Podcast Summary: The Stacking Benjamins Show – The Money Habits to Keep and Ditch in 2026 (SB1791)
Date: January 16, 2026
Hosts: Joe Saul-Sehy, OG, Doug
Panelists: Paula Pant (Afford Anything), Jesse Kramer (Personal Finance for Long-Term Investors)
Theme: A roundtable discussion on which personal finance habits and trends should be kicked to the curb in 2026, and what new, fashionable money moves listeners should adopt.
Main Theme: Financial Fashion—What’s “In” and “Out” for 2026
In a spirit akin to a new year’s fashion show, the panel explores which personal finance behaviors, strategies, and “money fashions” should disappear with 2025, and what smarter, more sustainable habits are in style for 2026. With personal anecdotes, candid humor, and insights from their own financial journeys, the hosts and guests provide practical advice for listeners looking to update their money management wardrobe this year.
Key Discussion Points & Insights
1. Chasing Hot Trends vs. Thoughtful Diversification
- Out: Chasing last year’s hot asset class (international equities, gold, meme coins).
- Paula Pant highlighted how, after long ignoring international equities, “everybody started chasing them in 2025 just because they were the top performer.” The same happened with gold and crypto ([08:46-13:12]).
- Quote: “It’s good that they’re getting diversification, but it’s the right decision for the wrong reason.” — Paula Pant (09:24)
- In: Decide on a thoughtful asset allocation and stick with it.
- OG: “Pick your asset allocation, rebalance it once a year... then just be okay with what’s going to happen in the short run, because in the long run, you’ll be fine.” ([10:01-11:21])
- Jesse Kramer joked about launching the “Don’t Be an Idiot, Invest in Meme Coins” podcast, poking fun at performance-chasing ([11:40-12:33]).
2. Ignoring Taxes vs. Proactive Tax Planning
- Out: Neglecting your tax return, procrastinating with extensions.
- Jesse: “Not reviewing your tax return is such a passé 2025 thing.” ([13:58])
- OG: “For some reason, it’s been this trend: ‘It’s so cool to file my taxes in August. Don’t worry, I have an extension; it’s beef, it’ll be fine.’ Stop. Do your friggin’ taxes now.” ([16:06-16:41])
- In: Building a tax review routine and learning from your return.
- Paula likens the unpleasantness of taxes to “one day of hell, like swallowing the medicine, you’re done,” advising listeners to make it a dedicated event with a reward at the end ([18:56-20:22]).
- Joe suggests handling paperwork monthly instead of all at once for a less painful experience ([20:27]).
3. Lifestyle Creep & Mindless Spending vs. Purpose-Driven Spending
- Out: Rampant lifestyle creep, especially with conveniences like DoorDash or UberEats.
- OG: “It was so hot last year: spending willy nilly, DoorDash was off the hook...not in 2026.” ([21:10])
- Doug & Jesse swap stories about the high cost of “filling up under the tree” for kids and habit creep as children age ([22:11-23:46]).
- In: “Spending on Purpose”
- OG challenges: Try picking up your food instead of delivery to manage spending and appreciate costs. “I’m close to saying DoorDash and UberEats are the devil also.” ([25:24-28:21])
- Quote: “The 2026 new line of spending is very, very, very sexy. It’s spending on purpose.” — OG ([25:24])
4. Financial Myopia vs. Holistic Planning
- Out: Focusing too much on one area (just investments, just taxes), missing the “big picture.”
- OG: “Just looking at one area or focusing on one thing as it relates to your overall financial picture, I think is so 2025...get over it.” ([44:09])
- Paula warns of “missing the forest for the trees” ([44:43]).
- In: Regular, comprehensive reviews of all key financial planning areas.
- OG explains their process: focus on each area (estate planning, insurance, portfolio, etc.) on a rolling cycle, so no aspect is neglected for more than a few years ([47:26-48:50]).
5. Economic Complacency vs. Preparedness for Downturns
- Out: Assuming bull markets and strong employment will never end.
- Jesse: “Everything goes out of style eventually, including some economic things...I want our stackers to be prepared for that eventuality.” ([49:05-50:33])
- Paula: “Some people are starting to believe the market is a high-yield savings account, which of course it is not.” ([51:14-51:42])
- In: Planning with realism, matching investment types to timeframes, and avoiding “perma-bull” or “perma-bear” mindsets.
- Jesse: “The answer is not to become a perma-bear...simply to find that more of a realist position.” ([53:20])
6. Housing Market Pessimism vs. Creative Solutions
- Out: Doom-and-gloom about housing affordability and mobility.
- Paula discusses the dual-pessimism of locked-in homeowners and buyers priced out, with everyone sitting on the sidelines ([54:21-55:31]).
- In: Cautious optimism, creativity (house hacking, co-purchasing, creative financing).
- Paula: “If you think creatively...that’s not just real estate, that’s a lot of your financial plan. Like, when you think you can’t do something, think a little bit more creatively.” ([62:16])
- Exploring options like duplexes, co-buying, or renting out space can bridge the gap for first-time buyers ([60:47-62:16]).
Notable Quotes & Memorable Moments
- Paula Pant: “There are a lot of instances of the tax tail wagging the decision dog.” ([44:43])
- OG: “Do your friggin’ taxes now...CPA is overwhelmed. Don’t dump it on them on April 9th.” ([16:41])
- Doug: “Lifestyle creep happens when kids are young; the spending can get out of control.” ([22:39-23:24])
- Jesse Kramer (on market cycles): “Sometimes bull markets will end...just like whale tails went out of style, so too will these economic trends.” ([49:05-50:25])
- OG (on resilience): “Being boring and doing the right thing over a long period of time for clients pays off.” ([63:54])
- Paula Pant (on paperwork): “If you’re a very distractible person, paperwork is the bane of my existence...I dedicate a day to it, and anchor it with maybe a nice dinner at the end.” ([18:56-20:22])
Timestamps for Key Segments
- [08:46] – What was “in” for 2025: Chasing hot assets
- [13:12] – What to do instead: Set allocation, rebalance, and forget about it
- [13:58] – Reviewing your tax return: Tax fashion faux pas
- [16:06] – Why you should stop procrastinating on taxes
- [21:10] – Lifestyle creep and spending habits
- [25:24] – “Spending on purpose” – 2026’s money trend
- [44:09] – The problem with financial myopia
- [49:05] – Preparing for economic cycles, not just good times
- [54:21] – Housing market pessimism and mobility concerns
- [62:16] – 2026 solution: Thinking creatively about home ownership
Panel’s 2026 “Money Fashion” Takeaways
- Decide on your asset allocation, rebalance, and ignore the performance noise.
- Embrace regular tax reviews, leveraging new changes in contribution/expense limits.
- Become intentional about spending; curb lifestyle creep by questioning convenience.
- Take a holistic approach: Rotate through all areas of personal finance—not just investing.
- Be prepared for downturns—don’t let good years lead to complacency.
- Face real estate realities with optimism and creativity, not despair.
Fun & Memorable Podcast Moments
- Recurring jokes about old/young panelists, fashion analogies, and trivia competition (new “margin call” rules).
- Paula’s long streak of not winning the trivia challenge became an ongoing punchline ([29:47-31:56]).
- OG invents financial “fashion lines”: high-waisted “spending on purpose.”
- Listeners cited as part of the “show,” with shoutouts from YouTube and newsletter.
For Listeners: Your Money Makeover for 2026
- Resist the urge to chase performance—be steady and strategic.
- Get empowered about your taxes—knowledge is saving.
- Watch out for lifestyle inflation, and get mindful about your spending choices.
- Review all aspects of your financial life, not just the ones that interest you.
- Stay realistic, but optimistic—and get creative if the math doesn’t add up.
As always, the Stacking Benjamins team keeps it light, silly, and practical—making even estate planning and taxes (almost) fun.
For more stories, expert tips, and laughs, check out the full panel on The Stacking Benjamins Show.