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Nick Kennedy

The audacious entrepreneur seeking to change travel forever.

I hope many of you have the good fortune to meet Nick Kennedy at some point in the near future.

As an entrepreneur, he's impeccably well-spoken, sporting an aura of audacious confidence that's incredibly/unfairly contagious to those around him. At the same time, it's tempered by a general self-deprecating wherewithal, avoiding any hint of arrogance or otherwise.

He's just a good leader and a strong visionary. And he's not afraid to tell you that he has no idea what he's doing, from time to time.

So, as a person, you'll be unsurprised to hear that he cares deeply about the people around him. From his family to his employees, he has no qualms about dropping everything on behalf of someone he cares about. (Or, equally, if it's the right thing to do.)

As a whole, the result is quite an inspiring character. Someone who's set about redefining air travel for a legion of people who spend far too much time in the air and all too little time with people on the ground.

We had the pleasure of chatting with Nick — and shooting alongside one of the RISE planes — about the genesis of his career, his next steps, and more.


Matt Alexander: Everyone knows you as the man who audaciously started an airline. We’ll get to that story, but, first, tell me what you were doing beforehand? What’s the pre-RISE story of Nick Kennedy?

Nick Kennedy: Well, RISE isn’t technically an airline. We’re a two-sided technology platform that connects our members with access to private planes through scheduled and on demand flights but, as you said, we’ll get to that story later.

I guess you can say my story started in California where I grew up. Although, I enjoyed school I was never the best student but I’ve since learned that most entrepreneurs aren’t. We’re a restless bunch of renegades with little regard for rules and structure which makes school a challenging environment. Thankfully, I was good at baseball and managed to get a college scholarship to play baseball in Arkansas. It was there I met and married my beautiful wife, Angela.

Shortly after graduation, I was recruited by EDS and moved to Dallas. Although I had a great experience, I quickly came to realize that I wasn’t cut out for cubicles and corporate hierarchy.

I made the leap from Corporate America to help start several start-ups in the healthcare space. The first one was a check-in kiosk company. It was acquired by NCR in 2006. The most recent one, eviti, was an oncology decision support platform and was acquired by Patrick Soon-Shiong before being rolled into NantHealth and taken public this year.

Matt Alexander: Have you always been entrepreneurial or is it a more recent development?

Nick Kennedy: I’ve always been obsessed with problem solving and doing things differently.

In college, I opened an all-you-can eat pancake business in my dorm room. It was so successful the university shut it down two weeks in. But even in that business I was solving for something: figuring out a way to feed hungry and cash strapped college kids like myself using the most economical product possible – pancake mix.

For me, being an entrepreneur is just a way of satisfying my insatiable curiosity and hunger for problem-solving by turning it into solutions that hopefully solve other people’s problems as well.

Matt Alexander: How did you come across the notion of starting your own airline?

Nick Kennedy: I spent a decade accumulating over two million airline miles.

As my businesses grew, my relationship with my wife, kids, and friends started to suffer. And anyone who travels as frequently as I did can attest to what a soul-crushing experience it is. You literally start to go crazy.

It was in the midst of that craziness that I had the opportunity to fly on Patrick’s private jet for the first time. It was like I had stepped into a virtual time machine. This one asset allowed me to be in a meeting in one city and back home in time for dinner with my family.

So, I became obsessed with figuring out how to provide time-strapped professionals – a simple and more economical way to access this form of air travel.

Turns out, there are a lot of underutilized private planes owned by hundreds of operators all over the country. We built a technology platform that allows us to access this inventory and then create both scheduled and on-demand services on top of it. In doing so, we are handcrafting a two-sided, symbiotic marketplace. First, helping business folks get time back in their lives through the elimination of lines and other hassles associated with commercial travel. And, second, by allowing operators to fly their planes more frequently. Which, in turn, results in them buying more fuel, hiring more pilots, and so on.

We’ve flown over 20,000 member segments and we are seeing consistent month over month growth.

We’ve flown over 20,000 member segments and we are seeing consistent month over month growth.

Matt Alexander: You’ve been flying for a year or two now. What’ve been some of the biggest lessons you’ve learned so far?

Nick Kennedy: The majority of great things in my life have come from taking major risk and RISE is certainly no exception. Just ask my lovely wife who taught me about the finer points of dating.

Start-ups are incredibly risky and adding airplanes to the mix makes it exponentially harder but I knew in my heart that if we could succeed in giving time back to weary travelers who were building successful careers — but also wanted to be home with family and friends — it would be well worth it.

Another lesson I’ve learned is that it’s incredibly important to build a team around a purpose. Give them the framework to make decisions. And then get out of the way as quickly as possible.

About a year ago I wrote an article on Millennials in the workplace that struck a chord with a lot of people. Over half of the workforce at RISE is comprised of Millennials and they are some of the most humble, hard-working professionals I’ve ever had the pleasure of working with. Sharing those observations and successes from my personal experiences is definitely a passion of mine.

I’ve also learned that what seemed like minor decisions early on have major implications down the road and that having wise counsel both inside and outside the business is worth its weight in gold.

Matt Alexander: What’s next for you and RISE?

Nick Kennedy: In one word: growth.

We have 20 additional cities on the horizon that we intend to roll out over the next two years in addition to several new products and services.

We’ve worked hard to create a simple and elegant process for our members centered around an exceptional customer service culture and ability to book flights in under 10 seconds.

In this past year we were featured in several major publications including the New York Times and Wall Street Journal

I have always shared my Big Hairy Audacious Goals with the anyone that will listen because I believe we have lightning in a bottle. Our +97 NPS score is a testament to the RISE team and we are excited to share that experience with tens of thousands of people.

Matt Alexander: If there’s one piece of advice you could impart to aspiring entrepreneurs, what would it be?

Nick Kennedy: First and foremost, be true to your roots.

RISE exists to give people back time in their lives. Providing them easier and more economical access to planes is just one way we do that. We are in the process of rolling out a new advertising campaign that speaks to the purpose and vision of RISE. It’s very simple: we allow you to “be there” more in life and business.

As long as we stay focused on that goal, there’s no limit to what we can accomplish.

Secondly, be courageous. I tell this to my employees every single day. Literally. They all say, "Nick, we totally get it…be courageous." But this tiny piece of wisdom stems from years of battle wounds and facing some of the toughest days you can imagine.

Lastly, a happy entrepreneur has almost no past and an unhappy entrepreneur has nothing else. Mistakes are okay as long as they are new ones. Build a culture that embraces the new mistakes, learn from them, and only make them once.

Oh, and a bottle of Angel’s Envy rye can help put most problems in perspective.

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