Season 91, Episode 1087: Guest: Ryan Chiodo: Luxury, Trust, and the Long Game

“Price is what you pay. Value is what you get.” — Warren BuffettIn this episode, Jay sits down with Ryan Chiodo, one of the top luxury real estate advisors in Naples, for a conversation about entrepreneurship, trust, service, relationships, and what it actually takes to build a reputation at the highest level.Ryan’s story is not a straight line.From bartending in his family’s Italian restaurant…to learning the builder and developer side of real estate…to navigating REOs, short sales, and distressed assets during the Great Recession…to serving luxury and ultra-luxury clientele in one of the most competitive markets in the country…This episode is a masterclass in mastering your craft over decades.Inside this conversation:* Why communication and hospitality became Ryan’s unfair advantage in real estate* The hidden value of working in restaurants and customer service early in life* Why the luxury market is ultimately a relationship and trust business* The realities of serving affluent clients and what they actually expect* How the Great Recession shaped Ryan’s perspective on leverage, investing, and risk* Why many people underestimate how difficult real estate truly is* The importance of becoming a true subject matter expert in your field* Why over-communication creates trust and long-term referrals* How systems, teams, and delegation allow entrepreneurs to scale* The difference between working with buyers versus sellers* Negotiation strategies, creative deal structures, and thinking beyond price aloneOne of the biggest themes throughout this episode is simple:The people at the top are rarely doing complicated things.They are doing simple things with extraordinary consistency. Ryan also shares the daily disciplines that built his business over 24 years:* Reviewing the market every single day* Staying proactive with clients* Bringing value instead of “just checking in”* Responding quickly* Knowing the details better than anyone else in the roomThis episode is especially valuable for:* Entrepreneurs building a book of business* Realtors and mortgage professionals* Salespeople trying to create long-term referral networks* Anyone interested in luxury markets and relationship-driven business* Professionals looking to build mastery over time instead of chasing shortcutsA standout takeaway from the conversation:“You have to get in the room. But once you’re in the room, you better know what you’re doing.” This is a conversation about trust earned through preparation, consistency, and decades of repetition.Because in the end, luxury is not about flash.It’s about confidence, competence, and delivering an experience people never forget.