Many people plan around a retirement that lasts 20 or 30 years, but advances in medicine and health are pushing life expectancy well past the old assumptions, and that shift changes the math on nearly every part of a financial plan. In this episode, Dave Alison, President of Wealth Management and Founding Partner at Prosperity Capital Advisors, and co-host Greg Dillon, Head of Financial Services at Prosperity Capital Advisors, walk through what they call longevity risk. It refers to the growing chance that a retirement lasts far longer than expected, and what that means for Social Security timing, guaranteed income, and planning for extended care.
They also share real client examples that show how the right plan can turn a long life from a financial risk into an opportunity.
What We’ll Cover:
Why planning for a longer life expectancy changes the math on retirement income, taxes, and market risk
How Social Security optimization works and why the decision should never be made in isolation
What guaranteed income sources, like annuities and pensions, can do for retirement confidence (often called mitigating longevity risk)
Why a plan for extended care matters for a family’s finances as much as for a person’s health
How to think about accepting risk versus mitigating it when building a retirement income plan
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Holistic wealth and health is the idea at the center of this new podcast from Prosperity Capital Advisors, hosted by Dave Alison and Greg Dillon. Rather than treating financial planning and personal well-being as separate topics, Dave and Greg open the series by explaining why the two are closely linked for clients at very different stages, from pre-retirees and business owners to founders and executives navigating significant equity or liquidity events. They walk through how their own career paths, shaped by the 2008 financial crisis and years of helping clients manage major wealth transitions, led them to build their approach around this connection. The conversation also touches on why tax management remains one of the most overlooked parts of a financial plan, regardless of how much someone has saved or how they built it.
What We’ll Cover:
Why Dave and Greg treat financial planning and personal health as connected, not separate, parts of a plan
How the right mix of pre-tax, post-tax, and tax-advantaged accounts (often called account type diversification) can factor into retirement timing
Why an advisor’s own experience through a financial crisis can shape how closely they watch a client’s downside risk
What advising founders, executives, and business owners through major wealth events can reveal about avoiding a “just in case” retirement
How AI tools can support, but not replace, sound financial guidance
Timestamps: 00:00 — Cold open: why health matters to wealth 00:30 — Welcome to the show and meet the hosts 02:00 — Why Dave and Greg host together 03:00 — Introducing the Five Pillars framework 04:00 — Dave’s path into financial planning 08:00 — Building a holistic wealth management practice 13:00 — Serving clients from pre-retirees to ultra-high-net-worth families 15:00 — Greg’s path from Wall Street to advising 25:00 — Why account type matters as much as investment mix 29:00 — Living confidently instead of “just in case” 31:00 — Using AI tools wisely in financial planning 32:00 — What is coming in future episodes
When tax season ends, tax planning begins. Join host Bryan Bibbo as he sits down with Chad Weigl, CFF, BPC, NSSA, lead advisor at JL Smith Holistic Wealth Management, a Prosperity Capital Advisors company, to walk through what high-income earners and pre-retirees should consider once their return is filed.
With more than a decade of experience in retirement income planning, tax strategy, Social Security, and estate planning, Chad breaks down which line items on your return reveal some of the biggest missed opportunities, and how to translate this year’s outcome into a smarter plan before the window closes.
Key Topics:
Your Tax Return as a Planning Tool: Why filing it away until next April can be a costly mistake, and which specific line items deserve your attention right now.
The Hidden Cost of Capital Gain Distributions: How internal trades by mutual fund and exchange-traded fund (ETF) managers can generate surprise taxable events, and what strategies may help reduce them.
Tax-Efficient Withdrawal Strategies: How structuring distributions across pre-tax, post-tax, and Roth accounts can help keep you in the lowest possible bracket throughout retirement.
Roth Conversions and Market Downturns: Why periods of market volatility can create timely opportunities to convert more shares at a discount and let them recover tax-free.
Planning for High-Income Earners: How to approach deferred compensation elections, restricted stock units (RSUs), and equity compensation, and why many of these decisions often need to be made a full year in advance.
In this deeply personal continuation of our conversation with NFL legend Fred Taylor, host Bryan Bibbo explores mental health, parenting wisdom, and financial education that extends far beyond the gridiron. Discover how a Hall of Fame-bound running back transformed from party mode to purposeful living while building a legacy that transcends football.
Through candid discussions about gaps in education—from financial literacy to parenting skills—Fred shares how he’s breaking generational cycles while teaching his children to find their own purpose.
Key Topics:
Financial Education Crisis: Why financial literacy isn’t taught in schools and how this systematic gap perpetuates cycles of financial struggle, especially among student-athletes and young professionals.
Parenting Without Entitlement: Strategies for raising grounded, respectful children despite wealth and fame, including the importance of exposing kids to different paths rather than choosing their journey for them.
Mental Health & Athlete Identity: Anxiety, depression, and the unique challenges athletes face when their physical capabilities begin to change, plus holistic approaches to mental health management.
The Power of Routine & Commitment: How establishing and maintaining disciplined routines—whether in sports, finances, or life—creates the foundation for long-term success and helps overcome the monotony that can derail progress.
Living Present vs. Past/Future: The transformative power of staying grounded in the present moment rather than being trapped by past regrets or future anxieties.
In this episode, host Jason L Smith is joined by Chris Smith, the founder of Family Brand. They delve into the transformative journey of creating a strong, unified family culture. The discussion touches on how family unity and shared values contribute to overall well-being, drawing inspiration from concepts like ‘Blue Zones’ and the Japanese philosophy of Ikigai.
Key Highlights:
1. Introducing Family Brand: Chris Smithshares the inspiration behind founding Family Brand, rooted in his personal experiences and family challenges.
2. The Impact of Family on Longevity: A discussion on ‘Blue Zones’ and how family dynamics significantly contribute to longevity, inspired by the Netflix documentary “Live to 100: Secrets of the Blue Zones.”
3. Building a Family Brand: The conversation covers the process and benefits of establishing a family brand, including mission, vision, culture, and values, as experienced by host Jason with his family
4. Family History and Identity: The importance of knowing and sharing family heritage and stories to bolster family identity and resilience.
5. The Pillars of Family Values: Chris outlines eight crucial categories for developing robust family values, based on extensive research.
6. Family Brand Culture Quiz: Introduction to the quiz designed to help families understand and enhance their family culture.
7. Engagement Options with Family Brand: Overview of different programs offered by Family Brand, including digital, group, and private coaching options.
Listeners are encouraged to reflect on their family values and explore the resources offered by Family Brand to strengthen family bonds and create a lasting legacy.
Disclaimer: Investment advisory services are provided through Prosperity Capital Advisors LLC (“PCA”) an investment advisor registered with the United States Securities and Exchange Commission (SEC). For a detailed discussion of PCA and its investment advisory fees, see the firm’s Form ADV and Form CRS on file with the SEC at www.adviserinfo.sec.gov. The views expressed herein represent the opinions of PCA and are not intended to predict or depict performance of any particular investment.
