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Five Facts About Captive Insurance That You Need To Know

(948 reviews)

Produced on May 27, 2015

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Course Information

Time 1h 30m
Difficulty Advanced
Topics covered in this course: Insurance

Course Description

In this presentation, Elevate Captive partners Dave Kotowski and Jerry Messick, along with Jeffrey Simpson of Gordon, Fournaris, and Mammarella P.A., discuss the importance of Captives, including the IRS guidelines. The presenters begin by summarizing the process of establishing a Captive, along with discussing red flags and the best candidates. They conclude with a step-by-step explanation of creating an exit strategy.


Learning Objectives: 

I.     Identify what is a Captive and what are the IRS guidelines 

II.    Summarize the process for establishing a Captive 

III.   Recognize red flags and the best candidates

IV.   Comprehend exit strategies for Captives


Credit Information

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David Kotowski

Elevate Captives, LLC

Dave is a Founder and the Managing Partner of Elevate Captives, a leading captive insurance consulting with offices in New York, Oklahoma, Arizona and Hawaii. Our partners bring over 100 years of direct experience to our clients. Elevate works with some of the best companies and their most trusted advisors to help them save money, increase profits and lower insurance costs through our tried and proven LEVER Process: Learn * Educate * Value * Execute * Review. 

Dave graduated with a Bachelor of Arts in Organizational Behavioral Management from Brown University (Providence, RI). David has the expertise and drive of being an entrepreneur while also having the successful management skills of working in large, prestigious organizations. He has over 25 years of financial consulting experience. He was a Senior Vice President for both Merrill Lynch and UBS Paine Webber and also worked for Hong Kong Shanghai Bank. He has assisted a wide range of companies from Wall Street to Main Street.

As a former professional lacrosse player, Dave has been active in professional sports and has served in consulting roles to the NY Islanders of the NHL, the New York Dragons of the AFL, the New Jersey Nets of the NBA and was President of the Long Island Lizards of Major League Lacrosse. Dave is very active in connecting the passion of sports with the passion of business. He is the Founder of The Lacrosse Business Network and he developed the New York Islander’s Business Club.

Dave also serves as a keynote speaker for wide variety of organizations such as Law Line Merrill Lynch, UBS, FurtherEd, The CPA Roundtable, National Network of Accountants, The Accountant Resource Group, Hofstra University, Adelphi University, New York Institute of Technology, the Long Island Alliance (LIA), youth sports organizations, community groups and high schools. He is an approved Faculty Member for LawLine.com. Dave is very active in his community where he coaches travel lacrosse for his three daughters. He is the former Co-President of the Friends of Brown Lacrosse and he is also the former President of the Brown University Alumni Association of Long Island. Dave is also the Co-Founder of Team Elevate Lacrosse – a girl’s only lacrosse program aimed at preparing student athletes for college.

Dave lives in Lloyd Harbor, NY with his wife Nancy and their three daughters Victoria, Katie and Allie.

Jerry D. Messick

Elevate Captives, LLC

Jerry has 30 years experience in the insurance and alternative risk transfer industry.  He is the CEO for Elevate Captives, LLC (“Elevate”) with offices in New York, Oklahoma, Arizona and Hawaii. Elevate is a captive consulting and services firm that focuses on multiple industries and trade groups, including hedge funds, grocer owners/associations, financial institutions, manufacturing companies, and all providers in the healthcare space. Prior to buying into Elevate, Jerry was with a national provider of alternative risk services since 1985, where he held senior management positions with responsibility for loss control, marketing, finance, and captive insurance company operations. He is a specialist in board governance and the effective and conservative structuring of various captive and self-funding vehicles. In his position with Elevate, he is an approved captive manager in multiple jurisdictions, both onshore and off.

Jerry surrounds his personal life with his wife and 4 boys. He is a licensed pilot, scuba diver, and nationwide competitor in action pistol shooting. He owns a private investigation agency providing protective services, event security and fraud investigation exclusively to nonprofit organizations. Jerry currently serves as President of the Board for the Oklahoma Youth Orchestras, Founding Member and President of the Oklahoma Captive Insurance Association, member of the Alternative Risk Transfer Committee of the Self Insurance Institute of America (SIIA), and is actively involved as a speaker and participant on various committees for both captive trade associations and nonprofit entities.

Jeffrey K. Simpson

Womble Bond Dickinson

Jeffrey K. Simpson's practice focuses on the formation, regulation and governance of captive insurance companies. He is a founder and director of the Delaware Captive Insurance Association. He chaired and continues to serve on the committee that drafted Delaware’s updated captive insurance statute in 2005. He is active in captive insurance industry associations and frequently speaks on captive insurance topics. 

Jeff also has extensive experience as outside general counsel for small businesses. He assists clients with all matters in the life cycle of a business, including formation, financing, contracts, employment and strategic planning. His experience as an entrepreneur gives him a uniquely practical perspective in advising his business clients.

Areas of Practice

Captive Insurance, Trusts and Estate Planning, Business Planning and Transactions, Taxation



  • Villanova University School of Law, Juris Doctor 1997
  • Brown University 1987


Jory M.

I have already recommended this program to a colleague. Excellent!

Palanda B.

This was one of the best courses I took through Lawline. An informative, engaging panel that offered a lot of valuable content in a short timeframe.

Michael B.

Great program! I work with a risk retention group extensively, and this really helped me understand their business better and how I can bring greater value to their operations from a risk management standpoint.

Summer H.

Well done.

John L.

Excellent Intro to captives.

Ethan G.


Andrietta W.

Well presented and informative. Presenters were very knowledgeable.

Marc H.

This was interesting as well as useful

Charlotte G.

I took this course in preparation for an interview in Captive Insurance Regulation, recommended by the interviewing staff. This was a wonderful introduction. Thank you for the offering. I am a CPA, and would love to have seen it qualified as CPE by NASBA as well.

Desiree R.

This is illuminating it has opened the door by demystifying the subject area. Excellent course!

Matthew S.

Great job by the presenters. I really enjoyed the conversational approach.

Peter F.

very good...interesting

Donna W.

I learned quite a bit about something I knew nothing about before this course!

James D.

Great overview.


Great course on the fundamentals for start up of a Captive Insurer for big and small businesses.

Robin C.

This was my favorite course so far. Interesting and informative.

John R. M.

very informative and well done

Amy B.

Very interesting material on captive insurance!

Gilbert C.

One of the Best Programs on Lawline.

Joel E.


omar e.

Great roundtable format

Joseph M.

Interesting topic- I did not know what it was before this presentation

Steve H.

Good job!

julie f.

good refresher

Bonnie L.

Interesting content.

Gary D.

Totally arcane for most small practitioners but, interesting subject. Great choice.

Thomas M.

I never heard of this topic till today. Thank you.

Edward K.


John H.

great speakers

Veronica O.

Well presented; clear and concise

David K.


Chris P.


Sarah K.

very interesting subject matter

paul h.

Superb program.

Carolina S.


Elaine V.

very informative

Verlyn S.

Very informative

Michael L.

very interesting topic that I will be looking into further.

Phillip B.

captive insurance pretty interesting.

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