The Stacking Benjamins Show

How many times have you lost and thought, "I'm going to learn to do better the next time, so I win." What did you learn specifically from losing? Author Mary Pilon asked the same question and put together an anthology on stories about epic losses that shines a spotlight on the struggle involved trying to reach the top of anything. If you're inspired--like we are--by stories of other's struggle so we don't feel so alone, you're going to be super excited listening to Mary share a few epic stories from the book.

Next, has Robinhood finally attracted its share of regulator attention? During our headlines, we'll recap the numerous reasons why you shouldn't use Robinhood for your investing. Plus, in our second piece, are you heading to retirement disaster by underestimating your life expectancy?

During the Haven Life Line, we'll take a question about short-term investing from Matt. He's currently in college, and looking to invest $2000 for a couple of year. Where's the best Matt can invest his money?

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Welcome to the happiest podcast on earth? Do you know where we stole that catchphrase from? If you do, you just might be a product of marketing. Companies spend millions of dollars each year trying to get you to remember their brand. Today we'll prove just how much we remember marketing with a game show episode where we slightly change the brand slogans and see if our roundtable participants (OG, Paula and Len) can come up with them. How many can you get right? ...and is that a good thing?

Plus, halfway through the show, insurance company Hippo and home security firm Simplisafe join us to talk about a new study talking about home insecurity. With the pandemic, the average person feels less secure about their home life. As a response, they've also teamed up with a new partnership. We'll share details about the study and the partnership on today's show.

Enjoy!

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What happened to the sharing economy? The new work model promised to give workers flexibility and new income streams, while people with excess could share what they had with people looking for help. What it turned into is a different matter: lots of people earning below minimum wage, an over-saturation of workers all competing for the same prime hours, and headline-making lawsuits from companies looking to minimize their responsibility to workers. These are all things new gig workers can expect when joining the new "gig" field. Today we chat with Juliet Schor, author of the new best-selling book, After The Gig. During our interview Juliet will share the business strategies that kick-started the shift in direction large gig and sharing companies made, how gig workers don't know how much they're truly making, and we'll also dive into possible solutions to the gig economy's current problems.

In our headlines segment, we'll ask, "Why half of the millennial generation have canceled their travel credit cards?" Plus, Fidelity is now offering their first Bitcoin fund. Should you pay any attention?

We'll finish out the show with our Haven Life Line. Retired clergyman Bill calls in asking if he can really take out a tax-free housing disbursement from his 403b if the money was made through clergy work. 

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Ever wish you had better habits? Whether you're not getting out of bed for that morning run, or you stay up too late before an important meeting in the morning, or you can't stop breaking the budget - we've all asked ourselves, "why did I do that AGAIN?" Dr. Joseph Cardillo, best-selling author of multiple books on the intersection of mindfulness and health not only knows the answer to that, he's sharing the solution on today's show! In his new book, 12 Rules of Attention, Dr. Cardillo goes through easy-to-follow steps on how you can stop bad habits in their tracks, AND how to trick your brain into establishing habits that'll make you a superstar in whatever area of your life you wish to improve.

Brittany Spears is back in the news. In our headlines segment we'll review how her father has served as her conservator for twelve years (taking care of Spears' money), and now the pop star wants him out. So, what does it mean to have a conservator? How can someone make sure everything is on the up-and-up? We'll share that and recall one famous conservator horror story which saw one extremely rich widow fight homelessness. Plus, what's a headlines segment without talking about money and video games? Today we'll also cover the beef between Apple and Epic Games. It's...wait for it...pretty....epic.

We'll also throw out the Haven Life line today to listener Swaggenit, who was notified by Turbotax that because he already contributes to his 401k, he won't receive any tax benefit for his IRA. He asks: because he doesn't receive a tax advantage now and he's contributing post-tax money, will the money be tax-free when he withdraws it? Is there a good reason to keep contributing to his IRA?

As always, we'll of course save some time for Doug's trivia, who's keeping his Independence Day questions going strong. Enjoy!  

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The one and only Scott Alan Turner from Financial Rockstar podcast joins the fun this week. He, Len Penzo and Joe tackle financial insecurity, mortgages and horrible Valentine's gifts.

Also, we're ending our Rewind week with some pretty special segments. Check out our original show notes below:

At the halfway point we have a great visit with Thomas Smyth from AskTrim.com about his new app. Trim dives into your accounts to find forgotten subscriptions you're paying and unsubscribes you (if you wish).

AS IF that's not enough, we're excited at the end of the episode to share some time with the star of SoFi's new Super Bowl commercial, Brandon Williams. We'll talk about the experience and his investing passion - real estate.

That’s it for this week of rewinds! Coming Monday: We’ll chat with Dr. Joseph Cardillo, author of 12 Rules of Attention: How to Avoid Screw-ups, Free Up Headspace, Do More and Be More at Work.

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What does your financial dream house look like? Financial planner Greg Powell says that he always has trouble convincing people to complete a financial plan because it sounds like a ton of work. But a financial dream house? That’s a much easier sell, and he’s going to help you sell yourself on that concept in today’s episode. We’ll talk about where investments fit into the overall structure (not as far up the priority list as you’d think), how to work through building your “plans,” and then how to build a team that effectively helps you finally create the “structure” of the house.

Happy Hump Day! We're keeping our rewind week going strong with today's show featuring our time with Greg Powell. We thought his unique approach to financial planning was interesting then, and we think it's interesting now. Also from our original show notes:

On the Haven Life line, Garrett asks about company stock inside of his 401k. Should he dump it? If you have company stock inside of YOUR 401k, this’ll be helpful for you…and if you own LOTS of one company’s stock, you’ll also like this segment. We also answer a letter from Andrew, who wonders about his target date fund. As you know (if you’ve listened to us before), we’ve been pretty critical of target date funds. What is his next best move? Do YOU have a target date fund? Maybe today’s letter segment will help you, too!

Of course we have Doug’s trivia, some bad jokes, and lots more….

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Most of us have been at home a lot more than normal, which led us to realize that this week may be high time for a discussion about "stuff." Too many of us have too much clutter. Clutter not just in our house, but in our minds, in our thoughts, and in our goals. That's why today's episode is super important to us.

Happy rewind week! While Joe and OG are hanging up at the beach sipping mojitos (okay, maybe not really), I’m turning back the clock to visit some of our favorite past interviews. We're kicking this week off strong with one of our favorite interviews in the catalogue: Vicki Robin, author of bestselling book, Your Money or Your Life. You can read our original show notes below:

Why are you saving money? How much joy are you receiving from that “stuff” you own? You may rethink your financial plan after today’s show, because our guest is the co-author of the HUGE bestselling book, Your Money or Your Life. Vicki Robin helped shape the financial independence/retire early movement, and she’s on her way down to the basement today to talk to us about re-examining your beliefs around your life and your money. Your money or your life, indeed.

In our headlines segment we’ll talk about student loans with Robert Farrington from The College Investor. He’ll talk about how over 3,000 people just took part in an event to pay off a TON of student loan debt. We’ll share best practices, how best to apply to lower interest rates on your debt, and how to pay them down in a way that makes sense for your situation. We’ll also discuss the new SEC proposed fiduciary rule. Is THIS finally the rule we’ve been looking for? Will it replace the mostly knocked-down rule from the Department of Labor? We’ll review the rule and discuss what you need to know about it on today’s show. Plus, we throw out the Haven Life line to Karen, who’s contributing to a brand spankin’ new health savings account. How should she best use it? We’ll share how these plans work on today’s show. We’ll also answer another listener letter, throw out Doug’s trivia question, and watch him try to juggle….one ball.

Thanks to MagnifyMoney.com for sponsoring Stacking Benjamins as well. MagnifyMoney.com saves users on average $450 when they compare, ditch, switch and save on credit cards, student loan refinancing, checking, savings and more. Check out MagnifyMoney.com for your savings.

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Big houses, fast cars, and flashy boats... are we all destined to hit the "what do I really want with life anyway" crisis? While everyone's therapy comes in different forms, does it have to mean burning obscene amounts of cash budgeted for things like, "life savings" just to reclaim your life? On today's show we'll share what YOU can do when you're second guessing your goals and your life's direction...so that you can keep the sportscar money in your pocket. Helping us out on the roundtable today is Kathe Kline, from the Rock Your Retirement podcast, Paula Pant from Afford Anything, and OG. Plus, we're helped today by our special celebrity reader: Tom Schwab, founder and CEO of Interview Valet. We're happy to have him reading our focus piece today!

Curious about what your friends and other influential people you follow are investing in? After our discussion on making sure your mid-life crisis doesn't turn into a disaster, we'll ring up Katie Perry, VP of social investing platform Public.

We'll round out the show with a question from Martin, who's interested in house hacking. Martin is 17 doesn't have much cash to throw around. He asks: what can he do to have his cash work for him? So far he's been reading up on stocks in the Motley Fool, but what else could he be doing?

And of course with it being Friday... we'll make some time for Doug's game show. 

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What does it take to work as a Hollywood designer for major rock and roll bands? Lindsay Hearts started with a sewing machine at age 16, worked her way up to fashion week in New York, and finally decided it was time to make a move to reach her dream: creating a brand of her own in LA. She moved west with the goal of NOT working for someone else, but to build her own business. Today we'll hear her inspiring story, plus how she's helped out during the time of COVID, how she manages a team, and much more.

While interest rates remain near all-time lows, the cost to actually refinance just got more expensive. We'll share that during our headlines segment, and also dive into the "fun" happening at Eastman Kodak. What does that have to do with your money? Maybe more than you think.

Of course, we'll still throw out the Haven Life line AND we'll also share some of Doug's amazing trivia. Enjoy!

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Charles Duhigg is a guy who knows a lot about habits. His book on the topic was on the New York Times bestseller list forever, his second book is also a bestseller, and now he has a new podcast called "How To!" that talks about the habits needed to perform specific tasks. Want to be funnier? Lose weight? Get a promotion? He covers it. Today we cover HIM and the topic of habits on today's episode!

Also today we ask the question, "How much skill is involved when a day trader wins?" Apparently, according to a recent piece, the statistics ain't good (as mom says). We'll cover that in our headlines segment, plus what Amazon plans to do with the huge stores left behind by Sears and JCPenny. Of course, they have plans...

We'll also throw out the Haven Life line to Brock, who writes in with a dilemma on student loans. He's running low on funds to pay for college, but he has about $3,500 invested in the stock market. Should Brock take out subsidized loans, or cash in some of his investments? We'll share our answer with you AND him, AND save time for some of Doug's delicious trivia. Enjoy!

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