Dan Shepard

I founded Oak Road Wealth Management in 2016 after spending years in the financial industry
and realizing there had to be a better way to serve clients. Throughout my career, I saw a lot of advisors focused on products and performance, but not enough focused on helping people truly understand whether they were going to be okay financially.

I wanted to build a firm that gives people confidence — confidence that they can retire, confidence that they can do the things they want in life, and confidence that the numbers actually support the life they envision. For me, financial planning has always been about more than spreadsheets and investment returns. It’s about sitting down with people, understanding what they want their life to look like, translating those goals into dollars and decisions, and helping them feel secure enough to enjoy the life they’ve worked hard to build.

I grew up on a farm in central Missouri, raising hogs and cattle and baling hay. Farm life taught me the value of hard work at an early age, but it also taught me patience — the importance of investing time, effort, and money into something long before you see the payoff. Those lessons have shaped both my life and the way I work with clients today. I attended the University of Missouri-Columbia, where I earned a degree in Agricultural Economics. After college, I moved to New York City to begin my career as a financial advisor with Morgan Stanley.

Living and working in New York taught me grit and resilience. From there, I joined Oppenheimer Funds for a couple of years before eventually moving back to Kansas City as a mutual fund wholesaler for American Century Investments. American Century later promoted me to Vice President and Territory Sales Manager, which took my family and me to Nashville, Tennessee for five years. Throughout those roles, I had the opportunity to work alongside advisors across the country and see firsthand how different firms served their clients — the things I admired and the things I believed could be improved.  

Those experiences ultimately helped shape the vision for Oak Road Wealth Management. After Nashville, my family and I moved back to the Kansas City area and purchased a 22-acre farm in Lee’s Summit, where we still live today.

My wife and I have a blended family with seven children, so life is busy in the best possible way. Between sports, music, school activities, and managing the farm, there’s rarely a quiet moment around our house. The farm itself has become another passion project.

Over the years we’ve raised bees, produced honey, baled hay, had goats and chickens, operated a pumpkin patch, and even added a small Airbnb guest house on the property. We’ve also spent years renovating the old farmhouse and continually improving the property. I’ve always enjoyed building things, staying busy, and working toward meaningful long-term goals — whether that’s on the farm, in business, or helping clients plan for their future.

One of the most rewarding parts of my work is seeing clients gain the confidence to do things they once thought might not be possible. Sometimes it’s retiring earlier than they expected. Sometimes it’s upgrading a home, buying a new car, traveling more, or simply enjoying life without constant financial stress. Helping people reach that point of clarity and confidence is why I started this firm and why I still love what I do today.

Outside of work and the farm, one of my personal passions is kayak racing. In 2020, I completed the MR340 — a 340-mile kayak race from Kansas City to St. Louis — finishing in 491⁄2 hours and earning membership in the “50 Hour Club.” It was one of the most physically and mentally demanding things I’ve ever done, and an experience that reinforced the importance of endurance, discipline, and persistence — qualities that apply just as much to life and financial planning as they do to racing.