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StackingBenjamins.com | Cumulus Podcast Network

Named the Best Personal Finance Podcast by Bankrate.com and Kiplinger, The Stacking Benjamins Show features a light and friendly tone. Hosts Joe Saul-Sehy and OG aim to make financial literacy fun for all as they sit around the card table in Joe's Mom's half-finished basement and talk with experts about personal finance, saving, investing, and important money trends. As Fast Company once wrote, the Stacking Benjamins podcast "strikes a great balance of fun and functional." So join Joe and OG every Monday, Wednesday and Friday as they read your letters, discuss major headlines, and throw in some trivia and laughs for free.

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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When to Trust Your Gut and When to Trust the Math SB1795

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 Afford Life Without Living Like a Monk (SB1794)

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 Make Your Money Support the Life You Want (SB1793)

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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How to Prioritize Your Money: Listener Q&A (SB1792)

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

If you're making decent money but still feel like you're one bad month away from stress, this episode is for you.

Joe Saul-Sehy, OG, and Neighbor Doug sit down with Mel Abraham to talk about something most Stackers think about but don't know how to start: creating income that doesn't depend entirely on showing up to work every single day. Not side hustle mania or get-rich-quick schemes. Just practical ways to build what Mel calls a "money engine" that makes your financial life steadier and way less stressful.

Mel breaks down the different types of income streams, how they fit into real life (not just theory), and where to start if you're tired of feeling like your paycheck is the only thing keeping everything afloat. The goal isn't to quit your job tomorrow. It's to create options and breathing room so one surprise expense or career hiccup doesn't derail everything you've built.

Then Joe and OG tackle the January financial to-do lists that flood your inbox every year. You know the ones: "15 money moves to make before February!" They separate what's worth your time from what's just financial busywork designed to make you feel productive without moving the needle.

Because here's the truth. You don't need more financial homework. You need a few strategic moves that make 2026 feel more manageable from the start.

What You'll Walk Away With:

• How to think about building income beyond your paycheck without burning out

• The different types of income streams and which ones fit your actual life right now

• Where to start creating assets that work even when you're not clocking in

• Which January money tasks are worth doing and which ones waste your time

• How to prioritize your financial checklist for maximum impact with minimum stress

• Simple ways to organize your money for the year without it becoming a second job

This Episode Is For You If:

• You're making decent money but still feel financially stressed

• You want options beyond your paycheck but don't know where to start

• You're tired of feeling like everything depends on your next paycheck

• January financial advice usually overwhelms you more than it helps

• You want systems that reduce anxiety, not add more tasks to your list

Before You Hit Play, Ask Yourself:

What's one income stream you'd love to build if you knew it wouldn't be complicated? If you only had one hour this month to improve your finances, what would you spend it on? Drop your answers in the comments or the Basement Facebook group because Mel's framework plus Joe and OG's January reality check might be exactly what you need to start the year without the usual stress.

FULL SHOW NOTES: https://stackingbenjamins.com/build-your-money-engine-mel-abraham-1790

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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Build Income Beyond Your Paycheck (SB1790)

What if some of the "rules" you've been told about money aren't rules at all, just assumptions that haven't been questioned lately?

Joe Saul-Sehy, OG, and Neighbor Doug pull apart a handful of deeply held financial beliefs and see what holds up when real life enters the conversation. From Social Security timing to investment return expectations, the crew explores where common advice works, where it falls short, and why context matters more than catchy rules of thumb.

Along the way, the discussion shifts from spreadsheets to behavior, because knowing what to do is one thing and doing it (especially in retirement) is another. The team talks through spending realities, inflation anxiety, and how small mindset shifts can make your plan feel less fragile and more livable.

Then, just when things get serious, Doug introduces a challenge that's equal parts practical and revealing. The Survivor Pantry. It's a simple idea that uncovers how prepared (or not) we really are, and why preparedness isn't about fear but flexibility.

In This Episode You'll Explore:

• Why popular Social Security advice isn't one size fits all

• What real world investment returns look like over time

• How behavioral blind spots can derail otherwise solid plans

• The difference between planning for retirement and living in it

• Smarter ways to think about spending as prices change

• Why some financial myths refuse to die (and how to spot them)

• What the Survivor Pantry reveals about readiness and resilience

• How questioning assumptions can lead to calmer, more confident decisions

This episode is less about finding new answers and more about asking better questions, especially if you're tired of feeling like you're "behind" for not following every money rule to the letter.

Conversation Starter for the Basement:

What's one money belief you've always accepted but now you're not so sure about? Drop your thoughts in the Facebook group or comments and compare notes with other Stackers who are rethinking the playbook right alongside you.

FULL SHOW NOTES: https://stackingbenjamins.com/challenging-money-assumptions-1789

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!
Learn more about your ad choices. Visit podcastchoices.com/adchoices

Breaking Money Rules and Playing Survivor Pantry SB1789

It's that time of year when we look ahead, squint confidently into the future, and pretend we have any idea what's coming next. In this annual Stacking Benjamins tradition, Joe Saul-Sehy welcomes back Mindy Jensen from the BiggerPockets Money Podcast, Len Penzo of LenPenzo.com, and OG for the predictions episode that blends money talk, pop culture, and just enough nonsense to keep everyone honest.

Instead of pretending anyone can forecast the markets, the crew leans into what really matters: how to think about uncertainty. With help from a Magic 8 Ball (clearly the most reliable forecasting tool available), the panel throws out bold guesses about stocks, crypto, AI, inflation, interest rates, and the kinds of headlines that will dominate conversations in 2026. Some predictions are financial. Some are cultural. Some are optimistic, let's say.

But beneath the fun is a useful reminder for Stackers. Predictions don't build wealth, process does. This episode isn't about acting on guesses. It's about stress-testing assumptions, questioning narratives, and remembering that long-term success comes from good habits, not crystal balls. If you've ever wondered how much attention to pay to forecasts (and how much to ignore), this conversation delivers clarity wrapped in entertainment.

And yes, there are sports predictions, celebrity guesses, and enough wild speculation to guarantee at least a few laughs when we look back a year from now.

In This Episode You'll Hear:

 The crew's biggest financial and cultural predictions for 2026

 What the Magic 8 Ball "thinks" about markets, rates, and inflation

 Why forecasts are fun but dangerous if taken too seriously

 Thoughts on AI, energy use, and how technology may affect daily life

 Predictions about crypto, gold, and the stories investors love to chase

 A reminder of what matters when markets surprise everyone

 Sports, pop culture, and wildly specific guesses that will age somehow

Join the Conversation:

Which prediction do you think has the best chance of being right, and which one will age the worst? Share your take in Spotify comments or the Basement Facebook group so we can revisit it next year and keep receipts.

This episode is a reminder that while nobody knows what 2026 will bring, Stackers who stay curious, flexible, and grounded tend to do just fine. Magic 8 Ball or not.

FULL SHOW NOTES: https://www.stackingbenjamins.com/magic-8-ball-and-2026-predictions-1788/

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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Our Annual Magic 8 Ball Predictions for 2026 (SB1788)

If 2026 already feels busy and it's barely started, you're not imagining it. Joe Saul-Sehy and OG sit down with renowned time management expert Laura Vanderkam to tackle one of the biggest stressors Stackers face. Feeling like there's never enough time to do the things that matter, including managing money well.

Laura helps break the myth that better time management means squeezing more productivity into already packed days. Instead, the conversation centers on intentional time use: how to protect space for what matters most, reduce decision fatigue, and build simple systems that make life (and money) feel lighter. If you've ever said "I don't have time to deal with this right now" about your finances, this discussion will feel uncomfortably familiar in a good way.

From there, the show zooms out just enough to connect time decisions to money decisions. Joe and OG explore why financial stress often comes from neglect rather than bad choices, and how a few well-timed actions (like organizing documents, planning ahead for aging parents, or setting aside focused "money time") can prevent massive headaches later. No doom and gloom economics here, just a reminder that uncertainty is always around and preparation beats prediction every time.

The episode also takes a thoughtful turn toward caregiving and elder planning, a topic many Stackers are quietly juggling while managing careers, kids, and their own goals. Laura and the team talk about how planning before a crisis saves not just money but emotional energy, one of the most overlooked resources of all.

This is a conversation about doing less reacting, more choosing, and building a 2026 where your calendar and your bank account work together.

What You'll Hear:

• Why "being busy" isn't the same as using time well

• Laura Vanderkam's practical strategies for reclaiming focus and presence

• How small pockets of time ("time confetti") quietly drain energy

• Simple ways to create space for money decisions without overwhelm

• Why procrastinating financial tasks often costs more than bad investing

• How to think ahead about caregiving without panic or perfection

• What documents and conversations make future decisions easier

• How to prepare for uncertainty without obsessing over headlines

If you want to start 2026 feeling more in control (not just of your money but of your life), this episode offers a grounded, encouraging roadmap. No hustle culture. No financial fear tactics. Just smart conversations about using your time wisely so your money decisions get easier, not harder.

Listen for the moment when "I don't have time" turns into "I'm choosing what matters."

FULL SHOW NOTES: https://stackingbenjamins.com/master-your-time-management-with-laura-vanderkam-1787

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!
Learn more about your ad choices. Visit podcastchoices.com/adchoices

Making Time for What Matters with Laura Vanderkam (SB1787)

A new year has arrived, and with it comes a fresh wave of hot takes, bold predictions, and "can't miss" investing ideas. Joe Saul-Sehy and OG step back from the noise to discuss what clearly doesn't work and then to focus on what actually helps you build wealth in 2026 and beyond.

Rather than chasing hot trends, they revisit the timeless rules that have quietly done the heavy lifting through every market cycle. Why diversification still matters even when it feels boring. Why IPO hype and speculative real estate deals often disappoint. How consistency beats cleverness far more often than most people expect.

From there, the conversation shifts into a practical framework Stackers can use no matter what the market throws their way. Joe and OG walk through the proper order of investing decisions: start with clear goals, build the right asset allocation, choose appropriate asset selections, and then layer in tax strategy. By putting taxes in the right place (after the big structural decisions), they explain how to improve outcomes without letting tax avoidance distort the entire plan.

The episode also digs into real-world traps that tend to surface when uncertainty rises. Real estate crowdfunding. Penny stock temptation. Misunderstood property tax increases. The guys break down where people get tripped up and how to protect yourself without becoming overly cautious or frozen by fear.

Just as important, Joe and OG explore the difference between luck and skill in investing stories. If you've ever felt behind because someone else's risky move worked out, this discussion brings perspective and relief by reminding Stackers what sustainable progress actually looks like.

What You'll Learn:

• Why timeless investing principles matter more than 2026 predictions

• How diversification truly reduces risk and where people misuse it

• The dangers of IPOs, penny stocks, and "exclusive" real estate deals

• The correct order of smart investing decisions: goals first, asset allocation next, asset selection after that, tax strategy layered on last

• How to think about tax efficiency without letting taxes drive the plan

• What new homeowners often misunderstand about property taxes

• How to spot luck masquerading as skill in investing success stories

• Ways to stay confident and consistent when markets feel uncertain

If you're looking to start 2026 grounded, informed, and focused on the moves that actually matter, this episode delivers a steady, practical roadmap without hype, fear, or shortcuts.

Listen for the principles that hold up when markets misbehave and the small mistakes that quietly derail otherwise solid plans.

FULL SHOW NOTES: https://stackingbenjamins.com/real-estate-scam-companies-1786

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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Waste Time on Hot Real Estate or IPO Trends or Start Building Wealth? SB1786

Have you had trouble getting the people around you to understand the importance of saving, investing, and planning? Maybe you're having trouble connecting with people on their level or it's difficult to have a meaningful, lasting conversation? Worse yet, and on a much wider scope...maybe you don't understand current events and why things are happening. Today we dive into a piece from the Harvard Business Review that suggests there's a key piece that could be missing in your relationships: curiosity. Our roundtable will help us figure out the why behind your questions about what others are doing...and includes our friend from the financial blog Tread Lightly, Retire Early, Angela Rozmyn; Len Penzo from the LenPenzo.com blog, and our very own OG.
After our awesome (if we don't say so ourselves...) empathy discussion, we'll give our roundtable a break while we chat with the founder of a new money-tracking solution. Between breaking your spending down into searchable categories, automatic bill and subscription detection, and budget capabilities, the Copilot app has a lot going for it. We'll chat with founder Andres Ugarte during our Friday Fintech segment to get the inside scoop.
Plus, do you remember the first time you had to buy home essentials on your own? ("What??? Bacon cost THAT much!?") During our MagnifyMoney segment, we'll dive into some of the responses to our Twitter poll: What’s something you didn’t realize how expensive it was until you had to start buying it yourself? Here's one from the home team: shredded cheese (more than I thought it would cost anyway), cleaning supplies, and of course... going out to eat multiple times a week. KA-CHING! 
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Your Friends Suck At Money? Here's What To Do.

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