This article, by Gumroad founder Sahil Lavingia, should be studied with an open mind by anyone aspiring to scale a startup.
I thought Gumroad would become a billion-dollar company, with hundreds of employees. It would IPO, and I would work on it until I died. Something like that. Needless to say, that didn’t happen.
Now, it may look like I am in an enviable position, running a profitable, growing, low-maintenance software business serving adoring customers. But for years, I considered myself a failure. At my lowest point, I had to lay off 75 percent of my company, including many of my best friends. I had failed.
Fear is a powerful motivator, and for many of us, fear of not reaching your goals can be outright depressing. It’s so easy to get lost in the ambition of building something so outrageously successful that you overlook the pleasures of what you’ve already created.
While Sahil learned a lot about how to run a business (and how not to) through this journey, I believe his most impactful change was in his own perspective of himself.
I think we’re all guilty of putting too much pressure on ourselves to be something. And while ambition is necessary, decisions should be made with present reality clearly in focus.
Now is the only part of life that matters. Don’t lose sight of how to add the highest value today because you are sweating what the future may hold. It’s easy to lose everything that way.