Jeffrey Judge

Jeff Judge, CFP®, ChFC®, CLU®, AEP®, is Managing Partner of Chesapeake Financial Planners in Forest Hill, Maryland.

He helps families, executives, and business owners navigate retirement, business exit, equity compensation, tax, and estate planning through the firm's proprietary R.U.D.D.E.R. Method™ — a structured six-step process for aligning wealth with life goals. A 2005 graduate of Goucher College, Jeff began his career in regional and national banks before joining MetLife in 2011 and founding his first firm a year later. He co-founded Chesapeake Financial Planners with Mark Rossbach, CPA, in 2017. Jeff is a Kiplinger contributor, a Five Star Wealth Manager (2017–2026), and an NAEPC-affiliated estate planner. He leads financial-literacy workshops for Fortune 500 and mid-sized employers across the Mid-Atlantic. Jeff lives in Forest Hill with his family. Securities offered through LPL Financial, Member FINRA/SIPC. Advisory services through Great Valley Advisor Group, a separate RIA. You’re smart, successful, and used to figuring things out. But when it comes to your finances, especially during a big life shift, it can feel like too much. Business sales, inheritance, retirement, divorce, career pivots...these are high-stakes transitions, and they don’t come with a playbook. The decisions are complex. The tax implications are murky. And everyone seems to have an opinion. You want clarity, not more noise. You want a partner who speaks your language, respects your intelligence, and knows how to turn complexity into a clear course of action. That’s where we come in. As fiduciary advisors with both CFP® and CPA credentials, we integrate tax-smart planning with real-world financial oversight. No products to push. No confusing jargon. Just data-backed advice tailored to your life. We use our R.U.D.D.E.R.™ method to help you make better decisions, avoid costly missteps, and stay accountable to the life you actually want, not someone else’s script. Our job isn’t to impress you with acronyms. It’s to simplify, clarify, and walk beside you through every major decision, so you can move forward with confidence.