Thomas Hamlin: Building a Future Where Retirement Income and Wealth Management Work Together

CEO and Founder, Somerset Wealth Strategies

What does financial security mean when a lifetime of savings must become a dependable source of income? For millions of Americans approaching retirement, the answer involves more than choosing investments or protecting accumulated wealth. It requires a carefully coordinated strategy that balances growth, risk management, reliable income, and the personal circumstances that shape every financial decision. Thomas Hamlin, CEO and Founder of Somerset Wealth Strategies, has spent more than three decades building his business around this challenge, believing that retirement planning should bring investment management and income protection into the same conversation.

Through the Somerset family of companies, Hamlin has developed an independent financial services model that combines annuities with fee-based, fiduciary wealth management. His approach reflects a conviction that financial products deliver greater value when they work together within a broader plan designed around the client. Today, with a long-established team, an expanding advisory business, and an ambitious commitment to artificial intelligence, he continues to prepare his organization for the changing demands of retirement planning.

For Hamlin, the objective is straightforward: help people protect what they have earned, make informed financial decisions, and approach the years ahead with greater confidence.

The Experience That Shaped an Independent Vision

Hamlin began his financial services career in 1990 at Independent Advantage Financial in Los Angeles, marketing annuities through newsletters before the internet transformed the industry. Within little more than a year, he became the company’s leading salesperson among approximately 35 agents. The founders’ unwillingness to offer him equity prompted him to seek greater independence.

Guided by mentor Jeff Oster, Hamlin joined Prudential Securities in late 1994. Disputes over transferring client relationships created a difficult first year, eventually ending in a settlement that allowed them to continue serving their clients. The experience strengthened Hamlin’s belief that clients must retain the freedom to choose their financial advisers.

In May 1997, he affiliated with Raymond James Financial Services and established his own branch, reuniting with former colleagues Tom Harding and Mark Huntley. This venture became Somerset Wealth Strategies, named after the English county associated with his father.

Building an independent firm brought financial pressures, regulatory challenges, and the responsibilities of entrepreneurship. Hamlin learned that success depended less on exceptional intelligence than on persistence, determination, and doing what was right for clients. Despite the demands of business ownership, he remained committed to creating an organization where professional independence and client interests could thrive together.

Creating a Dual-Platform Financial Services Model

Somerset’s evolution reflects Hamlin’s ability to adapt to changing financial needs while remaining committed to the principles that shaped his business. The company began as an independent insurance agency, with annuities at its core. Its affiliation with Raymond James later allowed him to conduct securities-related activities through an established platform while maintaining Somerset’s fixed insurance business separately.

A major transition occurred in 2012 and 2013, when Hamlin separated from Raymond James, acquired Bay Colony Securities—a Boston-based broker-dealer with approximately 50 years of history—and established Somerset Wealth Management as a fee-based, fiduciary wealth management firm.

These developments created a broader group comprising Somerset Wealth Strategies, Somerset Wealth Management, and Somerset Securities. Each business serves a distinct purpose within a coordinated approach to financial planning.

Hamlin recognizes that retirement planning requires more than a single financial product. Investment portfolios can support long-term growth, while market volatility may complicate withdrawals during retirement. Annuities can provide contractual guarantees and income options, depending on their terms and suitability. Rather than viewing these approaches as competing choices, he sees them as complementary tools that can support different financial objectives.

“People do not retire into a product. They retire into a lifestyle. The job is to put the growth and the income in the same plan so one does not undo the other.”

— Thomas Hamlin

Somerset’s offerings include fixed annuities, multi-year guaranteed annuities, fixed indexed annuities, registered index-linked annuities, immediate annuities, and fee-based wealth management. Supporting services include life insurance, long-term care, Medicare guidance, and trust and estate planning.

Over the years, Hamlin has explored mutual funds, life insurance, alternative investments, and private placements, gaining valuable lessons about their respective limitations. Today, he favors a more focused structure built around annuities and fiduciary wealth management.

For him, greater complexity does not necessarily mean better results. A coordinated strategy, shaped around a client’s circumstances, priorities, and risk tolerance, offers a more thoughtful foundation for financial decision-making.

Growth Built on Persistence and Perspective

Somerset’s growth accelerated around 2000, when Hamlin relocated to Lake Oswego, Oregon, and began expanding his team. Over the following years, the organization experienced different cycles of growth and adjustment, maintaining an average of approximately 10 to 20 team members in the Portland area while building marketing capabilities across several states.

The company also developed relationships with external product and technology partners, broadening the resources available to its advisors and clients.

Hamlin’s experience has taught him that expansion should be measured by its contribution to the business rather than by its size alone. Larger organizations can create additional management responsibilities, communication challenges, and operational costs. They can also pull leaders away from the work in which they are most effective.

This perspective is particularly relevant to Hamlin, who continues to generate more than two-thirds of the firm’s revenue through his own production. His involvement in client relationships keeps him connected to the practical realities of the business and reinforces his belief that organizational decisions must ultimately improve the quality of service.

The Somerset businesses have demonstrated substantial activity across their principal areas. Over his career, Hamlin estimates that he has helped place approximately $1.5 billion in annuity premiums, excluding other asset classes. Annual new and repeat annuity business has historically averaged around $100 million in premium, while Somerset’s wealth management operation is targeting approximately $50 million in new assets under management during 2026.

The firm has also been developing its recurring advisory revenue, which has reached the seven-figure range, with an ambition to move toward eight figures over the next five years.

These figures reflect a business adapting its revenue structure while retaining the insurance expertise that established its foundation. Hamlin recognizes that recurring advisory relationships are important to the long-term development of fee-based wealth management practices. Strengthening that side of the business is therefore a strategic priority rather than a departure from Somerset’s established identity.

“I don’t profess to be the smartest person in most rooms. What I have is the willingness to stay with the problem until it is solved the right way for the client. That is the part that compounds.”

— Thomas Hamlin

His interpretation of success remains grounded in persistence, a willingness to learn, and the belief that people continue to need thoughtful financial guidance. The business has survived difficult markets, changing regulations, and periods of uncertainty. For Hamlin, those experiences have reinforced the importance of building an organization capable of responding to circumstances without losing sight of its purpose.

Leading Through Trust, Ownership, and Experience

Thomas Hamlin’s leadership philosophy centers on trust, accountability, and developing capable professionals. He seeks self-motivated individuals who take ownership of their responsibilities, make sound decisions, and consistently prioritize client expectations. Managing business ownership, executive responsibilities, and personal production requires him to delegate effectively and rely on experienced colleagues who can resolve challenges independently.

Somerset’s long-serving team reflects this approach. Senior colleague Andrew Murdoch has worked alongside Hamlin for approximately 22 years, while advisor Derek Stamos has contributed around 14 years. Other experienced team members include Meg Odermatt, office manager Kristen Odermatt, and compliance leader Meagan Sinniger. Their collective experience provides valuable institutional knowledge and continuity.

Hamlin invests in employee development through training, mentorship, goal setting, and opportunities for professional advancement. He recognizes that retaining talented people strengthens client relationships, reduces recruitment challenges, and preserves the expertise built over years of collaboration.

The firm’s future also includes the next generation, with his son, Brian Hamlin, joining the advisory team in 2023. His involvement represents another step toward long-term continuity.

For Hamlin, effective succession extends beyond transferring responsibilities. It means developing professionals who understand the organization’s values, uphold its service standards, and can navigate future challenges confidently. By combining individual accountability with collective experience, he aims to ensure Somerset remains resilient, dependable, and focused on helping clients achieve their financial goals.

Learning From Risk and Building for Resilience

Entrepreneurship has taught Thomas Hamlin that success requires calculated risks, persistence, and the ability to recognize when a strategy needs to change. He encourages experimentation but believes unsuccessful initiatives should be discontinued before they consume excessive resources. Equally, promising ideas deserve sufficient time to demonstrate their potential.

As the owner of Somerset’s businesses, Hamlin considers himself the last person to get paid, reinforcing his commitment to responsible financial management. His experiences navigating the market downturns of 2000–2002, the 2008 financial crisis, and the COVID-19 pandemic have further shaped his approach to risk.

The pandemic exposed weaknesses in an area of the firm’s investment strategy, prompting Hamlin to reassess its priorities and strengthen its operational foundations. He describes Somerset as a structure designed to withstand severe conditions—emphasizing preparedness, resilience, and adaptability.

These principles also influence the firm’s financial solutions. Hamlin sees registered index-linked annuities and multi-year guaranteed annuities as potential tools for balancing growth opportunities with protection and predictable returns, depending on individual circumstances and contract terms.

For him, effective risk management is not about eliminating uncertainty. It involves understanding potential outcomes, making informed decisions, and building safeguards that protect clients’ long-term financial interests.

Artificial Intelligence as a Competitive Advantage

Technology has become another central pillar of Somerset’s future. Hamlin believes financial services will undergo substantial change over the coming decade, driven by advances in artificial intelligence, automation, and software designed to improve how professionals analyze information and manage their work.

Rather than treating technology as a supplementary convenience, Somerset is working to integrate it into its operating model. Through external technology partnerships, the organization aims to provide its team with tools that support analysis, communication, onboarding, and internal processes.

Hamlin’s ambition is to enable each team member to perform with the effectiveness of a much larger workforce. His comparison is to an elite military unit: a lean team in which every individual is highly capable, well equipped, and focused on the mission.

The strategy is particularly relevant to an independent firm competing in an industry where larger organizations can deploy substantial resources. Appropriate technology can help smaller teams improve efficiency, reduce repetitive administrative work, and devote more attention to client relationships.

Somerset has also been working with Geoff Woods, author of The AI-Driven Leader, as part of its efforts to incorporate AI into the business. Hamlin sees considerable potential in using these capabilities to strengthen internal processes and help advisors deliver more consistent service.

“The point of the technology is not to sound advanced. It is to take the busywork off the team so we can spend the time where it matters—understanding the person and making a recommendation they can explain back to me.”

— Thomas Hamlin

Nevertheless, technology is not the ultimate objective. Financial decisions involve personal priorities, competing needs, and consequences that extend beyond calculations. AI can assist with information processing and operational efficiency, but professional judgment, appropriate oversight, and meaningful communication remain essential.

Hamlin’s vision is to remove avoidable administrative burdens so advisors can spend more time understanding clients and developing suitable strategies. In that sense, technological innovation supports the firm’s existing purpose rather than replacing it.

Education and a Commitment to Client Understanding

Hamlin’s commitment to financial education extends beyond Somerset’s advisory services. In 2000, he founded AnnuityFYI, an independent educational platform designed to help Americans understand annuities and make informed financial decisions. Celebrating its 25th anniversary in 2025, the platform continues to support Somerset’s broader commitment to consumer awareness.

Hamlin believes people should understand the products they consider before making significant financial commitments. Since annuities differ in their guarantees, charges, surrender periods, and potential benefits, clear information helps consumers evaluate their options more effectively.

This educational mission also reaches audiences through Conquering Retirement with AnnuityFYI, a podcast overseen by Greg Shaughnessy and produced with Abby Walker. Shaughnessy has contributed to Somerset’s marketing operations for many years, working alongside his sister, Erin Shaughnessy MacDonald.

For Hamlin, education encourages meaningful questions, informed comparisons, and productive conversations between clients and advisors. It also reinforces Somerset’s emphasis on diversification, ensuring financial recommendations consider individual objectives, risk tolerance, and long-term needs rather than relying on a single investment strategy.

Purpose Beyond Business

Hamlin’s understanding of leadership also reflects his Christian faith, which is central to his personal values. He and his partner, MacKenzie Stewart, are actively involved in their church and are raising five children within that commitment.

Their values extend into the firm’s charitable activities through Somerset Charitable, which distributes a significant share of company profits to charitable causes. For Hamlin, giving is an expression of stewardship and responsibility, connecting the success of the business with a broader obligation to contribute to others.

This perspective informs his belief that financial services should be about more than accumulating assets or achieving commercial milestones. Money matters because it affects people’s security, choices, families, and ability to navigate uncertainty.

The people approaching retirement have often spent decades working, saving, raising families, and making sacrifices. Their financial decisions deserve careful attention because the consequences can influence the quality of their lives for years to come.

Hamlin’s emphasis on peace of mind grows from that understanding. He wants clients to feel that their financial arrangements have been considered thoughtfully, that the risks are understood, and that the people responsible for their plans remain accessible when questions arise.

The firm continues to maintain direct communication through phone calls and virtual meetings, serving clients across the United States and internationally. For Hamlin, geographical reach should never become a substitute for personal attention. Technology may make relationships easier to maintain across distances, but trust still depends on listening, responsiveness, and accountability.

Looking Toward the Next Chapter

As Somerset moves forward, Thomas Hamlin remains focused on strengthening its annuity and fiduciary wealth management platforms, expanding recurring advisory revenue, embracing artificial intelligence, and preparing future leaders to sustain the firm’s success. The opening of a Florida office in 2026 marks another step in expanding its presence while preserving the close-knit team culture that has defined the organization.

The financial services industry will continue to evolve through changing regulations, market uncertainty, and technological advancements. Hamlin’s priority is to ensure Somerset remains adaptable, resilient, and committed to delivering meaningful value to its clients. His experience has taught him that independence brings not only freedom but also accountability, requiring leaders to learn from setbacks and make decisions with long-term consequences in mind.

From marketing annuities before the internet to integrating AI into modern financial operations, Hamlin has consistently sought better ways to serve clients. His vision remains rooted in coordinating income, investments, and protection within a comprehensive financial strategy.

Ultimately, Hamlin measures success by more than business growth. Through Somerset’s experienced team, evolving technology, and client-focused approach, he aims to help families make informed decisions, safeguard their financial futures, and approach retirement with greater confidence and peace of mind.