
Episode #27
The $100 Website That Led to a Fintech Company: Inside Aloha with Rodrigo Romero
What happens when a self-taught 14-year-old hacker from the Dominican Republic grows up to rebuild the payments infrastructure for an entire industry? On this episode of Beyond the Bottom Line , Miguel sits down with Rodrigo Romero, founder and CEO of Aloha, a Miami-based fintech company building the banking and payments infrastructure powering the future of travel across the Americas. Rodrigo's path started far from fintech, building his first $100 websites in Yahoo Chat rooms, landing a $2,000 client at 14 without knowing how to build what he'd just sold, and eventually co-founding Aloha with Jorge Dupri after Jorge's own boutique hotels kept losing bookings to cross-border payment friction. What began as a software play quickly became something bigger: a platform solving the real problem underneath it, moving money seamlessly across countries and currencies for travel and hospitality businesses. In this conversation, Rodrigo breaks down why travel is one of the least "tech-touched" industries around, how Aloha protects both merchants and travelers from fraud and chargebacks, and why compliance can never be an afterthought in fintech. He also gets candid about the hardest pivot of his company's life, when the software layer they built to bootstrap the business started outgrowing the payments business it was meant to support and how he uses AI agents (not chatbots) to run reconciliation, investor outreach, and even serve as a sparring partner for his own blind spots. In this episode: How a Packard Bell computer and a printed HTML manual sparked a fintech career Why "just get a customer" beats perfecting your product The real problem Aloha solves: payments, not just software How Argentina's currency tax changes are reshaping cross-border travel spending Using closed-loop AI agents instead of prompt-and-wait AI Why onboarding is a non-negotiable leadership principle What to look for in a co-founder (hint: not someone just like you) About Our Guest Rodrigo Romero is the founder and CEO of Aloha, a Miami-based fintech company building the payments and banking infrastructure powering the future of travel across the Americas. Alongside co-founder Jorge Dupri, he founded Aloha to help travel and hospitality businesses simplify cross-border payments, access local banking services, and move money seamlessly across countries and currencies. Learn more about Aloha, or connect with Rodrigo on LinkedIn . Connect with Miguel Connect with Miguel on LinkedIn or reach out at media@centurionfirm.com .

