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

Silicon Valley is the canonical example of economic agglomeration. The knowledge of how to build, program, and operate computer components was a shared, scarce resource in the early 1960’s. Programmers and technicians often moved between companies, transferring best practices. This collaboration caused companies to release products with complementa... See more

Profitability means sustainability. Instead of treading water until a lifeboat comes along to save you—which is how many founders think about raising their next round of VC funding—it means building your own boat.