About us
Robert Cantwell III & Roman Puglise
Leadership
Robert Cantwell III
Founder and Chief Investment Officer
robert@upholdings.com
Robert founded Upholdings after years as both an investor and operator. He witnessed smart, well-compensated people make costly mistakes with their equity, taxes, and estate. Not because they didn't care, but because the three weren't being managed together. He started Upholdings to fix that.
A recognized leader in active investment management, Robert previously managed the Compound Kings fund. Before that, he served as the CFO of Everlane during its period of hyper-growth.
He graduated with an AB in Economics from Harvard College, with honors. He lives in Nashville with his family. He currently enjoys playing tennis and is accepting any local challengers.
Roman Puglise, CFP®
Partner and Lead Financial Planner
roman@upholdings.com
In Upholdings, Roman saw an opportunity to bring the ultra-high net-worth approach to those still building, in a more hands-on and aligned way. Not just managing assets, but leading the financial planning conversation and guiding decisions across every aspect of a client’s financial life.
Roman’s early career centered around advising ultra-high net-worth families in a large independent RIA, where wealth management operated like a personal family office - integrating estate, tax, and investment decisions.
A former professional athlete for the Maryland Whipsnakes and National Champion and former All-American lacrosse player at the University of Maryland, Roman brings a leadership-driven, team-first mindset to every client relationship.
Roman holds a BS and MS in Finance and is a CERTIFIED FINANCIAL PLANNER™ professional. He lives in Charleston with his wife, Teresa, and their son, Gianni. Outside of work, he enjoys golfing, spending time at the beach, staying active, and training the next great athletes.