Five Questions For … Nick Kennedy, Founder of Dallas-Based Rise

Dallas — Texas is a far-flung state with metro-city populations that are about 200 miles away from each other. Because of that, tech innovation circles tend to largely stay amongst themselves, with the occasional meetup at South By Southwest Interactive in Austin.

As a way for people around the state to get to know each other a little better, I am kicking off a new feature called “Five Questions For … .” This story series aims to get a little more personal with Texas innovators, find out who and what motivates them, and talk about their struggles and inspirations.

For our first profile, I spoke with Nick Kennedy, founder and CEO of Rise, an aviation startup in Dallas that employs no pilots and owns no planes. “We’re a technology company,” Kennedy says.

After launching in 2015 with five employees and flights to and from Dallas, Houston, and Austin, Rise now has a 50-person staff and recently added service to San Antonio and a service to a second regional airport in Houston. Kennedy, who is 38, says the company’s mission is to leverage its software—which aims to match flight schedules based on demand—to help its road warrior members save time.

Here is an edited version of our conversation.

Xconomy: Tell me about your early influences.

Nick Kennedy: One of my main mentors who has since passed away was Calvin Howe, who was an entrepreneur; he owned a bunch of Hampton Inns and other businesses. One of the influences he had on my life was to establish early on principles on which you can live your life and build businesses on. He was talking about making decisions that at the time seemed hard, but in the long run, had really good consequences with regard to how you treat people and invest in employees.

He always talked about, you make a certain amount of money and then give everything away. I was fresh out of college and didn’t have two nickels to rub together. I had school debt and could barely make rent. I was not focused on decades down the road, just tomorrow.

For some reason, he took a liking to me. I reached out to him; I was a junior in college (at Harding University in Searcy, AR) and was at a place when I was trying to figure out what I was going to be when I was growing up. I reached out and said, Can you help?

The amazing thing about really great people … there are very few great people that you can’t call up and ask for advice and they won’t give it to you. If you give them a legitimate story, they will find time to help you.

X: Where do you think your drive comes from?

NK: I’m very curious by nature, and very focused on big picture things. I don’t want to do anything that’s been done before. I don’t know where that comes from other than I’m curious about why things haven’t been done a certain way.

I’m also a little bit annoyed by things that are broken. The best businesses in the world do one thing very well—they fix people’s problems. I hear this story over and over again amongst entrepreneurs, ‘I had a problem and I couldn’t get it fixed easily so I turned it into a business.’ Everybody gets annoyed. Entrepreneurs take that annoyance and say, How can I turn a business out of this. Annoyance is the greatest characteristic an entrepreneur can have because it makes you ask questions in a manner that leads to potential businesses.

I don’t come from money—I come from the opposite of money. I love the idea of coming from nothing and creating something, not only for myself but also for the 50 employees I have. That’s the greatest honor I can think of.

Entrepreneurs are eternal optimists. You have to be because there’s so many reasons why you shouldn’t do this.

X: What’s your biggest failure as an entrepreneur?

NK: I’ve got about 1,000 of them; which one do you want? One of the biggest lessons I’ve learned in the first company that I was involved in starting, and I’m speaking for myself. I wanted to build a company and sell it and makes lots of money, period. And we did, in a very quick time period. At the time, I was a king of the world in my own small mind.

Looking back now a decade removed from the situation, it was a very shallow experience for me. Inevitably, the money comes and goes. The older we get, money is less valuable. Time became more valuable. I spent years of my life giving everything I had towards [that company], and the company we sold it to ran it into the ground. And it doesn’t exist anymore. I gave up several years of my life doing that, and we didn’t create anything that was long-term.

I would argue it was because I wanted to make a lot of money, because I didn’t have any money and I thought that was what I wanted to do. Don’t ever do it for the money. It sounds so trite, but do what you love and the money will follow. It doesn’t mean money will flow … But know why you’re doing it, have a passion, and make sure you make money to stay in business.

By focusing on a quick exit, and focusing on money, we had an opportunity to do something great, and we didn’t.

X: You’ve completed an Ironman. How is building a startup like training for a triathalon?

NK: It’s almost the exactly the same. Every founder should do an Ironman. It took me 15 hours to do it; I was 12 hours into the day when I came up to the first loop of the marathon and I was delirious. I started thinking, I’m about to be an Ironman. I didn’t realize I had another lap to go. It was just starting to be dark; I was lost in a swampland. There were signs saying, Don’t get off of the road. There are alligators. I equate that to the startup world. You have to turn around by yourself into the dark and just keep taking steps, one foot in front of the other.

I think in general, very few people can really do a good job talking about how painful startups are. And I think an Ironman is the same way. You mainly just want it to be over. Only after the fact do you realize what you’ve done, when every part of your body is in pain. When you’ve completed a couple of startups, you recognize you can do it again.

X: What did you want to be when you were a kid?

NK: Oh, that’s easy. I wanted to be a catcher for the Los Angeles Dodgers. My dad grew up in LA; I was born in Colorado and there was no baseball team so I became a Dodgers fan. Dad and I were at the San Diego Padres game, and Mike Scioscia—he’s now manager of the [Los Angeles] Angels—hit a foul ball. Dad and I were on the first-base side and the ball came right to me. It landed on the ground in a chilli dog and my dad dove to the ground and handed it to me. I still have it with chilli-dog stains still on it.

I thought that was a sign from God that I was going to be a catcher for the LA Dodgers.

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