We’re excited to introduce you to the always interesting and insightful Jay Caputo. We hope you’ll enjoy our conversation with Jay below.
Jay, appreciate you joining us today. One of our favorite things to brainstorm about with friends who’ve built something entrepreneurial is what they would do differently if they were to start over today. Surely, there are things you’ve learned that would allow you to do it over faster, more efficiently. We’d love to hear how you would go about setting things up if you were starting over today, knowing everything that you already know.
I believe that the real estate industry has such a high rate of failure due to the lack of a true “roadmap to success” upon licensure. In fact, there should be courses geared towards capturing clients and the day to day activities of successful agents PRIOR to licensure. The licensing exam is not wildly indicative of what you will be doing, as an agent. And the guidance you receive once you pass the exam is largely dependent upon the brokerage you join. Obviously, some brokerages provide more support than others. While I know there are a lot of different paths to “launch”, personally, I would’ve chosen to invest more effort into my own personal strengths, and weaknesses.
I have found that clients are really drawn to the human, more than the Brokerage. If you (the human), the agent, can invest in your knowledge and fast-tracking the ability to intelligently speak the language of real estate, as well as learn the contracts, you will be able to connect with clients better, quickly. In the beginning, I was buying leads and spending money I didn’t have on ads to get leads. Yet when the leads came in, I didn’t know how to communicate with them effectively. And my follow up systems were a joke. There are so many shiny objects in Real Estate, meaning that there is always the next, new way to “fast track” your success. If you do not invest in the skills to convert the shiny objects into clients, they are all just wasted time and money. The most sustainable way to “fast-track” is to invest in yourself, your knowledge, and the skills that will help you gain traction. The more agents that understand this at the beginning, the more successful the agents will be in their career.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers
I got into Real Estate after a long, decorated career as a Professional Chef. I got into the restaurant industry as a teenager, and I never knew another career. I went to the most prestigious culinary school in the country, the CIA, and I worked at some of the finest restaurants in the country. I opened my first restaurant at the young age of 31, and was recognized as a James Beard Award Nominee for Best Chef Mid-Atlantic on 5 occasions. This was the only thing I knew. At the age of 42, I had my first child and, as you can imagine, my whole world changed. I no longer could justify the long hours away from my family, and the all-encompassing effort that left me exhausted at the end of the day. My family needed me, and I needed them. So after some long deliberations with my wife, we decided I would retire from cooking, and pursue this career in. Real Estate. Seeing as the bar for licensure is relatively low, and I couldn’t justify going back to school for a degree, I pounced!!!
So at 45, I upended my life and became a Professional Realtor. I was able to dive in fast, and commit all of my resources to it, and I quickly created the brand “The Relentless Realtor” due to my tireless pursuit of my client’s dreams. The work ethic of a Chef is unparalleled, and I was able to apply this to my new career. And once my knowledge of the craft caught up with the work ethic, that is when things started to take off.
I learned that the underlying principles of both industries overlapped, more than I originally knew. I leaned into my innate ability to help people. And this was enlightening! No longer was I trying to help diners enjoy a special meal, hand-crafted with love, but was trying to help them with the largest purchase of their lives, in many cases. When I decided to take the approach of “How can I help you get what you want?”, I saw amazing results. And as I was able to scale this to more potential clients, the business erupted.
I also began to refine my systems, my message, and my Unique Value Proposition. I began to listen intently to my buyers and sellers. This allowed me, and eventually my team, to really craft a plan to help my client’s get what they want, based upon what they’ve told me. And my client’s really value that approach, and feel “heard”. We have been able to branch out, in terms of marketing, and markets we serve, as a result of the successes we have had. I really pride myself in, now, not only helping my client’s achieve their dreams, but also our agents.
I proud of a lot of what has happened in Real Estate, as my goals have continued to shift as we have helped more families. I think the highest achievement, so far, has been to open our new brokerage this year, Brushstroke Properties. We were able to partner with Side, a nationwide broker and industry leader, in order to fulfill our goal of providing the best client, and agent, experience. We believe that each transaction is a blank canvas because every buyer, seller, home, condo, etc… creates a unique experience each and every time. By the end of each transaction, we should have created a beautiful painting for our clients, one Brushstroke at a time. Side provides the platform, and Brushstroke, and our agents, provide the creativity to get it done for our people.
Our tagline is “Grounded in Tradition. Powered by Innovation. Proven Results.” This is exactly the way we treat each day, and it shows in our work. We do the work behind the scenes, when no one is looking, so we are able to provide an unparalleled experience when they are. We use cutting edge tech, coupled with knowledge and insight, to provide a data-rich environment in order to make sound financial decisions. We treat each client’s transaction as if it was our family, and we advise with integrity.
It has been a wild ride for the past 4 years, and we are so excited for the future of Brushstroke Proerties. We wouldn’t have it any other way!!!

Can you share a story from your journey that illustrates your resilience?
There have been many moments that have shaped who I am as a man, whole also informing my decisions as a businessman. My resilience has been tested, for sure. And this is why I created the brand The Relentless Realtor. Long ago, when I first moved to San Francisco to take a job as a line cook at the Lark Creek Inn, in Larkspur, CA, I barely had enough money to make it to SF, let alone rent a place to live in one of the most expensive cities in the country! So for the first 4 or 5 months, I lived in my Geo Prism. I kept all of my belongings in the trunk, and would sleep in the back seat. Each morning that I worked, which was 6 days a week, I would go in to the restaurant early and wash up, brush my teeth, etc… and get to work. On the night before I was off the following day, I would rent a room at the travel lodge a few miles away for $55 plus tax, and sleep in a bed, take a shower, and just get some comfort. It was heaven. This was the only way I could learn from some of the best chefs in the country, many of whom I am still friends with almost 30 years later!!!
Later, I have found that same relentless spark in my real estate career. I have had many clients, over half a dozen, who wanted to give up their search during the pandemic, when working with other agents. Once they were free from their obligations with the other agents, I was able to show them how my research, data, negotiating style, and relationships could help them achieve their goals. Once they decided to work with me, I proceeded to methodically find them the home of their dreams. Each and every one was able to win a contract on their new home that fulfilled their needs, often times when competing with over 10 other offers. Sometimes, we found them homes that were not even on the market. It is this approach, to being fully committed to my clients goals, that has helped set me apart in a sea of realtors.
How do you keep in touch with clients and foster brand loyalty?
The way we keep in touch with our past clients and foster loyalty is our relationship-driven approach to our clients. We have made a commitment to them, and are appreciative that they allowed us to help them with such an important aspect of their life. We use our CRM to help remind us to reach out and inform our actions, and we are constantly following up with them, providing value. Whether they need a trade worker to help with projects around the house, or its a birthday or anniversary, we want to constantly be in flow with them, making sure they know that we are a resource.
We also are providing valuable information about their home. Through various apps, we are able to provide them market updates, recent sales, and monthly home evaluations to keep them informed about their equity. We even provide updates about the rental value and Air BnB value of their home. So if they ever want to upsize, downsize, or move out of the area, they can feel confident that we are a resource to help guide their decision making process.
And finally, we host events, and invite our clients to them all. Whether it is a happy hour, a wine tasting, a sporting event, or a backyard BBQ at my house, we always invite our SOI to ensure they know we value them. It is in these ways that we ensure our work family is nurtured, and they know how much we care.
Contact Info:
- Website: www.brushstrokeproperties.com
- Instagram: https://www.instagram.com/thecaputogroup_official/
- Facebook: https://www.facebook.com/jay.caputo.925
- Linkedin: https://www.linkedin.com/in/jaytherelentless/
- Youtube: https://www.youtube.com/channel/UCi-sWOfngjWQ6zN4NQajxJQ
- Other: https://www.google.com/search?q=The+Caputo+Group&stick=H4sIAAAAAAAA_-NgU1IxqLCwTDJPMjU3MEs2szBLNDG1MqhIMTOwTEwzSzJJtjBLNbNcxCoQkpGq4JxYUFqSr-BelF9aAAA6-vPPOwAAAA&hl=en&mat=Cb4jBFQHkelDElcB8pgkaNjpllD2s9DcuM4m7ewObYaYx05K1o1hc2fA3B7z7SfoDWVyGFHGzNmsy3hWeXDrmlKy_LMPG6w3RlV6pcNEBSIksv9V0qML172sPTo5kqHkuUs&authuser=0

