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A couple started buying real estate to free themselves from 80-hour workweeks. After scaling to more than 100 units, they work part time and travel half the year.
Letizia Alto and Kenji Asakura started buying investment properties together in 2015. For years, they worked 80-hour weeks in the hospital and wanted to buy back time. They scaled to over 100 units, hit financial freedom, and now teach other doctors how to do the same. At the height of their medical careers, Letizia Alto and Kenji Asakura had to block off time on their calendars if they wanted to see each other. "We would schedule out a month in advance, days that we could spend together because it was so busy," Alto told Business Insider. "And this was without us having kids together." They were each working more than full time as hospitalists, logging 80-hour weeks. When they took a step back and considered what they wanted their future to look like, the grueling workweeks didn't fit in. "Kenji asked me: 'What do you really want for your life? Presume there are no limits. What would you want to do?'" recalled Alto. Her answer was specific: She wanted to spend months out of the year in Italy, producing olive oil and hosting friends. "And that was obviously very different than the path we were on." It was an interesting thought experiment that ultimately shifted their mindset. About six months later, while traveling in a camper van through New Zealand on their honeymoon, they passed the nights reading what Alto had recently downloaded to her Kindle — "Rich Dad Poor Dad" — and some of the author's core themes resonated. "It was really powerful. We were like: 'Oh, my gosh, this is it: We're employees, we trade our time for money, we're never going to be able to be in Italy for three months at a time because we're always going to have to be working,'" Alto said. "This future that I had kind of visualized six months before didn't work. The only way it works is if we have another source of income, outside medicine, that can replace part of our salaries so that we can have the freedom to take time off." The couple decided right then and there that when they returned home to Seattle, they'd start investing in real estate. Putting off a primary residence to buy investment properties Creating additional income by investing in real estate made sense for Alto and Asakura for a few reasons. One, Asakura already had experience. His parents were investors and, as a kid, "I remember going to rental properties, picking up checks, seeing my dad talk to tenants, things like that," he said. "I grew up with real estate, and pretty much as soon as I had money, I started investing." That came after medical school, when he worked as a management consultant for McKinsey & Company for a few years before completing his residency. Using savings from his salaried job, he and a friend started building a joint portfolio in the early 2000s and, like most property investors at the time, made a lot of money. "Real estate just appreciated like crazy, all the way up to around 2006, 2007, when things started slowing down," said Asakura, who was mainly buying and flipping land. "I'd buy a piece of land for like $100,000 and, six months later, I would sell it for $300,000. It was that crazy. It was just like 'The Big Short.'" When the recession hit, "my properties didn't cash flow, and I got stuck with a lot of mortgages, insurance payments, and property taxes. I was pretty much upside down on my properties," he said. The experience didn't deter him from reentering the real estate world years later alongside Alto. "I wasn't scared. If anything, I had confidence just because we had a plan. Mistakes are an expensive education, but it's the best education." In addition to Asakura's experience, the couple had the capital to invest in property. They'd planned to buy a primary home together and had already set aside cash for the down payment. But, after returning from the New Zealand trip in early 2015, they asked their agent to switch gears and help them find a rental property. They had a new, clear vision. "We wrote down our portfolio goal," Alto said. "We were like, we're going to own this many units and we're going to make this much cash flow." Buying and holding cash-flowing properties When Alto and Asakura started purchasing investment properties, their strategy revolved around two main principles: cash flow and forced appreciation. They use a cash-on-cash calculator that allows them to input metrics such as purchase price, expenses, and projected rents to predict a property's performance. They're less interested in how it's performing under the current owner. "What's really more important is knowing how it's going to run after you're done with it," Alto said. "We regularly buy properties that are negative or have really low cash-on-cash returns with the current owners. What we see is the potential for what it can become." They learned from Asakura's early investing days to never rely on market appreciation. They'd rather force appreciation on the property through improvements and upgrades, which isn't dissimilar to a flip, he said: "The difference is, a flipper sells, whereas we're holding. The other difference is that a flipper typically buys a property that'll never cash flow, whereas we're buying properties that are good flip projects but also cash flow." In 2015, using their down payment savings, they bought two duplexes outside Seattle, filled the units with tenants, and started generating rental income. They continued buying small, undervalued multifamily properties, used tax strategies to shield their income from taxes, and rolled their rental income, savings, and tax refunds into more properties. By 2017, they said, they were bringing in over six figures of rental cash flow. The next year, they started their blog, Semi-Retired MD, which would evolve into an online course specifically geared at doctors and high-income earners looking to invest in real estate. By 2021, they owned more than 150 personal units, and they partially own hundreds of other units through a handful of syndication deals. BI confirmed their property ownership, which consists of multifamily properties, commercial properties, and the syndication deals, by reviewing deeds and operating agreements. The couple were tenants themselves up until 2022, when they moved to Puerto Rico and bought their first primary residence together. They were never chasing big cash flow goals to sit on the beach all day. "Our goal was to buy ourselves time-freedom and to continue to contribute to the world and have purpose," said Alto, who worked in the hospital up until 2020 and now spends a chunk of her days running Semi-Retired MD. Asakura, who scaled back to part time in the hospital in 2015 to focus on real estate, spends his days managing their portfolio, and they now have more time to dedicate to each other and their kids. "I think about what my life could have been right now: driving to work, spending 12 hours away, and coming home late at night when the kids are asleep," Asakura said. "That's not how our lives are." Alto added: "We have our kids homeschooled. We travel six months a year as a family. We hang out with our kids in the mornings, we see them for lunch, and we see them for dinner every night. We never would have had any of that freedom." This story was originally published in June 2025. Read the original article on Business Insider
