Episodes
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The Tax Cuts and Jobs Act is set to expire in 2026, which could mean higher taxes for many. This upcoming tax law change has many asking: Should I do Roth conversion NOW to lower my taxes?
Roth conversions can save you a lot of money—but you have to weigh multiple factors in a careful way. I’ll cover sample scenarios and careful considerations in today’s episode.
Listen now and learn:
Who benefits most from Roth conversions and why
How timing and your tax bracket can make or break a Roth conversion strategy
4 real-life examples of using Roth conversions to lower taxes
Why a calculated, strategic approach to Roth conversions is essential
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
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In this episode, I’m joined by Marlena Lee from Dimensional Fund Advisors for a deep dive into evaluating investment fads and how to build better portfolios. We also explore the importance of global diversification and why certain investments may not belong in your long-term strategy.
Listen now and learn:
A framework for evaluating whether an investment fad deserves a place in your portfolio.
The truth about private investments and why gold or crypto might not be the hedges you think they are.
Why past performance and company size don’t always indicate future returns.
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
[0:40] Eugene Fama’s Contributions to Finance
[6:39] Evaluating Investment Fads
[11:10] Scarcity, Growth Stocks, and Extrapolating Returns
[14:13] The Importance of Global Diversification
[29:46] Gold and Cryptocurrencies as Investments
[36:36] Hedge Funds and Private Investments
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Missing episodes?
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Things can get complicated quickly in the world of personal finance. From investing and budgeting to estate planning and insurance, there are multiple ways to accomplish what you need to get done.
In today’s episode, you’ll hear an interview I did on “The Struggle Is Real” podcast. This interview dives into how to simplify investing and budgeting in a way that feels more approachable.
Listen now and learn:
What matters whenever it comes to successfully investing
My straightforward investment strategy
The most important factor in investing
How to simplify spending by reverse budgeting
How to enjoy your money as it grows
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
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In this episode, we tackle one of the biggest challenges investors face: making smart, strategic decisions in an unpredictable market.
Drawing inspiration from the game of chess, my guest Rubin Miller will explain how to think several steps ahead when it comes to your portfolio, outmaneuver market uncertainty, and avoid costly mistakes. We also discuss the role of “luck” in investing and how good decisions do not always lead to good outcomes.
With his chess expertise and role as Chief Investment Officer, Rubin has a knack for explaining tricky investment concepts so investors can feel confident in the decisions being made for them.
Listen now and learn:
The similarities and differences in decision making with chess and investing
Why understanding the role of skill and luck is critical for long-term investing success
How tools like options and diversification can help you manage risk and build a resilient portfolio
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
[0:54] Chess, Investing, and the Art of Navigating Uncertainty
[09:17] The Role of Skill and Luck in Investing
[11:49] The Japanese Mochi Company: Focusing on What You Do Best
[17:02] Certainty vs. Uncertainty: Building a Thoughtful Portfolio
[24:02] The Challenges of Portfolio Construction
[29:04] The Role of Options in Risk Management
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When a CD matures, you have several options: renewing the CD, moving the funds to a high-yield savings account, or exploring higher-risk, higher-reward investments. Each choice comes with its own set of benefits and drawbacks.
Listen now and learn:
Strategies for maximizing your earnings
Whether you should renew your CD or move to a high-yield savings account
When to move your cash to higher-risk, higher reward investmentsVisit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
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Wes Gray, founder of Alpha Architect, joins the show to explore the evolution from traditional stock picking to data-driven quantitative investing.
Listen now and learn:
Why even a perfect stock-picking strategy can still fail during market downturns
The power of factor investing and how it systematically enhances portfolio returns
A critical perspective on investing in emerging markets and private equity
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
[0:30] From Stock Picker to Quant: Wes Gray’s Investing Journey
[8:39] The Efficient Market Hypothesis and the Reality of Active Investing
[12:29] Factor Investing Explained
[19:31] Why Value Investing Has Struggled
[29:54] The Role of Momentum in a Portfolio
[33:36] A Critical Look at Emerging Markets and Private Equity
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In the realm of investing, nothing is more seductive than picking a winning stock. Unfortunately, investing in individual stocks is incredibly risky. But here’s the good news: picking winning stocks isn’t necessary.
Listen now and learn:
A history of individual stock returns
How professional investors perform
The best way to own winning stocks
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
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Taylor Schulte joins the show for a dive deep into the world of dividend investing. Tune in as we debunk common myths and provide a clear framework for building a successful investment portfolio.
Listen now and learn:
The drawbacks of chasing high-yield investments and how to build a balanced portfolio
How dividend-focused funds perform relative to the market
Tax implications of dividends vs stock buybacks
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
[0:30] Introduction to Dividend Investing and Common Misconceptions
[4:45] Building a Portfolio: Yield Focus vs. Total Return Approach
[12:30] Performance of Dividend Strategies
[17:30] Understanding Buybacks and Tax Implications
[22:15] Retirement Income Strategies and Aligning Investments with Goals
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With the S&P 500 rapidly declining over the past two weeks, what should investors be doing?
Listen now and learn:
How often the stock market falls
What triggered the most recent stock market decline
Timeless wisdom for periods of stock market losses
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions. -
If you want to maximize your investing returns beyond what traditional methods offer, discover leading edge opportunities, or simply stay up to date on the latest investing trends, alternative investments may be for you. The pursuit of diversification is not as straightforward as it once was — and the classic 60/40 portfolio may no longer be sufficient in helping investors achieve their financial goals. Alternative assets are emerging and may start to play a more prominent role in future investor portfolios.
This episode is recorded LIVE from the 2024 Morningstar Investment Conference with Phil Huber. He's the Chief Investment Officer for a multi-billion dollar wealth management firm and author of The Allocator’s Edge: A Modern Guide to Alternative Investments and the Future of Diversification.
Listen now and learn:
Why traditional asset allocation strategies may face challenges going forward
How private credit has emerged as one of the fastest growing alternative asset classes
The benefits of interval funds relative to traditional drawdown funds
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
[02:23] The Case for Alternative Investments
[06:15] Understanding and Implementing Alternatives
[09:37] Educating Clients on Alternatives
[14:21] Exploring Private Equity
[16:45] The Rise of Private Credit
[23:52] Interval Funds: A Modern Solution
[32:14] Crafting an Alternative Investment Strategy
[36:09] Effective Communication and Benchmarking
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In this episode, we're dissecting a strategy that many believe is a must-do for every investor: Tax-Loss Harvesting (TLH). But what if I told you that this widely recommended tactic might not be beneficial for everyone?
Listen now and learn:
The three components necessary to derive value from tax loss harvesting
Reasonable expectations of value from tax loss harvesting
Actions you can take to maximize the potential benefits of tax loss harvesting
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions. -
If you’ve ever felt anxious or overwhelmed by market volatility, don't miss this episode. I’m joined by Darius Foroux, a newsletter writer to 100,000 subscribers and author of the brand new book The Stoic Path to Wealth. His steady approach helps investors navigate the chaos of modern-day markets with discipline, emotional distance, and self-mastery.
Listen now and learn:
How a Stoic approach to investing leads to better consistency and less emotional decisions
The role education and skill-building play in achieving financial freedom
Essential stock market fundamentals and practical strategies for financial success
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
[1:57] Importance of Investing and Challenges Investors Face
[06:40] Managing Emotions and Staying Consistent
[13:33] The Role of Education in Financial Success
[19:03] Understanding the Stock Market
[28:58] Balancing Life and Investing
[35:22] Practical Wisdom and Strategies for Investors
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This episode dives into a topic that grabs investors’ attention every four years: the Presidential election.
The potential impact on the economy, policy, and markets often leads to increased anxiety and speculation.
Listen now and learn:
The historical impact of elections on the stock market
How markets have performed during different presidencies
A framework for thinking about investment decisions during election season
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions. -
There are few topics as broadly misunderstood as US government spending and, as a result, many conversations regarding Social Security are off the mark. The financial well-being of Social Security is obviously important from a policy perspective, but perhaps even more important from a financial planning and personal investment perspective.
Listen now and learn:
The sustainability of Social Security
Potential policy changes to Social Security
How to account for Social Security in your financial plan
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions. -
The US national debt is a significant and often misunderstood topic: With the current debt sitting at around $34.6 trillion, many wonder if this signals an impending crisis. Peter breaks down what this figure means and explores the broader implications (many of which may surprise you).
Listen now and learn:
Differences between the deficit, the debt, and the debt ceiling
How US government finances are very different than household finances
Why inflation, not default, is the real risk of our deficit spending
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
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While the US dollar currently enjoys a dominant position as the world's reserve currency, various factors could challenge its supremacy. Emerging economies, digital currencies, geopolitical shifts, and global financial reforms all pose potential threats. Understanding these dynamics is crucial for navigating the future of global finance.
Listen now and learn:
What it means to be a reserve currency
Why the US dollar is the dominant reserve currency
The probability and implications of the US dollar losing its reserve status
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions. -
Jesse Cramer, author of The Best Interest, joins the show to share his in-depth research into the astounding math behind car ownership. This episode originally aired in 2023 and was a top interview of the year. Although this is a replay, the content shared is just as relevant today and important to consider for the impact big purchases can have on your finances.
Listen now and learn:
How to evaluate the impact of time owned vs miles driven
When purchasing a used car is smarter than buying a new car
How leasing compares to owning from a cost perspective
To see the original show notes, YouTube interview, and resources visit this page: EP 116: The Astounding Math Behind Car Ownership with Jesse Cramer.
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.TIMESTAMPS
(4:08) The Primary Costs of Car Ownership
(11:08) Buy a New Car vs Buying a Used Car
(17:48) The Difference in Cost of Owning a Gas vs Electric Vehicle
(19:08) Evaluating a Car’s Utility
(28:08) Buying a Car vs Leasing a Car
(32:08) When to Repair a Car vs Buy a Car
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The problem with conventional wisdom is that it represents the masses, but there's a whole host of things that conventional wisdom gets wrong. By default, that feeds into what investors get wrong. This episode with Ashby Daniels originally aired in 2023 and was a top interview of the year. Although this is a replay, the content shared is just as relevant today and important to consider for your investing strategy and how you think about risk.
Listen now and learn:
What investors get wrong
A new way to think about risk
How to define investment success
To see the original show notes, YouTube interview, and resources visit this page: EP 104: Challenging Conventional Wisdom with Ashby Daniels.
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.TIMESTAMPS
(3:32) Blaming the Market Instead of Yourself
(10:03) Defining Risk
(16:49) How to Define Investment Success
(21:33) No Need to Be Smart. Just Don’t Be Stupid
(30:48) Investing Like an Optimist
(35:57) The Value of a Financial Advisor
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Michael Kitces is one of the industry’s leading experts on all things financial advice and financial planning. In this live episode recorded at Wealth Management EDGE, Michael explains the evolution of financial advice and how AI might impact the profession going forward. This episode originally aired in 2023 and was a top interview of the year. Although this is a replay, the content shared is just as relevant today and important to consider for the evolution of financial advice.
Listen now and learn:
The evolution of financial advice from the 1960s to present
Ways consumers benefit from financial advisors moving up the value chain
How AI might impact the financial advice profession
To see the original show notes, YouTube interview, and resources visit this page: EP 102: AI and the Evolution of Financial Advice with Michael Kitces [LIVE]
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.TIMESTAMPS:
(3:33) The Evolution of Financial Advice
(12:33) The Lack of Barriers to Entry for Giving Financial Advice
(18:33) The Impact of AI on the Financial Advice Profession
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In this episode, I’m joined by Carl Richards, a Certified Financial Planner (CFP®) and creator of the Sketch Guy column, appearing weekly in The New York Times since 2010. This episode originally aired in 2023 and was a top interview of the year. Although this is a replay, the content shared is just as relevant today and important to consider for your investing strategy.
Listen now and learn:
How investors fall victim to the behavior gap
What it means to do real financial planning
The best way to avoid “The Big Mistake”
To see the original show notes, YouTube interview, and resources visit this page: EP 100: What Real Financial Advice Means with Carl Richards.
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
TIMESTAMPS:
(04:30) What is the Behavior Gap?
(07:45) Why Investors Get Distracted
(11:05) What Investors Need When Markets Are Scary
(17:30) Real Financial Planning
(24:30) Getting Ahead vs. Having Enough
(30:00) The Value of a Real Financial Advisor
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