Joseph Rosario, CFP®
Partner & Wealth Advisor · Shoreline Financial Partners
"My passion for finance started when I was a kid. My grandmother used to make me sit with her and watch the stock tickers on CNBC, and I'd report back how her investments did that day. That's where my interest in the markets first began."
When a client in Chicago or Puerto Rico asks if they're going to be okay in retirement, I'm not thinking in theory — I'm thinking about real life. Cost of living, taxes, family, college, business ownership, caring for parents. These are the same realities I deal with myself, which is why the advice I give is practical, personal, and built for the real world.
Specialties
What I Focus On
My planning work centers on clients who have reached a stage in life where they need more help. Specifically, I spend a lot of my time on:
Roth Conversion Strategy
Pinpointing the optimal window — the right years, amounts, and brackets — to convert pre-tax dollars before RMDs drive up your tax bill for good.
Medicare IRMAA Planning
Proactively managing your income to avoid the Medicare surcharges that blindside so many retirees — especially those who didn't know about the two-year lookback rule until it was too late.
Retirement Income Planning
Building a coordinated drawdown strategy that connects your Social Security timing, investment withdrawals, and day-to-day spending into one cohesive plan you can actually live off.
Illinois Estate Tax Coordination
Working with families whose estates exceed Illinois' $4 million threshold to structure Credit Shelter Trusts and gifting strategies that reduce what gets left behind for the state.
Tax-Efficient Investing
Helping clients with meaningful taxable account balances put more of their returns to work — through direct indexing, tax-loss harvesting, and asset location strategies.
Puerto Rico Act 60 (Puerto Rico Incentives Code)
Act 60 (passed in 2019) is a tax incentive program designed to attract investors, business owners, and high-income individuals to move to Puerto Rico. It combines earlier laws (Act 20 & Act 22) into one system.
Experience
My Background
I've been in the financial services industry for over 16 years. Before co-founding Shoreline Financial Partners, I built my career at several firms, developing my practice from the ground up before spending nearly a decade at Fidelity Investments. During my time there, I worked with high-net-worth families throughout the Chicago area and oversaw more than $1 billion in client assets, helping clients navigate complex financial decisions in a fast-paced environment.
Over the course of my career, I've worked with clients across nearly every financial situation imaginable — from young professionals just getting started to high-net-worth families planning for retirement, business transitions, and generational wealth. These experiences shaped my belief that financial planning should be personal, practical, and built around real life, not just numbers.
Our Story
Why I Started Shoreline
I co-founded Shoreline Financial Partners so that I could provide the full-service financial planning that clients are looking for. One of my favorite parts of this job is developing a deep relationship with my clients. Knowing their full situation requires me to be present at every step along the way, and Shoreline gives me the ability to provide the attention that clients deserve.
We built Shoreline around four CFP® partners, each bringing deep expertise and a fiduciary commitment to every client relationship. It's the kind of firm I always wanted to work for.
Community & Personal
Rooted in Chicago & Beyond
I was born and raised in the Chicago area and earned my CERTIFIED FINANCIAL PLANNER™ designation early in my career. I am also actively involved with Camp One Step, serving on the Philanthropy Council, where I support efforts to provide meaningful experiences for children and families facing serious illnesses.
Outside of work, I enjoy traveling to Puerto Rico to spend time with my father and extended family, golfing whenever I can, and relaxing at home grilling and spending time outdoors with my family. I am also the proud father of two amazing boys, William and Liam.
Let's Connect
If you're in the Chicago area or have ties to Puerto Rico and want a real conversation about your financial plan, I'd love to connect.
Converting from a traditional IRA to a Roth IRA is a taxable event. A Roth IRA offers tax free withdrawals on taxable contributions. To qualify for the tax-free and penalty-free withdrawal or earnings, a Roth IRA must be in place for at least five tax years, and the distribution must take place after age 59 ½ or due to death, disability, or a first-time home purchase (up to a $10,000 lifetime maximum). Depending on state law, Roth IRA distributions may be subject to state taxes.