Travis Sylvester, CFP®
Partner & Wealth Advisor · Shoreline Financial Partners
"When my family lost someone we loved, the financial complexity that followed was overwhelming. Nobody had prepared us for it — and that experience changed everything about how I approach this work."
When a business owner in Schaumburg or Deerfield asks me how to protect what they've built, I'm not just thinking about their balance sheet. I'm thinking about what happens to their family if something goes wrong — because I've seen what that looks like up close, and I've made it my life's work to make sure my clients never have to face it unprepared.
Specialties
What I Focus On
My planning work centers on business owners, executives, and high earners who need more than investment management — they need a true financial partner. Specifically, I spend a lot of my time on:
Business Owner Financial Planning
Helping entrepreneurs align their business and personal finances — from cash flow management and entity structure benefits to key-person insurance, succession planning, exit readiness, and building a personal financial plan that works independently of the business.
Executive Compensation Planning
Navigating stock options, RSUs, deferred compensation, and non-qualified plans for executives who need a strategy — not just an investment account — to manage concentrated positions and complex income.
Tax Planning & Strategy
Building proactive, forward-looking tax strategies that go well beyond the annual return — including Roth conversion planning, asset location across account types, tax-efficient withdrawals, and tax-minimizing investment approaches. We're happy to work alongside your existing CPA, or connect you with one of our trusted CPA partners if you need one.
Estate Planning Coordination
Educating clients on Illinois estate tax exposure, trust design and structure, and the importance of powers of attorney for both healthcare and financial decisions. We help clients understand what they have, what they need, and why it matters — then assist with coordinating and organizing documents through our planning tools or connecting them with a trusted estate planning attorney when legal drafting is required.
Investment Planning & Direct Indexing
Building portfolios across the full investment landscape — mutual funds, ETFs, and individual stocks through direct indexing — with a deliberate focus on after-tax outcomes. Strategies include tax-loss harvesting, tax-efficient investing, and REIT exposure for income-oriented clients. For qualified clients, we also provide access to alternative investments including private credit, private equity, structured notes, market-linked CDs, options strategies, and hedge funds. (See Alternative Investments below for more detail.)
Retirement Planning
Comprehensive retirement planning that brings everything together — income strategy, tax efficiency, investment allocation, insurance, and estate structure — modeled through advanced tools like eMoney with stress testing across variable market scenarios. Specific focus areas include Social Security optimization, Medicare Part B premium planning (IRMAA), RMD reduction strategies, Roth conversion simulations, account optimization across Roth, IRA, and non-retirement assets, long-term care planning, and building a spending plan clients can trust through every stage of retirement.
Insurance Planning
Insurance is both a protection tool and a planning tool. We evaluate life insurance needs across term, whole, and indexed universal life strategies, annuities for guaranteed income, long-term care solutions, and asset protection strategies. For clients approaching or in retirement, we also address Medicare planning and the coordination of private insurance — making sure every coverage decision fits within the broader financial plan rather than sitting outside of it.
Alternative Investments
For qualified clients seeking diversification beyond traditional public markets, we provide access to a range of alternative investment strategies — including private credit, private equity, options strategies, REITs, market-linked CDs, structured notes, and hedge funds. Each alternative is evaluated for its role in the broader portfolio: liquidity profile, risk-return characteristics, tax treatment, and fit with the client's overall plan. These are not products we push — they're tools we use when the situation calls for them.
Experience
My Background
I grew up in Schaumburg, Illinois — and this community has shaped everything about who I am and how I work. My path into financial planning wasn't a straight line. It was forged through loss. Within two years, I lost both my father and my brother. The financial complexity that followed was overwhelming, and navigating it without the right guidance made a difficult time even harder. That experience didn't just influence my career — it defined it. I became a financial planner so that the families I work with would never have to face those moments unprepared.
Today, I'm married to my wife Paolina, and we have a one-year-old son — named after my brother. He's a daily reminder of why this work matters and who it's really for.
Before founding Shoreline, I spent two years as an analyst in the futures and options industry, working directly alongside hedge fund managers. That experience gave me a level of market depth and institutional perspective that most advisors simply don't have. From there I earned my CERTIFIED FINANCIAL PLANNER™ designation and built a practice grounded in comprehensive planning, not just portfolio management.
My current licenses and credentials include: CFP®, Series 7, Series 66, and Health & Life Insurance. I also hold a Series 3 (currently inactive) from my time in the futures industry — a background that continues to inform how I think about risk, derivatives, and alternative strategies for my clients.
Our Story
Why I Founded Shoreline
I spent years watching what financial planning looked like inside large institutions — and I knew there was a better version of this work. The big firms are built around sales. Metrics, quotas, product pushes, and advisors stretched too thin to give any single client the attention they actually deserve. I wanted out of that model entirely.
I founded Shoreline Financial Partners because I wanted to own the client experience from start to finish. My clients told me, time and again, what they were looking for: someone who genuinely knows their situation, who has time for them, who isn't rushing to the next appointment or the next sale. Shoreline was built to be exactly that.
Here, I control my time and my client load — which means every client gets a level of depth and attention that simply isn't possible at a wirehouse or national firm.
Community & Personal
Rooted in the Chicago Suburbs
I was born and raised in Schaumburg and have spent my entire life in the northwest and north suburbs. Shoreline operates out of both Schaumburg and Deerfield — which reflects how I think about this work: close to home, close to my clients, and embedded in the communities I serve.
I'm actively engaged in the professional community across both markets — building relationships with CPAs, estate attorneys, and fellow advisors who share a commitment to putting clients first. If you're in the area and want a conversation, I'd genuinely welcome it.
Let's Connect
If you're a business owner, executive, or high earner in the Chicago suburbs and want a real conversation about your financial plan, I'd love to connect.
Past performance is not an indication or guarantee of future results. Investing in mutual funds is subject to risk and loss of principal. There is no assurance or certainty that any investment strategy will be successful in meeting its objectives.
Investors should consider the investment objectives, risks and charges and expenses of the funds carefully before investing. The prospectus contains this and other information about the funds. Contact Shoreline Financial Partners at 847-350-6177 to obtain a prospectus, which should be read carefully before investing or sending money.
REITs are subject to various risks such as illiquidity and property devaluations based on adverse economic and real estate market conditions and may not be suitable for all investors. A prospectus that discloses all risks, fees and expenses may be obtained from 847-350-6177. Read the prospectus carefully before investing. This is not a solicitation or offering which can only be made in conjunction with a copy of the prospectus.