Our Philosophy
We want you to succeed in meeting your financial goals. As a fee only registered investment advisor (RIA) we are aligned with your success. This means that our firm is required to act and serve each client’s interests at all times. No commissions. Full transparency. Stapleton Asset Management is registered in Tennessee, Illinois, & Minnesota, but is happy to have clients from across the country. Each individual and institution has specific sets of goals and risk tolerances which cannot be addressed by robo-advisors or commission focused firms. We want to create financial, investment, tax and estate strategies that are customized to confidently meet long-term goals while providing stable performance and strong income today.
Craig Stapleton CFP®, CFA, FRM
President & Chief Investment Officer
Craig Stapleton spent nearly two decades in institutional asset management, most recently as Chief Investment Officer of Securian Asset Management, one of the largest Fortune 500 insurance companies in the United States, where he oversaw more than $50 billion in assets. His institutional focus encompassed retirement income solutions, derivatives-based hedging strategies, equity stabilization, and disciplined asset allocation across complex market environments.
In 2022, Craig made a deliberate transition to private wealth management, founding Stapleton Asset Management to bring institutional-caliber investment discipline to individual investors. The rigor, risk awareness, and strategic depth that institutions demand are rarely accessible to private clients; that gap is precisely what Stapleton AM is designed to close. Upon his exit from institutional investing, Craig is enthusiastic about bringing his skills and expertise into the lives of individual investors. He is passionate about facilitating your financial goals through investment, retirement income, tax, estate and risk mitigation strategies.
Craig holds the Chartered Financial Analyst (CFA), Certified Financial Planner™ (CFP®), and Financial Risk Manager (FRM) designations. He earned his undergraduate degree in computer engineering and mathematics and his MBA in Finance, both from the University of Illinois.
Craig has served on the Board of the Saint Paul and Minnesota Foundation. He has also served on the Investment Committee for the Minnesota Historical Society.
Craig resides on his hobby farm in Leipers Fork, Tennessee with his wife and four young children.
Josh Grass, CFA, CFP®
With over a decade of hands-on experience in financial services, Josh Grass is known for blending technical expertise with a deeply personal approach. He earned his bachelor’s degree in Finance from the University of Saint Thomas in Saint Paul, Minnesota. Josh is a proud holder of the Chartered Financial Analyst (CFA) and the Certified Financial Planner® (CFP®) designation.
Josh’s career began in the corporate world, where he was tasked with leading ambitious projects: Enterprise-wide technology transformations, streamlining business processes, and even helping to launch entirely new ventures. It was here that Joshua saw just how transformative clear strategies and disciplined execution could be, not only for organizations but for individuals as well.
He believes that managing wealth is about more than just numbers: it’s about aligning financial decisions with broader life and career aspirations. This approach resonates especially with young professionals and families juggling career growth, family needs, and future dreams. Josh’s clients appreciate how he translates complex concepts into simple, actionable strategies, always tailored to their unique circumstances.
Outside the office, Josh’s life is equally dynamic. He and his wife, Haley, live in Delano, Minnesota, with their newborn son, Beaux, and their two dogs, Ike and Reggie.
Whether he’s helping a young couple secure their first home, optimizing investment strategies for growing families, or building relationships that last for years, Josh is committed to turning financial clarity into confident action. For Josh, every client’s journey is unique—and he’s honored to be a trusted partner every step of the way.