After my dad died, I ran and sold his company (and I was completely clueless)

Over time, I realized that the problem wasn’t Gumroad, the problem was me. I was still so focused on that elusive unicorn, I couldn’t see the thriving business humming along right in front of me. Gumroad was profitable, the right size for its market, and enabling more and more writers, coders, crafters, and other makers to achieve their dreams with... See more

In college, the author started his first startup, and it failed. Before launch, he didn't talk to customers, he fought with his cofounders a lot. He didn't know how to build working software or deal with tech debt. He read Eric Ries's Lean Startup after this experience and vowed to use it. Since the insurance CRM was geared toward tracking existing... See more

One of the things that's really hard in a larger company is sharing and repeating stories. This is less about the company’s founding and such, but rather “What is our strategy? What are we trying to achieve? What are we doing?” Though people can look up our OKRs, it's not quite the same. If someone new starts tomorrow, they're going to get directed... See more