The Stacking Benjamins Show Westwood One

You've saved and invested diligently for years and you're now sitting on a fat stack of Benjamins. When's the right time to say f*** it and start spending cash like there's no tomorrow? Today our contributors share their big spender to saver money stories and give their thoughts on retiring WAY early... on less than a million dollars. It's not always about the bottom dollar, but also lost potential income (and raises) if you need to return to work years down the road, lost marketability as your skills age, and outdated professional networks as your co-workers move on to other opportunities.
Joining us on the roundtable this week is Diania Merriam, founder of the FIRE-Movement inspired EconoME Conference, Len Penzo from the LenPenzo.com blog, and OG from our own podcast.
Friday Fintech: Health and Wellness Expert Angelo Poli from MetPro.co
After our contributors finish swapping money stories, Joe sits down with health and wellness expert Angelo Poli from MetPro.co. With summer right around the corner, we polled our Stacker community for all the health and exercise questions they've been dying to get answered. From questions on aging metabolisms to intermittent fasting, and of course, time-efficient (and free) workouts even the busiest Stackers can do at home... Angelo covers it all and then some.
Listener Voicemail: HSA Horror Stories?
Our anonymous caller, who we refer to as Sal, calls in with some HSA questions. For years he was told he only needed the Explanation of Benefits form (think something like a medical statement) before finding out he actually needed his receipts as well. While this was an easy fix, Sal asks: what other blind spots could he have? What HSA horror stories should he know about - and avoid?
As always, Doug has some post-Fintech airtime to deliver his game-show trivia.
Enjoy!
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How do you make money driving for ride sharing companies? Credit card hacking? Churning bank accounts? How do you help your family plan? What's it like to meet with financial advisors? Today members of our community, Alan, Claudia, and Jon are kind enough to share their wisdom and experiences in all of these areas! Plus, we'll also share an important headline about doing your homework before investing, another on helping your community, and more.
Of course, we'll also throw out the Haven Life line to a caller with a great question about estate planning. That comes after Doug's trivia and a few of your emails.
Enjoy! 
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How much of this stuff goes over your head? What are the absolute first things you need to know about when you're rolling out on your own? Today high school personal finance teacher and author Jake Cousineau joins us to dive into the very first items you should include on your list of lessons to learn about money as you begin your journey. From the double-edged sword of interest to simple banking and ideas on budgeting and saving, we'll share some of Jake's favorite tips so that you can leave today's show more prepared than you were before you listened.
Annuities Changing Standards: Our Headlines
States are rolling out some new rules around annuity sales, which largely are meant to mimic the SEC's Reg BI (best interest). While industry spokespeople say it's a step in the right directions, consumer advocates say it isn't enough. Today we'll share how annuities work, where the problems are in the industry, and how these new state-by-state rules may change the game (or not).
We'll also share our TikTok creator video minute, and today we'll share a refreshing story. An online "guru" actually apologizes for leading his followers into a scam. While we love the sentiment, who would have known (hear the sarcasm coming?) that a StarWars universe-themed crypto coin called Mando might be fake.
We'll also share the latest worldwide real estate news. Inflated prices aren't just happening in your back yard. Around the world we're seeing some eye-popping numbers. What's the takeaway? We'll talk real estate today!
Of course, we'll also throw out the Haven Life line AND save time for Doug's trivia. It's another great day in the basement!
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Are you coasting or actually planning your next move? Living in the land of "I should" or "I might" versus "I'm where I want to be right now?" Whether it's balancing your happiness with your career choices, changing industries, family planning, or deciding how long you want to work until retirement - lifestyle choices encompasses all of our financial decisions. Today we ask our contributors: what's the design for your lifestyle? What drives your motivations, career choices, retirement plans, and financial decisions? It's a great discussion with plenty of overlap with financial independence, and one you can use for a diagnostic in your own life once you hear how it's done.
Welcome to a live-making of the Stacking Benjamins show! Recorded during Podbean's Finance Podcast Week, we had the opportunity to showcase a behind-the-scenes making of the podcast in front of a live audience, and it was lots of fun that you'll hear today. Our round table has a big discussion on lifestyle design this week using their cell phones. For this one, excuse our worse-than-usual audio. We promise the engaging conversation will be worth it.
Our Listener Mail: What (Non-Financial) Podcasts Do We Like?
We finish our live show with a letter from Lou: he's heard us talk plenty about our favorite TV shows and movies, but what about our favorite non-money related podcast? Our contributors deliver: from podcasts like Whatever Happened to Pizza at McDonald'‪s‬ and Betty in the Sky with a Suitcase‪!‬, to This Week in Virolog‪y‬ and more, you'll hear plenty of our favorite podcasts we love to binge when we're not thinking about money. (Except for one contributor who always is thinking about money - but we'll leave that one a surprise).
Of course, we couldn't possibly do a live show without giving up some airtime for Doug's trivia.
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Don't think you can overthink your money decisions? Study's show that sadly, you're wrong. Not only will overthinking cause you to create overly complex plans, but you'll give up early on strategies, fail to move when you need decisive action, and exhaust yourself with going over the options "just one more time." Overthinking rarely involves positive thoughts, and you can't win when you're not confident. Today we'll help you solve that issue. Long time listeners will remember the last time we had Jon Acuff on the show back in 2017, (find that here: Give Yourself The Gift of “Finished”).
In Jon's new book Soundtracks, he explores how our thought process and the stories we tell ourselves impacts our everyday lives, AND how you change your own soundtrack to solve your problems with overthinking.
Give Enough Cash and Even The Spenders Pay Up... Eventually
Remember the news the weeks after the first stimulus checks hit? Everyone waiting for the first piece of evidence to release their blog posts and podcast episodes about how everyone ran out and bought fancy 4k's and PS5s? (We totally didn't do that...not us!)
Well, a new study shows that given ample cash to clear out the Amazon wish list, many people HAVE ended up paying off their bills. During our headlines Joe and OG discuss paying down debt, the double penalty of being stuck in a debt cycle, and how you can walk away from the I Can't mindset.
How The Pandemic Changed Our Retirement Worries
The pandemic challenged a lot of the conventional thinking behind emergency funds, healthcare, and and retirement living. A newly released Fidelity report queried investor retirement worries, and while there were some surprises, other figures proved that not all financial thinking needs to be redrawn from the ground up.
Doc G from the Earn & Invest podcast joins us today to discuss what the report means for the broader retirement conversation AND what the numbers mean to you.
The Haven Life Line: What's the deal with Fundrise?
Sean is interested in investing with Fundrise, and wants to know our thoughts. While the company has seemed to change up their marketing since they first came on our radar we still have some reservations, and OG and I actually differ on a few thoughts here.
Never familiar with REITs? We'll explain your options on the show, but you can get started here: Traded vs. Non-Traded REITs: Which Is Best for You?
Enjoy!
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This seems like an easy decision, doesn't it? Skimp on the party and invest money in your dream residence. Yet, don't we always say to invest in experiences because they appreciate in your mind (becoming more epic as the years pass), instead of things that clutter our lives? Co-hosts of the new Netflix reality show Marriage or Mortgage, wedding planner Sarah Miller and real estate pro Nichole Holmes, join us for a fun discussion on a dilemma many newlyweds face: how much cash do you spend on making your dream wedding a reality, and at what cost to your future home?
We know, this is a financial podcast, and financial nerds are definitely biased on this one, but Sarah raises some pretty good points, and you just might surprise yourself when you're nodding along. We're not saying you should go for broke on a huge wedding (though if you do, please invite us), but Sarah's reasoning isn't exactly in contrast with our own money philosophy.
Making "Fun Money" on trading apps? Watch out for the tax bill.
In our headlines segment, we'll relive the horror story one Robinhood trader experienced when he found he had an $800,000 tax bill. Worse news? He could have avoided it fairly easily if he knew one rule that we'll share on today's show.
Tiktok of the Week: Amazon beats Walmart because of... adult toys?
In our TikTok minute you'll find that it isn't just young, aggressive traders (or at least TikTok talkers) who are making bizarre statements about financial success. So are television anchors.
Want early retirement? Try buying a school bus!
How great is this? One man in his twenties decided to cut out 40 years of saving and instead retire right now. We'll share his story and what it means for you.
BUT that's not all. Of course, we'll throw out the Haven Life line to a lucky listener AND we'll dovetail in some of Doug's amazing trivia.
Enjoy!
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