My mind has been rattling around these two posts for months. It came to the forefront again after this tweet from my friend Tiffany Zhong. I have some thoughts. But before I dig into that, let me set the base. My first startup was at the age of 18. I'm…

This post was written for and originally appeared on 99u, which you can view here. Sounds funny, doesn't it? Ambition isn’t typically referred to as something that needs to be “dealt” with. On one hand, it’s the driving force behind every great accomplishment. On the other, it’s…

Life rarely moves in a straight line. It moves unforgivingly through peaks and valleys, highs and lows. Your career is no different. When I first started my career in technology, at a fairly young age, I had a pretty clear picture of what I wanted my career trajectory to look…

It was my first startup. I was 18 and we had just raised our first real financing round -- $250,000 from a local angel group. A lot was riding on us, even though the scale seems minuscule in hindsight. We had just upgraded from a basement to an actual…