When I was 25, I quit my job at Goldman Sachs. I left Wall Street, and I used what I had scraped together to buy a controlling stake in a struggling technology company.
When I acquired the business, it was on the brink of failure. There wasn’t enough cash to make payroll in two weeks, and the company’s finances were a train wreck. But I dug in and put in long hours and tons of travel away from home. I learned everything there was to know about that company. It took a long time and a lot of hard work, but that work would prove fruitful. Over the next few years, I rebranded the company, grew into several new product lines and started applying some of that Wall Street knowledge to both acquire new business units and eventually sell the original core business altogether, thus pivoting into a software-as-a-service company.
I kept growing the business, building the team and expanding. But, after several years at the helm, I realized I needed to make a change. It sounds amazing to be the CEO of your own company before 30 years old, but I started to see that what the company needed to grow, what I wanted to do and, most importantly, what my core skills were, did not align.
My core skill set is not running and managing companies. I put together successful deals to buy these companies. I help them make big, strategic pivots and navigate tough business decisions. My core skills are in big-picture strategy and mergers and acquisitions.
But what I don’t like doing, and what I’m not any good at, is slogging through meetings, keeping track of direct reports and the daily grind of managing a team. As a result, we had a great strategy, but the execution suffered. I needed to find what renowned business growth expert Gino Wickman calls an “integrator” to complement my big-picture strategic focus.
It all happened one morning when I was having coffee with an old friend of mine. He was running a related technology business at the time and felt stuck as well. Almost on a whim, I threw out a wild idea: What if you took over my job? We both felt it might just be crazy enough to make sense.
We spent months hashing out what it might look like, and eventually, we landed on a potential path for both of us. He would step into the company as CEO, and I would step into the role of Chairman of the Board.
That was nearly three years ago, and since then, the company has taken off on a new trajectory. Its growth has skyrocketed. and we’ve landed on the 2019 Inc. 5000 list of the fastest-growing companies in the U.S. It’s amazing what can happen once you get aligned with where your skills can really shine and get the right people on the bus.
I learned four life- and business-changing lessons through that journey that I want to share with you.
1. Self-awareness is a secret weapon. Self-awareness is one of the most important skills you can develop as a business leader today. Tasha Eurich, who has a Ph.D. in industrial-organizational psychology, called self-awareness the “secret weapon of the 21st century” because without it, you’re stuck. If you don’t know where you are, how can you improve at anything? Self-awareness is the biggest requirement to be a successful leader, entrepreneur and businessperson. Without self-awareness, you’re shortchanging your ability to communicate, influence, deal with change and shape your company.
2. Always replace yourself. One of my business mentors taught me this lesson: Always work to replace yourself. Good business people are scared to replace themselves because they might lose their job. Great business people realize that the only way to scale up and grow is to replace yourself constantly. This is one of the biggest lessons I learned from studying some of the most successful business people of all time. It’s also a cornerstone of the skill of high-leverage thinking. If I hadn’t taken the leap of replacing myself, I would be stuck doing a job I didn’t want to do and wasn’t good at, and my company would be leagues behind where it is today.
3. Make tough decisions, even when you’re unsure. There were a dozen or more inflection points on my journey where I made a tough decision when it was impossible to know for sure if it would work out, such as quitting my job at Goldman Sachs, selling off the core business off the company and firing myself as CEO. Too many leaders and entrepreneurs get paralyzed by the need for certainty that they are making the right decision. In an uncertain world, the real skill is getting comfortable with uncertainty and making a decision anyway, even when you aren’t sure what will happen next. That lesson holds true in everything from high stakes poker, to Wall Street trading and even going blind in outer space.
4. Know what’s holding your business back. Management expert Peter Drucker is known to have famously said, “The bottleneck is always at the top of the bottle.” Sometimes, the biggest barrier to your business’s growth might just be you. There’s endless content out there on every business concept you can imagine, but the one subject that is almost categorically neglected is the importance of psychology and self-awareness.
I still practice them and help the companies that I buy and work with do the same today.