Being Fearless with Jean Case

Jean Case, early AOL executive turned tech pioneer turned philanthropist, has a new book out called, Be Fearless. If you’ve never heard Jean speak, listen to her interview with Kara Swisher to get a feel for what she brings to the table. In her book, Case outlines five rules for enacting change, individually and at the enterprise level. These are all applicable to our own businesses.  

1. Take a big bet. We should use odds to approximate our confidence in any effort and the impact of the payoff. The greater our confidence in an outcome, the more willing we should be to dedicate resources to the bet. Whether it’s on people or processes, don’t bet too small. “This event has a 50% chance of attracting the type of people we’re trying to get in front of, so if we invite 20 and get 10, we’ll have really moved the needle.”

2. Take risk. Nothing outside of physics has perfect odds of happening. We have to be comfortable with being bold about the bets we know we should take. That also means we have to understand our own risk tolerance. “We’re willing to invite 20 people and only get 10. Even if we’re wrong and get 5, that’d still be a win.”

3. Make failure matter. Thinking in bets means we are constantly running experiments. Whenever we are proved wrong, it’s not a loss, but a lesson to be learned. “Well, we invited 20 people and only got 2. What could we have done to better attract our target? What can we do differently next time?” 

4. Reach beyond your bubble. We all need people who can see our blind spots, expand our perspectives, and aren’t afraid to tell us. We need to cultivate these types of relationships and seek out those with different approaches and perspectives. “I know someone who has done this with way better results than we’ve been getting – let me email them.”

5. Let urgency conquer fear. Don’t just think about stuff, do it. Action is favorable, even if it’s just taking the first step towards the second. No analysis paralysis – get at it. “We may not know the exact odds or even if this will totally work, but I think we can pull this off next month if we move now. We’re going to learn from it either way.”

As we think about how to grow and expand our minds and businesses, Case’s five rules make for excellent guiding principles. When we commit to forward progress and learning along the way, good things happen.


Leave a Reply

Your email address will not be published. Required fields are marked *