The Stacking Benjamins Show

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!

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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….

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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....

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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.

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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!

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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!

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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!

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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.

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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!

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Think you can't network like a pro because you're an introvert? Better put your party hat on and take a shot of liquid courage, because our guest today is coming in with strategies and techniques that'll turn anyone into a lean, green, networking machine. (Without resorting to sending out hundreds of spam emails). Our guest, Matthew Pollard, has helped multiple businesses become million-dollar ideas, and he assures us it has a lot less to do with having the skills of a smooth talker, and a whole lot more with honest connection and preparation.

Having trouble with the law? While the long arm of the government may be able to seize your bitcoins, today's piece shows that by forgetting a key piece of information, you don't have to worry about your bitcoins ever really going goodbye - but good luck cashing anything in for your retirement. Plus, we'll cover why everyone's favorite mortgage strategy, velocity banking, is an off-the-rails fun way of paying down your debt... until it all comes crashing down around you.

Plus, during our Haven Life line, Justin tells us he's interested in buying stocks for his daughter. Her favorite game, Roblox, is about to go public, but the company is doing a direct listing. Justin asks: Are direct listings as bad as IPOs for everyday investors? Is there anything he should know about before getting involved? We'll give Justin the rundown, and even throw in a few of our favorite apps to get kids started on investing.

As always, we'll save some time for Doug's network-based trivia. Enjoy!

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