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PODCAST

The Stacking Benjamins Show

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

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All Episodes

64:54

Better Investing Using Horrible Investment Products...

The Stacking Benjamins Show ·

2025/03/28

Ever fallen for an investment that seemed like a sure thing... until it wasn’t? You’re not alone. Today, we shine a light on some of the worst investment advice out there—and help you steer clear of it. Joining Joe at the roundtable are: Paula Pant from Afford Anything Jesse Cramer from Personal Finance for Long-Term Investors And Don McDonald, financial pro and former astronaut (not really, but just go with it) from Talking Real Money. Infinite banking and other shiny traps – What sounds

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78:29

How NOT To Invest: Lessons from Barry Ritholtz SB1672

The Stacking Benjamins Show ·

2025/03/26

Ever wondered how the top financial minds avoid disaster while the rest of us are busy panic-Googling “best investments 2024”? Today, Joe welcomes Barry Ritholtz of Ritholtz Wealth Management down to Mom’s basement for a conversation that flips typical investment advice on its head. It’s not about what to do—it’s about what not to do if you want to grow your money without losing your sanity.Barry shares battle-tested insights from his years in the trenches, covering everything from behavioral

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67:12

10 Ways to Stop Blowing Up Your Investment Portfolio...

The Stacking Benjamins Show ·

2025/03/24

What do weddings, wineries, and Whoppers have to do with smart investing? This week, Joe, OG, and Doug kick off the episode with stories from the road—including a surprise credit card confession that somehow involves a Burger King (because of course it does). But then the gang shifts gears and dives into real money talk, breaking down investing wisdom from the legendary Barry Ritholtz. From navigating market cycles to keeping your emotions in check, Barry’s top 10 tips serve up the kind of

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64:39

How Pros Build Motivation Into an Effective Financial...

The Stacking Benjamins Show ·

2025/03/21

Ever wonder why some people crush their financial goals while others keep hitting snooze? Today, we’re talking about the secret sauce behind sticking to a financial plan—and no, it’s not just “wanting it more” (though that helps). Joining Joe in the basement is OG, alongside personal finance expert Jesse Kramer from The Best Interest and CFP Dana Anspach from Sensible Money. Together, they’ll break down why staying financially motivated is harder than it looks—and how to actually keep yourself on

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81:59

Climb Out of Your Rut: Molly Fletcher on Creating...

The Stacking Benjamins Show ·

2025/03/19

Ever feel like you're stuck in a rut, spinning your wheels, or just running low on motivation? Today, we crack the code on sustaining drive and avoiding complacency with former sports agent Molly Fletcher, who’s worked with some of the biggest names in sports and has been dubbed the female Jerry Maguire. She breaks down the fine line between contentment and coasting, plus shares keys to staying at the top of your game—from managing energy to embracing adversity like a pro.But wait, there’s more

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67:44

How to Use Process to Create Sustainable Drive (SB1657)

The Stacking Benjamins Show ·

2025/03/17

Ever start a new financial goal feeling unstoppable, only to lose momentum when life gets in the way? Staying motivated isn’t just about working harder—it’s about working smarter. Today, Joe and OG take a deep dive into Dynamic Drive, the key to keeping your financial momentum going without burnout. We’ll break down the seven essential pillars—mindset, energy, discipline, curiosity, resilience, connection, and confidence—so you’re ready to hit the ground running when we welcome former sports agent

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57:43

Yeah, We Overpaid for That (SB1656)

The Stacking Benjamins Show ·

2025/03/14

Ever feel guilty about that $7 airport coffee or the mystery fees that somehow turn your $15 DoorDash order into a $40 financial regret? You’re not alone. This episode, Joe Saul-Sehy is joined by Paula Pant (Afford Anything) and Justin Peters (The Struggle Is Real) to unravel the sneaky ways convenience drains our wallets. In this episode: Airport Food: The Ultimate Financial Heist – Why does a sad turkey sandwich cost more than a steak dinner? We investigate. Concert Tickets & Junk Fees – You

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70:05

The Best Tax Prep Software of 2025 (SB1655)

The Stacking Benjamins Show ·

2025/03/12

Choosing the Best Tax Software for Your NeedsTax season is here—so which software should you trust with your hard-earned Benjamins? Eric Rosenberg from The College Investor joins us to break down the best options, whether you're a side hustler, crypto investor, or just looking for a free filing solution. Will TurboTax take the crown again, or is there a surprise champ? You might be shocked by which software stands out this year. H&R Block’s virtual tax prep – If you want real humans to

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80:02

Dream Big, Live Free: Grant Sabatier's Guide to...

The Stacking Benjamins Show ·

2025/03/10

Ever wondered if working for yourself could be the game-changer your finances need? Grant Sabatier thinks so, and today, he’s diving into the realities of entrepreneurship—from smart strategies to potential pitfalls. Where to start if you’re considering entrepreneurship – Not every side hustle is a winner, so how do you know if this path is right for you? The power of systems and constraints – Why guardrails and structure matter more than unlimited freedom. Pricing strategies and finding

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71:46

The Surprising Benefits of Financial Inaction (SB1653)

The Stacking Benjamins Show ·

2025/03/07

Feeling the pressure to constantly tweak your investments? Today, we uncover the surprising benefits of financial inaction with insights from CFP Dana Anspach, Len Penzo, and OG. We dive into the wisdom of sometimes doing nothing—because, as it turns out, sitting on your hands (financially speaking) can be a power move.Why lazy portfolio management might be the smartest strategy you’ll ever adopt (spoiler: it involves less work). The power of downtime—turns out, stepping away from your money

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72:01

Our Top 5 Favorite Parts of a Well-Crafted Financial...

The Stacking Benjamins Show ·

2025/03/05

A great financial plan isn’t just about numbers—it’s about creating a roadmap that turns dreams into reality. Today, Joe and OG take a trip down memory lane, reflecting on their favorite parts of building a great financial plan. Whether you're tackling long-term goals, fine-tuning your tax strategy, or simplifying complex decisions, they’ll walk you through the key elements that turn financial chaos into a well-oiled machine.Breaking down big goals into bite-sized wins – Because climbing a

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74:37

Your Path to a Cost-Effective Car SB1651

The Stacking Benjamins Show ·

2025/03/03

Ever felt overwhelmed by buying a car or managing your time? You’re not alone. Today, we tackle both topics with expert insights and a few unexpected surprises along the way. Car buying decoded – Joe sits down with Phil Reed, Senior Consumer Editor at Edmunds, to break down the best strategies for buying new or used cars, leasing vs. buying, and negotiating with dealers like a pro. The ultimate time management playbook – Paula Pant, Dominique Brown, and returning guest Carrie Smith share

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58:08

What's In Your Financial "Go Bag"? SB1650

The Stacking Benjamins Show ·

2025/02/28

If disaster struck tomorrow, would your financial essentials be ready to grab and go? Today, Joe—along with contributors Paula Pant from Afford Anything, Jesse Cramer from Personal Finance for Long-Term Investors, and our resident expert OG—assemble the ultimate financial go bag. Meanwhile, Doug handles his usual duties as announcer, trivia master, and general chaos instigator.The must-have documents – Passports, Social Security cards, insurance policies... what belongs in your bag, and what can

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58:16

Navigating the Insurance Maze (SB1649)

The Stacking Benjamins Show ·

2025/02/26

Is your insurance setup rock-solid, or are you unknowingly leaving gaps that could cost you big time? Today, we break down the essentials of managing risk in our no-nonsense (but totally entertaining) insurance guide.How much coverage do you really need? We tackle the must-haves and the unnecessary add-ons that might just be draining your wallet. Auto, home, life, and disability insurance—what’s essential and what’s overkill? We walk through the key policies that keep you protected without

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70:07

A Fresh Look at Budgeting Basics (SB1648)

The Stacking Benjamins Show ·

2025/02/24

Ever feel like your budget is running you instead of the other way around? Today, we’re bringing in Shaun Morgan from The Teacher Money Show and Kristin Wade, budgeting coach at My Budget Coach, to help you flip the script. They’ll share how tracking your expenses is the first (and easiest) step toward financial freedom, why budgeting shouldn’t feel like punishment, and how to make your money work without the guilt.But wait—there’s more! We’re diving into creative ways to gamify saving, some

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59:26

Is It Time To Dump International Stocks? (SB1647)

The Stacking Benjamins Show ·

2025/02/21

Is it time to break up with international stocks? They’ve been underperforming U.S. markets for years, so should we finally call it quits, or is there still hope for a global comeback? On today’s episode, Joe, OG, Paula Pant, and Jesse Cramer dig into the great international investing debate. Are international funds a lost cause? The panel unpacks why they’ve lagged U.S. stocks and whether diversification still makes sense. Beyond stocks: Exploring other asset classes—private equity, real

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64:50

When the Job Crumbles: Preparing for Life's Surprises...

The Stacking Benjamins Show ·

2025/02/19

Ever experienced the gut-wrenching moment of losing a job—or worried about what you’d do if it happened? Today, we tackle how to prepare, what to do immediately, and the smartest moves to protect your finances if your job ever disappears. From building an emergency fund to making the most of employer benefits, we’ll walk you through the steps to keep your financial house in order when life throws a curveball.But that’s not all. Estate planning gets a shake-up thanks to the new Secure Act 2.0, and

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82:58

Innovation, XBox and Your Financial Plan (SB1645)

The Stacking Benjamins Show ·

2025/02/17

Feeling stuck in your financial plan—or maybe just in life in general? Whether it’s your money, career, or day-to-day habits, a little innovation can go a long way. Today, we’re breaking down how to rethink and restructure your approach to financial planning and work-life balance using lessons from Microsoft (yes, the Xbox folks). Dean Carignan and JoAnn Garbin insights on how to build a system for innovation—because the best financial plans (and lives) aren’t built by accident. Meanwhile, a woman

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59:54

How Does a Money Nerd Think About "Romance"? (SB1644)

The Stacking Benjamins Show ·

2025/02/14

Love is in the air—and so are overpriced flowers, extravagant dinners, and some serious credit card regrets. In today’s episode, we tackle the financial pressure of Valentine’s Day and show you how to keep the romance alive without setting your wallet on fire.Joining us are financial pros Jesse Cramer, Sarah Catherine Gutierrez, and Len Penzo, who help us break down: The shocking reality of Valentine's Day spending – Who’s dropping the most cash, and is it really worth it? Avoiding post-holiday

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72:09

Wall Street Creates (Yet Another) Hilariously Bad...

The Stacking Benjamins Show ·

2025/02/12

Just when you thought Wall Street had run out of ways to package up risky investments and slap a shiny label on them—here we go again. Today, Joe and OG break down yet another overcomplicated, high-fee, and completely unnecessary financial product. Whether it’s preying on investor fears, promising market-proof returns, or just outright nonsense, we’ll help you spot the warning signs before you end up with a portfolio full of regret.But that’s not all. A viral TikTok tip about hiring your family

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1,392 results

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