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The Stacking Benjamins Show

Podcast The Stacking Benjamins Show
StackingBenjamins.com | Cumulus Podcast Network
Named 2023 Best Personal Finance podcast by Bankrate.com, The Stacking Benjamins Show has a light and friendly tone. Hosts Joe Saul-Sehy and OG aim to make fina...

Available Episodes

5 of 1285
  • The Best Tax Prep Software of 2025 (SB1655)
    Choosing the Best Tax Software for Your Needs Tax season is hereā€”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 Blockā€™s virtual tax prep ā€“ If you want real humans to double-check your numbers, this might be your go-to. Which tax software works best for unique situations ā€“ Side gigs, stock trading, crypto investmentsā€¦ different situations call for different solutions. Navigating Tax Day without the stress ā€“ Tips to avoid last-minute panic and make sure youā€™re not leaving money on the table. Crypto scams and meme coins ā€“ Because tax season isnā€™t stressful enough without adding that mess into the mix. Meanwhile, Doug serves up world-famous trivia with a nod to classic childrenā€™s books, beloved authors, and sing-song rhymes. Plus, we take a detour into sector betting, market trends, andā€”of courseā€”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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  • Dream Big, Live Free: Grant Sabatier's Guide to Entrepreneurship (SB1654)
    Ever wondered if working for yourself could be the game-changer your finances need? Grant Sabatier thinks so, and today, heā€™s diving into the realities of entrepreneurshipā€”from smart strategies to potential pitfalls. Where to start if youā€™re considering entrepreneurship ā€“ 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 ā€“ Why guardrails and structure matter more than unlimited freedom. Pricing strategies and finding customers ā€“ Because even the best ideas need paying customers. Entrepreneurial misconceptions ā€“ Spoiler: Itā€™s not all Ferraris and private jets. Can your wedding be a tax deduction? ā€“ 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 wonā€™t guess it). And if you stick around long enough, letā€™s just say there may or may not be a discussion about a comedy movie that turns financial struggles into pure entertainment. But, you knowā€¦ no promises. If youā€™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. ļ»æFULL 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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  • The Surprising Benefits of Financial Inaction (SB1653)
    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 nothingā€”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 youā€™ll ever adopt (spoiler: it involves less work). The power of downtimeā€”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 financesā€”and how to keep the Joneses from running your budget. When rebalancing your portfolio is necessaryā€¦and when itā€™s just a fancy way to micromanage yourself. A wildly unexpected insurance claim (because finances are never boring in the basement). Oh, and Dougā€™s got a trivia question about a particularly controversial activity that was bannedā€”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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  • Our Top 5 Favorite Parts of a Well-Crafted Financial Plan SB1652
    A great financial plan isnā€™t just about numbersā€”itā€™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, theyā€™ll walk you through the key elements that turn financial chaos into a well-oiled machine. Breaking down big goals into bite-sized wins ā€“ Because climbing a financial mountain is easier when you focus on one step at a time. The magic of tax strategies ā€“ Why a little planning now can keep more Benjamins in your pocket later. Risk management done right ā€“ Avoiding financial pitfalls so your plan stays strong, no matter what life throws your way. The power of simple solutions ā€“ Complexity doesnā€™t always mean better. Sometimes, the best financial strategies are the easiest to execute. The role of a financial guide ā€“ Whether you DIY your plan or bring in an expert, knowing when to get guidance is a game-changer. Meanwhile, Doug tackles a ā€˜Winnie the Poohā€™-inspired predicament (honey jars may or may not be involved) and drops some surprising trivia on the massive market value of antidepressant drugs. If youā€™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. ļ»æThis 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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  • Your Path to a Cost-Effective Car SB1651
    Ever felt overwhelmed by buying a car or managing your time? Youā€™re not alone. Today, we tackle both topics with expert insights and a few unexpected surprises along the way. Car buying decoded ā€“ 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 ā€“ Paula Pant, Dominique Brown, and returning guest Carrie Smith share real-world productivity hacksā€”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 ā€“ The team dives into the doā€™s and donā€™ts of posting while employed. Email overload? Phone calls running your life? ā€“ Smart strategies to take control of your inbox and stop wasting time on endless calls. Celebrity wealth secrets and entertainment picks ā€“ Because financial wisdom can come from surprising places. A roadside hawk encounter?! ā€“ An unexpected story that proves you never know whatā€™s coming next. With practical advice, engaging discussions, and a few twists you wonā€™t see coming, this episode packs in everything you need to take control of your finances and your timeā€”without taking life too seriously. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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About The Stacking Benjamins Show

Named 2023 Best Personal Finance podcast by Bankrate.com, The Stacking Benjamins Show has 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 tableĀ 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.
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