about cornerstone financial group

Troy has worked as an investment advisor with Cornerstone Financial Group Since 2011 and took the reins as head of the firm in 2020. In January 2023 with the help of his exceptional team, he transitioned Cornerstone into an independent RIA (Registered Investment Advisor). As a fiduciary who always puts his clients’ interests ahead of his own, he has crafted a client experience that is focused on education, modern portfolio theory, and top tier service.

As an advisor, Troy works with executive teams at small and medium businesses to develop employee benefits and executive bonus programs, buy-sell agreements, informal business valuations, and exit strategies. He also enjoys providing wealth management to high-net-worth individuals and families, as well as working with them on estate planning, retirement, and risk-based planning. Troy’s aim is to show as much passion for his clients’ financial futures as they do for themselves, embodying the mission statement of Cornerstone.

Troy originally hails from a town outside of Detroit, MI, but now resides in Combined Locks, WI with his wonderful wife, Charity, who also helps keep the business running smoothly, and his four children, Gracie, Landyn, Fynnian, and Cullyn. Outside of work, he enjoys spending time with family, attending Mason Street Church of Christ, classic cars, boating, fishing, and hunting.

Guy has been in the financial industry since 2013, and he has 25 years experience in business management. He joined the Cornerstone team at the end of 2019. Guy offers a strong focus on financial planning, business planning, income distribution, long-term care, disability income insurance, life insurance, and legacy planning.

In his free time, you can find Guy spending time with his lovely family: Mary, Maximus, and Grace; and whenever possible, hunting and enjoying the outdoors.

Bolan focuses on providing financial strategies to individuals and families who are going through transitional phases in life, such as getting married, having children, buying a home, changing jobs, going through a divorce, or preparing for retirement. He also develops comprehensive and innovative solutions for business owners in order to help them protect their business, their employees, and their personal lifestyle. Bo’s objective is to use financial strategies to help people build and safeguard their assets, so they can be confident knowing they have a plan to work towards reaching their financial goals.

Bolan earned his Finance Degree from the University of Wisconsin Oshkosh. He also has his FINRA series 7 and 66 securities registrations, as well as his Life and Health Insurance License. Bo has earned his blue cord as an Infantryman in the US Army, and he has a 3rd degree black belt in Karate.

Arnold joined Cornerstone Financial Group in December 2021. Born and raised in Chicago by immigrant parents, Arnold learned early in life the value of hard work, perseverance, integrity, and continuous improvement. Before becoming a financial advisor, Arnold enjoyed a successful career in manufacturing, providing tooling and critical components to world-renowned OEMs. He eventually purchased a manufacturing company, and after several years of business ownership and success, decided to sell his business.

Over the years, Arnold has witnessed success. He has also seen the adverse impact of life events on individuals, families, employees, generations, and businesses that were beyond the control or influence of those affected. That’s why his current focus is on empowering his clients to build and protect their nest egg, protect those they care about, live and enjoy the life they dream about, and leave a legacy they can be proud of.

Arnold uses his hands-on experience in the small to medium business world to work with business owners and executive teams in a wide range of areas such as employee benefits, executive/key person strategies, buy-sell agreements, informal business valuations, and succession and exit planning. He also advises individuals and families on financial investments and helps them plan for key events and decisions in their lives, such as marriage and growing/blended families, relocation, education, illness, caring for elderly parents, tragedy, divorce, retirement, and the passing of inheritance to heirs through estate and legacy planning. At the end of the day, Arnold is passionate about helping his clients live a life that is well lived as they work towards their financial goals.

Arnold has the following licenses and certifications: 215 (life, health, annuity), Series 7, 6, 65, 63, SIE, CFP®, ChFC®, AIF®.

When he isn’t working, you’ll often find Arnold spending time with his family and two German Shepherds, watching or refereeing soccer, playing tennis or golf, exercising, dining, traveling, and more.

Charity started working for her husband, Troy Leonard, in 2015, splitting her time between the office and their home. In the office, Charity manages the day-to-day operations, supports staff, and assists with any client-related services if needed. When she’s at home, Charity takes care of their four kids and two dogs. Charity and Troy enjoy their time with their family, being outdoors, and any chance they get to go on dates. Charity also enjoys listening to Christian music whenever she can, doing art, and shopping at antique or thrift stores.

Mary started working for her husband, Guy McCauley, in 2015. She assists Guy in setting up client meetings, processing paperwork, organizing events, and helping with whatever else is needed in the office. When she’s not helping Guy in the office, Mary enjoys spending time with their two kids, traveling, volunteering at church, cooking/baking, and hanging out with friends.

Chelsy joined Cornerstone Financial Group in 2020. Prior to joining Cornerstone, she spent nine years working for an insurance company in the health and wellness department. At Cornerstone, Chelsy assists with client-related services such as processing paperwork and managing client requests. At home, she enjoys spending time with her husband and three kids, along with their rescue dog. She also enjoys gardening, baking, traveling, and going for walks.

Greg joined Cornerstone Financial Group in October 2025, bringing with him a professional background in healthcare and a strong commitment to service. Prior to joining Cornerstone, Greg worked as a nurse in Madison and later dedicated several years to being a stay-at-home parent raising his four children.

At Cornerstone Financial Group, Greg manages front desk operations, including welcoming clients, coordinating appointments, answering inquiries, and providing administrative support to the advisory team.

Greg lives in Oshkosh with his wife, Natasha, their four children, and their cat, Nala. In his spare time, he enjoys planting trees, woodworking, learning about space, and reading about Theodore Roosevelt.

Jesse relocated from southeast Michigan to join Cornerstone in March of 2014, working as an advisor alongside Troy Leonard. He took a hiatus in 2017 to pursue other opportunities, serving as an investment consultant for Scottrade and then as a financial advisor to clients in all 50 states as part of the Virtual Advice Team at Thrivent.

Jesse happily rejoined Cornerstone as paraplanner in 2023, retaining his FINRA Series 7 and 66 securities registrations and multiple state insurance licenses, to assist Troy and other advisors through research, data analysis, financial plan development, and streamlining client requests.

Jesse lives in Appleton with his brilliant wife, Autumn, their young daughter, Gemma, and a very cuddly housebroken pony (allegedly a Great Dane-boxer mix dog) named Thor. In his free time, Jesse enjoys camping with family, reading, writing speculative fiction, and playing Dungeons & Dragons with friends.