The Private Entrepreneur

An advisor to several startups recently told me most founders he meets are unconfident in private. The more founders I meet, the more I find this to be true. There’s a big difference between a founder selling their idea on stage and how they carry themselves daily. While founders are alike in that they are completely confident in their product, the details are not so simple, and they question themselves constantly.

The reason for this disparity is simple: founders need to project 100% confidence as they woo investors, employees and customers. The side effect of this disparity is that many founders go through tough times in isolation. They don’t realize others go through the same challenges, and so they hesitate to bring them up. And it takes time to realize when you raise a concern with another founder in private, a wall is torn down and they usually say they went through the same thing (or something like it).

We’re all aware that there’s a bias towards success stories in the startup world. I started blogging a year ago when I left Microsoft to capture both the ups and downs of my journey. But I don’t write about the downs, in part because I’m waiting to see how my story ends, but also because I don’t want to do anything to take away from my total confidence in what I’m doing overall. I expect to see stories from founders with successful exits the most, but at that point they seem to either forget the challenges, not want to relive them, or be too distracted by their yacht.

Until there’s more coverage of startup challenges, we can at least seek to be more candid in our private conversations. The right network is critical to your success, but you also need to be upfront about what’s keeping you up at night and ask for help. Don’t suffer alone. I’m currently enrolled in a python class at the University of Washington. The first course was an introduction to Python by following a textbook. The second course is internet programming, and suddenly there’s no textbook. After a few late nights trying to figure things out on my own, I learned how important it is to ask for help from classmates. Going from a large company to a startup is similar – there’s no textbook, and you can save yourself a lot of trouble by simply raising your hand.

 

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