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Author and illustrator Carl Richards joins the show to discuss his new book Your Money and the real conversations we should be having about finances. If you've ever wondered how to stop worrying about money and start using it intentionally, this conversation will leave you thinking differently about every dollar you spend.

Listen now and learn:

► Why most people avoid the money conversations that matter most

► How to align your use of capital with what's genuinely important to you

► The power of micro actions and why small steps compound into lasting change.

► A simple mindset shift that can transform financial stress into confidence and clarity

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

(02:23) The Conversations We Avoid About Money

(04:16) Why Facts Don't Fix Feelings

(06:00) Simplifying on the Far Side of Complexity

(10:13) Aligning Your Use of Capital with What's Important

(14:31)Financial Planning Is About Being Less Wrong Tomorrow

(18:22) The Illusion of Certainty and the End of History

(23:55) The "Presenting Problem" and What Clients Really Value

(27:42) How to Start Better Money Conversations at Home

(35:36) Micro Actions: Tiny Habits That Compound

(38:59) The Worry List: Nothing Is Helped by Worry

(41:22) Practicing Gratitude and Redefining "Enough"

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.

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.

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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

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.

Your finances have layers—investments, taxes, planning for the future. If you want a second set of eyes, Peter opened up a few spots for a quick, no-obligation call. Grab yours now.

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Tax law shifts can change the best time to recognize income, give to charity, and make big business decisions. This episode unpacks how the "One Big Beautiful Bill Act (OBBBA)" reshapes year-end planning for pre-retirees, equity-comp executives, and business owners—and what still works vs. what to rethink. Listen now and learn: ► How the new charitable-deduction mechanics affect bunching and donor-advised funds ► What the updated SALT landscape means—and when a PTET election may still be worth it ► Where pre-retirees can find Roth-conversion "windows" and how NIIT thresholds influence capital-gain timing ► The big moves for owners and executives—from RSU withholding gaps and ISO/AMT credits to QBI and bonus-depreciation options

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

(03:08) OBBBA: What Actually Changed in 2025 (Rates, Estate & Gift) (05:29) Charitable Giving After OBBBA: 2% AGI Floor + Pease-Style Haircut (What It Means for DAF Timing) (7:42) SALT Deduction: $40k Cap With a Phase-Down for Higher Incomes (Plus PTET Strategy) (9:14) Social Security Isn't Tax-Free; New Senior Deduction Helps at Lower Incomes (10:11) Timing Still Wins: Why November Is the Last Best Window (and Why 2025 vs. 2026 Is Odd)

(12:33) Pre-Retirees: NQDC Spikes, Roth-Conversion Windows, and Capital-Gains/NIIT Coordination (17:31) Equity Compensation: RSU Withholding Gaps, Concentration Risk, and ISO/AMT Credits (21:34) Business Owners: QBI Permanence, 100% Bonus Depreciation, and Smoother Elections

(24:15) PTET: Powerful, But Don't Miss the Payment Deadline (26:05) Often Missed: SEP IRA for Self-Employed Income and Director Fees (27:00) How a Tax-Led Engagement Works (and Why Advisory + Tax Prep Reduces Errors)

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.

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.

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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.

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.

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.

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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

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.

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.

Get updates for my new book: https://Theperfectportfoliobook.com

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AI has fueled massive gains for Big Tech, but can one sector really carry the market forever?

In this episode, I'm joined by Callie Cox, Chief Market Strategist at Ritholtz Wealth Management, to explore the tension between Wall Street's AI-fueled optimism and the realities of a slowing economy. We discuss what history teaches us about dominant companies, how to spot the difference between hype and durable innovation, and what long-term investors should really be watching.

Listen now and learn:

► Why "the stock market is not the economy" — and why that matters in today's AI-driven rally.

► How concentrated earnings growth in tech creates both opportunity and risk.

► What history (GE, dot-coms) tells us about the limits of dominant companies.

► Which sectors beyond Big Tech could quietly benefit from AI adoption.

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

(02:22) AI optimism vs. a shaky economic backdrop (05:59) Can tech alone carry market earnings growth? (09:37) Dreaming vs. reality in AI investing (15:36) Lessons from GE and what they mean for Big Tech (19:29) Who really benefits from AI adoption? (21:53) The risks of concentration in the Magnificent 7 (24:51) Balancing story vs. evidence as a long-term investor (29:15) Early signs of real AI adoption and productivity gains (32:04) Everyday use cases of AI in real life

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.

Check out the best podcast show notes on the internet at www.thelongterminvestor.com

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Mutual funds, ETFs, and SMAs all give you access to the market — but the way they handle taxes, costs, and control can lead to very different outcomes. In this episode, I break down how each vehicle works, where it shines, and when it falls short. If you've ever wondered which is best for your portfolio, this is the episode you'll want to hear.

Listen now and learn:

► Why mutual funds can leave you paying for other investors' decisions — and how ETFs and SMAs solve that problem.

► The key differences between mutual funds, ETFs, and SMAs in terms of tax efficiency, cost, and customization.

► When an SMA makes sense (and when it doesn't) — including how tax-loss harvesting at the stock level creates "tax alpha."

► The future of investing vehicles: why ETFs dominate flows, how SMAs are growing, and why mutual funds still matter in retirement plans.

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.

Not all financial advisors are created equal. Before you hire one, make sure you're asking the right questions. Use my structured interview worksheet to compare advisors and avoid costly mistakes. Get it free.

Vanguard's Advisor's Alpha framework just turned 25—and few people know its impact better than Fran Kinniry, the study's original architect. In this episode, we explore how Advisor's Alpha reshaped the value of financial advice, why its lessons are more relevant than ever, and what it means for investors today.

Listen now and learn:

► The hidden costs that quietly erode portfolio returns

► Why after-tax wealth matters more than pre-tax gains

► How advisors act as "behavioral circuit breakers" in volatile markets

► The overlooked complexity of turning a portfolio into retirement income

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

(02:30) The Origins of Advisor's Alpha

(05:00) Three Transformative Shifts in Financial Advice

(15:00) Investment Selection and Market Cap Awareness

(22:00) The Complexity of Retirement Income Planning

(26:00) Total Return vs. Income-Only Investing

(29:00) Why Professional Financial Advice Still Matters

(33:00) Closing Thoughts

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.

Get updates for my new book: https://Theperfectportfoliobook.com

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Recently, I joined Jesse Cramer on The Best Interest Podcast for a conversation on volatility, investor behavior, and how to avoid overreacting to headlines. We unpack why market noise can distort long-term plans and what to do when your risk tolerance feels misaligned with your portfolio.

Listen now to learn:

► Why volatility is a feature—not a bug—of long-term investing ► What to do if market drops reveal your portfolio isn't right for you ► How global diversification helps even when it feels like a drag ► How narratives—not just numbers—drive poor investing decisions

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

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).