Each time I get scared of taking a risk or I find myself in a critical junction, I always ask myself rhetorical questions; am I the only person who is faced with this issue? If not, how then do those people who have faced it overcome it? When you figure out people who have similar challenges as you do and how they overcame them, the next step becomes easy. It’s like fledglings that take their first leap of faith and jump off the cliff. They observe their parents, then one jumps and the others follow suit. In my case, there have been many precedents who have pivoted successfully. Thus, I calibrate my mindset that I am merely following a path that others have paved.

If I was to invent something that didn’t exist, it would be a different case as I would have nobody with prior knowledge to learn from or guide me. But many have had career pivots and found it to be fulfilling. Like starting my own hedge fund, I knew many failed but I focused on the successes. Why not me? I had a lot more reasons to answer “Yes” than “No.” This gave me the confidence boost I needed to resign from my cushy family office job, knowing very well that I may never get such a comfortable job again.

Our skills are a lot more transferrable than we think

For one, I would say that I possess very broad and useful experience, having worked for more than twenty years in fast-paced environments that fully utilized my skills. Above all, I started my own hedge fund at 30 years old at the depths of the financial crisis when I had very little. I think my work ethic, discipline, and ability to deal with setbacks and get out of my comfort zone are in the top few percent of the human population. A lot of people would think that the job experience in finance is not transferable and that is completely understandable. I mean I’m just a numbers guy, right? I’ve spent most of my time in front of a screen, thinking of how to make money by investing in businesses operated by others. What do I know about operating and scaling an actual business and leading people? But to be honest, the finance experience is very transferable. The truth is people who excel in finance are analytical, adaptive and hardworking go-getters. That already increases their chances of success in anything. Moreover, any successful business owner needs to understand concepts such as return on investments, return on capital, and return on effort; while this may seem like a piece of cake for those in finance, many entrepreneurs without finance background actually don’t understand them. This is something I never appreciated until I could look from the outside as a business operator and investor. Being a former investment banker and private equity investor, I learned to bring large groups of people together through the life cycle of deals. I believed I had an edge because I helped scale an auto dealership portfolio company during my private equity days. So going into the preschool industry, I had a hunch that all these experiences would be useful; the beautiful part of the whole experience was that as I deployed capital into preschools, I could continue my passion of investing while being my own boss on my own terms. That’s the freedom and purpose I yearned. More importantly, I was investing in myself by acquiring new knowledge and to see what life is like outside of finance. Thus, starting preschool was just another way for me to invest in a less conventional manner. In so many ways, I was doing everything I already enjoyed but in a more impactful and tangible manner. The icing on the cake for this second venture was that I did not have to use other people’s money. I simply made use of the wealth I accumulated and properly leveraged the skills I had built up over the years to pursue my goal.

One of the key reasons why I started preschool was so I could educate my kids exactly the way I wanted to. I didn’t want to send my kids off to another school to learn and live by someone else’s philosophy that I didn’t resonate with. I would run the school according to my own philosophy and on my own terms. Therefore, regardless of how this business turned out financially, I could treat this as a gift my wife and I would give to our kids.

Another thing people talk about when it comes to starting a business is the opportunity cost. Of course, you have to weigh what you gain and what you lose. How much money do I need to invest, especially considering the fact that I do not get a steady paycheck? Of course, I did not get a paycheck when I first started, just like when I launched my hedge fund. My wife had no income either. I had to risk my own capital to buy mom-and-pop preschools and build them into a corporation. While it wasn’t easy to take these risks, I recall I had bet on myself at 30 years old when I had a lot less. This time I was motivated by my child, passion for education and disseminating knowledge just as others had done for me. I can finally do something I deemed impactful that aligns with my life values. By replicating even a sliver of what I had done in private equity and applying my hedge fund investor mindset, I will be just fine. And I know by putting in the effort, passion and love for my child and her classmates, clients will endorse this business, and I will ultimately be rewarded financially. With this mindset, I was already a winner before I even started.