I traded investment banking for vacation rentals to be a good dad: A Personal Journey
In a world where success is often measured by the size of one's bank account and the prestige of one's job, I made a bold decision to walk away from a lucrative career in investment banking to pursue a different path. I did this to be a better father to my children and to have more time with them. This is my story, and it's one that I believe will resonate with many parents who have to make difficult choices between their careers and their families.
The Investment Banking Life
My journey began in the bustling city of San Francisco, where I was born and raised. My parents worked tirelessly to provide me with a good education, and I went on to study at UC San Diego and Cornell's Business School. I started my career as an insurance adjuster and eventually landed a job at a proxy research firm, Glass Lewis, which was my gateway to investment banking. I was hooked on the fast-paced, high-pressure environment and the financial rewards that came with it. I worked on multi-billion-dollar deals, flew business class, and stayed in nice hotels. But as I rose through the ranks, I began to realize the toll it was taking on my personal life.
The Realization
After getting engaged to my wife, Elizabeth, I started to question whether I could be a great banker and a great father at the same time. I saw how disruptive the career could be for my colleagues' families, with kids in boarding school and spouses in different states. I remember thinking, 'That's the job. That's what it asks of you if you want to win in this business.' I didn't want to be the guy who made that trade.
The Side Hustle
To build a business that could eventually give us more control over our time, Elizabeth and I started renting out apartments and listing them on Airbnb as a side hustle. We kept growing that business, and eventually, after a year and a half of sacrificing nights and weekends, I was ready to quit my job in 2018. It was a difficult decision, and some people at work looked at me like I had three heads when I told them why I was leaving.
The COVID Bump in the Road
The biggest bump in the road was COVID. After everything shut down, we lost all of our bookings but still had to pay rent on our apartments. For a moment, it felt like the business we had been building for years was over, and I might have to return to banking. But we rebuilt, and later that year, we bought our first property in the Smoky Mountains of Tennessee to take advantage of the short-term rental tax benefits. We now have eight homes in our portfolio.
The Mentorship Business
After getting so many questions about how I got out of banking while living in New York with two kids, we started a short-term rental mentorship business in 2023 called STR like the Best, along with a podcast. We've since helped over 100 of our clients purchase an investment property. This business has allowed us to help others achieve their financial goals while also providing us with the flexibility to spend more time with our family.
The Personal Freedom
Now, a decade later, I have a portfolio with eight homes, a growing mentorship business, and two children whom I get to spend more time with than ever. I never could have done this as an investment banker. I would have dropped them off, given them a hug, and then not seen them for two months. My parents are older now, and I can spend more time in San Francisco to help take care of them. I see it as a small way to pay back what they did for me.
The Takeaway
In the end, I made a choice that many parents can relate to. I chose to prioritize my family over my career, and I believe that it was the right decision. I miss the intellectual firepower of colleagues and the clients I worked with, but I also know that my kids, my wife, and my family will miss me more if I don't make this choice. As Keanu Reeves once said, 'I know that the ones who love us will miss us.' And that's a truth that I hold dear.
