From 1890 to South Florida: Michael Lessing's Enduring Family Hospitality Legacy (Ep. 54)

In this captivating 54th episode of Success in South Florida, host Adam Rossen sits down with Michael Lessing, the driving force behind the 135-year-old Lessing's Hospitality Group. Michael shares the incredible journey of building and sustaining a multi-generational family business, offering a unique perspective on adapting through five generations and successfully expanding from New York to the dynamic South Florida hospitality scene.

 

Discover what it truly takes to maintain a thriving family legacy, the crucial lessons learned from navigating over a century of change (including major economic shifts and the COVID-19 pandemic), and the strategic insights behind their successful move to the Sunshine State.

 

Whether you're part of a family business, an aspiring entrepreneur, or fascinated by enduring success stories, this episode is packed with real-world wisdom and actionable takeaways from a true hospitality veteran.

 

Episode Highlights:

✅ The inspiring 135-year journey of Lessing's Hospitality Group 

✅ The keys to navigating generational transitions in a family business 

✅ How a historic New York company successfully expanded to South Florida 

✅ Critical lessons learned from adapting to over a century of change 

✅ Michael Lessing's invaluable advice for building a lasting business legacy

 

Chapters:

00:00 - Introduction to a Century-Spanning Hospitality Story 

00:28 - Meet Michael Lessing: Leading a Timeless Enterprise 

01:15 - The Foundation: Building a Business in Early Manhattan 

05:16 - Expanding Reach: From Long Island to New Ventures 

12:25 - The Role of Guidance: Navigating Family and Business Dynamics 

23:43 - The South Florida Calling: Embracing New Opportunities 

30:46 - Weathering the Storm: Lessons from Unprecedented COVID Times

36:40 - Comparing Markets: The New York and Florida Experiences 

42:46 - Enduring Wisdom for Business Builders 

47:59 - Connect with Michael Lessing

 

About Michael Lessing:

Michael Lessing is the dynamic President of Lessing’s Hospitality Group, a sixth-generation, family-owned powerhouse serving the East Coast for over 130 years. As chairman of the company’s Executive Committee, this proud Long Island native leads a legacy founded in 1890, encompassing over 100 locations across the Northeast and Florida.

 

Leading an organization with 15 family members, Michael has been instrumental in Lessing’s enduring success, driven by his belief in quick adaptation and the ability to pivot. A testament to this was the company's vital partnership with New York City during the pandemic, delivering over two million meals. Michael is spearheading expansion across all divisions, including the exciting Love Street Project in Florida, all while fortifying Lessing’s renowned hospitality.

 

Actively involved in numerous professional and charitable organizations, Michael’s leadership has earned him accolades like the 2017 Executive Circle Award and Family Business CEO of the Year. Beyond the business, he enjoys boating, the beach, and good food, always prioritizing the enduring strength of family within the Lessing’s legacy.

 

About Lessing’s Hospitality Group:

Lessing’s Hospitality Group comprises over 100 locations throughout the Northeast and Florida. Lessing’s operates 21 wedding and catering venues, 16 full-service restaurants, over 75 corporate and academic dining centers, a historic inn, and a presidential yacht. Steeped in over 135 years of tradition, Lessing’s Hospitality Group focuses on providing each guest and client with unique, personalized experiences and remarkable hospitality. Their extensive reach and diverse operations

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