The Stacking Benjamins Show

Joe Saul-Sehy, OG, and Neighbor Doug pull up a rickety basement chair and unpack a growing trend: people treating investing like a series of high stakes bets instead of a long term plan. Sparked by a recent Wall Street Journal piece on aggressive investing, the gang digs into where the line is between smart risk taking and straight up gambling with your future.

Using plenty of real world examples and a few basement metaphors, the crew breaks down how stocks, businesses, options, and even so-called innovative products can fall into very different categories depending on why you're using them. The key theme? Good investing isn't about being bold. It's about understanding probabilities, controlling what you can, and stacking the odds in your favor over time.

Along the way, the team also tackles listener questions, including some strong feelings about Costco (because of course), and shines a flashlight into the dark corners of complex products like Indexed Universal Life insurance, explaining why "sounds sophisticated" doesn't always mean "fits your plan."

If markets feel noisy, confusing, or a little unhinged right now, this episode is your reminder that boring, disciplined strategies still win, and that you don't need to bet the farm to build one.

What You'll Learn:

• Why so many investors are confusing betting with investing right now

• How to tell the difference between calculated risk and speculation

• Why understanding probability matters more than chasing big wins

• Where options, businesses, and alternative investments can fit and where they often don't

• The hidden risks behind complex products like Indexed Universal Life (IUL) policies

• Why compounding beats hype even when headlines say otherwise

• How small, consistent decisions quietly outperform flashy moves

• Yes, what Costco has to do with smart money choices

This Episode Is For You If:

• Markets feel confusing and you're not sure if you're investing or just guessing

• You've been tempted by strategies that sound sophisticated but feel risky

• You want to understand the line between smart risk and gambling

• You're tired of flashy investment advice and want clarity on what actually works

• You need reassurance that boring, disciplined strategies still win

Question for You:

What's the riskiest financial move you've ever considered, and what stopped you (or didn't)? Share your answer in the Spotify comments or the Stacking Benjamins Facebook group. Bonus points if hindsight made you laugh or wince.

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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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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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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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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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