ABOUT US

Honest Advice for Reducing Catastrophic Risk

Left Tail Risk Advisors helps individuals, families and business owners manage and reduce life’s most consequential financial risks.

Traditional financial planning often concentrates on averages, foreseeable outcomes and events that are most likely to occur. We focus elsewhere — on catastrophic hazards that can permanently damage wealth, families or businesses. Our goal is to design and implement insurance-based solutions that help reduce the most devastating risks, strengthen long-term financial durability and facilitate smooth generational wealth transfer. 

LTRA is intentionally narrow. The advice we provide is specific, straightforward and tailored to each client's circumstances. Our offer is clarity, rigor and calm guidance so important financial decisions can be made with confidence and a thorough understanding.  

We are an independent insurance advisory with a single focus: our client’s best interest.* We do not answer to shareholders. We are not beholden to any insurance company. 

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*  New York Department of Financial Services Regulation 187 (11 NYCRR 224) requires that the sale of insurance be conducted “in the best interest of the consumer.” Some brokers and agents hide from “Reg 187” or rail against it. We welcome it, are proud to call New York our home and believe our client’s “best interest” always comes first.

THE  TEAM

Experienced Principals

OUR ORIGIN STORY

Broad Expertise From Multiple Insurance Vantage Points 

Left Tail Risk Advisors was formed after decades spent examining life insurance and risk management from multiple vantage points — as industry participants and insiders at major insurers, as attorneys representing policyholders with failed insurance policies, and as advisors to individuals navigating complex financial and cross-border risks.

          First, we have decades of experience litigating life insurance and other complex financial disputes, including class actions involving policy misrepresentations, unsuitable policy designs and contractual breaches. That work required a detailed examination of how policies are structured, illustrated and ultimately perform (or fail) under real-world conditions. Representing policyholders in these matters created a deep understanding of how insurance products and strategies succeed, struggle and sometimes fail.

          Second, our clients have included many high-net-worth immigrants and non-U.S. investors in matters involving investor immigration and the protection of substantial U.S. assets. That work exposed us to the unique planning challenges faced by wealthy globally mobile families, including cross-border estate exposure, liquidity needs and the importance of reliable U.S. dollar-denominated capital.   

          Third, we are industry insiders.  Joseph Gentile served as a life insurance agent with one of the nation’s largest mutual insurers, receiving formal training in insurance sales, policy design, underwriting and the practical realities of implementing insurance solutions for clients. Ronen Sarraf served as a senior trial attorney for the country's largest title insurance company. 

          Fourth, we have specialized expertise in the architecture and strategic uses of life insurance. We have closely studied the subject from multiple perspectives — legal, financial, actuarial and structural — and have passed exams for numerous advanced degrees, including the Chartered Life Underwriter (CLU) designation.

The result is a range of experiences unusual within the insurance advisor profession — industry-insider expertise, plan design and sales, insurance litigation, cross-border investments and advanced certifications. Few advisory firms have examined life insurance through so many lenses.

Left Tail Risk Advisors was thus formed to apply that experience constructively: to help clients design insurance strategies that are clear, durable and appropriate for the largest financial risks.

SOLUTIONS

Protection Solutions for Concentrated Risks

Left Tail Risk Advisors seeks to address outcomes that traditional financial planning often overlooks, underweighs or complicates. 

We focus us on strategic risk transfer, tax-efficient wealth and estate structuring, liquidity planning, and the intelligent use of insurance to provide dependable U.S. dollar-denominated capital when it matters most, especially for globally mobile and non-U.S. clients navigating cross-border exposures. 

Insurance can help reduce the most catastrophic financial risks and protect capital — especially illiquid assets such as a business, real estate or artwork — from being sold under pressure. 

LTRA provides the following core insurance products and services: Life, Disability & Long-Term Care.

MISSION & PHILOSOPHY

Providing the "Best" with Honesty, Clarity & Restraint

Our Mission

To help clients anticipate, quantify and insure against potentially devastating high-impact financial risks with contractual guarantees from highly-rated insurers that will enhance tax efficient estate, liquidity and succession planning with honesty, clarity and restraint. 

Our Philosophy

We are guided by the following principles:

            · The greatest hazards are not volatility or underperformance, but ruin and irreversibility.

            · Simplicity, redundancy and conservative design outperform complexity in high-stakes areas.

            · Standard financial planning optimizes for averages and underestimates the impact of "left tail" (i.e., catastrophic) risk — which should be transferred whenever feasible.