It was a beautiful feeling.

We had just raised our first after-seed round of investment, bumping my salary as cofounder and CTO from a voluntary $24k a year to a healthy six figures, while simultaneously driving up the value of my stock equity. The rest of the team, my comrades in arms, were similarly bumped and positively impacted.

Flash back to around 2011 at my previous company.

We had a great team, a solid product, and even some paying users. We’d all been slaving away at sub-market wages for quite some time, putting in sweat equity to build something real. To reward ourselves for our wisdom and hard work, we went on a well-deserved shopping spree at the Apple store and bought ourselves the latest Macbook Pros, with bells and whistles.

I would have thought you insane if you suggested to me, back in that day, that we were at the top of a rollercoaster. And yet approximately two years later, we were at the bottom, broke, with no real shot at getting back up. What the hell happened?

Continue reading