The Stacking Benjamins Show

Latest Episodes:

The Worst Money Advice Ever (Episode 1800!) Feb 06, 2026

Show notes

Eighteen hundred episodes calls for something special, and what better way to celebrate than by dragging the absolute worst money advice into the light and laughing at it together?

Special guest and CFP Sarah Catherine Guiterrez from Aptus Financial joins Joe Saul-Sehy, Neighbor Doug, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long Term Investors) for a rapid-fire, no mercy takedown of the most damaging financial clichés ever passed down at family dinners, car dealerships, and internet comment sections.

This episode is equal parts group therapy, myth-busting, and friendly argument. Exactly the kind of chaos that's kept the Stacking Benjamins basement standing for 1,800 shows.

What You'll Hear in This Milestone Episode:

• The most cringeworthy financial advice the panel has ever heard and why it sticks around

• Why phrases like "just let the bank take it" quietly wreck long-term wealth

• How YOLO thinking sneaks into financial decisions disguised as confidence

• The difference between common advice and useful advice

• Sarah Catherine's planner level perspective on why bad advice feels comforting

• Paula and Jesse sparring over long term thinking versus short term emotion

• OG bringing strategy, clarity, and the occasional eye roll

• Neighbor Doug doing what he does best: poking holes, cracking jokes, and keeping everyone honest

• Why car buying advice is one of the most misunderstood areas in personal finance

• How trivia, travel, and history collide in a surprisingly competitive game segment

• What Singapore's founding teaches us about perspective, patience, and getting the facts right

• Why smart money decisions usually sound boring but work anyway

This Episode Is For You If:

• You've ever heard money advice and thought, "Wait, people actually believe that?"

• You're tired of conflicting financial wisdom and want validation that some of it IS terrible

• You've been burned by advice that sounded good but cost you money

• You want to hear smart people argue about what actually works versus what just sounds good

• You've been with us since episode 1, or just wandered into the basement and want to celebrate

This episode is a love letter to Stackers who question conventional wisdom and trust their gut when advice doesn't add up. It's loud, opinionated, funny, and packed with reminders that the best financial moves often start by ignoring the advice everyone else is shouting.

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Building a Wealth Machine That Lasts Generations (SB1799) Feb 04, 2026

Show notes

Whitney Elkins-Hutten's story isn't about overnight success or getting lucky. It's about building a wealth machine that keeps working even when life throws curveballs.

Broadcast as always from Joe's mom's basement, this episode explores how Whitney went from a modest, very 1970s upbringing to creating systems that generate lasting wealth, and what everyday people can realistically take from her experience. Yes, she built an $800 million real estate portfolio, but this conversation is about something bigger: how to create income systems that compound, scale, and eventually run without you.

Along the way, Joe Saul-Sehy, OG, and Doug connect the dots between mindset, cash flow strategies, and protecting what you've already built in a world full of digital landmines.

What You'll Take Away:

• Why Whitney's early mistakes became her biggest long term advantages

• How to think about building cash flow engines, not just accumulating assets

• The difference between owning things and building repeatable income systems

• Why passive income still requires intentional structure and where people go wrong

• How mentorship accelerates progress and what to look for in the right mentor

• Practical ways to get started building wealth systems without massive capital

• Why diversification across income streams matters more than most people realize

• What unexpected businesses like car washes teach us about operational efficiency

• How subscription models and recurring revenue quietly stabilize cash flow

• The long game of turning short term decisions into generational wealth

• Why protecting your personal data is now part of protecting your net worth

• How small habits (financial and otherwise) compound into outsized results

This Episode Is For You If:

• You want to build wealth that lasts beyond your lifetime

• You're curious about creating income systems that don't require your constant attention

• You're tired of overnight success stories and want the real trajectory

• You're looking for principles that work whether you invest in real estate, businesses, or other assets

• You believe smart systems and consistent learning can change your family's financial future

This episode is for Stackers who want proof that progress doesn't require perfection, and that building the right wealth machine can change the entire trajectory of your financial life and your family's future.

FULL SHOW NOTES: https://stackingbenjamins.com/building-generational-wealth-with-whitney-elkins-hutten-1799

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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Stop Leaving Money on the Table at Tax Time (SB1798) Feb 02, 2026

Show notes

Taxes don't have to feel like something that happens to you.

Joe Saul-Sehy, OG, and Neighbor Doug break down the biggest recent tax changes and, more importantly, how to use them intentionally instead of accidentally leaving money on the table.

This isn't about memorizing the tax code or becoming a DIY CPA. It's about understanding where the real opportunities are right now, which moves matter most at different life stages, and how smart planning today can quietly add up to thousands of dollars over time.

From new deductions to retirement-focused strategies, this episode helps you move from reacting at tax time to planning all year long.

What You'll Learn:

• The most important recent tax changes and who actually benefits from them

• How the expanded SALT deduction works and when it matters

• What the new senior deduction could mean for retirees and near retirees

• Why maximizing retirement accounts isn't just about saving for later but lowering taxes now

• How Health Savings Accounts create one of the most powerful tax advantages available

• When tax loss harvesting helps and when it's mostly noise

• Why managing your tax bracket in retirement can be as important as investment returns

• Smarter charitable giving strategies that align generosity with tax efficiency

• How education savings tools fit into a broader tax plan for those who need them

• Common tax season mistakes that quietly cost people money every year

This Episode Is For You If:

• You suspect you're paying more in taxes than you should

• Tax planning feels overwhelming so you just deal with it in April

• You want to understand which tax moves actually matter at your life stage

• You're tired of hearing about strategies that don't apply to your situation

• You're ready to stop reacting to taxes and start planning for them

This episode is for anyone who wants their tax strategy to support their bigger financial goals, not work against them. If you're looking to keep more of what you earn and make fewer "wish I'd known that earlier" decisions, this is one to queue up.

FULL SHOW NOTES: https://stackingbenjamins.com/tax_planning_moves_for_2026-1798

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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How to Get 1% Better Without Burning Out (SB1797) Jan 30, 2026

Show notes

What if the path to better money decisions, more confidence, and a calmer life wasn't a massive overhaul but just getting a tiny bit better today than you were yesterday?

Joe Saul-Sehy, Neighbor Doug, OG, and Paula Pant (Afford Anything) are joined by David Gillis, creator of the 1% Better Conference, for a roundtable exploring the surprisingly powerful idea of improving by just 1% at a time. No vision boards. No 5 a.m. ice baths. Just small, intentional choices that compound into real results, financially and otherwise.

David brings practical insight and zero guru energy into what sustainable improvement looks like. Together the group talks about why most people burn out trying to change everything at once, and how Stackers can instead design days that make better decisions easier.

You'll hear honest conversations about energy drainers (including the ones we pretend aren't draining), why saying "no" is often the most underrated financial skill, and how rest, relationships, and even boredom play a bigger role in success than grinding ever will. There's also a healthy reminder that progress doesn't always look productive, and that's okay.

As always, Doug brings the trivia, the basement brings the banter, and the lesson sneaks up on you when you're not looking.

If you've ever felt like you should be doing more but don't want to torch your sanity getting there, this episode is for you.

If the 1% Better philosophy resonates with you, the 1% Better Conference is happening February 21-22 in Omaha, where Joe will be the keynote speaker.

What You'll Learn:

Why 1% better beats "start over Monday" every single time
How to identify the biggest energy leaks hurting your money decisions
Why learning to say "no" can improve your finances immediately
How rest, nature, and relationships quietly boost long term success
Why small habits matter more than motivation
How to grow personally and financially without burning out
A realistic framework for steady improvement that fits real life

This Episode Is For You If:

You're exhausted from trying to overhaul everything at once
You feel like you should be doing more but you're already maxed out
You want progress that doesn't require torching your current life
You're tired of all or nothing approaches that leave you burnt out
You're ready for sustainable improvement instead of another failed fresh start

Question for You:

What's one small change you could make this week that would make your life or money just a little easier? Drop it in the comments or share it with us in the Basement Facebook group. We promise not to turn it into a 30 day challenge with a workbook.

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The Science of Better Ideas with George Newman SB1796 Jan 28, 2026

Show notes

Where do great ideas come from, and why do they always show up in the shower, on a walk, or five minutes after you've stopped trying so hard?

Joe Saul-Sehy, OG, and Neighbor Doug welcome this week's mentor, behavioral scientist George Newman, to unpack how creativity really works and how Stackers can use it to make better decisions with money, careers, and life.

This isn't about becoming "more creative" in a woo-woo sense. It's about understanding the conditions that consistently produce better ideas. George explains why your best thinking doesn't come from grinding harder but from combining curiosity, expertise, and space to think. The crew digs into why incremental improvement (the famous "1% better" mindset) often beats chasing giant breakthroughs, and how that approach applies just as well to financial planning as it does to business, habits, or personal growth.

You'll also hear why surveying the landscape before acting leads to smarter money moves, how relaxing your brain can unlock solutions you didn't know you had, and why most people already have access to better ideas but don't recognize them yet. Whether you're trying to improve your finances, rethink your career, or simply stop overthinking every decision, this episode gives you a practical framework for generating smarter ideas without burning yourself out.

What You'll Learn:

Where great ideas are most likely to come from (hint: not when you're stressed)
Why expertise plus curiosity beats raw inspiration every time
How the 1% better philosophy creates long term breakthroughs
The role relaxation plays in clearer thinking and decision making
Why surveying your options first leads to better financial outcomes
How small experiments like paper trading improve confidence before real world action
Why coaching, reflection, and time horizons matter more than quick wins

This Episode Is For You If:

You feel like you're working harder but not thinking better
Your best ideas come when you're NOT trying to force them
You're exhausted from grinding and want a smarter approach
You want to improve your finances but feel stuck in the same patterns
You're ready to stop chasing breakthroughs and start making steady progress

Questions to Think About:

When do your best ideas usually show up, and what are you doing when they arrive? What's one area of your finances that could improve with a "1% better" mindset? Drop your answers in the comments or the Basement Facebook group because George's framework for generating better ideas might shift how you approach everything.

FULL SHOW NOTES: https://stackingbenjamins.com/where-do-your-best-ideas-come-from-1796

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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When to Trust Your Gut and When to Trust the Math SB1795 Jan 26, 2026

Show notes

Ever made a money move that felt right then immediately wondered if you just emotionally invested in a bad idea? We've all done it. Some of us have receipts.

Joe Saul-Sehy, OG, and Neighbor Doug tackle one of the trickiest parts of personal finance: knowing when to trust your gut and when your gut needs to sit down and let the math speak.

Because here's the thing. Most Stackers aren't struggling because they don't know what a Roth IRA is. You're struggling because real life decisions don't happen in a spreadsheet. They happen in the middle of a busy Tuesday, with a dozen tabs open in your brain and a million little "what ifs" fighting for attention. So the guys dig into how intuition works (and when it betrays you), and why data is powerful until you start using it to talk yourself into doing something dumb with extra steps.

You'll also hear how the best financial plans aren't built on perfect predictions but on repeatable decisions. Plus the episode veers into some surprisingly useful territory with Costco membership strategy, the hidden psychology of "good deals," and how advisors use tools to help optimize Social Security choices without making you feel like you need a PhD in government paperwork.

What You'll Learn:

How to tell the difference between good intuition and financial anxiety in a trench coat
Why data can be a superpower or a weapon you use against yourself
The role of AI and research in decision making and what it means for everyday people
How OG thinks about sticking to a plan when emotions get loud
Why "a deal" can be a budget win or a trap door
What a Costco membership is really doing to your spending habits
The Social Security optimization tools advisors use and why timing decisions matter

This Episode Is For You If:

You've made emotional money decisions you later regretted
You either overthink every financial choice or jump too fast without enough info
You're not sure when to trust your instincts versus when to run the numbers
You want to make confident decisions without needing perfect information
You're tired of second guessing yourself every time money is involved

Questions to Think About:

When was the last time your gut feeling saved you financially or cost you money? Are you more likely to overthink decisions with too much research or jump too fast without enough? Drop your answers in the comments or the Basement Facebook group because finding your balance between intuition and data might be the unlock you need.

FULL SHOW NOTES: https://stackingbenjamins.com/should-you-trust-your-gut-or-data-1795

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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How to Afford Life Without Living Like a Monk (SB1794) Jan 23, 2026

Show notes

Inflation may be doing its best to body slam your budget, but this episode is all about fighting back without turning your life into a sad spreadsheet.

Joe Saul-Sehy, Neighbor Doug, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long Term Investors) are joined by special guest Justin Brown-Woods (Price of Avocado Toast) for a roundtable tackling the big question Stackers keep asking: Why does life feel so expensive even when I'm doing everything right?

Instead of the usual "just cut lattes" advice, the crew digs into what's really happening. How to calm chaotic expenses. How to stop getting ambushed by "random" costs that aren't random. How to build a plan that makes your money feel predictable again.

The conversation hits the real pressure points: food, housing, subscriptions, and the sneaky spending that doesn't look dangerous until it adds up. If you've ever looked at your bank account and thought "Wait, where did that go?" this episode will help you spot the leaks, tighten the system, and still enjoy your life while you do it.

What You'll Learn:

• How to stop chaotic expenses from wrecking your month

• The difference between fixed and variable spending, and why it matters more than you think

• Practical ways to lower food costs without eating sadness for dinner

• Why housing is the heavyweight champion of your budget and what to do about it

• How subscriptions quietly drain cash even when you barely use them

• The best way to cut costs without feeling punished

• Why mandatory expenses are often more negotiable than you've been told

This Episode Is For You If:

• You feel like you're doing everything right but still barely keeping up

• Your bank account keeps surprising you with where the money goes

• You're tired of frugality advice that makes life feel like punishment

• You want to cut costs without giving up everything that makes life worth living

• You're ready to calm the chaos and make your spending feel predictable again

Questions to Think About:

What's one expense that used to feel normal but now feels completely ridiculous? Which category gets you more: food spending, housing, or the sneaky monthly subscriptions? Drop your answers in the comments or the Basement Facebook group because this roundtable's framework for taming chaotic spending might be exactly what you need.

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-afford-the-new-normal-1794

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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How to Make Your Money Support the Life You Want (SB1793) Jan 21, 2026

Show notes

What if your money stopped dictating your schedule and started supporting the life you actually want to live?

Joe Saul-Sehy welcomes CFP Dana Anspach of Sensible Money as special guest co-host for an episode featuring this week's mentor, Andy Hill. Andy shares how he stepped away from the corporate grind, redesigned his priorities, and built a life where family and flexibility came first. His story isn't about escaping work. It's about building a financial foundation that gives you options.

Then the conversation shifts to a headline that caught everyone's attention: NASCAR driver Kyle Busch and his wife Samantha are suing their insurance company, calling the life insurance they purchased "a scam." Dana uses this case to break down one of the most misunderstood areas in personal finance: life insurance. From Indexed Universal Life (IUL) policies to knowing when insurance is a tool and when it's a distraction, she shows how clarity of goals should drive every decision and how to avoid the traps that caught even high earners like the Buschs.

The episode also touches on estate planning, scams to watch out for, how young adults should think about budgeting and debt, and how to evaluate whether paying off loans or investing is the better move for your situation. It connects the dots between time freedom, smart planning, and protecting what you're building.

What You'll Learn:

• How to design your finances around the life you want, not just the paycheck you earn

• What "owning your time" really means and how to start moving in that direction

• Why your financial plan should begin with values and priorities, not products

• How to think about entrepreneurship without blowing up your financial stability

• What the Kyle Busch insurance lawsuit reveals about life insurance products and sales tactics

• The truth about Indexed Universal Life insurance and when it may or may not make sense

• How to evaluate life insurance based on goals instead of sales pitches

• How estate planning protects your family and your legacy

• The pros and cons of paying off loans versus investing

• Budgeting principles that help young adults build strong money habits early

• How to recognize and avoid financial scams (including insurance product traps)

• Why celebrating progress matters just as much as setting the next goal

This Episode Is For You If:

• You feel like your money controls your life instead of supporting it

• You want more flexibility and time freedom but don't know how to fund it

• You're confused about whether life insurance products are helping or just costing you (especially after hearing about the Busch lawsuit)

• You're trying to figure out the right order of financial moves (debt vs investing, insurance vs saving)

• You want your financial plan to reflect your actual values, not just what you're "supposed" to do

This episode is about aligning your money with your life. If you're ready to stop reacting to your finances and start using them to build more freedom, flexibility, and confidence, this one belongs at the top of your queue.

FULL SHOW NOTES: https://stackingbenjamins.com/own-your-time-with-andy-hill-and-dana-anspach-1793

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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How to Prioritize Your Money: Listener Q&A (SB1792) Jan 19, 2026

Show notes

Ever feel like your money questions don't fit neatly into one category? One minute you're thinking about retirement, the next it's insurance, emergency funds, gifting money, or whether your workplace plan is helping or hurting you.

This is one of those episodes where Stackers bring the real-life questions, and Joe Saul-Sehy, CFP Anna Allem, and Neighbor Doug help sort through the noise. It's a true Q&A show built from the issues you're wrestling with right now. No perfect spreadsheets. No one-size-fits-all answers. Just practical guidance for making smart decisions when your financial life has a lot of moving parts.

You'll hear how to prioritize when everything feels important, how to adjust your strategy as rules change, and how to stay flexible without losing control of your long-term plan. College planning comes up, but it's part of a bigger conversation about balancing competing goals, not the center of the episode.

What You'll Learn:

• How to make better decisions when multiple financial priorities collide

• Smarter ways to think about life insurance when cash flow feels tight

• How to build or rebuild an emergency fund with inconsistent income

• What changes to 401(k) rules could mean for your saving and investing strategy

• When opting out of a workplace plan might make sense, and when it's a mistake

• How automatic enrollment and contribution changes can impact your future wealth

• The right way to gift money to kids or grandkids without creating tax or planning problems

• How HSAs fit into your bigger financial picture

• Why financial gridlock happens and how to break through it

• How to balance short term flexibility with long term security

• A clear explanation of FAFSA and financial aid, and how it fits into overall planning for families who need it

This Episode Is For You If:

• You're juggling multiple financial priorities and not sure which one to tackle first

• You feel stuck because everything seems important and nothing feels urgent enough

• You want guidance that fits your messy real life, not just textbook answers

• You're tired of financial advice that assumes you only have one problem at a time

• You need permission to prioritize imperfectly and still make progress

If your finances feel like a maze, this is your map.

FULL SHOW NOTES: https://stackingbenjamins.com/answering-stacker-questions-with-anna-allem-1792

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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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

The Money Habits to Keep and Ditch in 2026 (SB1791) Jan 16, 2026

Show notes

Some people kick off a new year with a vision board. We prefer a runway show in sweatpants from Joe's mom's basement.

Joe Saul-Sehy, OG, and Neighbor Doug throw personal finance into the spotlight and ask the question every Stacker secretly loves: What's officially "so last year" in your money plan, and what's worth keeping for 2026?

Because here's the truth. You don't need a total financial makeover. You need a few smart "wardrobe swaps" that fit your real life. The habits that quietly drain your progress (hello, lifestyle creep). The stuff people obsess over that doesn't matter as much as they think. And the overlooked moves that make everything else easier.

The crew breaks down what's out (financial habits that looked good but never delivered), what's in (the practical moves that reduce stress and create actual progress), and why real financial planning isn't just about investments but about building a system that holds up when life gets messy.

Also on the docket: a fresh start to the yearlong trivia competition with new rules, new twists, and the kind of competitive energy that makes you wonder if the trophy comes with a safety warning label.

What You'll Learn:

• What financial trends are out for 2026 and why they weren't helping anyway

• The habits that are in if you want more freedom, less stress, and fewer "where did my money go" moments

• Why real financial planning isn't just investments but a system that works in real life

• How lifestyle creep sneaks in and a couple ways to stop it before it becomes your full-time hobby

• What tax strategy means for normal people, not just spreadsheet enthusiasts

• The money conversations you should have early in the year before life gets loud again

• A realistic take on housing in 2026 and what to focus on when markets don't behave

• New trivia rules including a twist that changes everything if you're not paying attention

This Episode Is For You If:

• You want to know what to stop doing so you can focus on what works

• You're tired of financial advice that adds more tasks instead of clarity

• You suspect some of your money habits aren't pulling their weight

• You want permission to quit the financial trends that never fit your life

• You're ready for a few strategic changes that make 2026 feel more manageable

Questions to Think About:

What's one money habit you're officially retiring in 2026? If you could upgrade one part of your financial plan this year, what would it be: spending, saving, investing, insurance, or taxes? Drop your answers in the comments or the Basement Facebook group because this episode is all about figuring out what stays and what goes.

FULL SHOW NOTES: https://stackingbenjamins.com/finance-hot-or-not-2026-1791

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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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.