The Stacking Benjamins Show

Have you ever wondered how your life might be different if you'd decided to take that gap year instead of attending college? Or maybe you decided at the last minute to change the course of your life by talking to a stranger? Laura Schroff backtracked into an unlikely meeting with an 11-year-old boy who was panhandling on the streets of New York City in the late 1980s. After initially walking by th...

How's your summer going with the family? Had a money discussion yet? We know that it's hard. Talking about money can be awkward and difficult when trying to explain concepts to kids. We're helping out today by sharing tips and strategies for talking to kids about money. Our roundtable consists of Doc G, Pam Andrews, and our very own OG. They share their tips for talking about money with family and...

You think your credit score is a jumbled mess now? Luckily, the three major credit bureaus just stopped counting most medical debt into your score. But it used to be that credit was based on so much more (and less), because the credit "bureaus" were run by people who could be paid off or who could raise or lower your credit just because they liked you. Or they didn't. Dr. Josh Lauer joins us today...

We know how the war began. You may know many of the battles. Of course, you know how it ended because you're celebrating the end today if you live in the USA. But how was the war paid for? Today we dive into answering that question with historian Thomas Schachtman. He'll share stories about our founding fathers, their fortunes, and what was at stake if the revolution had gone differently, from bot...

Is this the worst possible time to retire (or to make ANY big financial move)? Inflation is SLIGHTLY up. The stock market is SLIGHTLY down. This could feel less like retirement and more like falling into a deep, dark chasm. Yet, our panel today is here to provide a flashlight and some safety equipment for your goals. Kyle Landis-Marinello joins us (author of Personal Finance and Investing), along...

Instead of focusing on what you're going to do today, how about deciding "what am I NOT going to do?" That's one of many pieces of productivity advice that Oliver Burkeman brings to the basement table today. He's studied productivity over his long career and has now written a new hit book on the topic. Oliver shares lessons from Four Thousand Weeks: Time Management For Mortals on today's show. In...

It's a popular refrain: evaluate your life to reduce time pressure and the resulting stress. But what if this approach wasn't as useful as you'd initially thought? We went from driving to a store to purchase closing to "one-click" ordering on Amazon to save time, but what did we lose in the process? Are we making poorer decisions because we're moving at the speed of light, all propelled by brands...

How much do you love your current job? Some studies show that more than half of people are unhappy with their job in some way. Finding your calling and a career you don't regret can be tough but our roundtable today will help you think about the right questions to ask yourself and tips to not regretting your career. We welcome Doc G from Earn & Invest, Len Penzo from len penzo dot com and Paul...

You've probably heard of having skin in the game, but what about having soul in the game? Having soul, in whatever game you choose, brings purpose and meaning to life. Our guest today learned about putting his soul into his work and finding true purpose from his parents. Vitaliy Katsenelson grew up in a small Russian town and saw the struggles and sacrifices his parents made to give him and his si...

Buffie Purselle is a tour-de-force. She started her own business at 19. She's been featured on not ONE but TWO reality television shows. She's helped hundreds of budding entrepreneurs begin businesses. So to celebrate Juneteenth we're helping empower YOU with the woman who believes that you have to "crawl before you ball." She'll share stories from her own upbringing and early jobs that you can le...

Did you know that when at a fine dining restaurant, you should never lift your menu from the table? ...or that you should sip your drink from the exact same spot on the glass each time? On top of that, definitely do NOT announce to the table that you're headed to the bathroom. What does any of this have to do with money? Besides the fact that if you're interviewing or networking at a restaurant an...

You start that amazing new job and the boss hands you a giant stack of paperwork. Does that sound familiar? One of those forms is most likely a crucial piece of your financial picture: your 401k enrollment. How much should you contribute? How do you choose investments? Today, Joe and OG share the top mistakes they see people make with their 401k, so you can learn from others' mistakes and avoid yo...

Remember the phrase 30-and-out? That was what people said when they'd sign up to work for the same company for their entire working lives. Since the days of single-job employment, working thirty years has become a standard idea. But why? Kiersten and Julien Saunders are the brains behind the new book Cashing Out, where they throw 30 years to the curb. Instead, they advocate focusing on 15 years. W...

Can you be idle and still get ahead in the game of life? In some cases, this is absolutely the best answer. Our contributors to today's roundtable discussion dive into their answers to the question, "Can doing nothing benefit you in life and with your money?" Our special guest today from Sensible Money is Certified Financial Planner Dana Anspach. Joining Dana are our regular contributors, Len Penz...

It only takes a moment watching the news to learn what David Gergen already knows: our current leaders have failed us. In some ways, it isn't their fault; growing up during the Vietnam conflict, many of our leaders grew up in a deeply partisan country and have led from that divisive position. However, Gergen, who served not one but FOUR US presidents...from both parties (Nixon, Ford, Reagan, and C...

Know those horrible situations where everyone's fighting at work -- or worse, at home? Talk about a horrible investment: being invested in a rotten environment can overshadow even the best portfolio returns. Good news, though. It turns out, there are two types of conflict: the kind that allows us to grow and produces a positive outcome and the kind that's downright toxic. To help us find a way tow...

It's time to get vulnerable and break down the barriers. As we always say, 'personal finance is personal' which makes money talk hard (and embarrassing) at times. Our roundtable is getting vulnerable about their money and career and sharing ways to talk about money with others. Jeff Underwood, Paula Pant, and Len Penzo join our roundtable to discuss a blog piece about being vulnerable with your mo...

What was your last interaction like with a flight attendant? The friendly skies weren't always as friendly to flight attendants as they are today. Actually, the term 'flight attendant' wasn't coined until stewardesses won a long battle against the airlines. To tell the fascinating story that has affected change on so many workplaces, Nell McShane Wulfhart joins us today. She talks about the strict...

Maybe you’ve had a nagging feeling that things just aren’t right. Your partner is either acting strange, or money is gone from accounts and you aren’t sure why. It’s time to get a better handle on your cash flow. So how can you make sure your money is protected during the worst of times and how can you also ensure your partner isn’t hiding money from you? Today we welcome Tracy Coenen, a forensic...

One of the top reasons couples argue is because of money. We always say that personal finance is personal and it's true that every person and couple have different views on money but coming together as a couple to share those goals is key. But even before most couples combine their finances, they have a wedding to stress about. Our roundtable today talks about couples and money and they dive into...

A million and one money decisions in a day...how the hell do you make the right one???? Between social media and the internet, f--- me, there are countless tips and "advice" from strangers on how to manage your money, but absolutely ZERO are really tailored to you. In the basement, we know that information can be powerful if used correctly, and that's exactly why we invited Jean Chatzky and Kathry...

Gearing up for summer travel? Not only is summer fun about saving money; it's also about ensuring that the dollars you spend are worth it. What theme parks are actually worth your money? Today we help you kick off your summer because Robert Niles from Theme Park Insider joins us for his 8th annual survey of what's new/what's hot/what's undervalued in vacation travel. He shares the newest rides and...

Are you in the career you love? If not, what's stopping you from making a change to that job you've been dreaming of? Changing careers (especially if that means becoming an entrepreneur) isn't always as easy as it sounds, which is why our rockstar roundtable panel today is ready to help you find your way. Entrepreneurial coach Sylvia Moe Inks, Paula Pant, and Len Penzo discuss pivoting your career...

"Failure is an option," Carter Malloy says during today's interview, and it's true. Evolution in business is critical, and technology, the right team, and pure persistence can pull a success from near-certain failure. From early websites to failed business plans, business owners have many challenges to navigate. Carter Malloy faced tons of these challenges and more while advocating for an investme...

Sell, sell, sell! Buy, buy, buy! No, panic trading is not the answer when the market dips, but the news certainly can makes it sound like the end of the world. So what should you do during a down market? It turns out there's money-saving magic in avoiding selling everything to cash. Today, Joe and OG share their top 5 things to do during a market downturn. They talk about rebalancing, turning off...