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Proactive tax planning could save you thousands. If you're ready to hire an advisor, my team at Plancorp is here to help. Schedule a call today to learn more.
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Avoiding tax surprises isn’t just about filing on time—it’s about planning ahead.
This episode shares six real life examples of how tax projections can potentially save you thousands on your future taxes and thoughtfully guide the bigger picture of your financial plan. Learn actionable strategies for reducing your tax liability, whether you’re managing retirement withdrawals, timing business expenses, or exploring Roth conversions.
Listen now and learn:
Why tax projections are essential for proactive financial planning.
Strategies for minimizing taxes on Social Security, RMDs, and capital gains.
How to use tax projections to optimize your financial decisions year-round.
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions. -
Thinking about hiring a financial advisor? It could be a great decision—if you know how to evaluate them. Get my free worksheet to follow a proven process and avoid common mistakes.
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Navigating equity compensation can be tricky, especially when the year-end tax clock is ticking.
In this episode, Ally Jane Ayers, a leading expert in the complex world of equity compensation, shares tax-smart strategies to optimize your stock options, RSUs, and equity packages. Whether you hold RSUs, ISOs, or stock options at a private company, Ally’s insights will help you tackle tricky tax issues, reduce over-concentration risks, and align your equity with your financial goals.
Listen now and learn:
Key tax considerations for equity compensation before December 31.
How to avoid costly under-withholding on RSUs.
Advanced strategies to diversify concentrated stock positions and preserve gains.
The power of 10b5-1 plans for stress-free stock selling.
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
[00:37] Key Tax Considerations for Year-End Stock Compensation Planning
[03:54] The Importance of Multiyear Equity Planning
[09:24] Exercising Stock Options at Private Companies
[14:10] Managing Risk with Equity Compensation
[22:27] Advanced Strategies for Managing Mixed Equity Packages
[25:38] Creative Ways to Preserve Gains and Minimize Taxes
[32:49] Leveraging 10b5-1 Plans for Stress-Free Selling
[34:56] Final Tips for Equity Compensation Holders
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Want a peek behind the scenes? Get my top 5 must-read financial articles that keep me ahead on innovative planning and investment strategies—exclusive, curated, and straight to your inbox bi-weekly when you sign up for my newsletter.
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Are you paying more in taxes than you need to?
As the year winds down, now’s an ideal time to make smart moves that can lower your tax bill—especially if you’re close to or in retirement.
In this episode, I share simple, practical strategies to help you keep more of your money. From making the most of tax-friendly accounts to reducing the bite of capital gains, these tips can make a real difference in your finances while keeping your long-term goals on track.
Listen now and learn:
Easy ways to lower your tax bill before the year ends
How to make sure you’re not paying more taxes on investments than necessary
The best ways to plan for your retirement income and avoid costly tax surprises
Common mistakes people make with taxes—and how to steer clear of them
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
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What’s the role of bonds in your retirement portfolio in a high-yield environment?
In this episode, PIMCO’s David Braun breaks down the evolving fixed-income landscape. With 30 years of investment expertise, he shares insights on how rising yields create opportunities, why active management is essential for bonds, and what the U.S. national debt means for investors.
Listen now and learn:
The role of core bonds in retirement planning
Why active management outshines passive strategies in fixed income
Emerging trends shaping the future of fixed income investing
How rising U.S. debt levels could impact bond yields and risk profiles
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
[00:30] What is the Role of Core Bonds in a Portfolio?
[04:46] Rising Yields and Resetting Expectations for Bonds
[10:00] Active vs. Passive Management in the Bond Market
[19:12] National Debt and Implications for Bond Investors
[27:26] Future Trends in Fixed Income Investing
[31:42] Addressing Misconceptions About Bond Math
[34:34] Closing Thoughts and Resources
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What does it take to think clearly and stay rational in a world full of financial noise?
This episode features part two of a rare conversation with Jason Zweig, acclaimed financial journalist and author of Your Money & Your Brain. From behind-the-scenes wisdom gleaned from Warren Buffett and Charlie Munger to the psychology driving your financial decisions, Jason delivers invaluable insights that will reshape how you think about investing.
Listen now and learn:
Lessons from legendary investors and their surprising strategies
How cognitive biases and dopamine affect your financial decisions
Why creating investing rules is key to long-term success
The future of finance: from indexing to cryptocurrency
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
TIMESTAMPS:
[00:30] Jason Zweig’s Unplanned Path to Financial Journalism
[04:06] Pivotal Advice: “Don’t Get Anyone’s Blood on Your Hands”
[07:31] Learning from Industry Giants: Wisdom from Buffett, Munger, and Others
[11:10] Daniel Kahneman’s Work on Cognitive Illusions
[15:20] Neuroeconomics: A Window (and a Mirror) into Investor Behavior
[19:14] The Brain on a Hot Streak: Dopamine and Anticipation
[24:10] Laughing at Wall Street: Creating The Devil’s Financial Dictionary
[29:08] Questioning the Future of Finance
[34:13] A Lesson from the Antiques Market: Not Everything Always Holds Value
[39:05] Price Feels Like Proof: The Trap of Anchoring on Success
[41:18] What Excites Jason Zweig About the Future of Investing
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Are today’s markets testing your patience, or making you question your strategies? Jason Zweig believes that timeless investment wisdom is more relevant now than ever.
In this episode, we’re recording live from the New York Stock Exchange as Zweig discusses why Benjamin Graham’s "The Intelligent Investor" remains a cornerstone of disciplined investing. Zweig shares insights on the psychological challenges investors face, the role of human nature in decision-making, and why mastering market psychology is key to achieving lasting success.
Listen now and learn:
Why core investment principles remain crucial in a fast-paced world
How to make market psychology work for, not against, you
Strategies to recognize and manage emotional biases in investing
The true meaning of being an intelligent investor
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
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Markets are driven by countless factors—consumer demand, innovation, interest rates, global trade, and more. Sure, policies can create a little wind in the sails for certain segments of the market, or a bit of a headwind, but presidents don’t hold the wheel.
Listen now and learn:
The limited impact of politics on stock markets
The challenges faced by the US economy
How the US stacks up in the two most important drivers of economic growth
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
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Are we entering a decade of low returns?
Goldman Sachs projects that S&P 500 returns will average only 3% annually over the next ten years—far below the historical norm of 13% in the last decade. While I’m not a believer in predicting the future, there are several useful elements in their research worth discussing.
In this episode, I’ll explore what’s behind this forecast and what it means for investors. Plus, how to adapt to the shifting landscape with strategies that go beyond the traditional S&P 500.
Listen now and learn:
How one goes about forecasting future returns in the first place
Historical instances where stocks underperformed cash for more than a decade
Implications and actionable considerations for a period of lower US stock returns
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions. -
What happens if the spouse who handles all the finances suddenly isn’t there?
In this episode, Senior Wealth Manager Sara Gelsheimer of Plancorp joins us to explore why both spouses need to be involved in financial decisions. Whether due to sudden life changes or the realities of aging, having only one financial decision-maker can leave the other spouse unprepared for critical responsibilities. Sara shares practical steps and real-life examples that highlight the importance of financial involvement for both partners.
Listen now and learn:
The risks of relying on a single household financial decision-maker
Actionable steps the “non-money” spouse can take to build confidence
How couples can foster financial alignment and open communication
The benefits of choosing an advisor both spouses trust
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
[00:04] The Risks of Having Only One Financial Decision-Maker
[02:24] Key Statistics on Women and Financial Literacy
[04:41] The Benefits of Both Spouses Being Financially Informed
[06:16] Real-Life Examples of Preparing Non-CFO Spouses
[11:05] Actionable Steps for the Non-CFO Spouse
[14:48] How the CFO Spouse Can Help Their Partner
[18:33] How to Choose a Financial Advisor for Both Spouses
[22:50] Resources for the Non-CFO Spouse
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Do you feel like something’s missing, even with a solid financial foundation? Or wonder if there’s a better way to use your money for happiness?
In this episode, I sit down with Daniel Crosby, Ph.D., behavioral finance expert and author of The Soul of Wealth, to discuss why the traditional approach to money often leaves us wanting more—and what actually leads to lasting satisfaction. Tune in to learn how to align your financial journey with deeper values, break free from social comparison, and take practical steps toward a more meaningful, joy-filled life.
Listen now and learn:
The best way to spend money on yourself
How social comparison impacts financial decisions
Why relationships have such a powerful impact on financial well-being
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
[0:30] The Inspiration Behind The Soul of Wealth
[2:10] Charitable Giving and the Path to Abundance
[05:15] Investing in Your Well-Being and Personal Development
[10:10] The Impact of Social Comparison on Financial Decisions
[17:00] Developing Better Habits for Financial Success
[23:00] The Power of Relationships in Wealth and Happiness
[27:30] The Link Between Money and Happiness
[33:20] Continual Learning and the Power of Novelty
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In this episode, we sit down with Josh Brown, CEO of Ritholtz Wealth Management, to explore the major shifts shaping Wall Street and what they mean for today’s investors. From the rapid rise of private equity and alternative investments to the growing influence of passive investing, Josh breaks down the trends every investor needs to understand.
Listen now and learn:
Why private equity and alternative investments are gaining traction
The top 3 ways advisors add value beyond just picking investments
How technology is helping investors avoid emotional decisions during market corrections
Whether you’re a DIY investor or work with an advisor, this episode will give you a clear view of the forces driving today’s financial landscape—and how you can use them to your advantage.
Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.
[1:10] The Shift from Traditional Media to Blogs and Social Media
[6:10] The Growth of Passive Investing and its Impact on Wall Street
[9:05] Private Equity and Alternative Investments
[17:45] Advisors' Role in Navigating Financial Trends
[24:50] The Value of Financial Advisors and DIY Investors
[28:00] Market Corrections and Investor Behavior
[39:50] Josh Brown’s Work on Billions
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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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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. - もっと表示する
