In 2020, after pouring my heart and soul into my video production company and realizing I actually didn’t want to be a full-time CEO and sell my company to a larger agency, I actually just wanted to create cool things and help people, I had reached a stage of burnout. I had started traveling a lot on 2018 to try and revive my inspiration for the company, and I rented out my own apartment while I traveled. I loved the stable income it provided for doing much less than what it took to run a production company, which required me to keep reinvesting capital. I discovered (the then blog) Bigger Pockets, and the door to real estate investing started to crack open.

In the meantime, I focused my energy on producing videos that lit me up: Family Legacy Videos, which give people who are getting older the space to reflect and tell their life stories on camera so their history and the lessons they learned can be passed onto their families for generations to come. One of these interviews was with a mega-wealthy real estate tycoon in the Bay Cities who arrived in this country a penniless immigrant and remained as humble as the day he arrived. He lived a life of integrity, a life of fun parties and family yacht trips on the Mediterranean in his personal yacht, which he kept docked in front of his home. He spent a good amount of his fortune giving back to those who were less fortunate, and in his later years, he became more spiritual. He and his wife exuded humility, love, and joie de vivre. This is the kind of life I wanted to lead.

During his interview, he said that he stumbled into real estate investing with no more than an 8th grade education, when he left school to start selling wholesale flowers on Santa Monica Blvd. He started in multi-family real estate, but his dream was to open a luxury hotel where he could could make what he was making in month in one of his rental units in a night or two at a luxury hotel. He eventually opened one of the most luxurious hotels in Beverly Hills. In that moment, a seed was planted. I thought, “If he can do it, surely I can do it.” But I decided to skip the multifamily racket and go straight to building a portfolio of luxury rentals serving people like me: people who love to travel and work comfortably from the most beautiful places in the world, and people who are relocating and looking for a perfect home base from which to build the rest of their lives.

I had come to the realization that a service-based company would always be declining in value unless I kept taking big financial bets, and it could fall apart relatively quickly. Real estate, on the other hand, would give me the ability to build equity in an asset while receiving cash flow from it as a business, and you didn’t have to be a genius to do it. So I built a portfolio of luxury rentals using the money I had made from my company (which I had diligently dollar-cost-averaged into a very unsexy mutual fund over the previous 10 or so) and some very creative financing.

That real estate portfolio has provided me with financial freedom to spend my time on what I love most: helping other entrepreneurs, founders, and executives achieve their goals in a way that brings them true success, however they define it.