The Stacking Benjamins Show

There's a time-bomb waiting in your IRA. Tax and IRA expert Ed Slott joins us today to share what the death of the Stretch IRA means for your retirement, and how the SECURE Act has made some big changes to the way your money is treated long after you're gone. Whether you have a partner, children, family, or any other dependents depending on your support, the last thing you need is complicated tax rules funneling money out of your portfolio. If you're the type of person who runs at the sound of a tax discussion, you may want to stick around for this one. Ed Slott breaks down what is often a monotonous subject into funny, easy-to-understand material. GME Resurgence, Cathie Wood, Stocks, and more. What in the world is going on with GameStop? No, that's not a misplaced sentence. Did you think the move three weeks ago was the end? Check the chart and be prepared for a surprise. Joining us today to talk GameStop's second resurgence, we welcome Spencer Israel from Benzinga. We'll also discuss Cathie Wood, the CEO of the largest actively-managed ETF in 2020 (among other distinctions), the bouncing markets, stock picks, and more. Uber (and any other service-economy app company) is NOT Your Friend. We normally make light of a financial TikTok on our Monday shows, and while we aren't changing that today, we're also shining some special light on one emotional video you've probably seen making its way across the web. Featuring a tearful Uber driver sharing his ordeal delivering almost an hour-long order only to ultimately make virtually no money on his delivery, the driver pleads with customers to understand what drivers go through and to tip appropriately. We agree with the driver on a big point: regardless of how you may feel about the current system, it is the system. If you're utilizing service labor, you need to tip appropriately or choose other manners of getting your product/need met. BUT, we use the video to shine an important light here. Uber's first priority is to the company shareholders, not to you as a customer or contractor. Great guests like Juliet Schor have already explained the how's and why's behind the large costs associated with the everyday worker in the sharing economy, but one's things for sure: when something isn't working for YOU, it's time to pivot. When is it the right time to make the leap to full-time business owner? We'll finish today's show with a Haven Life voicemail from caller Evan, who has some questions on jumping ship from the W2 life to full-time business owner. Up to this point, Evan and his family have reinvested all the money back into the business to keep it growing, and he asks: what should he know before taking the leap? Joe and OG give their two cents, and share a few resources along the way. Of course, we'll always leave some time for Doug's trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

No matter if it's 2017 or 2021, $1 million dollars is still a nice stack of Benjamins. That's why to finish our rewind week, we're bringing a round table episode featuring our contributors sharing their top strategies to save your own million. Regular contributors Paula Pant and Len Penzo were joined by Hip Hop's Financial Advisor Rob Wilson on this episode. You can read the original show description below: How do you save a million dollars (we said in our coolest Austin Powers voice….). We’ll discuss a recent online piece that goes over that on our Friday round table! Special guest, and Hip Hop’s Financial Advisor Rob Wilson joins Paula Pant and Len Penzo in a no-holds-barred conversation on saving more money. Of course, we don’t stop there. We also tackle a recent Time story about millennials. Apparently, ONE trick is helping them save more money. We’ll share not only what it is but also additional tricks to save more money. Finally, we review a Moneyologist column question about taking care of a brother’s money. If he can’t do it himself, how much should sister step in? In our Friday FinTech segment, we talk to the CEO of GO, a cool app that’ll help you more quickly (and by more quickly, we mean WAY more quickly) your car insurance. It’s as easy as taking a photo…. Learn more about your ad choices. Visit podcastchoices.com/adchoices

For many families college is right around the corner, and so is that first Business Office payment. Fortunately for you, we have some great advice on hand from a financial aid wizard. While specific policies may change, the strategies and mindset behind lowering the bottom line and getting more aid in your pocket tend to stick around. That's why we're replaying our interview with financial aid wizard and UC San Diego instructor, Jodi Okun. Here's our original description: College planning expert Jodi Okun stops by the basement to help college-bound students save a TON of money. She has advice for students, parents, and for people thinking about possibly going back to college. How will you pay for it? She has many great suggestions. In our headlines....beware when an expert shares their opinion, and it just happens to correlate with EXACTLY the items they sell. Plus, ever wonder why nobody makes money in the stock market? We'll share the real reason. Then we take a hotline call from Amy about moving to Canada and a letter from Megan with an awesome article attached. All that and a guy named Snoop! in the basement today.... Learn more about your ad choices. Visit podcastchoices.com/adchoices

With stimulus checks hopefully on the way, it's a good time to get your debt payment strategy in place. That's why we're replaying this episode from 2019 with Laura Adams, more commonly known as Money Girl from the popular podcast by the same name. Here's the original description: Are you having trouble climbing out of debt? Or maybe you're tired of daily calls from debt collectors? Whether you have serious debt or just need to refresh your plan, today we're kickstarting your 2019 journey to financial independence with the host of the Money Girl podcast, Laura Adams. Plus, speaking of 2019, what does the next year have in store for the world of credit? We're talking to Senior Vice President of Research and Consulting at Transunion, Matthew Komos, during our headlines segment. And later on, we'll throw out the Haven Life Line to Alex, who wants to know if he should pull some cash out of his account and reinvest when the market drops. He's also finishing his residency to become a physician, and his tax liability is virtually zero. What should he do with his accounts right now? And don't worry... we'll still take some time for Doug's trivia. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Whether you've been investing for a week, for years, or anything in between, it's always a good idea to keep the fundamentals in mind. BUT....on the other hand, we love to have fun, and it's Friday after all! That's why today we're treating you to a Stacking Benjamins game-show version of "Guess the 10 Habits to Become a Better Investor!" We pulled a piece from M1 Finance listing their top 10 habits, and on this episode, we'll quiz our contributors on which strategies made the list. Not only do you get great investing tips from each of our three contributors, you'll find yourself laughing so much you won't realize you've learned a thing... until it's too late. Playing the game-show with us, we welcome Don McDonald from TalkingRealMoney.com, Paula Pant from Afford Anything, and Len Penzo from the LenPenzo.com blog. Think it's too late to make a career change? After we crown our game-show champion, we'll talk big career moves with the Evil HR Lady, Suzanne Lucas. Are you anxious about making an industry change? Think you've sunk too much time to make a move for your happiness? We'll talk sunk costs (both monetary and emotional), following your happiness, and the realities of leaving behind a career you've spent a considerable amount of time in - and the truth is probably brighter than you think. What should you do with you investments when you have large upcoming purchases? We'll finish our show today with a MagnifyMoney question from caller Debi, who tells us that she's looking to buy a home or condo in the next few years. She would like to acquire a few more properties after that and start to rent them out for passive income. Plus, she has a $10,000 savings bond that will mature in August 2021, along with another $10k each in savings and Robinhood. Our contributors give Debi some much-earned congratulations and advice on how to best position her money in the mean time. As always, we'll save some time for Doug's trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

John Warrillow has built and sold many businesses, and has created a business value builder system used by thousands of businesses worldwide. With many, many years of experience under his belt, John knows a thing or two on how to bring value to a business. Today, he brings that wealth of knowledge with him to help make better financial sense for your family. Tune in for an insightful discussion featuring case studies, interesting stories, and maybe a new way of looking at your family's financial picture. Hot take incoming: every time you make a bad financial decision and lose big (let's say shorting GameStop to the tune of $200,000), maybe you should blame someone else and sue them to recoup your losses! Sound crazy to you? Tell that to Christian Iovin, the man suing leading Reddit investor "DeepF$%kingValue" over his part in the short squeeze. During our headlines, Joe and OG give a thorough deconstruction detailing how the "get-rich-quick" mindset can lead a person down some strange paths - including thinking that a social media figure is responsible for your investing choices. While we aren't without sympathy, we break down how Iovin willingly made his choice on what he thought was a great deal at the time, and offer up some sound advice to not get yourself caught between a rock and hard place - short squeeze or otherwise). We'll keep today's theme going with our second set of headlines. Bill Gates is now officially "meh" on Bitcoin (it's an improvement!), and financial advisors are ready to back the truck up to crypto. Now hold on a second if you think you know where this is going. We're not here to preach #teamcrypto or denounce the movement either way. What we are saying, like in our interview with John Warrillow, is that you need systems. We've said the same thing about Tesla and Apple, and the rules don't change for Bitcoin. The biggest danger to your portfolio isn't a Redditor or Capitol Hill, it's you. The best thing you can do for your bottom line is taking yourself OUT of the equation. Enough of that, moving on. Finishing out today's show is a Haven Life line question from Zac. He asks... (checking notes...)... is putting $20 a week into a somewhat random stock that has shown positive growth a good idea? Truth be told, we could have went a lot of different ways with this one. I'm proud to say the guys put some thought into this one, and not only give Zac an answer, but dive into some explanations on different stock analysis theories. Of course, Doug always gets some airtime for his trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What's the next step after you finally "make it"? While it's easy to scoff at the problems of people who are financially set, it's not uncommon to lose a sense of purpose once you jump out of the rat race. Bigger questions start to come up: what's your real purpose in life? What type of legacy are you leaving behind? How will your personal relationships be impacted by your new-found financial status? What type of impact do you want to make on the world? Shining a new light on these ideas that often don't receive enough attention is Jennifer Risher, author of We Need To Talk: A Memoir About Wealth. We'll talk to her today! Taxes, taxes, taxes. It's that time of year again. Joining us to talk all things taxes during our headlines segment, we welcome tax software expert extraordinaire, Hannah Rounds from The College Investor. Whether you're a landlord, charitable giver, paying off college debt, contributing to an HSA, or anything in between, Hannah has great advice ensuring you won't be leaving any cash on the table. Plus, Fidelity recently held an AMA (ask me anything) on Reddit. The thread gathered A LOT of attention, but not for the reasons you'd think: everyone had Robinhood on their mind. While Reddit users did comment on the GME/Robinhood debacle, there was a bigger question: why in the world does Robinhood have such an incredible user interface, while many of the other big-name brokerages and bank apps seem to be stuck in the first episode of Wandavison? We'll finish out the show with a Haven Life line question from one listener who has finally come to their senses with Robinhood. Listener Taylor has invested with the company for years and he's ready to jump ship. The big question? How can he change move his investments to another brokerage without taking a big capital gains hit? We'll give him many options so he (and you!) can move on to greener pastures. Naturally, we'll also give Doug his airtime halfway through the show. FAANG stocks used to be all the rage, but some investing pros are looking to the future and is giving one company the boot. Find out which one during Doug's trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Feeling stuck? Maybe it's time to move. Of course, it's a lot easier to write about moving than actually planning and doing it. And while a move may pay off in the long run, there could be a hit initially to your finances. With that in mind, today we ask our round table contributors: what exactly would encourage you to move? Better location? Pay? Maybe you want to escape the harsh Detroit winters? (I'll let you guess who had that complaint). It's a fun conversation that covers a breadth of topics in true Stacking Benjamins fashion. Helping us out today are our round table regulars: Paula Pant from the Afford Anything podcast, Len Penzo from the LenPenzo.com blog, and our very own OG. Halfway through the show, we'll give our contributors a break while Joe talks everything alternative investments with Michael Weisz, co-founder of alternative investments company Yieldstreet. During their interview, Michael covers everything from the company origin stories - a shocking reality check that a large percentage of everyday consumers were locked out of the alternative investments sector - to helping investors by cutting down average IRA rollover times from forty days to six. If you've ever wondered about other investment choices outside of stocks, bonds and funds, this is one interview for you. We'll end today's show with our MagnifyMoney segment. Caller Kevin tells us that his father passed away last year. While he isn't attached to the credit card debt his father left behind, he's heard the horror stories of banks hounding family members after a loved one's death. Kevin asks: what's the best strategy for dealing with the looming creditors? We'll give Kevin some heartfelt advice that we hope can make this time a little easier. Of course, we'll give Doug his airtime halfway through the show, and he's keeping things Texarkana Classy with today's trivia. Learn more about your ad choices. Visit podcastchoices.com/adchoices

How do you have money conversations with the people in your life without making things awkward? From asking the boss for a raise to having a tricky money chat you'd rather not have with a family member, and even to opening honest lines of communication with your partner - money can be a scary topic to broach. We bring good news: it doesn't have to be. Erin Lowry, the mind behind the Broke Millennial series, joins us today to share how you can move beyond the "pit in your stomach" feeling when it comes to money conversations, and the answer (really) is easier than you'd think. Plus, during our headlines... let's just say the local Texarkana Chamber of Commerce isn't too happy with how we've been portraying the small quaint town of Texarkana. Chamber of Commerce President, Bubba "Tex" Mext had a few words he wanted to share with us, and - lucky for you - we caught it all on tape, and we're sharing it here today. Of course, we won't leave you high and dry either. When we find some clean airtime, we'll also discuss a piece about the growing popularity of HSAs. While the book is still out on investor sentiment towards a dual HSA/401k investment approach, it's not the worst idea to consider for your larger financial portfolio. We'll explain why during our headlines. During our Haven Life Line, we'll answer a call from Maz, who has more questions about the GameStop situation. What are the big lessons to take away here? What should investors have learned? How can people do better in the future? Naturally, Doug can't let Tex Mext make so much commotion without having a few words on the matter himself. Better brush up in your Lone Star knowledge, because Doug has Texas on his mind today during his trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Think you can't network like a pro because you're an introvert? Better put your party hat on and take a shot of liquid courage, because our guest today is coming in with strategies and techniques that'll turn anyone into a lean, green, networking machine. (Without resorting to sending out hundreds of spam emails). Our guest, Matthew Pollard, has helped multiple businesses become million-dollar ideas, and he assures us it has a lot less to do with having the skills of a smooth talker, and a whole lot more with honest connection and preparation. Having trouble with the law? While the long arm of the government may be able to seize your bitcoins, today's piece shows that by forgetting a key piece of information, you don't have to worry about your bitcoins ever really going goodbye - but good luck cashing anything in for your retirement. Plus, we'll cover why everyone's favorite mortgage strategy, velocity banking, is an off-the-rails fun way of paying down your debt... until it all comes crashing down around you. Plus, during our Haven Life line, Justin tells us he's interested in buying stocks for his daughter. Her favorite game, Roblox, is about to go public, but the company is doing a direct listing. Justin asks: Are direct listings as bad as IPOs for everyday investors? Is there anything he should know about before getting involved? We'll give Justin the rundown, and even throw in a few of our favorite apps to get kids started on investing. As always, we'll save some time for Doug's network-based trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Love is in the air, and today, no matter your relationship status, you're gonna LOVE our discussion on your relationship with money. How is it? Is it healthy? Growing? Worrying? We'll discuss all of the emotions around money on today's show, featuring a cast of financial media peeps including Paul Ollinger from the Crazy Money podcast; Paula Pant from the Afford Anything podcast; and our very own OG. Plus, just in time for Valentine's Day, there's big news from the financial app for couples called Zeta. The founder of Zeta, Aditi Shekar is back, to share all of the details. If you have a relationship with someone AND you're trying to mix money in any way, you'll want to hear their news. Of course we'll still all have opinions for a lucky listener on today's MagnifyMoney.com call AND we'll battle it out over Doug's Valentine's Day themed trivia question. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

Ryan Harris has had a front row seat to stress. Over a 10 year career in the National Football League and 4 years as a starting lineman at Notre Dame, he played in plenty of "this is the most important play of all" situations. Now on a quest to help empower people to embrace better financial habits, the former Super Bowl 50 winner joins us today to talk about how to fight stress and how to live with doubt. He'll also share his own story of making plenty of money but still not possessing the systems to hold on to cash. Should this week's changes on Capitol Hill have you worried for your wallet? I won't even make you wait on this one - THE ANSWER IS NO! During today's headline segment we'll tackle a piece stirring up some unfounded fears that your personal finance "hangs in the balance" over the government change in Washington. You should never stick your head in the sand, and ghost the financial markets over the (D) or (R) in your politician's name. Don't take my word for it... just wait for Joe's rant. We'll also share our thoughts on Tesla reaching a 2 TRILLION dollar valuation in two years, and all the reasons that shouldn't matter at all for your portfolio, even if your friends say otherwise. Plus, not sure if you should pay off your home early? During our Haven Life Line we'll answer a voicemail from one listener weighing the pro and cons of paying off a mortgage on a house they'll only live in for another five years. They ask, should they instead save their extra Benjamins for the next move? Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

We're all tired of hearing about what a "dumpster fire" 2020 was. How do we reboot the computer, restart the machine, refresh the situation, and re-fire our financial engine? That's our topic today, and OG, Paula Pant (AffordAnything), and special guest Roger Whitney (Retirement Answer Man) all have helpful ideas about getting back on track. Halfway through the show we're excited to talk to our old friend (and Joe's co-host on the Money Tree podcast), Doug Goldstein. Doug's created a constant happiness journal. If you've been waiting for the perfect journal to have a more happy 2021 and beyond, Doug will share with you why he created this, how to best use a journal, and why journaling works for so many people. Finally, on our MagnifyMoney.com question of the episode: Jon is thinking about college costs for his four kids. He's heard the Stacking Benjamins expert, Pam Andrews (the Scholarship Shar), say that a HELOC, or equity in the home, can't be factored into the FASFA. Jon's kids are in private school and have to do something like FAFSA. Jon has $60,000 in savings and is thinking about putting two-thirds of the savings into a HELOC, to possibly get financial aid. Thoughts? Learn more about your ad choices. Visit podcastchoices.com/adchoices

How do you balance getting what you want now without mortgaging your future? Or on the other hand, how do you avoid have ZERO fun today while you prep for a rosy tomorrow? We often recommend that you look at your situation as if you're a business, and today we'll talk to a man who led one business to amazing results, the former CEO of Honeywell, David Cote. Plus, the cryptocurrency market value has topped $1 trillion, with Bitcoin now worth over $38,000 a coin. Feeling the itch to jump into the Wild West of investing? We won't stand in your way, but we do have a few stories about us selling a coin or two... WAY before we should have. In our second piece, is paying to improve your credit a smart play? We'll discuss everything from good habits to shady house financing, automation, and The Big Short. Should you be paying taxes on your unemployment? Mike called the Haven Life Line after he noticed there were no taxes automatically deducted from his two months of unemployment. Should Mike worry about the IRS coming after him later? We'll answer that question, share Doug's trivia, and we'll be skeptical about exactly how many people actually listen to the podcast. Is it really two or maybe only just mom? Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Know those people who say you need a 4-year university degree to reach success and financial independence? Our guest, Myra Oliver, has a thing or two to say about that. She's worked as a hairstylist, real estate broker, and now is our resident financial coach on today's show. Myra knew she didn't need a degree to reach her goals of financial freedom. Today Myra will share her story about working hard toward success. She shares stories about how she learned quickly how to bring in more money, how she manages real estate, surrounding herself with the right people, and how she and her husband were able to retire from their traditional jobs by age 33. "You have to do what others won't, to get what you want." - Myra Oliver's mantra. Plan on leaving something behind for your loved ones? Get your financial house in order first. We recently covered how former Zappos CEO Tony Hsieh passed away without a will, but you may remember Prince also didn't have a will. (Yes, we also talked about Prince way back in 2016). It turns out, that case is still ongoing, and the IRS believes Prince's estate owes over $32 million in federal taxes, based on a new valuation. During our headlines, we'll give you plenty of reasons to get your legacy in order today. Plus, can you make 2020 Roth IRA contributions until Tax Day 2021 if you're already paying taxes for the new year? Stacker Josh calls in today with a voicemail for the Haven Life Line telling us he'd rather get it right now than have to deal with the IRS later... can't fault him on that logic. As always, we'll also save some time for Doug's trivia, and much, much more. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today we stay focused on goal setting. We're turning our attention to our group of financial media members and asking them how THEY are achieving their own goals. They'll share how they communicate, hold family members accountable, and stay on track. Joining us today is special guest and host of the Seven Figures podcast, Sandy Waters; Paula pant from the Afford Anything podcast, and Len Penzo from LenPenzo.com. Halfway through the show, we'll give our contributors a break while we sit down with health and wellness expert Angelo Poli from MetPro.co. With the holidays over and the new year here, Angelo has some great tips to fatten up your wallet while you trim down the waistline. How are you going to grow your net worth without a healthy body to keep you focused on the prize? We'll share how. Plus, how can early retirees make sure they have enough reserves in the bank to take care of emergencies down the road? During the MagnifyMoney segment, our contributors drop some knowledge for Laura, who called in asking about preparing for early retirement with a preexisting condition. Plus we'll save time for all-new game show trivia from the big man himself, Doug. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices