Introduction

Most people that find themselves in a leadership role want to do something awesome and be impactful in the world. The funny thing about leadership is that it’s hard; real leadership goes against most of the instincts that kept us alive before the modern age. The hard truth is that leadership isn’t about you. Great leaders put their personal agenda aside to ensure their team members succeed first. If you are playing for your own success, you are a BOSS, not a leader.

The other thing about leadership is that being a boss is way easier than being a leader. Bozos get promoted every day; hard-hitting assholes are celebrated by Wall Street and Hollywood. So why do you want to be a leader? Because leaders change things; they push the human race forward. Leaders inspire those around them to reach for greatness. And leaders prove that extraordinary leadership does not require official authority, it simply requires that we put the prosperity of our stakeholders first.

Leadership is messy and involves making mistakes, which can turn into the greatest growth opportunities. Rarely will you learn something from a good decision, because you got lucky with your first guess. You learn when you get it wrong and have to acknowledge, analyze the situation, and guess again. And the cycle repeats. Learning from mistakes involves allowing your preexisting beliefs to be challenged. “This is how we have always done it” works when it’s working, but not when you aren’t getting the results you want. The first step to becoming a great leader is to celebrate your mistakes and those of your team members and learn everything you can from them.

While leadership is hard and you will learn the most from your and your team’s mistakes, this book is intended to make that gap smaller for you. If you’re trying to build a company, build an organization, keep up with the innovation required to be competitive today, or just trying to change the world, you’re going to make mistakes. My goal is to share mine with you, so you don’t have to fail as many times as I did to become the effective leader you aspire to be. In the pages that follow, I will share my train wrecks, my lessons learned, and my triumphs. Please make sure your seat belt is securely fastened and your tray table is in the upright position.

My Early View of Leadership

I grew up in a pretty tough neighborhood as an outcast. I was one of five white kids in a gangland neighborhood of Los Angeles and was only five years old when I saw my first murder. My parents separated, and my dad moved to Colorado. I hated school from the fifth grade on and finally dropped out of high school in the eleventh grade to join the Navy and see the world.

I was in the Navy six years, two months, and twenty-three days, and I was wildly successful. I spent nine months in the Persian Gulf during Desert Shield/Desert Storm and received a Navy Achievement Medal for Leadership. After the war, I volunteered for anything and everything. My motto was “say YES!” One of the highlights was when I became a rescue swimmer, because the search and rescue school has the second highest attrition rate of all the special forces. My only motivation to go to SAR school was to see if I could get through it. When I graduated, I remember thinking, I can’t believe I did it!

As I transitioned into corporate America, my view of leadership was founded on the power paradigm of gangland leaders, naval officers, and what I had seen watching actors on television and in movies. Top Gun. Rambo. Wall Street. I thought these were leaders. They gave orders and people followed them. It wasn’t until much later that I realized these people weren’t leaders at all. They were bosses, and they succeeded at the expense of other people or by dictating their actions.

When I transitioned out of the military, I went to work at Universal Studios in tech support. Within a year I was promoted to director and was tasked with managing national technology rollouts. I was there four years and wrapped up my tenure by rescuing their global Y2K project. I took over the project in March of 1999, with only nine months left before the New Year, and the team in place was still only in planning mode. My team had to touch every piece of technology in over 127 offices worldwide, including the theme parks. This included computers, data centers, and even the equipment that controlled the roller coasters.

We completed the worldwide remediation efforts in November of 1999. The project was a success, and I wanted more! I had been working with project managers from some of the largest global consulting firms, and I found that I had to teach them how to do their jobs. They were billing Universal $200 per hour for their services and I was on salary at $80,000. It was clear there was demand for a project management firm that could deliver results, so I started one. My goal was simple: I was going to be the best in the business and make tons of money.

Growing a Company…the Wrong Way

When I first started my project management firm, 120VC, I was the only employee. For the first couple of years, that was exactly what I wanted. As time went on, my clients started asking me to take on more and more, to the point where I had to start saying no. I was already working sixty- to eighty-hour weeks and didn’t think I could continue to be successful if I increased my workload.

As most of you know, saying no is a bummer. According to William Ury, “no” is one of the hardest things for most people to say. Instead of continuing to say no, I decided I was going to start a real company and start hiring employees. So I started telling my customers I could bring in other consultants that would deliver “just like me.” They were skeptical at first but needed the work done, so after five years of working independently, I took on my first staff member.

I didn’t know it at the time, but I had lied when I said they would deliver “just like me.”

As I started to expand, I required my staff to come to me for every decision because I believed I was the best at what we did, and it was my name on the door. To an extent, I was the best at what we did, and customer fulfillment was important to me. I had promised my clients that as I hired other people to take on their projects, my staff would continue to exceed their expectations just like I did.

That was naïve, and I essentially lied to them. They didn’t know it, and the lie wasn’t intentional; in reality, though, it’s impossible to duplicate yourself. Believe me, I tried. As I hired people it was my way or the highway. I trained them to come to me for every little thing until my time was now at capacity again. I woke up one morning with five conflicting thoughts: I had achieved my goal, I was one of the best in the business, I made a ton of money, my job was a total grind, and I was the architect of my own situation.

I called an all-hands meeting and shared how I was feeling with my team. I encouraged them to tell me what sucked about 120VC—the best and worst decision I had made to that point. It was the best decision because they told me; they gave me the opportunity to hear them and make the company a better place to work. It was the worst decision because I was entirely emotionally unprepared to listen to my staff tell me how ugly my baby was.

I had reached a point in the development of the business where I knew even though I was smart, capable, and good at what I did, I was the only one coming up with new ideas. Therefore, the company was only as smart as me. My leadership style required a shift. I had to figure out how to live up to my client commitments, scale the business, work with my staff, help them make decisions, and still have the company go in the direction I wanted it to go. The task seemed daunting. How could I let everybody make decisions and still stay in control? The answer was simple: I couldn’t. I was still a boss; I wasn’t yet a leader.

Leaders help their team self-actuate a roadmap to a shared goal. They believe everyone is equal and enlightened. You can’t fake this. You have to truly believe that even if someone doesn’t have the same IQ or isn’t as accomplished as you are, they are truly your equal. You don’t have to be a genius to be an innovator, and you don’t have to be a thought leader to be capable of great things.

As you can imagine, my company and I didn’t transform overnight. When I asked my team to start making decisions autonomously, they didn’t trust me immediately. In fact, they responded to my demand to “bring solutions instead of problems” by bringing multiple solutions without any opinion on which would be the best to solve the problem they faced. They wanted me to decide. I realized later that the bigger problem was that I had hired people that didn’t want to take responsibility. They wanted a boss and I had hired these people because I was a boss.

My biggest lesson from that time was that leaders don’t really create a culture, we hire it. I was a boss, so I screened for smart, capable people that I thought would do what I said. When I decided to be a leader instead of a boss, I...