I’ve had the thrill of a combination of successful and less-than-successful startup experiences. The first ended in a 9/11 accelerated total collapse in 2001. The 30 seconds on it are “we had a little piece of software that got downloaded about 25,000 times, and if you were on, let’s say Amazon, looking at the latest Harry Potter book or Palm Pilot, we popped open a little window and offered to show you the price of that product on fifty other websites”.
It was called Clickthebutton.
Our CEO/Founder eventually had a little bit of a “mental break” and decamped from NYC to Santa Monica, and so the day-to-day fell to me and great friend Luke Gebb. Unfortunately, I didn’t know what it meant to be a startup CEO at the time, so lots of decisions were delayed and actions not taken.
When I talk about past startup shutdowns, the first question is almost inevitably “what did you learn?”, and Clickthebutton had a wonderful list of powerful lessons. The top being how people understand and accept the difference between “risk” and “uncertainty”.
In the final six months of Clickthebutton it was clear that the right wind could fill our sails, or a medium sized meteor could destroy us. The team knew things weren’t great, but they didn’t have a real sense of “how good or how bad” it was at any given moment. So I started adding a moment to the beginning of our Thursday team meetings where I wrote a big number on the board between 1-4. One meant we were getting close to being bought for a giant truck load of money, 2 meant we were getting close to being bought for $1, 3 meant we were hustling and keeping our head above water, and 4 meant it was time to plan the closing party.
Not one person left Clickthebutton in that last six month block, and it slowly washed over me that people can handle “there is a one in three chance you’ll be killed” (risk) much better than they can handle “a rock could fall out of the sky and hit you any time” (uncertainty). To boost risk tolerance, we opened a second bank account, and if you made <$30K we put two paychecks with your name on it in the account and if you made more, we put just one. Nobody quit.
I’m not totally down with the 100% transparency theory of management, but I understand some parts of the dynamic around risk vs. uncertainty. Those were knowledge-packed days.