Don’t overestimate the downside of risk — Medium

He’s been at it for three years, and he’s wondering — like many of the founders I meet with — what it will be like if he raises money.

“Will I have a board?” he asked.

“How often will we meet? What will their expectations be?” he quickly followed.

“How will things change?”

I thought for a minute before answering — something I’ve added to my Jedi skill set later in life — and told him “It will change.”

He looked at me and I realized he wanted the details. Was he ready for it, I wondered. Yes, he’s ready for it.

“You are going to have to learn to take bigger risks and get comfortable with failing more. You got one of those kids who has worked for you since the beginning, who has been super loyal and does anything you ask him to?”

“Yeah actually, we do” he replied.

“Well, you’re going to take the three jobs he’s doing poorly and hire three people to do them right — and there is a 50–50 chance there won’t be a place for him when you do.” I told him candidly.

“Hmmm… “ he replied. I could see it sinking in — things change.

“And you’re going to have to take $500,000 and come up with 10 really good ideas to try, knowing that eight of them are gonna fail. You’re gonna burn $400,000 big ones in a pile of ash — so that one or two ideas might transform the business. Those ideas will take you from $1m this year to $3m the next year — and $10m the year after. How many $50,000 crazy bets have you made in the last three years?” I asked.


Of course, you can’t make crazy bets when you haven’t learned to turn off your fear. Just like Luke needed to face Vader in the cave trial and then in person, founders must face their fears … without feeling fear.

It takes time, and there is no silver bullet, but as my pal E told me once, “people overestimate the downside of risk, Jason.”

via Don’t overestimate the downside of risk — Medium.