For Ryan Porter, a 25-year technology veteran currently working with AWS, real estate investment has grown from an opportunistic side project into a calculated cross-border operation. As a Principal at Porter Legacy Group, he has developed an approach to real estate that pairs lifestyle flexibility with steady returns through mid-term furnished rentals. Based in San Francisco with time split between California and Medellín, Colombia, Porter continues to refine this strategy while expanding his portfolio.
Porter’s entry into real estate came during the Global Financial Crisis when he purchased a fixer-upper in San Francisco’s Mission District. “I got a good price on it and over the years, I have remodeled it twice,” Porter explains. “First doing some more surface level stuff painting, and probably about eight more projects. And then slightly more recently, about five years ago, I did big stuff – the kitchens and bathrooms, and also laid down a floor in the attic.”
Porter’s strategy centers on mid-term furnished rentals, targeting digital nomads and professionals temporarily relocating to new cities. This approach occupies a strategic middle ground between traditional long-term leasing and the more management-intensive short-term rental market.
“The Airbnb space has a lot of turnover, and it can be hard to manage,” Porter notes. “With mid-term rentals, I tend to find that you get a digital nomad or someone that’s being moved into a city for a period of time, and they treat it much more like home.”
Porter’s market selection process draws heavily on his personal experience and analysis of digital nomad migration patterns. Rather than relying solely on traditional market metrics, he targets locations where he sees alignment between professional opportunities and lifestyle appeal. Beyond his established presence in San Francisco and Medellín, he’s evaluating markets like Mexico City and Porto, Mexico, based on their increasing draw for remote workers and digital professionals. His methodology combines extended stays in each potential market with careful tracking of his target tenant demographic’s movement patterns.
Expanding into international markets presents distinct financing challenges, as Porter discovered in Medellín. “You can’t go to Medellín and get a loan,” Porter explains. “Only 10 or 20% of the properties have mortgages” in Latin America. To address this, Porter activated equity from his San Francisco properties through a HELOC to fund his Colombian investments. This financing approach enabled him to renovate three properties in Medellín, selling two and holding one, while maintaining his San Francisco portfolio.
His success in new markets stems from building strong local partnerships and implementing systematic property management approaches. “I partnered with a local law firm there. I was friendly with a husband and wife team that was an architect designer. They’ve done all my work in Medellín,” Porter shares. He maintains detailed documentation of operations and relationships with service providers in each market, managing everything through simple but effective systems using Google Drive.
Porter is now setting his sights on larger-scale opportunities. He’s dedicated the past year to studying multifamily investments, particularly in the Dallas-Fort Worth area, where he’s targeting opportunities in the 100-unit range. “After having done single family remodels here for a while, it’s just a lot of work with kind of limited upside,” he reflects. “I’m focused more as an investor and looking for return on investment and really building generational wealth.”
His progression from opportunistic investor to cross-border real estate strategist demonstrates how methodical market analysis, strategic partner selection, and systematic operations can build a portfolio serving both lifestyle and investment objectives.
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