The Long Term Investor

Peter Lazaroff
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Oct 8, 2025 • 13min

Trapped By Taxes? How 351 Exchanges Let You Diversify Without Selling Your Stock (EP.225)

Wondering if you’re making the right financial moves? Let’s build a strategy you can rely on. Schedule a call with Peter to get professional guidance. -----  Many investors want to diversify out of a few appreciated stocks but can’t stomach the tax bill that comes with selling. In this episode, Peter Lazaroff explains how Section 351 exchanges give investors a smarter, tax-efficient way to move from concentrated stock positions into diversified ETFs–without triggering immediate capital gains. Listen now and learn: ► What a 351 exchange is and how it works ► Who’s a good candidate–and who isn’t ► Questions to ask an advisor before pursuing one    Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠)     Disclosure: This content, which contains security-related opinions and/or information, is provided for informational purposes only and should not be relied upon in any manner as professional advice, or an endorsement of any practices, products or services. There can be no guarantees or assurances that the views expressed here will be applicable for any particular facts or circumstances, and should not be relied upon in any manner. You should consult your own advisers as to legal, business, tax, and other related matters concerning any investment. The commentary in this “post” (including any related blog, podcasts, videos, and social media) reflects the personal opinions, viewpoints, and analyses of the Plancorp LLC employees providing such comments, and should not be regarded the views of Plancorp LLC. or its respective affiliates or as a description of advisory services provided by Plancorp LLC or performance returns of any Plancorp LLC client. References to any securities or digital assets, or performance data, are for illustrative purposes only and do not constitute an investment recommendation or offer to provide investment advisory services. Charts and graphs provided within are for informational purposes solely and should not be relied upon when making any investment decision. Past performance is not indicative of future results. The content speaks only as of the date indicated. Any projections, estimates, forecasts, targets, prospects, and/or opinions expressed in these materials are subject to change without notice and may differ or be contrary to opinions expressed by others. Please see disclosures here.
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Oct 1, 2025 • 31min

Year-End Tax Planning After the OBBBA (EP.224)

In this insightful discussion, tax expert Susan Jones from Plancorp dives into year-end tax strategies shaped by the One Big Beautiful Bill Act (OBBBA). She demystifies shifts in charitable deductions and tax implications for high earners, including the new 2% AGI floor. Jones also emphasizes the importance of timing for pre-retirees and business owners in managing income spikes and leveraging benefits like the QBI and bonus depreciation. If you're navigating complex tax waters, her expert insights could be invaluable!
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Sep 24, 2025 • 15min

Bond Funds vs Individual Bonds: What’s Best for Your Portfolio? (EP.223)

Wondering if you’re making the right financial moves? Let’s build a strategy you can rely on. Schedule a call with Peter to get professional guidance. -----  When it comes to bonds, investors often face a tough question: should you own individual bonds or stick with bond funds? In this episode of The Long Term Investor, I break down the trade-offs and explain how bonds really fit into a long-term portfolio. Listen now and learn: ► Why the primary role of bonds is to reduce volatility, not maximize return ► The trade-offs between owning individual bonds vs bond funds ► Why income matters more than price fluctuations for long-term bond returns ► The hidden problems with bond index funds and the case for an active or systematic approach ► How to think about bonds in the context of your overall portfolio strategy Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.   Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠)   Disclosure: This content, which contains security-related opinions and/or information, is provided for informational purposes only and should not be relied upon in any manner as professional advice, or an endorsement of any practices, products or services. There can be no guarantees or assurances that the views expressed here will be applicable for any particular facts or circumstances, and should not be relied upon in any manner. You should consult your own advisers as to legal, business, tax, and other related matters concerning any investment. The commentary in this “post” (including any related blog, podcasts, videos, and social media) reflects the personal opinions, viewpoints, and analyses of the Plancorp LLC employees providing such comments, and should not be regarded the views of Plancorp LLC. or its respective affiliates or as a description of advisory services provided by Plancorp LLC or performance returns of any Plancorp LLC client. References to any securities or digital assets, or performance data, are for illustrative purposes only and do not constitute an investment recommendation or offer to provide investment advisory services. Charts and graphs provided within are for informational purposes solely and should not be relied upon when making any investment decision. Past performance is not indicative of future results. The content speaks only as of the date indicated. Any projections, estimates, forecasts, targets, prospects, and/or opinions expressed in these materials are subject to change without notice and may differ or be contrary to opinions expressed by others. Please see disclosures here.
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Sep 17, 2025 • 33min

M&A, Valuations, and the Future of RIAs — A Conversation with Ian Wenik (EP.222)

Ready to hire an advisor? Whether it’s for retirement planning, proactive tax planning, or navigating complex financial decisions, see how our team at Placorp can help. Schedule a call with Peter now. -----  What’s it really like to cover the RIA and wealth management industry from the inside?  In this episode, I talk with Ian Wenik, Editor at Citywire RIA, about his journey from sports writing to financial journalism, the challenges of running a newsroom, and the trends shaping the future of RIAs. Listen now and learn: ► How Ian went from aspiring sportswriter to covering M&A and valuations in the RIA industry ► What a day in the life of a wealth management journalist actually looks like ► Why private equity, consolidation, and IPOs are reshaping the advisory landscape ► Red flags to watch for when consuming financial news — and how to spot AI-generated “slop”   Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions. [02:30] From sports writing to covering RIAs [05:39] First impressions of wealth management [06:44] Running the newsroom at Citywire [08:09] Balancing breaking news and investigative features [09:47] How Citywire finds and protects sources [12:10] The evolution of RIAs since 2018 [13:51] The future of M&A and RIA valuations [22:27] What content resonates most with advisors [26:40] Where wealth management journalism is headed [30:04] How to read financial news critically   Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠)   Disclosure: This content, which contains security-related opinions and/or information, is provided for informational purposes only and should not be relied upon in any manner as professional advice, or an endorsement of any practices, products or services. There can be no guarantees or assurances that the views expressed here will be applicable for any particular facts or circumstances, and should not be relied upon in any manner. You should consult your own advisers as to legal, business, tax, and other related matters concerning any investment. The commentary in this “post” (including any related blog, podcasts, videos, and social media) reflects the personal opinions, viewpoints, and analyses of the Plancorp LLC employees providing such comments, and should not be regarded the views of Plancorp LLC. or its respective affiliates or as a description of advisory services provided by Plancorp LLC or performance returns of any Plancorp LLC client. References to any securities or digital assets, or performance data, are for illustrative purposes only and do not constitute an investment recommendation or offer to provide investment advisory services. Charts and graphs provided within are for informational purposes solely and should not be relied upon when making any investment decision. Past performance is not indicative of future results. The content speaks only as of the date indicated. Any projections, estimates, forecasts, targets, prospects, and/or opinions expressed in these materials are subject to change without notice and may differ or be contrary to opinions expressed by others. Please see disclosures here.
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Sep 10, 2025 • 17min

Muni Bonds Explained: How To Incorporate Tax-Free Income With Investing For Retirement (EP.221)

Municipal bonds can be a powerful tool for high-income investors, but only when used thoughtfully. In this episode, I explain how to evaluate muni bonds with tax-equivalent yield, the difference between general obligation and revenue bonds, and why I avoid state-specific and high-yield issues. I also share Plancorp’s implementation approach and give a market outlook on why munis remain attractive for retirement portfolios today. Listen now and learn: ► How to tell if municipal bonds make sense for your portfolio ► The key differences between types of muni bonds and what those differences mean for long-term investors ► Why not all muni strategies are created equal—and the hidden risks to watch out for. ► How to think about munis in today’s market environment and why their role extends beyond just tax-free income.   Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.   Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠) Disclosure: This content, which contains security-related opinions and/or information, is provided for informational purposes only and should not be relied upon in any manner as professional advice, or an endorsement of any practices, products or services. There can be no guarantees or assurances that the views expressed here will be applicable for any particular facts or circumstances, and should not be relied upon in any manner. You should consult your own advisers as to legal, business, tax, and other related matters concerning any investment. The commentary in this “post” (including any related blog, podcasts, videos, and social media) reflects the personal opinions, viewpoints, and analyses of the Plancorp LLC employees providing such comments, and should not be regarded the views of Plancorp LLC. or its respective affiliates or as a description of advisory services provided by Plancorp LLC or performance returns of any Plancorp LLC client. References to any securities or digital assets, or performance data, are for illustrative purposes only and do not constitute an investment recommendation or offer to provide investment advisory services. Charts and graphs provided within are for informational purposes solely and should not be relied upon when making any investment decision. Past performance is not indicative of future results. The content speaks only as of the date indicated. Any projections, estimates, forecasts, targets, prospects, and/or opinions expressed in these materials are subject to change without notice and may differ or be contrary to opinions expressed by others. Please see disclosures here.
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Sep 3, 2025 • 36min

Can AI Keep Driving the Stock Market Higher? Callie Cox Explains (EP.220)

Join Callie Cox, Chief Market Strategist at Ritholtz Wealth Management, as she dives into the impact of AI on the stock market. She breaks down why Wall Street's AI optimism clashes with economic realities. Callie shares insights on how concentrated earnings growth in tech presents both opportunities and risks, and draws lessons from historical giants like GE. Discover which sectors beyond Big Tech might benefit from AI adoption and learn how to differentiate between hype and true innovation for long-term investing.
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Aug 27, 2025 • 27min

Mutual Funds vs ETFs vs SMAs: Which is the Best For You? (EP.219)

Discover the key differences between mutual funds, ETFs, and SMAs, including their impacts on taxes, costs, and control. Learn how ETFs and SMAs can offer solutions to the pitfalls of mutual funds. Delve into the concepts of tax-loss harvesting and how it creates tax alpha. Explore the future of investing as ETFs rise in popularity, SMAs gain traction, and mutual funds retain their role in retirement plans. This discussion is essential for anyone looking to refine their investment strategy.
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Aug 20, 2025 • 36min

How Evidence-Based Advice Adds Up to 3% In Net Returns With Fran Kinniry (EP.218)

Fran Kinniry, a senior investment executive at Vanguard and the mastermind behind the Advisor Alpha Study, shares invaluable insights about financial advising. He discusses the hidden costs that can erode portfolio returns and emphasizes the importance of after-tax wealth over mere pre-tax gains. Kinniry explains how advisors serve as 'behavioral circuit breakers' in volatile times. He also delves into the complexities of retirement income planning and why professional financial advice remains crucial for successful investing.
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Aug 13, 2025 • 37min

Reset Your Portfolio Expectations (Before It’s Too Late) (EP.217)

Jesse Cramer, host of The Best Interest Podcast, discusses key insights on investor behavior, volatility, and the importance of long-term planning. He emphasizes that market fluctuations are normal and shouldn't derail your strategy. Listeners learn to assess their portfolios during downturns and the value of global diversification. Cramer also highlights how emotional narratives can cloud financial decision-making, guiding investors to focus on substantive, long-term goals instead.
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Aug 6, 2025 • 40min

The Power of Humility in Investing with Dan Rasmussen (EP.216)

Get updates for my new book: https://Theperfectportfoliobook.com  -----  Dan Rasmussen, author of The Humble Investor, joins me to unpack the overlooked superpower of humility in investing. We discuss why market forecasts often go wrong, how overconfidence fuels financial mistakes, and where conventional wisdom can lead investors astray. Dan also reveals the hidden risks in popular private market strategies. Listen now and learn: ► Why humility can help investors navigate market volatility. ► The misunderstood truth behind value investing.  ► The risks investors overlook in emerging markets. ► What most people get wrong about private equity and private credit.   Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.   (02:46) Why We Misread the Future: Forecasting, Volatility, and the Illusion of Precision (09:06) How Humility Improves Investment Models and Decision-Making  (13:39) The Real Reason Value Investing Works—And When It Doesn’t (19:25) Why Value Investing Struggled in the U.S. But Not Abroad  (24:29) The Case for Geographic Diversification and Caution on Emerging Markets (30:46) The Risks of Overallocating to Private Equity  (36:14) The Danger Behind Private Credit’s Appeal   Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com) -----  Disclosure: This content, which contains security-related opinions and/or information, is provided for informational purposes only and should not be relied upon in any manner as professional advice, or an endorsement of any practices, products or services. There can be no guarantees or assurances that the views expressed here will be applicable for any particular facts or circumstances, and should not be relied upon in any manner. You should consult your own advisers as to legal, business, tax, and other related matters concerning any investment. The commentary in this “post” (including any related blog, podcasts, videos, and social media) reflects the personal opinions, viewpoints, and analyses of the Plancorp LLC employees providing such comments, and should not be regarded the views of Plancorp LLC. or its respective affiliates or as a description of advisory services provided by Plancorp LLC or performance returns of any Plancorp LLC client. References to any securities or digital assets, or performance data, are for illustrative purposes only and do not constitute an investment recommendation or offer to provide investment advisory services. Charts and graphs provided within are for informational purposes solely and should not be relied upon when making any investment decision. Past performance is not indicative of future results. The content speaks only as of the date indicated. Any projections, estimates, forecasts, targets, prospects, and/or opinions expressed in these materials are subject to change without notice and may differ or be contrary to opinions expressed by others. Please see disclosures here. Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).

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