Smart Year-End Tax Tips to Reduce Investment Taxes in Retirement (EP.181)

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. -----  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

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. -----  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.

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

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

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.

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.

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  

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  

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