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Yup. It is soul-crushing.

My company failed in the back-wash of the "dot-bomb" (we were not strictly a dot-com play - but close enough that we got caught in the back-wash), and while I would have preferred IPOing (not really possible in early 2000) or M&A (actually, similar reasons), I got really DEPRESSED!. Now, I was just the founder, not the CEO, but the journey from garage to supremacy (if you even make it) is a ride, maaan!

I always found the garage loneliness that you find people lamenting on HackerNews to be a lot more bearable than 10 shareholders and 250 employees and (in our case) 20 global enterprise customers. I am certainly not sure that I have it in me to attempt again. Psychologically, I mean.




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