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My Life Story

so far…


Hello, I’m Nick.

I was born in Colorado and raised in California in a loving and fun family. However, when I was 16, my world imploded when my father was sentenced to twenty years in prison, and I involuntarily exchanged my upper-middle-class life for the life of an Angel Tree kid. I spent nearly two decades of my life — from adolescence into adulthood — visiting my father in prison.

The youngest of three, my oldest brother was born with Klinefelter syndrome, a chromosomal abnormality that allows his 6’2 frame to display his nearly five decades on this earth, but keeps his mind consistently as a seven-year-old. He is a beautiful and gentle giant that still plays with remote control cars and provides hours of enjoyment for my kids when “Uncle Robby” come over to swim and play. Watch out if you find yourself around my brother with anything sweet, he will find a way to get his hands on it without you ever knowing.

My sister April is an intellectual force who somehow manages to have equal parts passion and empathy in her soul that translates into love without condition. She’s a great mom and wife and helps high school students in Virginia find their purpose. She knows me and my faults intimately and still chooses to intentionally lean into me even after all these years.

The three of us have been to hell and back, and we have the scars to prove it, ask our spouses and therapists.


“My daddy commissary made it to commas” - Kendrick Lamar and Nick


The summer before my junior year of high school, my father’s trial began in Colorado. I don’t remember much before this time, probably because I was self-absorbed or perhaps I have just blocked out my memories. Nonetheless, when the school year was about to start, and the trial was not over, my sister went to college, and I somehow convinced my parents that I was mature enough to live in San Diego by myself. Mom, dad, and Robby stayed in Colorado, and I went home to start the school year.

The school year started without much drama, and I was loving living on my own. I had good friends, was in the best physical shape of my life and eating fish tacos on the beach without much parental supervision. As far as I could tell I had reached the apex of my life at 16. Little did I know that I was about to go from the top of the hill to the pit of despair in short order.

A few weeks into the school year, I was sitting in English class when the bell rang, and I gathered my books to make the track down the hill to my next class. I was walking by the newly built gym and probably laughing with some friends or flirting with a girl when I looked up and saw a woman at the foot of the stairs leading to the dank locker rooms that looked remarkably like my mom.

I had spoken to her the night before in a quick check-in to assure her that all was well on the home front and to ask what the latest on dad’s trial was. In that phone call, she told me that she would call with any news and so I knew that this woman could not be my mom, because I had not received a phone call as she had promised.

I have no idea how she heard the judge read off a guilty verdict of her husband and somehow booked a plane ticket, got to the airport and made it to my school in what seemed like no time. But there she was, flesh and blood, tears streaming from her eyes; this is a testament to my mom, soft and kind and gentle on the outside with a core of granite that could hold the most dysfunctional family together. We embraced, few words were exchanged, the truth hung in the air, and we were unable to escape it.

Visitor after the well-meaning visitor came to our house to offer their condolences and I found myself in an odd position as an adolescent, wanting to seem in control and yet unable to stop the fall into chaos. I was numb to the activities surrounding me, the words came out of the visitor’s mouths, but I could barely hear a sound. The sounds that I did hear were so trite and pathetic given the current circumstances that I quickly built up a defense mechanism that engaged whenever lips parted, and aimless air emerged.

This mechanism is strong within me even today; what could you possibly say that I don’t already know?

Pride has robbed me of so much knowledge.

I rarely cried in public. 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. Looking back I realize how silly my thoughts were, but one does not have much time to prepare for the catastrophic changes that a father in prison will have on the psyche of a 16-year-old boy.

Crossing the manhood bridge was supposed to happen in this season, but instead, the train leaped and buckled and left the tracks. So I decided to become my own self-made man.

In short order, the visitors 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 began packing it in 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.

My worth was becoming tied to my self prescribed identity as an independent man.


“A happy man has no past, while an unhappy man has nothing else”


I admired my dad, loved him and wanted to be like him. I believed that I was a reflection of him and I was proud to think that maybe someday if I played my cards just right, I could fill his shoes. With one strike of the judge's gavel, I no longer wanted to be like him, and I became enslaved by the thought that he may be a reflection of me. This thought has consumed my mind, a constant companion that has left me without peace and full of angst for years.

When my father became a number in the prison system, he didn’t just take his physical presence with him. He took our financial security, our identity and the blueprint for the future we had mapped out together. The day he was convicted, life as we knew it no longer existed and we were left to create a new path forward — one that was about survival. In a way, I was experiencing the death of my dad. Although he didn’t physically pass away, the man I had known and loved my entire life ceased to exist. There are many support groups and books about grieving the loss of a loved one to death, but this was something different. A purgatory of sorts where you exist somewhere between a life you knew and the life you now have. It was a nightmare, and I had no way to wake up.

Overnight, we went from not wanting for much to having nearly nothing. And since we needed a place to sleep and food to eat, my mom and I both got jobs. Together we scraped together enough to take care of Robby and us. I went from the homecoming court to a regular prison visitor, and I became intimate with two companions — Embarrassment and Shame.

I took on the title of the ‘‘man of the house” in what was initially an altruistic gesture that morphed into a monster that has ruled my mind for the better part of two decades. I began the building of my kingdom, brick by earthly brick, in which I found ways to pack my embarrassment and shame deeper into its foundation so that no one would ever see behind the walls or know my weakness. I became determined to build a trophy room so grand and opulent that it would surely hide any semblance of what was indeed happening in my head.

I carefully crafted my identity in such a way that this truth would never see the light of day unless you were a trusted and intimate friend. For 20 of the most pivotal developmental years my life, I walked around with an albatross of shame around my neck because  my hero, mentor, friend, and father stepped out of our home and into a life behind bars.

In doing so, I packed the very essence of who I am: my values, feelings, passions, thoughts and my history in an emotional vault, closed the door and threw away the key.

The walls were thick and impenetrable and hidden. Or so I thought.


“Sometimes the story we’re telling the world isn’t half as endearing as the one that lives inside us." Donald Miller


For over ten years, Angela and I have participated in a community group within our church. The purpose of this group is straightforward; we aim to live life together in a community of love and grace. For the past several years, almost every Sunday night a group of nearly 40 people representing seven families would converge on our house, and the kids swim or watch a movie while the adults share what is going on in their lives; afterward, we share dinner and continue the discussions. This group has been instrumental in our lives, through the good times and the bad times and has been a shoulder to lean on more times than I count. It is no small feat that we have been together for so long, and one of the reasons is because we have chosen to be vulnerable with each other by refusing to allow shame to dominate our conversations. As Donald Miller so aptly observed, this group gets to hear the stories inside of us, the real stories

Long before we were part of this group, they began a tradition of having the adults share their four H’s (History, Hero’s, High times and Hard times) with the rest of the group. This exercise is one of my favorite experiences in life because we hold nothing back. Each member of the group gets to stand up in front of the rest of us and share the story of their life. We actively choose to love unconditionally by giving grace to each as they walk us through their journey. Because of this, often emotions flow from deep inside and manifest themselves through tears or confessions that have been stifled through years of secrecy and silence. We create an environment of vulnerability in our community group that allows the individuals to share “the story that lives inside of us” and in doing so, we connect on a unique level.

The brilliant Brene Brown says, “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.” The process of four H’s remove secrecy, silence, and judgment and replaces it with empathy and the shame disappears.

A few years ago we had a new family join, and so we began the new relationship by introducing ourselves through our four H’s. Once again, the power of this tradition held true, and each and everyone in the group gave us the gift of vulnerability. I had asked one particular member of the group several times if they would like to share their story at the next meeting, but there always seemed to be an excuse. Finally, when everyone else already had shared, and they had no choice but to share, she told us a story about their father and his life filled with mistakes that brought much embarrassment and shame into her life. This man had indeed made many mistakes and caused much harm to his family, but my friend had risen above this, created a beautiful experience and had become a better version of her father. It was a beautiful story that made me a better person for having heard it, and I was thankful for her courage.

After the meeting, while we gathered to eat dinner in our kitchen, I approached her person to thank them for the generous gift they gave us in sharing their story with vulnerability. I continued. “I have to ask you a question. Your story is beautiful and moving, but it seemed like you were hesitant to tell your story, even after I asked you several times, was there any particular reason?”

Through tears, she said, “I am so embarrassed that my father is a reflection on me and I was afraid of what everyone else would think.”

I was confused by her response knowing that the truth, and without hesitation, I responded, “Oh friend, your father’s actions and consequences are his alone. He is no reflection on you.”

As the words left my lips, I had an odd experience where it was like I heard a voice that was not mine, say the same words at the same time. It was almost as if I was speaking into a microphone that could change my voice and I could hear my words coming from another man’s mouth. I can’t explain it any other way than to say what my friend Kevin McConnell has taught me, ‘God is either sovereign, or He is not, there is no other option.’ I know it sounds crazy, but I choose to believe that God spoke to me at that moment by sharing with me the truth that was coming out of my mouth, that my father is not a reflection on me.` That audible whisper in my ear began to penetrate my own heart and slowly pried open the emotional vault that I had locked years ago.


“I see you” Angela


Around this time, my wife, Angela and I began to tolerate each other. Angela is a physician and at the time was homeschooling our kids while I was fulfilling my self-created destiny of building an airline from scratch. The stress of this life began to grow until we reached the final stage before a divorce, where you stop fighting and begin to tolerate each other.

Luckily we had some friends who saw this and encouraged us to seek counsel. I was wary of this option, thinking I was more than capable of working through my problems but agreed to go as a peace offering.

At our second session, during a heated discussion about a topic I don’t recall, our counselor looked at Angela and said, “Why don’t you tell Nick that you see him.”

Silence hung in the air.

“Wait, you want me to say ‘I see you’? Why would you want that?”, Angela replied.

“Just try it.”

A bewildered look crossed my wife’s face, and an even more confused look rested on my face.

We had been married nearly two decades, and I don’t think that we had ever uttered this phrase to each other. It was weak. It was ambiguous. It was milk toast in verbal form.

But since we were paying through the nose for this conversation and since we were on the clock, she did exactly as she was asked.

“Ok. Um, I see you.”

After all the scenarios we had encountered together, we rarely found awkwardness in our relationship. This moment was an exception to that reality.

Something magical happened in those three words.

Empathetically and with a breath of fresh air she continued.

“I see who you are, what drives you, what you long for, what scares you and what you are trying to be. I see your secrets, and your silence and I don’t judge you, I have empathy for you. I see you.”

The phrase struck me like a board across the forehead. I don’t know that I had ever had anyone say that to me in my 40 years on this earth.

After all these years, “I see you” was the phrase that opened my eyes to my needs. I needed to be seen, acknowledged and known for something beyond my accomplishments.


“when we are no longer able to change a situation, we are challenged to change ourselves” - Victor frankl


You know how sometimes when you start bath water and let it run for a little while so that it gets good and hot? After a few minutes, when you come back to the bath and place your hand under the faucet to feel the temperature of the water sometimes, you let the water get so hot that for a split second it feels cold? That was me.

I was so broken that I didn’t even know it. I lived an illusion that my life did not fall apart decades ago, or at least that I could somehow keep our life together, and since my life did, in fact, fall apart, my illusion has become victim to the pressure of time. I have tried for years to keep the pain at bay not realizing that, in doing so, I have denied myself the gift that grieving gives you.

At long last I faced the loss and allowed the grief to crush my illusion, giving me the gift of softness and illumination.

After years of carefully constructing the perfect life filled with everything, a rational man could want I now realize my Net Worth has absolutely nothing to do with my true worth as a child of God.

Shortly after selling my business, I was asked to participate on a panel for a bank that was put together for business owners who were contemplating selling their business.

Seated on the dais with a pair of investment bankers, a tax expert, and a fellow entrepreneur, I found myself nodding in agreement with most of their strategies to maximize the value on your business while creating a creative tax strategy to manage the proceeds. It was all very accurate and necessary. However, as we neared the conclusion of the event, I knew in my gut that we were missing a key component and so I asked the emcee if I could address a silent issue.

“You have heard a lot of valuable information tonight, and you should use these experts” pointing to my fellow panel participants, “they will cost you a pretty penny, but they will be worth it to maximize the value of your hard work.”

“But you need to ask yourself a more fundamental question. What can you do with $20MM that you can’t do with $10MM, or $200MM that you can’t get with $100MM? When you enter negotiations for selling your business, you will want to fight for every last penny, and the reality is you should separate yourself from that fight and let your investment banker take that role otherwise you may find yourself gaining the world and losing your soul.”

I continued, “The reality is that there are a myriad of easier ways to make money than starting a business from scratch and if you are anything like me, your identity is completing intertwined with your title. When you wake up the morning after the deal is done and your bank account is larger than you ever imagined, if you are honest with yourself you will feel empty because it won’t be as you imagined. You’ll spend a little money, and you will feel a little better, but the reality is that you traded your identity for cash and there is no worse deal in the world. I am the son of a convicted felon who spent nearly two decades in prison, and I went from being a statistic and to being on this dais tonight. I can tell you without a shadow of a doubt that the difference between being homeless and billionaire is just a few important decisions.”

I hated the feeling of shame and early in my adulthood, I became determined to mute my shame by any means possible. Luckily for me, it turns out that I had a knack for helping build game-changing businesses predicated on audacious goals that few dared to address - when you have little to lose, it's easier to risk it all. So I used that God-given strength to build a castle built on sand.

C.S Lewis says "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." I was feeling right at home in my new identity as a self-made man. So I set out to build a castle so grand and opulent that it would hide any semblance of what was indeed happening in my head. After several startup exits, being lauded in the press and being added to the Ernst & Young Entrepreneur Hall of Fame I had finally reached the point that I could take a breath and look at the world I had built.

When I examined from afar, I was pleased and the grandeur of my castle, it was better than I had dreamed. With pride in my heart, I gathered my friends to examine my castle so I could revel in my new identity. One of the friends empathetically examined closely and suggested that I may want to take a closer look at the construction materials.

Initially indignant, but unable to shake the feeling, I began to slowly stroll the hallways, moving my hands along the wall, testing the strengths of the floor and investigating the rafters. I did not like what I discovered. The walls were constructed of shame, the floor of anger and rafters of pride. The paint was a beautiful hew of hustle; from a certain distance it looked magical, but up close it chipped easily and needed to be replaced frequently.

I learned all of this through a lot of hard work to become a healthy and fully integrated individual, and being a member of a Townsend Leadership Program (TLP). TLP has been instrumental in giving me the framework to be able to ingest seemingly disparate data points into a coherent message that integrates my business, personal and spiritual worlds. My group is led by Nancy Houston, and she has been integral in my healing.

About halfway through the 12-month TLP program, when we went through the Affirmation and Challenge day. I had a breakthrough that lead me to want to help others find the peace TLP, Nancy Houston, and the Holy Spirit have given me.

As I sat in a circle looking deep into the eyes of the other members of the group that have given me the gift of intimacy through vulnerability, hearts raced, tears welled up in our eyes and smiles crept in as certain words are uttered in sacred reverence.

I was second to last to go, and I got to witness several other individuals ingest the truth that was being spoken into them. Even though I was watching closely and trying to prepare to receive my affirmation and challenges from the group, I was woefully prepared to hear what they had to say.

If “I see you” from my wife was the amuse-bouche then this process was the appetizer, salad, soup, entree and dessert with wine pairings from the hills of France.

At the end of the readings, Nancy asked me how I felt, and through tears, I uttered the only words that I could possibly say “I feel like I am going to be okay.”

From the time the judge's gavel struck, my biggest fear had always been that I would never be able to do enough to provide for my family and me and I had wondered if I was going to be okay from the moment I saw my mother crying when I was a junior in high school. Over two decades later, I finally had an answer to my question.

I am going to be okay, and you can be okay as well as long as you have the courage to pry open your emotional vault and take a peek inside.

Through TLP, 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 fueled my personal relationships. Through intentional work, 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. I was a changed man.


“Nothing that you have not given away will ever be really yours.” ~ C.S. Lewis


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. We sold time, and we did so 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 Times, Wall Street Journal, USA Today and dozens of other publications and I won the Ernst and Young Entrepreneur of The Year award because of the dream and the hustle.

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 to do so. That passion is what gave us success, 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.

However, I am now of the opinion that a business is never less than making money, but it should be so much more. Starting businesses 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.

Simply put, as a business executive you have an opportunity to be one of the biggest influences in their lives. This duality allows you to marry your private and public lives so that you can be fully integrated creating the opportunity to influence generations.

Now that I know this, I am planning to help others by teaching the business skills that grew my earthly kingdom beyond my imagination along with the emotional skills that allowed me to be fully integrated and connected in my community.

That’s my story, what is yours?

With Respect,

Nick Kennedy