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Ryan Specialty
Ryan Specialty built a $3 billion business around the risks ordinary insurance markets would rather not touch. Its real product is a carefully engineered meeting between difficult exposures, specialist judgment and willing capital.
UFG Insurance
For 80 years, the Cedar Rapids carrier behind the interlocking-U logo has insured contractors, shopkeepers and factories the unglamorous way - one independent agent at a time.
Ledgebrook
Ledgebrook is a tech-enabled excess and surplus (E&S) lines managing general agent (MGA) that aims to give wholesale insurance brokers the fastest, easiest quoting experience. Founded in 2021 by former actuary Gage Caligaris, the company pairs a next-generation tech stack - which enriches and prefills broker submissions and speeds rating - with experienced human underwriters to write specialty commercial coverages such as general liability, excess liability, professional liability, allied healthcare, and architects & engineers. Having written its first policy in May 2023, Ledgebrook passed a $100M premium run rate and closed an oversubscribed $65M Series C in June 2025, bringing total funding to roughly $119M.
Gage Caligaris
Gage Caligaris is the founder and CEO of Ledgebrook, a tech-enabled managing general agent (MGA) modernizing the Excess and Surplus (E&S) specialty insurance market. A Harvard-trained applied mathematician and former Barclays commodity derivatives trader, he spent eight-plus years as an actuary at Liberty Mutual, where he became the fastest person ever to pass the Casualty Actuarial exams and later scaled a new-mobility products line from under $50M to over $450M in gross written premium. He founded Ledgebrook in 2022 to pair modern engineering with deep insurance expertise, reaching a $100M run rate in under two years and raising an oversubscribed $65M Series C in 2025. In 2026 he was named an EY Entrepreneur Of The Year New England Award winner.