Legalized Cannabis is Big Business

Level: Advanced
Runtime: 63 minutes
Recorded Date: October 24, 2019
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  • Marijuana Legalization Overview
  • The Underwriting Perspective
  • Trends
  • The Broker's Perspective
  • Cannabis and Commercial Real Estate
  • Major Congressional Issues Facing the Cannabis Industry
  • Cannabis Legalization and Legislation
  • SAFE Banking Act
  • Additional Points of Consideration
  • Q & A
Runtime: 1 hour and 3 minutes
Recorded: October 24, 2019


The gradual legalization of medical and recreational marijuana by individual states means that regulations differ from state to state, complicating the efforts of businesses operating in multiple states. This webinar will take an in-depth look at the types of coverage required by these various entities, their unique risks and the opportunities they present for insurers looking to expand their coverage products.

Sharing their expertise will be Kieran O’Rourke, vice president and director of underwriting for Cannasure Insurance Services; Steven Sherman, J.D., vice president of the cannabis risk group at PSA Insurance and Financial Services; and Stanley Jutkowitz, senior counsel at Seyfarth Shaw and head of the firm’s cannabis practice.

This program was recorded on October 24th, 2019.

Provided By

Property Casualty 360


Taite R. McDonald

Holland & Knight LLP

Taite R. McDonald is an attorney in Holland & Knight's Washington, D.C., office and a member of the firm's Public Policy & Regulation Group. Ms. McDonald focuses her practice at the intersection of innovation and government. She is especially well versed in running complex, cross-government matters with intricate legal, policy and financing components. Ms. McDonald's is highly knowledgeable in several areas, including energy technology commercialization, federal energy procurement, biofuels, cannabis, hemp, innovative U.S. Department of Defense (DOD) contracting, and government grants and loan guarantees.

Ms. McDonald provides counsel to companies of all sizes, from early stage startups to Fortune 100 companies and large utilities. She has successfully represented clients in obtaining government contracts, non-dilutive funding in excess of $100 million, loan guarantees and conditional commitments in excess of $1 billion, and achieving complex policy and legislative objectives. Ms. McDonald regularly plays a pivotal role in assisting clients to overcome gating obstacles and achieve new and innovative legislative objectives for emerging markets and technologies by forging key partnerships with federal agencies, industry, trade groups and other government-facing bodies.

Additionally, Ms. McDonald was selected as a 2019 Holland & Knight Rising Star and is a frequent writer and speaker on topics related to renewable energy, military privatization, cannabis and government finance. She has spoken at dozens of conferences and events, including the Defense Energy Innovation Summit, Association of Defense Communities Advanced Energy Summit, Advanced Biofuels Leadership Conference, U.S. Department of Energy (DOE) Bioenergy Advanced Biofuels Leadership Conference and Power-Gen International Finance Forum. In 2019, Ms. McDonald was named as a Key Player on K Street in Politico’s Essential Guide to Cannabis.

Stanley S. Jutkowitz

Senior Counsel
Seyfarth Shaw LLP

Stan enables entrepreneurs and businesspeople to achieve their goals, and excels at solving complex, unconventional business challenges.

Entrepreneurs seek to buy and sell companies, and engage in liquidity transactions in the most practical and tax efficient manner. Stan helps clients find a way to achieve their goals with the least possible tax cost. He is both a business attorney and a tax attorney who "stands in the shoes of his clients" to provide direct and cost-effective advice.

Stan concentrates his practice on domestic and international business transactions, tax planning, and counseling on corporate and real estate transactions. His experience in international business law and transactions includes structuring entities for tax efficiency, and representing clients in cross-border mergers, acquisitions, and other transactions. Having worked on many transactions where parties had conflicting goals, Stan brings a unique ability to find solutions so that all parties of a transaction achieve their goals, while getting the deal done.

As the leader of the firm's cannabis law practice, Stan keeps up with the evolving law, and works with clients on corporate transactions and business counseling in the cannabis space. He helps clients navigate the uncertain legal landscape of the cannabis industry, and guides clients through challenges to enable them to conduct business with the least amount of disruption. Stan is the founding editor of the firm's marijuana law blog, The Blunt Truth (

Stan appreciates the unpredictability of his job. He enjoys the new challenges, new opportunities, and new problems that he faces every day. Clients appreciate Stan's willingness to discuss matters by phone, rather than relying too heavily on email communication.

Steven Sherman, JD

Account Executive
PSA Financial Advisors, Inc.

Steven Sherman J.D. has over 12 years of experience in the insurance industry. Steven provides a variety of risk management solutions for physicians, lawyers, and other professionals. He is also the area’s leading cannabis insurance expert, securing specialty coverages for medical and recreational marijuana growers, processors, dispensaries, security firms, lawyers and consultants serving the cannabis industry. His legal background and insurance expertise allows him to use his wide network of resources to offer creative solutions for his clients.

In his former role, Steven oversaw the development of a captive insurance company as Executive Director of LifeSpan Products & Services, where he evaluated different insurance programs for the organization. Steven’s experience both as a buyer and a seller of insurance, represents an advantage to his clients as he is better able to understand needs and exceed expectations.

Steven earned his BA from Emory University in Atlanta and earned his J.D. from the University of Baltimore School of Law. He is also a member and PAC Director of the Maryland Medical Dispensary Association.

Kiernan J. O'Rourke

Vice President and Director of Underwriting
Cannasure Insurance Services

Kieran J. O’Rourke has over 30 years of impressive commercial underwriting, product and program development experience in the insurance industry.

Prior to joining Cannasure, Kieran was Assistant Vice President of Property Underwriting of AmTrust Financial Services, Inc (AFSI). Kieran’s career experience spans P&C underwriting, MGA underwriting for alternative energy products and alternative market product development, oversight of research and product development and directing regional commercial insurance sales for a Fortune 500 carrier.

Kieran is a talented and respected leader. His disciplined underwriting approach and business fundamentals consistently yields sustainable growth and profits relative to proprietary program development.

At Cannasure, Kieran manages the firm’s Program division and guides the company’s development of future cannabis and hemp programs.

Kieran’s expertise keeps him busy and is well sought after by leading media outlets and speaks at insurance and cannabis industry events. Kieran has a unique perspective and thought-leadership of underwriting relative to the emerging trends and risk transfer solutions in the cannabis and hemp arena.

A graduate of The University of Akron, Kieran holds the Chartered Property Casualty Underwriter (CPCU) designation, as well as the Certified Insurance Counselor (CIC) and Certified Risk Manager (CRM) designations.

Now retired from his civic duties, Kieran held elected office for over 20 years as a Trustee on the Village of Seville’s (Ohio) utility board.

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