Richard E Wilson II APMA®, AIF® CPFA

I started my career as a financial advisor with a mission that still drives me today: helping people live life by design—not by default. For over two decades, I've had the privilege of working with individuals, families, and businesses to transform the complex world of finance into something understandable and actionable. My goal has never been just to help clients make a living—it's to help them build a life that reflects their deepest values and aspirations.

What sets my approach apart is my belief in managing lives, not just money. Every financial decision should move you closer to the life you want to live, and every strategy should align with your personal values, goals, and the legacy you want to leave behind. This philosophy has guided my work in comprehensive financial planning, investment management, and retirement strategies for families across the country.

As an advisor and part of the investment committee here at Pilot Rock, I focus on building portfolios that balance risk tolerance with visionary opportunities. I'm particularly passionate about identifying what's next—my current research explores the Fourth Industrial Revolution and the wealth-building potential in artificial intelligence, robotics, and the space economy. I believe that understanding and investing in innovation will be a key driver of long-term wealth creation for our clients.

My passion for finance actually began with a gift from my grandmother, who bought me my first stock when I was just a child. That early introduction to investing sparked a lifelong belief in the power of financial literacy and generational wealth. Today, I help families not only manage their wealth but build multi-generational legacies through thoughtful planning and hands-on education. There's something deeply satisfying about empowering families to pass down financial wisdom along with their assets.

I hold a B.A. in Business Administration & Marketing and maintain several industry credentials, including Accredited Investment Fiduciary (AIF®), Certified Plan Fiduciary Advisor (CPFA®), and Accredited Portfolio Management Advisor (APMA®). I was honored to receive the Five-Star Wealth Manager Award* in 2025, and I'm proud that our team has been recognized by Forbes** as one of Oregon's top wealth management teams in both 2024 and 2025.

Beyond my professional life, I'm deeply committed to our community. I founded the Friends of the Josephine County Fairgrounds, serve on the Board of Directors for the Boys & Girls Clubs of the Rogue Valley, and at my local church, where I sometimes teach small group sessions and advise the church board/finance committee on church finances. I am also an author, having published my first book, The 401k Checkup Prescription for Success, in 2016. Additionally, I am also an inventor and have a patent on one of my inventions. I am also an automotive enthusiast and actively participate in autocross as well as club track days.

My wife, Cindy, and our son, Ryan, both work alongside me, which makes coming to work each day even more meaningful. We live in Southern Oregon, surrounded by the activity and joy that comes with a full household—four dogs, a cat, a goat, a horse, and plenty of wildlife that thrives around the ponds on our property. It's a life that reflects everything I believe about building something lasting and purposeful, both personally and professionally.

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