Meet Our Founder
The Crumdale Family Office led by Crumdale Specialty Founder, Chairman, and CEO, Matthew Naylor, employs a holistic approach to investment.
Matthew Naylor is the Founder and Chief Executive Officer of Crumdale Specialty and a seasoned entrepreneur and insurance executive with a proven track record across the insurance industry. Throughout his career, he has built, scaled, acquired, and led high-growth businesses, with a focus on strategic growth, operational excellence, and long-term value creation.
His expertise spans employee benefits, risk management, MGAs, MGUs, reinsurance, and mergers and acquisitions. Prior to founding Crumdale Specialty, Matthew led the growth and acquisition of multiple insurance-related businesses at Elite and later served as Chief Executive Officer and President of the Accident and Health Division of Houston International Insurance Group.
Matthew has also played a significant role in the development and growth of several high-performing ventures, including Syndra Capital Partners, Leverage Health Solutions, and Health Insurance Innovations (HIIQ). His accomplishments have earned notable recognition, including Ernst & Young LLP’s Entrepreneur Of The Year® Award in 2020, inclusion in the Philadelphia Business Journal’s 40 Under 40 and the AIM Institute for Learning and Research Leadership award in 2025.
In addition to his professional achievements, Matthew is the Founder of the Crumdale Family Office and has served on numerous public, private, and nonprofit boards. He currently serves as Chair Emeritus of AIM Academy and formerly served on Drexel University’s Board of Trustees. His leadership is distinguished by entrepreneurial vision, and a longstanding commitment to creating meaningful and enduring impact.
Jake Willcox
President & Operating Partner
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.
Ed Garno
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.
The Team
Mandy DiIenno
Paul Bredickas
Stephanie Unger
Reid Ljungholm
Peter Garno
