As an early stage company founder and CEO, I am obsessed with money management. Meaning - I have the perpetual sense that we’re about to run out of it. Sometimes we are, sometimes we’re not, but it definitely keeps my paranoid mind alert (at night). I think that bootstrapping (which is what we’ve done) has a very profound effect on the culture of a company. It creates a mind-set of “essentiality”, not excess. It creates a mind-set of how much we can get done on how little. It’s a mind set of really appreciating reward when it comes. And I think from a pure business perspective, it creates a mind-set of operational efficiency that results in higher margins. I wonder what percentage of web 1.0 companies that made it through the long winter were bootstrapped companies.

Originally published on WordPress on September 25, 2007. Migrated to this blog on May 29, 2025.