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.

On Jesse's 11th "Ask Me Anything" episode, he unpacks four questions that sit at the center of real-life financial decision-making. He starts with a grounded look at the 15-year vs. 30-year mortgage debate, cutting through rules of thumb to show how interest rates, liquidity, cash-flow, and even your personal comfort with debt shape the right choice far more than blanket advice ever could. From there, he turns to the under-discussed strategy behind Health Savings Accounts—why the "invest and reimburse later" approach works, when it stops working, and how the tax bomb of leaving HSA dollars to non-spouse heirs should change how listeners think about funding and spending those accounts in their 50s and beyond. In a detailed case study, Jesse walks through a listener's complex 2026 tax year involving rental-property capital gains, ACA cliffs, Social Security timing, and potential Roth conversions, revealing how layered tax rules—income brackets, capital gains stacking, depreciation recapture, and NIIT—interact in ways that can either save or silently cost retirees thousands. And finally, he tackles whether a diehard DIY investor or Boglehead should ever hire a financial planner, drawing a sharp distinction between the "Uncle Franks" who truly live and breathe this stuff and the "Nicks" who love markets but miss the deeper planning work. With clarity, nuance, and practical wisdom, Jesse shows listeners not just what to do, but how to think through the tradeoffs that define good long-term planning.

Key Takeaways:
• A 15-year mortgage saves significant interest, but the higher monthly payments reduce cash-flow flexibility and increase default risk.
• A 30-year mortgage often wins mathematically when investors "invest the difference," thanks to potentially higher long-term market returns versus fixed loan rates.
• Choosing a mortgage term is partly a psychological decision, not just a financial optimization.
• HSA dollars become a tax trap if left to non-spouse heirs, who must treat the entire balance as taxable income in the year of inheritance.
• Selling a rental property triggers both capital gains and depreciation recapture, which can dramatically increase taxable income in that year.
• DIY investors vary widely—some are true experts, while others know just enough to make avoidable mistakes.

Key Timestamps:
(02:04) – 15-Year vs. 30-Year Mortgage Debate
(11:03) – Liquidity and Mortgage Payments
(13:48) – HSA Accounts: When to Fund and When to Use
(25:37) – Spending Down HSA Balances
(26:39) – Allison's Financial Planning Dilemma
(29:05) – Analyzing Capital Gains and Tax Implications
(35:49) – Considering Social Security Timing
(38:54) – The Role of Financial Planners for DIY Investors

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/

Personal Finance for Long-Term Investors 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 sits down with Andy Hill—personal finance educator, podcast host, and creator of Marriage, Kids, and Money—for a candid conversation about building wealth while building a life you actually enjoy. Andy shares how a mix of financial discipline, intentional goal-setting, and family-centered values helped him and his wife pay off their mortgage by age 35 and achieve financial independence on their own terms. Together, they unpack why traditional FIRE goals often miss the human side of money, how to define "enough," and why generosity and purpose are essential parts of financial freedom. Andy also opens up about the shift from chasing net worth to focusing on net happiness, revealing the moment he realized money was no longer the main goal—but a tool for creating the life and impact he wanted most. Throughout, Jesse and Andy remind listeners that real wealth isn't about numbers—it's about freedom, joy, and using money to live aligned with what truly matters.

Key Takeaways:
• Financial freedom isn't just about money—it's about creating the life and relationships you truly want.
• Family alignment around financial goals strengthens relationships and ensures everyone is moving in the same direction.
• Andy's shift from "net worth" to "net happiness" redefined how he measures success and balance.
• Andy emphasizes financial independence on your own terms, not a one-size-fits-all version of FIRE.
• Clarity creates motivation—when your goals align with personal meaning, saving and investing feel purposeful.
• Sustainability matters more than intensity—consistent, realistic habits lead to long-term financial wellness.

Key Timestamps:
(00:44) – The Value of Time in Financial Planning
(05:16) – The Importance of Buying Back Your Time
(08:31) – Interview with Andy Hill: Owning Your Time
(14:33) – Exploring the Concept of Coast FIRE
(18:51) – Dreaming of a Three-Day Work Week
(22:18) – The Value of Relationships
(25:05) – Practical Tips for Transitioning to a Three-Day Work Week
(29:45) – Involving Kids in Financial Planning
(34:27) – Diversifying Your Identity

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://marriagekidsandmoney.com/
LinkedIn: https://www.linkedin.com/in/andyhillmkm/

Get your pre-copy of Andy's new book here: https://amzn.to/4phCgqF

"Own Your Time: 10 Financial Steps to Put Your Family First and Escape the Corporate Grind" by Andy Hill

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.