The Stacking Benjamins Show

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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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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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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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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