I usually temper the amount of alcohol I consume when in a professional setting because when under the influence I tend to lose the split second of judgment that determines when a question is appropriate or not. On this occasion (this was while still with my previous employer), however, with a belly full of red wine and steak while in the presence of a young and well known internet entrepreneur, I decided to let myself go.
“So tell me the truth: we’re almost the same age. You’re running a multi-million dollar company. You have dozens of employees. You get over 30 million uniques a month. How the hell can you be so sure you’re not going to mess it up? Do you think about that much?”
He smiled as if I asked him how much he was worth and he was delighted to finally be able to let it out:
“Of course I do, I think about it all the time, especially after turning down potential buy-outs. There are two things that keep me confident: the first is that I have done every job in my company. Over the course of building the business I have at one time or another done everything we in fact do, including things I know nothing about like accounting.”
“Second,” he took another sip, “I only hire people who are smarter than me. Everyone around me is brilliant and I pay above the market in order to be able to make smart and educated decisions.”
There had always been something that attracted me to this particular entrepreneur: part of it was our shared sense of humour, and part of it was how he chose to engage with me and my colleagues.
Our work relationship was a strange one that saw us as both partners and adversaries: on the one hand we were a vendor, and many companies love to remind vendors how replaceable they are. On the other hand we were also a source of revenue as well as the primary provider of his advertising infrastructure. For the purposes of good service he would want to stay on good terms, but I never got the sense that such an idea fueled his motivation. Indeed, whereas many CEOs simply delegate the task of remembering names to underlings, this CEO was generous with his memory, his time, and his attention.
Our conversation revealed something else about him though that I hadn’t been able to pinpoint, only sense. That missing ingredient was his humility. Despite his status as a minor internet celebrity he never drank his own Kool-Aid, never paid any attention to the hyperbole attached to his achievements, and most importantly never began to believe that his success was directly correlated to and a result of his talent and only his talent.
His success, he acknowledged, was to achieve a minimum amount of traction on his own and to have the vision of where he needed to take the company to endure over the long term. Then, once exponential growth kicked in and he couldn’t close his eyes without seeing the faint glow of hockey stick graphs on the back of his eyelids, he immediately began to build a team that could manage the growth and keep him on the right course.At no point did he think “I can do this on my own,” nor did he let his ego get in the way of hiring people whose brilliance might otherwise intimidate an insecure leader desperate to demonstrate his/her control.
Instead, he realized that his success would be determined not by the generosity of the gods who filled him to the brim with talent, rather by the quality of the team he could build and the people he could surround himself with.
Today though he continues to be the public face of the company, together he and his team push the business forward. Keenly aware that the internet economy can change direction like a prairie wind, he builds as if in a race against the impending winter. He’s never satisfied with what he’s achieved and spends most of his time focused on the horizon as opposed to admiring his trophy cabinet.
Appearances can be deceiving, especially when our cultural preference for singular narratives blocks out collective efforts in order to focus on the greatness of individuals. In my experience, however, the most successful and brilliant entrepreneurs are reluctant to believe they are in fact successful and brilliant entrepreneurs. Instead, they build teams and they infuse their companies with cultures in which employees feel a strong sense of mutual loyalty and dedication. Furthermore great entrepreneurs are able to identify that point in time where the organization they have created has become bigger than them. Unlike the wife of Lot, they don’t allow themselves to look back and stare: instead, at that critical moment they relax control, focus on finding talented people they can work with and trust, keep their head down and eyes forward. Only then can they begin the process of building something whose creative potential is greater than the sum provided by founder.