Trapped By Taxes? How 351 Exchanges Let You Diversify Without Selling Your Stock (EP.225)
Release Date: 10/08/2025
Before You Add Alternatives: How to Tell if Private Markets Fit Within Your Plan (EP.231)
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. . ----- 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...
info_outline
Year-End Equity Comp Playbook With John Owens (EP.230)
The Long Term Investor
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. . ----- 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...
info_outline
Why Everyone Suddenly Loves Gold (and What Could Go Wrong) (EP.229)
The Long Term Investor
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 . ----- 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...
info_outline
Stop Keeping Score: Power & Fairness With Money Ft. Heather and Doug Boneparth (EP.228)
The Long Term Investor
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. . ------ 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...
info_outline
Should You Move to Cash When Markets Hit All-Time Highs? (EP.227)
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. . ----- Markets have hit record levels dozens of times this year, and the headlines are filled with uncertainty. It’s no wonder investors are asking whether now is the time to take some chips off the table. In this episode, I share what I told USA Today when they asked me the same question — and explain why new highs don’t necessarily mean markets are due for a fall. Listen now and learn: ► Why all-time highs are...
info_outline
From Numbers to Meaning When Building Your Retirement Plan with Carl Richards (EP.226)
The Long Term Investor
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...
info_outline
Trapped By Taxes? How 351 Exchanges Let You Diversify Without Selling Your Stock (EP.225)
The Long Term Investor
Wondering if you’re making the right financial moves? Let’s build a strategy you can rely on. 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...
info_outline
Year-End Tax Planning After the OBBBA (EP.224)
The Long Term Investor
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. . ----- 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...
info_outline
Bond Funds vs Individual Bonds: What’s Best for Your Portfolio? (EP.223)
The Long Term Investor
Wondering if you’re making the right financial moves? Let’s build a strategy you can rely on. 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...
info_outline
M&A, Valuations, and the Future of RIAs — A Conversation with Ian Wenik (EP.222)
The Long Term Investor
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. . ----- 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...
info_outlineWondering 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
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.