The Stacking Benjamins Show

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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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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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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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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