The Stacking Benjamins Show

What's more romantic than roses and chocolate? How about not fighting about money.

Joe Saul-Sehy and OG welcome Douglas and Heather Boneparth, the financial planning power couple who literally wrote the book on navigating money in relationships. Broadcasting from the basement (where love is patient and spreadsheets are kind), the crew dives into how people can build financial trust, avoid money secrets, and actually enjoy talking about dollars without it turning into a heavyweight title fight.

Whether you're navigating finances with a romantic partner, a roommate splitting rent, an accountability partner keeping you honest, or a family member you're in business with, these principles apply. Because let's face it: our Stacker avatar isn't trying to impress Wall Street. You're trying to build a great life with the people who matter, without money becoming the thing that creates tension.

Douglas and Heather break down what healthy financial communication really looks like, how to spot and prevent financial secrecy, and why shared goals matter more than perfectly matched spending styles. They also tackle the tricky stuff: different money upbringings, emotional baggage around finances, and how to reset when conversations go sideways.

And since this is the basement, you'll also get practical reminders about key financial deadlines (because nothing kills momentum like IRS penalties), smart ways to teach kids about money, and Doug's festive trivia to keep things light.

What You'll Learn:

How to talk about money without it escalating into a debate or argument

The warning signs of financial secrecy and how to prevent it in any relationship

Why shared goals matter more than identical personalities or spending styles

Practical ways to align spending, saving, and investing with another person

How your childhood money experiences shape your adult financial behavior

Smart ways to teach kids patience, work reward connections, and intentional spending

Important financial deadlines to keep on your radar

Why communication, not math, is often the real key to financial success

This Episode Is For You If:

You avoid money conversations because they always seem to go badly

You're navigating shared finances with a partner, roommate, or family member

You want to align financial goals with someone without constant friction

You're single but have accountability partners or friends you talk money with

You believe better communication is the key to better financial outcomes

Question for You:

What's one money conversation that felt awkward at first but ultimately made a relationship (romantic, friendship, or otherwise) stronger? Drop your answer in the Spotify comments or the Stacking Benjamins Facebook group. You might just help another Stacker start a better conversation.

Because in the end, mastering money isn't just about returns. It's about building a life and relationships that work.

FULL SHOW NOTES: https://stackingbenjamins.com/relationships-and-money-with-doug-and-heather-boneparth-1802

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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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