While working for an Internet startup, our founder, CEO, and perhaps most importantly, boss, was a dynamic, unusual personality whom I’ll call Steve. Entreprenurial Steve.
A bundle of contradictions, in some ways I felt perfectly aligned, and in other ways, his thinking was so foreign to me that I couldn’t make heads nor tails of it. In all the time we worked together, for example, Steve never let anybody else pick up the check for a meal, and he was generous about inviting us out. During a period where nobody in the company had any money and we were essentially working for free, Steve didn’t hesitate to take us to lunch every day, and often out to dinner.
Steve had (at least) two BMW’s, which seemed like kind of a status thing, except that Steve wouldn’t hesitate to loan them to whoever needed them. Our secretary borrowed one and managed to total it in the parking garage (yes, I’m still unclear on how this can be accomplished) and Steve simply shrugged it off, saying, “It’s only a thing. The important thing is if you’re okay.”
Yet, when I stopped on the street to hand some cash to a homeless person with a sign, Steve was completely baffled. “Why would you give your money to that guy? He’s not doing anything for you.”
“Five dollars means a lot more to him than it does to me,” I tried to explain. “He needs it more than I do.”
“That’s crazy,” said Steve, shaking his head. “I’m sure you can do something better with that five dollars.” Weirdly, he handed me a five. “Here,” he said. “Don’t give this away.”
At times, it seemed that Steve held the company together through sheer force of will, when paychecks were bouncing and vendors weren’t being paid, his optimism and willingness to do anything to get it done for our customers was infectious, truly believing that our next sale would put us on firmer financial footing (which it always did, for a while) and that stability and prosperity was within our grasp.
Steve always seemed to know who to pay. Starting, I suppose, with the lawyers. “Get the most expensive lawyers you can,” Steve once explained to me. “Even if you have to skimp on everything else.”
Our lights were always on. Our Internet connection always worked. Our phones always worked. Other than that, I’m not sure anybody was paid at all.
Occasionally, a process server would come by, and Steve would invariably be gone. Otherwise, he always seemed to be around, and I have no idea how he managed it.
Although clearly uncomfortable with kids, my precocious daughter asked him if she could use a computer. Without hesitation, Steve handed her his personal laptop, explaining that he was going to a meeting and wouldn’t need it until the next day. She dutifully returned it to his desk before we left.
The next day, we had a meeting with a potential customer. Our presentations and servers were all online, so there was little prep necessary except for connecting to the Internet. Steve booted his laptop, and instead of the familiar Windows chime, the room was treated to:
“Uh ohhhh!” from the Teletubbies.
A number of people in the room clearly had kids. Steve was thrown off kilter, but shook off his utter mortification and made an excellent presentation. (We got the deal, and I suspect the unexpected presence of the Teletubbies made us seem more human than slick and polished.)
A week later, my daughter asked to borrow Steve’s laptop. Without hesitating, he handed it to her, but paused before letting it go. “Try not to leave anything in the drive this time.”