Personal Finance for Long-Term Investors - The Best Interest

The speaker defends choices that look irrational on paper but suit real life and values. Topics include keeping a small sandbox for speculative bets, paying low-interest loans for peace of mind, and when leasing a car or holding extra cash makes sense. He covers HSA use for present needs, timing Social Security for emotional security, and the virtues of lazy, simple investing.

Jeremy Keil, a Certified Financial Planner and author of 'Retire Today', shares insightful strategies for effective retirement planning. He discusses the concept of 'retirement longevity', emphasizing why many retire earlier than expected. Keil introduces the importance of personalized life expectancy modeling and framing Social Security as insurance. He outlines a five-step Retirement Master Plan that highlights the power of tax strategy and Roth conversions. The conversation blends technical insights with emotional challenges retirees face, offering a practical roadmap for confidence in retirement.

This engaging discussion dives into whether 2026 could be your year to retire, emphasizing the importance of flexibility over market timing. Jesse explores the pitfalls of market valuations and the necessity of rebalancing, while also addressing sequence-of-returns risk for early retirees. The conversation turns practical as he shares insights on getting kids and grandkids started with investing through various accounts. Listeners learn about crucial financial milestones and how to adjust their portfolios as they age, combining technical advice with behavioral wisdom.

In this Christmas episode, Jesse steps back from year-end checklists and market noise to tell a more personal story—one shaped by the "ghosts" of his financial past, present, and future. He begins with the early experiences that formed his relationship with money: a summer concession stand that taught him pricing, customer focus, and the power of simply telling people what you do; a first job cleaning bathrooms at a state park that clarified the difference between earning a paycheck and building a career; and the moment in his mid-20s when seeing real dollars in his 401(k) pulled him into a decade-long deep dive on personal finance, blogging, and eventually a full career change into wealth management. From there, he pivots into a transparent walkthrough of his current systems—how he and his wife structure savings, manage cash, use insurance, approach debt, track spending, and design an investment allocation that reflects real life rather than theory. He also shares three planning cases from this year that reveal the human side of financial advice: navigating retirement after a family death, unwinding concentrated stock risk for a high-earning executive, and giving one engineer the peace of mind to sleep through layoff fears. Looking ahead, Jesse reflects on where the industry is headed—AI-enabled tools, changing fee models, and a shift toward values-based planning—while outlining how he and his family think about the future with a firm grip on flexibility, priorities, and the fleeting years of raising young children. It's an intimate, thoughtful close to the year—less about spreadsheets and more about why financial planning matters in the life you're actually living. Key Takeaways: • Take time to seek out new opportunities. Putting yourself out there for advancement is one of the most straightforward ways to advance financially. • Getting "skin in the game" with real dollars in a 401(k) or investment account is often the catalyst for learning personal finance at a deeper level. • A blended approach to retirement savings (401(k), Roth IRA, HSA) builds both tax flexibility and long-term resilience. • Cash-management infrastructure—joint accounts, high-yield banks, and legacy accounts—matters less than ensuring clarity, shared access, and ease of use. • Tools like the state-run CHIP/Child Health Plus programs can dramatically reduce healthcare costs for families with children. • Strong personal finances create flexibility: the ability to enjoy life now while still protecting the future—especially during the irreplaceable years of raising children. Key Timestamps: (04:22) – Financial Past: Early Money Lessons (07:09) – Entrepreneurial Beginnings: The Concession Stand (10:36) – First Job Experiences and Lessons Learned (20:20) – Financial Present: Family Finances and Planning (26:23) – Our Investment Strategy (32:58) – Tax Planning Insights (37:25) – Evolving Budgeting Methods (45:08) – Financial Future: What Will You Make of It? 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.

Explore the trade-offs between 15-year and 30-year mortgages, discovering how personal comfort with debt influences your decision. Dive into the ins and outs of Health Savings Accounts, including the risks tied to leaving them to heirs and strategies for maximizing their tax benefits. Unravel a complex tax case involving rental properties and the ACA's financial maze. Finally, debate whether DIY investors should engage a financial planner, weighing the pros and cons of expert guidance versus self-management.

In this dialog, Andy Hill, a personal finance educator and podcaster known for his work on Marriage, Kids, and Money, reveals how he achieved financial independence while prioritizing family. He discusses his shift from chasing net worth to embracing net happiness, emphasizing that true wealth is about freedom and joy. Andy introduces the concept of Coast FIRE and shares his family's journey to financial stability, including creative strategies for part-time work, parenting with purpose, and the importance of aligning financial goals with personal values.

In this conversation, Phil Pearlman, a psychologist and founder of the Pearl Institute, shares his insights on the intersection of health and wealth. He discusses the holiday season's impact on wellness and emphasizes his 'four pillars of health': nutrition, exercise, sleep, and love. Phil highlights the dangers of alcohol and processed foods while offering practical tips for maintaining healthy habits during festivities. He advocates for starting small with one sustainable change, like morning walks, to inspire long-lasting transformation.

Dive into the world of direct indexing versus ETFs, where complexity often outweighs the promised benefits. Understand how couples can tackle financial discrepancies when their retirement timelines don’t align, including tips on joint versus separate tax filing. Explore the art of decumulation—strategizing withdrawals for retirement can extend your portfolio's lifespan, minimize taxes, and ensure financial stability. Uncover the roles of social security, HSA, and common pitfalls in withdrawal strategies to pave the way for a confident retirement.

Join behavioral finance researcher John Dinsmore, author of The Marketing of Debt, as he uncovers how marketing manipulates our financial choices. He reveals how AI-driven ads exploit human biases like loss aversion and over-optimism, making us more vulnerable to impulsive buying. Dinsmore discusses real-life examples of how marketing influences even the savviest consumers, especially retirees, who are often targeted by complex financial products. Most importantly, he shares strategies to recognize and defend against these persuasive tactics.

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.