Jonathan Simeon Rosen

Originally from Massachusetts, I now reside in New York City with my wife, Carolina. My interest in personal finance began shortly after graduating college, during my time working for the Boston Red Sox. While the role provided a memorable experience, I quickly realized how challenging it was to navigate employee benefits, manage a budget, and begin saving—especially in a high-cost city. That experience revealed a significant knowledge gap, which I set out to fill through self-study and a deep dive into personal finance literature. Over time, that curiosity evolved into a clear professional purpose: to help others gain clarity and confidence in their financial lives. Following my time in sports, I spent several years working in various client-facing roles across the financial services industry. I gained experience at a regional bank, a large brokerage firm, and most recently, a national Registered Investment Advisor (RIA). Each role offered valuable insight into different areas of the financial world, and collectively, they reinforced my desire to create something more personal and client-centered. I founded Willcox Wealth Management with the goal of providing clear, unbiased financial advice rooted in trust, education, and long-term relationships. I am a CERTIFIED FINANCIAL PLANNER™ (CFP®) and an Enrolled Agent (EA), which allows me to serve clients not only in a comprehensive planning capacity but also with specialized tax expertise before the IRS.

David Warshaw is a CFP® and ChFC® with 20 years of industry experience. He is the principal advisor at The WealthPlan LLC, an independent firm based in Great Neck, NY. Prior to founding The WealthPlan LLC and WealthPlan Risk Management LLC in 2020, he worked at Blueprint Wealth Alliance LLC and American Portfolios Financial Services, Inc. Warshaw is also a licensed insurance agent, focusing on life insurance, fixed annuities, and related products. The WealthPlan LLC provides discretionary portfolio management and financial planning services to individuals, high-net-worth clients, trusts, estates, and business entities. The firm manages approximately $73.8 million in assets and offers customized portfolio construction based on client goals, time horizons, and risk tolerance, incorporating a range of investment strategies and advising on held-away workplace accounts and digital asset custody.

I’m Gabriel Kaplan, CFP®, CPA, and founder of Wealth Habits, an integrated financial planning and investment management firm. I help busy professionals, tech employees, founders, and business owners make better financial decisions across investments, taxes, equity compensation, retirement, cash flow, and estate planning. My work includes strategies for ISOs, NQSOs, RSUs, retirement plans, tax-efficient investing, business transitions, and major life decisions such as buying a home or preparing for retirement. Before founding Wealth Habits, I worked in asset management, tax, and consulting. I hold an MBA from NYU Stern, a Master’s in Business Taxation from USC, and a BSE from the University of Pennsylvania. As a fee-only advisor, I believe financial advice should be tailored, practical, and always aligned with the client’s best interests.

DrawingBoard Wealth Advisors is a registered investment adviser that plans to provide portfolio management and financial planning primarily for institutional investors, family offices, accredited investors, and high-net-worth individuals. The firm’s investment approach integrates fundamental analysis, modern portfolio theory, and technical analysis, with an emphasis on long-term investing and allocations to alternative and private-market strategies.

Zachary Sirota is a financial advisor at IRON Financial LLC with five years of industry experience. He previously worked at CAMPAIGN Capital LLC and B. Riley Securities, Inc., and has credentials including Series 63 and Series 65 licenses. IRON Financial LLC provides discretionary portfolio management and financial planning services to individuals, trusts, charities, corporations, and pooled investment vehicles. The firm manages approximately $472 million in assets, employing a combination of fundamental, technical, and quantitative analysis across various equity, fixed-income, and multi-asset strategies.

Daniel Drahos is a financial advisor with Stirlingshire Investments, holding Series 63 and Series 65 licenses and 15 years of industry experience. His prior roles include positions at Monmouth Capital Management, Worden Capital Management LLC, and Aegis Capital Corp. Stirlingshire RIA LLC provides discretionary portfolio management to individuals, trusts, and other entities, serving both non-high-net-worth and high-net-worth clients. The firm employs a range of investment approaches, including quantitative, fundamental, technical, and modern portfolio theory, and offers access to various investment types such as mutual funds, ETFs, fixed income, REITs, private placements, and alternative vehicles.