting the outside fuel and additional resources to make it happen. I have written about this in the past. The hard part is trying to maintain the focus that makes them experts in their field, while at the same time building and nurturing a network of contacts that turn your and your network’s skill set into the equivalent of a Swiss Army knife at your disposal. Sometimes you need other people to help you.

I told my friend that he is wrong to believe that between his current batting average and a homerun only luck stands in the way. His company is profitable, is a sole player in a niche that he could disrupt and grossed in the multiple hundred thousand dollars last year. After more prodding and questioning, I reached the conclusion that he has been obsessively holed up in the latest iteration of his startup for too long, and I made a commitment to myself to put him in front of mentors and funders that I have seen take on, in the past, less compelling projects.

I will make some introductions for him. After learning more and more about him over the years I have come to see him as the kind of entrepreneur for which I am willing to put my hand on the burner. There is only one thing I want out of this. I don’t want to be the guy who “breaks the spell” on his luck, as he perceives it. He has devoted more than the 10,000 required hours to become a true expert in his line of work. I truly hope I am not under the cloud of knowledge illusion, but I want to bring him into the fold of those of us who firmly believe that you make your own luck. Of those who, instead of a horseshoe, hang a wrench on their door frame.

Our View from the Top – May 8, 2018