The Stacking Benjamins Show

Well, we went and added a comma. You weren't counting, but mom was. Today we'll share the money lessons we've learned over our first 1,000 (wow, have we really made that many?) episodes. Plus, we'll hear from many of our friends you'll recognize from the financial community. We'll share a monster list of our favorite books and resources, but all of the things that we've learned on our journey over the past (near) decade.During our headlines, we'll double up on the experts. First, we'll talk to Dirk Izzo, president and GM of Hospitality at NCR, who'll share how restaurants embraced innovation and kept revenue flowing in the face of unprecedented challenges. In our second piece, we'll invite the man who literally wrote the book on silver investing to explain the craze in the silver markets hitting the news lately. What was happening while we were all watching Gamestop? It turns out, a TON. David Morgan will share his best tips on today's show.As always, we'll save some time for Doug's trivia.Finally, thank you Stackers for making a thousand episodes of this little podcast a reality. We couldn't have done it without you. Enjoy the show.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

It seems absurd now, but Netflix co-founder Marc Randolph was told early on that his company name would never work. Today, he's going to give us some of the same advice he's giving on his new podcast, "That Will Never Work." We'll discuss fighting fear, hiring the right team, having conviction in your ideas, and more. And don't worry if you aren't interested in becoming an entrepreneur. We also asked Marc how to interview better (he's interviewed thousands of people) AND how to ask your boss for a raise. In fact, you'll be surprised what he has to say about raises.Wondering what's going on in the world of fintech? During our headlines, we'll share the newest developments in tech that helps you manage money better. From advancements in technology making your information more secure against hackers to new-new digital banks promising more consumer-friendly resources and more, there's a ton of interesting developments on the horizon. We'll cover many of them. Plus, we'll tackle a headline about Jeff Bezos stepping down from Amazon. Do you think he finally reached his magic number and has enough to retire? Maybe he gave of the lattes and buckled down? Probably not, but that won't stop us from talking about setting goals, retirement, and more.We'll finish today's show with a question we often get about 401k plans. After you leave a company, should you move your funds? Josh left the basement a voicemail explaining that he likes keeping his investments in one place so it's simple to stay focused on the big picture. However, Josh won't be able to contribute to the Thrift Savings Plan after he retires from the military. He asks: is there a benefit to keeping his money in the account? Would he be missing out on anything if he rolls his TSP over to a Roth IRA?As always, we'll save some time for Doug's trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How do you get to the top of your game? How far would you go to keep your business and personal social groups aligned with your goals? We'll quiz our roundtable, plus get their thoughts on the number one goal they're trying to attain currently. Our contributors this week are Sandy Smith from YesIAmCheap.com; Paula Pant from the Afford Anything podcast; and Len Penzo from the LenPenzo.com blog.After we finish talking about goals and dreams with our roundtable we'll pivot to our interview with Brian Hamilton, the co-founder and CEO of the new digital bank One. There's been a lot of great improvements in the digital banking industry, but Brian found a problem: it was hard to find a good bank that offered all the features someone would want. His solution? Make one. During our fintech segment, we'll dive into the making of One with Brian and talk about good business values, vision, and the digital banking landscape.During today's MagnifyMoney call we'll tackle a question on credit card rewards. Alan tells us he and his wife have been playing the rewards game and got up to $10,000 in 2020. He says it seems like a great side hustle and ask for our thoughts.As always, we'll give Doug some airtime halfway through the show to have this week's trivia game show. If you happen to be knowledgeable on the annual revenues of Wisconsin-based shower head companies, this one is for you.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

We've told plenty of incredible underdog financial stories on the podcast, but none like the one's you'll hear today. More than recovering from 6-figure debt or learning how to balance their budget, today we're excited to bring you the stories of the first black Americans, some of whom survived slavery, but who all went on to become millionaires. Shomari Wills, author of Black Fortunes, joins us today to bring incredible stories of fortitude, challenges and surpassing hardships.We're sticking with the financial "comeback" theme during our headlines. Think you should throw in the towel on the whole financial independence thing because you've made a few mistakes? While you may not have the star power to pay off a $9 million tax evasion bill, like today's headline focus, Mike "The Situation" Sorrentino, your path to independence isn't over because you've wracked up some debt or made some bad decisions. Plus, a big life insurance company just was sold to another. If you're a client, what happens to your policy? We'll describe how it all works on today's show.Of course we'll also throw out the Haven Life Line to a lucky listener AND save time for some of Doug's trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Wondering what the heck is going on with GameStop? We'll dedicate some time to explain everything from the beginning: why GameStop and Robinhood are in the news, what a short squeeze is and how it happens in real-time, why Robinhood (and other companies) stopped investors from buying GameStop stock, and more. Of course, we'll also take on the obvious question: should you invest your cash in GameStop stock?Could the "Work till you drop, I'll sleep when I'm dead" mentality actually be costing you more than you think? After we finish our explanation on all things GameStop, we'll share an interview we loved so much we had to play it for you here. Despite what we may say, many of us love to stay busy. Be it at work, with our personal lives, our volunteering on the weekends: staying on go is good. But, slowing down and choosing priorities with more purpose can have surprising results in your life. Expanding on that point, we'll play an interview between Mike Carruthers, host of the Something You Should Know podcast, and business psychologist Tony Crabbe.During today's Haven Life line we'll take a question from Andrew. He's 26 with an index universal life insurance policy that comes with a hefty $500 premium. Andrew asks us: is it smart to continue paying on this policy for future retirement, or should he close it and look at better options?As always, we'll save some time for Doug's trivia. You'll love it all! We love you! Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Life is about odds, and so are negotiations. How do you stack the deck so that you're "playing to the judge" the next time you're in a pressure discussion, high stakes negotiation, or difficult conversation? Today we're joined by a woman who teaches her students to interview better using many subtle (and not so subtle skills), the Scholarship Shark, Pam Andrews. Plus, Len Penzo has been involved in raise and workplace negotiations for the last 30 plus years, and OG has negotiated a ton with his kids, and sometimes he even wins! They'll all join in with their best tips on how to negotiate better. From what to say to non-verbal cues, we'll share LOTS of important ideas.Nearing retirement and think you'll need some help "landing the plane"? After we part ways with our roundtable contributors, we'll sit down with Rhian Horgan from Silvur, a retirement app designed to help you make better financial decisions leading into your golden years.We'll finish out the show with a MagnifyMoney question from Corey, who wants to build cash flow and long-term diversified wealth. He asks, what are our thoughts on investing in real estate? Corey says he wants his investment to be as passive as possible. Should he look into hard rental properties or REITs? Our roundtable will share their thoughts via Joe. (You'll have to see when you get there). Learn more about your ad choices. Visit podcastchoices.com/adchoices

What do New York City's richest residents, murderous unions, and world-famous guests like Marilyn Monroe and the Beatles have in common? The Plaza Hotel! Julie Satow, award-winning journalist and author of The Plaza, joins us today to share the century of fascinating stories the hotel holds between its walls. From fortunes beyond measure to the Great Depression, from the Golden Age of Hollywood to Home Alone 2, the Plaza Hotel has never been shy about its place in history.Plus, believe it or not, we're about to enter tax season! Tax expert Katherine Pomerantz joins us during today's headlines to share all-new tax rules. Between relaxed guidelines on charitable giving, new deductions for your student loan payments, and more savings than you'd think for your home office, this is one tax talk that'll keep you listening.Cole and his wife are DINKS, and are contributing heavily to their IRAs and Roth accounts. They're planning on semi-retiring early and are looking for some advice on how they can best invest for the long-term, keep money relatively liquid, and have enough cash for living expenses. Thoughts? (And OH BOY, does Joe have some thoughts on this one. You don't want to miss this). Of course, after a short and sweet rant, Cole gets plenty of great advice for the future. Of course, we'll also save time for Doug's trivia, and much, much more. Thanks for listening! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Beyond the big sticker price, New York Times money columnist Ron Lieber has a different mindset than most about college costs. After Ron explains why most of our assumptions on college costs are wrong (that includes you), he'll share three key criteria about what we're really looking for when it comes to higher education. We'll also tackle the no-college route, which comes with its own surprising set of misconceptions that have grown over time. What's the bottom line? There's a whole lot more to think about than the price tag, no matter which path you choose. We'll cover all of the options, threats, and opportunities on today's show.In the financial headlines segment: is the sky finally falling on the stock market? For the twentieth time, NO! Despite what non-stop headlines tell you, the market will drop when it drops. Like Joe says, when it comes to the market, this is one of the few areas in life when doing nothing is the right call. Still, feeling the itch to move some money around? Take OG's advice and try to call the market for the next twenty days. If it works, call us before you do anything else, because we have an offer for you. If it doesn't work, stick to the tried and true and forget about market-timing.We'll finish today's show with a Haven Life voicemail from Susan. She and her husband want to set up a savings account for their grandchild but have a few questions. How can they create a sustainable system for any future grandchildren? What happens if their grandchildren are bad with money? Are there any tax implications to worry about? We'll cover these questions, and more, for a comprehensive answer on setting up your kids for a fulfilled financial future.As always, we'll save some time for Doug's (student-loan-themed) trivia halfway through the show, and much, much more (including some awesome TikTok advice....). Learn more about your ad choices. Visit podcastchoices.com/adchoices

Not sure how to ask for a raise at work? Don't know how to initiate seemingly awkward money conversations with the people around you? This one is for you. Joining us today with their best tips on having an honest, productive dialogue around money are our roundtable contributors: Doc G from the Earn&Invest podcast; Len Penzo from the LenPenzo.com blog; and Paula Pant from the Afford Anything podcast.Halfway through the show, we'll pivot our money conversation towards data and money management with Brian Barnes, the founder of M1 Finance. We love data and graphs as much as the next Stacker (no really), but Brian approaches automation a little differently. Doing our Fintech segment we'll have a conversation on why less is more when it comes to the streams of information you use for investing choices.During our MagnifyMoney segment, our mystery caller asks if they should take on debt to finish their graduate degree earlier or take it a year slower and cash-flow their degree. Our caller assures us that her degree is in high demand. They ask: how do they determine the opportunity cost between waiting or taking on loans?As always, we'll give Doug some time in the spotlight with this week's trivia game-show. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today we welcome the two-time Emmy award-winning host of Travelscope, Joseph Rosendo to the show to share travel tips as we dust off the suitcases and hopefully get ready to hit the road during the latter part of the year. What should we plan to see? Should we try for more or see less? What does he think about travel groups, packing, and learning the language? We'll discuss FOMO, getting to know diverse people, and even having the right mindset on today's show.Plus, anyone who's ever tried to receive an insurance payout knows how much these companies can drag their feet: the tourism and hospitality industry is discovering their pandemic-related claims aren't going the way they'd hoped in many cases. During our headlines, we'll cover what's been going on behind the scenes, and hopefully, leave you with an urge to go recheck your policies for sneaky language from your insurers.During our Haven Life Line, Stacker Steve left us a Stacking Benjamin's BINGO card worth of trigger points, but we didn't let that stop us! Between automatic contributions, NOT getting caught up in a Robinhood rant (only the second time we passed on that opportunity), and pensions - we definitely took the high road on this one.That's not all! Doug shares his own tips on travel points, shares some trivia, and more. It's just another day in the basement! Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices