The Stacking Benjamins Show

Is your job going bye-bye? Today's guest says, "Probably." But how do you succeed in an economy that seems structured against you? On today's show, we're excited to have a deep conversation with the co-founder of NPR's Planet Money and the creator of the new Passion Economy podcast, Adam Davidson. We'll touch on what the future of technology means for you, for the economy, and how our current economic situation is "more of the same" or "different" than the country's last two big downturns... and how you can STILL do what you love in an economy that's constantly changing.

Plus, why in the world are people investing in bankruptcies? Is the Hertz stock fiasco ringing a bell? During our headlines we'll explain how the concept behind "knowing just enough to hurt yourself" caused amateur investors to lose their Benjamins.

Later we'll throw out the Haven Life Line to Dave, who has been laid off this year. Dave and his spouse were previously unable to contribute to a Roth, but they're now eligible. Dave is thinking they should convert their traditional IRA over to a Roth and he wants to know our thoughts. 

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As we round the 4th of July holiday, we've all celebrated George Washington as the first President of the United States, the general who lead the Continental Army against the British, and the second or third most popular character in the Broadway play "Hamilton." However, did you ever think of George Washington as an entrepreneur? Economist John Berlau has thought about that AND how Washington's entrepreneurship aspirations molded both his vision as a future leader, and our country. Today he's with us to share stories from Washington's life, including how he became an entrepreneur, and some of his most prominent contributions to our country. If you're a history fan, entrepreneur, or just someone who wants to learn how the best-and-brightest made their way, today's show is for you.

Of course, that's not all. We'll discuss the recent issues with the economy and your 401(k) plan. It turns out that you can still become a 401(k) millionaire. There's no need to get overly creative with your financial plan. That'll be good news for most of us. Plus, we'll talk estate planning. When someone chooses you to manage their affairs when they pass away, what should you do? For some of you we'll preview our best tips, and for everyone else, we'll share what you should think about when choosing an executor or contingent trustee. Don't know those terms? We'll even share what that means on today's show for no charge!

Of course, we also save time for Doug's fireworks, including his trivia AND incredible wit. It's a kick-butt first show back for the SB team, and we're glad you're hanging out with us.

Check out the show notes for ALL of the links in today's show!

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Should you have an exit strategy for the stock market? In this rewind episode Paula Pant and Len Penzo go head-to-head with their own personal strategies.

Also, during the Fintech segment we interviewed Kyle Robertson, co-creator of the now discontinued Lemon app. While you won't be getting your hands on Lemon, our discussion still serves as a great introduction to taking charge of your finances with the help of financial tools.

You can read the original show notes below:

It’s WAR in the basement today, as Len Penzo (LenPenzo.com) and Paula Pant (AffordAnything) square off about exit strategies. Should you think about selling if the market tanks but you haven’t yet reached your goal? We’ll talk about that for a LONG part of today’s super-sized show….but that’s not all. We also have other topics and the usual hilarity.

At the halfway point, in the FinTech spotlight we talk to Kyle Robertson, the co-creator of the Lemon app (Lemon.co), about how his expense and money tracking app works. Not only does it show you how you’re spending money, but it’ll provide helpful data and tips so you can manage your money better in the future.

Thanks to MagnifyMoney for sponsoring our podcast!

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There have been plenty of retirement headlines shared online lately. While many of these articles share some great grounding advice, we've also seen a fair share of "scare" headlines as well. With that in mind we hand-picked today's rewind episode to dispel retirement fears you may have picked up the last couple of months. You can read our original show notes below:

Retirement planning is all about starting early and planning well, which is why we’re excited author Emily Guy Birken (Choose Your Retirement) joins us in the basement to share her top 5 retirement myths.

That’s not all we do on this show, though. OG & Joe share headlines about “smart beta” and the ROI of a college education. We take your letters about life insurance and improving your credit score….and much more.

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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.

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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!

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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. 

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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.

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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!

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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. 

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