Caleb Riley

John Cunningham is a native Louisvillian and a sixth-generation Kentuckian. He believes a successful client partnership is built upon two key principles: putting clients’ interest first and providing exceptional personal service. He has built his reputation as a trusted advisor by serving his clients with integrity and honesty and becoming their primary resource for family finances. His process focuses on creating lasting income streams for their clients to facilitate their desired lifestyle and creating the discipline and time horizon necessary for risk assets to perform. Three distinct categories John emphasizes with clients are cash management, wealth management, and family legacy planning. He strives to meet the complex, ever-changing, and often unique, needs of families with wealth. Throughout his career, John has demonstrated a strong commitment to both community and the arts. He serves on the board of the Louisville Orchestra, Assumption High School Investment Committee, is an Elder at Second Presbyterian Church, and is an active member of the Rotary Club of Louisville and the Financial Planning Association.

Elijah has been a fee-only financial planner for over eight years. In 2025, he started Essa Financial to provide transparent and client-centric financial advice to folks in the Louisville community and beyond. As a teacher, Elijah’s favorite part about being a financial planner is communicating complex planning topics to clients in ways that are more easily understood. He enjoys the education aspect of being a planner, especially in a one-on-one environment. He values deep relationships with clients, and is always willing to listen and learn. He also believes exceptional client service (and swift communication) is the cornerstone of financial planning. Elijah is actively involved in the profession. He is an active volunteer with the National Association of Personal Financial Advisors (NAPFA), having previously served on their Genesis board for young advisors for five years and currently serving on the South Region board as the Membership Chair. He also reviews scholarship applications for the CFP Board Center for Financial Planning, which provides assistance to qualified candidates for the CFP® exam. In addition to his role as a planner, Elijah teaches part-time as an adjunct professor at the University of Louisville. Elijah resides in Louisville with his wife, Sarah, and dogs, Landon and Korra. Aside from financial planning and teaching, Elijah spends his time frequenting local coffee shops, running (short distances) around his neighborhood, playing video games, watching the Minnesota Timberwolves, and of course, spending time with friends and family.

Mark Thompson is the sole advisor at MARK Investment Advisors in Louisville, KY, with 15 years of industry experience. He previously operated Thompson Investment Advisors for 35 years before establishing his current firm. Outside of advisory work, he is a minority owner of Whitecloud Technologies, LLC, a company involved in medical spine device inventions and marketing. MARK Investment Advisors provides investment counsel and portfolio management services to individuals, retirement accounts, pension and profit-sharing plans, trusts, estates, charitable organizations, and corporations. The firm combines technical chart analysis, mathematical measures, and fundamental review to guide investment decisions and may adjust cash allocations to preserve capital during market declines.

Matthew Doyle is a financial advisor at Trimingham Financial with 10 years of industry experience. He holds a Series 66 designation and previously worked at Northwestern Mutual Wealth Management Company. Outside of his advisory role, he maintains a bookkeeping client and works as a warehouse associate for Amazon. Trimingham Financial provides financial planning and investment management services primarily to individual clients. The firm focuses on asset allocation using exchange-traded funds and offers both discretionary and non-discretionary management.

Jeb Jarrell is a CFP® credentialed financial advisor with 10 years of industry experience. He is the sole advisor at Plentiful Wealth, LLC in Louisville, KY, and has previously worked at Ameriprise Financial Services, Render Capital, Merrill, and Commonwealth Financial Network. Outside of his advisory work, he hosts "Two Glasses of Bourbon," a podcast about Kentucky history and culture, and serves as Treasurer and Board Member of St. John Center, a nonprofit providing housing services to the homeless. Plentiful Wealth is a boutique registered investment adviser serving individuals, high-net-worth clients, nonprofits, and employer/business clients. The firm offers comprehensive financial planning, discretionary portfolio management, and specialized outsourced CIO services for nonprofit endowments, combining fundamental analysis with modern portfolio theory to manage client portfolios.

Anita Loy is a CFP®-certified financial advisor with 23 years of industry experience, currently practicing at Inspire Private Wealth Management. She previously worked for Money Concepts Capital Corp and has been involved with Inspire Executive Operations since 2013. In addition to her advisory work, she teaches and coaches adult education courses at various colleges and universities. Inspire Private Wealth Management serves individuals, business entities, trusts, estates, charitable organizations, and retirement plans through discretionary investment management, retirement plan consulting, and financial planning. The firm focuses on customized portfolio allocations using equities, fixed income, mutual funds, and ETFs, and also provides services to corporate and institutional plan sponsors, including ERISA fiduciary responsibilities.