Episodes

Tom takes a break from vacationing to join Don in a deep dive on target date funds—the good, the mediocre, and the fee-loaded ugly. They break down performance data, highlight major fund differences, and remind listeners why understanding your own risk tolerance still matters. Listener questions spark advice on Roth IRAs for young investors and strategies for holding large tax payments. All with classic banter, bad jokes, and a quick jab at the Raiders. 0:04 Tom’s back (briefly), and the banter...

In this lighter (but still info-packed) Friday Q&A episode, Don tackles a mixed bag of real-world money questions—from Roth conversions and selling the family home to foreign tax credits and the emotional overload of trying to do everythingat once. Listeners wrestle with software vs. strategy, gifting real estate to their kids, and finding financial sanity in mid-life. Don reminds us: good advice doesn’t come with a magic wand, but it does come with a bit of permission to slow down. 0:56 Roth c...

Don shares a deeply personal tale from 2007 when, as an HOA treasurer, he dodged a financial landmine involving auction-rate securities—just before the 2008 crisis froze their liquidity. That real-life scare flows into a fierce takedown of today’s institutional obsession with illiquid assets like private equity, especially in university endowments. Harvard’s high-risk strategies, retirement plans promoting alternatives, and the seductive myths of market outperformance get picked apart. Don and T...

Tom and Don open the show with tech woes and quips before diving into a serious discussion about the U.S. credit rating downgrade and its implications for borrowing costs and long-term debt. They offer practical investing advice in light of the downgrade—think short- and intermediate-term bonds and global diversification. Listener calls bring a colorful array of financial situations: a comfortably retired couple managing rental income, a military retiree with credit card debt, a candid debt hist...

Don returns from a exhausting, comedy-of-errors flight to discuss how the markets pulled an equally wild round trip—plunging, then rebounding to the tune of $8 trillion. He and Tom break down the April stock and bond tantrum, laugh off predictions of recession, and offer practical guidance for scared investors, risk-takers, and those tempted by annuities. Listener questions cover mortgages vs. investing, the role of fixed annuities, and a touching thank-you from a longtime fan who retired well t...

Don and Tom welcome Weston Wellington of Dimensional Funds for a rare and richly insightful conversation covering market volatility, media noise, diversification, and the enduring wisdom of index investing. Weston compares Spam to Motorola, skewers financial hype, and champions simplicity in investing—and yes, he might just sing if you let him. The conversation explores how far the financial industry has evolved (and still has to go), why most investors get in their own way, and whether AI or ju...

Don’s back from NYC with pride (and maybe jet lag), tackling a full slate of thoughtful listener questions. From Roth conversions and the TSP G Fund to cash balance plan gimmicks, RMD timing, overpriced 401(k) plans, and yes, the eternal question: Are annuities ever worth it? Don delivers straight talk, a little outrage, and no-nonsense advice—with some well-placed jabs at the industry’s smoke and mirrors. 0:04 Don returns from NYU graduation trip and thanks listeners for sending questions0:56 ...

Don and Tom launch into a globe-trotting episode—complete with multilingual greetings and a cameo from Cookie Monster—before diving into the serious question of global investing. They challenge the "home country bias" that keeps investors overly concentrated in U.S. stocks, highlight the recent performance gap favoring international small-cap value, and remind listeners that chasing returns and market timing are just two sides of the same bad investing coin. With personal anecdotes, Japan’s long...

In this episode, Don and Tom rewind to the not-so-golden era of Wall Street paperwork, bringing a modern perspective to old-school investing habits. They tackle listener questions around dividend investing, the allure of individual stocks, and whether the 'buy and hold forever' mindset still holds up in the era of ETFs. Along the way, they dismantle outdated advice, give historical context to stock certificate culture, and steer listeners back toward diversified, evidence-based strategies. A lit...

Don and Tom take aim at America's favorite financial myths—starting with the widespread belief that real estate and gold are the best long-term investments. They present nearly 100 years of historical data to show why stocks have far outpaced both. The conversation also tackles misleading annuity pitches, a classic pension lump sum dilemma, and the age-old question facing 20-somethings: save for a house or retirement? Callers bring smart questions about guaranteed annuities, where to park sur...

In this episode, Don and Tom tackle the investor's most persistent foe—fear—especially during volatile markets. They draw on insights from Vanguard and others to reinforce the value of long-term investing, explain why missing a few key days in the market can devastate returns, and stress the importance of rebalancing over reacting. The duo also takes on political distractions, market timing myths, asset location dilemmas, and the emotional turbulence that causes people (including Don’s wife!)...

In this extra-packed Friday Q&A episode, Don powers through a barrage of listener questions while recovering from an attempted heart ablation (yep, he's okay—but not fixed). He dives into everything from sketchy SIMPLE IRA fees and Roth rollover rules, to when it actually makes sense to take Social Security. You’ll also hear a checklist of questions to grill a potential financial advisor with, a primer on small-cap value stocks, and a lightning-round suggestion for international bond exposure. A...

On this Talking Real Money episode, Don and Tom tag-team one of the biggest financial myths around: your house as a retirement plan. With over $35 trillion locked in U.S. home equity, they challenge the idea that owning a home equals wealth. From the emotional pull of mortgage payoffs to the liquidity traps of reverse mortgages and HELOCs, the duo breaks down the risks, rewards, and real returns of homeownership. Then it’s on to listener questions about IRAs, 401(k)s, rollovers, and... fiber (ye...

Tom and Roxy Butner to co-host a packed episode of Talking Real Money, tackling the ever-elusive "magic number" for retirement with a healthy dose of realism, humor, and data. They dig into a Northwestern Mutual study that shows Americans lowering their retirement savings goals—even as confidence continues to slip. Roxy breaks down why retirement planning is all about cash flow, not some mythical lump sum. They field questions on company stock in 401(k)s, bonus check strategies, RMD tax ...

Tom Cock takes the mic solo (with Don recovering from a “procedure”) and brings in advisor Roxy Butner for a special live episode. They reflect on Warren Buffett’s decision to retire in 2025, discussing lessons from his value investing strategy and massive cash holdings. Listener questions roll in on topics like compound interest assumptions, the risks of holding company stock, ETF mechanics, and how best to diversify for retirement. They also recommend the YouTube documentary Tune Out the Noise...

Don and Tom get real about the most important lessons every young person should learn about money—before life (and bad decisions) get in the way. From money values to compound interest, tax realities to the unpredictability of markets, they each offer a list of financial truths no teen should graduate without. Along the way, they drop stories from their own lives, take questions from listeners, and somehow end up discussing soccer (and why Don still doesn’t get it). 0:04 Back to basics: What yo...

Don records this Q&A episode a bit early—right before heart surgery—to make sure listeners don’t miss their Friday dose. He kicks off with a listener confused by a boilerplate $50 foreign stock fee warning on a Fidelity Zero fund (spoiler: it doesn’t apply). Another caller is teetering on the edge of retirement viability with $500K, pensions, and Social Security—Don offers honest thoughts on withdrawal flexibility and why waiting on SSI might be wise. Then comes a takedown of Wealthfront’s direc...

On this myth-busting episode of Talking Real Money, Don and Tom tackle persistent financial fables that sound logical but often lead investors astray. With help from a Kiplinger list and their own experience, they dissect myths around mortgage payoff returns, Roth conversions, Social Security fears, withdrawal rules, and tax refunds—plus three bonus myths that still haunt conversations today. Along the way, Don shares his own recent experience filing for Social Security online (spoiler: it was s...

Tariffs, fear, and stockpiling—oh my! Don and Tom break down how consumer sentiment, not just consumer spending, is shifting dramatically under the weight of tariff uncertainty. They connect behavioral shifts—like Googling “recession” and panic-buying tires—to bigger economic signals and what it all means for investors. From the role of emergency savings to the misleading pitch of indexed annuities, they dismantle hype and stress the importance of sticking to a real plan. They also field smart q...

Our memories—and sometimes our parents'—shape how we invest, often more than logic or data. Don and Tom break down how generational financial trauma, recent market trends, and asset class myths (like gold and U.S.-only investing) skew our thinking. They call out flawed stock picking contests, revisit the real long-term returns on gold versus stocks, and explain why short-term memory leads to bad long-term decisions. Listener questions hit everything from where to park house savings to bond fu...

Don and Tom dive into the seductive but dangerous world of leverage, starting with real estate and quickly moving into the even riskier territory of leveraged ETFs. They explain how leverage magnifies both gains and devastating losses, using real-world examples like the Direction 3X Treasury Bull and Bear funds, which either crushed or annihilated investor money. They caution listeners that these “extra touchy” funds are pure speculation, not investing, and explain why most people should stay fa...

In this listener Q&A episode, Don dives into some powerful topics—from calling out the sales-driven heart of the financial services industry to explaining how bond index funds are built and breaking down the tax realities of non-retirement brokerage accounts. A caller wrestles with guilt over a bad annuity recommendation for a dying relative, prompting a raw conversation about the system’s moral middle ground. Don shares his own early days as a product peddler, highlights red flags to look for i...

Gold is back in the headlines, but should it be in your portfolio? Don and Tom take a fresh (and frequently hilarious) look at the shiny metal that never seems to deliver. From Fort Knox to Costco’s gold bar rush, they trace gold’s lackluster long-term returns and its overhyped reputation as a hedge. They break down why physical gold fails as an investment, why GLD is better (but still meh), and why long-term investors might already have enough exposure through diversified funds. Plus: a Medicar...

When markets get bumpy, emotions take the wheel—and that’s exactly why Don spends this solo episode reminding listeners that logic, evidence, and simplicity still win in the long run. He digs into why private investments aren't the magic they claim to be (even when Vanguard jumps in), why diversification still beats sexy strategies, and how the best “alternative” to bad investing is simply building a solid plan and sticking to it. Listener calls explore structured products, the Sharpe ratio, rev...