The Stacking Benjamins Show

Tax planning in June? Of course! Why would you wait until next year, when you can't make ANY financial moves that save you money, to start figuring out how to cut your tax bill? Right now, at nearly the halfway point of the year, we'll dive into how to understand your taxes and make cuts with our tax planning mentor, Hannah Cole. Hannah will walk us through tax savings ideas for everyone, and then we'll focus on those people who have either started a side hustle or who are entrepreneurs and share some great tips for business owners. Even if you're just dreaming about having a business or "working for the man," we've got you covered. Plus, in our headline segment, two brothers woke up one day this spring and found themselves disinherited, losing out on approximately one million dollars! How did that happen? It could have all been avoided, and YOU can avoid this problem too. We'll walk you through HOW to make sure your beneficiaries receive the funds you've decided should go to them. We'll also explain how wills and trusts work, and get you started toward building a better "estate plan." Of course, Doug brings his awesome trivia challenge AND we answer a question from a Stacker in need. FULL SHOW NOTES: https://stackingbenjamins.com/tax-planning-year-round-1532 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

How are you preparing for retirement? Have you looked at all of the dimensions to ensure you have a successful, long runway of money always available? On today's special roundtable episode, we dive into a piece that claims there are seven things you need to do in order to be prepared for retirement. Joining us are: Don McDonald from the Talking Real Money podcast, Paula Pant from Afford Anything, and OG. In the second half of the show, sponsored by DepositAccounts.com, we dive into risk mitigation, the importance of maintaining adequate cash reserves while in retirement, and keeping a historical context of current events. Be sure to stick around for the yearlong trivia competition with Doug's baseball-themed trivia. FULL SHOW NOTES: https://stackingbenjamins.com/moves-to-make-before-retirement-1531 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

There’s another lawsuit brewing in the world of retirement planning. This time, participants in a 401(k) plan in California are raising concerns about how Qualcomm is handling the money forfeited when employees don’t complete their vesting schedules. Vesting schedule? What’s that all about? Today, we'll break down everything you need to know about vesting schedules, so you can navigate your job benefits with confidence. Whether you’re dealing with a vesting cliff or a staggered vesting schedule, we’ve got you covered. We’ll explain how they work, the taxes involved, how to plan around them, and how to think about any money that isn’t fully yours yet. Plus, for business owners, we'll discuss how to balance keeping talent with implementing vesting schedules. Get ready for a fun and informative session on one of the trickier aspects of financial planning! In our TikTok minute, we’re sharing a clip from Fox News where a contributor predicts what will happen to the stock market if Trump is convicted after his recent trial. Spoiler: He was convicted. Let’s see if his prediction came true and how it might impact your money. We also have a note from a fellow Stacker who thought, "I better call Saul...Sehy & OG." He’s worried about contributing to a Roth IRA because his income is too high. We’ll discuss strategies like backdoor Roth contributions, Roth 401(k) plans, and some of the tricky rules around Roth IRA conversions that can trip people up. And of course, we’ll share a fun trivia question from Doug, sit on the back porch, and so much more! FULL SHOW NOTES: https://stackingbenjamins.com/all-about-vesting-1530 For deeper dives with curated links, topics, and discussions, check out our newsletter, The 201, at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Unlocking the FinTech Disaster: What You Need to Know You might not know it, but a huge number of people have their money trapped in a recent FinTech crisis. When the middleman company Synapse went bankrupt, it froze funds in many popular FinTech apps, including Yotta, a sweepstakes app that makes saving money fun. Will Yotta and other affected FinTech companies be able to return their users' money? What does this mean for the future of FinTech? Is more legislation on the way to prevent this from happening again? While new updates are rolling in daily, we’ll break down what we know and how it impacts your finances. The Fascinating History of Banking Later in the show, we'll dive into the history of banking with our mentor for the day, Paolo Zannoni. Paolo is the deputy chairman of Prada, a historian, and the former head of operations for Goldman Sachs in Russia. He'll reveal that while today's FinTech issues might seem new, they’re part of a repeating historical pattern. Learn how modern banking originated in Pisa, the relationship between banks and credit, how minting money sped up the creation of banks, and how banks and governments have collaborated for centuries. Better Call Saul... Sehy and OG: Setting Savings Goals In our Better Call Saul... Sehy and OG segment, a Stacker mom seeks advice on helping her twenty-year-old daughter set savings goals. The young woman is great at saving but isn’t sure what to save for. We always say, "Begin with the end in mind," but what if you don't know what "the end" looks like? We’ll discuss practical steps to find and set meaningful savings goals. Plus... Don't miss our memorable back porch discussions, Doug's always-entertaining trivia, and much more! Join the Conversation For deeper dives with curated links, topics, and discussions, subscribe to our newsletter, The 201, at stackingbenjamins.com. Enjoy the Show! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Why aren't all big-money ballers able to pile up massive stacks of Benjamins? How come some average Joe earners can build significant wealth? On today's special roundtable episode, we dive into a blog post listing the top six reasons people who make big money can't save. One of the Top 100-rated financial planners by Investopedia in 2023, Elaine King, joined us. She's not alone, though. We also feature the creator of the award-winning blog Afford Anything, Paula Pant, and our own resident CFP, OG. In the second half of the conversation, sponsored by DepositAccounts.com, we'll explore the actual benefits of relocating to save money. Stick around for our year-long trivia competition inspired by our special guest, Elaine King's, home country of Peru. FULL SHOW NOTES: https://stackingbenjamins.com/top-six-reasons-youre-not-rich-1528 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

Open AI recently survived a brutal firing/rehiring of their CEO and a complete board resignation. In the past, we've heard extensively from Sam Altman, the CEO of Open AI, but we haven't heard from the board. Today we use the words of a board member who's speaking openly for the first time to ponder the question, "Should YOU have a board of directors for your personal financial life?" We parse the words "board of directors" to determine what that really means, and we dive into how these relationships truly work. Should we except "hostile" advice from strangers? Should we consider our friends to be on our board casually? We explore all of these options and more on today's extended Wednesday headline discussion! Of course, we feature a TikTok minute that you won't want to miss as one young woman discovers the true trap that taxes are on your ability to build wealth. Doug also supplies his amazing trivia, and of course, we also answer a call for help from a Stacker who thought, "I'd better call Saul...Sehy and OG." FULL SHOW NOTES: https://stackingbenjamins.com/create-your-board-of-directors-1527 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

How much of your life is controlled by programming? If you're looking to make more money you have to look at what's blocking you today and transform yourself into an earning machine. It turns out that the key to earning more is right between your ears. Brandon Epstein works with top professionals (athletes, CEOs, entrepreneurs, and high-level executives) to help them achieve even more. You've heard us say many times that great people surround themselves with amazing individuals. Brandon IS that maker of amazing talent. He doesn't create talent. He teaches you how to tap the talent you know is waiting to be deployed. We'll talk about mental blocks, societal programming, identifying those blocks, and how to break free of them on today's podcast. But before that we ask the question, can you trust online reviews? We not only walk through how many of your favorite sites are manipulating their review systems, but we also give you a better method to find and keep talented people around you (or amazing companies that you should work with). We also take a call from a Stacker who wonders how to invest money she's rolled over into her IRA, AND we dive deep on Doug's incredible trivia question. FULL SHOW NOTES: https://stackingbenjamins.com/break-through-mental-blocks-achieve-success-1526 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

Maybe the key to achieving happiness doesn't lie in being perfect (financially-speaking). Today we dive deep into striking the balance between channeling your inner Warren Buffett/Jack Bogle/Scrooge McDuck hybrid and channeling your inner Neighbor Doug at the special Summer Slam-Bingo-Ladies Night down at the Sizzler. Joining us on today's special roundtable discussion are: the woman who’ll help you get out of being miserably in debt, award-winning author, Erin Skye Kelly; the guy who helps people be responsible with their future money, the host of the Inspired Money podcast, Andy Wang; and the Scrooge McDuck of this here podcast, OG. In the second half of the show, sponsored by DepositAccounts.com, we dig into how to make money a fun topic. Does being a mega tracker bring you anxiety? If so, maybe you should focus on putting savings first and then spending what's left over. Finally, be sure to stick around for Doug's Benjamin stack-related trivia. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-maintain-happiness-and-be-good-with-money-1524 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

Today high yield bonds are in the spotlight. A recent Wall Street Journal piece details how you can get eight percent currently in the bond market (which is a rate most stock investors would be happy to lock in). Why may this NOT be a good deal? Well, first you have to understand how bonds work. So, we'll explain that. Second, you'll have to understand the difference between buying a bond fund and a single bond. So, we'll also explain that. Third, we'll have to explain how many investors lose money because they don't understand concepts such as "risk premium." So, happy, we'll show you what that means. It's all things bonds on today's show! But that's not all. Stacker Tom asked a GREAT question in the Stacking Benjamins basement the other day, because it's SUPER complicated. He asks about IRMMA, RMDs, and Medicare. Huh? We LOVE this question because it shows the depth of knowledge you'll need to have to get everything right...but also shows you how you do NOT need to know everything today/right now/immediately. We'll explain all of these terms on today's show (and also illuminate how frustrating the world of financial terms can be during our TikTok minute). FULL SHOW NOTES: https://stackingbenjamins.com/bonds-hidden-risks-1524 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Learning a new language is difficult, and the language of money is no exception. Brian Preston from The Money Guys has created shortcut words and phrases like "financial mutant" to help you focus on what's important and ignore the rest. We'll discuss how to get started, the key moves to reach long-term goals, how to avoid making costly mistakes, and more. Whether you're someone just beginning your journey or a seasoned investor, there's a little something for everyone every time we speak with Brian. In our headline segment, a publication decided to ask AI (Chat GPT) how to beat the stock market. The AI responded with advice, which we'll dive into thoroughly to see if this is the wave of the future. Even better news: beginning this week, we'll track this AI driven portfolio to see if it truly is a better way to invest than a collection of index funds (or just one index). But that's not all. We also answer a question from a Stacker AND Doug shares his amazing trivia. FULL SHOW NOTES: https://www.stackingbenjamins.com/become-a-financial-mutant-1523/ 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

Welcome to a very special roundtable edition of the show! On today's show, we're talking about debt, and how to use it (or avoid it) as part of your financial plan. We're joined by Afford Anything's Paula Pant; the host of The Personal Finance Podcast, Andrew Giancola; and the host of the Earn & Invest podcast Doc G! In the second half of the show, sponsored by DepositAccounts.com, we dive into the possible positive effects that having a large amount of debt can have - in terms of constant motivation to make progress. Be sure to stick around for Doug's mind-blowing trivia question about debt. FULL SHOW NOTES: https://stackingbenjamins.com/the-role-of-debt-in-your-financial-plan-1522 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

A recent major media outlet reports that people earning less than $50,000 per year aren't eating at restaurants as often as they did a year ago, and that eating away from home is becoming a trait increasingly more for the wealthy. Today we talk about not only this trend but others as we help you grab a firm hold on your wallet. One of the "big three" expense categories is food cost, and cutting your restaurant tab can be an effective way to sock more money toward financial independence. We'll share tools, strategies, and anecdotes from people who've successfully navigated the restaurant game on today's show. Plus, we share a TikTok minute from one creator who's more than a little worried about homeowners and renters insurance. You'll hear why and how to make better decisions around these policies. Then we look at other communities online and answer random questions we've seen on the web that we think haven't been answered very well. We talk CD rates, driving for DoorDash, and more. FULL SHOW NOTES: https://stackingbenjamins.com/state-of-restaurants-2024-1521 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

Nothing says summer more than a trip to your favorite regional theme park. Whether with friends, family, or alone, a trip to a theme park can be either super expensive and tiring or a blast. So that's why our friend from Theme Park Insider, Robert Niles, is BACK to help us all kick off summer on the right foot, spending money wisely on experiences that will be memorable and fun. Not only will he help you save some money, but he'll also share tips on the hottest parks and attractions around the country. We'll talk about food (best food AND deals), thrill rides, family attractions, and more. In our headline, OG and Joe dive into the exchange-traded fund (ETF) craze. People are pouring money into ETFs, but are they doing it wisely? In many cases, no. We'll share how exchange-traded funds work, which types are the best to choose from, and how to avoid getting caught investing in something that sounds great...but truly is not. Of course, we'll also share Doug's trivia question about the biggest stock market drop of all time and FINALLY wrap up our 2024 "Joke Off." It's another day of fun on the Stacking Benjamins show. As always, thanks to our sponsors, and enjoy another show where we're ad-free the ENTIRE second half of the show (as always!). FULL SHOW NOTES: https://stackingbenjamins.com/theme-parks-summer-2024-1520 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

At the end of the day, stacking Benjamins is all about living a better, happier life. But how can you achieve greater happiness while still on your stacking journey? That's what we're all about on today's special, all-about-happiness episode. We're joined by our special guest, host of the Best Interest Podcast, Jesse Cramer; a lady who knows plenty about the intersection of money and happiness, Paula Pant; and our own rainbow and unicorn ray of sunshine, OG! In the second half of our discussion, sponsored by DepositAccounts.com, we dive into more of our favorite ways to improve your happiness. Be sure to stick around for the ongoing year-long trivia competition as Doug brings a rainbow/magical wizard-related trivia question. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-achieve-happiness-1519 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

Robinhood seams to always be in the news, and usually not for a good reason. Today Joe and OG discuss Robinhood crypto potentially being sued be the SEC. Crypto still seems to be the wild wild west. Is the SEC trying to put some regulations around crypto but then again isn't that the whole purpose of crypto? Our TikTok is all about following the prospectus and whether Doug starts his fire with those? We answer a question from Stacker, Damon, about whether or not he can help out his kids fund their Roth IRAs? FULL SHOW NOTES: https://www.stackingbenjamins.com/choose-the-right-broker-1518 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

Matt Schulz is the PERFECT mentor to teach us how to negotiate because, in his own words, he's not a natural negotiator. Today he proves that you don't have to be a natural to find better deals on your credit card interest rates, prescription, rental cars, hotel rooms, and more. He'll walk us through the common misconceptions around negotiating and help us learn to ask politely for more for ourselves. In our headline segment, small company stocks are struggling to keep up with the S&P 500. Why would someone stay diversified when large companies are doing so well and other stocks are not? We'll walk through the science of diversification and why it's a mistake to bail on underperforming asset classes during down periods. Of course, that's not all. We'll share some of Doug's trivia, answer a question from a Stacker about emergency fund interest rates, and more! FULL SHOW NOTES: https://www.stackingbenjamins.com/negotiate-everything-with-matt-schultz-1517 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

Personal finance education in schools is finally getting some attention, but the best financial education starts at home. On today's special prelude-to-summer-vacation roundtable discussion, we're joined by three experts in the field of kids and money. Joining us today are John Lanza from The Art of Allowance podcast, the founder of the Wealthy Kids Investment Club Maya Cobic, and money educator Rob Phelan. In the second half of the show, sponsored by DepositAccounts.com, we talk about how to teach kids about money in the digital world. And you won't want to miss Doug's toothy finance-related trivia question! FULL SHOW NOTES: https://www.stackingbenjamins.com/your-kids-and-money-1516 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

A new CBS report shows that the average person's perception of how much they'll need for retirement has changed dramatically versus four short years ago. Do you think the number is higher or lower? We'll not only share that, but we'll also dive into this idea of calculating the correct amount to save. When is it truly important to begin working on your retirement vision? When should you be more scientific about your overall asset allocation toward your goals, and when does it make sense to just save money? Today we'll share all of those milestones and more as we help you calculate a retirement number that's better geared toward your personal goals AND that's only created when it actually makes sense to have a goal. In our TikTok minute, there are property owners all over the world testing their insurance premiums. We'll share how. We also take a call from Stacker Collin, who wonders which option to take for health insurance (pronounced IN-surance), since it's likely he and his spouse will be working for the same company. Of course, we have some fun out on the back porch talking all things television, and more. FULL SHOW NOTES: https://www.stackingbenjamins.com/calculate-your-retirement-number-1515/ 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

Janesse Torres is a force of nature. She purposefully quit her high-paying job as an engineer because it didn't fit her personality AFTER posting about it on social media. Today she joins us to talk about living your life intentionally, building financial reserves, demanding more from your boss, and if you get "no" as your answer, moving on. As the host of Yo Quiero Dinero and a woman who's a social media/blogging powerhouse, she's used to talking about life as it is, without mincing words. Today you get the full Janesse as she shares how to negotiate, build savings, and more. Plus, in our headline, new legislation should help you find advisors who are trustworthy when it comes to working with your retirement plan money. Will the reality equal the promise? We weigh in on how the legislation works, what we think will happen, and how to plan whether it finally becomes law in September or not. You'll be ready to find better help for your retirement after today's show. Plus we answer a call from Jen, who wonders about HSA plans. Can she move money from her IRA to an HSA? And that's not all....of course, Doug shares some trivia you'll be sharing later with friends and family. On the back porch, we talk about what we've decided for our Friday roundtable shows. Who's going to be the new frequent contributor? Of course, that's just the FIRST episode of our new eight weeks! We've got action packed mentorship from Brian Preston, Robert Niles, humor from Lisa Curry, great feedback from a panel of kids-and-money experts, and more! FULL SHOW NOTES: https://www.stackingbenjamins.com/get-financially-lit-1514 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

Join us as we wrap up Greatest Hits Week with a favorite roundtable discussion: What lessons would you share with your younger self? This episode originally aired on November 5, 2021, so please disregard any mention of current events. If you could go back and give your younger self one piece of advice, what would it be? Maybe it’s to take more chances or say adios to the boss that treats you horrible or maybe it’s just to live life to the fullest and not worry about what others think. Today our roundtable discusses a blog piece from Ryan Holiday about mistakes he’s made and advice he would give himself. Caleb Gulliams (Better Wealth), Paula Pant (Afford Anything) and Doc G (Earn & Invest) join our roundtable and talk about advice they’d give their younger self and the mistakes they’ve made. FULL SHOW NOTES: https://www.stackingbenjamins.com/life-lessons-to-younger-self-greatest-hits-1513 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