In Your 30s: Navigating the Ups and Downs of Entrepreneurship, Family, and Fortune

Cruising at 50,00 feet in a private jet flying to Atlanta from LA, the CEO said, “I believe we will do well together when this buyout is completed. You’ll make a lot of money and enjoy great success. Will you join me?”

I was thirty-one years old. I thought at that moment, “This is what life is all about!”

Sitting next to me was my future CEO. He was leading an unfriendly takeover of the public company I was working for at the time.

The Beginning

I started my thirties with a wife and two daughters. My wife was twenty-eight years old, and my daughters were two and six months old. My business partner and I had sold our business two years prior, and now I was embarking on a new career.

My short-term goal was to achieve the earn-out. This would complete our business’s sales successfully and establish me as a capable general manager. My long-term goal was to end the decade as the CEO of a billion-dollar software company.

What I didn’t know then but know now, my thirties were all about learning who I value and what I value. I started wanting what everyone around me wanted out of life. I ended up knowing what I wanted out of life—lots of learning here.

First Goal Achieved

Thanks to an incredible team of ambitious and talented people along with a market that was buying at the time, we achieved the earn-out. I was established within the public company that bought us. I was considered an up-and-comer. I was given a promotion and a group of companies to lead to the next level. I was now a vice president leading general managers. Together, our mission was to grow revenue, profits, and cash flow.

From Entrepreneur to GM

This was a hard job that demanded all my time and attention. Thus began my travel life. I was gone almost weekly, leaving Kathy and the girls to fend for themselves. I reckoned this was the price to be paid to achieve my ambition. I would not understand the cost of this separation until much later in my life. Suffice it to say, my ambition was not without consequences. Some were good, but others were not good.

I was known in the corporation as a general manager who hit his numbers. I was proud of that. If you reported to me, you knew the quality of our relationship was based on your performance. Hit your numbers, and you will be celebrated. Miss them, and you’re gone.

In time, this singular focus became a grind for me. It started out exciting. I loved the clear goals, developing the plans to hit the goals, and achieving the goals. I especially liked the rewards of success.

The Dog That Caught the Car

But after a few years of this, I was all about the money. I had adopted this value, but it didn’t sit well with me. I became someone I didn’t like. Yes. I was conflicted. The money was great, but I didn’t like who I’d become. This corporate value of pay for performance, which I adopted wholeheartedly, grew like a cancer inside me. It was creating an emptiness that I filled with things, experiences, and alcohol.

As my titles increased, along with my responsibilities, so did my income. I was trapped by the value system. Driving my charges to make their numbers got me to my numbers so I could maximize my income. This became my purpose, and as the years passed, I realized that it wasn’t enough for me.

My purpose, year by year, became less and less fulfilling. I was building nothing. All my creativity was focused on the end game: numbers. And as a close friend and national sales manager told me as he was leaving the office on December 31, "I hit my numbers. When I return to our office in the new year, I’ll be behind quota.” Chasing numbers became my hamster wheel.

Why Am I Doing This?

Meanwhile, Kathy was shuttling our kids to their private schools in her Mercedes station wagon. Then she went on to visit her shrink to keep her sanity. My life ambition did not keep either of our lives in any kind of meaningful orbit. We were meant to be together. Apart did not work well for either of us or, as I discovered later, the kids.

But my thirties were profitable. We had it all. We built our dream home and completely furnished it. We bought and refurbished a condo with an unobstructed ocean view in a premier resort. We were always driving new imported cars.

My thirties also comprised a decade of gaining incredible experience in business and life. It was a time to differentiate between wanting what other people valued and discovering what I valued. Admitting this was a painful process. When I told those who knew me at the time that I was unhappy, they would look at me like I was crazy. They didn't understand. After all, I achieved what we all wanted in life, right? The pain was to admit I didn’t fit in anymore. We had different values.

At that time, I knew what I was doing wasn’t right, but I didn’t know why. I was blaming the business I was in and all the people involved. I lacked perspective. I didn't know, think about, or discuss values. They were obvious to all of us—success, money, position, power, and lastly, family.

The crowd I hung with at the time shared these values. In their view, there wasn't anything to talk about. All I knew was this: I was unhappy and unfulfilled. I was the dog that caught the car. I realized then I shouldn't be chasing money. But if I didn't chase money, what was I supposed to be chasing? This was the right question. My doubt showed in my face. Everyone saw it. My boss said to me over breakfast, “If you are not happy here, it is OK to leave.” I did. Now what?

It Was All Gone in an Instant

By the grace of God, I didn't lose what mattered. I never lost my love for Kathy. This statement may seem obvious to you. But when chasing money, living on the road, and hanging with people with different values, this love is constantly under attack and at risk. I've seen it play out too many times.

And I never took my kids for granted. I loved them and thought about them all the time. I loved being with them. My life would be an empty shell without my children. They are each so gifted and precious to me and always have been. The constant travel simply made my love and devotion less obvious to them. There is no substitution for time together.

Here I was...

Unhappy in my occupation

Unemployed

Wife and three kids with one on the way

Custom built home

Condo at the beach

Private school tuition

No prospects for employment

No idea what to do, but knowing I had to do something

I was no longer willing to do anything for money.

The first decision I made was no more business travel. I never challenged this again for the rest of my life. I was going to be an Atlanta resident who didn't leave town except for vacations.

I knew this was the right decision for me, my marriage, and my kids. I trusted in my business acumen and skills to be successful at work. But what work? I didn't know.

I missed building businesses from scratch or at least the very early stages. It scratched an itch I had every day while working in corporate. The creativity necessary to get a startup to revenue, combined with the pressure of achieving positive cash flow, was missing. As crazy as this sounds, this is where I knew I needed to be.

My assumption, which proved terribly wrong, was I needed to be an entrepreneur again. I needed to be the person running the business. What I discovered was that I needed to help people who had corporate experience start and build their own companies. My role became what I termed an active angel investor.

This discovery and how I got there, which I wrote about in detail in the past, eliminated conflicting values. For the first time in a decade, I realized my values and work were in alignment. I lived and worked in startups with new entrepreneurs who were experienced business people. They knew their industry. They had leadership and management experience. They had corporate business discipline. They were missing two pieces. They had no idea how to start a business from scratch, and they had no understanding of cash flow. That's where I came in.

The way I told this story makes the whole transition from corporate titan wannabe to angel investor seem painless. It was anything but that.

My Unhappiness Became Depression

Right after I left my corporate career, my drinking exacerbated the depression. My drinking was cause for emotional separation from Kathy and the kids. All of this had me living a life counter to my values, and I didn’t know how to live these newly realized values.

Out of seemingly nowhere one night, while drinking, I had a vision. If I continued to drink, I would lose everything. I would lose my precious Kathy, my kids, and my career. I would have nothing. It scared me into a radical change. I was invited by a neighbor, a recovering alcoholic, to attend an AA meeting.

I attended one hundred and eighty meetings in one hundred and eighty days. During that time, my mind and body started to clear. Then, my spirit was awakened. I realized the “God of my understanding” did a miracle in my life. He got me to AA. He took away my desire for alcohol. He cleared my head. He was calling me.

I wanted to know this “God of my understanding.” People I worked with in the past who were God followers came back into my life just then and helped me on this journey. Along the way, I encountered Jesus. He is the God who gave me the vision, led me to sobriety, and brought me to him. He forgave me. He loved me. He took away my sin and its associated guilt. He made me a child of God. I was made anew. The old me was gone. The new me had come. I was born again.

And that's how I ended my thirties. I started with unbridled ambition. By thirty-nine, I was unemployed, clueless, depressed, and addicted to alcohol. By forty, I was sober, a child of God, and an active angel investor. I was on fire for Jesus and on fire for entrepreneurs.

It was my thirties that laid the groundwork for the man I am today. The last thirty years could not have happened without my thirties’ decade. That decade was painful, exciting, confusing, profitable, and renewing. Knowing the stories of many men has convinced me that my story is not unique.

A Gift of Time

On March 2, Nick, our youngest son, celebrated his thirty-first birthday. We decided on a whim to buy him a watch. We felt a watch would be something he would value, use, enjoy, and it would become a part of his family.

When we bought it, we weren't thinking much beyond it being a really nice gift. This changed when I sat down to write the birthday card that would accompany this gift. I realized while writing the note that this birthday and this gift were so much more.

Letter to My Son

“This watch signifies the beginning of building the rest of your life. As a graduate who was fortunate to choose an occupation you excel at and enjoy, you now are on the precipice of mining your education and occupation built in your twenties. You are on a path that will lead you to the richness of life. Your most important choices will be made in the next ten years. These choices will result in the community you live in. And it is within this community that your life’s trajectory will be established.”

My prayer is for my son. I hope that in ten years, he will look at that watch and remember all he’s been through. A lot happens in ten years. I know his story is going to be exciting, difficult, and profitable. It happened to me. It will happen to him, too. But now it’s his story.