2025 was a stellar year for investors—but will the same playbook work in 2026?

In this episode of Payne Points of Wealth, Ryan Payne, Bob, Chris, and special guest Aaron Dessen kick off the new year by reflecting on an unexpected, across‑the‑board winning year in markets—and then pivot to what really matters now: what could derail your portfolio in 2026.

The team breaks down 5 key hurdles investors must watch in the coming year, including geopolitical shocks, Fed rate cuts, the dangers of sitting in cash, speculative “casino‑like” market behavior, and the growing risk of chasing last year’s returns. From surprise upside volatility during global conflicts to why money markets are not a long‑term solution, this episode challenges many of today’s popular investing assumptions.

You’ll also hear a candid discussion on:

• Why no one—not even experts—can reliably predict markets
• The hidden risks of FOMO in late‑stage bull markets
• Whether gold, silver, and commodities still belong in portfolios after a big run
• The difference between investing and speculating in leveraged ETFs and momentum trades
• Why diversification and discipline matter more than ever in hot economic conditions

In the second half of the show, the team performs a real‑world Financial Autopsy, analyzing the portfolio of a retired couple in their late 70s. Aaron walks through how excessive equity exposure, high‑fee mutual funds, and poor tax efficiency put retirees at serious risk—despite “good performance” on paper. The group highlights how reallocating toward income, reducing downside risk, and aligning investments with actual retirement goals can dramatically improve peace of mind.

This episode is a powerful reminder that:

Bull markets reward confidence—but they also hide risk.

Whether you’re approaching retirement, already retired, or just wondering how to position your portfolio for an unpredictable 2026, Episode 228 delivers timely perspective, practical insights, and a healthy dose of market realism.

Don’t miss this essential start‑to‑the‑year conversation.

Markets are printing fresh highs, yet some investors are getting crushed—how does that happen? In this roundtable, Ryan Payne, Bob Payne, Courtney Garcia, and Frankie Lagrotteria break down a real case of a couple in their late 50s whose “do‑anything‑to-go-faster” portfolio relied on leverage and crowd‑favorite names…right as they approach full retirement. We dissect why speculation masquerading as strategy can implode even in up markets, why “know what you own and why you own it” matters more than ever, and how to rebuild a plan centered on durable income and disciplined risk management.

You’ll hear why the “Ozempic portfolio” analogy fits—everyone wants the quick fix—but lasting wealth still requires basics: diversified exposure, sensible cash flow, and rules that keep emotions out of the driver’s seat. We also cover today’s opportunities to generate income (value, small caps, international, REITs, and bonds at still‑elevated yields), our 5% rebalance discipline, and the investor psychology traps that move the goalposts until a margin call makes the decision for you. As Bob puts it: time passes, markets operate—embrace that principle, and you’ll stop chasing the cool kids and start compounding with the rich ones.

What we cover:

• Why leverage is a “rocket booster” on both gains and losses—and how portfolios can sink while indexes rise
• The danger of fashion FOMO: copying friends, gym talk, or headlines instead of a plan
• Income blindness: several million invested but only ~$4K/year in cash flow—why that’s a retirement red flag
• Today’s income playbook: value, small caps, international, REITs, and bonds (with yields still attractive)
• Discipline over drama: our 5% rebalance trigger and rules that keep feelings from running your money
• Investor psychology: goalpost‑moving, “being right twice” in speculation, and volatility as the fee for long‑term returns
• Practical steps to audit and de‑risk before retirement

Key takeaways:

• Know what you own and why. Double‑levered bets can fall even when the market is up—understand the mechanics before you buy.
• Build real cash flow. Retirement works best when your portfolio pays you, so diversify toward durable income sources.
• Write your rules. Pre‑commit to rebalance triggers, position limits, and exit criteria to avoid emotional decisions.
• Approximately right beats precisely wrong. You don’t need to predict the next macro move; you need a plan you can stick to.

Calls to action:

• If you’re within 5–10 years of retirement, run a leverage and income audit on your portfolio.
• Want help building a rules‑based, income‑focused plan? Schedule a consult with the Payne Capital team and let’s put discipline to work: paynecm.com/financialplan/

— Enjoying the show? Follow, rate, and review Payne Points of Wealth on Apple Podcasts and Spotify and share this episode with a friend who’s chasing “quick wins” instead of compounding.

In this episode of Payne Points of Wealth, we sit down with Songe LaRon, a dynamic New York City tech entrepreneur, Co-Founder and CEO of SQUIRE Technologies—the world’s leading all-in-one barbershop business management system. Songe shares his remarkable journey from growing up in Manhattan with artist parents, to earning a J.D. from Yale, practicing law at a top firm, and ultimately making the leap from a more certain future in corporate America to launch a tech company that’s transforming an entire industry.

We explore how his upbringing shaped his relationship with money, the entrepreneurial spark that led to founding SQUIRE in 2015, and the challenges of breaking into tech without a technical background. Songe reveals how he and his team scaled SQUIRE to serve over 32,000 professionals across three continents, raised nearly $150M in funding, and built a culture of innovation that now integrates AI to revolutionize barbershop operations.

This episode is packed with insights on funding a startup, lessons from running an actual barbershop, personal wealth philosophies, and the mindset required to turn an idea into an industry leader. Plus, Songe shares his thoughts on the future of AI in business and the importance of resilience in entrepreneurship.