finance
Named Best Personal Finance Podcast by Bankrate.com and Kiplinger — and the only podcast the Plutus Awards retired from competition after winning twice — The Stacking Benjamins Show is personal finance that doesn’t put you to sleep. Hosts Joe Saul-Sehy (former 16-year financial advisor, ex-WXYZ-TV “Money Man”) and Josh “OG” Bannerman, CFP (Certified Financial Planner, Bannerman Wealth) sit around the card table in Joe’s mom’s half-finished basement in Texarkana and talk money with the smartest guests in personal finance, investing, and behavioral economics. As Fast Company wrote, the show “strikes a great balance of fun and functional.” Every Monday, Wednesday, and Friday: expert guests, real headlines, listener questions, and Doug’s trivia. Topics include investing, retirement planning, budgeting, real estate, behavioral finance, taxes, and financial independence — for anyone who wants to be smarter about money without being talked down to. Subscribe to The 201 — the free newsletter t
Panelists discussed strategies for managing a concentrated company stock position when it triples in value to 38% of a portfolio. Paula Pant advised trimming it to 10% if it is earmarked for retirement, while OG suggested considering momentum, writing options, or building savings elsewhere to lower the percentage without triggering capital gains taxes.
The panel debated whether home buyers should proceed with a home purchase if they are left with only $4,000 in cash after closing. Jesse Kramer argued that leaving less than 1% of the house value in cash is too risky for emergencies, while Paula Pant and OG discussed the necessity of managing ongoing monthly payments and maintaining appropriate liquidity for maintenance.
The hosts considered whether to accept a new job offering $40,000 more when the previous role experienced high turnover with four departures in three years. OG advised taking the cash and immediately preparing a resume, while Paula Pant emphasized evaluating the direct manager and interpersonal vibes during the interview.
Jesse Kramer addressed the common misconception that receiving a pay increase and moving into a higher tax bracket subjects all income to the higher rate. He explained that only marginal dollars are taxed at the higher bracket.
OG advises against investing 10% of a portfolio in a leveraged stock market fund, citing a potential to lose 98% of the investment. He explains that the daily reset mechanism of leveraged ETFs amplifies losses on down days, making them risky for long-term holding.
Jesse Kramer expresses caution regarding newer, active-themed ETFs, suggesting they often come with higher fees and lack academic rigor. He likens some thematic ETFs to 'jokes' or 'memes' rather than serious investment vehicles, recommending avoidance for serious investors.
OG argues that the obsession with beating market benchmarks like the S&P 500 is misguided. He believes the focus should be on reaching personal financial goals, not on outperforming an arbitrary list of stocks. Jesse agrees, suggesting that the analysis of benchmarks is often flawed.
The panel discusses the dilemma of a stock becoming 40% of a portfolio after a significant win. Doc G advocates for selling and diversifying to protect wealth, highlighting the risk of concentration and the impact of taxes. OG, however, suggests holding onto the winner, comparing it to potentially holding Home Depot, which yielded massive returns over decades.
OG strongly advises against relying on guaranteed income streams in retirement, calling it a 'fool's errand' and a 'giant waste of time.' He argues that the primary risk in retirement is not a lack of guarantees but money failing to outpace inflation, which can happen with overly conservative, flat-rate income plans.
Doc G expresses being 'out' on retiring five years earlier if the financial plan has an 80% success rate, deeming a 20% failure rate too significant. He emphasizes that retirement shouldn't be synonymous with happiness and that the goal should be control over one's time and doing enjoyable work, rather than solely stopping work.
Jesse Kramer indicates he is 'in' on fully funding his children's college education, even if it means working two additional years before retirement. He explains his priorities have shifted towards enjoying his work and supporting his family, making the trade-off acceptable.
A listener, JD, inquired about why some of his funds issued cash dividends while individual stocks issued qualified dividends. OG explained that all dividends are cash dividends, but the distinction JD observed relates to how they are taxed.
Following up on the dividend discussion, a listener asked OG about the importance of asset location in his practice, specifically whether tax ramifications or the timing of when money is needed is more critical. OG stated that both are important and depend on the value of different investment buckets.
An anonymous listener asked how much they should save for college. The host explained that the answer depends on many factors, including public vs. private school, four-year vs. two-year degrees, the child's aptitude for scholarships, current costs, and inflation. Crucially, they emphasized prioritizing retirement savings over college savings, as one can borrow for college but not for retirement.
The host recommended 529 plans as a great way to save for college. They highlighted the benefits of tax-deferred growth and tax-free withdrawals for qualified education expenses.
At the FinCon Expo, a panel featuring Paula Pant, Joseph Morback, and Jesse Cramer discussed what worries their audiences and the unique collaborative atmosphere of the financial creator community. They highlighted that unlike traditional finance conferences, FinCon attendees prioritize audience benefit over personal gain.
The podcast host shared personal experience with decreased energy, brain fog, and concentration issues starting in his 30s, attributing it to a natural decline in testosterone. He claims to have found a solution in a supplement called Mars Men, which he says helps free up bound testosterone and support natural production.
The importance of reliable shipping for business operations was highlighted, with UPS Ground Advantage being presented as a solution. The service offers a secure, nationwide network, near real-time tracking, and affordable upfront pricing.
Robin Wigglesworth, author of 'Trillions,' explained how the bond market's reaction to President Trump's proposed tariffs on April 9th, 2025, highlighted its significant influence. Despite initial stock market sell-offs and Trump's defiance, the bond market's "violent sell-off" eventually prompted a pause in negotiations.
Robin Wigglesworth, editor of the Financial Times's AlphaVille blog, clarified the history of Exchange Traded Funds (ETFs) and index funds. He stated that Jack Bogle, the founder of Vanguard, was not responsible for their creation, contrary to popular belief.
The Built loyalty program, previously focused on rent payments, has expanded its offerings. As of 2026, homeowners can now earn points on their mortgage payments, up to 1.25 times the amount.
Ethos has been highlighted as a leading provider of life insurance that does not require a medical exam. Business Insider named Ethos the number one no-medical-exam instant life insurance provider in March 2021, and it holds a 4.8 out of 5-star rating on Trustpilot.
The podcast highlighted Granola, an AI-powered notepad designed for transcribing and organizing meeting notes. The program uses AI to turn rough notes into clean, structured, and useful summaries after a meeting concludes.
Longevity and wellness expert Linda Gratton, along with economist Andrew Scott, advocate for planning as if individuals will live to 100 or beyond. This perspective significantly alters traditional retirement planning, suggesting longer working lives are necessary.
Organizational theorist Linda Gratton argues that early retirement and withdrawal from society can lead to atrophy. She emphasizes the value of remaining part of the workforce for personal well-being and societal contribution.
The episode touches on lessons for personal finance that can be learned from the songwriting of Dolly Parton. Specifically, the discussion points to 'I Will Always Love You' as a song written by Parton, despite its popular association with Whitney Houston.
The Stacking Benjamins Show hosts discuss the nuances of retirement planning, emphasizing that the amount saved is less important than how much is kept. They aim to provide a realistic picture of what individuals need to consider before leaving the workforce with varying retirement nest eggs.
OG recounts his experience completing a 100-mile bicycle ride, which he now regrets. He humorously states the bike is for sale and expresses a newfound appreciation for cars.
The transcript highlights USPS Ground Advantage as a reliable shipping solution for businesses. It emphasizes secure nationwide networks, affordable upfront pricing, and dependable delivery to ensure logistics are handled efficiently.
Quince is promoted for its focus on high-quality, timeless wardrobe staples made from premium materials like cashmere and organic cotton. The brand emphasizes its direct-to-consumer model, offering items at significantly lower prices than traditional retailers.
Guest Todd Havens argues that most people's financial struggles stem from their thinking, not a lack of money. He shares his personal journey from deep debt and a cancer diagnosis to becoming a first-generation millionaire, emphasizing that a shift in mindset is key to building wealth and living a fulfilling life.
Co-host Joe recounts a personal financial misstep: putting his honeymoon entirely on credit cards. This experience led to significant debt and a feeling of remorse, highlighting the danger of believing one 'deserves' luxuries they cannot yet afford.
Todd Havens, a guest on the show, overcame significant financial and personal challenges to achieve success. He entered his journey with over $60,000 in student loan debt and a diagnosis of incurable cancer, turning these adversities into a powerful motivation for change.
Retirement success is not solely dependent on the amount of money saved, but rather a holistic approach encompassing five key factors, according to retirement expert Wes Moss. He emphasizes that while financial security is important, community, socialization, health, and purpose are equally crucial for a fulfilling retirement.
Retirement expert Wes Moss suggests that true retirement readiness is less about a specific age and more about reaching a point where work becomes optional. He notes that some individuals may achieve this 'optional work' status several years earlier than commonly assumed.
Wes Moss categorizes retirement financial readiness into 'zones' based on liquid investable assets and corresponding happiness levels. He identifies a 'red zone' for those with $100,000 or less, a 'neutral zone' from $100,000 to $999,000, and 'green zones' starting at $1 million, where happiness levels significantly increase.
Former Planet Money hosts Jacob Goldstein and Robert Smith have launched a new podcast titled "Business History." The show will explore significant ideas, people, and companies throughout business history, including both positive and negative examples.
The Stacking Benjamin's show discusses using the concept of 'friction' to encourage saving, drawing on a Wall Street Journal article. They suggest that while technology removes friction from spending, individuals should intentionally create friction for beneficial financial behaviors, such as saving for retirement.
During Financial Action Month, the hosts of The Stacking Benjamin's Show emphasized the importance of making saving for retirement easy by automating the process. OG suggested that having contributions come out of a paycheck automatically is a key strategy.
USP is emphasizing the reliability of its Grounded Advantage service, ensuring secure nationwide network, door-to-door tracking, and affordable upfront pricing. This service aims to remove uncertainty for businesses by guaranteeing dependable logistics.
Indeed is promoting its Sponsored Jobs feature as a solution for small businesses struggling to find quality talent. The service boosts job posts in search results to reach candidates meeting specific criteria, with payment only for results.
During a game show segment, Paula Pant asked the Magic Eight Ball if she would continue staying at Holiday Inn for the foreseeable future. The Magic Eight Ball answered affirmatively, stating 'Yes, it is certain.'
The hosts reflected on a previous discussion about financial advice from 2020, noting that what was considered sound then may not be applicable today. They suggest that good financial planning involves continuously reassessing rules rather than just memorizing them.
The podcast mentions a forthcoming discussion about Robinhood, noting its phenomenal advertising while also highlighting that some hosts, like OG, are not fans. This indicates that even strong advertising doesn't always translate to universal approval.
The Buffalo Bills' new stadium is reportedly facing criticism for poor sightlines and small video screens. Joe Sal-See-high mentioned that the screens are reportedly "tiny little screen, big as your iPhone," and listeners may already be complaining about the new facility.
The Boston chapter of the Stacking Benjamins group has adjusted its meeting times and dates to be more accommodating. They have moved from 6-7 PM to 6:30-7:30 PM and from the second to the third Wednesday of the month, with one member noting the change helps accommodate a school teacher's schedule.
Maya Corbic's Wealthy Kids Club has expanded to include families, not just kids, in its financial education efforts. The club helps families budget, manage money, and pursue financial goals, with Corbic noting that her Instagram videos, while aimed at kids, also educate parents who didn't learn these concepts growing up.
A former financial advisor, now running a company called $100k Advice, suggests that optimizing one's life requires a strict and non-ambiguous approach. The advisor believes there is 'no room for gray areas' when aiming for self-improvement.
Doug shared an anecdote about trying to 'optimize' his late-night snack habit, specifically eating cereal. He attempted to make it colder by adding ice cream, but concluded this was 'over optimization' that did not work.
Jesse Krabbers mentioned that a planned mid-October hiking trip to the Adirondacks in upstate New York could be risky due to the potential for snow and ice at higher elevations. He expressed a desire to avoid hiking on an icy mountain.
Len Penzo returned to The Stacking Benjamin Show to present his 18th annual sandwich survey, a method he uses to measure inflation. He started the survey 18 years ago to compare the cost of making his children's lunches at home versus buying school lunches.
In Len Penzo's latest sandwich survey, salami has risen to become the third least expensive sandwich for a brown bag lunch. This marks a significant increase from its previous position as the seventh least expensive in 2024.
The BLT sandwich has consistently held the title of the most expensive option in Len Penzo's annual sandwich survey for 18 years. Despite its cost, Penzo notes it's still a relatively healthy option.
Len Penzo shared a recent finding that school lunches and breakfasts are free for all children in California, regardless of income. He questioned the quality of these free lunches compared to homemade options.
Dr. Jordan Grummet (Doc G) discusses the dysfunction in the healthcare system, highlighting how doctors' business incentives, driven by insurance company payments, can conflict with patient advocacy. He suggests that patients need to be their own advocates, stay informed, ask questions, and vote with their dollars by choosing healthcare providers who are willing to prioritize patient needs.
Dr. Jordan Grummet (Doc G) explains that the healthcare system is burdened by defensive medicine, costing $40-50 billion annually. This practice, driven by fear of malpractice suits, leads to doctors ordering more tests and procedures than necessary, which ultimately increases costs for both the government and insurance companies, and thus for patients through taxes and premiums.
Dr. Jordan Grummet (Doc G) provides statistics on medical malpractice lawsuits, stating that approximately two-thirds of cases are dismissed before trial, and 8 out of 10 cases that go to court find in favor of the physician. He notes that the likelihood of a patient winning a malpractice suit is less than 10%, and even then, over 40% of the award goes to the lawyer.
Doug shares a personal anecdote about the difficulty in obtaining cost information for medical services, highlighting a receptionist's inability to provide an estimate until after the service is processed through the computer. This lack of transparency in healthcare pricing is a recurring issue, with some patients reportedly receiving bills years after treatment.
Built, a loyalty program, has introduced three new credit cards (Platinum, Obsidian, and Blue) that allow homeowners to earn rewards on mortgage payments. As of 2026, these cards enable users to earn up to 1.25 times points on mortgage payments, in addition to rent payments, which can be redeemed for travel, Amazon purchases, and other benefits.
Whatnot, a live shopping platform, is highlighted as a place where sellers can build thriving businesses by connecting with repeat customers. The platform supports various categories, including collectibles, electronics, and fashion, and claims sellers on Whatnot sell ten times more than on other marketplaces due to the engaged audience that spends over an hour a day on the app.
Jesse Mecham, founder of You Need A Budget (YNAB), argues that the key to ending money anxiety isn't necessarily a tighter budget or more complex spreadsheets, but rather understanding the purpose of one's money. He suggests that asking 'What's the money for?' is more effective than retrospectively tracking expenses like 'Where did my money go?' because it focuses on future intentions.
Jesse Mecham believes that budgeting can be transformed into an art form to make it more enjoyable and effective. He posits that shifting from tracking past spending to understanding future financial goals can alleviate money worries and lead to a greater sense of control.
Built has announced new credit card options that allow homeowners to earn rewards points on their mortgage payments. The Palladium, Obsidian, and Blue cards offer accelerated point earning on housing payments, which can be redeemed for various rewards including airline miles and hotel stays.
Showing the latest 15 of 25 covered episodes.