🎙️ From Sushi Concert Random Encounters to Dual CEO Leadership: Matt Winn's Journey Building Maple Hospitality and Arrive

In this inspiring episode, Matt Winn, CEO at both Maple Hospitality Group and Arrive, shares his journey from Orlando sushi concert champion seeking Miami opportunities through serendipitous encounters with mentors who immediately took him under their wings, accumulating two million Delta miles while leading a 1,200-person Cushman Wakefield team across 40 countries, launching Elysian Hotels boutique luxury brand during the 2009 financial crisis, and now operating top-grossing restaurants in Chicago, Dallas, and Arizona with Boston and New York expansions plus international vision. Balancing his “designated survivor partner” airplane schedule, Matt reflects on lessons learned from father’s wisdom-through-screwing-up philosophy, private equity Capital Group’s dig-deeper underwriting, and a 10-year Cushman Wakefield relationship that evolved into Maple & Ash partnerships with Danny’s two Michelin stars at Ria. He explains how luxury brand strategies like New York Times Magazine city-targeting ads and Scottsdale expansion certainty shaped growth, and why his three-things-right philosophy—great food, great service, nice atmosphere—combined with local customization creates celebration destinations. Businesses, he says, are like children with unique personalities requiring strengths maximization and weaknesses navigation, transforming from restaurant to enduring company through Prudential, Starwood, and Cushman corporate structure experience.

✨ Key Insights You'll Learn:

• CEO of both Maple Hospitality Group and Arrive Hospitality, balancing dual leadership roles Miami headquarters anchored by Maple & Ash’s 20,000 sq. ft. restaurant complex

• Direct growth strategy: hire the right people, avoid running out of money, senior leadership fundamentals

• Father’s wisdom: experience comes from screwing up — career philosophy shaping leadership style

• Cushman Wakefield leadership of 1,200-person team across 40 countries, foundation for later ventures

• 2009–2010 financial crisis lessons from opening at the wrong time, shaping resilience and strategy

• 10-year Cushman relationship evolving into Maple & Ash global sensation partnership

• Maple Hospitality growth: one restaurant expanding to 10 across five cities (Chicago, Miami, Dallas, Scottsdale, Santa Barbara)

• Top-grossing restaurants in Chicago, Dallas, and Arizona markets demonstrating operational excellence

• Expansion vision: Boston and New York openings next year, with international growth on the horizon

🌟 Matt's Key Mentors:

• Father

  Serendipitous Brief-Encounter Mentors

• Capital Group Private Equity

• Cushman Wakefield Leadership

• Elysian Hotels Partnership

• Danny (Maple Partner)

• Jim (Maple Partner)

• Prudential Starwood Capital Experience

👉 Don't miss this powerful conversation about serendipitous career encounters, holding-on-for-dear-life between private equity buy and sale, and transforming single restaurant into enduring company through three-things-right philosophy and corporate structure systems.

🔗 Connect with Matt Winn:

Company: https://www.maplehospitality.com/

Group Company: Arrive 

LinkedIn: Matt Winn

📄 Transcript Available: Matt Winn's Three-Things-Right Philosophy: Great Food, Service & Atmosphere 

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📄 Special Thanks to Anthony Codispoti & AddBack Benefits Agency: AddBack Benefits Agency - Providing innovative employee benefits solutions that improve employee well-being while optimizing your bottom line Website: addbackbenefits.com

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