Cover Story: Joshua Rappaport’s Journey of Resilience and Success

February 3, 2025

Joshua Rappaport - Photo by Oscar Almeida

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When it comes to wearing multiple hats—both in his personal and professional life—Joshua Rappaport doesn’t shy away. From managing two businesses to finishing multiple marathons around the world, he’s no stranger to maintaining an active lifestyle.

Born and raised in Toronto, Canada, he attended the University of Toronto before participating in an exchange program at the University of Guadalajara in 2003. After completing his degree, 23-year-old Rappaport traveled across Mexico for about six months before eventually settling in Puerto Vallarta, where he began working in the hospitality industry.

It was there when, through networking, Joshua received an invitation to work as a mortgage broker, marking the beginning of his real estate journey. Today, he owns and manages two companies: RE/MAX Romantica, a real estate agency, and Cross Border Investment (CBI), which offers mortgage and legal services for clients purchasing properties throughout Mexico. He opened CBI in 2011 and launched RE/MAX Romantica in November 2023. His desire to learn something new prompted his return to real estate while managing CBI, and it was during a chance dinner conversation that he came upon the opportunity to open the RE/MAX franchise.

Rappaport’s love for Puerto Vallarta had blossomed during his time in Mexico as part of the exchange program. In 2003, he visited the city on vacation twice and ultimately decided to set roots in this magical town. Reflecting on his life, Joshua recalled taking the bold step of relocating at the age of 23, eager to discover what life had in store for him.

We debated when it’s more courageous to make a life change: starting early and charting a course on a blank canvas, or later in life, uprooting a well-established life in search of something new. He thought it was the latter that was more challenging.

Joshua’s personal life mirrors the energy of his professional endeavors, overflowing with activity and passion. He has completed nine marathons throughout his adult life, each one a testament to his dedication and resilience. During our meeting, he was excitedly preparing for his next challenge, only a couple of weeks away: the iconic marathon in New York City.

Josh completed the NYC marathon running through all 5 boroughs. His disciplined and regimented lifestyle has taken him on these exhilarating journeys, running 26.2 miles through places like Puerto Vallarta, Boston, Chicago, New York, and Tokyo.

Now, with an adventurous spirit, he has set his sights on Berlin, planning to tackle yet another marathon in 2025. This will complete his journey to become a member of the very few who have finished the prestigious Abbot 6 World Major Marathons. When asked about his relentless drive to keep participating in these races, Rappaport shared that it’s the profound sense of camaraderie that envelops him at the starting line, connecting him with fellow runners from around the globe. He expressed how the process of training—accumulating thousands of miles in preparation—culminates in an unforgettable marathon experience. It’s the sensation of being surrounded by people worldwide that he loves along with the goal-based aspect of it.

“It’s fascinating how running a marathon eventually dictates your life,” he said. “Especially six weeks before the date.”

Rappaport attributes much of his structured and organized personality in managing CBI and RE/MAX to running.

“Being ambitious is part of my personality,” he went on. “Running has helped me formulate how to set my goals.”

Joshua’s determination to accomplish his objectives became evident when he described the process of opening Cross Border Investment. After working for a mortgage company for five years, he decided to branch out and started the business from the guest bedroom of his apartment. As the saying goes, nothing worth pursuing comes easy, and that was true for Rappaport as well. Soon after launching CBI in 2011, the financial crisis caused most mortgage lenders to disappear. However, his perseverance and innovative approach, particularly in working with Mexican national banks to facilitate Canadian and American financing, helped the business thrive into what it is today.

One of the many advantages of managing both companies is that RE/MAX Romantica clients have a very close relationship with their real estate agent & their CBI Mortgage Originator, as well as RE/MAX clients can benefit from CBI’s legal team and have their expertise involved in all aspects of the transaction. This means they have in-house attorneys who draft sale contracts, review property deeds, prepare legal documents, etc. This structure allows Rappaport to provide a layer of security for transactions not offered in many offices, with RE/MAX agents focusing on market trends and promoting properties, not working their way through contracts and reviewing legal documents.

“This ensures proper due diligence and gives clients peace of mind that the sales contract has the property clauses the buyer needs to be protected. Sellers also benefit greatly from CBI’s legal expertise, as CBI will review to ensure that the property documents are all in order, guaranteeing a quicker closing and will also work with the seller to provide the lowest capital gains calculation possible.”

Another benefit Rappaport mentioned of having CBI is the availability of mortgage lending options for Americans and Canadians. When a prospective buyer inquiries about mortgage options, RE/MAX agents have close relationships with the expert mortgage originations at CBI, enhancing the service provided to clients.

Having the corporate backing of reputable brands like RE/MAX, combined with expert legal and mortgage services, distinguishes Joshua Rappaport and his team from other real estate businesses in Puerto Vallarta. This aligns with Joshua’s vision of being a business director rather than being a sales agent who owns a real estate company, as he focuses on offering his agents guidance and education to help them succeed.