We’re excited to introduce you to the always interesting and insightful Chris Pessy. We hope you’ll enjoy our conversation with Chris below.
Alright, Chris thanks for taking the time to share your stories and insights with us today. Parents can play a significant role in affecting how our lives and careers turn out – and so we think it’s important to look back and have conversations about what our parents did that affected us positive (or negatively) so that we can learn from the billions of experiences in each generation. What’s something you feel your parents did right that impacted you positively.
As the man of the house at age 2 my mother instilled a foundation of work ethic, compassion for others and always give from a place of love with zero expectations. Be the light you wish to see in the world and embrace chaos and adversity with the same open mindedness when spreading joy and happiness.
Chris, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
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.
Sets me apart: 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.
We’d love to hear the story of how you turned a side-hustle into a something much bigger.
Yes, my side hustle as a small family VC office and an investor in the Michael Mina restaurant group both provided platforms for bringing high integrity heart felt and like minded investors, philanthropists and the likes into a sphere of trust which cultivates joy and a space to create opportunities in real estate sales on a global scale.
How about pivoting – can you share the story of a time you’ve had to pivot?
I walked from San Francisco and a Top1% position with Wells Fargo Mortgage to expand my business in a city that I have loved and visited since 2005 – Miami. At that point I also started giiving more, and spending more time and energy aspiring to support Andrea Bocelli’s Foundation (charity). This has created a sphere of affluence and aligned me with creating more impactful opportunities in bigger circles with high integrity clients and partners.
Contact Info:
- Website: chrispessy.com
- Instagram: @chrispessy
- Facebook: https://www.facebook.com/chris.pessy
- Linkedin: https://www.linkedin.com/in/chrispessy/
- Youtube: https://www.youtube.com/@ChrisPessy
Image Credits
Gustavo Fernandez