5 Surprising Facts About Ryan Gleason: The Entrepreneur Who Captured Alexa Ray Joel's Heart

Ryan J. Gleason is one of New York City's most successful and discreet entrepreneurs, a name that skyrocketed into public consciousness following his engagement to singer-songwriter Alexa Ray Joel, the daughter of music icon Billy Joel and supermodel Christie Brinkley. As of December 10, 2025, Gleason remains engaged to Joel, with the high-profile couple prioritizing their demanding careers before setting a wedding date, a decision that keeps fans eagerly awaiting the next chapter in their relationship.

The "Ryan Gleason wiki" search often leads to confusion, as the name is shared by several notable individuals, but it is the NYC restaurateur and hospitality mogul who has captured the public's imagination. He is known for his quiet tenacity, sharp business acumen, and a knack for creating popular, enduring neighborhood hotspots across Manhattan.

Ryan J. Gleason: The Entrepreneur's Biographical Profile

While Ryan Gleason maintains a relatively private life outside of his business and high-profile relationship, his career trajectory speaks volumes about his ambition and success.

• Shania Twains Bold Statement Why The Star Chose Nude Photoshoots At 57 Qf9cg

• Full Name: Ryan J. Gleason
• Occupation: Restaurateur, Entrepreneur, Hospitality Consultant, Real Estate Agent
• Primary Business: Owner of Paradise Hospitality, a firm responsible for designing and opening numerous New York City bars and restaurants.
• Notable Venues: Co-owner of Drexler's and Boulton and Watt, two popular NYC establishments, alongside business partner Darin Rubell.
• Relationship Status: Engaged to Alexa Ray Joel (since 2018).
• Fiancée: Alexa Ray Joel (Singer-songwriter, daughter of Billy Joel and Christie Brinkley).
• Current Projects (2025): Managing his hospitality portfolio, working as a Real Estate Agent with Compass in the Hamptons, and potentially running Venator Consulting, LLC.

The Rise of a New York Hospitality Mogul

Ryan Gleason’s primary professional identity is rooted in the competitive, fast-paced world of New York City's hospitality scene. His journey is a testament to strategic vision and over 15 years of hands-on experience in the industry.

Building the Paradise Hospitality Portfolio

Gleason is the owner of Paradise Hospitality, a company that has been instrumental in the design, development, and launch of numerous successful bars and restaurants across Manhattan. His expertise lies not just in opening a venue, but in creating a lasting, vibrant atmosphere that resonates with the local community.

Two of his most recognized and enduring ventures are Drexler's and Boulton and Watt. These establishments, co-owned with fellow restaurateur Darin Rubell, are celebrated neighborhood hangs known for their quality drinks and relaxed, inviting environments. Drexler's, a cocktail bar, and Boulton and Watt, a popular neighborhood spot, highlight Gleason's ability to craft diverse and profitable concepts.

• 5 Shocking Facts About Anna Congdon Penn State Sweetheart To Nfl Fiances Social Media Firestorm Cc90e

The success of these ventures has solidified his reputation as a formidable entrepreneur. His work involves everything from initial concept and design to managing daily operations, showcasing a comprehensive skill set that goes beyond simple ownership.

A Strategic Move into Hamptons Real Estate

In a move that demonstrates his diverse entrepreneurial spirit, Ryan Gleason has also expanded his career into the luxury real estate market. He is a licensed Real Estate Agent affiliated with Compass, focusing his efforts on the exclusive Hamptons market. This pivot allows him to leverage his deep understanding of design, architecture, and high-end client service—skills honed over a decade and a half in the hospitality industry—to assist clients with property projects.

The High-Profile Engagement to Alexa Ray Joel

Ryan Gleason’s relationship with singer-songwriter Alexa Ray Joel brought him significant media attention, transforming him from a successful but low-key restaurateur into a fixture in celebrity news. The couple began dating in 2013, and their connection quickly became a subject of public interest due to Joel's iconic parentage.

• The Facts Of Life Cast Where Are Eastlands Girls Now 2024 Updates 2tx8p

The New Year's Day Proposal

Gleason proposed to Alexa Ray Joel on New Year's Day in 2018, a romantic start to the year that was announced with a celebratory Instagram post. The engagement instantly made headlines, linking the successful entrepreneur to one of music and fashion's most famous families: the Joels and the Brinkleys.

His acceptance into the family was a smooth one. Both Billy Joel and Christie Brinkley have expressed their support for the union. Gleason is often seen joining Joel on work trips to wineries and other venues, indicating a strong partnership both personally and professionally.

Why the Wedding Date is Still Pending

Despite the engagement taking place several years ago, the couple has yet to set a firm wedding date. The most recent updates indicate that both Alexa Ray Joel and Ryan Gleason are incredibly busy with their respective careers—Joel with her music and Gleason with his expanding portfolio of hospitality and real estate ventures.

This delay is a modern reflection of two successful individuals prioritizing their professional ambitions while maintaining a strong, committed relationship. Their focus on career growth before tying the knot provides a unique narrative in the often-rushed world of celebrity engagements.

Clarifying the Ryan Gleason Entity Confusion

The name "Ryan Gleason" or "Ryan Gleeson" is an entity that refers to several distinct professionals across different fields, which often confuses searchers looking for a single biography. This highlights the importance of precise topical authority when researching public figures.

• Ryan Gleeson (UK Comedian): A multi-award-winning professional stand-up comic from the UK who began his career at the age of 16 in 1997. He is known for his lively sets and has won no fewer than five awards over his career, having also served as the resident compere of the Comedy Station Comedy Club.
• Ryan Gleason (Indianapolis Artist/Musician): An artist and musician based in Indianapolis whose current projects include an ongoing series of recordings and musical instrument building, often associated with local events like the ELEKTRONIK MUSIK FEST.
• Ryan Gleason (Actor): There is also a mention of an actor named Ryan Gleason whose career spanned from 2006 to 2012, appearing in Action, Drama, and Biography genres.

While the other individuals are successful in their own right, the "Ryan Gleason wiki" search is most frequently driven by public curiosity about the entrepreneur connected to the Joel-Brinkley lineage. His diverse career as a restaurateur, entrepreneur, and real estate agent ensures his name will remain in the headlines as he continues to build his empire and, eventually, walk down the aisle.