Today, Jesse is joined by Professor John Dinsmore—behavioral finance researcher, marketing scholar, and author of The Marketing of Debt: How They Get You—for a conversation about how persuasion, psychology, and modern advertising quietly shape our financial lives. Together, they explore how marketers exploit human biases like loss aversion, anchoring, and over-optimism to sell products, loans, and debt, and why AI-driven "adaptive ads" are making it harder than ever to recognize when we're being influenced. John shares real-world examples—from car dealerships to "buy now, pay later" offers and sports betting apps—revealing how even savvy consumers fall prey to tactics designed to exploit fear, emotion, and cognitive shortcuts. The discussion also dives into the growing vulnerability of retirees targeted by complex financial products, and why awareness, self-monitoring, and slowing down decisions are key defenses. Throughout, Jesse and John remind listeners that acknowledging our weaknesses is a strength—and that understanding how marketing works is one of the best ways to protect both our wallets and our wellbeing.

Key Takeaways:
• Marketing works on everyone—even when we think we're immune. Most people admit that advertising influences others, but few realize how deeply it shapes their own decisions.
• People tend to believe they'll have more time, money, or stability in the future, making it easy to justify debt today.
• Loss aversion drives many financial mistakes. We fear losses more than we value gains, which leads us to buy unnecessary warranties, insurance, or "safety" products.
• AI-powered marketing will get subtler. As systems learn to mimic human tone and emotion, it will become harder to tell when you're being influenced.
• Social media blurs the line between content and advertising. Influencer partnerships and native ads make it harder to recognize when you're being sold to.
• Being "weak" isn't failure—it's human. Admitting our psychological blind spots allows us to build systems and habits that protect us.

Key Timestamps:
(01:49) – Understanding Personal Weaknesses
(04:25) – The Impact of Marketing and Advertising
(08:22) – Interview with Professor John Dinsmore
(13:19) – The Marketing of Debt
(25:56) – Practical Tips to Combat Marketing Influence

Key Topics Discussed:
The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques

Mentions:
Website: https://www.johndinsmore.com/
LinkedIn: https://www.linkedin.com/in/johnbdinsmore/
Mentions:
https://bestinterest.blog/i-am-weak/
The Marketing of Debt: How They Get You by John B. Dinsmore

More of The Best Interest:
Check out the Best Interest Blog at https://bestinterest.blog/
Contact me at jesse@bestinterest.blog
Consider working with me at https://bestinterest.blog/work/

The Best Interest Podcast is a personal podcast meant for education and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Jesse goes solo for a deep dive into the vital yet often overlooked world of special needs financial planning. He opens with a personal story about his daughter's illness—an experience that deepened his empathy for parents whose caregiving journeys never pause—and uses it to frame the emotional and financial realities families face when raising a child with disabilities. From there, he explores how special needs planning extends beyond traditional wealth management, requiring families to think in decades, not years, while balancing their own retirement goals with lifelong care needs. Jesse breaks down key tools such as special needs trusts, ABLE accounts, and government programs like SSI and Medicaid, explaining how they work together to preserve benefits and provide sustainable support. He also examines the potential role of permanent life insurance as a funding mechanism for long-term care, the legal importance of guardianship and trusteeship, and the wisdom of separating caregiving and financial responsibilities to prevent burnout. Throughout, Jesse underscores the need for community resources, professional guidance, and self-care—reminding listeners that special needs planning isn't just about money, but about love, security, and building a future where every member of the family can thrive.

Key Takeaways:
• Raising a child with special needs requires planning for both the parents' and the child's lifetimes—often extending decades beyond traditional financial horizons.
• Special needs families face higher ongoing costs, from medical treatments and therapies to adaptive equipment and in-home care.
• Core financial fundamentals—emergency savings, retirement planning, tax strategy, and estate planning—remain essential but must be adapted for special needs circumstances.
• Nonprofits, community organizations, and local programs can offer both financial aid and emotional support for families.
• Professional guidance from fiduciary planners and special needs attorneys can help families integrate benefits, trusts, and insurance effectively.
• Above all, special needs planning is about more than money—it's about love, security, and ensuring a dignified, supported life for every family member.

Key Timestamps:
(00:00) – Deep Dive: Special Needs Planning
(08:12) – Unique Financial Challenges of Special Needs Families
(15:56) – Special Needs Trusts: Protecting Your Child's Future
(19:36) – Introduction to ABLE Accounts
(23:59) – Life Insurance for Special Needs Families
(28:37) – Guardianship and Legal Planning
(33:45) – Community and Professional Resources

Key Topics Discussed:
The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques

More of The Best Interest:
Check out the Best Interest Blog at https://bestinterest.blog/
Contact me at jesse@bestinterest.blog
Consider working with me at https://bestinterest.blog/work/

The Best Interest Podcast is a personal podcast meant for education and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Jesse fields six wide-ranging listener questions that dig into the heart of financial planning and investing. He opens with a challenge to the idea that age alone dictates portfolio strategy, emphasizing instead that time horizons, goals, and diversification determine the right balance between growth and preservation. From there, Jesse advises a listener who recently inherited $1 million on how to integrate the windfall into an early retirement plan through detailed cash flow projections, withdrawal strategies, and careful consideration of pensions and Social Security. Next, he unpacks the difference between risk tolerance and risk capacity—framing them as willingness versus ability to take risk—and illustrates how these concepts vary depending on age, assets, and future income. A question about bonds leads to a deep dive on duration, interest rate sensitivity, and why bond funds and individual bonds behave more alike than many investors assume, with practical guidance on structuring fixed income for retirement needs. Shifting to income growth, Jesse shares seven strategies for boosting earnings over time, from negotiating raises and pursuing certifications to building businesses, climbing the career ladder, and gaining equity participation. Finally, he closes with a clear primer on Bitcoin, explaining blockchain, mining, and the role of trust in money, while stressing that investors don't need cryptocurrency in their portfolios—but should at least understand what it is and why it matters.

Key Takeaways:
• Investment strategy should be based on goals and timelines, not just age.
• A $1 million inheritance should be planned with the same rigor as any other asset, while respecting any personal or emotional ties.
• Risk tolerance reflects your willingness to endure volatility, while risk capacity measures your financial ability to recover from losses.
• Bond funds and individual bonds are functionally similar, especially when held to maturity.
• Negotiating with employers or job hopping can be effective short-term paths to higher pay. Building side businesses or securing equity participation can create outsized wealth growth over time.
• Investors don't need crypto in their portfolios, but understanding how it works helps in today's financial landscape.

Key Timestamps:
(01:58) – Question #1: Understanding Risk and Reward in Investing
(15:01) – Question #2: David's Early Retirement Strategy
(22:21) – Question #3: Karen's Question on Risk Capacity
(31:09) – Question #4: James' Concern About Bond Funds
(42:39) – Question #5: Tips for Increasing Your Income
(48:20) – Strategic Career Climbing
(53:47) – Question #6: Introduction to Cryptocurrency
(01:00:33) – The Role of Trust in Money and Bitcoin
(01:09:16) – Bitcoin Wallets and Blockchain Explained
(01:13:27) – Cryptographic Puzzles and Proof of Work
(01:24:37) – Concluding Thoughts and Future Episodes

Key Topics Discussed:
The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques

Mentions:
https://bestinterest.blog/risk-and-reward/
https://bestinterest.blog/stocks-for-wealth-bonds-for-sanity/
https://bestinterest.blog/winning-the-game-retiring-at-57-with-4-million/
https://bestinterest.blog/raises-negotiations/
https://bestinterest.blog/explaining-bitcoin-in-simple-terms/

More of The Best Interest:
Check out the Best Interest Blog at https://bestinterest.blog/
Contact me at jesse@bestinterest.blog
Consider working with me at https://bestinterest.blog/work/

The Best Interest Podcast is a personal podcast meant for education and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.