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 earned his undergraduate degree from the University of Illinois with a concentration in computer engineering and mathematics. He received his MBA with a concentration in Finance from the University of Illinois. He holds the Chartered Financial Analyst (CFA), Certified Financial Planner™ (CFP®), and Financial Risk Manager (FRM) designations.
Craig Stapleton is an experienced investor with over 20 years of market analysis expertise. In 2022, Craig retired as Chief Investment Officer of Securian Asset Management to leverage his wealth of knowledge and skills in the private wealth sector. As an institutional investor, he spent over a decade managing $50 billion of assets for the Fortune 500 insurance company. His focus was on retirement income solutions, risk management, and equity stabilization strategies that help investors sleep easy. Through his uniquely designed and flexible hedging strategies in tandem with his effective management of asset allocation, Craig exceeded growth and performance benchmarks to grow Securian Financial into becoming one of the largest 500 companies in the United States.
Upon his retirement 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 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
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) designation. He is currently pursuing the CFP® certification, having completed all the education requirements through a CFP Board-registered program and now preparing to sit for the final exam in the coming months.
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 two dogs, Ike and Reggie. The entire family is eagerly awaiting the arrival of their baby boy this December. A new chapter filled with anticipation and joy.
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.