Second 50 Financial, LLC 

My Local List

• Favorite Italian: Mangiamo Ristorante
• Favorite Breakfast Burritos: Baran’s 2239
• Favorite Mexican: El Sombrero
• Favorite Butcher: Manhattan Market

Second 50 Financial’s motto is “Wealth Management for Life’s Next Chapter.” The firm—cofounded in 2021 by Kathleen Adams and David Swift—guides clients through the important financial considerations in their second 50 years. The team offers personalized strategies designed to address clients’ evolving needs and long-term objectives.  

How do your professional partnerships elevate what you offer clients?

At Second 50 Financial, our independence allows us to partner with world-class investment firms—not product quotas. We build portfolios that go far beyond the traditional—incorporating private equity, real estate and alternative investments available to our clients through our strategic partnerships, which not every advisor has access to. For example, our clients benefit from strategic allocations due to opportunities with firms like Blue Owl Capital, Hillpointe and CIRE Equity, as well as participation in high-profile private equity deals including SpaceX, Databricks and Anthropic. These unique partnerships expand the investable universe, offering potential diversification, stronger risk management and access to the innovation driving the modern economy.

What’s the most important step you take to understand the unique needs of clients?

Our complimentary Second 50 Readiness Meeting is the first and most important step. It’s a focused conversation designed to uncover each client’s goals, lifestyle priorities and financial concerns. As part of this process, we create a personalized S50F Wealth Map to visually organize their financial life. This meeting lays the foundation for highly customized, forward-thinking strategies tailored to help clients align their wealth with purpose in their Second 50. It also gives us a chance to get to know each other and mutually determine if we’re a strong fit for a long-term partnership.

Describe a time you customized a solution to meet the specific needs of a client.

One client faced the burden of managing appreciated rental properties but still needed steady income and flexibility. Through our partnership with Blue Owl, we facilitated a 1031 DST solution—allowing them to exchange real estate with tax efficiency, boost income and diversify into institutional-grade assets like data centers and distribution hubs through their unique UpReit structure. This strategy provided passive income, reduced management stress and allowed partial liquidity over time—transforming a rigid, low-basis real estate position into a professionally managed, income-generating, more flexible solution for their Second 50.

How do you assist clients in planning for their legacy and estate? What considerations do you take into account during this process?

At Second 50 Financial, legacy planning begins only after we’ve ensured your wealth will fully support your lifestyle. We distinguish between investing for income and investing for impact—offering strategic guidance on tax-efficient wealth transfer, asset protection and charitable giving. This now also includes helping ensure digital asset protection and access (such as online bank accounts, emails, etc.) as an additional clause in the estate plan. We also explore “living legacy” strategies, allowing clients to enjoy the impact of their generosity during their lifetime. As the world changes, we have to keep adapting in ways we didn’t consider even 10 years ago. 

How do you help clients avoid making rash decisions with their money?

For our clients nearing and in retirement, we always start with a clear distribution strategy—not just a diversified portfolio. Too many investors enter retirement focused on simply growing wealth vs. understanding how to use that wealth to provide income. At this stage, success depends less on beating the market and more on building a tax-smart, sustainable income plan. Map out where your withdrawals will come from, in what order and with what tax impact—before markets force your hand. Sequence of returns, tax-drag poor withdrawal planning and failure to account for living longer are often more dangerous than market volatility itself. 

Disclaimer: All responses provided are for illustrative purposes only. Descriptions are not recommendations, solicitations, or offers for any investment advisory services or securities. No response is intended as personalized investment, tax or legal advice. Investing in private equity investments involves the risk of loss, including the risk of loss of principal, that clients should be prepared to bear. You are advised to consult with your independent investment, legal and/or tax advisers with respect to your individual financial situation and investment needs before considering any investment or financial strategy.

Photographed by Randy Schwartz