Today we’d like to introduce you to Chris Pessy.
Hi Chris, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
The Story of Chris Pessy, Global Real Estate Advisor: A Journey of Purpose, Growth, and Connection
I was born and raised by a single mother in California, and she has always been my true north and greatest inspiration. My mother’s challenging upbringing shaped her into a person of remarkable strength and resilience—a teacher not only to me but to everyone fortunate enough to cross her path. Her unwavering spirit has been the cornerstone of my life, inspiring me to aim high and persevere, no matter the odds.
Growing up in Northern California, I developed a deep appreciation for hard work and a gratitude for life’s simple joys. After earning a degree in Industrial Design, I embarked on a transformative year-long backpacking journey around the world. From exploring the vibrant streets of Thailand to trekking to Mt. Everest Base Camp and living along the Nile River in Egypt, these adventures gave me a profound sense of freedom, discovery, and human connection. This experience shaped my worldview in ways traditional education could never achieve.
Upon returning home, I began my career as a designer. However, it didn’t take long to realize that the 9-to-5 life, with no equity in my work, wasn’t for me. I craved a path where I could control my destiny, and that’s when I discovered real estate and mortgage finance. I was drawn to the industry for its flexibility, the opportunity to help people achieve their dreams, and its reliance on building meaningful connections—skills I had honed during my travels. I chose an entrepreneurial path, much like my father, who has owned and operated just two companies in his 77 years.
I started humbly, training in real estate services from the dining room of my first mentor, Calvin. Those early days were filled with long hours and an unrelenting commitment to learning and growth. I thrived in the “what you put in, you get out” nature of the business, working 15-hour days with passion and purpose. From those humble beginnings, I began to climb the ranks, moving from small brokerages to mid-sized firms and eventually to Wells Fargo Mortgage. There, I achieved national recognition within my first nine months, ranking in the top 1% of originators.
When Robert Reffkin, CEO of Compass, offered me a founding role at Origin Point, I was deeply honored. While I ultimately chose a different path and relocated to Miami, his book No One Succeeds Alone deeply resonated with me. It reinforced a belief I hold close: success is never a solo endeavor. We all rise together, and our greatest accomplishments are built on collaboration, trust, and connection.
Over the past 23 years, I have had the privilege of funding and closing over $2.25 billion in real estate transactions. My work has taken me to some of the most dynamic markets in the world. Along the way, I’ve had the honor of collaborating with renowned professionals like Josh Altman (Million Dollar Listing), John Parsiani (Top Broker in Miami), and DeLeon Realty, WSJ’s #1 Realtor in the World. These partnerships have been both inspiring and instrumental in my career.
Mortgage Executive Magazine recognized me as one of the top 1% of Mortgage Originators in America, and in 2021, I was honored to receive the Scotsman Guide Top Originator Award. My work has also earned me #1 ratings in various highly regarded publications. Beyond the accolades, what I value most is the ability to empower my team and help them achieve their personal and professional goals. Building a successful team and watching them thrive has given me a profound sense of fulfillment and purpose.
As the son of a decorated war veteran, I’ve always admired the courage, strength, and stamina of those who lead with purpose. These qualities shaped my approach to life and business from an early age. My first business venture began with nothing more than a computer in the humble living room of a friend’s apartment. From there, it’s been a journey of perseverance, growth, and gratitude.
Beyond my professional life, I am passionate about giving back. I actively work alongside my friends Andrea and Veronica Bocelli to support the Andrea Bocelli Foundation (ABF), which empowers communities around the world facing disease, poverty, and social exclusion. It’s a privilege to contribute to a cause that aligns so deeply with my belief in the power of connection and collective growth.
Today, I’m proud to call Miami home and continue my work as an International Real Estate Advisor and Mortgage Executive. At the heart of everything I do—whether in business, philanthropy, or personal life—is the drive to create a lasting impact. From the lessons of my upbringing to the adventures that shaped my worldview, every chapter of my story has been about finding purpose, building connections, and helping others succeed.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Raised by a single mother who was broke and overcame adversity in many ways, including joining AA 40yrs ago and leaving corporate America to begin her massage practice. I personally changed careers from being laid off during the .com bubble pop as a designer, and boot strapped as a Jr. Realtor/Mortgage Originator from a studio apartment at 26yrs old.
Appreciate you sharing that. What else should we know about what you do?
Question 1 covers most of this, but to dive into details as a certified and designated CIPS (Certified International Property Specialist) I am one of 5000 Real Estate Advisors (Realtor) worldwide out of 6,000,000+ Realtors with this globally recognized designation. For me it’s not about just closing deals, but working with like minded and like hearted individuals, groups, family offices, organizations that have some fiber within them aligned with impact driven intentions. I care more about people, their families and supporting their journey’s and working on and with high integrity people and collaborations than I do with leaving this earth with the most money in the bank.
What are your plans for the future?
I’m looking forward to scaling my new personal platform as a dual licensed global real estate advisor with my own in-house mortgage lending platform globally. I just completed a new website focused on this expansion. chrispessy.com and also bringing more awareness to ABF, Andrea Bocelli Foundation and raising more donations in support of our cause to support humanitarian aid in Haiti and other Nations.
Contact Info:
- Website: chrispessy.com
- Instagram: @chrispessy
- Facebook: https://www.facebook.com/chris.pessy
- Linkedin: linkedin.com/in/chrispessy
- Youtube: https://www.youtube.com/@ChrisPessy
Screenshot
Image Credits
Gustavo Fernandez
