About Mainstay Financial Group 


Being an independent financial advisory firm allows us to serve you in very unique ways. As a fiduciary, we have the responsibility to place your personal financial needs before anything else. We do this by educating you with specific information so you can determine what is best for your unique and individual financial plan. We also have developed partnerships with CPA’s, Enrolled Agents, and attorneys and can refer you , as needed, to further help guide you through the maze of retirement and estate planning.

Our goal is to do what is best for you today and for your heirs in years to come by helping you achieve the peace of mind that comes with knowing that you have been educated and taken action on the road to financial security.

The Mainstay Core

Mainstay Financial Group offers advocacy and personal financial guidance, in a caring environment, where you learn about choices available to you in
your particular situation. We believe your financial plan should be as unique as you are.

We will always treat you with respect, care and warmth. We will inform you clearly, and patiently allow you the time you need to make good decisions. We will explain things in ways you understand and the reasons behind our suggestions.

We dedicate ourselves to exemplary service and caring relationships, focusing on helping clients arrive at clear, straightforward answers.


Bob Beargie

Investment Advisor Representative

Bob has guided his clients and served as a fiduciary to families and individuals through the inflationary and high interest rate environment of the 1980’s and 1990’s, the technology bubble of the early 2000’s, the financial crisis and subsequent real estate bust of 2008, and, most recently, through the COVID-19 global pandemic of 2020. Bob enjoys working with his clients and their families; learning, preparing, and helping them define their needs and wants, their hopes and dreams; helping them accomplish their long term goals and objectives; and, through careful one-on-one planning and providing specific solutions, prepare them for their future and encourage them to enjoy the journey.

Bob grew up in Lexington, Kentucky and attended the University of Kentucky and St. Thomas More University, earning degrees in both Economics and Business Administration. In 1988 Bob graduated from the University of Louisville School of Law and practiced law, primarily in the area of wills, trusts and estate planning. In 1991 he earned his MBA from the University of Miami and moved to Cleveland, Ohio to serve as a corporate fiduciary in the trust and wealth management industry. In 1998, Bob and his growing family of seven left the Midwest and moved South to the Gulf Coast, where he continued to serve as a fiduciary and investment advisor in the wealth management industry.

Bob was fortunate to grow up surrounded by the selfless love, affection and support of his parents, who instilled in him and his four siblings a strong work ethic and an appreciation in the value and beauty of providing for one’s family. In his professional career, he was also fortunate to find a business partner in Annalee Leonard who shared these same values; who challenged and supported each other, expanded their level of service above and beyond traditional delivery channels, and perform their craft at the highest and most professional level possible.

Bob learned early on that it is not solely about investment returns and what you make; but more about what you get to keep and pass on to your family, your loved ones, and the causes you believe in. With over 30 years of investment and wealth management experience, Bob brings a unique perspective and value to his clients with his extensive background in law, taxation, and retirement and estate planning. He considers it an honor and a privilege to serve his clients. It is a vocation, passion project, and a tremendous responsibility that he does not take lightly. It is Bob’s most sincere goal and professional objective to exceed his clients’ expectations in all matters; to earn their trust and confidence in him every day; and to continue to serve his clients and their families in the most caring, compassionate and professional manner he knows.

Outside the office, you can find Bob and his wife, Connie, on long walks with their dog, Luna, or on a sightseeing bike ride in one of many historic towns along the Gulf Coast. They enjoy dining on all types of seafood and authentic Mexican foods. Bob and Connie also enjoy road trips up North and out West to visit their seven children and three grandchildren.

Hillary Hughes

Office Manager

Hillary Hughes became the Office Manager at Mainstay Financial Group in April 2021. She manages the relationships between each client and their advisor. That relationship between the advisor and their client is what sets Mainstay Financial Group and Hillary apart from other firms. They know that building ongoing trust happens when you take time to get to know each client personally, not by focusing on the Financials.

Hillary has been in the Financial industry since 2011, working as an Office Relationship Manager, so she knows how to
discern what’s important to each client. She keeps files updated, sets appointments, and keeps clients informed of significant account changes. Hillary is also the point of contact when advisors need information for both clients and prospects. Long before joining Mainstay Financial, she was a turbine engine mechanic on Chinook helicopters in the U.S. Army.

Hillary grew up in Ohio in a time when it was safe to leave your doors unlocked, and electronics were only futuristic movie ideas. Her parents instilled in her a strong work ethic and enough self-confidence to know she can make a difference in these challenging and changing times. Hillary stakes her work and personal reputation on faith, honesty, and trust.

Hillary has been married to Bob since 1978, and together they have three wonderful sons. Each son is married, which has graced Hillary and Bob with ten grandchildren! They enjoy traveling the world, with Uzbekistan and Israel being Hillary’s favorite places to visit. She and Bob also lead mission trips—each one providing a lasting impression and a host of incredible memories.