The Stacking Benjamins Show

Establishing your BEST financial habits means realizing that it isn't about being great today or tomorrow; it's about doing the right things over and over again for the long run. Today we talk to the creator of a documentary specifically about a long run. 3100, Run and Become is the story of an ultramarathon that covers (shocker) 3100 miles. Better yet? It's run around a single New York City block. Sanjay Rawal will take us through the event, his making of the film, and we'll talk about topics that have everything to do with finance. 1) Finding what you love; 2) Chasing a dream; 3) Knowing your weaknesses; 4) Finding your state of "Flow"; and more. The cool part for us? We get to talk finance in a way that you've probably never heard it talked about before. During our headlines segment, another deceased celebrity's estate is an arm wrestling match for the heirs. Sigh. We'll tell you who's fighting for the cash and discuss what YOU should do to foolproof your estate plan from your greedy family. Then, in our second headline, credit card reward programs are everywhere... but just like ice cream brands, they're not all created equal. We'll talk pros and cons of credit card rewards during our second piece. As if that's not enough, we keep bringing it! During our Haven Life Line segment, we'll answer a question from Jason. He's wants to retire in his 40s. If Jason rolls his Roth 401k into a Roth IRA, will he be able to withdraw the cash without the tax penalty? Does the 5 year conversion rule still apply? Then, in our letter segment David is just starting to pay attention to his financial situation. He wants to know what the advantage would be of using a financial advisor or buying funds that have high expense ratios over doing it himself. Couldn't he just do it on his own and save extra cash? We'll surprise Jason with an answer he doesn't expect, and hopefully surprise you, too. And don't you worry, we'll still have time for some of Doug's very special Benjamin Franklin themed trivia. Thanks to Clear for supporting Stacking Benjamins. Get your first two months of Clear for free by going to clearme.com/sb2019 and using promo code sb2019. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What are the absolutely worst wedding gifts you could give this wedding season? One recent article from Kiplinger had us nodding our heads, so Mom said we should challenge our Friday roundtable, including special guest Beau Henderson from the Retirement Resource podcast, to a special game show! While we'll have some fun with this topic, you'll take away some better ideas for wedding gifts, creating a little less waste and a ton less wasted money. Halfway through the show we'll take a break from our discussion on all things wedding related while Joe talks to Anthony Strike, founder of SteadiPay. Steadipay helps users pay off their credit cards in full so that they can use them like debit cards. How does it work? SteadiPay puts an equal amount of cash aside each time a credit card is used, and at the end of the month the app will automatically pay your balance with the amount. Interested in knowing more? We'll get the details from Anthony. And after we let Doug have a little fun with our Friday gameshow-inspired trivia, we'll field a voicemail from an anonymous caller during our Magnify Money call. Our caller tells us they're relatively new to money, and that they're 34 with $300k of savings built up. What's the best plan of action to get started in the world of finances? Thanks to Simple Contacts for supporting Stacking Benjamins. Save $20 on your first Simple Contacts order at http://www.simplecontacts.com/sb and use promo code: sb. Learn more about your ad choices. Visit podcastchoices.com/adchoices

How do you make all of your financial transactions happy ones? How do you introduce the idea of abundance into your life? Ken Honda believes that while money can't make you happy, we DO attach lots of emotions to those bills in our wallet. Why shouldn't we actively manage our self talk around our money? That's the question Ken asks and answers on today's show. We'll talk about gratitude, sharing, making more money, changing your mindset, and creating more "Happy Money" in your life. Plus, in our headlines segment, stock market investors aren't the only one worried about fees...the Justice Department is currently taking a look into the world of real estate and hidden realtor commissions. So, what does that mean to you? We'll discuss how sneaky commissions impact the home buying process for both sellers and buyers. In our second headline, the IRS has announced a higher limit for HSA contributions in 2020. We'll have you covered with everything you need to know by the end of today's headlines segment. Then, after a little break for Doug's trivia, we'll answer Cal's voicemail call to the Haven Life Line. Cal's planing on semi-retiring soon. He thinks he'll use his 401k to subsidize his post 55 years. Is this a solid plan, or is there something he's missing? And during our letters segment we'll tear open some mail from Adrian, who write's in with a some questions about opening up a Roth IRA for kids. Is it true that minors can have an IRA once they earn income? Does that have to be through a W2, or does chore money work too? Thanks to Skillshare for supporting Stacking Benjamins. Get TWO months of courses for free at Skillshare.com/SB. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Allison Schrager is an economist who's studied negotiation, diversification, and also, the topic we'll discuss in today's episode, risk. She'll explain risk using a lens that we haven't seen someone use before...the eyes and actions of legal sex workers. To illustrate how people think about risk, she visited brothels, horse breeders, and, among others, poker players. We'll discuss the many ways we miscalculate risk, how to make better decisions, and what happens when we evaluate the wrong types of risk. And in our headlines segment, we'll call up Madeline Hume from Morningstar. They've completed a report on the state of 529 college savings plans nationally, and Joe and Madeline will dive into the data. We'll talk ab out the latest innovations in plans, plus shine a spotlight on some of the best and worst states to invest your hard-earned college money. Plus, we'll look at one piece describing a shakeup in the online financial planning community that could spell trouble for industry leader Vanguard. In our Haven Life Line segment, we'll throw out the line to Jason, who has some questions for OG about risk parity. Would something like a a 50/50 split between stocks and long-term treasuries a good idea? What are the possible downsides? After we spend some time giving advice to Jason we'll tear open Chris's letter, who has some social security questions. Considering the investments and pensions Chris and his wife already have on the table, would it make more sense to defer taking social security? We'll give our thoughts, but if you're looking for a more in depth conversation about social security you can check our our previous interview with Philip Moeller and Paul Solman. Thanks to Skillshare for supporting Stacking Benjamins. Get TWO months of courses for free at Skillshare.com/SB. Thanks to Simple Contacts for supporting Stacking Benjamins. Save $20 on your first Simple Contacts order at http://www.simplecontacts.com/sb and use promo code: sb. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is there ever a right time to quit your job? At what point do you give up on the current job and take a pay cut to climb a better ladder? On today's show we'll talk career prospects, life planning, income, and more during our headline segment. Helping us out with today's roundtable are our contributors: Mary Wheeler from the Know Debt No Problem podcast, Paula Pant from the Afford Anything podcast, and OG from our very own Stacking Benjamins show. Halfway through the show we'll take a little break from our discussion on jobs (or lack thereof), while Joe talks to Simeon Hyman of ProShares about the market's new exchange traded fund... PAWZ. We've discussed plenty of financial and investment strategies on the show, but this may be the first time we'll discuss a pet care inspired ETF. After Joe wraps up his conversation with Simeon we'll pivot back towards our contributors for our Magnify Money call. JC calls in today with some excited news: he's getting married soon! With marriage on the way, JC also has retirement on his mind. He's 27, and is thinking about playing catch-up with his investments. Is he a little crazy to think about maxing out their accounts despite their income levels? Thanks to MetPro for supporting Stacking Benjamins. Get a complimentary Metabolic Profiling assessment and a 30-minute consultation with a MetPro expert at metpro.co/sb. Thanks to AcreTrader for supporting Stacking Benjamins. Learn more at AcreTrader.com/sb. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What's on your bucket list? Do you talk about your list or have you actually sat down and drawn one up. If not, why not? Today's guest, Karen Cordaway, discusses bucket lists in detail with us. Why you should have one, how to begin, what to avoid, and how to stick to your list are just a few of the topics we'll cover. Even if you're knee deep into building your list (or working through one), there's something for everyone today! And in our headlines segment... how prepared are you to tackle unexpected expenses? We'll cover a piece by the Motley Fool that describes one bill that would bankrupt most Americans, but don't worry, we'll also give some methods on getting ahead. In our second headlines, we'll give our two cents on 10 rules one publication says that you should follow for financial success. We'll throw out the Haven Life Line to Sanjay, who's thinking about putting all of his cash in a single index fund like the Vanguard Total Stock Market Index Fund. Long time listeners of the show probably know where this one is heading. And don't worry, we'll still have time for some of Doug's trivia. Learn more about your ad choices. Visit podcastchoices.com/adchoices

On today's holiday episode we'll remember a great member of the investment community, T. Rowe Price. Cornelius Bond recently wrote a biography on the investing giant, and we'll dive in on the man, the investment philosophy, and how he built one of the country's biggest financial companies. First, in our headlines segment, do you know someone who's graduating this spring? You may want to share today's show with them, because we'll cover what many employers think is the most annoying characteristic of new hires. Think the trait has something to do with slacking off or staring at their phones all the time? The real answer might surprise you. Plus, in our second headline, Uber just completed one of the Learn more about your ad choices. Visit podcastchoices.com/adchoices

What keeps you motivated when you don't feel like thinking about saving more, spending less, or investing better? Do you have words you live by to help guide you through life? On today's show we're calling our friends Brandon Opre from TrustTree Financial, Paula Pant from Afford Anything, and the Len Penzo from LenPenzo.com, to discuss financial quotes that'll keep you motivated. Take this (interesting) freebee from Charles A. Jaffee: "It's not your salary that makes you rich; it's your spending habits." Like that? We have many more in today's episode. Halfway through the show, we'll take a break from the discussion with our roundtable crew to finish our summer holiday travel coverage. To compliment our show from Wednesday with Theme Park Insider's Robert Niles, today Joe will talk with Bethany Bayless, co-host of the Money Millhouse podcast, about Disney tips and tricks she's so graciously decided to share with us. If you'll want to hear more of that conversation make sure to stick around for a few seconds after Doug closes out the show... you won't regret it if you have a trip planned to see a mouse in your future. After we close out of our Disney themed travel guide, we'll hand the mic over to Doug who has some holiday weekend-appropriate trivia. We'll ask our roundtable a very important question: how many billions of dollars did Americans spend on wine last year? Think you have the answer? Remember your answer and see if you could beat our guests on the show. We'll end today's roundtable with a call from Amy, who's going back to school to be a nurse practitioner. While her hospital is paying for some of her expenses and fees, Amy will still have to cough up about $15,000. Should she reduce her 403b contributions to the company match, or take out a loan and pay it back after she gets her degree? Thanks to Proper Cloth for supporting Stacking Benjamins. Get $20 off your first custom shirt at Propercloth.com/sb. Thanks to Ting for supporting Stacking Benjamins! Get $25 off your phone at sb.ting.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Each year here in the basement, it isn't officially summer until we present this episode, which is why we're so happy to bring you Robert Niles, Mr. Theme Park Insider. He's coming down for his annual trip to the basement to help you find your best summer theme park fun. From the best upcoming rides, to fan favorites, plus the best way to get a few discounts from your favorite parks...he's bringing all his tips and tricks to you on this episode. I know! We're fired up, too! And in our headlines segment, where's the best place to save for big purchases like a house or other short-term goals? We'll probably have a few answers that are not exactly what you're thinking. And in our second piece, randomly selected stocks beat out investment picks by fund managers. So... what does that mean for us? We'll cover monkeys, darts, and savings goals on today's headlines segment. Just another day... Next, during our Haven Life Line call, we'll answer a voicemail from Dan, who wants to know how best to allocate his family's investments. He's diversified, but does he really need mid-caps and a total stock market index fund? Plus, in our follow-up letters segment, Steve calls in says that he's invested in large, mid, and small cap... (plus international funds.) Steve doesn't have a problem with his allocation, but is it an issue that it's all through one brokerage firm? You'll get the best of both worlds during today's listener focused segments. And don't worry, we'll still have time for some theme parked... themed trivia. Thanks to Ting for supporting Stacking Benjamins! Get $25 off your phone at sb.ting.com. How about $50 off your first job post? Head to Linkedin.com/sb Learn more about your ad choices. Visit podcastchoices.com/adchoices

Bigger Pockets' David Greene joins us to tackle a more efficient way to buy real estate, especially if you're interested in building a large portfolio of passive income-generating properties. It's called the BRRRR method, and we'll walk through each of those letters on today's show. specifically, we'll talk about how to buy, rehab, rent out, refinance, and repeat. Even if you don't plan on using BRRRR as your strategy, David will share lots of tips on putting your best real estate deals together, finding a great time to help you, and common problems with real estate investing and how to avoid them. And in our headlines segment, are you in a race to reach retirement? We'll discuss one MarketWatch piece that shares 5 hard-earned lessons from people who retired early. It turns out that early retirement (or any retirement at all, is more about psychology than you would think...but it's still about math. Later in the show we'll throw out the Haven Life line to Dave. His mother-in-law wants to invest in his children's college fund. What's the best way to go about that? A 529 plan? Something else? We'll all weigh in on a myriad of options. Then, in our letters segment, Aly's Capital One investment account has been sold to E-Trade. What are the alternatives that she should use? Of course, as always, we'll also make some room for some of Doug's fantastic pre-Memorial Day trivia. Thanks to Proper Cloth for supporting Stacking Benjamins. Get $20 off your first custom shirt at Propercloth.com/sb. How about $50 off your first job post? Head to Linkedin.com/sb Have you read this far? Write us this phrase: OG Stinks! to joe at stackingbenjamins.com to win a #Doug2020 tee-shirt. You can join the brigade of people for responsible leadership! Learn more about your ad choices. Visit podcastchoices.com/adchoices

We all know that subscription costs add up: Amazon, Hulu, Netflix, maybe a lawn service or wine-of-the-month club. But how do you make the decisions which to keep and which to heave-ho? Today our roundtable team, including author Frankie Calkins (author of the new book The Money Resolution, 101 Ways to Save Money, Make Money, and Get Out of Debt in One Year), OG, and Paula Pant (host of the Afford Anything podcast). Whether you're in subscription hell or can't remember the last time you said yes to a subscription service, we'll chat our way casually through all the relevant stuff you need to think about. We heard from you when popular app Debitize went bye-bye, and halfway through the show we'll talk to Thomas Smyth, CEO and founder of cost cutting app Trim. The company recently purchased Debitize, and we'll ask Thomas to give us the skinny on what the future looks like? Why did they decide to buy Debitize, how are they integrating it, and what does the future look like for the new combined company. Of course, we'll then dive into Doug's ah-mayz-ing trivia, but then we'll field a voicemail from the Magnify Money Line from Trent. Trent's been given the opportunity to be a professional athlete. He's currently 23, and has been talking to financial advisors. Their advice is largely the same except in one area: whole life insurance. What's our take on the issue? Looking for something deeper than what we give you on the show? Three days a week not enough? Subscribe to our weekly newsletter: The Stacker. Thanks to AcreTrader for supporting Stacking Benjamins. Learn more at AcreTrader.com/sb. Learn more about your ad choices. Visit podcastchoices.com/adchoices

We can learn a ton from the wealthiest among us, and Veronica Dagher from the Wall Street Journal, and host of the Secrets of Wealthy Women podcast, has a front row seat with some of the smartest and wealthiest people in the country. She'll share with us lessons from three women that easily apply to both women and men. You're going to pick up some great career, money, and life advice on today's show! In our headlines segment we're discussing two different pieces by MarketWatch and Financial Planning. Is it true that the stock market can't be beat? One MarketWatch article claims that what you think you know probably isn't the right answer. And in our second piece, is there a good reason why so many financial advisors are jumping ship? We'll give our take on why advisors are so eager to switch firms. Then in our Haven Life Line segment, we'll field a voicemail from Matt, who's looking to diversify his portfolio. What's our take on pot stocks? We'll also answer a letter from Craig, who writes in about how he is finally debt free and has a paid off home. He's now getting into some pretty aggressive investing and wants some advice on different strategies he has in place. Of course, we'll also make some room for some of Doug's trivia. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Scott Rieckens felt something wasn't right in his life. While he lived in a beautiful corner of the world, and despite he and his wife having fantastic jobs, life just wasn't what he'd expected. So, he did something that few people do...he actually decided to change. The results? He's teamed with Emmy Award-winning director Travis Shakespeare and created a documentary called Playing With Fire, which not only chronicles he and his spouse Taylor's journey toward a better future, but it also explains the concepts behind a movement called FIRE (financial independence/retire early). We'll talk to the makers of the film about how they created the final product. We'll preview the concepts Scott and Travis explain in the movie, and finally, we'll share some details about how and when you may be able to see it yourself. And in our headlines segment Joe will talk to Meredith Ryan Reid about MetLife's new study showing that Gen Y women are behind other groups on both their finances and their confidence in the workplace. Meredith will give us some advice and strategies on what to do when you find yourself falling behind. Later in the show we'll throw out the Haven Lifeline to Katherine, who has some questions on calculating her net worth. Wouldn't paying off debt also lower the amount of cash available to you, in turn keeping your net worth the same? Then, in our letters segment, we'll field a question from Wendy about what she should be doing with her full service brokerage account. She's taken some time to learn about commissions and high annual fees. What's the best plan on moving everything over to a new, low fee account? Of course, we'll also make some room for some of Doug's leprechaun-themed trivia. Just how do leprechauns earn all that gold they hide away at the end of the rainbow? Thanks to AcreTrader for supporting Stacking Benjamins. Learn more at AcreTrader.com/sb. Looking for something deeper than what we give you on the show? Three days a week not enough? Subscribe to our weekly newsletter: The Stacker. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Have you checked your credit lately? How does credit even work? Why do I have a low credit score? Today, Len Penzo, OG, and our special guest Gerri Detweiler tackle credit, credit cards, and hwo to best make your credit score your friend. Halfway through the show we'll take a break from our discussion while Joe talks to Carter Malloy from AcreTrader. When you think investments, does farmland come to mind? On today's fintech segment we'll talk to farmland a viable, attractive investment option. After Joe wraps things up with Carter, Doug will jump on the mic to deliver today's trivia question to our roundtable crew. Before the first transcontinental railroad was completed a coast to coast trip could easily cost $1000 or more. But how much did the trip cost after the railroad connected the two coastlines? Keep your answer in mind... but no cheating! Doug will give us the answer after the roundtable has a chance to get in their answers. After we declare a winner for our halftime gameshow, we'll answer a Magnify Money call from Andrew. Andrew and his family will be moving soon from their paid off condo into a townhome. Should the family use some of their emergency fund to pay down more cash on their townhome, or wait until their condo sells and use that money towards their new home? Looking for something deeper than what we give you on the show? Three days a week not enough? Subscribe to our weekly newsletter: The Stacker. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Erin Lowry from Broke Millennial learned early on about investing. As someone who's VERY conservative and not excited about losses, she didn't want much to do with investing. But, she'll tell us the story today about how she got started and about how you can make it easy. We'll talk about the types of funds to simplify your investment choices, how to add money, and what to do if the market isn't your friend (things start to fall apart). Plus, in our headlines segment, one man who called the last two market downturns says there's another on the way. Should we be preparing for choppy waters? Later on, we'll throw out the Haven Life Line to Larry, whose emergency fund has been drained after a few back-to-back expenses. Should Larry get his emergency fund back to capacity over time, or look towards his Roth IRA contributions to speed up the process? And in our letters segment, Brian has took a side gig delivering food for Uber Eats. After talking to some of his fellow drivers Brain is suspicious that they're defrauding the IRS by not paying any taxes on their earnings. Should Brian steer clear of their advice, or is he just missing out on easy money? As always, we'll still save some time for Doug's trivia...which today is exceptionally epic. Thanks to Ting for supporting Stacking Benjamins! Get $25 off your phone at sb.ting.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices

On today's show, we'll sit down with David Bach, the nine-time bestselling author. What's keeping you from achieving your financial goals? Is it a latte a day? While it doesn't necessarily have to be a latte, our discussion with David will shed some light on the simple things in your life that could be holding you back from reaching your destination. And in our headlines segment, we'll be joined by Ashley Boucher of Sallie Mae. Sallie Mae has released their Majoring in Money 2019 report, and among some of the more surprising discoveries is that some students hold FIVE credit cards. We'll discuss more of the big takeaways from the report during our call with Ashley, along with covering an article from InvestmentNews about Schwab's new portfolio management tool. Later in the show, we'll throw out the Haven Lifeline to Thomas, whose son has gotten all of his college paid for this past year, (with money to spare!) Thomas' son wants to put the extra $3000 into a Roth IRA. Are they allowed to do this, or are there some restrictions that are in place? Then, in our letters segment, Dano has some questions about how he should allocate his retirement funds. With Dano paying a percentage of his money to a pension, wouldn't that be considered his "safe" investment? When Dano is putting money into his Thrift Savings Plan account, couldn't he put all of the cash into the more aggressive funds? Of course, we'll also make some room for Doug's trivia, so don't you worry. Learn more about your ad choices. Visit podcastchoices.com/adchoices

To end our rewind week we present one of our favorite roundtable topics. How do you start saving, when you feel like you can't? I think most people are in this boat, based on statistics about how much money the average person squirrels away. So, here with good facts and humor, were Len Penzo, Hilary Hendershott, and Hannah Rounds. Plus, our friend Shannon McLay was just opening her wildly successful Financial Gym in New York (now she's expanding it all over the USA). We talk to her in this episode about her launch. Here are the show notes from the original episode: What was the best advice someone could have given you when you first started investing? If you're a new investor OR a seasoned pro, you're in luck because our roundtable team are all sharing their best tips today to help get the ball rolling. We're joined by two great guests today (along with the amazing Len Penzo)...host of Profit Boss Radio, CFP Hilary Hendershott AND one of our favorite writers, Hannah Rounds from Unplanned Finances. Not only will we talk about getting started early with your financial plan, but then we'll also tackle problems with brokers and sales incentives. How do you know you won't get burned? Finally, we'll answer a question originally asked of The Moneyologist at MarketWatch.com...what would you do if you found out your mother had taken out lots of credit using your name illegally? Would you turn her in? You'll be surprised by all of our answers. THEN in the FinTech segment, we're actually going to go anti-FinTech this week and talk to our friend Shannon McLay about her new concept coming to a city near you, the Financial Gym. What happens when you give your money a workout? How does it work? Maybe, even though we talk about great ways to use your phone for planning purposes, maybe face-to-face coaching has a place in your planning, too. Thanks to Magnify Money for sponsoring our podcast! Support the companies that support us and help yourself along the way. Learn more about your ad choices. Visit podcastchoices.com/adchoices

I'm personally excited for you to hear this episode. When this first aired I personally was going through some really dark stuff...and as always happens, I found a book that spoke to me and helped me through it. I needed to change. I needed a wake up call. Maybe you do, too. I was lucky that I found Cortney's book and wondered, "Would she come on the show and talk about this?" I'm grateful that she did. Of course, the rest of the episode is a lot of fun, as always. - Joe. Our original show notes: Where do you start when planning your money? Cortney McDermott, the author of one of this year's hottest self-help and business books, joins us in the basement to talk about starting out. If you don't know what you want, how do you know where to go? Yet, most of us don't ask ourselves the right questions to even begin the journey. Plus, we'll also share headlines from the world of financial planning, throw out the Haven Life line to a lucky listener, score with some of Doug's delightful trivia, and more. Huge thanks to Roofstock (check them out for real estate) and MagnifyMoney.com (when you're comparing financial tools like credit cards and savings accounts) for helping us with today's show. They're awesome companies and if you're not using them, I'm not sure you know what you're missing! Learn more about your ad choices. Visit podcastchoices.com/adchoices

The "system" isn't fair. Names from Ray Dalio to Bill Gates talk about income inequality. Poverty is often swept under the rug by people who want to easily dismiss it as "not pulling yourself up," yet most know it isn't that easy. One man who knows very well how difficult inequality can be is John Hope Bryant. He came down to the basement to talk about "getting the memo" in 2017, and we've been talking about it ever since. To kick off rewind week (if you're new to the show, we play favorites for a week after eight weeks of new podcasts), we're excited to re-share this episode. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Why aren't you rolling in the dough? Maybe it's because you aren't focusing on the right parts of your budget. Studies have consistently shown that ONE area of savings beats all others. What is it? Tori Dunlap from HerFirst100k joins Len Penzo and OG to talk about why you aren't saving more money. While you'll learn the top reason why you aren't saving more, you might also have fun doing it.... Halfway through the show we'll take a break from our discussion while Joe talks with Jarrod from the new Easy Profit game. If you've spent any amount of time listening to the show you know that we love the idea of the science of play. So when we heard about a new game that'll teach you how to understand financial statements we just had to talk to the guy behind it all. Then, when Joe's done talking to Jarrod, we'll take some time for Doug's trivia. After a little Disney inspired gameshow fun we'll answer a voicemail from Demetrious, who's been hard at work paying down his loans. While Demetrious wants to keep bringing an extra cash all the overtime at his manufacturing job has been wearing down on his body. Are there some side hustles that he could turn to? Thanks to MetPro for supporting Stacking Benjamins. Get a complimentary Metabolic Profiling assessment and a 30-minute consultation with a MetPro expert at metpro.co/sb. Thanks to Experian for supporting Stacking Benjamins. Boost your FICO score instantly for free. Boost is only available at Experian.com/sb.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Andrew Hawkins was an NFL football player with the Cincinnati Bengals and Cleveland Browns. He also won two Grey Cups in the Canadian Football League, worked in the Detroit Lions front office, starred in a reality television show with Michael Irvin, and starred on Sportscenter on Snapchat...what's he doing now? He's coming down to the basement to talk about how to transition. In his new podcast series, Branching Out (par of the Kneeding Dough series of podcasts if you're searching iTunes), Andrew interviews professional athletes about how they made the transition from pro sports and also what savvy money moves they've made along the way. We'll talk about changing jobs, starting out, building your team, believing in yourself when nobody else does, and more. It's an inspiring interview with Hawk. Plus, in our headlines segment, investors are flocking to buy ZOOM stock... but there's a problem. That's not the company they really want. They're really after ZM stock (from the popular video conferencing company Zoom). Due diligence anyone? And in our second headline, we'll cover one woman's emotional story about creating a "what-if" plan to prepare for the loss of a significant other. Later on, we'll throw out the Haven Life Line to Drew, who is on a student loan repayment plan. He'll qualify for student loan forgiveness in 20 years, but he doesn't want to put all his faith in his loans being forgiven. Should he forgo investing and instead plug away at his student loans? As always, we'll still save some time for Doug's trivia...which today is exceptionally epic. Thanks to Experian for supporting Stacking Benjamins. Boost your FICO score instantly for free. Boost is only available at Experian.com/sb.com. Thanks to LinkedIn for supporting Stacking Benjamins. Go to LinkedIn.com/sb and get a $50 credit toward your first job post. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Doug Lynam grew up in a wealthy family but rejected looking wealthy at an early age and began hanging out with counter-culture kids while trying hard to find himself. From that lifestyle to the Marines and finally to becoming a monk, we'll talk about Doug's quest to find himself and ultimately to come to grips with the role of money and what it meant for him (and also for many of us). We'll talk through stories about his quest, how he began helping his fellow monks with their money, and ultimately how he became a money manager. He'll also share strategies to help you begin building your financial knowledge, to start questioning your own view of money, and to ultimately become a better steward of money. It's a wide-ranging, fun discussion, and we hope you're able to join us for it! In our headlines we'll talk to Paul Yakoboski, Senior Economist at TIAA Institute, about the results of the company's 2019 Personal Finance Index. He'll share how education and juggling your financial life are closely related. We'll talk about trends with the P-Fin index, the roll of education in your game plan, and more. He'll discuss how to gain knowledge about money and how to become better handling financial concerns. Plus, another company is planning an iPO. No, not an IPO (initial public offering), but a more made-up term called an iPO. We'll explain today. Later in the show, we'll throw out the Haven Lifeline to Alan, who has an awesome question for us about pensions. He has two choices: one where he can take the full amount himself or another where he gives up $400 per month but his spouse is also covered for her life. Which does he take? Then, in our letters segment, Dillion writes in asking about the best way to transition into the field of personal finance. He's currently an accountant, but Dillion's realized his passion is in helping people learn about and gain control of their finances. What's the approach to moving into the personal finance field? Of course, we'll also make some room for Doug's trivia, so don't you worry. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What happens when a bride and her mom spend $70,000 on a wedding and everything goes wrong? Here's a bigger question: What happens when you spend more to get a bigger, better experience and it completely goes awry? Is it better to "super size" your spending to find more joy? We're all about the correlation between happiness and spending on today's episode. We're shaking things up with today's roundtable guest because joining us in today's discussion is Bobbi Rebell, host of the Financial Grownup podcast AND co-host of our very own Money in the Morning show. Plus, we'll call up Paula Pant of Afford Anything, and Len Penzo from LenPenzo.com. After a crazy Game of Thrones meets Len Penzo inspired trivia from Doug, we'll answer a voicemail during the Magnify Money call. Reed asks about an article he's read on retirement. According to the piece, there's a lot of "front-loaded" spending in retirement, which could drain cash savings a lot quicker than expected. We'll give our take on retirement, spending, and planning in our response to the piece. Thanks to Clear for supporting Stacking Benjamins. Get your first two months of Clear for free by going to clearme.com/sb2019 and using promo code sb2019. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today we're all about your letters. We'll start with a question about moving funds around to avoid some taxes, jump into helping a 25-year-old decide whether to max out his retirement accounts, answer a question about robo advisors, and then launch into helping kids with money, how to save for a house, and more. In our headlines segment we'll talk to Joe Jiminez from The Alternate Life podcast. Maybe you've had the urge to quit your day job and go on a journey, but few of us have actually followed through. Joe Jiminez dumped the job and spent his summer walking the Continental Divide Trail. We might not be able to take the summer off ourselves, but we'll at least ask Joe what it's like. Then later on, we'll throw out the Haven Life Line to Reggie, who's heard on the show that OG isn't particularly fond of Betterment or Wealthfront. Reggie has a bulk of his money in Wealthfront and Betterment, so he's wondering...what's the issue? As always, we'll still save some time for Doug's trivia...which today is exceptionally epic. Thanks to Proper Cloth for supporting Stacking Benjamins. Get $20 off your first custom shirt at Propercloth.com/sb. Learn more about your ad choices. Visit podcastchoices.com/adchoices