Meet Our Founder
The Crumdale Family Office led by Crumdale Specialty Founder, Chairman, and CEO, Matthew Naylor, employs a holistic approach to investment.
Matthew founded Crumdale Family Office with a passion for innovation and a commitment to excellence. With extensive experience in employee benefits, risk management, MGAs, MGUs, and reinsurance services, Matthew brings a wealth of industry expertise to our team.
Throughout his career, Matthew has demonstrated a unique ability to identify opportunities for growth and development. He has led multiple industry-related businesses to success, leveraging his distinctive leadership approach and deep industry knowledge to drive sustainable growth.
Matthew’s dedication to excellence extends beyond his role at Crumdale. He is an active member of the Young President’s Organization (YPO) and has served on public, private, and nonprofit boards. Recognized as the Entrepreneur of the Year in 2020 by Ernst & Young LLP (EY US), Matthew is a driving force in the industry.
Jake Willcox leads Crumdale’s global sales strategy, bringing over 15 years of experience across insurance, healthcare, and financial services. He is a founder, investor, and operator with a track record of building and scaling businesses in complex, regulated markets.
Jake joined CEO Matt Naylor in 2014 to help launch Crumdale Specialty, where his vision and leadership have been instrumental in shaping the firm’s growth and broader ecosystem. He is known for combining strategic insight with disciplined execution, driving revenue growth while building high-performing teams and long-term partnerships.
Jake is a Founder and General Partner of Syndra Capital Partners, where he invests in and partners with companies across the insurance, healthcare, and financial services landscape. His experience spans the full business lifecycle—from early stage development to scaled operations—across investing, organizational strategy, and performance optimization.
Jake is an active member of the Young Presidents’ Organization (YPO), including YPO International, reflecting his commitment to leadership development and global collaboration.
He earned a B.A. in International Business from Loyola University, where he was a four-year varsity athlete, Dean’s List student, and university ambassador. He remains actively engaged with the university and broader community.
Jake Willcox
President & Operating Partner
Ed Garno is a seasoned entrepreneur, investor, and business builder with a distinguished track record of scaling companies across the insurance, employer health, and financial services sectors.
He was a founding principal of Trion, a Philadelphia-based firm that helped transform the employee benefits landscape through innovation in client service and technology. Under his leadership, Trion grew into one of the nation’s largest privately held benefits firms prior to its acquisition by Marsh & McLennan Companies in 2010.
In addition to his operating experience, Ed serves on the board of Crumdale Specialty, and is a Founder and General Partner of Syndra Capital Partners. He is also a board member of 1251 Capital Group, Lio Insurance Company, and Mint Eco Car Wash, and remains an active investor across real estate development and insurance-related ventures.
Earlier in his career and continuing today, Ed has served on numerous corporate and nonprofit boards, including Bryn Mawr Hospital and the University of Virginia Athletics Foundation, reflecting his longstanding commitment to leadership, philanthropy, and community engagement.
He is also the founder of Padelphia, a community-focused platform promoting connection, fitness, and engagement through racquet sports.
Ed Garno
Operating Partner
The Team
Mandy DiIenno
Paul Bredickas
Stephanie Unger
Reid Ljungholm
Peter Garno
