The Stacking Benjamins Show

How do you make money driving for ride sharing companies? Credit card hacking? Churning bank accounts? How do you help your family plan? What's it like to meet with financial advisors? Today members of our community, Alan, Claudia, and Jon are kind enough to share their wisdom and experiences in all of these areas! Plus, we'll also share an important headline about doing your homework before investing, another on helping your community, and more. Of course, we'll also throw out the Haven Life line to a caller with a great question about estate planning. That comes after Doug's trivia and a few of your emails. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How much of this stuff goes over your head? What are the absolute first things you need to know about when you're rolling out on your own? Today high school personal finance teacher and author Jake Cousineau joins us to dive into the very first items you should include on your list of lessons to learn about money as you begin your journey. From the double-edged sword of interest to simple banking and ideas on budgeting and saving, we'll share some of Jake's favorite tips so that you can leave today's show more prepared than you were before you listened. Annuities Changing Standards: Our Headlines States are rolling out some new rules around annuity sales, which largely are meant to mimic the SEC's Reg BI (best interest). While industry spokespeople say it's a step in the right directions, consumer advocates say it isn't enough. Today we'll share how annuities work, where the problems are in the industry, and how these new state-by-state rules may change the game (or not). We'll also share our TikTok creator video minute, and today we'll share a refreshing story. An online "guru" actually apologizes for leading his followers into a scam. While we love the sentiment, who would have known (hear the sarcasm coming?) that a StarWars universe-themed crypto coin called Mando might be fake. We'll also share the latest worldwide real estate news. Inflated prices aren't just happening in your back yard. Around the world we're seeing some eye-popping numbers. What's the takeaway? We'll talk real estate today! Of course, we'll also throw out the Haven Life line AND save time for Doug's trivia. It's another great day in the basement! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Are you coasting or actually planning your next move? Living in the land of "I should" or "I might" versus "I'm where I want to be right now?" Whether it's balancing your happiness with your career choices, changing industries, family planning, or deciding how long you want to work until retirement - lifestyle choices encompasses all of our financial decisions. Today we ask our contributors: what's the design for your lifestyle? What drives your motivations, career choices, retirement plans, and financial decisions? It's a great discussion with plenty of overlap with financial independence, and one you can use for a diagnostic in your own life once you hear how it's done. Welcome to a live-making of the Stacking Benjamins show! Recorded during Podbean's Finance Podcast Week, we had the opportunity to showcase a behind-the-scenes making of the podcast in front of a live audience, and it was lots of fun that you'll hear today. Our round table has a big discussion on lifestyle design this week using their cell phones. For this one, excuse our worse-than-usual audio. We promise the engaging conversation will be worth it. Our Listener Mail: What (Non-Financial) Podcasts Do We Like? We finish our live show with a letter from Lou: he's heard us talk plenty about our favorite TV shows and movies, but what about our favorite non-money related podcast? Our contributors deliver: from podcasts like Whatever Happened to Pizza at McDonald'‪s‬ and Betty in the Sky with a Suitcase‪!‬, to This Week in Virolog‪y‬ and more, you'll hear plenty of our favorite podcasts we love to binge when we're not thinking about money. (Except for one contributor who always is thinking about money - but we'll leave that one a surprise). Of course, we couldn't possibly do a live show without giving up some airtime for Doug's trivia. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Don't think you can overthink your money decisions? Study's show that sadly, you're wrong. Not only will overthinking cause you to create overly complex plans, but you'll give up early on strategies, fail to move when you need decisive action, and exhaust yourself with going over the options "just one more time." Overthinking rarely involves positive thoughts, and you can't win when you're not confident. Today we'll help you solve that issue. Long time listeners will remember the last time we had Jon Acuff on the show back in 2017, (find that here: Give Yourself The Gift of “Finished”). In Jon's new book Soundtracks, he explores how our thought process and the stories we tell ourselves impacts our everyday lives, AND how you change your own soundtrack to solve your problems with overthinking. Give Enough Cash and Even The Spenders Pay Up... Eventually Remember the news the weeks after the first stimulus checks hit? Everyone waiting for the first piece of evidence to release their blog posts and podcast episodes about how everyone ran out and bought fancy 4k's and PS5s? (We totally didn't do that...not us!) Well, a new study shows that given ample cash to clear out the Amazon wish list, many people HAVE ended up paying off their bills. During our headlines Joe and OG discuss paying down debt, the double penalty of being stuck in a debt cycle, and how you can walk away from the I Can't mindset. How The Pandemic Changed Our Retirement Worries The pandemic challenged a lot of the conventional thinking behind emergency funds, healthcare, and and retirement living. A newly released Fidelity report queried investor retirement worries, and while there were some surprises, other figures proved that not all financial thinking needs to be redrawn from the ground up. Doc G from the Earn & Invest podcast joins us today to discuss what the report means for the broader retirement conversation AND what the numbers mean to you. The Haven Life Line: What's the deal with Fundrise? Sean is interested in investing with Fundrise, and wants to know our thoughts. While the company has seemed to change up their marketing since they first came on our radar we still have some reservations, and OG and I actually differ on a few thoughts here. Never familiar with REITs? We'll explain your options on the show, but you can get started here: Traded vs. Non-Traded REITs: Which Is Best for You? Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

This seems like an easy decision, doesn't it? Skimp on the party and invest money in your dream residence. Yet, don't we always say to invest in experiences because they appreciate in your mind (becoming more epic as the years pass), instead of things that clutter our lives? Co-hosts of the new Netflix reality show Marriage or Mortgage, wedding planner Sarah Miller and real estate pro Nichole Holmes, join us for a fun discussion on a dilemma many newlyweds face: how much cash do you spend on making your dream wedding a reality, and at what cost to your future home? We know, this is a financial podcast, and financial nerds are definitely biased on this one, but Sarah raises some pretty good points, and you just might surprise yourself when you're nodding along. We're not saying you should go for broke on a huge wedding (though if you do, please invite us), but Sarah's reasoning isn't exactly in contrast with our own money philosophy. Making "Fun Money" on trading apps? Watch out for the tax bill. In our headlines segment, we'll relive the horror story one Robinhood trader experienced when he found he had an $800,000 tax bill. Worse news? He could have avoided it fairly easily if he knew one rule that we'll share on today's show. Tiktok of the Week: Amazon beats Walmart because of... adult toys? In our TikTok minute you'll find that it isn't just young, aggressive traders (or at least TikTok talkers) who are making bizarre statements about financial success. So are television anchors. Want early retirement? Try buying a school bus! How great is this? One man in his twenties decided to cut out 40 years of saving and instead retire right now. We'll share his story and what it means for you. BUT that's not all. Of course, we'll throw out the Haven Life line to a lucky listener AND we'll dovetail in some of Doug's amazing trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Brush off the passport, pack the bags, and plop down in your favorite lazy spot because we're going global on today's show! In this special Living Abroad episode, we invite world travelers living in various countries to share how they did it, what they should've learned earlier, and what life experiences they've gained since settling into their new lives. Joining our round table is a French native and former Guatemala-living Pauline Paquin from the Reach Financial Independence blog, Jim White from the Route to Retire blog (who moved to Panama with his wife and daughter at 43), and Travis Luther, author of Fun Side of the Wall, a book explaining why baby boomers are flocking to Mexico for retirement. Friday Fintech: Jassby - An App for Families After our trio wraps up all things travel Joe sits down with Benny Nachman, founder of the family money-sharing app Jassby. The app provides an easy-to-use system that lets parents assign responsibilities to children, pay allowances, and even setup a virtual debit card. Listener Voicemail: Gifting Stocks? During our MagnifyMoney segment, we take on a question about gifting stocks to students from high school teacher Jake. Additionally, he asks, is there a good way to buy fractional shares as a gift? A few of the stocks his students are interested in are a few hundred dollars a piece... not exactly feasible to buy for a whole class. As always, Doug has some post-Fintech airtime to deliver his game-show trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

You may have financial security, but do you have financial wholeness? What's the difference? Tiffany "The Budgetnista" Aliche says that she felt more whole BEFORE she had financial independence than she did after. We'll talk about building a solid financial footing and understanding on today's show. Tiffany has led women worldwide in paying off millions of dollars in debt, co-hosts the Brown Ambition podcast, and now has multiple financial education books published, including a pre-education book for children. With a decade of teaching experience behind her - that's before she moved into financial education - Tiffany has used her experience to develop easy-to-follow, engaging financial education lessons. Today we sit down with The Budgetnista for a wide-ranging interview including why you should strive for financial wholeness instead of financial freedom, how to present financial education so even children can grasp it, and her straightforward budgeting system. A Case Study in Being Prepared Model and Actress Brooke Shields had a horrific fall a few months ago that required her to undergo multiple surgeries. It's an accident she's still recovering from, and one she'll need to dedicate time and resources too. Here's the thing: Brook Shields (in all likelihood) can field the costs and loss of earnings in stride. What would happen in your life after enduring the same experience Shields went through? Beyond the physical and emotional trauma, what type of shock test will your finances go through? What vehicle gets the most mile for your buck? Pushing mortgages and health costs to the side for a moment, vehicle purchases are among the most expensive reoccurring expenses you'll have in life. Operating inside of a budget, there isn't anything wrong with picking based on your aesthetic preferences. However, at the very least, you should make informed decisions when any large amount of cash in on the table. We know cars depreciate in value the moment you drive off the lot, but which vehicles actually get you the most mileage for your cash over the long run? Joining us today with all the right answers, we welcome Karl Brauer from ISeeCars.com. Getting Young Investors Started? Sarah calls in asking the best way of setting up investment accounts for her two younger brothers, who are 16 and 20 years old. She knows her older brother could possibly setup a Roth IRA, but not sure what the best move is for her youngest brother. Sarah also asks about college financial aid implications. Thoughts? Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Pros in every field will tell you that confidence is a huge part of earning more money. But what happens when life delivers blow after blow? We've been there ourselves, and so has our guest, Harma Hartouni, who moved to America with his family and was flat broke. Much of his story stems from a childhood relationship with a dad that was less than perfect (to put it mildly). While this is not a direct rags-to-riches story, things started to turn around for Harma, and he now runs one of the top real estate firms in Southern California, along with having a passion for sharing his life experiences for others to learn from. Today Harma shares his compelling story of perseverance, confidence, and learning lessons from horrible experiences instead of falling back on them as a crutch, like so many do. Blackrock Cuts ETF Fees Cut to Near Zero Lower fees... hooray! Right? The race to zero fees continues with BlackRock's latest move to drop ETF fees, which is the lastest blow in their fight for assets with Vanguard. While we aren't complaining about more money in your pocket, the slashed fees leave us with a lingering question: what exactly should investors want when it comes to their strategy? Beyond the latest flashy headline of the week, what's your framework for making investing decisions? Top Mistakes People Make When Planning for Retirement Have you made your portfolio more conservative to soothe your market volatility fears? Larry Swedroe recently shared some big retirement planning mistakes which could cost you millions of dollars in missed opportunity. The Your Complete Guide to a Successful and Secure Retirement author (and previous Stacking Benjamins guest) brings some good points to the table, and Joe and OG share some math scary enough to make you think twice before slowing things down. Not All Products Are Meant for You We're mixing things up with today's Haven Life Line. Margaret saw a video online that's filled with mostly good advice, but sneaks in a "secure compound interest account" comment at the end of the clip. What's the deal? Joe and OG share exactly what this account actually is, and give some frank advice for people who may be considering investing. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Have a difficult time separating good financial advice from the bad? Today our contributors tackle everything from budgeting and credit utilization myths, to discussions on trade schools and the rent vs mortgage debate. Joining us on today's round table is Lauryn Williams from the Worth Listening podcast, Paula Pant from the Afford Anything Podcast, and Len Penzo from the LenPenzo.com blog. Friday Fintech: FarmTogether After the constant reminders to diversify, you eventually decided to invest a portion of your portfolio into something like bonds, right? Ever consider farmland? Joining us from the FarmTogether investment platform, we welcome founder Artem Milinchuk to learn more about farmland investing. Joe and Artem discuss how farmland's low correlation with the stock market provides better diversification, how advances in the farming industry align with ESG values, and how farmland can provide bond-like stable returns while still providing equity-level value. Listener Voicemail: What Happens To Your Stocks When A Company Goes Private? A company you own stocks of goes private, what happens now? Caller Liz recently found out that Michael's will become a private company after a sell. Liz asks: do they sell her shares at a specific time? Does she have a choice? Fortunately, Liz tells us this is her sandbox money - she doesn't need it, but she's still curious about the process. As always, Doug has some post-fintech airtime to deliver his game-show trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

We thought women have been doctors for a long, long time. That's clearly not been the case, and also it's a path that's hard-won. If you were fans of the women in Hidden Figures, watch out, because today we're introducing you to three more trailblazers. In honor of Women's History month we invited Olivia Campbell, the author of the new book Women in White Coats, to share with us some fascinating (and sometimes horrifying) stories of the challenges these incredible women faced during their fight with the status quo. These women had limited funds, little to no support system, no government assistance, and they persevered in spite of it all. Financial Advisor Alex Reffet In our headlines segment, we'll go back again for another look to a year ago. How should a good financial advisor have encouraged you at the time when the sky was falling, and the market was experiencing its worst days in history? We'll talk to Alex Reffet from East Paces Group in Atlanta to get his perspective. Tax Day Pushed Back...BUT With One Exception Also, we'll share the news that you can procrastinate on all of your taxes...except one, for an extra month. We'll share some bad news for people with a state income tax AND also for people who own businesses. Of course, we'll also throw out the Haven Life Line to a lucky listener AND share Doug's amazing trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How many mistakes did YOU make buying your last home? Before you make another, Scott Trench and Mindy Jensen from Bigger Pockets Money join us to drop the knowledge you should know before making your next home purchase. They'll discuss the cost tradeoff you need to consider between renting and buying, the exit strategies you have to weigh before making any purchase, and detail how to set yourself up for a rock-solid home buying experience. Plus, you'll see how Mindy pocketed a $300k profit off her home renovations, tax-free. Cryptocurrency illegal? We'll start our headlines discussing India's possible banning of cryptocurrency. While nothing is yet set in stone, it's a good example of why it's important to keep your retirement funds diversified, no matter how lucrative one type of investment may appear. The only thing that's for certain is that if there's a way to make money off of it, you can bet Uncle Sam (or any government) is going to find a way to share in the pie. 2021 - The Year of the CFO We'll start with a piece about a possible market crash (spoiler: yes, eventually), and quickly pivot to a discussion on how careful you need to be this year about growth statistics from companies. With the year that was 2020, it's no wonder companies are loud and proud about their expected growth in 2021. Don't get us wrong, we're excited about positive news, but as an investor, you can't only rely on fancy numbers. What to do with all this money? We'll finish the show with a call from Seth, who recently bought a home. After his monthly expenses and investing Seth has about $2,000 leftover each month in savings. With Seth's emergency fund already fully funded, he asks: should he allocate the extra cash to paying off his mortgage, or use the money to fund additional investments? We'll give Seth some advice that'll work for every raise he gets, expected or not. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Whether you are a parent, have parents, or find yourself at the Thanksgiving table sandwiched between generations, honest money conversations are crucial to your financial journey. Single investors with no kids need to know the late-life plans of their parents before they're surprised with care costs. Kids themselves need financial education and the best way to do that is by showing them firsthand. Parents, especially those supporting two generations, have all the more reason to make sure everyone is on the same page. Joining us today to share the strategies and conversations inside of their own families, we welcome Pam Andrews from The Scholarship Shark; Doc G from the Earn & Invest podcast, and OG from our own Stacking Benjamins. Friday Fintech: Ethical Investing with Seeds Investor Remember 15 years ago (or even five) when investing in ESG's was considered principally an ethical move? While you could invest according to your morals people would tell you about the market returns you'd miss out on. That's not quite the case anymore, and now it's easier than ever to stick to your ethical considerations AND make money doing it. Joining us today from Seeds Investor to discuss the future of ethical investing and Seeds part in it all is COO & Head of Product Kristen O’Grady. Our Listener Voicemail Dan graduated from college last year and has been staying with his parents rent-free. He's since become a salaried worker, with a big raise and benefits to match. Dan tells us that he had been putting 15% of each paycheck into a savings and emergency fund. He has a few manageable bills right now and has been investing the rest. Dan asks: what are out thoughts on transferring the 15% savings rate to his investments instead? After all, he could maximize his investments while having low bills. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today's show includes two fantastic guests: first Allison Baggerly, who not only paid off $100k on two teacher salaries but who also has become a ninja at budgets. She'll share tips from her Inspired Budget courses and website that you can use to begin setting up your own budget today. But that's not all! We also spoke with the host of Struggle Meals, Frankie Celenza, about how he's able to make great-tasting food for less money AND with less waste. He'll share tips about spices, salt, organizing your refrigerator, and more. NOTE: On the live replay we experienced a few issues. We'll share one right at the top of the show (Doug's power went out immediately as we began--that stuff ONLY happens when you're live). We also realized while editing that you are hearing also Joe's channel, which includes links to backstage discussions. We've cleaned it up a ton and unfortunately, that meant cutting some discussions. Check out the YouTube video to see the entire show. As always, you'll find show notes and links to Struggle Meals and Inspired Budget at our show notes page at Stacking Benjamins dot com. Learn more about your ad choices. Visit podcastchoices.com/adchoices

You calculate returns on your investments, but what's your ROI when you're actually being nice to people? It turns out, reams of data show that kindness pays, and today, America's Breakthrough Coach, Brian Biro joins us to talk about how to become a Chief Kindness Officer. While Brian's all about holding the door open for someone, the philosophy of kindness actually goes much deeper than that. Sometimes being kind means telling a worker, "Go figure this out on your own, then come back to me with your thoughts." It's a wide-ranging interview that we know you're going to enjoy. Bad Idea of the Year: Investing Because A Celebrity Said So The Securities and Exchange Commission has a new warning you'll want to know about. If you didn't know this already - you shouldn't invest in any company only because you heard something on the internet and the news. That includes Stacking Benjamins, Facebook, CNBC, Fox Business, and anyone else you want to throw on this list. That's not to say no one ever has good endorsements, but due diligence is always an action you should take before making big decisions with your money. We'll talk about celebrity endorsements and a new warning from the SEC during our headlines segment... Have A Plan For That $1,400 Stimulus Check Coming In And speaking of doing your due diligence, Suze Orman had a thing or two to say with how people might be spending this next stimulus check. Naturally, we had a thing or two to say about her thing - or rather Don McDonald has something to say. Making a flash appearance in the basement, the Talking Real Money host has some real takes on how you should use your stimulus check to score the biggest impact possible. What's the deal with SPACs? Good on Julien for today's Haven Life question! He's been hearing about special-purpose acquisition companies (SPACs) in the news and wants some clarification. Is this a new shady method for companies to avoid the paperwork that comes with an IPO? Are SPACs worth investing in? Joe and OG take Julien's question and go step-by-step on the differences between IPOs and SPACs. Of course, we'll always leave some time for Doug's trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Spend less than you earn, invest, Stack Benjamins, and retire to a beach for the rest of your life, (or insert personal retirement fantasy here). It sounds simple... right? As a set of guidelines, sure it's simple. BUT in reality, it's not so easy, and as studies have shown time and time again, doing your dream retirement activity (like golf) every day gets old very quickly. While money is obviously the most important component to any retirement, the "to-do" list doesn't stop there. Helping us fill in the blanks, and joining us for our round table today, we welcome CFP Dana Anspach from Sensible Money, Len Penzo from the LenPenzo.com blog, and our very own OG. EverPlans: Introducing a company helping you plan for the worst. After our contributors get their fill on retirement advice, Joe sits down with the founders of Everplans, a company designed to help you store key information in one place in case of the worst happening. During our Friday Fintech interview, company founders Abby Schneiderman and Adam Seifer explain why it's so important for your loved ones to have easy access to your important documents, and how quickly things can go wrong when your family can't access your information. They take a topic most of us would rather put off and share stories that are fun, insightful, and actionable. We're glad to shine some light on the importance of making sure your family is taken care of in case of the worst happening. Should you hold onto bonds for a change to make money on the market? As always, we finish today's show with a MagnifyMoney question. Scott tells us he's holding long-term Treasury bonds in his portfolio with the hope the bonds will jump in price when the stock market crashes. He would then use the profit to buy stocks while they're low. Scott asks: do long-term treasuries still spike in a near-zero interest rate environment, or does that only happen when rates are cut? Of course, Doug gets airtime halfway through the episode for his game show, and he's in the holiday spirit today. You'll see what holiday season he means later... enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

You've felt it. You're going over the side...and it's all crashing down. You'd better believe that Heather Chauvin has also felt it. She's both a leadership coach and host of the Mom Is In Control podcast, and today she joins us in the basement to share her personal story of leaving a job she hated, all while maxing out her credit cards to get her side business off the ground - and by the way....also while she was battling cancer. While sitting down with Joe, Heather also shares how she stayed motivated and shifted her life priorities from taking care of others first, to taking care of herself first - and then others. Putting her own "mask" on first (talking airline warnings here) changed her life, and it'll do great things for you too. Financial Lessons From Sky-Rocketing Lumber Prices.In our first piece, we share lessons learned from rising lumber prices across the country. Much like how we love to wait until the day before a cold front to make necessary preparations, lumber runs on a "just in time" system. When an extra factor is thrown in the mix, it can throw the whole system in disarray until enough time has passed to course correct. A financial plan made with margin for error runs close to the same fashion. The big issue? Late lumber impacts your backyard plans, a wrong financial plan messes with your retirement. Joe and OG give their takeaways during our headlines. Mortgage Rates Are Creeping UpMortgage rates are going back up, better run out and capitalize on it while you can!... or maybe not. Giving us some clarity in what is surely resulting in plenty of scary headlines, Joe sits down with Kevin Parker of Navy Federal. Kevin shares what you need to know BEFORE making any big money decisions, plus dishes out some sound financial knowledge that's helpful for anyone approaching loans and credit. Best Personal Financial Success Story?Waiting for us on the Haven Life Line is a question from Evan, who's looking for some feel-good news after 2020. He asks: what are our best personal and professional success stories? We're happy to share! Of course, we'll always leave some time for Doug's trivia. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

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

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

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

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

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

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

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

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