Thomas Cleary

Risk Management & Workers Comp

Clearwater, Florida, United States
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I provide commercial business insurance and risk management to hospitality and real estate businesses. I make insurance simple.

Key Consulting Services

  • Commercial Business Insurance Hospitality
  • Risk Management Consulting Hospitality
  • Workers Compensation Hospitality
  • Employee Benefits Hospitality


I provide a comprehensive risk assessment of the current insurance program, interview the client in depth to determine their appetite for risk and recommend and place the policies necessary using our marketing power of over $200,000,000 in premiums to obtain the most cost effective policies.


  • A graduate of the Cornell Hotel School 1989, I worked for five years with Hyatt Resorts in Orlando, Aruba and Tampa in Engineering Management. In 1993 I left operations to begin an insurance career. My education and operational experience combined with over 20 years of insurance expertise allow me to offer unique, simple, cost effective solutions for clients from one to fifty properties.

Professional & Other

- Cornell School of Hotel Administration 1989 (Finance and Food & Beverage Concentrations)
- Hyatt Resorts – Engineering Management Orlando, Aruba & Tampa 1989 – 1993
- Vice President – Hospitality Insurance Practice Leader East Coast Acordia / - - - Wells Fargo 1993 – 2006
- Equity Partner – Sihle Hospitality Insurance Group 2006 – 2011
- Equity Partner - Harper Insurance Group 2011 -
- Associate in Risk Management designation
- Board of Directors – Florida Hotel and Motel Association 2003 – 2005
- Board of Directors – Better Business Bureau of West Florida 2008 to Present
- Chairman – Florida Restaurant and Lodging Association Insurance Council

Thomas's Latest Articles & Case Studies

Thomas Cleary

Impact on Workers’ Compensation in Hospitality Due to Covid-19

By Thomas Cleary May 23, 2023

Hospitality businesses need to understand how claims under Covid-19 will impact their business and their peer group.  Any claims paid out will...

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Thomas Cleary

What To Do About Hospitality Commercial Insurance due to COVID-19

By Thomas Cleary May 23, 2023

ALL hospitality operations have been adversely impacted.  Insurance is something we don’t think about, until we have to. Step 1: File an...

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Thomas Cleary

How Recent Florida Worker Compensation Changes Will Impact Your Operations

By Thomas Cleary May 23, 2023

Making hotel insurance simple, and saving you money in the process. You may be aware of this recent judgment, maybe not. Either...

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