The Stacking Benjamins Show

Rewind Week! Throughout the week we'll replay some of our favorite shows from the past. We're kicking Monday off with an interview we've had plenty of compliments on. Newer listeners will appreciate this one, and older listeners will find Annie Duke's interview refreshingly timely. Our original show notes are below.Do you think you make the best decisions under most circumstances? Today’s guest will tell you that if you don’t have all of the information, the more adamant you are about your point of view, the easier you are to “beat.” Annie Duke was a professional poker player for 20 years, winning many top tier professional tournaments and taking on the best decision makers alive. Equally as important, she brings her academic career in cognitive psychology to bear on decision making that can help you with everything from your investments to your career and more.In our headlines segment, parents are spending TONS of money on their children’s extracurricular activities. Beyond avoiding vacations or planning vacations around some of our people, some parents are stopping contributions to their retirement and not putting money in college funds…just for extracurriculars. We’ll talk about what harm this does (and maybe have some surprising points of view) on today’s show. Plus, it looks like 5% interest rates on mortgages may be right around the corner. Currently, the average interest rate stands at 4.5%. What would a 5% rate do to the financial markets and to your debt load? A recent piece discusses all the different ways we’d be affected overall by higher and higher rates.We’ll of course have more from the world of financial planning, throw out the Haven Life line to lucky listener Ethan, who wonders about market cap weightings for indexes. Why do people invest in indexes that are weighted heavily toward the biggest components? We also answer a letter from John, who asks about our favorite financial books. What are they? You’ll have to listen to find out!Of course, we’ll still score with some of Doug’s delightful trivia, and more. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Wonder how your super-saver friends make pocketing Benjamins look so easy? Well, we come bearing good news because your questions are all going to be answered on today's show. MOST great savers trick themselves into saving more money and we'll dive into exactly how and what they do so that you can replicate all of their tricks. Spoiler: it's MUCH easier than you think. Michelle Jackson from the Michelle Is Money Hungry podcast will join Doc G from Earn & Invest podcast and Len Penzo from LenPenzo.com for today's exciting discussion AND Jennifer Mah from Choose FI will read today's piece we outline.Plus, remember hearing about those hairdressers that had Coronavirus? During today's not-so Fintech segment, we'll talk to the Evil HR Lady Suzanne Lucas on what that means for your job.We'll round out the show by answering a voicemail about rebalancing. While Jeff had asked if there are fees or taxes associated with rebalancing, we aren't stopping our roundtable there. During the Magnify Money segment our contributors will share their own rebalancing process. How frequently should an investor rebalance their portfolio? What should people keep in mind?Of course we'll also save time for some of Doug's amazing trivia and much, much more. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

When does buying insurance cross the line from being smart to throwing away your hard earned cash? There are the regular choices of course: car, home, life, medical, and dental insurance. But what about all the other types of coverage out there? Between rental insurance, phone, electronics, various types of worker's insurance, travel insurance (and more!), a person could easily break the budget by trying to keep 100% of their life covered. Today we'll make sure you know what type of insurance is available to you, which kinds you should buy... and of course, the types of coverage that you should probably run away from.Plus, we'll share a story of an investor who discovered a huge negative balance on his Robinhood account. We'll share the series of investing choices that lead to a tragic outcome, and the problems behind investing as sport by people who don't know many of the basics.Debt can be extremely stressful, but it is not worth your life. Help is available. You can speak with a counselor today at the National Suicide Prevention Lifeline - (1-800-273-8255) or find more help at SuicidePreventionLifeline.org.We'll also carve out some time in the middle of the show for Doug's family-themed trivia.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

In these strange times, with so much uncertainty, how do you manage your money effectively? Today we'll ask some of our favorite experts about what you should be focused on, how to pay down debt, what to do with your retirement money, and how to manage your investments.Last week we hosted a LIVE YouTube two hour event featuring some of the top names in personal finance. We were joined today by representatives from Fidelity (Ken Hevert), TIAA (Shelly Eweka), T.Rowe Price (Josh Deitch), and Morningstar (Christine Benz). Plus, Bobbi Rebell from Money With Friends podcast and Doc G. from Earn & Invest pitch in to help us ask as many questions as possible so you can be better with your Benjamins.Because this is the audio from a YouTube recording, the audio stream will be a little different, but there's still lots of great tips here for you to enjoy. Learn more about your ad choices. Visit podcastchoices.com/adchoices

You've probably heard the age-old arguments. Old dude on the radio says "all debt is bad." Your savvy neighbor says that there's "good debt" and "bad debt." You watch relatives YOLO with credit cards. Where's the line, REALLY? Today we'll ask three people who are good with money: contributors Paula Pant from the Afford Anything podcast and Len Penzo from LenPenzo.com are joined by great saver AND blogger Lance Cothern from the Money Manifesto blog. We'll dive into the good, bad and ugly of debt.BUT that's not all. On today's Friday Fintech segment we'll learn about a new company called Nestegg helping small landlords compete with the big kids. How does it work? We'll all find out together.Of course, we'll still have our trivia challenge, answer a MagnifyMoney.com call for help, and more! Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

After winning the lottery, would you go for a straight-out check OR the lifetime income stream? While people will decide which is their BEST choice pretty quickly, do you have the right information to make that choice? Today we sit down with the CEO of Saber Pension and Actuarial Services, Brent Henningson to talk not just lottery, but maybe also pensions, annuities, and life settlements. Wait a minute? Is the annuity thing just a smokescreen so we'd pay attention to something that's important but maybe not that interesting? Maybe so, but however we get you to the table, these are decisions with thousands of dollars on the table and you can't afford to make the wrong choice.Plus, is day trading easier than being a long term investor? We'll have some fun diving into why the Barstool Sports founder claims he is a better investor than Warren Buffet, and that day trading is "the easiest" game there is. David Portnoy is ALWAYS good for a quote or two. In the second half of our headlines segment, we'll share one list explaining why the RV life might not be the golden dream people are expecting. Even in retirement... informed planning is half the battle.During our Haven Life Line will answer a call from military dentist Joe (not our Joe, of course), who will be separating from service next year to pursue specialty training. While he's going through classes his only planned income will come from the GI bill. Joe's two questions are, one: can he still contribute to his IRA during his education with no taxable income? If not, would working a few days a month make him eligible? Two: he is currently maxing his Roth TSP account. Should he drop his contribution amount to get more liquidity before leaving service?As always, we're saving some time for Doug's trivia.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Want to change the world with your donations, but feel powerless? Are you unsure of the best WAY to donate money or time to an organization? Have you ever been burned by the ineffective use of the money you've loaned or gifted? Today we'll talk to someone who knows how to help you become the philanthropist you've always wanted to be. Not only will Kris Putnam-Walkerly share how to find great organizations and evaluate them, she'll also give us tips on using tools like donor-advised funds to make a larger impact (and maybe score some tax relief!).Don't worry if you like your news a bit on the harder-edged side - today's show has something for everyone: We'll ask how does an investor go from almost netting one million dollars to broke in two weeks? During our headlines, we'll look at how some investors got in over their heads in an attempt to earn huge returns... until the money train came to a screeching halt. In our second piece, we'll ask whether air travelers should expect airlines to raise fees to keep the middle seat open during the pandemic.Plus, where are the financial resources for people who DON'T want kids? During the Haven Life Line we'll answer a question from Maddie, who has become more interested in saving and planning for retirement. A lot of resources she's found so far have a focus on planning for the expense of children down the road. Maddie asks: what resources can she find for people in her situation?  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Maybe you've heard of the term "anchoring" when it comes to sales. Most likely you heard it when a fast-talking salesman threw out a couple of high figures for a fancy car just outside of your budget. (But hey! That's okay, we have some more affordable models right over here... and look, you're five dollars under your limit!) But, is it possible to use the power of anchoring to actually help you reach financial goals? In our featured piece today, which is both written AND read on-air by Emily Guy Birken, we'll dive into how you can use the power of anchoring to cut your expenses, save more money, and find financial independence more quickly. Helping us dig into the topic is none other than the co-host of the BiggerPockets Money podcast (and Bigger Pockets CEO), Scott Trench. Of course, we'll also have help from Paula Pant of Afford Anything, and our very own OG.After we're done with our anchoring discussion we'll give our roundtable a little break while Joe rings up Angelo Poli from MetPro. Did being stuck inside for months on end cause you to pack on a Covid-19 pounds? Angelo will share some great strategies to get your lifestyle back on track.We mixed things up on our Magnify Money segment this week so we could give Scott Trench a little fun. With some inspiration from a Reddit Real Estate post, we asked this question to the roundtable: What are your real estate buying/selling horror stories?Of course, we're also carving out some time for Doug's trivia.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Do you feel just a little bit lost managing your retirement funds? Don't feel like your alone. A recent study shows that MOST Americans have no clue how to pick investments in their 401k, and worse yet, even more people feel like they're investing poorly for their retirement! If you want to fix your 401k plan (that thing you save into for retirement...), we're coming to the rescue. Today we'll discuss the good, the bad, and the stop doing this before you ruin your retirement.There are MANY ways to make your 401k grow faster, but today we'll discuss how to pick better investments, save more money, stop making trading mistakes, picking better funds, and more.Later in the show we'll throw out the Haven Life line to caller AJ, who wants our thoughts on buying a property at a discount to be used as an Airbnb. With the rest of AJ's bills paid, and the 401k and other retirement accounts fully funded, AJ and her husband have put in a $460,000 offer for a $540,000 house. So, is it a good time to make this investment?As always, we'll carve out some time for Doug's trivia.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Your boss offers you a several thousand dollar raise, do you turn it down? Probably not! Yet, one of California's top real estate agents says that home buyers and sellers both regularly leave thousands of dollars off the table. That's why today we're talking about better real estate transactions with Marin County, California's top real estate pro, Tracy McLaughlin. She'll share strategies from her new book, Real Estate Rescue, for staging, updating, and pricing a house so that it sells both for more money and more quickly.We're also diving into why financial advisors are losing faith in planning software tools. With plenty of highly-rated software on the market, should you be worried that your advisor is disregarding fintech? We'll jump into the "why" during our headlines AND cover why so many Americans had to dip into their retirement funds during the pandemic.Plus, could refinancing your home loan actually end up costing you more in the long run? During our Haven Life Line we'll answer a question from Niranjan, who heard on the show that because of the way amortization tables are structured, it might not always be a good idea to refinance a mortgage. He asks us to explain this a bit more in detail, and of course, Joe and OG oblige. During the segment, we'll explain financing, interest rates, amortization tables, and more.We'll also carve out some time for some of Doug (who seems to be acting a little suspicious today... more on that later) and his trivia. Learn more about your ad choices. Visit podcastchoices.com/adchoices