I Am Starting Something New


Paying It Forward


Since the news came out about selling RISE, I have been asked more times than I can remember, “What are you going to do next?” For those of you have asked; first, I am working on being a better husband, dad, brother, son, and friend. Secondarily, I am mentoring entrepreneurs at the Capital Factory, serving on several boards, investing in interesting companies, writing a book on my journey from a convict’s son to CEO, working with Dr. John Townsend at Townsend Leadership (more on this later), and working on perfecting my Manhattan recipe. I am also working with friends to scout land in the mountains of Montana (see picture on my homepage) to create a retreat for entrepreneurs who have been bruised and need to replenish the relational nutrients that become dangerously depleted while building our businesses.

"If you put shame in a petri dish, it needs three ingredients to grow exponentially: secrecy, silence, and judgment. If you put the same amount of shame in the petri dish and douse it with empathy, it can't survive." Brene Brown 

The Story Behind The Story

About five years ago I sent out an email to 128 people with the title, “I am starting something new.” That email described RISE, which at that point was barely more than idea started above my garage, that turned into a business that touched hundreds of thousands of lives and will forever change the way we access air travel.

Through that experience, I learned empirically that a team with unambiguous Values, Vision and Purpose can do anything they put their mind to, including launching and running an airline. The last half decade was filled with the roller coaster emotions associated with the startup life; “I’m on top of the world” followed by “I am such an imposter, I have no idea what to do next, but all these people are counting on me” and all the emotions in between. And like most life-changing journeys, it was soul-crushingly hard, but I wouldn’t have had it any other way, the journey taught me more than the destination.

To the people that built RISE, I will be forever grateful for your contribution to our story, you should be proud of what you created. From the bottom of my heart, thank you.



Most people don’t know this, because I carefully hid the truth from anyone but intimate friends. But when I was 16 my life imploded when my dad was sentenced to 20 years in prison, and I assumed the identity of a convict's son.

Crossing the manhood bridge was supposed to happen in this season, but instead, the train leaped and buckled and left the tracks. My entire world was spinning, and the only way that I could continue to exist was to be as still as possible and exude false confidence. So I decided to become my own self-made man. In control and impervious to my negative realities.

In short order, people noticed my stoic personality and began to praise me for being “strong” and “mature,” and I took that to mean that I was doing the right thing. I was starting a multi-decade process of taking my raw emotion, the very essence of who I am, and packing it deep down inside for no one to see. It was the absolute worst thing for me to do.

My accelerated maturity began to become my reality. I was able to help, and I was able to provide, I was able to manipulate my reality into something more palatable, something I could survive in. And that mindset, that I learned as a 16-year-old became my addiction. A drug that has brought me much wealth and power and the one thing that I wanted more than anything else in the world, to be in charge of my destiny and the author of my own rules for my kingdom.

Unfortunately, the story I created was not half as endearing as the one that is inside of me.



A few years ago, a friend suggested that I become a member of a group called Townsend Leadership Program (TLP). When I was initially invited to join TLP as a member, I thought I didn’t need it, but Angela gently insisted, and I am so thankful she did. 

TLP is a professional leadership development program founded by Dr. John Townsend who is a psychologist and New York Times bestselling author of Boundaries and over 30 other books on growth, selling over 10 million copies.

The holistic model is based on both Competence and Character, helping leaders with their “task skills”, such as strategic thinking, vision alignment, role clarity and execution, and also their “people skills”, such as emotional intelligence, engagement, motivating others, and listening skills. When Competence and Character are connected, we can begin to be fully integrated and find peace for what ails us.

I learned the truth that my hurts and hang-ups that caused conflict in my personal relationships were the same hurts and hangups that caused conflict in my business. Similarly, the passion that fueled my company was the same passion the grew my personal relationships. Through intentional work within the TLP framework (and a healthy dose of grace, truth and time), I was able to connect my personal life and my business life, integrating my negative realities, grieving my losses and more fully understanding who I was created to be and how to best access those gifts. In the end of the 12 month process, I found the peace that I had been searching for nearly two decades.



I have been asked if I feel different about entrepreneurship after I’ve gone through this process and the truth is, I do. Many entrepreneurs I know have a quote on their wall that says "The dream is free but the hustle is sold separately." Those ten words are true and are often what separates the successful, from the dreamers. Hustle, grit, and determination were the three main characteristics that helped me accomplish my success. They are the skills needed to look out into the universe and believe that you can do something that no one else has ever done before. They are beautiful, and they are necessary, and they are almost uniquely endowed in people who come from brokenness. 

When I started RISE, I had a massive hole in my heart because of the absence of my father. Hence, when we launched we never focused on giving access to private planes, we said from day one we didn’t sell seats on a plane we sold seats at the dinner table. Meaning we were providing a way to avoid the laborious airport process - parking, TSA, crowded gates and full planes with cranky staff - and all the time that process stole from us each year. It was never about the planes, we sold time, the most precious commodity in the world. We sacrificed so that families could spend more time together and relationships could flourish. That was our vision, and we did it well. So well, that we were written up in the New York TimesWall Street JournalUSA Today and dozens of other publications, I was added to the Ernst and Young Entrepreneur Hall of Fame, and RISE was acquired. 

I was so wounded by the absence of my father that I was willing to risk almost everything I had so that other kids wouldn’t have miss out on their father as I did. That passion is one of the reasons we were successful, and it is what drives a lot of entrepreneurs in their quests. That same hustle, grit, and determination should accompany any business venture, to do anything less are to invite a higher chance of failure.

Starting a business and making payroll is one of the highest honors that one can have. In doing so you get to provide for your employees and their families financially, but you also get to help architect a safe and nurturing environment where they will spend over 2,000 hours a year. As a business executive, you have an opportunity to be one of the most significant positive influences in their lives, bringing healthy and consistent growth to your organization, your community, and the world. But this growth starts with you and can only happen if you are competent in your Competence and Character; the best business leaders know this and integrate it deeply into the culture of their businesses. 



We sold RISE nearly two years ago, and in that time I have spent countless hours reading, writing, meditating and living in a loving and truth-telling community to reflect on my journey, and I have honed in on an important truth; I have to pay it forward.

I loved the process and outcomes of TLP so much that I decided to become a Director to have the honor and privilege of walking with people on the longest journey of their lives, the 18 inches between their head and the heart. My first TLP team is underway, and I am starting a second team in April. I can already see the lives of the leaders starting to be transformed and its honor to be a witness to their unfolding story. TLP is a time and financial commitment, but I can guarantee you that your ROI will be beyond your imagination; I know from personal experience. 

If you are interested in learning more about TLP, looking for great books to read or learn more about my story, you can find me at www.helloimnick.com

With Respect, 


Nicholas Kennedy