Jillian Johnsrud: 'Why retire once when you can retire often?'

   — Ravi Wadan, the founder of DriveMatch.com, discusses pre-negotiated car leases and the benefits of leasing online.    — Nik Johnson of EverydayMoneyHeroes.com, who talks about overcoming the challenges that keep many families from building generational wealth, and how it is small daily moves or changes have impacts that can last for decades on families.    — Gwen Merz Joiner, the original "fiery millennial," who aggressively scrimped and saved in her 20s to "retire early," only to find herself miserable. The co-host of the FIRE Takes podcast, changed her lifestyle, found happiness and a job she loves, but who is now turning 35 and looking at using the financial groundwork she laid as a cornerstone to answering the question "What's next?"    — Adam Bergman, founder of IRA Financial, who discusses how investors have been using alternative assets from cryptocurrency to real estate to private equity in self-directed IRAs, but who will now find access to those asset classes in their 401(k) plans thanks to recent law changes. He discusses how retirement portfolios have changed as those assets have become more available.    — Plus, Fridays on Money Life start with "The NAVigator," and today John Cole Scott, president of CEF Advisors, sizes up[ the times when an investor might pick (or mix-and-match) owning a closed-end fund versus an ETF or a fund-of-funds that covers the same asset class.

Money Life begins the first of three days of interviews from FinCon 2025, the annual gathering of financial content creators, which this year is in Portland, Ore., and which lets Chuck showcase a wide range of subjects. Today, those subjects include:  — college savings and the changing landscape of consumers paying off college debt with Robert Farrington of TheCollegeInvestor.com.  — crushing medical debt, and an unusual way for consumers to get out from under it with Jared Walker, founder of the non-profit fintech start up Dollar For. — a conversation that Chuck thinks may be the most unusual of his long career with comedian turned financial coach Lauren Baker, who also goes by the    name "Firenze, the friendly FIndom" and whose interview will introduce you to the world of financial domination. — "How Financial Stuff Works," the long-hoped for literacy project of financial adviser Alex Whitehouse. — the changing state of financial content creators, what's dead, what's next and how artificial intelligence will impact it all with FinCon's founder, Philip Taylor of TheCreatorCPA.com. Plus, every Thursday on Money Life starts with the ETF of the Week, and Todd Rosenbluth, head of research at VettaFi, makes a multi-sector bond fund from a veteran fund manager his pick this week.

 Jillian Johnsrud, the podcaster behind "Retire Often," and the author of a new book out this week that goes by the same title, says that a lot of people mess up their retirement lifestyle by not preparing for it with smaller retirements — lasting a month or more — during their prime working years. Not only do these smaller times allow people to recharge and rejuvenate, they become dry runs for the real thing, allowing pre-retirees to sample ideas and then plan how to execute the best concepts. Johnsrud — who says she has retired at least a dozen times despite only being in her early 40s — says that small retirements are achievable, even by workaholics (like this show's host) with some foresight and planning. Chuck Carlson, chief executive officer at Horizon Investment Services — longtime publisher of The DRIP Investor newsletter — returns to the show to help Chuck answer a listener's question about how to deal with an inherited portfolio of stocks all held in dividend reinvestment programs. Chip Lupo discusses the 2025 Money and Relationships Survey from WalletHub, which showed that nearly one in three people think their relationship is limiting their financial growth, with communication (or a lack thereof) being at the heart of the problem. And Chuck starts his interviews from FinCon '25 in Portland, Ore., by chatting with Doug Nordman of MilitaryFinancialIndependence.com, who says that while current events have some military members reconsidering their work choices, that action is appropriate and happens in all times, but it doesn't mean that military families will be abandoning their financial plans even if they change careers before achieving military status that could set them up for life.

Conrad Doenges, chief investment officer at Ranger Investment Management — manager of the Ranger Small Cap and Ranger Micro Cap funds — says that smaller companies have suffered as an asset class because corporate earnings have struggled to meet growth expectations. While there is an expectation that small companies will benefit from a cut in interest rates and from deregulation policies from the government, Doenges says in the Market Call that earnings expectations remain muted, so the long awaited rally in small caps could come, but be less than investors have been waiting for. Jeffrey Ptak, managing director at Morningstar Research Services, discusses his recent research into funds that have massive amounts of success to become darlings of the media and of investors, and how they tend to disappoint just after the flood of money comes in. While the results are not surprising, Ptak says it is more than just the typical "regression to the mean" that knocks these hot funds from the ranks of top performers.  Allison Hadley discusses a mid-year tariff survey from Bid-on-Equipment.com which showed that 1 in 5 Americans are stockpiling goods trying to beat price hikes, even though they mostly had to guess on which goods to purchase until tariff policies were firmed up. The survey also showed that nearly 80 percent of consumers are changing their spending habits, mostly by cutting back, which could be a bad sign for the economy moving forward.

David Giroux, chief investment officer at T. Rowe Price — named Morningstar's Outstanding Portfolio Manager for 2025 for his work at T. Rowe Price Capital Appreciation — says his allocation fund is holding near its highest levels ever of bonds, specifically intermediate fixed-income, largely because he thinks stocks are overvalued and real growth will remain hard to find. Giroux — who has beaten the average peer in his Morningstar asset class for 17 consecutive years, the longest streak in the entire fund industry — has long disdained investing in foreign stocks and says the rally that 2025 has produced overseas is an anomaly and that no one "should ever feel a need to own an inferior index just for diversification purposes." In the wide-ranging interview, Giroux says that the Magnificent Seven stocks have actually been the Mag 6, plus Tesla, saying that the car maker has no business being in the portfolio of leading securities. David Trainer, president of New Constructs, put Klarna in The Danger Zone in April, when the buy-now, pay-later financial firm was attempting to go public but put off the process in the face of the market's drop after "Liberation Day." Now the company is back attempting an initial public offering, and that brings them back under Trainer's scrutiny again, before they ever get launched as a stock. Natalia Brown, chief consumer affairs and creditor relations officer for National Debt Relief, discusses the firm's survey showing that six in 10 American parents are going into debt for their children. She talks about what parents are foregoing for their own lives to help the kids, and what they are paying for that puts them into debt.

Jim Welsh, author of “Macro Tides” and the “Weekly Technical Review,” says he thinks the stock market "is reaching an inflection point," saying that the next time the Standard & Poor's 500 makes new records but without support from the highs in the advance-decline line, he will take it as a sign that the stock market is about to roll over.  Welsh says that several momentum indicators suggest a short-term decline could be between 3 and 7%, at which point he expects a bounce-back that lasts only until the economic concerns take hold. Welsh says a rise in layoffs would show that the market has gone from mild slowing to something more active, If job growth slows markedly "and we get to a point where the economy starts to meaningfully slow down, that is going to be the trigger for a much deeper and more prolonged decline." That drop, he says, could fulfill a 17-year cycle which would drop the S&P 500 by thousands of points.  Rob Thummel, senior portfolio manager at Tortoise Capital, says that this is "the best time I have ever seen" in a three-decade career to be investing in energy. Thummel, who manages Tortoise Energy Infrastructure, notes that the U.S. has grown into the largest energy producer and energy exporter in the world; coupled with emerging energy needs caused by the expansion of artificial intelligence, it will drive demand growth "for decades to come." Chuck Carlson, chief executive officer at Horizon Investment Services — which publishes the "Best Dividend and Income Investments" newsletter — brings the proprietary Quadrix system and its multi-factor evaluation process to the Money Life Market Call. Plus Allison Hadley discusses a PartnerCentric.com survey which showed that more than 40% of Americans say they're actively reducing social media use in 2025, with nearly 20 percent having already quit at least one app this year as they try to take more control of their personal lives.

The Powerball jackpot that went unclaimed on Wednesday night will top $1.7 billion for its next drawing this weekend, and will mark the 13th time in less than a decade that the big prize has been north of $1 billion. Chuck talks about why jackpots have grown this large, how you might use the lottery as a personal finance tool — even if, like him, you never buy a ticket  and why the odds are never in your favor. In the "ETF of the Week," Todd Rosenbluth, head of research at VettaFi, looks to a technology fund that mixes the big names and the tech-adjacent" plays to create an opportunity for investors seeking a growth bost for their portfolio. Natalie Iannello discusses a survey done for FrontDoor which looked at how homeowners were keeping cool under the heat of more extreme water bills this summer. Plus Seth Cogswell, manager of the Running Oak Efficient Growth ETF, brings his disciplined approach to stocks — which focuses at least as much on reasons to sell as it does on opportunities to buy — to the Market Call

Rob Thummel, senior portfolio manager at Tortoise Capital — manager of the firm's energy infrastructure funds as well as its new AI Infrastructure ETF — says that in a three-decade career, he has never seen a better time to be looking at the energy sector, thanks to being the world's largest energy producer with opportunities to remain the global leader, but also due to the power needs created by artificial intelligence. He says "Electricity is the new oil," driving the economy forward the way oil companies used to. Thummel notes in his Market Call interview that he has now seen some Bitcoin mining companies morph into data centers, largely because the megatech companies are paying to get access to the power supply that the crypto mining companies have developed. Lester Jones, chief economist for the National Beer Wholesalers Association, discusses the latest "Beer Purchasers Index," a forward-looking measure of economic activity that he says has reached the lowest point in its 10-year-plus history, indicative of a "beer recession," with less orders, declining sales and other economic indicators showing an alarming down cycle for the industry that could be a bad sign for the broader economy. In the Big Interview, Rick Pitcairn, chief global strategist at Pitcairn — a firm that works with ultra high net worth families managing money over lifetimes — discusses the importance of not allowing today's bumps and headlines become something bigger in a portfolio. It eliminates "the execution risk of timing," and allows the market to turn a steady return in the high single digits" to become "a super wealth accumulator." As a result, he's fully diversified, and suggesting investors lean into international stocks and bonds, hard assets and more now.

 Chuck warned listeners a few weeks ago that he had been hit by a computer virus, and that they should not open a spam e-mail that was being sent from one of his accounts. But that was the beginning of his online misadventures, because he hadn't just gotten a virus, he was hacked. Thieves have stolen nearly $4,000 from an online bank account, and they did it right under his nose. He explains how it happened, how he caught it, why he thinks he will eventually get restitution from the bank and more. Stephen Kates discusses a survey on financial regrets from Bankrate.com, which showed that the most common regret for Americans now is not saving for retirement early enough, followed by racking up too much credit card debt.  Nick Pisano talks about research from Clever Real Estate showing that 60 percent of Americans believe that having a nearby short-term rental unit from a site like AirBNB lower's a home's appeal and value. The problems run from rental guests not caring about the neighborhood they're staying in to the constant in-and-out reducing the quality of life for the locals.   In the Market Call, John Cole Scott, president of CEF Advisors, discusses his "trifecta analysis" of closed-end funds and how frequently he will add or drop funds to take advantage of market conditions but also tax circumstances.

Dana Samuelson, president of American Gold Exchange — a former president of the Professional Numismatists Guild — sees "a meaningful rally in gold" coming once the Federal Reserve makes multiple rate cuts, but adds that turmoil over Fed leadership and concerns that government data could be compromised or less transparent would build "a better bed from gold to rise from." Samuelson said he expects gold to be in the $3,900 to $4,200 per ounce range within a year, and that his forecast might be conservative if there is any sort of global debt problem or currency collapse.  Kimberly Flynn, president at XA Investments, discusses the recent executive order signed by President Trump that allows a dramatic expansion of alternative assets to be part of 401(k) and other retirement plans. While headlines have made it seem like crypto bros will blow up their retirement plans with alternatives, Flynn discusses how firms running life-cycle and target-date funds may decide to make allocations to alternative asset classes, exposing everyday investors to alternatives, but in safer ways than most industry watchers are imagining. Jay Hatfield, chief executive officer for Infrastructure Capital Advisors, brings his macro-first approach to the Market Call, noting that rate cuts should be "tremendously positive for the market" and are keeping him bullish even as the market enters September, a seasonally weak time for stocks.