1. What person in the business or technology world do you admire most? 

Elon Musk, Steve Jobs and Walt Disney all come to mind for me. What I appreciate about all three of them is that they had a vision for, and then accomplished, things that the average person would tell you are stupid, crazy, or just not possible.

2. Which companies do you admire? 

The companies I admire mostly align with the people, but that’s not the reason I admire them. I admire companies that have established a notable brand - Disney Apple, Whole Foods, Tesla. I look at company brands as falling into three different categories - I want, I need, and I am. The “I am” brands encompass “want and need” but also define their consumers “I am a person that has an Apple Watch, drives a Tesla, shops at Whole Foods.” Nike also dips in and out of the “I am” brand category. 

3. What was your first job? 

The first real job that I ever had was working at an ice rink. I would pass out skate rentals, and then I’d get to go out on the ice and make sure that no one was skating too fast or causing trouble. At the same time I also interned for President Reagan after he was out of office. 

4. Which area of technology excites you most?

I’m most excited about space travel. The way I think of the universe is the way our ancestors thought of the world. Where people were populated in small portions of the earth, but then journeyed all over and discovered new parts of the world. The population would grow, then they would move to new areas of the world that were less populated. At some point the same will happen with humans moving to new planets. I won’t see much of this, but maybe my great-great-grandchildren will be the first generation of Martians - humans, but born on Mars. I would be thrilled to be part of any type of space travel initiative.

5. Is business school necessary for entrepreneurs?

It couldn’t hurt, but I didn't go to business school. I didn’t go to graduate school either. In fact, I don’t even have a business degree, but a philosophy degree. Sometimes I do wish I’d studied business and knew all the things a traditional business graduate knows, but at the same time there are many other things I do know that people with business degrees don’t. It can be a double-edged sword.

6. What is the best advice you ever received? 

The best piece of advice I received is that every leader should be fearless, flexible, and fun. I got that from Mahan Khalsa. One day he was meditating on his ranch in Hawaii and started thinking about what it was that made his businesses successful. The business ideas were good, but not revolutionary. In the end, what he realized is that all of the successful businesses embodied elements of fearlessness, flexibility, and fun, and decided that those three traits are what every person and business need to be successful. 

While I aim to work with these traits all the time, the one that really resonates with me is ‘fearless.’ I’ve always had a lot of ideas, which has led people to tell me that I’m “crazy” - I’ve been told this a thousand times. To me, this is just code for “You’re scaring me with your belief that your idea is possible. Most people live in fear and are afraid to accomplish what they are capable of and play it safe. Playing it safe is comfortable, but nothing great was done by playing it safe.

7. What advice would you give to someone who wants to do what you do?

First, when people tell you “you can’t do it”, you have to ignore them. And, if you’re hoping to always be in a safe, comfortable position, this - starting a business, being an entrepreneur - is not for you. The reason why is because you are always going to be having to step out of your comfort zone to do it.

Then, to learn and remember the three “F’s” to be fearless, flexible and fun. Things are always going to be changing and these three traits will get you through it. Silicon Valley calls changes like this a “pivot.” 

It’s really kind of like surfing. You're always balancing, and you have to ride the wave and move with the wave. If you fight the wave, the wave is going to win every time. I’ve found surfing to be really similar to building a company. You have to start by paddling out past the waves and it’s hard work to do this. Once you get out past them and you sit there - for a minute you get to breathe and it’s peaceful and delightful. But then you have to ride the waves. You are going to miss some, but you have to go after several. You will get some that aren’t the right one, but then even when you get the perfect wave, you have to work with it and not fight it. It really is so similar to starting and building a company. 

8. What’s the next big project you want to tackle?

Insurance for Space.

9. What do you do for fun? 

I have seven kids, and there is nothing I enjoy more than watching them participate in activities that they are passionate about. I have three sons that play ice hockey, one daughter that plays soccer, and another daughter that runs cross country. Some of the kids are involved in mock trial, and another builds robots and enters them in competitions. 

10. What challenges are facing the insurance industry right now?

I feel like technology is going to drive a major evolution in insurance, and that people are just starting to grapple with it. This major evolution is going to start when things are connected - cars, homes, buildings, people - and you can pull data on any of them at any given moment. When this happens one can understand the risk profile and if it’s going to have a loss or a problem - this will happen in real-time and insurers will be able to make very accurate predictions more quickly than ever before. This will completely change the way that insurance is done, and I’m not sure that anyone is really ready for it.

The way insurance works today is that you insure a thing or a person, or some expensive item that you own.

In order to insure these things, you have to pool your money with other people to create the protection. Then the insurance firms look at long periods of data - 10 to 25 years sometimes, to decide who the bigger risks are. Based on everyone’s risk, they determine pricing. For example this basic data has helped underwriters decide that a 25 year old male is a bigger driving risk than a 35 year old female, so they will charge him more. With buildings - if it’s 5 years old it won’t have as many problems as it will if it’s 50 years old. But, add sensors to that building and make it completely connected, you could even pinpoint minor leaks the minute they start and prevent them from becoming big, expensive problems. 

Even with people. The Apple Watch now includes an electrocardiogram ECG - when a person becomes completely connected, life insurance can be based on weight, ECG, exercise, and more in near-real time.