Get to know the team behind Second Street. Meet Zachary Kay, the founder & CEO of Second Street.
From his background in finance to his love of Costa Rica, here's a look at the man behind it all.
At Second Street, we talk a lot about Costa Rica, real estate, and mortgages. Behind all of that is a team of people doing something that's never been done before in this market.
Learn a little more about where they're from, what they do, and who they are. Today, we're starting with the person who started it all.
Happy birthday, Zach.
"From zero to one—bringing the gold standard U.S. mortgage to Costa Rica."
Zach Kay grew up in the South Bay of Los Angeles—weekends spent dirt biking, mornings spent on the beach learning to surf. A childhood defined by movement, curiosity, and exploration. Before most teenagers had a passport, Zach had already been across the globe traveling to countries like Hong Kong, Italy, Thailand, Mexico, Canada, and yes—Costa Rica.
He brought that curiosity to Georgetown University, where he studied International Political Economy and graduated Summa Cum Laude. From there, he earned a Master of Arts in International Business at Tsinghua University in Beijing as part of the inaugural class of Schwarzman Scholars—one of the world’s most selective leadership programs, founded by Blackstone Chairman Steve Schwarzman and designed to identify and prepare the next generation of global leaders at one of China’s most prestigious universities.
Then came finance. Zach spent three years as an Associate at Oak Hill Advisors covering media and telecom credit across leveraged loans, high yield, distressed credit, and special situations. He then joined Elliott Investment Management, one of the oldest and largest hedge funds in the world, with over $70 billion in assets under management. During his time at Elliott, he deployed more than $3 billion as a situational investor spanning equity activism, distressed credit, and private equity.
He saw what institutional capital could do—and what it hadn’t yet done for people buying homes abroad.
"Few things are more meaningful than seeing your company go from zero to one."
In 2023, Zach founded Second Street with a deceptively simple thesis: Americans buying or refinancing a home in Costa Rica deserve access to the same financial product they'd get at home—a 30-year, fixed-rate mortgage that’s safe, reliable, and transparent.
That product didn't exist in Costa Rica. So he built it. Today, Second Street is backed by a publicly-listed U.S. mortgage lender and has brought a level of trust and process to international lending that simply hasn’t ever existed before in Costa Rica. With a carefully assembled team, and real estate partners across the country, Second Street has become Costa Rica's leading international mortgage lender, now serving both Americans and Canadians. In just over a year of lending, Second Street has helped dozens of clients borrow tens of millions of dollars to make their Costa Rican dreams a reality—with a pipeline of over $100 million more.
When Zach isn’t building Second Street, he’s betting on others. He’s an active angel investor with a focus on finance, media, and enterprise AI. He's also a Partner at Litquidity Ventures—an early-stage fund built around the massively popular Litquidity brand, one of the most followed finance communities on the internet, with over 1.6 million followers across Instagram and X. The fund backs founders at the pre-seed through Series A stages across fintech, consumer, and enterprise software, with a particular edge in connecting startups to a uniquely engaged, finance-native audience.
🎿 A committed skier and Ikon Pass loyalist, Zach can't quite decide his favorite resort between Snowbird (better terrain) and Brighton (better vibes—a little pura vida).
🏄 He's relearning to surf after growing up on the LA beach—turns out it's harder the second time.
🔥 His signature grill move: salmon with dill and labneh yogurt, best enjoyed on a summer evening.
🥾 A hiking enthusiast—he once completed a four-day trek in Norway. Ask him about the fjords, getting lost, and the Russians with GPS who helped him.
🌎 His first trip to Costa Rica—the country that would become the center of his professional life—happened on one of those early family adventures his mom organized when he was a kid.
🏍️ Dirt biking with his dad as a kid in the California deserts remains one of his favorite memories.
🧘 On his first date with his now-girlfriend, he talked about buying a yoga retreat in Dominical. Turns out, there was no financing for foreigners available at the time. He later fixed that problem.
Zach built Second Street so that buying a home in Costa Rica could finally be simple. If you're ready to get started, we'd love to hear from you.
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