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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

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!
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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

What if earning more money in 2025 has less to do with working longer hours and more to do with becoming dangerously useful?

In this conversation, Joe Saul-Sehy and OG sit down with entrepreneur Alex Hormozi to break down how skill stacking, leverage, and better decision-making can radically change your income trajectory, whether you run a business, lead a team, or clock in for a 9-to-5.

Alex pulls back the curtain on what actually drives higher pay: choosing the right skills, focusing on work that compounds, and learning how to take smart risks without blowing up your life. Along the way, he tackles one of the hardest challenges Stackers face, how to pursue growth when well-meaning friends, family, or coworkers are urging you to play it safe.

This isn't about hustle culture or quitting your job tomorrow. It's about building a skill set that makes you indispensable, learning how to negotiate from a position of strength, and thinking long-term while others stay stuck optimizing small things.

WHAT YOU'LL TAKE AWAY:

 Why skill stacking beats talent when it comes to earning power

 How to identify high-leverage skills that pay off in any career

 Ways to invest in yourself that don't require an MBA or massive risk

 How to apply entrepreneurial thinking inside a traditional job

 Practical negotiation insights that actually work in the real world

 When giving away value helps you grow and when it backfires

 How to tune out discouraging advice without burning bridges

 Why systems and processes matter more than motivation

If you're serious about earning more in 2025 but want to do it thoughtfully, sustainably, and on your own terms, this episode gives you a blueprint worth studying.

Listen for the mindset shifts that compound quietly and the small changes that can unlock much bigger opportunities over time.

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Alex Hormozi on Skills That Actually Build Wealth, Part 2 (SB1785)

What if the biggest driver of your financial future isn't the stock market but your skill set?

In this episode of The Stacking Benjamins Show, Joe Saul-Sehy and the crew sit down with entrepreneur and business strategist Alex Hormozi to unpack one of the most overlooked wealth-building tools Stackers have access to: skill acquisition.

Alex doesn't pitch get-rich-quick nonsense or risky moonshots. Instead, he walks through how ordinary people (employees, side hustlers, and business owners alike) can increase their income by focusing on high-leverage skills, smarter negotiations, and taking calculated risks that actually make sense.

You'll hear how Alex went through early business struggles and hard-earned lessons before building real wealth. Not by chasing trends, but by deliberately stacking skills, learning faster than the competition, and betting on himself without blowing up his life. The lessons apply whether you're asking for a raise, switching careers, growing a side hustle, or simply trying to earn more without working yourself into the ground.

This is an episode about earning more on purpose, not grinding harder.

WHAT TO LISTEN FOR:

 Why skill-building often beats investing early in your career

 How to identify high-leverage skills that pay off repeatedly

 The difference between smart risk and reckless risk

 Why small optimizations won't change your life but big skills might

 How to design your own curriculum without going back to school

 When betting on yourself actually makes financial sense

ALSO IN THIS EPISODE:
Reflecting on standout episodes from 2025 and what's coming next, a quick check-in on managing your money with intention not noise, why confidence is built through reps not motivation, and how compensation and risk are more connected than you think.

A QUESTION FOR THE BASEMENT:
What's one skill you've learned that's paid off way more than you expected, or one you wish you'd started earlier? Share it in Spotify comments or bring it to the Basement Facebook group. Your answer might help another Stacker spot their next big opportunity.

Because money grows in accounts, but wealth starts with what you can do.

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Alex Hormozi on Skills That Actually Build Wealth SB1784

New year, clean slate, and maybe time for a closer look at the person managing your money.

Joe Saul-Sehy and OG kick off 2026 by answering the question many Stackers quietly wonder about: Is my financial advisor actually good at their job?

Rather than talking theory or credentials, they break down five real-world red flags that signal an advisor might be more focused on products, commissions, or their own ego than on your goals. These are the subtle warning signs you'll never see in a glossy brochure but you'll absolutely feel over time.

The 5 red flags:
• Poor communication that keeps you in the dark
• Office culture that feels off
• Confusing jargon (often a feature, not a bug)
• Unclear or hidden fees
• Products over process

Plus: Doug's Italian food trivia, New Year's breakfast burrito chaos, and a reminder that you're allowed to expect clarity and respect.

Question for you: What's the biggest green flag or red flag you've seen from a financial advisor? Share in the comments—your story might help another Stacker avoid a costly mistake.

The Red Flags Your Financial Advisor Hopes You Miss

New year, clean slate, and maybe a closer look at the person helping you manage your money.

In this episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG kick off the year by pulling back the curtain on a question many Stackers quietly wonder about: Is my financial advisor actually good at their job?

Rather than talking theory or credentials, the guys break down five real-world red flags that signal an advisor might be more focused on products, commissions, or their own ego than on your goals. These are the subtle warning signs you'll never see in a glossy brochure but you'll absolutely feel them over time.

From how an advisor communicates (or doesn't), to what their office culture tells you, to why confusing jargon is often a feature not a bug, this episode gives you practical ways to evaluate whether your advisor is truly on your team.

And because this is Stacking Benjamins, the serious stuff is balanced with laughs, a little New Year's chaos, and Doug's trivia detour into Italian food.

If you've ever wondered whether you should stay, ask better questions, or quietly run for the exit, this episode gives you the confidence to decide.

WHAT YOU'LL LEARN:

 The top five red flags that signal a subpar financial advisor

 Why great advisors focus on process and goals, not hot products

 How poor communication quietly sabotages your financial progress

 What an advisor's office environment and staff behavior can reveal

 Why unclear fees and excessive jargon should make you nervous

 How to check public records without feeling overwhelmed

ALSO IN THIS EPISODE:
A fresh start to the year with breakfast burritos, Doug's trivia break on Italian food, a reminder that you are allowed to expect clarity and respect, plus community updates and what's coming next.

HERE'S A QUESTION TO THINK ABOUT:
What's the biggest green flag or red flag you've seen from a financial advisor? Share your experience in Spotify comments or bring it to the Basement Facebook group. Your story might help another Stacker avoid a costly mistake.

Because the right advisor doesn't just manage money. They help you sleep better at night.

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5 Signs Your Financial Advisor Might Be Failing You (SB1783)

As we close out the year, we're bringing back this powerful 2023 conversation with financial educator Tiffany Aliche (The Budgetnista) because it resonates even more today than when we first aired it.

Joe Saul-Sehy and OG sit down with Tiffany for a conversation about financial wholeness. Not just having the right accounts, but building a money life that supports you when life doesn't go as planned.

Tiffany shares what the past year taught her about preparedness, community, and resilience after the sudden loss of her husband, and why the systems she had in place mattered more than any single perfect financial move. This isn't a story about fear or worst-case scenarios. It's about confidence, clarity, and giving yourself grace while still doing the work that protects the people you love.

Along the way, Joe and OG pull practical lessons every Stacker can use without overwhelm or guilt. The money basics that quietly make everything else easier: beneficiaries, insurance, wills, and the difference between having a plan and having peace of mind.

If you've ever wondered whether you're focusing on the right financial priorities, or how prepared you really are, this episode offers reassurance, perspective, and a clear path forward.

WHAT YOU'LL TAKE AWAY:

 What financial wholeness really means beyond budgets and spreadsheets

 Why having basic systems in place matters more than chasing optimization

 The quiet power of beneficiaries, insurance, and estate documents

 How preparation can reduce stress not just financially but emotionally

 Why community and education are essential parts of a strong money life

 How to enter a new year with confidence instead of pressure

THIS EPISODE IS FOR YOU IF:
You've ever wondered whether you're focusing on the right financial priorities, you want to make sure your essentials are covered without overwhelming yourself, you're thinking about what really matters as you head into a new year, or you believe the smartest financial move isn't always doing more but making sure the basics are handled.

This is one of those episodes that makes you pause and ask: If something unexpected happened tomorrow, would my money make life easier or harder? You don't need to answer that perfectly today, but it's a great conversation to start.

Sometimes the smartest financial move isn't doing more. It's making sure the essentials are handled so you can live fully the rest of the time.

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The Money Basics That Save You When Life Goes Sideways (SB1782)

What if the biggest upgrade to your finances wasn't a new strategy but a new way of thinking?

Joe Saul-Sehy and OG unpack the small but powerful money mindset shifts that separate people who know what to do from people who actually make progress. This isn't about motivation posters or vague positivity. It's about practical mental frameworks that lead to better decisions, fewer regrets, and more confidence with money.

The team walks through their top five money mindset tweaks. How to focus on strengths instead of endlessly fixing shortcomings. Why taking action beats overthinking every time. How playing long-term games with the right people changes everything. Along the way, they connect mindset directly to real-world choices, like how thinking clearly about value, longevity, and opportunity cost affects something as everyday as buying a car.

That's where Carl Brauer from iSeeCars joins the conversation with insight into which vehicles deliver the best long-term value. It's a perfect case study in mindset-driven money decisions. Not chasing shiny objects, but choosing options that quietly compound in your favor.

If you've ever felt like you're doing most things right but not seeing the results you want, this episode helps you zoom out, recalibrate, and move forward with intention.

WHAT YOU'LL LEARN:

 The five mindset shifts that consistently lead to better money outcomes

 Why progress comes from doing rather than perfecting your plan first

 How understanding compounding changes the way you view time, effort, and money

 Why focusing on your strengths beats trying to fix every weakness

 How to think about purchases like cars through a long-term value lens

 The power of playing long-term games with people who think the same way

THIS EPISODE IS FOR YOU IF:
You feel like you know what to do with money but struggle to actually do it, you're tired of motivational content that doesn't translate into real change, you want to understand why some people progress faster with less effort, you're making a big purchase soon and want to think about it more clearly, or you believe the way you think about money matters as much as what you do with it.

Sometimes the most profitable move isn't changing your plan. It's changing how you think about the plan.

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

The Money Mindset Tweaks That Actually Change Results (SB1781)

What separates people who build lasting wealth from people who just chase the next hot investment? David Greene from BiggerPockets has a clear answer, and it's not what most people want to hear.

Joe Saul-Sehy and OG revisit a standout 2023 conversation with David that still resonates today. His story isn't about shortcuts, hacks, or getting lucky. It's about skill building, discipline, and learning to turn everyday work into long-term opportunity. From scooping ice cream at Baskin Robbins to building a successful real estate career, David breaks down what actually creates momentum over time and why "passive income" still requires serious intention.

This episode showcases the kind of conversation that belongs in the vault. David explains what makes work feel worth it, how to develop skills that compound, and why the unsexy fundamentals matter more than the flashy strategies everyone's talking about. If you're tired of hype and ready for substance, this interview delivers.

The show also tackles two critical protection topics. Adam Barowy from UL's Fire Safety Research Institute joins to explain the real (and often overlooked) risks of lithium-ion batteries in e-bikes, scooters, and everyday devices. He shares practical steps every family can take to reduce fire risk without panic or overreaction.

Then Joe and OG field a listener question about keeping family property in the family. The discussion explores estate planning tradeoffs, communication challenges, and how to think through shared ownership without creating future conflict.

Every segment connects to the same core idea. Building a life that's not only financially strong but resilient, safe, and meaningful.

What You'll Walk Away With:

• David Greene's framework for building wealth through skill mastery, not investment shortcuts

• Why "passive income" is never truly passive and what actually makes work sustainable long term

• Practical fire safety guidance for lithium-ion batteries you probably already own in your home

• Simple steps to reduce household fire risk based on real research, not fearmongering

• Thoughtful estate planning insights for preserving family property across generations

• How to think about money not just as growth but as protection and stewardship

This Episode Is For You If:

• You're tired of wealth-building advice that sounds too good to be true

• You want to hear how someone actually built success through discipline and skill development

• You've got lithium-ion batteries around the house and never thought twice about fire safety

• You're thinking about how to pass property or wealth to the next generation without creating conflict

• You believe the smartest money moves involve both growing and protecting what you have

Before You Hit Play, Think About This:

What's one area of your financial life where you're focused on growth but might need more protection or structure? Share your thoughts in the Spotify comments or bring the discussion into the Basement Facebook group because this episode tends to spark great follow-up conversations.

Sometimes the smartest money move isn't about earning more. It's about keeping what you've built safe and aligned with what matters most.

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David Greene: How to Build Real Wealth (Not Just Chase Hype) SB1780

Is the constant push to be great quietly making life (and money) harder than it needs to be?

This vault-worthy episode from 2023 hits differently, especially during a season when expectations run high and energy can run low. Joe Saul-Sehy is joined by Len Penzo, Paulette Perhach, Diania Merriam, and special guest Stephanie O'Connell Rodriguez for a candid roundtable about ambition, procrastination, perfectionism, and the surprising freedom that comes from choosing good over exhausting.

Instead of chasing flawless systems or ideal outcomes, the conversation explores what actually moves the needle in real life. Building momentum. Removing friction. Letting go of the idea that every decision has to be optimized. Whether it's money habits, career goals, or simply getting unstuck, this episode offers a calmer, more sustainable way forward without lowering your standards or your future.

Along the way, the group shares personal stories, practical strategies, and a few moments that only happen when smart people stop pretending they've got it all figured out. It's thoughtful, honest, and exactly the kind of perspective many Stackers didn't know they needed.

What You'll Take Away from This Episode:

• Why perfection often slows progress more than fear or lack of knowledge

• How "good enough" can be a powerful financial strategy, not a compromise

• Practical ways to break through procrastination without burning out

• When delegation and automation actually help and when they just add complexity

• How to balance ambition with contentment without feeling like you're settling

• Why consistency beats intensity in both money and life

Questions Worth Sitting With:

Where are you chasing "perfect" when "done" would be better? What would improve immediately if you lowered the bar just a little? Which money habit could become easier if you stopped optimizing it?

We'd love to hear your take. Share your thoughts in the Spotify comments or bring the conversation into the Basement Facebook group, especially if this episode gave you permission to ease up without giving up.

Sometimes the best financial move isn't pushing harder. It's choosing progress that actually fits your life.

This one's a quiet classic, and those tend to age the best.

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

The Perfection Trap: Why Striving Less Might Help You Save More (SB1779)

Today we're all about your letters. We'll start with a question about moving funds around to avoid some taxes, jump into helping a 25-year-old decide whether to max out his retirement accounts, answer a question about robo advisors, and then launch into helping kids with money, how to save for a house, and more.
In our headlines segment we'll talk to Joe Jiminez from The Alternate Life podcast. Maybe you've had the urge to quit your day job and go on a journey, but few of us have actually followed through. Joe Jiminez dumped the job and spent his summer walking the Continental Divide Trail. We might not be able to take the summer off ourselves, but we'll at least ask Joe what it's like.
Then later on, we'll throw out the Haven Life Line to Reggie, who's heard on the show that OG isn't particularly fond of Betterment or Wealthfront. Reggie has a bulk of his money in Wealthfront and Betterment, so he's wondering...what's the issue?
As always, we'll still save some time for Doug's trivia...which today is exceptionally epic.
Thanks to Proper Cloth for supporting Stacking Benjamins. Get $20 off your first custom shirt at Propercloth.com/sb.
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Quitting Your Job at 31 to Achieve a Life Goal (Your Letters)

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