entreprenuers in transition

“Mr. CEO is what my title say”
Rich Homie Quan, “Type of Way

There’s plenty of advice out there for budding entrepreneurs but not enough for experienced entrepreneurs in a career transition. This is a revelation I had recently while lunching at The Battery with a good friend, a successful software startup CEO who needed guidance on his next career move. Below is my advice to him and those of you in a similar predicament.

  • If your goal is to maximize wealth, join a company in the $10M-$30M revenue range that is scheduled to go public within a one to two-year timeframe. Companies at this stage need CEOs who have experience going public.
  • I call this one the “angry god risk:” don’t join a company with a solution that is at the whim of big companies like Google, Apple, and Facebook. If and when these behemoths decide to own a certain sector, startups in that sector tend to fold.
  • Don’t join a company just because of its amazing technology. If there is no market for that amazing technology, the company should probably not be in business.
  • If you’ve taken a company public and have a track record of success — you’ve got a lot of career options that range from low-risk, high-returns to high-risk, high-returns. It’s probably not a great career choice to go into the business of changing the world, which is a high-risk/high-return endeavor. Don’t get me wrong: changing the world is a noble pursuit that is part of the foundation of Silicon Valley. But given that you’re in the prime of your career and have plenty of options, why not pursue the low-risk/high-return ones?

Need more advice on your entrepreneur-in-transition predicament? Ask away.