Scott E. Kelly
Managing Partner, Westport Wealth Partners
They ask about the market. They ask about products. They ask about fees. What they are actually asking, underneath all of it, is some version of this: am I going to be okay?
Scott Kelly has spent his career answering that question. Not with reassurance. With solutions. Specifically, with the kind of solutions that can provide income people cannot outlive, protection for assets they cannot afford to lose, and the kind of access and attention that makes them feel like someone is watching out for them.
He has been doing this for 26 years. He still brings a notepad and a pen to the first meeting.
How Scott Got Into Financial Services and What He Actually Does
Scott entered financial services 26 years ago and has never had a reason to leave. He spent years building his practice, and his relationship with clients like the ones who eventually became the founding client base of Westport Wealth Partners, alongside Nick DiFalco. They shared an assistant, Nichole McCarthy, who is now the firm's Senior Registered Wealth Associate. They talked for years about building something larger together, specifically to serve clients who preferred working with a team over working with a single advisor.
"We talked about working together in order to get bigger clients that preferred teams versus individuals." When the time came to make the move to independence, a recruiter introduced them to Matthew Streif, who had the same goals: independence, growth, and the freedom to serve clients the right way.
At Westport Wealth Partners, Nick and Matt lead the business owner work: exit planning, business valuation, the CEPA®-level disciplines. Scott leads employee retirement plans and retirement income planning. That division of focus is not accidental. It reflects 26 years of building a practice around the clients who need what Scott specifically does best.
Scott holds Series 7 and Series 65 registrations and is licensed for variable life and health insurance: the full set of licenses that allows him to work across investment management, annuity products, and insurance planning. Raymond James financial advisors may only conduct business with residents of the states and/or jurisdictions for which they are properly registered.
What Scott's Clients Actually Look Like
Scott's primary clients are between 55 and 75. Mid to high net worth. Either approaching retirement or already navigating it. They have worked hard, saved reasonably well, and are carrying a fear that most of them articulate only obliquely: what if it is not enough?
They are not do-it-yourselfers. Scott is specific about this: people who have already decided what they want and are looking for someone to execute it are not a good fit for this practice. The clients who benefit most from working with Scott are the ones who want a trusted expert to take the time to understand their situation and build a plan around it. "They want to feel that I care about them and their goals," he says. "And that I can help them."
The thing they most often don't realize is that there are solutions specifically designed for their situation: products and strategies that provide income they cannot outlive, that protect retirement assets from sequence-of-returns risk, and that are more accessible and understandable than they've been led to believe. Making those solutions visible, explaining how they work, and helping clients feel confident in decisions they actually understand: that is Scott's work.
Scott's View on Annuities and Why He Will Say It Directly
Scott Kelly is an annuity specialist. He knows the landscape, knows the products, knows the costs, and knows the criticisms. He also knows what he thinks of the most prominent critics.
"Annuity naysayers like Fisher Investments and Suze Orman, they'll tell you annuities are bad. What they don't tell you is that Fisher's fee-based model has a financial incentive to say that."
He is not dismissive of the legitimate criticisms. Some annuity products have been sold inappropriately. Some have surrender schedules that are wrong for the client. Some are more complex than they need to be. These are real problems with how some products have been distributed, not problems with the underlying mechanism.
Scott wants his clients to understand the products they own. He explains the cost structure (participation rates, cap rates, rider charges) in plain language. He models performance in different scenarios. He shows the tradeoffs. His goal is clients who can explain to a family member what they own and why it makes sense for them.
See the full annuity planning page for the mechanism, costs, and when Scott recommends these products, and when he doesn't.
Employee Retirement PlansScott's Business Owner Lane
The business owner work at Westport Wealth Partners has three layers. Nick and Matt handle the business owner's personal financial planning and exit strategy. Scott handles the layer between the owner and the employees: the retirement plan that makes the company a place good people want to stay.
Scott works with businesses of 50 to 500 employees. The specific type of business matters less than the culture: "the culture of the organization must be employee first." Companies that see benefits as an investment in people, rather than a compliance obligation, are the right clients.
For those companies, Scott designs and implements 401(k) plans and profit sharing plans that accomplish two things: give employees a meaningful path to retirement security, and give the business a competitive advantage in attracting the people it wants to keep. He oversees the ongoing administration, monitors investment performance, and works with plan sponsors on employee education.
This work connects directly to Nick and Matt's exit planning work: a well-run employee retirement plan improves the business's value to outside buyers. It demonstrates professional people practices. It reduces key-person risk by giving employees financial reasons to stay. And for business owners considering an ESOP, which Scott can evaluate alongside the other exit options, an existing qualified retirement plan is an important predecessor.
How Scott Actually WorksWhat a Client Relationship Looks Like
"My goal is to make them feel like the contact is always there."
After 26 years, the feedback he hears from his happiest clients is consistent:
"he helped me get to retirement safely, and I always knew I could reach him."
Scott's Community19 Years With the Umbrella Club
Scott Kelly has been involved with the Umbrella Club for 19 years. The organization raises money for sick and disabled children whose families face financial hardship in Fairfield County. Scott served as president for nine of those years and has been on the board for 17.
"We raise money for sick and disabled children whose families have financial hardships in Fairfield County."
The consistency of that commitment, nearly two decades in an organization serving some of the most vulnerable families in the region, reflects the same qualities his clients describe: accessible, reliable, and in it for the long term.
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Scott also serves on the board of Level the Playing Field, a charity that provides scholarships and assistance to children with special needs in the area. He has been on that board for three years.
Scott has been married to his wife Julie for 21 years. They have two children: Caitlin, 18, who just finished her freshman year at Loyola University, and Colin, 16, who will be a junior in high school this fall.
Frequently Asked Questions About Working With Scott Kelly
What does Scott Kelly specialize in?
Scott Kelly is a Managing Partner at Westport Wealth Partners in Westport, CT, with 26 years of experience in financial services. His primary specializations are retirement income planning, helping clients aged 55 to 75 ensure their assets last through retirement, and annuity products, including fixed, fixed indexed, structured, and variable annuities. He also leads the firm's employee benefits practice, designing and implementing 401(k) and profit sharing plans for Connecticut businesses with 50 to 500 employees. He holds Series 7 and Series 65 registrations and is licensed for variable life and health insurance. Investment advisory services offered through Raymond James Financial Services Advisors, Inc.
What types of clients does Scott work with?
Scott's primary clients are between 55 and 75 with mid to high net worth, either approaching retirement or already navigating it. They have accumulated meaningful assets and are looking for a trusted advisor who will take the time to understand their situation thoroughly before recommending anything. Scott is direct about who is not a good fit: self-directed investors who have already made their decisions and are looking for execution do not benefit from the advisory relationship this practice provides. The clients who benefit most are those who want expert guidance, clear explanations, and an advisor who is genuinely accessible over time.
How does Scott's planning process work?
First meeting: notepad and pen. Scott asks questions, many questions, until he has a complete understanding of the client's financial picture and goals. He summarizes what he heard before presenting any solutions. After engagement, clients have three to four scheduled reviews per year, with additional contact as needed. Scott reaches out on birthdays, sends holiday cards, and checks in informally throughout the year. His stated goal is that clients know they can reach him.
What is Scott's view on annuities?
Scott is a genuine annuity specialist and advocate, not because he dismisses the criticisms, but because he has spent 26 years seeing what guaranteed lifetime income does for clients who need it. He explains the cost structure transparently (participation rates, caps, rider charges) and models product performance in the specific scenarios relevant to each client's plan. He does not recommend annuities to clients for whom they are not the right tool. He does challenge the critics, particularly those with financial incentives to discourage annuity ownership, when their arguments are structurally motivated rather than analytically sound. All annuity guarantees are subject to the claims-paying ability of the issuing insurance company.
How does Scott collaborate with Nick DiFalco and Matt Streif?
At Westport Wealth Partners, the three partners have distinct areas of focus that complement each other. Nick DiFalco leads financial planning and portfolio management, with a focus on business owners and executives with complex compensation. Matt Streif leads business exit planning, business valuation, and the CEPA®-specific disciplines. Scott leads retirement income planning, annuities, and employee retirement plans. For business owner clients, Scott designs and manages the employee retirement plan layer while Nick and Matt address the owner's personal financial planning and exit strategy, covering the full picture of the business and the people inside it.
Annuities are long-term investments designed for retirement purposes. All guarantees are based on the claims-paying ability of the issuing insurance company. Products are not suitable for all investors.