The Stacking Benjamins Show

Sick of working for "the man"? Today we'll talk to a woman who's never held down a single full time job but who's created a career out of what most people call "side hustles." We'll explore pitfalls, opportunities, and more with Shanah Bell, author of The Art of Being a Pita, Paula Pant from Afford Anything, and from our very own podcast, OG.Halfway through the show we'll take a break from our side hustle conversation so Joe can sit down with Tony Aquilar, the founder of new student loans app Chipper. Worried about your student loans? Tony will share some helpful tips on how to pay down student loans quicker, AND will show off how his app will help you do just that....and after we take some time for Doug's trivia, our roundtable contributors will share some ideas to help caller TJ during our Magnify Money segment. TJ wants to know some fun and interesting ways to teach kids about money and saving for retirement. Thoughts? Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wonder how an insurance company would look at some of your favorite movie and television series characters? We might be nerds (who are we kidding...we're huge nerds), but that's exactly the question we wanted to ask Haven Life's Brittney Burgett, who gives us some really enlightening answers. Not only do we find out information about how insurance companies view cartels, money laundering, and 1950's office spaces (all funny and not shocking), we also talk frankly about contestable periods, health ratings, professional considerations, and more. If you've ever wondered how insurance companies think about you, this is a fun way to start.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

PT Barnum was the king of over-the-top sales pitches...or was he? He certainly was the king of hustling to earn a living. If you're looking for a role model to help you work harder, sell better, or be more...entertaining, there are few people you should look to before the Greatest Showman himself. Today, biographer Robert Wilson joins us to dig into the early years of Barnum's life, from his time organizing lotteries and working on general stores to his first move to New York City. Barnum not only was a great pitchman, but he always wanted to back it up with shows that would make people tell their friends and come back. "There's a sucker born every minute" might not have been a slogan that Barnum lived by....we'll explain in the show.Plus, during our headlines segment, Joe will talk to Desiree Vargas Wrigley from Pearachute about just how much you're spending on family fun this summer. The amount is sadly a LOT higher than you may expect. We'll also cover one MarketWatch piece that is a good reminder for all of us: all that 401k and IRA money doesn't all belong to you. While the bottom line in your retirement account may look lofty, the tax bill could take a nice chunk of those savings away. We'll share why.After some P.T. Barnum inspired trivia from Doug, we'll throw out the Haven Life line to a caller who wants to know more about Token, the Fintech company we interviewed a few weeks ago. While Token provides security for the rest of your accounts, what happens if they're breached themselves?And in our letter's segment we'll tackle a question from Michael, who wants to sell some stock his godmother got for him while he was teenager and transfer the cash into a Roth IRA. What are the steps he needs to take to sell the stock? Does he need to hire a broker?Looking for something deeper than what we give you on the show? Three days a week not enough? Subscribe to our weekly newsletter: The Stacker. Learn more about your ad choices. Visit podcastchoices.com/adchoices

We're absolutely thrilled to bring you the best in 2019's personal finance indie podcasts, blogs, and video. Today we welcome Miranda Marquit from the Plutus Awards to walk through the 2019 Finalists for the Plutus Awards. The goal of these awards is to shine a light on a wider spectrum of names and brands so that we all have the ability to hear from a wide universe of points of view. Today we present that universe with our finalists picks in our 10th annual awards celebration. Good luck to all of the finalists!Thanks to MagnifyMoney.com for sponsoring Stacking Benjamins. 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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

The cast in the Broadway play "Rent" asks, "How do you measure the life of a man?" Today we ask that question as we speak with Nicholas Mann (a great musician in his own right) about his father, the founding member of the Julliard String Quartet (among many other accomplishments), Robert Mann. We'll be talking about Robert Mann's early years: growing up in Portland, getting started on the road to his dream, taking the plunge to move to New York City, his years at Julliard, his military service, and more. We'll talk about practice, mentors, money, teachers, lessons learned, and much more.In our headlines segment, are you the type of person to use the same password on every online account? First...stop that! There's plenty of easy-to-use software out there that will make multiple passwords a breeze. Second, you'll want to change your passwords on the double if you own a Robinhood account. We'll dive into the details during the show, but the company was storing their passwords in plain text, a HUGE internet security no-no. In our second headline, do you still have unpacked boxes from you last move? We'll look at an Inc. piece detailing how one NASA intern scored millions just by cleaning out an old box he'd carried around through the years. Maybe there's gold in that hoarding you've been doing.After a little dose of Doug's trivia, we'll throw out the Haven Life Line to Ryan, who's started his own business. Ryan is looking into opening a self directed IRA, but his friends have been pointing him towards a SEP 401k. What type of account should he choose?We'll end out the show with a letter from Leo, who wants to know how 529 plans affect FASFA eligibility. Wouldn't it be better to not invest in a 529 plan to make sure your kids get financial aid?Thanks to Clearbanc for supporting Stacking Benjamins. Are you doing over $10,000 a month in revenue? Find out how you can receive Clearbanc capital by getting your 20 minute term sheet at clearbanc.com/SB. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Bola Sokunbi tells us the amazing story growing up with a mother who was initially left out, like many women, of the family's financial decisions. Whether you're a man or woman, today you'll hear the reality of your financial life: you can't delegate it to other people. There's nobody better to tell this story, so we're super excited that today Bola, the mind behind Clever Girl Finance, joins us.In our headlines segment, we'll take a call from our long-time friend and Detroit Free Press reporter Susan Tompor. Susan has written a piece on a new money scam which involves receiving an email from your "boss" asking you to buy a few costly gift cards. This is definitely one to watch out for, and we'll find out all the details on the scam from Susan.And after we give Doug a chance to deliver some buffalo wing themed trivia, we'll throw out the Haven Life Line to a caller who's wondering what to do with her cash from a discontinued retirement plan. Brooke works for a small startup, and her employer recently discontinued a fee riddled 401k offering. Brooke had $2000 in her 401k, and wonders what should she do with the money now?We'll finish out the show with a letter from Brian, who wants to make sure his thinking on the pro-rata rule and backdoor Roth conversions is solid. Could he avoid the tax hit from a traditional-to-Roth conversion if he does it in in his wife's name? What's a backdoor Roth IRA? How does a pro-rata rule work and will it kill you? All good news: we'll explain the rules AND define all of these technical terms.Thanks to Clearbanc for supporting our show. If you’re doing over $10,000 a month in revenue, find out how you can receive Clearbanc capital by getting your 20 minute term sheet at clearbanc.com/SB. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Everyone has made mistakes during their life. Lord knows, we've made our share. While we thankfully forget about a lot of the smaller mistakes we make, the larger mistakes tend to stay with us as lessons we can use to help us in the future. Learning from your own mistakes is great, but being able to learn from another person's mistakes and saving yourself some heartache is even better. Today we're giving you a free "head directly to Go and collect $200" card by sharing with you some of the WORST investing decisions of all time, as shared by one publication.Halfway through the show, our roundtable discussion will take a break for our Fintech segment. With colleges opening up their doors for the fall semester soon, we'll focus on one company that's striving to improve student grades AND earn them some extra cash while doing it. Joe will sit down with Jerry Zheng from One Class, and get some detailed bullet points on just how the note-taking company works.Plus, we'll answer a voicemail from K during our Magnify Money segment. K wants to get into real estate and is looking for ways to save for a down payment. While lowering her contributions to her retirement accounts make the most sense to her the idea still makes her cringe. What if she never finds a buying opportunity and misses out on money she could have been earning? Thoughts?Looking for something deeper than what we give you on the show? Three days a week not enough? Subscribe to our weekly newsletter: The Stacker. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Being a good communicator is a crucial skill we don't pay enough attention to. It's easy for us money nerds financially-minded individuals to learn the intricacies between different financial plans, study market fluctuations, and keep up-to-date on the best interest rates, but why is it so hard to focus on soft skills? Chief among them is communication. That being said, we're money nerds at the end of the day. That's why today we're sitting down with Jason Hanson, a man who's had to communicate professionally day-in and day-out as a former CIA officer.And in our headlines segment, is Wells Fargo catching the last few years of turmoil? We'll discuss the reasons behind why the number of financial advisors saying "sayonara" to bank is finally leveling out, and the lessons you can learn when it's time to leave your job behind. Plus, in our second headline, what's the big reason behind the record number of CFOs retiring from their companies? What are they seeing on the horizon that the rest of us aren't?Later, after we hand the mics over so Doug can dish our some of his trivia, we'll answer a voicemail from an anonymous caller who says he's "new" to money. He's 34, isn't in debt, and has $300,000 in the bank. What should he do with the money? Learn more about your ad choices. Visit podcastchoices.com/adchoices

We have two exciting announcements that mom wanted us to share with you about today's show:One - We're answering your letters, including a BUNCH of them about the Roth IRA, named after a Congressman whose birthday happens to be this very date. In celebration, we're cracking open the mailbag with our friend Scott Rieckens from the Playing With Fire documentary. He stopped by the basement while here for a sold-out screening, and while he was here we put him to work because OG and Joe...well, you know.On the topic of letters...if you'd like to ask us a question, remember now to use the Haven Life line (StackingBenjamins.com/voicemail). We stopped accepting new letters months ago and we are just now seeing the light at the end of the tunnel on letters! Hurrah!Two - Mom wanted us to remind you to take off your shoes when you walk inside the house. She works hard to keep the rugs clean, and you'll just mess them up.That's all. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

With debt piling up, savings gone, and your credit cards maxed out, how do you pull yourself out of the hole and get on the right financial path? The first step, of course, is to stop digging, which is what one Reddit user did after racking up over $16,000 in credit card debt. They also posted a list of things they did to make their debt go bye-bye and their Benjamins start to pile up. While it may not be quick or easy to get yourself back to being debt-free, there are definite steps you can take to get yourself into the world of financial freedom - and we'll walk through one piece which reported on the Reddit forum, adding in experts and other information. How much of it is helpful and what isn't? Depends on what section of the piece we're talking about. Today, helping us dig in today is a crack team of internet stars. First, making her return trip to the basement is Chelsea Brennan (Smart Money Mamas), second, we'll welcome Len Penzo (LenPenzo.com), and then we'll say hello to the guy from our own podcast, OG.How would you like to earn stock rewards from companies where you already shop? While you shouldn't shop more to get rich (that won't end pretty), it would be nice to get some extra stock just for buying pillowcases, right? We thought so too, and that's why halfway through the show we'll take a little break from our discussion while Joe rings up and chats with founder David Nelsen from Bumped.Plus, after we subject entertain our roundtable with a round of Doug's trivia we'll break out the Magnifying Glass and answer a listener voicemail from Tyler. His 401k plan is expensive. How does he control his costs of investing for retirement? Learn more about your ad choices. Visit podcastchoices.com/adchoices