Episodios

  • How to Use Process to Create Sustainable Drive (SB1657)

    How to Use Process to Create Sustainable Drive (SB1657)
    Mar 17 2025
    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 Molly Fletcher on Wednesday. 💰 In this episode: Why motivation fizzles out—and how to make it last The seven keys to Dynamic Drive (and how to apply them to your finances) How milestones and energy management keep you on track Tax strategies for selling shares—FIFO, LIFO, or average cost? Which method helps you keep more of your hard-earned Benjamins? What cowboy fencing teaches us about peak performance (yes, that’s a thing) Plus, Doug serves up a sports trivia challenge—because what’s financial motivation without a little fun? 👉 Listen in now and get fired up—without burning out! FULL SHOW NOTES: https://stackingbenjamins.com/how-to-create-a-sustainable-drive-1657 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
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    1 h y 8 m
  • Yeah, We Overpaid for That (SB1656)

    Yeah, We Overpaid for That (SB1656)
    Mar 14 2025
    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 found $50 tickets… but somehow the total is now $127? Yep, we’ve been there. The True Cost of Convenience – From Uber Eats to express shipping, when is paying extra worth it—and when are we just being lazy? Trivia Time: Pie Day Special! – Who knew McDonald's pie sales could spark heated debate? Well, now we all do. Wedding Costs Gone Wild – Creative ways to cut costs without making your guests eat ramen. The Ben Franklin Effect & Social Hacks – Want better connections without breaking the bank? Turns out, old Ben had some wisdom on that, too. All this, plus some hilarious personal finance confessions that will make you feel better about your last impulse buy. 🎧 Tune in, laugh, and learn how to keep more of your Benjamins! FULL SHOW NOTES: https://stackingbenjamins.com/places-we-know-were-overpaying-1656 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
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    58 m
  • The Best Tax Prep Software of 2025 (SB1655)

    The Best Tax Prep Software of 2025 (SB1655)
    Mar 12 2025
    Choosing the Best Tax Software for Your Needs Tax 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 double-check your numbers, this might be your go-to. Which tax software works best for unique situations – Side gigs, stock trading, crypto investments… different situations call for different solutions. Navigating Tax Day without the stress – Tips to avoid last-minute panic and make sure you’re not leaving money on the table. Crypto scams and meme coins – Because tax season isn’t stressful enough without adding that mess into the mix. Meanwhile, Doug serves up world-famous trivia with a nod to classic children’s books, beloved authors, and sing-song rhymes. Plus, we take a detour into sector betting, market trends, and—of course—movie recommendations. If tax season feels overwhelming, this episode breaks it down, keeps it light, and helps you pick the right software to file with confidence. 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
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    1 h y 10 m
  • Dream Big, Live Free: Grant Sabatier's Guide to Entrepreneurship (SB1654)

    Dream Big, Live Free: Grant Sabatier's Guide to Entrepreneurship (SB1654)
    Mar 10 2025
    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 customers – Because even the best ideas need paying customers. Entrepreneurial misconceptions – Spoiler: It’s not all Ferraris and private jets. Can your wedding be a tax deduction? – We explore the entertaining but highly questionable ways some people try to make this work. Meanwhile, Doug serves up trivia on the highest-grossing console game ever (bet you won’t guess it). And if you stick around long enough, let’s just say there may or may not be a discussion about a comedy movie that turns financial struggles into pure entertainment. But, you know… no promises. If you’ve been toying with the idea of starting your own thing, this episode is packed with insights, real talk, and a few surprises along the way. FULL SHOW NOTES: https://stackingbenjamins.com/unlock-your-inner-entrepreneur-with-grant-sabatier-1654 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
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    1 h y 20 m
  • The Surprising Benefits of Financial Inaction (SB1653)

    The Surprising Benefits of Financial Inaction (SB1653)
    Mar 7 2025
    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 might actually make you richer. Why your future self will thank you for setting up auto-pay (hint: fewer late fees, more naps). The sneaky ways peer pressure messes with your finances—and how to keep the Joneses from running your budget. When rebalancing your portfolio is necessary…and when it’s just a fancy way to micromanage yourself. A wildly unexpected insurance claim (because finances are never boring in the basement). Oh, and Doug’s got a trivia question about a particularly controversial activity that was banned—because, apparently, not everything fun is legal. Stick around for weekend plans, final thoughts, and maybe even a surprise or two (because we like to keep you on your toes). This episode originally aired on June 10, 2022. Please disregard any mention of current events. The original show notes can be found here. 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
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    1 h y 12 m
  • Our Top 5 Favorite Parts of a Well-Crafted Financial Plan SB1652

    Our Top 5 Favorite Parts of a Well-Crafted Financial Plan SB1652
    Mar 5 2025
    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 financial mountain is easier when you focus on one step at a time. The magic of tax strategies – Why a little planning now can keep more Benjamins in your pocket later. Risk management done right – Avoiding financial pitfalls so your plan stays strong, no matter what life throws your way. The power of simple solutions – Complexity doesn’t always mean better. Sometimes, the best financial strategies are the easiest to execute. The role of a financial guide – Whether you DIY your plan or bring in an expert, knowing when to get guidance is a game-changer. Meanwhile, Doug tackles a ‘Winnie the Pooh’-inspired predicament (honey jars may or may not be involved) and drops some surprising trivia on the massive market value of antidepressant drugs. If you’re ready to streamline your financial life and celebrate your progress along the way, this episode is packed with insights, strategy, and a few unexpected twists. This episode originally aired on January 18, 2023. Please disregard any mention of current events. The original show notes can be found here. 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
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    1 h y 12 m
  • Your Path to a Cost-Effective Car SB1651

    Your Path to a Cost-Effective Car SB1651
    Mar 3 2025
    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 real-world productivity hacks—whether you're self-employed, working 9-to-5, or just trying to make better use of your day. Avoiding social media missteps at work – The team dives into the do’s and don’ts of posting while employed. Email overload? Phone calls running your life? – Smart strategies to take control of your inbox and stop wasting time on endless calls. Celebrity wealth secrets and entertainment picks – Because financial wisdom can come from surprising places. A roadside hawk encounter?! – An unexpected story that proves you never know what’s coming next. With practical advice, engaging discussions, and a few twists you won’t see coming, this episode packs in everything you need to take control of your finances and your time—without taking life too seriously. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    1 h y 15 m
  • What's In Your Financial "Go Bag"? SB1650

    What's In Your Financial "Go Bag"? SB1650
    Feb 28 2025
    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 stay in the filing cabinet? Cash vs. digital access – How much should you keep in physical cash? And is gold really a smart emergency asset, or just a really heavy way to slow yourself down? Estate planning and emergency preparedness – The financial moves today that can make a crisis less stressful later. Password managers: genius or a liability? – We debate whether your digital keys should be stored in the cloud, on paper, or tattooed in invisible ink. Trivia showdown: Doug tests the team’s knowledge with a question that (probably) has nothing to do with financial preparedness. Campus co-op stores and Harvard history—why are we talking about this? You’ll find out. If you’ve been meaning to get your financial house in order for emergencies, this episode has everything you need to build your own financial go bag—without overpacking. FULL SHOW NOTES: https://stackingbenjamins.com/your-financial-go-bag-1650 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
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    58 m