The Stacking Benjamins Show

What lessons can you learn from an entrepreneur in technology who was hired just after the turn of the century to lead one of the biggest exchanges on earth? A ton, it turns out. We talk to Former NASDAQ CEO Robert Greifeld about making tough choices, developing leaders, listening, debating, and more. He'll also share stories about his interactions with CEOs like Bill Gates, Howard Schultz, and Jeff Bezos, and his view of the 2007-2008 financial crisis from his front row seat. You'll learn a ton from today's show whether you lead a company, department, club, or your family. Plus, during our headline segment, wealth advisors give clients high marks for understanding some tax rules and for saving money. However, there are some glaring weaknesses they see among clients. Do you have the same weaknesses? We'll explain what worries financial advisors and how to correct course. In our second headline we'll wave the warning flag on an IRS rule that many people violate, and regret later. We'll show you HOW to avoid getting hit with penalties and help you smooth the road for your retirement at the same time. Later we'll throw out the Haven Life Line to Mark, who not only tries to avoid giving us his tee-shirt size on air (and nearly fails), but also wonders if it's a good idea to lock much of his emergency fund in a high-interest paying but long-term CD. ...and of course, we'll save some time for Doug's trivia. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Visit any online forum and you'll find someone complaining about their health insurance costs. While lots of people complain, our guest today says that the answer may have nothing to do with all of the political rhetoric around the topic. Scott Heiser visits the basement to teach you how to become a better "health" consumer. Changing the healthcare system is one thing, but making proper, well-informed choices about your personal health is another (and one that we can all handle--and also use to bring down the cost of your care). We'll discuss everything from comparison shopping your professionals, insurance options, medical tourism, HSAs, and lots, lots more. Plus, during our headline segment, there's huge news in the financial brokerage space. Charles Schwab is buying TD Ameritrade! With Schwab acquiring another 12 million client accounts, and over a trillion dollars in assets, what's this mean for the bigger financial landscape? Could more mergers be on the horizon? We'll tackle the big questions before we scale it back down during our second headline. One gamer spent over a million dollars on a video game character only to have a friend sell it for $643. Sounds crazy? We thought so too. Later we'll throw out the Haven Life Line to John, who's looking for some pointers on how much he should be contributing at work. Of course, we'll save some time for Doug's trivia. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Wondering if there are any good games you can play about money or economics? Long time Stacking Benjamins fans know we have one non-financial event that gets us just as excited (if not more) than any other event all year: our annual board game episode! Today we'll fly with Joe to Dallas, Texas, and the BoardGameGeek.con convention, where he catches up with the star of the YouTube show Game Night!, Lincoln Damhurst. They'll not only talk about a whole host of cool games about money and company-building, but they'll also dive into some light, fun games that you can play with the family over the holidays. Before you waste money on a game that nobody will like, check out this episode and make a better buying decision. Plus, replacing our usual Fintech segment (is it boardtech now?), we're talking to co-creator of a new site called FindYourMeeple.com. Jeremiah Cole-Kelly will walk us through how this new tool can help you find a cheap evening's entertainment (and even a weekend's worth, when it comes to game conventions). Looking for people in your area who love to play board games just as much as you do? Jermiah's site just may be the solution to your problems. Of course, financial show or not, we'll always save some time for Doug's trivia. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What are the hottest deals in tech this holiday season? What should you avoid? Back for her annual visit to the basement, Bridget Carey from CNET shares the highs and the lows this year. There are LOTS of deals you'll want to avoid, and she'll name names. But don't worry, if you're thinking about televisions, computers, game consoles, kitchen gadgets, audio equipment, or security, we've got you covered! Worried about the financial tasks you need to accomplish before year-end? Maybe you should be. Today we'll also share a laundry list of important items you'll want to check off your list before the new decade begins in just over a month. Plus, we'll also share some advice about gift giving. Since we're diving into shopping season, how do you give a gift that won't be returned? After a little dose of Doug's trivia, we'll wind up the show by throwing out the Haven Life line, as always. It's just another fantastic, money-saving episode of Stacking Benjamins on tap! Enjoy. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Plus, if you're an investor, the game just might be changing. In our headline segment, we'll share news about three big firms who just received the green light to hide holdings inside their ETFs. What does that mean? We'll share why that may be a big win for active managers, and maybe also for you. Plus we'll cover a second piece from MarketWatch about shopping for yourself. People already spend surprising amounts of cash on themselves each holiday season, but by doing it the right way, you'll be further ahead by maybe partaking in a little selfish gift-giving yourself. Later, we'll throw out the Haven Life Line to Julien, who has been reading about income taxes going on. He'd like to know if there's any truth to that claim, and if so, how should he be balancing contributions between his Roth and Traditional 401ks? Of course, we'll save some time for Doug's trivia. It's the start of our Thanksgiving week extravaganza of shows, and we can't wait for you to hear it, so jump in! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Think you're underpaid? You aren't alone. Are you even sure how much you should be earning in your position? On today's roundtable we'll discuss one piece examining all the ways you can mess up the driver of all of your financial activity: your salary. Whether you work for "the man" or for yourself, we'll have something for you. Helping us out today is special guest and Stacking Benjamins friend Katie Brewer, from Your Richest Life, Len Penzo from LenPenzo.com, and OG from our very own podcast. Plus, halfway through the show, we'll take a break from our discussion while Joe sits down for another chat with Angelo Poli from Metpro. It's not exactly Fintech, but keeping a mind on health tech will keep you healthy through the holidays... which keeps money in your pocket. During our Magnify Money segment we'll answer a voicemail from Jordan. Jordan and his wife are doing great in their savings and investments, and would like some advice on the best way to tackle asset allocation. As always, we'll carve out some time for a little gameshow with Doug's trivia. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wonder HOW you can finally get ahead? While some people moan that they just can't seem to make ends meet, Craig Curelop worked from the opposite strategy: he realized that EVERYTHING is for sale. Today we'll talk to the 24 year-old who's hacked his house, his car, and more to get ahead. He's biked to work, slept on his couch...and his old boss said he'd even rent you his underwear. Craig shows us all how we can get ahead if we're willing to go the extra mile. Plus, what funds have had the worst returns in 2019? We'll share the list, which is interesting (to say the least). Not only that, but we'll also watch OG maybe throw up in his mouth as we tackle target-date funds. New information shows that maybe the big brokerages know these tools are broken...or at the least, suboptimal for many people. That's not all. Of course, we'll also finish out the show with some of Doug's absolutely amazing trivia! It's gonna be fantastic! Hit play already! Learn more about your ad choices. Visit podcastchoices.com/adchoices

While everyone else panics about student loans, what if YOU were able to reach your dream of a great education and ZERO debt? Wouldn't that be awesome? You're going to love our featured interview with Anthony ONeal, author of Debt-Free Degree and Dave Ramsey personality. Between fantastic advice on choosing the right school, lowering your tuition amount, and earning scholarships... Anthony has a plethora of actionable steps you (or anyone else you know) can take to graduate with a degree, but WITHOUT being shackled to loans. Buying a car? In our headlines segment we'll talk about the HUGE number of people who are "underwater" on their auto loans. Maybe that's the new epidemic. We'll talk about how to handle auto loans much more effectively, plus, we'll also talk about one new piece pushing the claim millennials should be happy that they're stuck renting their house. We'll do a dive into today's pieces and naturally give our two cents as well. Later we'll throw out the Haven Life Line to Kathy, who has some questions on the differences between two savings accounts at her bank. Kathy thought she should be earning more on her savings, but it turns out her bank actually has two different versions of their savings accounts, and she's been putting her cash into a lower-earning account. What's the deal with that? As always, we'll save some time for Doug's trivia. Learn more about your ad choices. Visit podcastchoices.com/adchoices

We've all had those days. Nothing went right at work and on the way home you KNOW you'd feel better if you just stopped at the (insert favorite store) and bought...that expensive (or inexpensive thing). On Instagram, that's often called self-care. But is it destructive? In a recent viral YouTube video, Chelsea Fagan of The Financial Diet lays out her thoughts. We'll play a clip and then jump into a fascinating discussion on the topic with Jacob Wade, from IHeartBudgets.net, and basement regular Len Penzo, of the LenPenzo.com blog. Whether you own a business or are thinking about starting a side hustle, one problem we KNOW you'll have is handling your books. How come current bookkeeping and business management software programs don't work together? A company working at solving that puzzle is called Roger.ia, and halfway through the show, we'll take a break from our discussion to talk to Catherine Anderson, the cofounder of Roger. Catherine will walk us through how Roger does everything from fraud detection to team management, bill pay, and how it even helps out with possible audits. During our Magnify Money segment, we'll answer a voicemail from William, who will be retiring soon. William and his wife are still paying on the mortgage, but they have some savings they could tap into. Here's the question: Should William use their extra savings towards the mortgage, or keep the cash liquid as an emergency fund? We'll answer Will's question and still save some time for Doug's trivia. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wonder why you don't reach any of your goals? Tom and Ariana Sylvester were there. Over $70k in debt, newly married...they needed a plan. BUT more than that, they needed a way to STICK TO their plan. Today they join us in the basement to share the method they've used to achieve some amazing goals. In our headlines segment, we'll discuss a possible merger between two big companies. What happens when you own shares of a company and it's swallowed by another? What happens if the company whose shares you own devours another? We'll use this current news to discuss how mergers work from the viewpoint of a shareholder. Then, after a little dose of Doug's trivia, we'll wind up the show by throwing out the Haven Life line to a lucky listener, as always. Today's question? Is Social Security going to go extinct faster if younger people join the FIRE movement? Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices