Meet Ryan Raveis: Leading a $16B Family Legacy, Raising Three Amazing Kids, and Finding Strength in Community & Music Ever wonder what it’s like to lead one of the largest family-owned real estate, mortgage, and insurance companies in the country—all while raising a family and giving back to the community? In this heartfelt interview, Ryan Raveis, Co-President of William Raveis Real Estate, Mortgage & Insurance, opens up about growing up in Fairfield, the joys and challenges of fatherhood, the profound impact of family—especially after a devastating loss—and how he’s using his passion for music to bring people together for good. Whether you’re a parent, a business leader, or someone who believes in the power of community, Ryan’s story is sure to inspire. Read on for real talk about resilience, love, and what it truly means to lead with heart. Thank you Ryan!
Where are you originally from and how long have you been in Fairfield?
I grew up in Fairfield. My mom and dad met at Rodger Ludlow High School, married in their early 20s, and raised three children in Fairfield. I spent the majority of my childhood in our house on Hulls Farm Road before heading off to prep school (Taft) and college (Williams). After college, I moved to Boston for several years and got my MBA at Babson before returning to Fairfield at 27 to join my family’s business and raise a family.
Tell us about your Family!
I’m the youngest of three children, my sister (11 years older) is in Naples, FL and my brother (7 years older) is in Rowayton. My mom passed when I was 27 and my dad splits his time between Naples and his home on Hillside Road.
I married my college sweetheart, Meghan, and we have three children: daughter, Eleanor (16) and twin boys, Dane and Conor (14). I was extremely lucky to find love at an early age and develop a strong relationship with Meghan that would grow as we experienced all the twists and turns of life that accompany parenting and adulthood.
In June of 2023, we suffered a tremendous loss when Meghan was suddenly taken from us in an accident; she was hit by a car while she was out on a walk one Friday afternoon. Not a day goes by that I am not grateful for our time together and the impact that she had on me as a best friend, wife, and mother.
One thing people would be surprised to know about you?
Following our loss of Meghan, out of necessity, I did some soul searching and began tapping into areas of life that brought me personal joy. I reconnected with my passion for playing music, singing and playing the guitar. Throughout high school and college, I was in musicals and played guitar in bands. Music took a back seat in my 20s as I focused on building a career. In my 30s, I picked it back up and began taking courses at Berklee School of Music in Boston on rock, blues and jazz guitar. Today, I’m routinely playing in the area (The Horseshoe is among my favorites!), and I have recently begun partnering with some outstanding professional musicians to produce large-scale events to raise money for charities. The concept is to bring our community together, have fun, and give back to those in need. Our signature event, Ravestock, will be held September 26th at the FTC Warehouse to raise money for cancer research, in memory of Meghan Raveis.
One thing you wish someone would have told you about fatherhood?
If I think back to my 30-year-old self, waiting for my daughter to be born, I’d tell him that he will be surprised at what he is capable of. Firstly, you can love someone so much that you will instinctively put yourself second. Then, along the path of parenting, you will somehow find a way to do what’s needed to make sure your family is in good shape. For instance, when one of our children had to be rushed to St. Vincent’s Hospital at four months old with a heart issue, I found the resilience to care for him and also parent the other children, work a job, and be a loving spouse. The stakes get higher, but you learn how to handle them.
What’s your favorite thing about raising a family in Fairfield?
My own experience as a child helped me make a conscious choice to move back to Fairfield. Outside of the geography and obvious spoils like the beach, restaurants, social activity, etc., it’s an amazing community of people that care about each other.
Best dad hack that makes your life easier?
Life360… kidding (… but not kidding). I feel the toughest part of being a dad is the emotional toll of the ever-present thought, “How are my kids doing?” I figure that if I know the answer to that question (rather than assuming), it takes a lot of weight off my shoulders. The only way to do that is by communicating and spending a lot of time with them.
Tell us about your job, when & why you decided to start in this field?
I’m Co-President of William Raveis Real Estate, Mortgage & Insurance, a company that my dad started 51 years ago in Fairfield Center. We help buy/sell, finance and insure residential properties throughout the Northeastern US, Florida and South Carolina. What started in a small office, above where Fairfield Jewelers is today, has grown into a network of 5,000 agents.
What do you love about your job? Challenges you face?
I’ve worked with my dad and brother for over 20 years, and we’ve grown the company substantially during that time, becoming the largest family-owned real estate & financial services company based in the eastern US. And while I like the strategic elements of running the business itself, I love that it’s a “people” business. We have a community within William Raveis that is full of people who are passionate about their job, their customers, and having a positive impact on the community around them.
If you weren’t working in this industry, what do you think you would be doing today?
I was in Management Consulting when I worked in Boston in my 20s, so I would have likely stayed on that path. But if I wanted to follow my passion, I’d be coaching high school sports. I was the captain of three sports in high school and some of the most impactful lessons of my life came from my coaches. They taught me about leadership, accountability and compassion – lessons I still use today as a business leader and a parent.
Best advice for dads who experience the inevitable guilt handling a career and helping support a family?
You’re doing the best you can in this present moment, and every decision that you’ve made in the past was with good intentions. Guilt is a useless emotion that shouldn’t be a product of parenting.
Who has most influenced you to be the father that you are today?
I had a great role model in my own father, but as my spouse, best friend, and an amazing mother, Meghan was my greatest influence. Parenting came very natural to her, and she had a very clear sense of what it took to provide a stable environment for the children to grow. She knew how to establish accountability with our children and did it with a deep lovingness that created a culture of respect and love for each other. I’m extremely grateful for her and the time I spent with her as a husband and partner in parenting.
What advice would you share with a new dad or other dads?
It’s such a cliché but stay in the present moment. Life with your kids goes by quickly. Often, the age at which you become a dad collides with inflection points of your career and other life stresses. If you can remember that you have a resilience within you that may be yet undiscovered, it can help you from feeling overwhelmed. At some point you’ll look back at fond memories of when your children were toddlers – just make sure you slow down enough to take it all in and help shape the memories.
We love supporting local businesses – favorite places in Fairfield to…
Have Dinner with Family:
Luigi’s and Centro’s are the OGs, but we also enjoy Malibu Taco, or Artisan for special occasions.
Grab a Drink with Friends:
The Shoe
Have a Date Night:
The bar at Bonda or Artisan
Spend time together as a Family:
We spend a lot of time at home as a family. I love having the teenage kids around. But outside of that: Sasco Beach
Outside Activities:
Hikes in Devils Den or the Audubon (which was perfect for when they were younger)
Grab coffee:
Gruel Britannia or Isabelle et Vincent