In my startup investing, inside portfolio companies at the highest leadership and board levels, I always want to make sure that a pessimist has a seat at the table. I want a table full of optimists, but I also want at least one respected pessimist sitting there. That pessimist should carry a general lack of confidence in humans to behave logically or ethically. They should also have seen many shit-shows in their lives. You don’t want someone who is just irrationally afraid that the sky is falling, but you do want someone always thinking about the downside case.
As it turns out, often that pessimist is the CFO or the General Counsel. These tend to work well as long as they are respected and have a voice. Without a pessimist in the room, with a seat at the table where the big discussions happen, there is no balance.
The optimists provide the energy and create the gains, and the pessimist ensures we consider our risks and can help us avoid disaster.
If your startup builds a room full of pessimists and you have one optimist at the table, then I think you’re in the wrong business. But the other way around is invaluable and necessary.
Do you have a pessimist in the room where it happens?