The Stacking Benjamins Show

Should you take on debt to buy real estate? Does the stock market really return as much as we're told it after a life of saving and investing? And on the topic of stocks... how should a portfolio be split up between small, large and foreign stocks? That's just a sneak peak of the broad range of question and answers we're discussing on today's jam-packed letters episode. During our headlines segment, OG is sharing his thoughts on Warren Buffett's Berkshire Hathaway letter to investors. Plus, we're calling 1(800)Accountant CEO Mike Savage. What's the deal with this year's tax refunds... or lack thereof? After some unusually fantastic trivia by Doug, we'll throw out the Haven Life Line to Luke, who is getting his master's degree this fall. With his tuition covered, plus a stipend of $1400 a month, should he try to max out his Roth IRA before school starts, or should he save the amount of $6000? As always, we'll still save some time for Doug's (completely epic) trivia. Thanks to the Murder Book Podcast for supporting StackingBenjamins. Check out Michael Connelly's new Murder Book podcast wherever you get your podcasts, or at MurderBookPodcast.com. Go to Airbnb.com/sb and start hosting you’ll receive a $100 Amazon Gift Card if you generate $500 in booking value by May 30. Terms and conditions apply. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Whether you've never purchased a home before or just don't know much about the process, we've got a treat for you today. We're going to dive into everything mortgages 101 today, like PMI, the negotiability of fees, and the lie that everyone quoting rates is telling (those rates "might not be what you think they'd be.") On today's show we welcome the guy who's teaching us everything millennials need to know about mortgages, Jeff VanNote. During our headlines segment, we'll start with one piece detailing how Americans would spend a life-changing sum of money. Do you know how you would spend yours? In our second headline, we talk to head of retirement research from Carson Wealth, professor Jamie Hopkins. Could you be on the hook for your parents' long term care? Plus, in a special third headline, one Florida man received a $980,000 tax refund. Before you start asking how you can cash in as he did, you'll want to find out the rest of that story. Later on, we'll field a Haven Life Line call from Michael, who has $5,000 in savings. He's put in about $500 into Acorns so far to start investing, but should he be doing more? And in our letter segment, Allen tells us how he's been socking away $100 per month since his daughter has been born. She's going off to college in a couple of years, and Allen wants to keep socking away $100 for her in a Roth IRA once she graduates. Where's the best place to start the account? As always, we'll still save some time for Doug's (completely epic) trivia. Thanks to MagnifyMoney.com for sponsoring Stacking Benjamins. MagnifyMoney.com saves users on average $450 when they compare, ditch, switch and save on credit cards, student loan refinancing, checking, savings and more. Check out MagnifyMoney.com for your savings. 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

What should be the number one priority on your retirement planning list? That answer is going to be different for everyone, and on this roundtable episode our contributors gave their take on one list's "most' urgent items. You can find the original show notes from 2016 below: What are the most important moves to make in retirement? Harlan Landes (Adulting.tv, Plutus Foundation) joins Paula (AffordAnything) and Len (LenPenzodotcom) to tackle a recent Wisebread piece that claims to give us the MOST urgent items on your retirement planning list. Does our panel agree? You'll find out on today's show. Also, we mull over real estate home improvements (where do you get the most bang for your hard-earned dollar?) AND dream about what we'd do if we could get unlimited points/miles. Heck, even ChiChi's gets a mention on today's show. You know it's going to be a wild one when we're talking ChiChi's. In our FinTech segment we talk to Jamie Wise from Buzz Indexes(BUZ) about their index and ETF. Hedge fund managers have been following the wisdom of social media crowds...now Jamie and his firm are bringing the same technology to the average investor. Thanks to MagnifyMoneyand SoFi for sponsoring our podcast! Learn more about your ad choices. Visit podcastchoices.com/adchoices

When's the last time you gave you financial life a good inspection? It's been a bit since we talked about having a good look at our financial processes and routines, so the Fintern decided to spin up Joe's interview with Today Show Money Editor Jean Chatzky. Back in 2017 Joe talked to Jean about why people should get a financial "check up." We still think that's a great idea in 2019. Here are the original show notes from 2017: If anyone knows the heartbeat of personal finance, it's Today Show Money Editor Jean Chatzky. On today's podcast, Jean joins us in the basement to talk about your financial engine. How well is it running? She's teamed up with Dr. Michael Roizen to talk about how to age-proof your life. We'll have LOTS of tips and resources today. In our headline segment, we talk annuities. Our arch-enemy Meg forwarded us a nefarious piece about annuities that clearly displays what some annuity salespeople are thinking--they just want your cash. Plus, we throw out the Haven Life line and also save time for Doug's trivia. Special thanks to SoFi and Magnify Money for sponsoring our show! We couldn't do any of this without the support of these awesome companies. Learn more about your ad choices. Visit podcastchoices.com/adchoices

We haven't talked about market timing at all on the show lately, so the Fintern thought it was about time to reach back in the archives and find an old episode on the topic. This eshow is from a Wednesday back before we changed our format. OG sounds like he's in a tin can, to a degree, but if you can get through that, the show itself is a really great collection of letters from you. Here's the original show notes from 2015: Today the star of the show is YOU! You ask us about market timing, diversification and risk…and we deliver the goods. Plus PK is back in the basement to argue with Joe about emergency funds. When is it the right time to save into your emergency fund? Is it best to save BEFORE you pay down debt or AFTER? PK says AFTER and Joe says BEFORE….you’ll hear the epic debate on today’s show! As if that weren’t enough, today’s headline is about China’s recent move to regulate their stock market volatility. Is that good or bad for investors? We also review the film Focus with Will Smith and Margo Robbie. Learn more about your ad choices. Visit podcastchoices.com/adchoices

It's easy to find financial advice on the internet. But finding GOOD financial advice? You'll find that's a bit more difficult. With so many money "gurus" pushing their sage wisdom, how do you sort through all the noise and find the truth? We'll discuss where the "truth" lies today, with some help from our contributors: Chelsea Brannon from Smart Money Mamas, Len Penzo from LenPenzo.com, and OG from this podcast. Today we're tackling money, (bad) advice, and lies! Halfway through the show we'll take a break to talk to Eric Redline, creator of kid-focused money management app, NuMoola. Next we'll answer a Magnify Money call from Scott, who wants to buy a home sooner rather than later. The catch? He doesn't have 20% to put down as a downpayment. Should he charge forward anyway? And don't you worry, we'll save some time for Doug's trivia. Thanks to Grammarly for supporting Stacking Benjamins. For 20% off a Grammarly premium account, go to Grammarly.com/sb. Thanks Audible! Get Power Moves by Adam Grant for free when you sign up for a free Audible trial at Audible.com/sbpower or text sbpower to 500 500. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today we'll throw out our regular playbook to focus on what's really important: your burning financial questions! From Ginny, who wants to become interested in finance (plus a husband who has a BIG man-crush on OG), to Craig and his wife who just inherited a big sum of money....and to Chris wants to know if he should use his savings to pay off his car note before his wedding, we made you and your questions our BIGGEST focus today. BUT, that's not all... we still managed to tackle two big headlines. Making ripples across the financial sector, one ex financial adviser has been sent to prison for seven years after stealing $300,000 from a 97 year old. How do you avoid that mess? We'll show you where this situation went off the rails. Plus, in our second headline, a series of mistakes has the Omaha Public School' pension fund scrambling after a $771 million shortfall. Headlines like these don't exactly inspire trust in the financial industry, so we'll share our big ideas on saving for retirement without walking into a mess like this. A letters episode doesn't mean we're skipping out on the Haven Life Line! Jared is at a critical point with his financial advisor, who hasn't had the best returns in the past couple of years. Is it time for Jared to give his advisor the boot? We can't make the decision for him... but we can tell him our thoughts. As always, we'll still save some time for Doug's (completely epic) trivia. Thanks to LinkedIn for supporting Stacking Benjamins. Go to LinkedIn.com/sb and get a $50 credit toward your first job post. Thanks to Grammarly for supporting Stacking Benjamins. For 20% off a Grammarly premium account, go to Grammarly.com/sb. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Nearly everyone has had a "great" business idea. However, as mom says, "the devil is in the details," and great businesses aren't built on ideas, they're built on successful implementation and follow through. To help you set up either your next side gig or start your next big venture, we're excited to talk to Maria Aspan, Editor at Large for Inc. Magazine. She'll discuss where to look for financing, the importance of a business plan (is it really important?), how to ask family for money, when to include venture capitalists, and more. She'll also share some fantastic success stories from people who've already accomplished what many of our listeners want to learn. Plus in our headlines segment millennial money expert Stephanie O'Connell stops by the basement to discuss the new layaway alternative, Afterpay. Here's how it works: pick out what you want today and pay for it later. Does that sound somewhat like a credit card? Stephanie breaks it all down during our interview. And in our second headline, Cardi B is speaking out against people who are taking jabs at her spending habits. She says she's spending over $300,000 per month and can't lower her bills any more. What's her reasoning? We'll jump into her personal financial issues and talk about responsibilities during our second headline. And in our Haven Life Line, Dustin has his investments for his son's college in the market. With college quickly approaching, where should Dustin be moving his money? Then we'll take a letter from Chris, who wants more information on the rule of thumb many of us have heard, of having a certain threshold of money saved by different ages. As always, we'll still save some time for Doug's (completely epic) trivia. Thanks to MagnifyMoney.com for sponsoring Stacking Benjamins. MagnifyMoney.com saves users on average $450 when they compare, ditch, switch and save on credit cards, student loan refinancing, checking, savings and more. Check out MagnifyMoney.com for your savings. 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

Whether it's big check time from the IRS or not, it's always important to know ahead of time what to do with a large sum of money. Do you have a plan for your tax refund cash? Today, whether you have the beginnings of a plan or no clue, this show is for you. Today we're joined by host of the Seven Figures podcast, Sandy Waters, Paula Pant from Afford Anything, and our very own OG. About halfway through the show we'll take a break and talk to Mark Elliot from TIAA about your career. Looking for a more meaningful vocation? Mark will describe CareerPurpose.com, a partnership they've formed with LinkedIn to help people like you improve their work life. And after some deep-sea inspired trivia from Doug, we'll cross the finish line by taking out the magnifying glass and helping listener Austin. He could finish paying off his loans this year, but that would mean taking a year off from investing. What should he do? Thanks to OnDeck for sponsoring the show. For a free consultation with one of their US-based loan specialists, go to OnDeck.com/SB. Thanks to Grammarly for supporting Stacking Benjamins. For 20% off a Grammarly premium account, go to Grammarly.com/sb. Learn more about your ad choices. Visit podcastchoices.com/adchoices

We're celebrating Valentine's Day in true money podcast fashion, talking all things romantic, like wine, spreadsheets, money dates, and open communication about money. We know...total romance. Joining us to discuss all of these things and more are a father-daughter financial planning team of Walter Wisniewski and Allison Vanaski. We'll also talk about non-verbal money cues (what is your significant other NOT telling you about money, but is showing you?), why we're afraid of money chats, and how to discuss financial topics with aging parents and non-family members. We're talking all things communication on today's show! Plus, in our headlines segment, do credit scores factor in to how we look at love? Does good and bad credit matter in the dating world? We'll talk statistics and love with Jonathan Walker from The Center For The New Middle Class. Plus, Joe and OG will discuss one piece that covers 5 mistakes you could be making with your money. Later on, we throw out the Haven Life Line to Zac and his wife. They've recently discovered the FIRE movement and now want to retire by 50. With conventional logic suggesting to invest into accounts that won't be available under after 50, where should Zac and his wife be looking to invest with Fire in mind? Plus, we're also answering a letter from Any Mouse, who wants to know if he has enough assets to cover his son in the event that something happened to him. And don't worry... we'll still take some time for Doug's trivia. Thanks to the Murder Book Podcast for supporting StackingBenjamins. Check out Michael Connelly's new Murder Book podcast wherever you get your podcasts, or at MurderBookPodcast.com. Thanks to Grammarly for supporting Stacking Benjamins. For 20% off a Grammarly premium account, go to Grammarly.com/sb. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Tanja Hester realized at a young age that even though she loved her career, she was still helping an organization chase THEIR goals instead of her own, and that's when her plan to make work optional was hatched. On today's show she'll talk about not only her story, but also about how she and her husband tracked their progress (dual spreadsheets!), discussed the timing of leaving, and downsizing her lifestyle. She also shares potential struggles she sees down the line, like rising health care costs. Whether you wish to retire early, or just retire someday, this is an interview for you. Plus, attorney Leslie Tayne will help us answer the Haven Life line call for help from Vince, who is worried that his mother is going to be on the hook for some loans she's co-signed. How does she remove herself if the main signer is nowhere to be found? In our headlines segment, we'll discuss 401(k) jargon. What terms do you must struggle with? We'll also share some advice for the upcoming Valentine's day holiday. And don't worry... we'll still have time for Doug's trivia. Thanks to MagnifyMoney.com for sponsoring Stacking Benjamins. MagnifyMoney.com saves users on average $450 when they compare, ditch, switch and save on credit cards, student loan refinancing, checking, savings and more. Check out MagnifyMoney.com for your savings. Thanks to OnDeck for sponsoring the show. For a free consultation with one of their US-based loan specialists, go to OnDeck.com/SB. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever ask yourself why you never seem to have enough money? Maybe the answer is that you need to make more at work, or maybe you just eat out a little bit too much during the week? On today's roundtable, we're joined by Marcus Garrett of the Paychecks and Balances podcast, Len Penzo (from LenPenzo.com) and our very own OG. We're tackling 7 questions that, if you're honest with yourself, will give you the answers to why you never seem to have enough money. Halfway through the roundtable, we'll take a break for the FinTech segment. Joe talks to Ksenia Yudina, founder of college savings platform U-Nest. Ksenia is a mom of three and wanted an easier way to save for college... so she went out and created one. We're also fielding a MagnifyMoney.com question from Matthew and his fiancée. They're thinking about getting into real estate but aren't big on the idea of getting back into debt. Should they keep their focus on investing in the market, or take the plunge? And of course, we'll still have time for Doug's trivia. Thanks to the Murder Book Podcast for supporting StackingBenjamins. Check out Michael Connelly's new Murder Book podcast wherever you get your podcasts, or at MurderBookPodcast.com. Thanks to Away for supporting Stacking Benjamins. Go to AwayTravel.com/sb and use the promo code sb to get $20 off a suitcase! Learn more about your ad choices. Visit podcastchoices.com/adchoices

If you're hoping for financial freedom, Grant Sabatier is maybe the perfect man to hear speak. At one point he was down to less than ten dollars in his accounts, and within a short time went from broke to a millionaire. How did he do it? He'll share his story (which includes how he made money), but also share how to drastically cut your expenses so that you can build your own fortune. In our headline segment, we'll talk to JJ Kinahan about financial independence. TD Ameritrade recently commissioned a study about the Financial Independence Retire Early movement. It turns out that many people chasing financial freedom have different ideas about "FIRE" than you may have heard in the past. We're also throwing out the Haven Life Line to Kody, who doesn't fully trust in the public service loan forgiveness program. He's going to be investing money into a taxable account so he'll be able to pay off the loan if needed. What do we think of him investing the amount instead of sticking it into a savings account? Plus, we'll be throwing out a letter to And don't worry... we'll still take some time for Doug's trivia. Thanks to Omax Health for supporting Stacking Benjamins. Visit Tryomax.com/sb for your free box of Omax3 Ultra-Pure with your first purchase. Thanks Audible! Get Power Moves by Adam Grant for free when you sign up for a free Audible trial at Audible.com/sbpower or text sbpower to 500 500. Learn more about your ad choices. Visit podcastchoices.com/adchoices

THE Jill Schlesinger returns to the basement to talk about three horrible investments people buy: gold, reverse mortgages, and hedge funds. We'll also discuss annuities, permanent life insurance, and other frequent offenders. If you're using any of these products, don't panic! These can all be used successfully in your plan, and Jill will talk about the horrible ways people are tricked into using these products so that you don't make the same mistakes. Then, in our headlines, we'll cover a piece about industry "sheriff" FINRA cracking down on companies offering expensive 529 plans. Companies will have until April to report themselves and avoid potentially big fines. We'll break down the big picture and what it means to you before we field a call from Trim CEO Thomas Smyth. Mastercard is unrolling a new plan to add consumer protections against those tricky "free" trials that we've all fallen pray to at one point or another. We'll dive in with Thomas to figure out what's all going on with the world of subscriptions and hidden fees. We're also throwing out the Haven Life Line to Xandra, who's fully invested in the total stock market index fund. With her 401k, HSA, and IRA taken care of, should she be branching out into emerging markets and small cap growth funds to diversify? We'll field a letter from Huy, who's being doing well with their 401k, but wants to open a Roth IRA. So... what exactly is an IRA? How do you open one? We'll break it down for Huy during out letters segment. And don't worry... we'll still have time for Doug's trivia. Thanks to Omax Health for supporting Stacking Benjamins. Visit Tryomax.com/sb for your free box of Omax3 Ultra-Pure with your first purchase. Thanks to Away for supporting Stacking Benjamins. Go to AwayTravel.com/sb and use the promo code sb to get $20 off a suitcase! Learn more about your ad choices. Visit podcastchoices.com/adchoices

This is the weekend we'll nearly all see (whether we're a fan of sports or not) people at the "top of their game" showing off their ability to excel at their craft. Here's our question: how do you excel with your money? That's why today we're discussing how YOU can maximize you financial Big Game with some good thought-out planning. Plus, we're not bringing you just one special guest today... but TWO. Joining us is Jace Mattinson and Clark Sheffield from the Millionaires Unveiled podcast. And we're keeping the party going with two contributors you know and love: Paula Pant from AffordAnything.com, and Len Penzo from LenPenzo.com. Halfway through the roundtable, we'll take a little break for our Friday Fintech segment. Joe's having a discussion with Justin Bailey, co-founder of saving and investing platform VimVest. Have plenty of savings goals but not exactly sure how to prioritize? You'll want to listen in to this interview. We'll also answer a MagnifyMoney.com question from Rob, who is a high school teacher. What's some great financial knowledge Rob should be gifting to his students before they graduate? And of course, we'll still have time for Doug's trivia. Thanks to the Murder Book Podcast for supporting StackingBenjamins. Check out Michael Connelly's new Murder Book podcast wherever you get your podcasts, or at MurderBookPodcast.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Are you horrible with money? Turns out you're not alone (big surprise)! While most of us have been bad with money at some point in our lives, we don't usually write a book about it. Today we're joined by Gaby Dunn, who today will dive into her early years, and the money scripts she learned from school, parents, and friends. It's a quick look into her new book :Bad With Money. Plus, during our headlines segment, a Barron's piece proves again just how many people don't understand the FIREmovement. And in our second headline, investors are looking for "safer" investments as the economy continues to fluctuate. It's a sad reality that no matter how much we talk about not sabotaging your financial plan, people seem to consistently find a way to shoot themselves in the foot with their financial behavior. Later in the show, we'll throw out the Haven Life Line to Kathy, who is looking to retire in the next decade. She should be shifting more of her portfolio over to bonds? What's the right balance between bonds and equities as one gets closer to retirement? We'll also take time to answer a letter from Braden, who's fresh out of college and has his first full-time job. What are some resources he can use to start investing? And don't worry... we'll still have time for Doug's trivia. Thanks to Grammarly for supporting Stacking Benjamins. For 20% off a Grammarly premium account, go to Grammarly.com/sb. 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

On today's show we're taking your letters, but first, we're talking to Hannah Rounds, our favorite tax software reviewer, who gives us the lowdown on the good, bad and ugly of tax software. She'll tell us which brands to avoid, which are her favorites, and which packages are surprising. Whether you're willing to pay for your tax support or are looking for the best software package for free, we'll dive into all of the brands to help make your filing season easier. We're happy that the government shutdown is over for now, but what if it happens again in three weeks? We'll talk to Lacey Langford from the Mil Money Movement podcast about the fallout from the shutdown. If people are trying to duct tape together their financial picture until the receive their first paycheck after the shutdown, what do they do? We'll discuss resources, advice, what NOT to do, and more. Later on, we'll throw out the Haven Life Line to Pete, who wants to know if he should invest some of his extra cash into a short-term bond fund. He has a large cash reserve, and with interest rates being very low on savings accounts, he wonders whether it'd be worth the time to spike up the interest rate possibilities a little. And don't worry... we'll still take some time for Doug's trivia. Thanks to the Murder Book Podcast for supporting StackingBenjamins. Check out Michael Connelly's new Murder Book podcast wherever you get your podcasts, or at MurderBookPodcast.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

What does it really mean to be poor? We're not talking about poverty...that's a whole different issue, when compared to one article we're discussing today, which covers the difference between people who are "poor" but own lots of stuff and people who are "rich" and own very little. What do we mean? We'll dive in to this topic today with our roundtable group of bloggers and podcasters, including Cody Berman, co-host of the FI Show; Len Penzo of LenPenzo.com; and from our own Stacking Benjamins podcast, OG. Plus, we'll take a call from Tyler, who has some stock market questions about 2019. Can the Magic 8 Ball possibly help him with his issue? And, if that isn't enough, we'll also answer a question from the mailbag! Halfway through the show we'll take a break and talk tax prep with Katherine Pomerantz of The Bookkeeping Artist. Katherine brings some great information on how to get your books organized for this year's tax season, and some advice that'll hopefully keep a bit of your hair on your head through April's filing season. ...and of course, we'll still have time for Doug's trivia. Thanks to OnDeck for sponsoring the show. For a free consultation with one of their US-based loan specialists, go to OnDeck.com/SB. Thanks to Skillshare for sponsoring the show. Start your two months of unlimited access to Skillshare by visiting SkillShare.com/SB. Learn more about your ad choices. Visit podcastchoices.com/adchoices

With all of the news dominated lately by the government shutdown and Washington politics, it's easy to focus on things outside of your control. But if you're going to become a millionaire, it's time today to refocus your energy on YOU and what you need to do personally to find your way toward financial success. The perfect person to talk to about personal responsibility comes down to the basement today, Chris Hogan. We'll dispel some of the myths around who's a millionaire and help you set up your plan of attack to join the ranks yourself....sooner rather than later. In today's headlines: will the government shutdown impact this year's tax return season? Even with a partial recall of IRS employees, there's still plenty of potential issues if the agency doesn't return to full strength. We'll discuss one piece today that takes a look at all the possible problems for individuals and businesses alike. Plus, we'll be throwing out the Haven Life Line to Matt, who is recently married. What are some resources available for newlyweds going through their first tax season? After that we'll take some time to answer a letter from Jon, who wonders if his wife should ditch her whole life policy for term life insurance, and invest the difference in a Roth. And don't worry... we'll still have time for Doug's trivia. Thanks to Skillshare for sponsoring the show. Start your two months of unlimited access to Skillshare by visiting SkillShare.com/SB. Thanks to OnDeck for sponsoring the show. For a free consultation with one of their US-based loan specialists, go to OnDeck.com/SB. Learn more about your ad choices. Visit podcastchoices.com/adchoices

We're dedicating this episode to a very special guest: YOU. Our mailbag is overflowing, so today we realized it was time to devote a whole episode to answering your burning questions. Scott has cash left over after he pays bills and maxes out his regularly scheduled savings contributions... should he open up a Roth IRA? How should Laura prioritize her savings goals: pay down debt, add to retirement accounts, or build her emergency funds? Tyler has been recruited by his local Edward Jones agent. Should he begin his career with them? In our headlines segment, one recent piece asks the question, "Is your debt the driving factor behind your savings discussions?" We'll tackle why that's an issue, and how it can harm your long term plans. In our second headline we'll look at some changes coming this year to health savings accounts (HSAs). Later on, we'll throw out the Haven Life Line to John, who wants to know how to invest his lump sum. Should he dollar cost average over the next year or dump his stash of money into his account at one time? And don't worry... we'll still take some time for Doug's trivia. Thanks to MagnifyMoney.com for sponsoring Stacking Benjamins. MagnifyMoney.com saves users on average $450 when they compare, ditch, switch and save on credit cards, student loan refinancing, checking, savings and more. Check out MagnifyMoney.com for your savings. Thanks to Grammarly for supporting Stacking Benjamins. For 20% off a Grammarly premium account, go to Grammarly.com/sb. Learn more about your ad choices. Visit podcastchoices.com/adchoices

How do you put the brakes on spending so much money? ....... Our special guest today is Ashley Feinstein Gerstley, author of The Thirty Day Money Cleanse, and she's an expert in cleaning up your budget. We'll talk with her and our team about a recent Budgets Are Sexy blog post in which blogger J. Money lays out how he avoids spending money. What games do you play with yourself to distract yourself from spending money. Plus, two contributors you know and love, Len Penzo from the LenPenzo.com blog, and from Afford Anything, Paula Pant. Halfway through the roundtable we'll take a break for our Friday Fintech segment and talk to DeAnn O'Donovan from AHP Servicing. AHP Servicing is a company that's setting out to help people who are struggling with their mortgages find ways to stay in their homes. We'll also answer a MagnifyMoney.com question from Paul, who has the opportunity to buy shares of a new company. He's sure the price is going to jump up. Should he use he cash he has on hand to buy shares, or take out a loan to get even more shares? And of course, we'll still have time for Doug's trivia. Thanks to Masterworks for supporting Stacking Benjamins. Visit Masterworks.io and reserve your shares now. See disclaimer at Masterworks.io/disclaimer. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Could you go a few days without spending any money? A few weeks? How about a few months? Starving your wallet might be simpler than you've previously thought. Jen Smith, co-host of the Frugal Friends podcast, joins us today to talk about gifting yourself a "No Spend Challenge." How does it work? We'll cover her story of spending little to no money to cure her debt issues, and then how she refined the concept to create a plan worthy of talking about on our show and elsewhere! And in our headlines segment of the podcast, some great news! Long term care benefits have been added to the new crop of Medicare Advantage plans. We'll invite Danielle Kunkle Roberts from Boomer Benefits over so we can all learn more. Plus, we'll take a look at recent changes in the annuity industry. Annuity providers are making a combined effort to bring the industry into the 21st century to speed up the exchange process from months to a week. What does that mean for you? We'll dive in more during our headlines segment. Later on, we'll throw out the Haven Life Line to Sean, who's a minority stakeholder in a corporation. The majority stakeholder wants to buy him out... what questions should Sean be asking? And don't worry... we'll still have time for Doug's trivia. Thanks to Omax Health for supporting Stacking Benjamins. Visit TryOmax.com/sb for your free box of Omax3 Ultra-Pure with your first purchase. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wonder how someone decides to aggressively attack a goal, like paying down your mortgage? Talaat McNeely and his spouse Tai decided to think HUGE thoughts when they set out to pay off their house in five years. They didn't know how they'd do it, but they set out anyway and took action, and ultimately accomplished their goal. Today Talaat will tell their family's fantastic story from start to finish. He'll share what they did well and also how they could have maybe paid the house off even faster. He'll share their feelings and emotions along the way that sometimes came near sabotaging their goal...and at other times that helped spur them on to victory. Plus, in our headlines segment, we'll detail a great list of questions you should ask a financial advisor. Do you have questions ready when you go in to see an advisor? We'll share some of our favorites before jumping over to our second headline: one California man learns ten million reasons why you shouldn't tell your roommates about hitting the jackpot... see where this is going? Yeah, it's a cautionary tale. Later on we'll throw out the Haven Life Line to Colin, who wants to know our thoughts on target date funds. He's been dollar-cost averaging into a Vanguard target date retirement fund for the past 10 years. Should Colin change his investment strategy? What are out thoughts? We'll also get through TWO letters today. First, Shaun is a financial advisor and wants to know what type of data he should be presenting his clients. Next, will take on a letter from Christy, who writes in to address our answer to a letter asking about individual life insurance. And don't worry... we'll still take some time for Doug's trivia. Thanks to Masterworks for supporting Stacking Benjamins. Visit Masterworks.io and reserve your shares now. See disclaimer at Masterworks.io/disclaimer. Thanks to Omax Health for supporting Stacking Benjamins. Visit Tryomax.com/sb for you free box of Omax3 Ultra-Pure. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Did you spend too during the holiday season? Studies showed that many of us WAY overspent this year, to the tune of over $1,200 more spending than we could truly afford. Add that to the huge amount of debt people are already carrying, and this year's problem can easily become next year's problem. To help you wash away your debt problems, today we're talking to Nick Clements on the psychology behind debt management, and the many different ways you can get your year started on the right foot in our annual holiday debt cleanse episode. Plus, if you're looking to make some extra money on the side to pay down your holiday bills, we've got you covered. We're calling our old friend Harry Campbell, founder of The Rideshare Guy blog and podcast. He'll share lots of ways to help you quickly raise hundreds (and maybe thousands) of dollars. Later on we'll throw out the Haven Life Line to Bryan, who took out a 401k loan to buy a rental property. Bryan has extra cash coming in and could pay off the loan pretty quickly. Should he do it? What would be the downsides of choosing to make minimum payments? And don't worry... we'll still have time for Doug's trivia. Thanks to Skillshare for sponsoring the show. Start your two months of unlimited access to Skillshare by visiting SkillShare.com/SB. Thanks to Slack for supporting Stacking Benjamins. Slack: Where work happens. Go to slack.com to learn more. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In this tumultuous market, how certain are you about your investment strategy? Larry Swedroe joins us today to talk retirement planning, but especially to talk about weathering the storm of risk and uncertainty in this market. We'll talk about what's normal for the market, why so many people fail, how an all-stock portfolio might or might not work for you, and more. Plus, in our headlines segment, lots of people moved their money to treasures to start 2019. Could this foreshadow upcoming negative market conditions this year? We'll share our feelings on today's podcast. Plus, one major publication piece shares how much money you should have in stocks at every age. Is this good advice, or could it be guiding people down the wrong path? We'll talk about appropriate investment advice for people who are far from retirement, middle aged, and nearing or in their retirement years. Later on we'll throw out the Haven Life Line to Joseph and his wife. They're looking to get a home loan but don't really like their options. Could raising their credit score open up better choices for them? We're also answering a letter from Matt, who wants to know more about his 401k options: Roth, traditional, and after-tax. He's also using part of his 401k at a quasi-emergency fund. Is he setting himself up for failure? And don't worry... we'll still take some time for Doug's trivia. Thanks to MagnifyMoney.com for sponsoring Stacking Benjamins. MagnifyMoney.com saves users on average $450 when they compare, ditch, switch and save on credit cards, student loan refinancing, checking, savings and more. Check out MagnifyMoney.com for your savings. Thanks to Slack for supporting Stacking Benjamins. Slack: Where work happens. Go to slack.com to learn more. Learn more about your ad choices. Visit podcastchoices.com/adchoices