Traditional hospitality groups have long focused on operations. But few have leaned into what today’s traveler actually craves: a unique, memorable, Instagram-worthy experience. That’s the gap Jacobo Hernandez recognized early—and turned into an unfair advantage.
“The modern traveler is willing to pay a premium for something that feels special,” Hernandez says. “They want connection, design, and something worth sharing. Most hotel owners are still thinking about pillows and paint colors. I think about what drives someone to stop scrolling and actually book.”
This marketplace-first mindset stems from Jacobo’s entrepreneurial roots. By his late 20s, he had already built and sold two companies: an e-commerce brand he launched at 22 that generated multiple millions in revenue, and a portfolio of short-term rentals that caught the attention of private equity investors.
He spotted the rise of wellness- and design-focused travel well before it became mainstream. Today’s traveler isn’t looking for another bland room with white sheets and beige walls—they’re seeking soul. They crave properties with character, history, and a story to tell. From reimagined castles and converted churches to retro motels brought back to life, every space needs to feel one-of-a-kind. The modern guest wants to wake up somewhere that feels unforgettable—not interchangeable.
It’s not just about how it looks—it’s about how it feels. Guests want cold plunges and saunas, firepits under the stars, hot tubs with a view, pickleball courts, cozy reading nooks, and thoughtful design that invites them to slow down. The modern traveler craves memorable experiences, and they’re willing to pay more for places that leave a lasting impression.
But his sharpest insight may have come from a demographic turnaround: millions of baby boomers are retiring, and many of them own outdated hotels and motels in top tourist markets. “These are generational assets in A+ locations,” Jacobo explains. “But the owners are tired. They haven’t kept up with amenities, design, or digital marketing. That’s exactly where the opportunity is.”
Now, Jacobo is acquiring and redeveloping these overlooked properties—turning them into boutique hotels built for today’s traveler. He’s not just following a trend. He’s influencing the future of hospitality by applying marketplace principles to physical spaces.
From Selling Wedding Gifts to Buying Hotels
The e-commerce business Jacobo Hernandez built in college faced intense competition—especially from copycat sellers who duplicated his wedding gift products and undercut his prices. In response, Jacobo went deep into digital marketing and data analytics. He became an incredibly avid student of online behavior, mastering everything from SEO and Amazon’s algorithm to conversion rate optimization and customer psychology.
By studying Amazon’s search ranking factors, he uncovered patterns in buyer behavior that most sellers completely overlooked—and it paid off.
Later, he realized those same principles applied to real estate. Airbnb’s property rankings, he observed, mirrored Amazon’s algorithmic logic: visibility, relevance, reviews, and click-through rates all influenced bookings. That insight became his entry point into short-term rentals. He developed a methodical, data-driven approach to acquiring and managing properties, one designed to win.
The strategy worked. His growing portfolio of high-performing properties attracted attention from the investment community, ultimately leading to a successful exit via private equity acquisition. The deal gave him both the capital and the conviction to scale into boutique hotel ownership—where he’s now applying those same digital-first, analytics-powered principles to disrupt an industry still catching up.
Passport Stamps That Pay Dividends
Travel changed Jacobo Hernandez long before he entered the hospitality business. Educated at the International School of Lausanne in Switzerland and later at the University of Miami, his worldview was shaped not just by academics—but by immersion. Jacobo has traveled to over 40 countries and stayed in hundreds of hotels, each one offering a new opportunity to study what makes a guest experience unforgettable.
“I’m constantly on the lookout for the best ideas when I travel,” Hernandez says. “From Japanese onsen spas with tranquil gardens to beachfront hotels that embody effortless luxury—every stay gives me something new to bring back to my properties.”
That global perspective has become his competitive edge. His team takes a user-first approach to renovations—analyzing how guests actually move through and interact with spaces, rather than relying on assumptions. Small adjustments to layouts, amenity placement, and flow have led to major improvements in guest satisfaction and revenue per stay.
Building More Than Just Buildings
Every detail in Jacobo Hernandez’s properties is mapped out with care. His years in e-commerce taught him that small adjustments in presentation and usability can drive massive results—and now he applies that same precision to physical spaces.
But Jacobo brings more than just design sensibility to hospitality—he brings digital dominance. With deep expertise in SEO, split testing, conversion rate optimization, influencer marketing, and algorithm mastery, he consistently beats the competition on platforms like Airbnb. His listings don’t just look good—they’re engineered to rank higher, convert faster, and rebook more often.
“I see buildings the way I used to see online stores,” Hernandez explains. “It’s all about testing, tweaking, and optimizing every detail—from the layout to the listing title.”
He also integrates AI into management and operations, streamlining everything from guest communication to maintenance workflows. His approach is lean, tech-forward, and always evolving—he’s constantly looking for new ways to apply the latest tools to enhance guest experience and business performance.
Instead of treating short-term rentals as temporary accommodations, Hernandez crafts stays that feel purposeful and memorable. His properties routinely earn top-tier reviews, attract loyal guests, and outperform comparable listings in their neighborhoods.
He brings that same strategic edge to his voice as a business educator. His book, Short-Term Rental Secrets, outlines the exact framework he used to scale and sell his first real estate portfolio. On his podcast, he shares candid conversations with top investors and entrepreneurs, bridging the gap between day-to-day execution and long-term freedom.
The Next Venture
Jacobo Hernandez built his foundation in e-commerce pretty young, mastering the art of digital strategy and created a seven-figure brand by understanding how platforms work beneath the surface. He carried this knowledge into real estate and is currently excelling, with lots of years ahead of him to achieve more.
Hernandez will continue to identify overlooked properties in high-growth markets and turn them into iconic destinations. His focus remains on staying lean, preserving the integrity of each project, and delivering results that combine investor returns with guest satisfaction. His goal is not just to grow his portfolio but to raise the standard for what hospitality can be in a digital world that increasingly values quality, story, and intent.
