What was it like to lay off the entire Gumroad team?
Sahil knew Gumroad was running out of oxygen and the layoff were coming. When the day came though, it felt wrong. It felt like watching The Lord of The Ring, hoping for the happy ending, except that Frodo got killed and Sauron go the ring. It did not make sense.
Even though he had a support network, and people knew what was going on, failure was an awkward topic and Sahil was pretty alone. Unable to share in person, Sahil wrote a larticle about his story, called Reflecting on My Failure to Build a Billion-Dollar Company.
Sahil was fully expecting to live alone in the mountains after that, but quite the opposite happened. People wanted to hear his story exactly because failures happens all the time in Silicon Valley, but no one talks about it. The post went viral!