Why I Started A Company That Looks Like An Airline (But Isn’t) and Why You Should Too*


In the list of things that I thought I wanted to do when I grew up, starting an airline was nowhere to be found; it has become one of the best experiences in my life. I had many different dreams of what I would be when I grew up, most notably a player for the Los Angeles Dodgers. My dad let me stay up late one night in October, and I witnessed Kirk Gibson hit a home run in the 1988 World Series. After that, I knew I was destined to become a ball player. I was good enough to get a scholarship to play in college, but my career stopped at the college level and I realized that my dream of playing pro ball player would never come true.

Becoming someone I didn’t respect

Since I wasn’t going to be a famous athlete I focused on my studies and deftly moved into the corporate world. After a few years working at EDS, I was given the opportunity to join a startup, and since I had nothing to lose, I jumped without abandon at the chance to explore the startup ecosystem. (On side note, if you haven’t done so, do yourself a favor and read On Wings of Eagles for a fascinating account of leadership by Ross Perot and the EDS team in 1978 in pre-revolutionary Tehran.)

That initial startup opportunity stoked an ember within me that started a journey that lead to the ground floor of several startup companies over the past decade. I am incredibly fortunate to have learned many lessons from leaders that bestowed on me job titles that I didn’t deserve, but took full advantage of. I learned how to sell a product that only existed on a PowerPoint (then worked seemingly endless hours to help construct the product we had sold); I learned how to have a “peer to peer” conversation with a room full of board members that I needed to convince to give us millions of dollars and I also have enjoyed the joy of selling a company that didn’t exist years earlier. By the way, selling a company should never be your first goal as an entrepreneur, like running a marathon and having a baby (according to my wife), selling a company is transformative, but mainly you just want it to be over; only years later do you fully realize what you helped create and appreciate the journey. The money is never the point, it is only there to keep score, nothing else. In the process of building these companies, I also accumulated over 2 million miles and several inches around my waste riding in the back of planes.

A race to the bottom

A race to the bottom

I remember the first time my American Airlines Executive Platinum Card arrived in the mail. I was ecstatic thinking that I had finally arrived only to turn around and see my beautiful wife with tears welling up in her eyes. I was too dumb to realize that I was winning at certain things while losing at the only things that matter. Put simply, I was turning into the man I didn’t want to become — a man building on a foundation that was bound to collapse

“Prosperity knits a man to the world. He feels that he is finding his place in it, while really it is finding its place in him.” C.S. Lewis

Finding my calling

I feel incredibly lucky to have found part of my calling at a young age in being able to identify macro trends and then finding ways to utilize technology to address these trends. With the exception of the hospitality of Trey Bowles and Jennifer Conley and the uncompromising team at the DEC who gave us a home when we outgrew my garage, I’ve never really been part of the startup scene. My idea of an “incubator” consists of several close friends, a bottle of Balcones Baby Blue and a late night by my pool listening to music and dreaming. What I do know is this: the world has problems and I am transfixed with a desire to go solve those riddles. While I was finding my place in the business world, I was also losing myself in my personal world. I was creating bad habits, was unhealthy, and was frequently tired. In a word, I was absent. Something had to change, and in a big way. I needed a way out.

The Epiphany

In our last company, I was fortunate to work personally with a brilliant man who also happened to be billionaire who owned a Gulfstream 550. If you’ve never had a chance to ride in a Gulfstream 550, it’s kind of like this: you’re riding on a cloud while savoring your favorite food and guiltlessly binge-watching your favorite TV show. Put simply, there is no substitute for riding in a private plane. It is nirvana. When I first experienced riding in a private plane, I dreamed of the prestige of showing up for meetings and casually complaining about the expense of jet fuel. However, after the initial glitz had worn off, I realized that it gave me something else I desperately needed my life. It gave me time.

With access to a private plane I could have breakfast with my family, have a business lunch in another city, and be back in time for soccer practice. A private plane gave me the freedom to do what I was called to do: build great companies and also be who I was called to be: a great husband, father and friend. A plane, to me, is basically a time machine that gives me the most valuable commodity in the world: time.

What's particularly funny is that when I decided to start RISE, planes were effectively magic to me. I had no idea how they worked. I just knew that they got up in the air, flew really fast and somehow landed safely. Riding in a plane was basically a miracle that happened every time I got in and strapped on a seatbelt. If I could somehow harness this power and democratize it for a larger population by making private planes more affordable, I knew that we could fix a problem that had caused me and millions of others so much angst. So I pulled out my journal, sat on my back porch, and wrote. I filled pages with thoughts, ideas and passions. I admitted to myself that I was scared. I admitted that this idea was bigger than Nick Kennedy. And I admitted that I had no idea what the hell I was doing. But I also acknowledged that if I could pull this off… I could fundamentally change peoples lives. Therefore, I had no choice but to take a step forward.

“Perfectionism is the voice of the oppressor, the enemy of the people. It will keep you cramped and insane your whole life...I think perfectionism is based on the obsessive belief that if you run carefully enough, hitting each stepping-stone just right, you won’t have to die. The truth is that you will die anyway and that a lot of people who aren’t even looking at their feet are going to do a whole lot better than you, and have a lot more fun while they’re doing it.” — Anne Lamott

The Power of Dreaming Big

I keep of list of Pro’s and Con’s of dreaming big in my journal. Certainly there are lots of upside to dreaming big: the power to do what you were called to do, finding satisfaction in your work and, of course, being recognized for being a dreamer. However, there are plenty of downsides as well: failure, embarrassment and of course, allowing your pride and fear to get the best of you. When you dream big you risk big, but I believe this where the real magic happens.

RISE is not my first venture that applied technology to macro trends that ended up making a huge impact on society, I have seen this movie before and I know how it ends. The last business I was part of addressed variability in oncology care. We used technology to give oncologists real time access to the latest medical information and consequently lowered non-evidence based care from 32% to less than 2%. Before eviti existed, one in three cancer patients received care that was inappropriate for their diagnosis. When eviti is utilized, variability in cancer care is virtually eliminated. We took a huge risk, trying to move the needle in healthcare and because we did, people are alive today that otherwise wouldn’t be. (For the record, when I started out on that journey, I could barely spell cancer, not dissimilar to my lack of knowledge of planes 12 months ago. If done with proper values and purpose, this can be a strength because you don’t know what not to do and you have the freedom to start from scratch. Find people smarter than you who are the best in your chosen industry, hire them and then get out of the way.)

With RISE we aren’t saving lives, but we are saving relationships and creating community. We get “love notes” from our members. These notes say things like “you’ve saved my marriage”, “RISE is changing my life” and (my favorite) “RISE is literally the best thing since the Internet”. We risked a lot to get where we are, and we have a long way to go, but now that we are here, the risk we took is starting to seem worth it.

Finding our Purpose

As a purpose-driven organization, we say that RISE is never less than profits (no margin, no mission), but it is so much more than profits. Every morning I wake up and I ask myself how I can serve the Executive team at RISE and then I ask them to find ways to serve their employees. Then we ask our employees to go serve our members. And so the cycle continues. The end result is that we are having an impact on people in ways that few companies will ever experience. We are fulfilling our purpose of giving our members the most valuable commodity in the world, time. Then we are enabling them to use that time to go do what they are called to do. It is why we exist. It is what we are called to do.

Drink the best wine first

I have dear friends who bring a bottle of wine that is way too nice for the occasion when we meet for casual dinner at the house. It could be takeout Thai food or pizza from the regular joint. It doesn’t matter the occasion, the wine is consistently better than we deserve. I used to balk at the idea of drinking the best wine if not paired properly according to a Master Sommelier, but my gracious and kind friends have taught me to live in the present by really savoring moments like this together. In following your dream, you are giving yourself the gift of living in the present; one of the best decisions you can make, you must follow the path that has been laid in front of you; to do otherwise is the turn your back on yourself, one of the worst decisions you can make in life. Get wise counsel, read a ton of material and then go forth on your journey.

One of our key values in RISE is Courage. We tell our employees, It is not always comfortable being courageous but it is vital for the success of our company. Move fast and break things. Don’t be afraid to make mistakes, just try to make them new mistakes. Giving our team the freedom to be who they were designed to be does not hinder our business. It is the very DNA of who we are and what enables us to fulfill our purpose.

“You might as well fall flat on your face as lean over too far backward.” James Thurbur

There are millions of reasons why you shouldn’t follow your dreams. Being scared is not one of them. Being scared is the one emotion you have that tells you that you may be on the right path. Have courage and take the next step; it might be the best decision you ever make.

Travel Better,


PS — Feel free to leave a note below, but I’d rather you spend your time looking for something bigger than yourself to get involved in. Start by checking out the work of some of our friends at LivestrongBig Brothers Big SistersWounded Warriors or My Possibilities. They are all doing great work and would love your help.

*Richard Branson famously said “If you want to be a Millionaire, start with a billion dollars and launch a new airline”, so don’t actually go start an airline. That would be dumb. Also, we’re a competitive bunch at RISE and we will likely put you out of business at some point and then it would just be awkward.