Rob Simon

Rob Simon joined Waverly Advisors in July 2024 with more than 15 years of experience in wealth management. Prior to joining Waverly, Rob served as President of River Capital Advisors before the firm’s acquisition by Waverly Advisors, LLC.

As a leader of the Jacksonville team, Rob works closely with individuals and families to help them navigate complex financial decisions and align their wealth with their long-term personal, family, and philanthropic goals. His experience advising clients through investment management, estate planning, tax-aware strategies, and charitable giving allows him to provide comprehensive guidance tailored to each client’s unique circumstances.

Rob is a CERTIFIED FINANCIAL PLANNER® practitioner (CFP®), an Accredited Estate Planner® (AEP®), and a Chartered Advisor in Philanthropy® (CAP®), designations that reflect his commitment to integrated, planning-focused advice.

Outside of work, Rob enjoys spending time with his wife, hiking, traveling, and collecting vinyl records.

Specialization

Areas of Expertise

Philanthropic Planning & Donor-Advised Funds

Holistic Wealth Planning

Private Markets & Alternative Investments

Tax, Estate & Legacy Planning

Tax Optimization & Mitigation

Multi-Generational Wealth Planning

Investment Strategy & Portfolio Management

Serving with Purpose

A Culture of Connection

Waverly takes its name from a meadow of quaking aspen trees, an ecosystem where individual trees are connected by a shared root system. Since 1999, that idea has inspired our firm: strong relationships, shared values, and the belief that we are better together.

Comprehensive Wealth Management, Connected by Design

Like an aspen grove, every part of a client’s financial life is interconnected. As an independent Registered Investment Advisor (RIA), we bring together investment management, financial planning, tax strategy, trust and estate planning, and family office services to create coordinated solutions that simplify complexity and support long-term success.

A Culture Rooted in Service

Our culture of stewardship is guided by Integrity, Family, Grace, Team, Drive, Empathy, and Community. These values shape every client relationship, every decision, and every interaction. They are the foundation that keeps our people connected and ensures a consistent, high-touch experience across the firm.

The Difference Is Our People

While many firms offer financial advice, our greatest differentiator is our people. Waverly’s advisors, planners, investment professionals, tax specialists, and support teams work together to deliver thoughtful guidance and personalized solutions. It is this collaborative approach, and our commitment to serving clients with excellence and care, that transforms financial advice into lasting relationships.

Education

Master’s of Science in Financial Planning, Legacy Planning, The American College of Financial Services
B.S.B.A., Finance, University of North Carolina at Charlotte

Professional Affiliation

NAPFA
FPA
Garrett Planning Network

Ask Me About

Tax Management Strategies
Legacy Planning
Private Investments

Published by Rob Simon

Blogs

Financial Planning

The Planning Conversation I Thought Could Wait

As a financial advisor, many people probably assume that I have every aspect of my personal financial planning perfectly organized at all...