January 25, 2026

How a ‘perpetual’ stock trick could solve Michael Saylor’s $8 billion debt problem

The bitcoin treasury firm is using perpetual preferreds to retire convertibles, offering a potential framework for managing long-dated leverage.

Author: James Van Straten

Ty Sagalow's unique background in legal, underwriting, policy drafting and claims – and his designation as a “qualified insurance expert” by the United States District Court for the Southern District of California – offers attorneys an unparalleled resource in D&O, E&O and Cyber insurance coverage disputes. He was also named "Most Helpful Expert" in a recent $8.7M coverage decision.

Mr. Sagalow served as Chief Underwriting Officer and General Counsel for AIG Executive Liability (formerly National Union Fire Insurance Company of Pittsburgh, PA), the world’s largest carrier of Directors and Officers Liability and Professional Liability Insurance. As General Counsel, Mr. Sagalow personally wrote or led teams that wrote all the D&O policies and many of the professional liability policies that AIG produced between 1988 and 2000 – policies which continue to serve as the foundational wording for the D&O and professional liability policies in the market today. As AIG Executive Liability’s Chief Underwriting Officer, Mr. Sagalow was charged with all underwriting interpretations and decisions for AIG D&O/E&O policies. In 2009, Mr. Sagalow headed up the team that rewrote all D&O policies for Zurich North America.

Ty is a cum laude graduate of Georgetown University Law Center and holds a LLM from New York University School of Law.

Combining his talents as a network security insurance expert and an insurance product development expert, Ty Sagalow is the leading expert on the unique risk and insurance needs of the bitcoin industry.

With the successful sale of BitSecure(tm), the first bitcoin theft insurance policy in February of 2015, he is the first to create a sustainable, robust insurance policy to cover the theft of bitcoins and other virtual currency backed by an A-Rated, global “top 10” Property and Casualty insurance company.

Innovation Insurance Group is an insurance consulting firm and insurance brokerage founded by 30-year insurance executive, Ty R. Sagalow, former Chief Underwriting Officer, General Counsel and Chief Innovation Officer at AIG, and former Chief Innovation Officer at Zurich, NA and Tower Group. IIG focuses on three core practice groups: product development, expert witness services (primarily in the Management and Professional Liability areas), and bitcoin industry brokerage services.

Learn more about Ty R. Sagalow
Learn more about Innovation Insurance Group
Learn more about InsurTech Consulting
Learn more about Bitcoin Insurance Agency

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The Future of Insurance (with Bryan Falchukc) (Video Podcast Aug 2022)
InsurTech Ohio Spotlight with Ty Sagalow (Podcast 5/10/22)
Meet the Godfather of Insurtech… (The Insurtech Leadership Podcast)(12/20/21)
Why Insurance Industry needs Lemonade Insurance-Style Business Models (Silicon Review, 2019)
CIIA Conference: Innovation, Culture and Technology
May 13, 2021, Chili (Virtual)
Latin American Conference New Perspectives and Innovations for the Future of Insurance
Nov 4, 2019, Mendoza, Argentina
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How a ‘perpetual’ stock trick could solve Michael Saylor’s $8 billion debt problem

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