The Pioneer’s Dilemma

To leave the chasm behind, to cross it and not fall back into it, involves a transformation in the enterprise that few individuals can span. It is the move from being pioneers to becoming settlers. — Geoffrey Moore

I’m a startup junkie. I’ve learned to appreciate uncertainty and thrive in disarray, figuring things out without being hindered by bureaucracy. However, once the startup crosses the chasm and settles into something that resembles an enterprise-level company, I get cold feet.

These days, the word disruptive is usually depicted as something good.… Continue reading →

Don’t Work For A Startup

Two years ago, I was unemployed, delusional, drowning in debt, and drunk every single night in front of the computer after days and days of endless coding (and, well, drinking). I was trying to build something visionary, something that would catapult me into stardom, something that would let me cash in millions. None of these things happened. As Daniel Kahneman discussed in Thinking, Fast and Slow, it was a clear case of affective forecasting.

Fast forward two years, here I am, mulling over the remaining days I have left in what seemed to be a roller coaster ride of endless, rigorous days of scaling up, never ending ad-hoc tasks, and ever-switching job descriptions.… Continue reading →