"There are two key leadership skills that everyone needs to learn: triage and iteration. You spend every single day prioritizing your time. As Steve Jobs used to say, 'It’s what you say no to that’s most important.' Sometimes you need a competent tyrant rather than a committee."

Fast Facts

Location Chicago, IL
First job Magician at the age of 10 for neighborhood children’s parties
Most admired leaders Jeff Bezos of Amazon, Steve Jobs of Apple, Steve Case of AOL, former President Bill Clinton

Questions & Answers

How did your early life inform your leadership development?

When I was 10 years old, I was a magician at children’s parties. The job was not about doing the magic or handling the kids. It was about managing the parents, because they all wanted to stand behind me and see how the trick was done. Dealing with adults at that early age was a confidence builder for me. My parents were also a very big influence. They were the most unconditionally loving parents you could imagine. But my mother and father were also very demanding—they wanted their kids to excel.

Tell us about the best leadership advice you've received.

When I was a trial lawyer, I interviewed with the most successful lawyer in the country at that time. I decided not to work for him, but he shared something interesting with me. He said that life is generally divided into three buckets: work, recreation, and family. He said that if you enjoy and love your work, if you are doing things that are important not only to you but to other people that you are creating jobs and futures for, then you can focus on work and family. Your recreation is already covered in your work.

A corollary to that observation is that you’ll always have more work but you only have one family. Your work is what you do but it’s not who you are. It’s very easy for an entrepreneur to get completely consumed with the idea that the business is everything. Startups have a lot of hills and valleys. Having family as a solid base makes it easier to take risks in other areas of your life.

Describe your leadership style.

I want people to learn and get better. I believe in modeling the behavior that we expect of our people and our companies. Talent and creativity are great but ultimately what trumps both of those is pure hard work.

There are two key leadership skills that everyone needs to learn: triage and iteration. You spend every single day prioritizing your time. As Steve Jobs used to say, “It’s what you say no to that’s most important.” Sometimes you need a competent tyrant rather than a committee. I think that the truth only hurts when it ought to. Good leaders are strong editors.

What advice would you offer to emerging leaders?

A startup is very much akin to a family in a lot of ways. You must make room for all kinds of people. Entrepreneurs often fail because they think they’re going to hire people just like them to build a business. You have to make room for different personalities, talents, and interests. After work, some people want to just go home, some people want to go out together and have a beer, and some people are halfway in-between. You can’t have effective innovation without inclusion.

What leadership skills are essential in shepherding organizations through significant transitions?

The co-working space isn’t merely real estate, and I think a lot of places that come to see us and try to steal the secret sauce don’t understand that. Our structure creates an opportunity for everybody to smash into each other all the time. When you’re building an ecosystem, these collisions make 1871 successful. People get the definite feeling that they’re not alone; there’s a lot of lateral learning happening in our space. Part one is to give people the tools and the resources they need to increase their likelihood of success. Part two is to only let the right people in. If you pick your inputs right, you are more likely to have successful outputs.

Interviewed by Jennifer Miller and Bria Smith.