My Reality Check Bounced! - Jason Ryan Dorsey [63]
True, Stephen’s start-ups never made a profit, but back then, whose did? It wasn’t about profitability; it was about IPOs and LBOs and MBOs. One night, Stephen was so excited about the launch of his newest company that he dyed his jet black hair bright blue. The color matched his new company’s bold strategy for reaching hip teenage girls.
In hindsight, Stephen should have seen the end coming when the blue hair arrived. He knew how to value businesses. He knew market cycles—in fact, that was his specialty. But the fast money and over-the-top lifestyle seduced his better judgment.
Reality struck when he saw once high-flying dot-com executives stop bragging about their stock options and start selling their office furniture. As CFO, Stephen knew that his current start-up’s expenses were eating through cash like a tapeworm. In years past, there had always been new investors with new money to save the day. Not this time.
The bubble was bursting. Those who had gotten out at the top were fabulously rich. Those still in the dot-com business, like Stephen, were trapped with worthless stock options and the walls caving in. With growing expenses and no new investor’s money to his rescue, Stephen saw the end coming. He felt as if he were trying to outrun a train while wearing sandals. Smack. It was over.
Within one year, every highly touted company that Stephen started or helped start collapsed in on itself. He took the loss of jobs, money, friendships, and perspective personally. He should have known better. How could he have been so naive?
He got so down on himself he was convinced even God hated him.
That’s what led Stephen back home. He thought spending a little time reconnecting with his family would help him get his head on straight. It didn’t. How could he relax on his parents’ couch watching TV shows about the rich and famous when just a year before he had been one of them? The depth of his fall plagued him. Every job on his résumé in the last five years was with a now-defunct company. He had just turned thirty years old and felt as if he were starting all over.
Making it worse, his previous business heroes were being paraded in handcuffs on the evening news or were themselves looking for jobs. He didn’t want to be one of them. He never again wanted to feel the pain and humiliation of failure. This fear gradually ate at Stephen’s independence and courage until he succumbed and accepted a safe eight to five j-o-b.
FROM DOT-COM MILLIONAIRE TO DILBERT
His new job was purchasing small companies and combining them together to be sold as one larger company. His position was highly paid, and he had a big title. He should have been thrilled, but he wasn’t. Every time he paid an entrepreneur wearing worn-out blue jeans eight figures to buy her business his inner entrepreneur burned. He wanted to be his own boss and once again control his destiny, but his fear of failure was just too great.
After six months as a well-paid but uninspired employee, Stephen began feeling extremely restless at work. This time, though, the stress was not from his fear of failure. The stress was coming from something much deeper: his identity.
Stephen was starting to see that his current job was in conflict with everything he believed in and stood for. Sure, his job was high paying, but it was forcing him to turn his back on what, deep down, he knew to be true about himself. Stephen was born to be an entrepreneur. It wasn’t about money or status—it was about being your own boss and creating something from the ground up. Pursuing anything else, even a high-paying job, was a compromise inherently destined to be unsatisfying.
It didn’t matter to Stephen if he owned a company with a thousand