The Long Term Investor

Get an inside look at what's shaping my thinking. Bi-weekly, I share the top 5 investing and financial planning articles I'm reading—straight to your inbox. Sign up for my newsletter. ----- In this rebroadcast, Peter sits in the guest chair to explain why he rarely recommends private markets—and the specific situations where they do belong. He lays out a clear filter built around liquidity, purpose, access, and behavior so you can decide whether private investments fit in your plan. Listen now and learn: ► A simple decision framework for alternative investments ► Why Peter is more concerned with implementing a bad idea than missing out on a good one ► What makes venture capital investing hard for most investors ► The implications of more "democratized" alternative investment products 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.

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. ----- Equity compensation can turbocharge wealth—and taxes. Brooklyn Fi managing partner John Owens joins Peter to share a clear year-end playbook for RSUs, ISOs/NQSOs, and ESPPs, including how to avoid AMT surprises, right-size withholding, and unwind concentrated stock positions. Listen now and learn: ► A simple order of operations for year-end equity comp decisions ► RSU withholding pitfalls (and how to fix them before April) ► ISO/AMT basics and why late-year exercises can backfire ► How to build a rules-based plan, use 10b5-1 mechanics, and when donor-advised funds make sense Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions. (00:00) Introduction (03:15) A hard-won lesson: when AMT grows larger than your stock (and what to do next) (04:21) Don't start equity planning on December 15 (really) (05:19) First move: build an inventory and triage the quick wins (08:18) AMT 101 for ISO holders: the "parallel" tax you don't want to pay (10:47) RSUs: why 22% withholding often sets up an April tax bill (12:24) ESPPs: capture the discount, control concentration (14:55) Designing a rules-based sell plan to unwind concentration risk (18:11) The base rates on single stocks: why a diversification plan matters more than a "feel" (20:42) 10b5-1 plans: automate good behavior and expand your ability to sell (23:31) Charitable giving with concentrated stock: donor-advised funds and timing across 2025/2026 (26:11) Family gifting: UTMAs, kiddie tax, step-up in basis, and multi-generational choice (27:28) The year-end document checklist most people miss (29:17) When to hire help (and when not to) (31:19) Biggest year-end mistakes to avoid 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.

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. ----- Gold just cleared $4,000 an ounce while stocks hover near highs—a rare split-screen of optimism and caution. In this episode, I break down what's actually pushing gold up, stress-test its "safe haven" reputation, and evaluate whether it truly protects against inflation. We'll finish with a simple, rules-based way to decide if gold deserves a small place in a long-term portfolio—or none at all. Key takeaways: ► What's driving gold now: the role of central-bank buying, macro uncertainty, interest rates, and the dollar. ► Why "safe haven" isn't a free pass: what history says about mean reversion, drawdowns, and volatility. ► Inflation reality check: how stocks and real estate have delivered positive real returns when inflation is >4%—and why gold hasn't—plus when TIPS are the right hedge for specific future expenses. ► A practical allocation framework: when 0%, a small sleeve, or a strict 0–5% target makes sense—and how to set rebalancing rules so you can stick with the plan. 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.

Most financial mistakes happen because people don't see the full picture. My Net Worth Worksheet helps you track everything in one place—so you stay informed. Get it now. ------ Money talks fall apart when couples keep score. In this episode, Heather and Doug Boneparth show how fairness—not 50/50—actually works in real life, and how power shows up through invisible labor, access, and decision rights. You'll hear practical ways to reset the dynamic so conversations feel collaborative instead of adversarial. Listen now and learn: ► A fairness framework to replace 50/50 splits and tit-for-tat bean counting ► How to surface invisible labor and shift from "tell me what to do" to true task ownership ► The anatomy of a money date (time/place, start with wins, then goals → cash flow → net worth) ► Reconciling different risk appetites by agreeing on shared capacity, timelines, and one step outside each comfort zone Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions. (00:00) Introduction (02:45) Fairness vs. Equality in Couples' Finances (11:24) Resentment Red Flags in Relationships (13:47) Invisible Labor to Task Ownership (18:26) Financial Transparency for Couples (21:49) Money Dates That Don't Derail (26:48) Different Risk Tolerances in a Relationship (31:00) Co-Authoring Money Together (33:32) Lightning Round for Couples 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.

Navigating record market highs can be tricky. All-time highs are normal and shouldn't trigger panic. Behavioral traps often lure investors into the cash-out mindset. Strong earnings and fundamentals are buoying valuations. Is the hype around AI creating a market bubble? Timing the market is risky—getting it right once is challenging enough, let alone twice. Instead of rushing to cash, reassessing portfolios and allocations is crucial. Stay disciplined and focused on long-term strategies.

Please rate and review The Long-Term investor in your favorite podcast app. ----- 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" 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.

Investors worried about tax implications from selling appreciated stocks can find relief through Section 351 exchanges. This strategy allows the exchange of concentrated stock for ETF shares without immediate tax consequences. Peter Lazaroff discusses eligibility criteria, the non-recognition nature of the exchange, and practical benefits compared to traditional strategies. He highlights why these exchanges are gaining popularity due to advancements in technology and offers insights into key questions to discuss with financial advisors. It's a smart and efficient way to diversify.

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!

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.

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.