Talking Real Money - Investing Talk

Roxy Butner joins the show to break down practical retirement saving strategies—especially for entrepreneurs who struggle to pay themselves first. The conversation covers foundational options like IRAs and Roth IRAs, then moves into more powerful tools such as Solo 401(k)s, SEP IRAs, and SIMPLE IRAs for business owners. They highlight the enormous impact of starting early through compounding, common planning mistakes (like neglecti...

Don and Tom tackle the idea that retirement isn’t what it used to be—and maybe shouldn’t be at all. From historical retirement ages (when most people never made it) to today’s longer, healthier lives, they explore why many people aren’t eager to stop working. The conversation shifts to purpose, identity, and the growing trend of “phased retirement,” where people scale back instead of quitting outright. They also answer listener que...

A wide-ranging Q&A episode tackles the real-world tradeoffs investors actually face: whether Paul Merriman’s aggressive small/value “ultimate” portfolio is worth the complexity and risk, how much stock to put in scary online bank reviews versus FDIC reality, and how to find advice when you don’t want someone managing your money. Don also explains why FAFSA tricks with traditional IRA contributions don’t work, how to control cap...

Annuities promise peace of mind—but often at a steep and poorly understood cost. Don and Tom break down when (rarely) annuities might make sense, why most—including fixed indexed annuities and QLACs—tilt heavily in favor of the insurance company, and how investors can replicate “guaranteed income” with a disciplined portfolio instead. They also take on a listener question about escaping high fees at Edward Jones (spoiler: yes, run)...

Starting early beats almost everything else in investing—and this episode drives that home with eye-opening math and a brand-new tool for jumpstarting a kid’s retirement. Don and Tom break down the new “Youth Retirement Account” concept (government seed money plus family contributions), compare it to Roth IRAs and 529 rollovers, and show how relatively modest early contributions can grow into millions. Then they pivot to a listener...

This episode exposes the misleading language behind “best interest” financial sales practices, using the insurance-backed fight against the Department of Labor’s fiduciary rule as the main example. Don and Tom explain why rolling money from a 401(k) or 403(b) into an IRA can leave investors vulnerable to commissions, conflicts, vague disclosures, and expensive products dressed up as advice. They break down the difference between tr...

A century-long study by Hendrik Bessembinder reveals a stunning truth about investing: while the U.S. stock market produced enormous overall wealth, the vast majority of individual stocks were losers, with just 46 companies responsible for half of all gains. Don and Tom unpack what this means for investors—namely, that stock picking is essentially a losing game driven more by luck than skill, and that broad diversification through ...

This Friday Q&A episode of Talking Real Money features a surge in listener questions, covering key retirement and investing topics including IRA inheritance strategies, borrowing in retirement, how to find fiduciary advisors, the powerful tax advantages of HSAs, pension timing decisions, and whether Robinhood’s 2% IRA transfer bonus is worth the trade-offs. Don emphasizes simplicity and tax efficiency—favoring IRA rollovers ove...

Don and Tom tear into Kiplinger’s roundup of “best money advice,” separating the genuinely useful from the obvious, the flawed, and the downright silly. They agree that core principles like living below your means, automating investing, and seeking qualified fiduciary advice still reign supreme, while pushing back on oversimplified takes about debt, life decisions, and self-auditing. The conversation reinforces a familiar truth: pe...

This episode cuts through the marketing fog around “financial advisors,” breaking them into three real categories—brokers, insurance agents, and fiduciary investment advisors—and exposing how incentives, commissions, and murky regulations shape the advice investors receive. Don and Tom highlight the industry’s gradual shift away from commissions while warning that titles like “fiduciary” or “CFP” don’t guarantee behavior. A listene...

Don and Tom kick things off with a colorful history lesson on 19th-century “bucket shops,” drawing a sharp parallel to today’s emerging world of tokenized securities—digital representations of stocks traded on blockchain platforms. While proponents tout 24/7 trading and faster settlement, the hosts question the real value, highlighting added complexity, thin trading, pricing deviations, and unclear ownership structures. They frame ...

This episode shifts from investing to the growing threat of scams—especially targeting older adults—breaking down how common fraud tactics work, from fake virus alerts and spoofed calls to AI-driven voice cloning and recovery scams. Don and Tom emphasize a simple but powerful rule: if you didn’t initiate the contact, assume it’s a scam, and never act under pressure. The conversation then pivots to listener questions, covering how t...

This Q&A episode tackles a mix of practical retirement and investing questions, starting with why spousal Social Security benefits rarely change the core advice to delay claiming. Don explains the limits of basic retirement calculators versus more robust planning tools, then reassures a late-starting saver that simple, low-cost investing (like target-date funds) often beats complexity. A listener’s story about $242 stock commis...