Lessons As A Young CEO

“I have no desire to be a leader.”?

These were the thoughts that circulated in my head during the winter of 2019 as I reflected upon going on 7+ years of running an organization. As I looked upon the team that I had built, I faced the tough reality that if I had to rebuild the company, I wouldn’t hire back 50% of the people on the current roster. Through my own mismanagement, I had built a culture that lacked accountability, spread gossip amongst one another and couldn’t handle feedback from one another and clients.

This may sound like a harsh reflection for a first time CEO at age 29, but it’s the truth. I got myself into that situation because leadership is something that I’ve shied away for the entirety of my life.?

During my senior year of high school, I was the only senior who started to not be elected as a Captain. The coach very well could have put me into this position of leadership, however, he didn’t because he believed I didn’t care about the honor and some of the other seniors would destroy the team if he didn’t put them in charge.?

While this event happened over a decade ago, it still echoes my thoughts on the topic. I work my ass off, I don’t care about being recognized publicly, and I resist my own power. I care about solutions and results which allows me to create my own reality distortion field (to use a Steve Jobs reference) of where I put my focus. These may sound like admirable characteristics of a man who puts his ego to the side for the betterment of the collective, but this mindset will only take you to a certain level of success in your professional career.

This mindset allowed me to grow my company to a level of operations in which my leadership consciousness had not caught up to just yet. It’s as if I blinked my eyes (after spending 7 years with my head down) and I suddenly went from operating a company out of my childhood bedroom to having a dozen people depending upon me to pay rent each month.?

While this was all going on within my company, I just so happened to sign up for a leadership development program in 2019 in San Diego called Ascension Leadership Academy (ALA). The funny thing is that I didn’t join a leadership training program to become a better leader. I joined the program because I wanted to be in a romantic relationship and I thought that this training would give me the tools I desired. Even though I did end up getting a girlfriend as a result of my new found confidence, the true essence of the program was centered around becoming a leader of the 21st Century. This type of leader integrates elements of masculine and feminine leadership to become an embodied leader to create positive change in society.

As I dove deeper and broke through my mental barriers on why I didn’t want to be a leader for so long, it was clear to the people in my life that a new version of Andrew was emerging. However, it wasn’t as rosy as I wished as things at my company kept on getting worse and worse internally even as my leadership style was drastically improving from my vantage point.

Have you ever heard the saying that things get worse before they get better? That’s exactly what happened to me…..

Tensions continued to rise within my team. Whenever I received a daily call from someone, I could feel my blood boiling. I thought to myself, “Why can’t these people just be happy making good money working with NY Times Best Sellers?! What do they have to complain about?”

As I reflected back upon it, I realized that through my own lack of assertiveness, I had created a culture of entitled millennials. I hated to take responsibility for my results. I knew though, that the only way to right this ship would be if I decided to stand in 100% responsibility for my creation.?

In an attempt to right my wrong, I brought everyone together for an all hands on meeting to take ownership for my results and solidify what I was committed to moving forward to be an authentic leader that the firm deserved. Through my training at ALA, my coach supported me in crafting this speech and ensuring that it came from my heart. I stood in 100% ownership and attempted to enroll everyone with the new direction the company would be taking to ensure that it would be around for the next 7 years.

At the same time, we both agreed that this speech could potentially be polarizing to certain individuals at the company who had been undermining my leadership for months on end. There was the very real scenario that they would now subconsciously feel threatened by my reassertion of the leader of the organization and decide to part ways.?

Fortunately (in hindsight now that I’ve had some time to process the event) that’s exactly what happened. It unfolded in a manner that pushed me to the edge of my comfort zone and forced me to assert myself in a way that felt like my final exam while in my leadership training course.

Two individuals at the organization decided to join up in a negotiation against me to force my hand in a negotiation in which they believed they had enormous leverage over me. They believed that I didn’t know anyone else that could fulfill their duties if they weren’t at the firm. As a result of the enormous leverage they believed they possessed, they decided to come to the table with a list of one sided items they desired to be fixed. If they weren’t fixed to their liking, they would stop working at the firm and from their perspective, the company would be unable to fulfill its contractual obligations to its clients and would cease to operate.

From my perspective, this didn’t feel like a negotiation. It felt like I was being blackmailed to either hand over my company to them in the next 30 days or face a potential bankruptcy.

As I hung up from that call, I felt more anger rush through my veins than I had ever experienced in my life before. I felt betrayed. I felt vengeful. I felt embarrassed. And lastly, I felt the most destructive emotion possible: shame.?

In elementary school, I was known as the ‘smart kid’.?

In middle school, I was known as the ‘straight A student’.

In high school, I was known as the ‘overachiever’.

In college, I was known as the guy who always ‘had a clear direction for his career’.

And here was now….29 years old and potentially facing bankruptcy unless I fully stepped into my leadership power.

I thought to myself...

“You really F’d it up now Andrew. Way to go.”

“You should have just kept your mouth shut. This is what you get for asserting yourself.”

“It’s time to move back in with mommy and daddy. You were never meant to be an entrepreneur.”

“You’re not worthy of having this company. You deserve to let it be taken over.”

I allowed myself to wallow in these emotions of being a complete failure and letting down everyone in my life who once believed in. I let myself go all the way in my feelings of shame.

After I calmed down and stopped beating myself up, I decided to analyze my options with as little emotional reaction as possible to the chess game that I was in.

As I analyzed the situation and mapped out on paper what my options were, I had my ‘ah ha’. We had been recruiting for the last handful of months for our scaling efforts and I had a half dozen vetted individuals ready to go on projects if need be. I didn’t need to cave in to their demands. I had a path forward! As I looked deeper into the pros and cons of the scenario, I realized that my biggest risk would be if any of our clients felt more trust with them than with my organization. If that was the case, they would most likely end our contract and hire them directly in the near future.

This was a big risk though because I had been playing backseat driver for so long in my leadership. As a logical next step, I did what millennials do best...I scanned through YouTube attempting to find an inspirational video to give me the motivation I needed.

I stumbled upon a Gary V interview in which he talks about eating s&*^ to build a company and the importance of always playing for the long-term. It dawned upon me that this was the insight I needed most and it represented my options perfectly. With my new found desire to step into leadership for the first time in my life, I got to do what was necessary to save my company and commit fully to building an organization like I had always dreamed of as a naive college student. I was fully prepared to ‘eat s*(%’ for however long it took to rebuild my company under my terms. I was prepared to live in 100% responsibility for fulfilling my original vision of using business as a positive force for good no matter how challenging the ensuing 6+ months would be. I was prepared for no days off, credit card debt, terrible cash flow, clients leaving, etc. Whatever the world was prepared to throw my way, I was ready to face the challenge head on and do whatever it took to stay true to my vision.

With this relentless commitment to leadership, our new team, and clients, we embarked upon a new journey as an organization.?

The last few years of our new company direction has come with some of the highest highs and lowest lows as a business owner. We’ve onboarded some amazing new talent, we’ve lost some big clients that clearly didn’t trust me and we’ve created a unified vision together of the world that we’re aspiring to create.?

Leadership is not about your title, it's not about the power you have over others, and it’s not about the increased earnings. Leadership is about creating a powerful vision and enrolling other people into creating a better world with you. Along the way, these individuals step into their own power and confidence as well, thus creating a ripple effect of leadership. Leadership isn’t about you. It was, and always will be, about service to other people.?

However, before you’re ready to step into being of service to others and true leadership, it’s imperative to reflect on your own relationship to power. Are you doing this to stroke your own ego? Are you doing this out of fear and scarcity? Are you doing this to control others?

It’s so much better when it’s coming from service to a vision bigger than yourself.