The Stacking Benjamins Show

Wondering how the best and brightest leaders emerge in any organization? Whether you're running a business or just your household, we all need leadership skills, and today's guest focuses on those of the great leader, Walt Disney. We'll sit down with Pat Williams, motivational speaker, author, and co-founder of the NBA Orlando Magic franchise. Pat combines his decades of management experience with the leadership lessons from the visionary animator to provide you with relevant and practical lessons on how to lead in the modern workplace. Our talk with Pat begins at the 30:49 mark. Plus, during our headlines segment, we'll take a call from Leo Acheson, associate director of multi-asset and alternative strategies team at Morningstar, about the company's newest report on the state of health savings accounts. HSAs have changed a lot since we last spoke with Leo a year ago, and we'll ask him about improvements in the industry and which plans are the best accounts you should be watching out for. We'll begin our headlines segment at the 5:15 mark. Later we'll throw out the Haven Life Line to Julie, who's found herself with a few hundred dollars that she wasn't expecting. What's the best way Julie could invest this small, one-off windfall? Of course, we'll save some time for Doug's trivia. Thanks to Kabbage for supporting Stacking Benjamins. Get the money you need to run your small business. Go to Kabbage.com to get started. Credit lines subject to review and change. Individual requests for capital are separate installment loans issued by Celtic Bank, Member FDIC. Thanks to HoneyBook for supporting Stacking Benjamins. If you run your own business, you’re used to doing it all. But if you’re struggling to get through your to-do list, HoneyBook can help. Go to HoneyBook.com/SB for 50% off your first year. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What do you get when you place a bunch of seasoned workers in a room? You immediately start telling stories about the best career advice anyone has ever given you. Today we do just that, with the host of the Beyond The Dollar podcast: Sarah Li-Cain. We’ll work from a post detailing how a Netflix co-founder's father left him a handwritten list of 8 rules to success. What are those rules? Check out what Sarah, Len Penzo, and Paula Pant all have to say about them! Halfway through the show, we’ll take a break to talk about higher interest rates. Who’s working on that? Well, one company is, and today we’ll give you an introduction to Froogal, with CEO Kale Pasch. Plus, we'll answer a voicemail during our Magnify Money segment asking for resources on podcasts and blogs for families AND we'll have some fun with another of Doug's wild trivia questions. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Why are college costs increasing so fast? While there are lots of theories, only one researcher has reached out to many middle-class families to directly ask them how much money they've spent on college and to get the direct story. Today we talk to her. Caitlin Zaloom joins us on today's podcast to dig in to the problem with college funding. 529 plans? Saving directly with the state using pre-paid tuition? We'll tackle LOTS of scenarios and throw out some ways to solve the problem on today's show. In our headlines segment, we talk about borrowing money from your 401k plan. Even though you can borrow from it without penalty, just because you can, doesn't mean you should. We'll also dig into the chaos that's been created as some of the biggest brokerage firms in the country swipe fees all the way to ZERO. Is that a good thing? After a little dose of Doug's trivia, we'll wind up the show by throwing out the Haven Life Line to an anonymous caller who calls out Joe and OG....well, maybe not OG. More directly....just Joe. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What would you say to someone who said they could teach you to be rich? Would you have a hard time believing them? Today we'll sit down with the person who has already done just that for thousands of people across the country: New York Times best-selling author Ramit Sethi. In our headlines segment, what's the deal with gold? We'll take a look at one article from InvestmentNews that makes the case against gold. But, do we think it has a place in your portfolio? Is that money better deployed elsewhere? We'll give our nuggets of wisdom thoughts before moving into our second piece: 5 things plan sponsors are still getting wrong. You've ran into at least one of this issues (or know someone who has). We'll also throw out the Haven Life Line to Mandy, who wants some advice on what to do with her money in the market. Should she stay invested, or cash out and buy a house? Of course, we'll save some time to spend on Doug's surprisingly money-themed trivia. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is it frustrated watching successful people work? They seem to do it so easily....and sometimes they even tell you that it IS easy. But is that the truth? What's really behind the success of many people who wisely handle money, or make better business decisions, or seem to juggle priorities easily? There IS a secret...and once you know it you think about the working world differently. Today our special guest Steven Donovan from EvenStevenMoney.com joins OG and Joe to tackle what's really behind success for the average person. Halfway through the show, our roundtable discussion will take a break for our Fintech segment. We'll talk to Erin Papworth from Nav.IT, an app and community helping people not only track their expenses and their goals, but helping to keep them accountable AND connecting them with a community of like-minded individuals. How does it work? We'll talk to Erin all about it! Plus, we'll answer a voicemail during our Magnify Money segment AND save time for Doug's amazing trivia. Thanks to Masterworks for sponsoring our show! Visit masterworks.io Select podcast, then enter Stacking Benjamins to skip the waitlist. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wonder what it would be like to buy a van and hit the road? Van life is an exciting reality for many people you read about online...but would it be for you? Today we talk to Lisa and Harrison from the Mad Money Monster Podcast, who together decided to try it out. The results? Let's just say it may not have gone exactly the way many bloggers act like it will. In our headlines segment, we're all about cults! One recent financial piece compares Multi-Level Marketing companies (MLMs) to a cult, but are they really similar? We'll share a story from a former Mary Kay consultant who was tricked into an MLM even though she didn't have any money. Lots of promises, but no results. Is it the way things are for MLMs in general? We also prepare you for the next recession! After a little dose of Doug's trivia, we'll throw out the Haven Life Line to Janelle who is looking to switch jobs. Janelle opted out of receiving benefits from her employer and wants to know if she can use that to negotiate getting a higher salary? Learn more about your ad choices. Visit podcastchoices.com/adchoices

Hoping to retire someday? What about retiring early? On today's show we'll sit down with Chris Mamula who retired at...wait for it....41, about how he did it. He's the co-author of the newly released book, Choose FI: Your Blueprint to Financial Independence, and also is an award-winning blogger at CanIRetireYet.com. He and his wife blazed their own trail toward freedom after meeting with advisors who didn't serve them and reading blogs that didn't speak to them. They might have also listened to a podcast or two that didn't meet with their expectations. Before all that, though, in our headlines segment, we'll cover one piece from Financial Planning about a Vanguard robo-advisor only recommending... (wait for it) ... Vanguard funds! Think something seems a little fishy with this? We'll throw our two cents into the ring, and still save plenty of time for our second piece from Forbes: women just aren't purchasing enough life insurance. This is SUPER disturbing, given how much women contribute to the average family. If they have a 50% contribution, why aren't they asking for more insurance? We'll share the ugly details. Plus, we'll still have time to throw out the Haven Life Line to Stevan, who thinks it's the right time to start a retirement account. Based on his current tax bracket and the research he's done, Stevan feels like he should choose a Roth IRA over a traditional to get started... is he missing anything? What would be the pros to choosing a traditional account? Of course, we'll always have time for Doug's trivia. Thanks to Grammarly for supporting Stacking Benjamins. Get 20% off a Grammarly premium account, go to Grammarly.com/sb. Get the money you need to run your small business. Go to Kabbage.com to get started. Credit lines subject to review and change. Individual requests for capital are separate installment loans issued by Celtic Bank, Member FDIC. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Does it makes sense to hire a coach? Our roundtable discussion today is all around the pros and cons of finding a coach--why do you need one in the first place? How do you find a good one? How do you know it's a good fit? We'll cover all of these and more on today's show with two coaches and a guy who doesn't have one....Sharita Humphrey joins us from Family, Faith and Finance, along with Roger Whitney, the Retirement Answer Man, and Len Penzo from Len Penzo dot com. Halfway through the show, we'll celebrate national tourism day with Kat Kalashian from Live and Invest Overseas, who'll share her list of the top six countries around the world to target if you'd like to live a "work from anywhere" lifestyle. Plus, we'll answer a voicemail during our Magnify Money segment asking for resources on podcasts and blogs for families AND we'll have some fun with another of Doug's wild trivia questions. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Have you ever wondered if you're handling your money right? Sure you have. More important, have you ever worried that you aren't doing LIFE correctly? Our main guest has been there. She's the best-selling author of the philosophical guide to life in the age of overwhelm titled, Am I Doing This Right?, Colleen Bordeaux. Colleen will share her deeply personal search for more meaning in life and lessons she learned along that way. We'll talk about your personal philosophy, getting comfortable with who you are, figuring out your money from a deep level, and more. It's a wide-ranging interview that we're sure you're going to enjoy as much as we enjoyed talking to her. In our headlines segment, how much does it cost to be considered 'middle class' in a big city? It turns out that it might just cost a TON of money. How do you get ahead when everything is so expensive? We'll talk about many factors, include the fact that where you live can change everything about whether you're financially successful or not. In our second headline, do you prefer receiving money advice from a man or a woman? Well, according to the Wall Street Journal, in the past two years there has been a marked increase in requests from prospective clients who want to work with female financial advisers. We'll talk diversity in the financial services ranks on today's show! After a little dose of Doug's trivia, we'll also save time to throw out the Haven Life Line to Nick. Nick asks if there is a specific ratio of money in each account (Roth and pre-tax) that is recommended? How does your tax strategy look? We'll dive into that, and much more. Learn more about your ad choices. Visit podcastchoices.com/adchoices

How does a guy with a great job at Facebook end up as a standup comedian? Today we talk to Paul Ollinger, host of the new Crazy Money podcast, about chasing your dream...in his case, the dream of becoming a comedian. It's a compelling conversation if you've ever hit the wall with your career, or you've ever made a spur-of-the-moment decision, or you realized that you needed to sharpen the saw to get where you wanted to go. There's something for everyone in today's interview. During our headlines segment, one recent piece takes to task the age-old idea of dollar-cost averaging. Should you do it? You'll be surprised with the results. Plus, do you think becoming a millionaire is out of your reach? I think you're going to love the great news we have for you. With some sound investment strategies and saving your cash, you could find yourself among that list too. On the Haven Life line call, we talk to Maddox, who's wondering what he should do better with his money. He's a college student (and actually turning a profit while in school!), and already has a firm base-level investment plan. Should he diversify more? We'll weigh in, and of course, we'll have time for Doug's trivia. Thanks to Clearbanc for supporting our show. Thanks to Clearbanc for supporting our show. Go to clearbanc.com/SB to sign up today to get $1,000 of additional capital if you are approved as a qualifying company. Thanks to HoneyBook for supporting Stacking Benjamins. Go to HoneyBook.com/sb for 50% off your first year. Learn more about your ad choices. Visit podcastchoices.com/adchoices

We spend more and buy stuff to make us happy, but does it? Does more really equal better? On today's show we dive into a recent blog post from the Four Pillar Freedom blog to look at the nature of happiness. Money is always intertwined in our view of "happy," probably because advertisers love making us think that if we just buy one more thing we'll finally get that elusive joy that we've been craving. We'll talk about joy, addiction, happiness and more on today's podcast with a team including Beau Humphreys from The Personal Finance Show, CFP Katie Brewer from Your Richest Life planning, and our own OG. Halfway through the showwe have a special treat where we usually feature our Friday Fintech spotlight. Today instead we'll shine a light on mortgages, because with his recent move to Detroit, Joe just found out that industry insider Joel Gurman from Quicken Loans is his neighbor! Joe invites Joel down to the basement today and quizzes him about the state of mortgages, how interest rates really work, what other fees are involved with mortgages, and more. It's a wide-ranging, fun conversation about the biggest loan many of us will ever have. But that's not all. We'll help C on the Magnify Money call-in segment. C is wondering about retirement withdrawal software. He feels that savings-wise, he is on course, but he wants to make sure that he is withdrawing in the most tax-efficient way. Thanks to AcreTrader for supporting Stacking Benjamins. For more information on how to become a farmland investor through AcreTrader, visit acretrader.com/sb Learn more about your ad choices. Visit podcastchoices.com/adchoices

At some point you feel fried. Been there? Today's guest, Nicole Lapin, has been there. She thought she could outrun her problems and find success...and today we'll hear how that worked out. Nicole is a New York Times best selling author of both Rich Bitch and her second title Boss Bitch. Today she's back with a new guide to help us figure life out. We'll talk about balance, acceptance, and not trying to outrun your problems on today's show. In our headlines segment, how's your will looking? The wills of a couple people in the news lately are UGLY. We'll focus on the wills of Jeffrey Epstein and Aretha Franklin today, and some huge questions that have come up because of weird circumstances in both (very different) cases. Then, we'll pivot to a chat about wine destinations (how fun is that???). Good news: one recent piece says you don't have to go to Venice or Napa, and to get a great vacation you might not even need a passport. There are low budget destinations for whatever fun you have planned in places you wouldn't believe. After a little dose of Doug's trivia, we'll throw out the Haven Life Line to Rina, a concerned mother who asks how she can set up a Roth IRA for her child. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Would you know what to do in the 24 hours after a car accident? What about that next 7 days? The days following an accident is a stressful time, but following the right steps can make a big difference. On today's show we'll talk to Elizabeth Calora, partner at PCVA Law, to talk about what you should do after you are involved in an accident. During our headlines segment, one retiree placed her life savings into an annuity without knowing the full consequences, (on the advice of a financial advisor). After an uphill battle, PNC bank has finally agreed to refund her money...but is that the full story? Of course it isn't. We'll share the not-so-obvious conclusion during our breakdown. PLUS, we bring you a slice of sunshine (because that's what we do best). It turns out that average 401k savings rates have hit record levels. That's neat...but as yours? Becky calls our Haven Life Line today. She's over 60 (we didn't ask....she told us!), and she shares that she's worred that she has close to ZERO cash in after-tax accounts. She has good news, though....she DOES have money in Roth accounts that have sat for over 5 years. So does she need an after-tax account? Is she missing anything? Of course, we'll always have time for Doug's trivia and bunches of fun. Thanks to Skillshare for supporting Stacking Benjamins. Get TWO months of courses for free at Skillshare.com/SB. Get the money you need to run your small business. Go to Kabbage.com to get started. Credit lines subject to review and change. Individual requests for capital are separate installment loans issued by Celtic Bank, Member FDIC. Learn more about your ad choices. Visit podcastchoices.com/adchoices

"Speed kills" is a popular phrase, but in business, you already hear that faster = better. But is it? If you make a mistake with your money, whether it's making it, spending, tracking or investing...how important is speed (or slowing down) in your decisionmaking? We'll take this philosophical discussion and dive in today with Amy Blacklock from Women Who Money, Len Penzo from LenPenzo.com, and our very own OG. It's a lively discussion that ping-pongs between deep philosophy to light tactics, and, of course, a little fun. Halfway through the show, our roundtable discussion will take a break for our Fintech segment. Aditi Shekar takes a trip down to the basement to re-introduce new listeners to Zeta! We've had quite a few people in our Stacking Benjamins Basement Facebook group ask about apps for couples, and Zeta is exactly that. Aditi will talk about what's changed with Zeta in the last couple years, beyond helping couples track their transactions and develop a budget for their money management. Plus, we'll answer a voicemail from D during our Magnify Money segment. D is wondering about the details of a taxable brokerage account. D and his wife save up for a goal, and when they reach that goal, they no longer want that item. D was curious if moving those savings to a brokerage account would be more financially lucrative. Thanks to Grammarly for supporting Stacking Benjamins. Get 20% off a Grammarly premium account, go to Grammarly.com/sb Learn more about your ad choices. Visit podcastchoices.com/adchoices

Have you ever thought about investing in the wide world of real estate but weren't sure whether it was for you? Today's guest, Michele Cagan, says that it probably IS for you...but maybe not in the way you'd traditionally think. Sure, you can go fix up and flip houses or become a landlord, but Michele shares LOTS of other ways to invest in real estate as well, and gives us five reasons why you should at least think about it. Whether you're a seasoned real estate investor or newbie, there's something for everyone today in Michele's visit to the basement! In our headlines segment: what's the WORST age to take social security? How does the system work in the first place? While it's complicated, we'll share the worst of the worst AND give you some basics on how to start thinking about YOUR payout. In our second headline, Charles Schwab is seeing HUGE returns from their new hybrid robo-meets-human advisor program. It seems these people chasing robos might just want some human advice...strange (smell the sarcasm in that sentence? We'll explain.) After a dose of Doug's amazing trivia, we'll throw out the Haven Life Line to a lucky caller, as usual. Just another fun day here in the basement... Thanks to Clearbanc for supporting Stacking Benjamins. Are you doing over $10,000 a month in revenue? Find out how you can receive Clearbanc capital by getting your 20 minute term sheet at clearbanc.com/SB. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Do you want better answers in your life? It may seem like a simple solution, but Andy Andrews, New York Times best-selling author, says you just need to be asking better questions. He'll share secrets from his new book, Bottom of the Pool, on today's show! In our headlines segment, we'll ring up Christine Benz on Joe's Dad's shortwave radio. She's the director of personal finance at Morningstar, and we'll ask her how some of our listeners who are new investors can get their retirement plans rolling. In true Andy Andrews spirit, she'll make sure you're not just asking questions about your retirement plans, but asking the right questions. Plus, in our second piece, one article says that millennials should be the new face of the retirement crisis. As two guys who are NOT millennials (but often act like millennials), Joe and OG share their thoughts. During our Have Life Line, we'll answer a voicemail from Bill, who has a life insurance policy with a cash value. Bill's thinking about stopping it and putting it into a long term care policy or something similar. Thoughts? Thanks to AcreTrader for supporting Stacking Benjamins. Learn more at AcreTrader.com/sb. Learn more about your ad choices. Visit podcastchoices.com/adchoices

The Fintern is finishing out our rewind week with one of our old school roundtable favorites: we're talking about lies about retirement. You can read the original show notes below: On today's podcast we're talking about lying. A recent news piece reports that there are nine lies we're told about retirement planning. We'll break them down with Greg, Paula, and special guest Rich Jones from the hit podcast Paychecks and Balances. We won't stop there, thought. We'll also discuss a recent question to the Moneyologist at MarketWatch. If you had two kids and one was irresponsible, would you disown him? We ask our roundtable that very question and come up with some interesting estate planning themes you may want to address in your own planning. On the Freshbooks FinTech segment we talk to Michael Asare from Fee Belly. Ever feel like the fine print in a contract is completely against you? Fee Belly was designed to show you ALL of the fine print by highlighting it so you can easily see where contracts might not be in your favor. We'll ask him how it works on today's podcast. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Time for something a little different in the basement! While it's still "rewind week" here, instead of playing an old SB episode, we instead are serving up our little sister show, Money With Friends! This show appears six days a week wherever you listen to Stacking Benjamins. Money With Friends is news and commentary with diverse thought leaders. It's performed in front of a LIVE Facebook audience. This show originally appeared Monday on that channel. If you like it, head on over and listen to today's show as well! We'll have more SB on Friday, with another rewind treat from the FinTern (new shows back on Monday!). Learn more about your ad choices. Visit podcastchoices.com/adchoices

Welcome to our Stacking Benjamins rewind week! Normally doing this week we would play you some of our favorite episodes from the past that you may have missed... but this week we're mixing things up. Monday and Friday will go as planned, but stay tuned on Wednesday for a special surprise. The Fintern is kicking off the week by queuing up our time with Shannyn Allen, who lost over $50,000 to a hacker. We won't spoil the interview in case you missed it the first time around, but this is one emotional, honest story that you definitely want to hear. You can read the original show notes below: What would happen if you lost more than $50,000 that was meant for your first home? Shannyn Allen lived that harrowing nightmare and she's going to share the story today. She unknowingly handed a hacker $50,000 , and will share the mistakes that were made around her situation, and will also let you know the steps YOU should take if you're even in a similar situation. It's a raw, horrifying story, and also one of the longest interviews we've done on Stacking Benjamins in a long, long time. In our headline segment we talk about Beyonce and Jay-Z. It appears they're spending money like they're....Beyonce and Jay-Z. What does that have to do with you? We'll share that on today's show. Also, Jamie Wise from the Buzz Indexesshares with us some welcome news about oil prices. Are we seeing the lows in oil? He'll share the wisdom of social media chatter on today's podcast. Of course, that's not all. Doug has yet another hare-brained scheme to become wealthy....but still has time to share some trivia. We'll also throw out the Haven Life Line to Nikki, who asks an existential question about money and goals, plus answer a letter from Jason about the Roth IRA. Special thanks to M1Finance 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

What do YOU worry about when it comes to money? Is it the same thing others worry about? Today we head to sunny Orlando, the home of Podcast Movement (the nation's biggest podcasting conference), and catch up with some top financial podcasters at the FinCon booth in the expo hall (they were nice enough to set up a podcasting booth for shows to use!). Today we talk to Mindy Jensen from Bigger Pockets Money, Lacey Langford from the Military Money show, and all the way from Australia, the host of one of the biggest money shows in the land down under called My Millennial Money, Glen James. We'll take a break at the halfway point to finish off our Labor Day prep week. OG and Joe will share a cautionary tale about inviting your FIRE (financial independence/retire early) friends over for your Labor Day cookout. His event last year went really, really poorly. He'll explain. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever walk into a wine store and wonder what all the labels mean? Looking for a way to upgrade your Labor Day celebration without spending a ton of money? Today, wine expert Dave Falchek from the American Wine Society joins us to talk all things vino. How do you pick a wine? What are some clues that a wine is good for your party? What do those ratings mean in a wine shop? What wines go best with burgers and dogs? We'll answer all of those questions and more on today's show! In our headlines segment, we'll find out why a half a ton of weed was returned to the seller as it was going public. One new billion-dollar pot company is to blame, and the stock price isn't looking great. What does this mean for cannibis stocks in general? Of course, Joe and OG both have opinions. Also, a recent New York Times piece shares how the next recession might start. We'll walk through the possibilities and also maybe look into the crystal ball ourselves. After a little dose of Doug's trivia, we'll throw out the Haven Life Line to Peter, who wants to know if he made a mistake by taking his Roth IRA fund out to help pay for real estate. Thanks to Clearbanc for supporting Stacking Benjamins. Are you doing over $10,000 a month in revenue? Find out how you can receive Clearbanc capital by getting your 20 minute term sheet at clearbanc.com/SB. Learn more about your ad choices. Visit podcastchoices.com/adchoices

We're celebrating Labor Day in style (and a week early) with Frankie Celenza, the chef at Struggle Meals on the Tastemade network. We'll talk not only how to make your holiday weekend grilling perfect, but also how to make smart and frugal food choices in the kitchen. Not only will he share tips on how to make your perfect burger, but also grocery ideas in general, how to make sauces, and the key to that recipe in front of you. Before our fantastic chat with Frankie, we'll discuss the retirement danger zone. Could the early years of retirement make or break your golden years? We'll cover what you SHOULD be worried about when it comes to retirement, plus we'll also give our two cents on one piece from InvestmentNews that shares five reasons why even the staunchest of Roth IRA lovers might want to think about leaving some of their portfolios in traditional IRAs. After we take a break for some Labor Day trivia from Doug, we'll round out the show by throwing out the Haven Life Line to Susan, who's mother needs $1800 a month for her assisted living facility. Her mother has a sizable nest egg split with some of the allocation going into a total stock index, and some going into a total bond index. Which of the funds should be in a Roth account. Does it really matter? Thanks to Clearbanc for supporting our show. If you’re doing over $10,000 a month in revenue, find out how you can receive Clearbanc capital by getting your 20-minute term sheet at clearbanc.com/SB. Thanks to AcreTrader for supporting Stacking Benjamins. Learn more at AcreTrader.com/sb. Learn more about your ad choices. Visit podcastchoices.com/adchoices

We see people without children retiring early all the time. Is that because children are the speed bumps on the road to the financial heaven? We'll ask our panel for their thoughts, including a woman who has six kids and is chasing financial freedom, Wendy Mayes from the House of FI podcast. We'll discuss meal planning, where you live, your transportation costs, child expenses and more, on today's show. Halfway through the show, our roundtable discussion will take a break for our Fintech segment. School is back in session, which means it's time to buy school supplies. Brad Williams from Mercari joins Joe in the basement to introduce their app which helps users buy or sell gently used school supplies. Find out what Mercari is all about and what their company can do for you and your wallet. Plus, we'll answer a voicemail from J during our Magnify Money segment. J is getting married in a few months and wants to know how to effectively introduce money management to his future-spouse. J also wants to know the middle ground in putting a budget in place that the family agrees to. Thoughts? Thanks to Grammarly for supporting Stacking Benjamins. Get 20% off a Grammarly premium account, go to Grammarly.com/sb Learn more about your ad choices. Visit podcastchoices.com/adchoices

Len Penzo is the king of the sandwich study...and of independent thinking ABOUT sandwiches (and many, many other topics). On today's show we dive into the latest iteration of our favorite way of talking about inflation: comparing the rise and fall of prices among popular school lunch/work brown bag sandwiches. How much do different sandwiches cost? How much more do they cost than last year? What are the most inexpensive sandwiches? Which have changed in price the most? If you're looking for a deep dive into the world of sandwiches, today is the show for you. In our headlines segment, we will learn what the ten stocks millennials just cannot live without. What are they? How do they compare with the stocks you SHOULD own? We'll tackle both the top 10 list and attempt to answer that question. Plus, what is a small cap REIT and should you think about one in your portfolio? We'll talk about diversification during our second headline. After a little dose of Doug's sandwich-themed trivia, we'll throw out the Haven Life Line to a lucky caller. It's another fun show with lots of twists and turns...just another day in the basement. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today we sit down with Rob Berger, host of the Dough Roller podcast and author of Retire Before Mom & Dad about the five lies we all are told about money. Because we fall into these traps, we're duped to live a life on the hamster wheel, working harder and harder, but getting nowhere. Today we'll talk about debt, investing, insurances, advisors and more, so that you can take charge of your finances. Plus, during our headlines segment, we'll cover one piece from Financial Planning about an ex-advisor who is off to prison for duping his clients with a Ponzi scheme. What did he do wrong? We'll share. We'll also jump into some big news from the IRS. One product's tax treatment with regard to advisor's fees is changing. That may change the way advisors...and YOU view that particular tool. And after we take some time for some of Doug's french fry themed trivia we'll take a voicemail from Jason during our Haven LifeLine. Jason wants to know our thoughts about funds and strategies that will deliver the highest risk-adjusted return. Should he be 100% equities with his money or something safer? Thanks to Grammarly for supporting Stacking Benjamins. Get 20% off a Grammarly premium account, go to Grammarly.com/sb. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today our roundtable discussion focuses on one set of homeowners who successfully sold their house, but realized that they could've saved $60,000 if they had instead rented and never purchased the home in the first place. Is buying a home a waste of money? Did the couple make some big mistakes that we can all avoid? Did they use professionals wisely or make some bad decisions? Discussing this headline with us are three veterans of the financial blogging and podcasting community: Tom Drake from MapleMoney.com, Paula Pant from Afford Anything, and Len Penzo from LenPenzo.com Halfway through the show, we'll take a break from our rent vs. homeownership discussion while Joe sits down with Jean Statler from the Alliance for Lifetime Income. The organization is working with MIT's AgeLab on an important issue: the risk that we might outlive our savings. Jean reviews the problems the public has had with annuities and dives into the discussion of what the industry is doing to clean up perceptions and simplify products. It's a very frank and enlightening conversation about an often maligned financial tool AND the issues surrounding living longer. During our Magnify Money segment, we'll take a call from Kurt, who has a question about his workplace tuition reimbursement. If Kurt doesn't stay with his employer for three years he owes back all of the cash his company gave him for school expenses. Right now he has the amount sitting in a savings account, what should he do with it? Should he invest it? Pay down debt? Leave it in savings? Our team bounces around several possibilities. Thanks to Grammarly for supporting Stacking Benjamins. Get 20% off a Grammarly premium account, go to Grammarly.com/sb. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Who wouldn't want to be one of the Grateful Dead (love the play on the rock band name, don't you?)? Today we'll ask the question, "When's the last time you've thought about your estate plan... (if you've made one)?" Making a will or even a full trust may seem like a daunting task that's best done tomorrow, or the day after that, but we all know that it's an important piece of your financial life that shouldn't be overlooked. To help us understand the ins-and-outs of estate planning in the most fun way possible (and MAN is it fun...), we've invited down the woman who literally wrote the book on it: Carol Weisman, author of Becoming One of the Grateful Dead. In our headlines segment, we're getting a little political today with our first piece. With the election cycle revving up, some politicians have been talking about paying for different campaign promises by enacting a tax on some financial transactions. Is there cause to be worried about the bigger retirement picture if more taxes are thrown in the mix? After we've had our fill of politics, we'll stick around the stock market as we discuss our second piece: a robo-run ETF has been making a splash by beating the overall stock market. Later, we'll throw out the Haven Life Line to Ian, who has now realized the mutual fund he picked has higher fees than he would like. He's down 11% right now, but should he hold onto his fund knowing about the high fees? A big thanks to Student Loan Hero for supporting Stacking Benjamins. Find out how you can pay for college AND compare different interest rates before locking into a loan at StudentLoanHero.com Learn more about your ad choices. Visit podcastchoices.com/adchoices

While we all love talking financial independence, side hustles, and paying off huge amounts of debt, another topic doesn't get enough attention, mostly because it's difficult. We don't pay nearly enough attention to the biggest threat facing any retirement: long-term care. What happens if you have a catastrophic illness and can't take care of yourself? Nursing homes are expensive, home care is expensive, and asking loved ones to take care of you can be horrible for their health and wellbeing also. Today we'll talk to Shawn Britt from Nationwide Insurance, who as a long time professional in this field, knows the statistics and the horror stories, but also the common sense approaches to many illness-related problems. We'll talk planning, the good/bad/and ugly of long term care policies, but mostly about maintaining flexibility and options as a result of making informed decisions before life makes those decisions for you. In our headlines segment, the Fed is unrolling a plan to create a faster money transfer system. We'll discuss what could be the end of the three day wait for money transfers between many institutions, and, of course, what that means to you. Plus, in our second piece, a Swedish online payments company has been valued at $5.5 billion - making it Europe's biggest FinTech start-up ever. Also? It's backed by Snoop Dogg! The firm, Klarna, purchases products from companies on behalf of the consumer and bills customers over time. Is this a dream come true or a recipe for disaster? We'll cover the implications, good and bad, during our headlines segment. We'll finish out the show by throwing out the Haven Life Line to Jason, who has a totally serious question about investing everything he has into a glide path. Currently Jason is 100% investing into the Vanguard total bond fund. Here's the issue: the expense ratio is 0.15%, while the Schwab total bond fund is .014%. It makes sense to move his money over, but that could cause him to incur a $32 tax hit. What's Jason to do in a dilemma like this? Don't worry, we'll give him some advice straight from the heart. Thanks to Grammarly for supporting Stacking Benjamins. Get 20% off a Grammarly premium account, go to Grammarly.com/sb. Thanks to AcreTrader for supporting Stacking Benjamins. Learn more at AcreTrader.com/sb. Learn more about your ad choices. Visit podcastchoices.com/adchoices