Talking Real Money - Investing Talk

The best portfolio cannot help much if every spare dollar disappears at checkout. Don and Tom debate practical ways to slow impulse purchases, automate saving, and build better money habits—without banning the things that make life enjoyable. A live listener call turns to TIAA and 403(b) costs, diversification, and where stocks and bonds belong across Roth and traditional accounts. Then they discuss why a pension promise depe...

Who is looking out for insurance customers—and who is paying the people who set the standards? Don and Tom examine insurance-industry incentives, questions about the NAIC’s funding and transparency, and why consumers should ask about commissions and costs. Then a listener challenges their take on rising equity glide paths and sequence-of-returns risk. They revisit the competing research and the role of personal risk tol...

Target-date funds promise a simple glide path from growth to safety—but people with the same retirement date can have completely different needs. Don and Tom compare Vanguard, Fidelity, and BlackRock funds, examine costs and stock-bond mixes, and explain why simple does not mean specific. Then they revisit decades of failed crash predictions from Rich Dad, Poor Dad author Robert Kiyosaki.

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Should retirement spending pass through a Roth? Can a nonprofit offer a 401(k) with ETFs? Does active management really win overseas? Don works through a packed listener-question episode covering Roth conversions, retirement-plan rollovers, SPIVA versus Morningstar, Treasuries and CDs, dividend reinvestment in retirement, and whether a variable universal life policy still earns its keep.

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A CFP mark reflects meaningful education, but it does not guarantee clean disciplinary history, fee-only advice, or an unwavering fiduciary relationship. Don and Tom examine the gap between reassuring credentials and the disclosures investors may find through FINRA BrokerCheck and SEC adviser records.

They explain what investors should verify before hiring anyone: compensation, dual registration, product sales, disclosures, ...

An 11.15% coupon sounds irresistible—until you read the trapdoors. Don and Tom unpack a listener’s BNP Paribas auto-callable structured note and ask the question Wall Street hopes nobody asks: what actually has to happen before you get paid?

The answer includes contingent coupons, the worst-performing of three indexes, a five-year lockup, bank credit risk, and a cliff where a 41% market loss can become your 41% l...

Dimensional Fund Advisors founder David Booth joins Don and Tom to explain why better investing begins with accepting uncertainty instead of pretending to predict it. They discuss staying calm through frightening markets, controlling what investors can control, and why missing a rebound can permanently damage a plan.

Booth also traces the evidence behind factor investing—market, size, value, and profitability—and...

Risk and reward are inseparable, even when an investment pitch makes the danger hard to see. Don and Tom explain why higher expected returns require accepting uncertainty, why recent gains do not erase future losses, and why products promising market-like returns without market risk deserve skepticism.

Then they answer listener questions about market odds, taxes, Chime, and finding truly fiduciary advice.

Questions? Comments?...

It’s Friday Q&A—with a small experiment. Don slips one AI-generated voice among the listener questions and challenges you to identify the robot, with his complete two-book library hanging in the balance.

The financial questions are thoroughly human: where to keep a future car fund, whether an $11,000 Roth-conversion program earns its fee, when children can fund Roth IRAs, and what happens when bond holdings m...

Robinhood says it wants to be everything to investors—but its fastest-growing attractions look a lot like a casino. Don and Tom examine prediction markets, options, crypto, payment for order flow, and the uneasy fit between fiduciary advice and a brightly lit door to speculation.

They explain why gamification and enormous transfer bonuses can be especially dangerous for inexperienced investors. If the goal is long-term...

The market’s long winning streak has investors wondering whether a crash is waiting in the wings. Don and Tom look at the S&P 500’s run, the lost decade that followed the 1990s boom, and why international diversification changed that outcome dramatically.

They also explain why market timing asks the impossible: missing the worst days sounds wonderful, but missing the best days can be devastating. The less the...

Wall Street has declared yet another “year of the stock picker.” Don and Tom examine Morningstar and SPIVA data showing how few active large-cap funds beat their benchmarks—and why high fees, trading costs, taxes, short horizons, and fierce competition keep the odds tilted toward low-cost diversification.

Then Greg asks where stocks and bonds belong while he begins Roth conversions. The discussion covers as...

Rule Seven of Financial Physics says there is no new news: by the time public information reaches you, the market has already reacted.

Don and Tom explain why neither headlines nor illegal insider tips offer ordinary investors a durable edge, why fast trading and miracle systems disappoint, and why accepting market returns is the saner path.

Then they compare JAAA with BND, help a student balance FAFSA concerns with e...

Friday’s question pile ranges from the safest bond fund around to the harder question of what retirement is actually for. Don sorts through the choices with his usual preference for simple, sturdy answers.

He weighs the TSP G Fund against BND, checks the bona fides of Raisin and The College Investor, and argues that leaving work makes sense only when something better is waiting on the other side.

Then comes a ca...

Being great at running a company does not make anyone a market oracle. Don and Tom unpack the money regrets of successful CEOs—and the costly confidence that often follows success.

They draw the line between business skill and investment skill, explain why financial literacy matters, and make the case for diversification over hindsight, stock-picking games, and concentrated bets.

Then they turn to listener quest...

Could a nation of steadier 401(k) investors make markets calmer—or will algorithms, options, and meme-stock behavior keep the ride bumpy? Tom and Roxy weigh the forces pulling volatility in both directions.

Next, an almost-80-year-old with a $4 million portfolio asks who should coordinate the inheritance plan. The answer is a team effort, with the financial advisor calling the plays and the CPA and estate attorney hand...

AI’s appetite for data centers is sending tech giants to the bond market—and some of that debt will still be around in 2075. Don and Tom look at the scale of the borrowing and why a tempting yield deserves a closer look.

They separate coupon rate from yield to maturity, explain senior unsecured debt, and show how brutally interest-rate-sensitive a 50-year bond can be. The verdict: these bonds may belong in a broa...

Why is financial forecasting so persuasive when its track record is so poor? Don and Tom open the Book of Financial Physics to Law No. 6—“Nobody Knows Nothing”—and explain why stock pickers, market timers, and highly paid pundits cannot reliably tell you what comes next.

Then they answer listener questions about permanent life insurance and deferred income annuities, trusted contacts and two-factor au...

Required minimum distributions don’t have to trigger a fire sale. Don explains how an in-kind transfer can move an investment from an IRA to a brokerage account while preserving the holding and resetting its cost basis.

Then it’s back to school: a cut-off Coverdell question, the unusual strength of the TSP G Fund, and a surprisingly useful 4% money market account that can behave a lot like checking.

The fi...