Two months ago, I left Airbnb to pursue entrepreneurship. I joined Y Combinator's batch on January 5th, 2021, and have been building Shepherd with my cofounder Justin.
Focus on Large Problems
I acknowledge rewriting the company's API from Rails to Node.js was a strategic misstep. While I view this as the correct long-term decision, the transition consumed significant time early on. Getting to a stage where I was being productive on the backend is still WIP. The tech stack change diverted my attention from core business problems, forcing me to rebuild expertise I'd already mastered in Rails, including error logging infrastructure.
Appreciate Your Cofounder
The intensity of cofounder relationships compared to regular employment is unique. Justin and I schedule weekly walking meetings to discuss concerns, celebrate wins, and build mutual understanding. This practice reinforces our partnership and ensures we actively appreciate each other throughout the demanding startup journey.
Writing
I'm committing to documenting my experiences through regular posts, including bite-sized technical solutions to problems I encounter. Writing serves dual purposes: knowledge sharing and visibility for recruiting and community engagement.
People Want to Help Nice People Doing Interesting Things
Leaving my established Airbnb position has paradoxically opened doors to influential investors and entrepreneurs. These connections materialized because of a respectful approach and compelling mission — opportunities previously unavailable despite an impressive corporate background.