Jesse is joined by Cullen Roche—financial writer, macro thinker, and founder of Discipline Funds—for a clear-eyed conversation about how money actually works, why so much financial commentary gets it wrong, and how investors can make better decisions by understanding the plumbing beneath markets. Together, they unpack the core mechanics of the modern monetary system, including how government spending, deficits, and interest rates function in practice rather than theory, and why fears around debt and inflation are often oversimplified or misapplied. Cullen explains the crucial distinction between households and currency issuers, challenges common narratives around money printing and fiscal irresponsibility, and outlines how misconceptions about macroeconomics can lead investors to poor asset allocation decisions. The discussion also explores portfolio construction through the lens of economic regimes, the role of cash and bonds as stabilizers rather than return drivers, and why discipline and risk management matter more than prediction. Throughout, Jesse and Cullen emphasize that understanding monetary operations is not about forecasting markets, but about grounding financial decisions in reality, humility, and process—especially in a world saturated with confident but flawed macro narratives.

Key Takeaways:
• Governments that issue their own currency operate under fundamentally different constraints than individuals.
• Understanding monetary plumbing helps investors avoid emotional macro reactions.
• Narratives are persuasive but frequently misleading. Sound investing focuses on process over storytelling.
• Portfolio construction should reflect multiple possible economic outcomes.
• Understanding how money moves reduces fear-driven decisions.
• Long-term success depends more on behavior and discipline than on being "right" about the economy.

Key Timestamps:
(01:50) – The Intellectual Side of Investing
(06:39) – Efficient Market Hypothesis and Index Investing
(11:43) – The Super Investors of Graham and Doddsville
(14:44) – Cullen Roche Joins the Show
(25:18) – Understanding High Expectations and Stock Volatility
(30:12) – Target Date Funds and Customizing Portfolios
(36:42) – Government Debt and Fiscal Policy Concerns
(43:04) – Balancing Complexity and Simplicity in Financial Plans
(49:15) – Cullen Roche's Perfect Portfolio

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://ria.disciplinefunds.com/
LinkedIn: https://www.linkedin.com/in/cullenroche/
Mentions:
Your Perfect Portfolio: The ultimate guide to using the world's most powerful investing strategies by Cullen Roche
Pragmatic Capitalism: What Every Investor Needs to Know About Money and Finance by Cullen Roche

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 13th AMA episode, he steps back from tactics and returns to first principles, answering listener questions that cut to the core of what financial planning actually is—and what it is not. He begins by dismantling the common assumption that a portfolio and a financial plan are interchangeable, explaining why investing is only one component of a much broader process that aligns cash flow, risk, taxes, goals, and life transitions across decades. From there, Jesse walks listeners through his end-to-end financial planning framework, starting with values and goal clarification, moving through balance sheets, cash flow, taxes, insurance, and estate planning, and ending with implementation and ongoing iteration as life evolves. Using the example of young adults in their 20s, he highlights where early financial energy is best spent: awareness of spending, intentional goal-setting, early investing for learning and compounding, and developing human capital through career growth. The episode closes with a thoughtful response to a fellow planner's question about client inertia, blending behavioral finance and lived experience to explain why busy, successful people often delay planning—and how patience, education, structure, and progress over perfection can create momentum without coercion. Throughout, Jesse reinforces a central theme: real financial planning is not about perfect portfolios, but about creating clarity, flexibility, and forward motion in an uncertain and deeply human life.

Key Takeaways:
• A portfolio and a financial plan are not the same thing. Investing is only one component of comprehensive financial planning.
• Your financial plan must align money with goals, values, and life realities.
• Financial plans must evolve as careers, families, and health change.
• Career growth can compound more powerfully than portfolio tweaks.
• Client inertia is usually about time, emotion, or uncertainty—not laziness.
• The ultimate goal of planning is clarity, flexibility, and peace of mind. Progress does not have to be linear or immediate to be meaningful.

Key Timestamps:
(01:34) – Investing vs. Financial Planning
(10:27) – Building a Financial Plan from Scratch
(16:33) – Analyzing Your Financial Snapshot
(20:00) – Identifying Financial Risks and Making Changes
(22:28) – Key Financial Advice for Young Adults
(27:09) – Overcoming Client Hesitation in Financial Planning
(33:31) – The Human Element in Financial Planning

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.

In this candid solo episode, Jesse walks through a series of financial decisions that look "wrong" on paper but make complete sense when viewed through the lens of real life, values, and tradeoffs. Using personal examples, he challenges the idea that optimal spreadsheets should always dictate behavior, arguing instead that financial planning exists to support a life well lived—not to win theoretical efficiency contests. Jesse explains why holding excess cash even when expected returns favor investing, and prioritizing flexibility and simplicity over marginal tax optimization. Throughout the episode, he dismantles the myth that good planning means eliminating all inefficiency, emphasizing that peace of mind, optionality, and behavioral alignment often outweigh incremental gains. By reframing "dumb" financial moves as intentional choices made with eyes wide open, Jesse encourages listeners to separate true financial mistakes from decisions that are simply mismatched to someone else's values or risk tolerance—and to give themselves permission to choose what actually works for their lives.

Key Takeaways:
• Not all financially "inefficient" decisions are mistakes. Optimization often ignores behavioral and emotional realities.
• Taking care of a low interest loan can offer peace of mind—despit better returns often being found in investments.
• Leasing a car or renting a home may be the right move—depending on the situation.
• Using an HSA early may seem like a bad idea, but it could help reduce stress elsewhere in our financial lives.
• Being a "lazy investor" is often better than being a complicated investor.
• Spreadsheets cannot fully capture human behavior. A "good" decision can look bad to outsiders and still be right.

Key Timestamps:
(00:46) – Sandbox Investing Accounts
(04:48) – Paying Off Low-Interest Loans
(09:37) – Leasing a Car: Pros and Cons
(13:05) – Emergency Funds and Cash Allocation
(19:56) – Balancing Emotions and Math in Social Security Decisions
(22:17) – Owning Company Stock: Risks and Rewards
(23:33) – Taxable Brokerage Accounts vs. Qualified Retirement Accounts
(27:55) – Using HSA Accounts for Medical Expenses
(29:51) – Renting vs. Buying: A Balanced Perspective
(34:52) – The Concept of Lazy Investing
(39:59) – Continuous Learning in Personal Finance

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.