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.

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 

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 investments

Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.

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 

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.

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

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 

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