The Stacking Benjamins Show

Live from Joe's mom's basement (where humility is encouraged and spreadsheets are optional), the crew tackles a deceptively simple question. If most people think they're above average with money, what advice actually helps someone who isn't?

Joe Saul-Sehy, OG, Doug, Jesse Cramer, and guest Whitney Hanson (Money Nerds podcast) run a thought experiment inspired by Morgan Housel's observation that nearly everyone believes they're financially smarter than the median. What straightforward moves keep someone from needing last minute financial Hail Marys?

The answer isn't flashy. It's systems.

Whitney kicks things off with a practical starting point: identify your knowledge gaps. Tools like Investor.gov quizzes can reveal blind spots, and she suggests theming your learning (one focus per month) so financial literacy doesn't feel overwhelming.

From there, the conversation turns to controllables: cash flow, savings rate, lifestyle inflation, and career capital. Because while markets bounce around, your habits are yours.

The gang also introduces the idea of a tactile money leak audit, physically reviewing spending to spot waste that autopilot budgeting apps can miss. It's less glamorous than crypto speculation but far more effective.

Investing gets reframed too. Instead of treating it like a mysterious Wall Street game, they suggest thinking of it as owning small pieces of companies you already know and use. Start small. Automate it. Build reps. Confidence follows action.

Insurance and estate planning round out the episode. The crew urges listeners to shop multiple advisors, understand policy details before signing, use AI to help decode fine print without blindly trusting it, and avoid overconfidence just because something sounds right.

Doug keeps things lively with trivia revealing that Johnny Carson's 1982 DUI fine was a very specific $603, and OG once again proves suspiciously good at guessing.

What You'll Learn:

Why most people overestimate their financial knowledge and what to do about it

How to identify and close your personal money knowledge gaps

The key financial variables you actually control

How to perform a simple money leak audit

Why small, automatic investing beats waiting for the perfect moment

How to make investing feel familiar instead of intimidating

The basics everyone should understand about insurance and estate planning

Why repetition builds financial confidence faster than theory

The Big Takeaway:

You don't need advanced tactics. You need consistent systems. Focus on what you control. Automate the boring stuff. Learn one thing at a time. Build margin. Repeat.

Because the goal isn't to be above average. It's to be steady enough that you never need a desperate Hail Mary.

This Episode Is For You If:

You feel like everyone else has money figured out except you

Financial advice usually feels too complicated or assumes knowledge you don't have

You're tired of feeling behind and want simple systems that work

You want to build confidence through action, not just theory

You believe steady progress beats trying to be perfect

Question for You:

What was the first simple money habit that changed your trajectory? Share it in the Spotify comments or The Basement Facebook group. Your small win might be exactly what another Stacker needs to hear.

FULL SHOW NOTES: https://www.stackingbenjamins.com/bottom-50-money-tips-1809/

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201

Enjoy!
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Live from Joe's mom's basement (where the jokes are free but hospital care apparently isn't), the Stacking Benjamins crew tackles two very real financial stressors: surprise medical debt and a shifting housing market.

First up is Imani Vance, who joined the Coast Guard at 19 and soon faced a nightmare scenario. What started as appendicitis escalated to severe sepsis after limited on-base resources and long waits for off-base care. After hospitalization, including treatment for an abscess and eventual appendix removal, Imani received a bill totaling roughly $43,000 to $45,000.

And here's where it gets worse. She didn't qualify for VA help because she hadn't yet served 180 days. Accessing Coast Guard records proved difficult. The bill arrived after the care, opaque, overwhelming, and completely disconnected from what she had agreed to or expected.

If you're a Stacker, you know this feeling. The stress isn't just the number. It's the lack of clarity.

Imani shares how she started researching options, discovered the nonprofit Dollar For through Reddit, and used them to apply for hospital financial assistance. Dollar For helped her complete and submit the required forms, and within weeks, she was approved for 100% financial assistance, wiping out the bill entirely.

Joe Saul-Sehy highlights an important takeaway. Nonprofit hospitals are legally required to offer financial assistance. Many for-profit hospitals offer programs, too. Income thresholds are often higher than people assume. The applications can be confusing, which is where advocates like Dollar For can make a huge difference.

Instead of locking into $300 to $500 monthly payments for years, Imani walked away debt-free and with a completely different outlook.

After Doug drops trivia about the youngest bank robber (yes, really), the crew pivots to housing. A recent Wall Street Journal/Redfin headline suggests the housing market may be tilting toward buyers, with more homes selling below list price and average sales around 8% under asking.

Joe and OG break down what that means for Stackers, not in headline hype terms but practical life terms.

What You'll Learn:

Medical Bills and Financial Assistance:

• Why medical debt feels different from other debt

• How hospital financial assistance programs work

• Why many people qualify but never apply

• How nonprofits like Dollar For can help navigate the paperwork

• Why you should always ask for itemized bills and assistance options

Housing Market: Think Forward, Not Backward:

• Why you shouldn't get stuck in your mortgage just because you locked in a low rate

• How anchoring to past rates can cloud present decisions

• Why negotiating power is shifting and how to use it

• The importance of building financial margin when income rises

• Smart, low cost staging tactics, including hiring a pro for just an hour of advice

• How AI tools can help with pricing and presentation ideas

The Big Takeaways:

Before paying a massive medical bill, check whether you qualify for assistance. Financial stress often comes from confusion. Clarity is power. Housing decisions should be forward-looking, not emotionally anchored to the past. Margin and flexibility beat perfect timing.

This Episode Is For You If:

• You're facing medical debt and thought you had no options

• You've been putting off dealing with a hospital bill because it feels hopeless

• You're stuck in a low rate mortgage and wondering if you should move

• You want to understand what's really happening in the housing market

• You believe there's always more to the story than the bill or the headline

Question for You:

Have you ever negotiated or reduced a bill you initially thought was non-negotiable? Share your story in the Spotify comments or The Basement Facebook group. Your experience might help another Stacker avoid paying more than they should.

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Live from Joe's mom's basement (complete with dog mugs, birthday roasting, and Doug polishing his trivia crown), the crew tackles a headline that caught plenty of attention. Suze Orman backing off her long held stance that everyone should work until age 70.

Does that mean you shouldn't work longer? Not exactly.

Joe Saul-Sehy, OG, Doug, and special guest Len Penzo break down the math behind working into your late 60s or beyond. More years to save, more compounding, fewer years drawing down assets. It's powerful stuff. But they also remind Stackers that work doesn't have to mean the same grind, and that retiring and claiming Social Security are two completely separate decisions.

Len shares why he plans to delay Social Security until 70, walks through the break even math versus claiming at 62, and highlights the importance of survivor benefits for spouses. At the same time, the crew emphasizes that health, longevity expectations, and personal priorities can completely change the right answer.

Suze's updated advice leans heavily on stress testing your retirement plan, and that's where the basement really digs in. What happens if inflation sticks around? If your side hustle disappears? If returns are lower than expected? The team argues that instead of chasing the perfect retirement date, you should solve for flexibility. Avoid analysis paralysis but don't skip the planning either.

They also debate liquidity (hint: it doesn't mean stuffing your mattress with cash), share a cautionary tale about delayed IRA access, and remind listeners that logistics matter just as much as spreadsheets.

In the TikTok Minute, a retiree reframes time as priceless instead of something to maximize. That sparks a thoughtful conversation about identity in retirement, the adjustment period after leaving work, and what makes life satisfying once the paycheck stops.

Plus: A big community win as a fellow Stacker crosses the $1 million net worth milestone, stats on how common that really is, upcoming Stackers meetups, Doug's Gutenberg themed trivia, and unexpected retirement expenses involving squirrels and BarkBox. Because this is the basement, after all.

What You'll Learn:

• Why working longer can strengthen your retirement math and when it might not

• The difference between retiring and claiming Social Security

• How to think about Social Security timing, longevity, and survivor benefits

• What it means to stress test your retirement plan

• Why flexibility often beats perfect optimization

• The real meaning of liquidity and why too much idle cash can hurt efficiency

• How retirement success is often about time, not just money

• Why identity shifts matter just as much as account balances

The Big Takeaway:

Retirement doesn't require working forever. But it does require a coordinated plan, one that brings together your assets, Social Security strategy, spending flexibility, and (most importantly) how you want to spend your time. Because in the end, money is renewable. Time isn't.

This Episode Is For You If:

• You've been told to work to 70 and aren't sure if that's right for you

• You're trying to figure out when to claim Social Security

• You want to stress test your retirement plan but don't know where to start

• You're worried about the adjustment period after leaving work

• You believe retirement planning is about more than just hitting a number

Question for You:

If you could retire tomorrow, what would you spend more time doing, and what would you happily leave behind? Share your thoughts in the Spotify comments or The Basement Facebook group. Your answer might inspire another Stacker who's quietly wondering the same thing.

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Want your kids to grow into confident money decision-makers without turning every dinner conversation into a financial lecture? In this roundtable episode, Joe sits down with Livia (“Liv”) Roder, host of the Liv Lab Podcast, Karen Holland of GiftingSense.org, and John Lanza, host of the Art of Allowance Podcast to explore what actually helps kids understand money before the stakes get big.

Instead of theory, this discussion focuses on real moments when money suddenly becomes real: college price tags, house-hunting sticker shock, allowances that run out too fast, and purchases that teach better lessons than any lecture ever could. The panel shares practical ways families can build financial confidence through everyday decisions, honest conversations, and a willingness to let kids learn by doing.

What the Stacking Benjamins “Confident Explorer” will gain from this episode:


How to talk about money naturally so kids see it as a life skill, not a stressful taboo topic


Why modeling everyday behavior matters more than formal “money talks”


A simple shift from “Can I have it?” to “Is it worth it?” that builds independent thinking


How small spending mistakes become powerful teaching moments when handled without shame


Ways to introduce big topics like college costs gradually so kids feel informed instead of overwhelmed

Real-life money lessons that sparked the conversation:


Livia’s moments when money suddenly felt real, from college forms to realizing savings aren’t just “bank numbers”


Karen Holland’s memorable eighth-grade back-to-school budget experiment


Early allowance experiences that helped connect choices with consequences


Why kids absorb far more from overheard conversations and daily habits than parents expect

Practical strategies parents can use right away:


Starting with simple allowance systems or “jars” to visualize spending, saving, and giving


Karen’s “Does It Make Sense?” pause to slow impulsive purchases


Joe’s “circle back” technique, revisiting purchases later to reflect without criticism


Letting kids fail safely so regret becomes learning instead of embarrassment


Helping kids split costs or contribute toward purchases to create ownership

Navigating tougher parenting questions:


Should kids see financial stress, or should parents shield them?


How to practice age-appropriate honesty without creating anxiety


Why financial jargon like FAFSA or taxes can unintentionally intimidate teens


Bringing kids into real financial conversations so they build confidence early

Money challenges unique to today’s kids:


Teaching spending awareness in a tap-to-pay, frictionless world


Cash vs. cards vs. apps and how each changes behavior


Building a “pause habit” before spending when transactions feel invisible

If you could teach just one money skill…

The panel compares their top priorities:


Awareness of cash flow and where money actually goes


Thinking before buying instead of reacting emotionally


Paying yourself first and building saving habits early

Plus, a little basement fun along the way:


Favorite purchases that truly felt worth it (from snowboards to board games to a Kindle)


Stories that prove money lessons stick best when tied to real experiences


Resources and next steps from each guest, including tools, calculators, and upcoming episodes

This episode reinforces a core Stacking Benjamins idea: kids don’t learn money through perfect decisions. They learn through guided experience, honest conversations, and the freedom to practice while the stakes are still small.

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-teach-your-kids-about-money-1806

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201

Enjoy!
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Live from Joe's mom's basement (where receipts go to be judged and spreadsheets fear OG), this episode tackles two big questions Stackers are asking right now. What's the best tax software for filing your 2025 return? And what should normal, long term investors make of gold, silver, and crypto taking a wild ride?

Joe Saul-Sehy and OG are joined by Robert Farrington from The College Investor to break down the tax software landscape without the marketing fluff. Because if you're our Stacker avatar, you don't want hype. You want something that works, doesn't overcharge you, and doesn't suddenly upsell you because you clicked the wrong box.

Then in the headline segment, the crew digs into the sharp pullback in precious metals and crypto. Is this the beginning of something bigger? A buying opportunity? Or just another reminder that chasing shiny objects (literally shiny in gold's case) can make your portfolio feel like a roller coaster?

As always, Doug brings trivia, there's some basement banter, and the team separates smart strategy from financial fashion trends.

Choosing the Right Tax Software (Without Overpaying):

• Why FreeTaxUSA might be the best overall value for most Stackers

• When TurboTax or H&R Block make sense and when you're just paying for bells and whistles

• The pros and limitations of truly free options like Cash App Taxes and Chime

• Why TaxSlayer can be a solid choice for student loan borrowers, landlords, and side hustlers

• What investors and crypto traders need to know about brokerage imports and the new 1099-DA form

• Why filing taxes is mostly data entry and where real tax planning can make a difference

• Simple tools to track mileage, expenses, and side hustle income without losing your mind

Bottom line: the best software isn't universal. It's the one that fits your situation without surprise fees.

Gold, Silver, and Crypto: What the Drop Means:

• Why assets without earnings (like gold and many cryptocurrencies) can swing wildly

• The danger of investing based on FOMO instead of a plan

• How concentration risk increases the range of possible outcomes, both good and bad

• Why short term volatility doesn't automatically change a long term strategy

• The risks of misinformation, including AI generated financial advice that isn't real

OG walks through how disciplined investors think during volatile moments: zoom out, revisit your allocation, and stick to your strategy instead of reacting emotionally.

The Big Takeaway:

Whether you're picking tax software or deciding what to do during a market drop, the lesson is the same. Choose tools that fit your life. Build a plan before the chaos hits. Don't let headlines or shiny objects hijack your strategy.

This Episode Is For You If:

• You're trying to pick tax software without getting ripped off

• Markets are making you nervous and you're not sure if you should do something

• You want to understand what's happening with gold and crypto without the hype

• You're looking for calm, practical guidance during a chaotic time

• You believe steady wealth beats chasing shiny things

Let's Hear From You:

What tax software are you using this year and why? When markets get volatile, what helps you stay disciplined? Share your thoughts in the Spotify comments or The Basement Facebook group. Your experience might help another Stacker avoid an expensive mistake.

FULL SHOW NOTES: https://stackingbenjamins.com/the-best-tax-software-2026-robert-farrington-1805

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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