When we talked, I thought he would be happy.
He struggled to understand why, among the scores of equally or more talented entrepreneurs who start businesses every day, his was successful. He struggled to understand why "it" -- fame, fortune, and tens of thousands of quasi-evangelistic customers -- happened for him, while people he knew and admired had failed.
In short, he struggled with "Why me?"
He also didn't think he deserved it. Like most successful people, he considers himself to be average in almost all things. (Persistence, determination, and effort are what allow "ordinary" people to accomplish extraordinary things.) He had worked really hard, but in his mind, everyone works really hard.
And, maybe worst of all, he didn't enjoy it. Sure, he had dreamed big. He had hoped for personal and financial success, and all the fulfillment and gratification and just plain fun that comes with it.
But it wasn't that fun. He worried about continued growth. He worried about the inevitable competition. He worried about his ability to lead a rapidly-expanding workforce. Success yielded a new and surprisingly much larger set of challenges.
Worst of all, he had thought success would change him. Sure, people treated him differently. But inside, he was the same guy, still struggling with the same doubts and insecurities and hang-ups.
I told him that was a good thing: He didn't want to be one of those people derailed by over-confidence and excessive self-belief. I told him "deserve" had nothing to do with it, because "deserve" never does: We earn our successes, just as we earn our failures.
And as for "Why me?" I told him he's too modest to accept, much less internalize, all the reasons I could list. He has complete and total belief in the usefulness and value of his products. He believes in what he has done. But he doesn't believe in himself.
While that sounds like a problem, it's not. As Ryan Holiday says, a lack of self-belief doesn't hold you back. Whether you think you can do something is less important than proving -- through effort and achievement -- that you can do it.
The proof lies in the result, and I told him the results answer "Why me?"
Even as I talked, though, I knew my words wouldn't help. Like most highly successful people, he gives luck much of the credit. Science backs him up: Research conducted in 2018 at Cornell University found that talent plays a role where achieving extraordinary financial success is concerned, but randomness also plays a prominent role.
He thinks he got lucky: right products, right time, right messaging, right economic environment...the stars aligned.
And maybe he's right. But he was there -- ready, willing, and, most importantly, able -- to spot and seize the opportunity.
That wasn't luck.
That was education, experience, connections, insight, effort, a willingness to take intelligent risks...all the things that make entrepreneurs entrepreneurs.
That's why him. That's why he deserves it.
And that's why it's fun -- not because of the money and nightlife and accolades but because he gets to enjoy, every day, what he hoped for most: to build a company customers would love, and people would love to work for.
All of which, especially if you sometimes question your abilities and "worthiness," is also true for you.