I’ve started five companies, four of which failed miserably, one which did fairly well. I was also one of the first five employees of a startup which did quite well.
I learned a few things from the failures, some from the successes:
Three Bad Reasons to Start a High-Growth Startup
It’s easy to imagine that starting a startup will lead to a life of kicking back and chasing rainbows while the company runs itself. In reality, you'll have the flexibility to choose which 23 hours you want to spend each day agonizing over and attempting to execute the numerous facets of the venture. You might encounter a unicorn, but it will be dancing across your desk when you start hallucinating from sleep deprivation (think of this as the 400-hour-work-week).
2. FAME AND FORTUNE
The dream of overnight success—the “quick flip”—has tremendous allure. The thought of becoming a founder once set me daydreaming of ringing the opening bell at the New York Stock Exchange or getting a call from an editor at WIRED requesting an interview.
But big dreams quickly give way to relentless daily demands. I found myself drowning in the challenges of finding and motivating the right people, along with the endless array of tweaks and pivots inherent in developing a product. If your sole motivation is the faint possibility of “making it big,” you will run out of steam way before your enterprise hits its first rollout.