I’ve always wanted to make a lot of money, have people pay a lot of attention to me and do a lot of exciting things. I just never knew how.
Many of my friends who are founders of their own companies tell me how they exhibited the entrepreneurial spirit as a kid — they sold candy out of their backpacks, had a landscaping business during the summer, etc. They
created value and learned the virtues of hard work early on.
But that wasn’t me. I created a horse-racing simulation game in Applesoft BASIC in Manhattan Beach Middle School’s computer classroom and ran a small gambling operation. I mean, who could blame me? The teachers left that class completely unattended during recess and lunch, as if they couldn’t fathom how any kid could get into trouble playing with those large calculating typewriters.
However, making a few dollars to buy an endless stream of Atari games and learning how to collect from the bigger 8th graders didn’t teach me anything about building a tech
company. By the time I decided to move to San Francisco, I was completely and totally clueless.
Just as bad was my sense of timing. By the time I entered the job market the dot-com bubble had burst, leaving scores of smart people unemployed and a wave of VC firms bust. A lot of people were leaving the Bay Area to go back to wherever they had come from, but I was too stupid to know anything about the logical decisions people made.

The discount brokerage firm where I clerked gave us all two weeks of training in how to execute online stock trades at one of their call centers in San Diego. That’s when I had my brilliant idea (except it didn’t turn out to be brilliant until I changed it a few times).
The call center manager who monitored our training was in his late twenties and had a smug grin on his face all day, every day. “This call center system I’m teaching you costs $30,000 a person,” he mentioned, several times. He smirked a lot and I despised him.
It struck me that if I could build cheaper call center software, I could make my own software company — and have revenge on The Smirker.
The stars must have been aligning for me because shortly thereafter, my college roommate, who I nicknamed “The Fro” (I give nicknames to everyone for whom I have a deep affection), called to tell me (brag) that the call center software startup he worked for had been acquired by Cisco.
He hadn’t made much as a late-stage employee, he admitted, but he had a taste for what could be, and encouraged me to fly to Boston to discuss creating our own startup. “After all,” he said, “you’re good at selling shit.”
I wasn’t sure that was a compliment, but I bought the plane ticket.

After a weekend of discussing dreams and man-feelings, we got each other excited enough to decide to quit our jobs the following Monday. I gave my two weeks notice.
Then something odd happened. The Fro wouldn’t answer my calls all day that Monday. On Wednesday he finally called me and said sheepishly, “Brooo. You know what Bro? I decided that it’s not a good idea for me to quit my job right now. Seriously. I’m so sorry.”
I had $5,000 in my bank account, and I seriously thought of spending $1,000 of it just to fly back to Boston to punch him in the face. Instead, I hung up the phone and punched the wall. Maybe a few times.
Then I called him back and asked him, as calmly as I could, if he knew of anyone else at his newly acquired startup that might want to create a software company with me. I reminded him that I was good at selling shit. He introduced me to “Tooter,” who, it turned out, was heading my way to go snowboarding in Tahoe.
When we met at Heavenly Ski Resort I discovered an obviously brilliant guy who disliked corporate life and had an unbridled affection for activities that may not have been fully legal in the state of California. But hey, we all had issues.
He explained to me that he and The Fro had worked at a startup that created software for call centers, an ages-old industry they had revolutionized by adding a .com to the name of the company.
Because I was an entrepreneur (unemployed) now, I told him that we should just recreate that class of software, and he agreed. To his credit, and somewhat to my amazement, he sent an email to his boss and quit that night. A few weeks later he sold his house in Boston and bought a new one in the Bay Area.
But what made him such a risk taker and brilliant programmer also made him a supreme asshole at times. Knowing nothing about software companies, many of my questions were met with a question of his own, his favorite being, “Are you a fucking idiot?”
There were so many depressing nights alone that often I would watch my favorite movie, The Shawshank Redemption, over and over, mindlessly. Maybe seeing Andy Dufresne enduring so much shit made me feel better about my own situation.