About LSS

LSS is a boutique life settlement consulting company located in Naples, Florida. LSS consults for clients in the acquisition and servicing of life settlements. With years of business and life settlement experience, we provide our clients an unparalleled expertise and level of service.

With our own proprietary methods, LSS is able to more accurately navigate the life settlement marketplace while adhering to our core values. These include integrity and ethical practices, direct, open, and honest communication, and an unparalleled commitment to clients.  


Life Settlement Strategies of Florida (“LSS”) provides a number of services in the life settlement industry. Below you will find more information about the various services available to our clients. 

Actuarial/ MEdical Review Services

LSS has propriety software and actuarial relationships to provide both medical and statistical actuarial underwriting. 


Life Expectancy Evaluation

Through LSS’s vast database of life expectancies (LEs) and years of experience tracking LEs, LSS is able to more accurately evaluate LEs from other companies. 

Premium/rider optmization

LSS is able to optimize premiums, evaluate riders and shadow accounts, and ultimately find hidden value in policies for clients. 


LSS is able to take the combination of their life expectancy evaluation, actuarial services, and premium optimization to provide more accurate policy price evaluation. 


LSS handles all aspects of portfolio administration for clients from acquisition to completion of the policy. These services include premium payment management, document management, medical record servicing, and life expectancy services. 

Life Settlement related financing

LSS finances various facets of the life settlement industry. Please contact us today to discuss your financial needs. LSS is able to fully determine a policy’s or portfolio’s value to provide higher LTVs for financing. 


Estate Planning Attorneys

Help your client get the full value of their life insurance policy from scenarios such as Trust Owned Life Insurance, Bankruptcy, Divorce, Retiring Business Owners, and Insurance Purchased for Estate Taxes.

CPA's and Tax Advisors

Help your client convert a capital asset into cash with Liquidity for Retiring Business Owners, Leveraging Corporate-Owned Policies, and New Tools for Bankruptcy Trustees.

Business Valuation Appraisers

Help go an extra step to ensure your client is obtaining the best advice in their key man life insurance asset needs.


The Life Settlement Strategies of Florida Team brings a diverse background including business development, M&A, real estate and development, precious metals, with the culmination of all this experience adding to life settlements. 

Todd Green


Todd Green was born in Monmouth, IL. He attended college at the University of Arkansas and played football for legendary coach Lou Holtz. At age 23, Todd got his start in the car dealership business, becoming the youngest Toyota dealer in the nation. Over the years, that has expanded into 13 different car brands, selling over 15,000 cars per year. In the 2000s, he began to diversify into other business ventures. Todd brings his 40+ years of business knowledge and investments to LSS. He spends most of his time in Naples, FL and the other time in Springfield, IL. Todd has been married for 27 years and has two children in their early twenties. In his free time, Todd enjoys playing pickle ball, golfing, and traveling with his family.

Clay Winfield


Clay Winfield was raised in the Midwest and attended Southern Illinois University (SIUE). Clay founded Winfield Construction in 1974. The business focuses on the construction of homes and apartments, commercial construction, and land development. Clay created two bank holding companies in Illinois and Florida and holds a board position for a publicly traded company. Clay has always been involved directly with people and enjoys the business relationships he has made through the years. He has been a full time resident of Naples, Florida, since 2000. Clay and his wife, Bonnie, have been married for 28 years. They have five children and six grandchildren. In his spare time, Clay enjoys golf, traveling, and spending time with his family.

John Marques


John Marques was born in Hinsdale, IL. He attended DePaul University where he earned a bachelors degree in the Science of Commerce. After college, John spent a decade in the entertainment and jewelry industries. John found a calling in the life settlement industry. John is a licensed life insurance agent and life settlement broker. He is proficient in all aspects of life settlements including contracts and negotiation, business development, life settlement evaluation and pricing, portfolio administration, complex mathematics, accounting, marketing, websites and SEO, and MAPS pricing. John lives in Bonita Springs, FL, with his wife, Dayna. In his free time, he enjoys biking, hiking, camping, and snorkeling.