Doctors Leave Careers to Invest in Real Estate for Family Freedom

SEATTLE, Wash. — At the peak of their demanding medical careers, Letizia Alto and Kenji Asakura found their schedules filled just to spend time together. Each worked as hospitalists, with schedules exceeding 80 hours a week. “We would schedule out a month in advance, days that we could spend together because it was so busy,” Alto told Business Insider.

Facing a future that did not align with their personal goals, the couple re-evaluated their lives. “Kenji asked me: ‘What do you really want for your life? Presume there are no limits. What would you want to do?'” recalled Alto. She dreamed of several months in Italy, producing olive oil and hosting friends. This vision starkly contrasted with their current lifestyles.

During their honeymoon in New Zealand, they encountered a realization that altered their future. “It was really powerful. We were like: ‘Oh, my gosh, this is it: We’re employees, we trade our time for money,'” Alto said. They concluded that in order to pursue their dreams, they needed an alternative source of income beyond their medical salaries.

When they returned to Seattle in 2015, they decided to invest in real estate. Asakura, who had experience thanks to his investor parents, felt confident venturing back into the market. “I grew up with real estate, and pretty much as soon as I had money, I started investing,” he said.

After the 2007 recession impacted his initial investments, Asakura learned valuable lessons but remained undeterred. “Mistakes are an expensive education, but it’s the best education,” he stated. The couple had cash saved for a down payment and shifted their focus from buying a primary home to acquiring rental properties.

“We wrote down our portfolio goal,” Alto shared. They aimed to own multiple properties generating sufficient cash flow. Their strategy centered on cash flow and forced appreciation. Utilizing a cash-on-cash calculator, they assessed potential property performance, favoring those with improvement opportunities.

In 2015, they purchased two duplexes just outside Seattle, rented them out, and began earning rental income. Their method involved buying undervalued properties and employing tax strategies to reinvest profits into additional real estate. By 2017, their rental income exceeded six figures, enabling them to share their journey through their blog, which later became a course designed for high-income earners in real estate.

By 2021, Alto and Asakura owned over 150 rental units and participated in numerous syndications. They transitioned from tenants to homeowners in Puerto Rico by 2022, enjoying more family time thanks to their successful investments.

Asakura reflected on his past life, stating, “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. 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.”