Cynthia Kelley

Charles Kern is a financial advisor with Pilot Investment Services, LLC in Greensboro, NC. He holds Series 63 and Series 65 licenses and has 32 years of industry experience. Outside of his advisory role, Kern works as an auditor for the Department of Treasury in Charlotte, NC. Pilot Investment Services is a single-advisor registered investment adviser serving individuals, high-net-worth clients, trusts, and estates. The firm provides discretionary portfolio management and limited financial planning, focusing on individualized investment plans implemented through ETFs, stocks, bonds, and options.

We’re built for families! We focus on bridging generations to connect families and their finances. As Baby Boomers, you created more wealth than any generation before you. Now in your retirement years, the economic expansion that aided your careers doesn’t feel as robust. You worry about your savings lasting a lengthy life expectancy. You also worry that your children and grandchildren will be the first generation to not have it better than the generation before them. Our goal is to solve both problems. Our structure allows us to provide the same great advice whether you have a lifetime of savings or you are just starting out. That means we can work with multiple generations, and where appropriate, find opportunities to coordinate across generations while maintaining privacy and independence. I am a millennial myself with over a decade of experience helping retirees with personal finances. That combination of youth and experience gives me an advantage over many of the advisors out there. My youth, to retirees, means I am likely to be around for the entirety of your retirement. All those plans you made with your advisor, will be executed by the advisor that helped you plan them. If that includes an inheritance, good news because I want to work with your heirs too! To a younger generation, you get an advisor you can relate to who doesn’t treat your problems as less significant because you don’t have the same level of assets. Just because I’m young, doesn’t mean I’m green! I was previously the Practicing Partner of a wealth management firm focused solely on retirees. As the lead portfolio manager, I oversaw almost $500 million in client portfolios. That experience means I’ve guided and advised clients through every stage of a successful retirement. It also means I know what a successful retirement looks like. As I’ve always said, best laid plans begin with the end in mind, so my experience serves just as well early in your journey to financial independence. I started my own firm because I saw an increasing need to reconnect families and their finances. Grandparents are providing child care, children are providing elderly care, and everyone is chipping in to pay for education. As much as ever families need each other, and our program is specifically designed to be prepared when they do.

Mike took a different path, and every stop along the way shaped how Legs Financial works today. Mike started as a high school physics teacher, where he learned to take genuinely complex ideas and make them clear and actionable for people who had never encountered them before. That skill never left. Years at Vanguard grounded his investment philosophy in evidence, low cost, and long-term discipline. Working with advisors across a multi-state territory at LPL gave him a front-row view of the wide range of practices and offerings in the industry, what worked, what didn’t, and what was missing. Time at a tech startup sharpened his eye for the tools that actually help clients. And a stint at a trust company gave him firsthand experience in trust administration, the kind of operational depth that most advisors simply don’t have. The pattern across all of it: every role added a layer. And when it came time to build his own firm, he couldn’t reconcile the standard model. Charging someone twice as much simply because their portfolio had grown, even when the work hadn’t changed, felt fundamentally misaligned. So he changed the model. Legs Financial operates on a transparent flat fee, quoted upfront based on the complexity of your situation, not the size of your portfolio. Mike earned his ChSNC® (Chartered Special Needs Consultant) designation specifically to offer deeper expertise and better support to families navigating Special Needs Trusts, Achieving a Better Life Experience (ABLE) accounts, and the long-term coordination required to plan for two lifetimes. For him, it isn’t just a credential, it’s a commitment to carrying the heavy pack for families protecting a loved one’s quality of life. Mike and his family moved to North Carolina in 2003, settling in the Lake Norman area before relocating to Greensboro in December 2021. Outside the office, he volunteers as lead for Abilities Tennis in Greensboro, serves on the board of the Guilford Regional Tennis Association (GRETA), leads new Blind and Low-Vision tennis clinics, sits on the Mayor’s Committee for Persons with Disabilities, serves as Operations Lead for the Winston-Salem Open professional tennis tournament, and offers educational seminars to organizations across the area.

Michael Brown is a financial advisor at Olde Towne Financial Management Co. in Greensboro, NC, with 28 years of industry experience. He holds a Series 66 designation and has worked at Olde Towne Financial since 2017, following eight years at Invest Financial Corp. Olde Towne Financial Management Co. offers investment management and financial planning services primarily to individual clients, focusing on tailored portfolios and ongoing advisory contact. The firm manages discretionary accounts guided by client objectives and delivers written financial plans that address clients’ overall financial situations.

Travis Ray is a CFP® professional with three years of experience, currently serving as the sole advisor at BY Design Financial Planning in Greensboro, NC. He previously worked at Envestnet for ten years and owns By Design Consulting Services, LLC, a software consulting business. BY Design Financial Planning serves individual and high-net-worth clients with fee-only investment management and comprehensive financial planning, emphasizing asset allocation and passive investment strategies. The firm typically manages discretionary portfolios tailored to client goals and risk tolerance and uses technology to advise on held-away accounts.

Jamal Brooks is the principal of J. Brooks & Company, LLC in Greensboro, NC, holding a Series 66 designation with 15 years of industry experience. He has led his independent advisory firm since 2011. In addition to his advisory role, Brooks works as an independent insurance agent specializing in life insurance, annuities, and long-term care insurance. J. Brooks & Company, LLC provides portfolio management and financial planning services to individuals, high-net-worth clients, investment groups, and family offices. The firm combines fundamental and technical analysis in its investment approach and tailors financial plans to clients’ specific life stages and goals.