You've seen the ads. Invest like the ultra-wealthy. Get access to what the 1% does. But what does the 1% actually do -- and how much of it should a normal person try to copy? Joe, OG, comedian and finance educator Roxanne Duckels, and Jesse Cramer run every popular "rich people investing" idea through a simple filter: steal it, scale it, or skip it. The answers will surprise you -- especially the one where OG wants to delete an entire asset class from existence.

What You'll Walk Away With

• Why long-term thinking is the one habit the 1% has that every Stacker should steal immediately -- and the short-term execution piece most people miss when they try
• The tax strategy obsession that the wealthy genuinely use -- and why Jesse ranks it seventh on his list of financial priorities, not first
• What paying for advice actually means when you're smart enough to do it yourself -- and why the wealthiest people surround themselves with even smarter people anyway
• The alternative investment marketing trap hiding inside every "invest like the rich" pitch -- and OG's case for why most people have no business touching any of it
• Why the accredited investor designation protects almost no one -- and what the real risk is when you lock up money in illiquid investments chasing slightly better returns
• The leverage conversation that exposes a contradiction hiding in plain sight for every real estate investor
• Why Roxanne's path to financial independence started with filling her gas tank all the way up -- and what that tells you about long-term thinking at any income level
• The one question that should precede any alternative investment conversation: does the expected return actually beat what publicly traded equities already offer?
• What the trivia competition scoreboard looks like heading into the back half of the year -- and whether OG's historic lead is as safe as it looks
• Why rich habits and "what the 1% does" are two completely different things -- and which one is actually worth chasing

Why This Matters Now

In a noisy market environment, the "invest like the wealthy" pitch gets louder every time volatility spikes. Private credit, non-traded REITs, leveraged real estate, alternative assets -- the marketing machine never stops. For Stackers in their 40s who've built something real and don't want to blow it chasing a category that mostly benefits the people selling it, this episode is a useful reset. The habits worth stealing from the 1% turn out to be remarkably unglamorous.

From the Basement

Joe, OG, Roxanne Duckels from Finance Rox, and Jesse Cramer run the "invest like the rich" playbook through a steal-it-scale-it-skip-it framework -- and nobody agrees on everything, which is exactly what makes it useful. Doug arrives with Mayday trivia about the origin of the distress call and the year it was coined, which turns into one of the cleaner trivia finishes of the season. Whether the basement scoreboard moved in OG's favor or Jesse closed the gap is a question best answered with your earbuds in.

Resources Mentioned

• Finance Rox -- Roxanne Duckels on YouTube and Instagram @FinanceROX
• Personal Finance for Long-Term Investors -- Jesse Cramer's podcast, wherever you listen
• Stacking Benjamins Newsletter (The 201) -- recent issue: brokerage vs. UTMA/UGMA vs. Trump accounts for kids; stackingbenjamins.com/201
• Stacking Benjamins Vault -- stackingbenjamins.com/vault
• Stacking Benjamins Community -- stackingbenjamins.com/basement
• Stacking Benjamins Meetups -- stackingbenjamins.com/bad

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Haley Sacks didn't grow up knowing what a 401k was. She was nannying for a kid named Winthrop on the Upper East Side, doing comedy at night, and getting paid cash under the table. Then she sat in an HR meeting and her eyes glazed over -- and she decided that was the last time she'd be caught unprepared with her own money. Today she's Mrs. Dow Jones, with millions of followers and a new book. The basement finally got her in the chair, and she did not hold back.

What You'll Walk Away With

• The "future rich person" framework -- what separates people quietly building wealth from everyone else performing it
• Why the biggest wealth trap isn't overspending -- it's the psychological pull of looking rich before you are
• How automation is the real secret behind Haley's path to millionaire status -- and why willpower alone was never going to get her there
• The action movie analogy that finally makes the debt-versus-investing debate make sense -- and which one you tackle first
• Why your fixed expenses might be the actual problem -- and the two levers you can pull when the math doesn't work
• The "money date" habit that keeps Haley on track -- and how to make it something you'll actually do every month
• What a mise en place approach to your finances looks like -- and the four accounts every future rich person needs in place before anything else
• Why cutting spending has a floor but earning more doesn't -- and how to think creatively about your income ceiling
• The mortgage volatility conversation hiding in this episode -- including OG's take on where rates actually belong historically and why "date the rate" might be the most useful three words in real estate right now
• Why comparison is derailing more financial plans than bad investments ever could

Why This Matters Now

If you're in your 40s and you still feel like the millionaire milestone belongs to someone else's story -- someone who started earlier, earned more, or just had better instincts -- this episode is a direct challenge to that belief. Hailey Sacks didn't have better instincts. She had a glazed-over HR meeting and a determination not to be caught unprepared twice. The foundation she built after that moment is exactly what she walks through today.

From the Basement

Mrs. Dow Jones herself -- Haley Sacks -- finally makes it down the stairs and does not disappoint. Joe and OG close the episode with a Wall Street Journal headline on mortgage rate volatility and what it actually means for anyone trying to buy, move, or refinance right now. OG lands what may be the cleanest take of the season: when should you borrow money? When you need to borrow money. Doug arrives with Dow Jones trivia about the longest-tenured company in the index, which turns out to have been added in 1932 and is hiding in plain sight on every household shelf. Whether the basement scoreboard had anything to do with Procter & Gamble is a question best answered with your earbuds in.

Resources Mentioned

• Future Rich Person by Haley Sacks (Mrs. Dow Jones) -- pre-order with $700 in bonuses at mrsdowjones.com/book; releases May 12th
• Mrs. Dow Jones on Instagram and YouTube -- @MrsDowJones
• Mrs. Dow Jones podcast -- Financial Therapy
• Wall Street Journal mortgage volatility article by Veronica Dagher and Ben Eisen -- linked at stackingbenjamins.com
• Stacking Benjamins Vault -- stackingbenjamins.com/vault
• Stacking Benjamins Meetups -- stackingbenjamins.com/bad
• Stacking Benjamins Community -- stackingbenjamins.com/basement

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Retirement expert Jamie Hopkins has spent 20 years helping people plan for retirement, and his most counterintuitive advice stops most savers cold: in the final years before you retire, putting more money away might actually be hurting you. This week he joins Joe and OG to explain why, and what to do instead.

In this episode:

Why financially prepared retirees still end up miserable, how to practice spending before you retire, the home bias that quietly tanks your portfolio and your quality of life at the same time, and what to actually do with all that home equity when the time comes.

Biggest takeaways:

The last three to five years of extra contributions barely move the needle on your retirement portfolio. Working six months longer matters more. So does learning to spend. Take that money and actually use it, so you're not hitting retirement having never practiced.

Retirement isn't a math problem, it's an identity problem. The people who struggle most aren't broke. They never figured out where their purpose and community would come from once work disappeared.

Over half of Americans are forced into retirement earlier than expected. You need a plan for that scenario now, not when it happens.

Resources mentioned:

• Jamie Hopkins' Retirement Sketchbook wherever books are sold
• The Stacking Benjamins scorecard: stackingbenjamins.com/scorecard
• The Vault: stackingbenjamins.com/vault

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What happens when you stop playing it safe and start playing it smart? In this episode, Joe Saul-Sehy, OG, and Neighbor Doug sit down with David Gardner, co-founder of The Motley Fool, to explore how breaking traditional investing “rules” can sometimes lead to the biggest wins. From his early career to building a community of investors who think differently, David shares the lessons that shaped his approach and why focusing on long-term investing (with a dash of joy) is the key to building wealth.

This isn’t just theory—David opens up about the real-world evolution of financial advice, the importance of conscious capitalism, and why advisors need to shift from just picking stocks to becoming true guides in an era where investment products are commodities. Along the way, the basement crew mixes in a few unexpected detours (yes, including some movie talk), reminding us that money doesn’t have to be boring to be meaningful.

If you’ve ever felt like the “safe” path with your money was leading you in circles, this episode offers a fresh perspective from one of the most influential voices in modern investing. Get ready to rethink the rules, laugh along the way, and come away with strategies to make your portfolio—and your life—more rewarding.

• Why breaking conventional investing “rules” can sometimes be your best move

• The evolution of The Motley Fool and its impact on everyday investors

• How long-term thinking beats short-term noise in building wealth

• The role of conscious capitalism and why businesses matter beyond profits

• Why financial advisors need to pivot their focus to guidance, not just products

• How criticism shaped David Gardner’s career and what he learned from it

  
  

  Points to Ponder During the Episode

• When’s the last time you broke a “money rule,” and did it pay off—or backfire?

• Do you believe financial advisors should focus more on guidance than investment selection?

• What’s one company or stock you’ve stuck with long-term—and why?

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What's your financial plan? Is it built on bedrock or are you "winging it", aka building on sand? On today's show, Certified Financial Planner Brian Ursu joins us to dive into four strategies that will help anyone trying to build their financial house. For veteran planners, these will be things you've heard before. However, the question isn't, "Have you heard them?" Like anything, you should ask yourself, "Am I doing them?" THAT may yield a completely different answer.

Plus, TurboTax maker Intuit has been in the news recently, because they're buying credit score site Credit Karma. What does that mean for consumers like us? Also, because Credit Karma is a FinTech company, what does that mean for FinTech? We'll ask Ryan Falvey from Financial Venture Studio both of those questions. If you've heard Ryan before on our show, you know he'll have an interesting point of view.

Of course, that's not all. We'll throw out the Haven Life line to a lucky listener AND still leave time for Doug's trivia...which today takes a more-than-usual unusual twist. 

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If you believe telling a white lie is okay, do you believe that about money topics? What about white lies that are told by big-time bloggers or (gasp) podcasters about the path to riches? We'll dive into the world of lies and deceit on today's show with an all-star cast around the rickety card table. Joining us today we welcome Dustin Heiner from The Master Passive Income Podcast, Paula Pant from the Afford Anything Podcast, and from our very own podcast, OG!

We know a lot of you use calculators for your job, but we think you will all like using the Retirement Budget Calculator after hours as well. During our Friday FinTech segment, Joe will talk with Jason Parker from the Sound Retirement Planning podcast. They'll discuss how Jason's Retirement Budget Calculator has continued to grow. Joe last year said that this calculator was the "best retirement calculator for consumers" (he still thinks there are better calculators for pros). We'll have all the details on how it works AND share some discounts you won't get if you buy the calculator elsewhere.

And finally, during our MagnifyMoney segment we will answer a question via Twitter. What is your best advice for future college students to fund their education when their parents can't or won't help them? There's SO much more...but you'll have to listen to hear it all! Hope you can join the fun.

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It's your big moment. You're talking to the boss or giving a presentation at work. Maybe you're finally in front of your dream customer. And you blow it. Today we'll help you earn more money by focusing (well, as much as we focus...) on speaking well. Whether you're trying to convince the family to wash dishes or your boss to give you a raise, speaking more effectively is far from a "soft" skill. So today we welcome Grant Baldwin, author of The Successful Speaker, and host of the Speaker Lab podcast to give us some tips and tricks!

How does Social Security look? During our headline segment, we'll dive into that topic, and run through the future of Social Security. How long will stay solvent? And, in the most important question anyone has asked around here today, we'll ask, "How did a couple of guys score free McDonald's?" Just another day on our show.

If you think that's all, it might be your first time here (so welcome!). Of course, we'll throw out the Haven Life line to a lucky caller, share some of Doug's amazing trivia AND much, much more. Enjoy!

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Do you have trouble staying in charge of your money? Maybe you let your priorities get away from you and want to make a change? Today we'll talk about communication, being direct, and asking for what you really want with the author of the hit new book Bow Down, Lindsay Goldwert. In this unique new perspective on how to take charge, Lindsay sat down with dominatrixes across America to get first-hand information on how you can "reset the power dynamic in any situation to get what you want—whether it’s from a husband, boss, or partner."

During our headlines segment, are you finally bringing in a HUGE nice income, but your bank account isn't rising? Lifestyle inflation can become a serious issue for high earners, and without a proper plan in place investors run the risk of becoming a HENRY - High Earner, Not Rich Yet. Plus, during our second headline, we'll touch on why actor Rick Moranis is making a return to the big screen and what lessons you can glean for your financial plan.

Plus, we'll open up the mailbag during our Haven Life Line and answer an estate-related question from Diana. Diana is the executrix of an estate plan for the funds of two pre-teens but wants to appoint someone else to take over most of the responsibilities. What can she do? What is she supposed to do? We'll cover some estate planning basics on today's show.

And, of course, we'll also make some time for Doug's trivia. Enjoy!

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There's been a lot of market fears going around this past week, but regardless of its origin people have been asking the same question for years: what should we do when the bull market finally ends? We're finishing out the rewind week with one of our classic old-school roundtable episodes featuring Paula Pant, Len Penzo, and Greg McFarlane answering that very question. You can read the original show notes below:

This has been a LONG bull market. So if you know that the next eight years will most probably NOT be like the previous eight, do you swap out some of your investments? We ask our roundtable panel that on today's show and as always, find Greg, Len and Paula all have different answers than you probably expected.

We also tackle lifestyle paradigms. Are you paying too much attention to your neighbor's success? Finally, we'll discuss fake news....no, we aren't going politics. We'll ask our panel whether there's any "fake news" in the money area that they're sick of hearing. Of course, they come through with some great examples.

In our Freshbooks FinTech segment we talk to SelfLender CEO James Garvey about building credit. How does SelfLender help people find financial footing? They have an interesting idea and an exciting approach. Can't wait for you to hear all about it.

Thanks to SoFi and MagnifyMoney.com for sponsoring our show!

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Are you committed to saving, but can't seem to get other people around you on board? It can be frustrating once investing for the future has clicked in your head, but not for the people you care about. Gene Natali, co-author of The Missing Semester, shared some great information with us on how to get anyone interested in saving for the future and we're revisiting that interview today. You can read our original show notes below:

You're excited about saving, but how do you get someone else to take the plunge? Today's guest, Gene Natali, says that the answer might not be what you expect, and he should know. He co-authored the book The Missing Semester about personal financial education in the classroom, and he's BACK on the Stacking Benjamins show to share how to get ANYONE started in the right direction with their money.

In our headlines segment, we talk about financial advisory fees. Are they going down? A recent report has details on where that ship is headed. Also, we'll talk about the age-old active vs. passive management debate. Do active managers hold a candle to passive? Does it matter? Then we throw out the Haven Life line to Dan, who asks about EE bonds. Are these bonds a great way to protect against deflation? We'll also answer a letter from Todd, who has some extra money and wants to know how to invest it...other than in sending it to his favorite podcasters (#disappointing). 

It's National Martini Day, so Doug's pouring drinks down in the basement and we're all invited over. Come join us!

Special thanks to  M1Finance for sponsoring our show! We couldn't do any of this without the support of some pretty awesome companies.

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Have you ever thought about jumping into real estate? It isn't all roses, rainbows and money. On today's rewind episode, the FinTern takes us back to 2018 and Dana Bull's appearance in the basement, talking about all of the good times and bad in the business of investing in property. 

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What big money wasters exist in your life? Unless you're like us, Benjamins seem to slip out of your pockets WAY too easily. Today, we'll test our guests' game show skills to see if they can guess 16 fantastic examples of money wasters we found hidden in a recent Marketwatch piece. Joining us to play along we welcome Chelsea Brennan from The Smart Money Mamas Podcast, Doc. G from the What's Up Next show, and our very own nerdy engineer, Len Penzo, from Len Penzo dot com!

One big money waster could be the exorbitant bank fees people pay. During our Friday FinTech segment, Joe will talk with one company trying to lower your fees. Nami Baral, Chief Empathy Officer from Harvest joins us. They'll discuss how Harvest uses AI to help you save on all sorts of bank and credit card fees. We'll have all the details

And finally, during our MagnifyMoney segment we will answer a question on if our fellow Stacker should open a non-profit farm. There's SO much more...but you'll have to listen to hear it all! Hope you can join the fun.

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Are you struggling with debt? How about a little inspiration? Cindy Zuniga paid off a LOT of debt in just four years. Like you, she finally realized she'd had enough and something had to change...so change she did. Today she'll share the struggle and her path out from deep debt, along with dispelling some myths about debt payoff strategies along the way. She'll also share how she successfully used a cool concept called "zero-based budgeting" to not just pay down debt but to curb her spending habits successfully. Additionally, she'll share some of the places she found inspiration to keep going on her long journey during her payoff process and after. If you saw Cindy's story on Good Morning America, you'll love this expanded interview with her today on Stacking Benjamins!

Plus, Fidelity Investments has some great news for savers: we're doing a good job saving collectively. However, some of us are (ahem) doing better than others. John Boroff, Fidelity's Director of Retirement and College Leadership joins us Joe's dad's shortwave radio to talk about not just the successes, but also why people have maybe been more successful so you can emulate those strengths. He'll also share some great ideas to save more if you're behind.

If you think that's all, it might be your first time here (so welcome!). Of course we'll throw out the Haven Life line to a lucky caller, share some of Doug's chocolatey trivia AND much, much more. Enjoy!

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When was the last time you planned to make some of your big dreams a reality? What's holding you back? Time? Money? Fear of the unknown? Today we're talking to Tamara Jacobi, who created a retreat in the Mexican jungle right after college. She's the author of the new book Wildpreneur AND a continental traveler, who'll join us and talk about how you can face your fears, climb to new heights, and make your dreams a reality.

Are you worried about the economic effects of the coronavirus spreading to your portfolio? During our headlines segment, we'll ring up Chris Cook, president of Beacon Capital Management, and get some answers on what you can do to inoculate your investment strategy.

During our Haven Life Line we're shaking things up a bit. We're keep the voicemails on hold this time around while we turn our eyes toward the results of our Instagram poll: what's been this year's most surprising budget busters? We'll break down our range of answers during this special Haven Life segment.

As always, we'll carve out a bit of time for Doug's trivia.

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What really derails retirement dreams? Spoiler alert: it’s not always the stock market or your 401(k). Sometimes it’s sneaky habits—like leaning too hard on your house as a retirement plan or ignoring how long you might actually live—that quietly gnaw away at your financial future. In this episode, Joe Saul-Sehy, OG, and Neighbor Doug dig into the most common middle-class retirement killers and how you can sidestep them.

But this isn’t your average checklist of “don’t do that.” The team dissects questionable advice floating around internet forums, debates stock splits and diversification, and even finds time to unravel why owning a cat might make you a magnet for gangster-level problems. Add in Doug’s trivia about a famous singer’s real name, and you’ve got an episode that’s equal parts practical and delightfully unpredictable.

Whether you’re worried about stretching your retirement savings or just looking for sharper ways to think about financial advice, this episode offers both reassurance and reality checks. So grab your favorite mug (or maybe your cat), settle into your seat, and get ready to learn how to protect your retirement from the biggest threats—while laughing at the absurdity along the way.

What You’ll Learn in This Episode:

• The habits that quietly sabotage retirement plans (and what to do instead)

• Why your house may not be the slam-dunk retirement strategy you think it is

• The risks of living longer than you expect—and how to plan for it

• How to sniff out sketchy financial “tips” before they lead you astray

• The surprising traps behind stock splits, diversification myths, and overconfidence

• Why even well-meaning advice can backfire if you don’t look at the big picture

Questions to Ponder (or Debate in the Basement Facebook Group):

• Which retirement habit do you think trips people up the most—and why?

• If you had to choose, would you rather rely on your house equity or a diversified portfolio to fund retirement?

• What’s the worst financial “tip” you’ve ever heard online (or maybe even followed)?

FULL SHOW NOTES: https://stackingbenjamins.com/habits-that-destroy-middle-class-retirement-dreams-1736

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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Buying running shoes for your partner who you know loves to run, you find THAT romantic? Taking a walk in the park holding hands, is that still romantic? Watching TV or a Movie and not saying a word to each other during the entire show, you find THAT romantic? Today we'll turn romance on its head as we apply the question "Is that romantic," to a BUNCH of financial questions. Do romance and money mix? We'll find out. Here to help us spread some love on Valentine's Day from the Afford Anything podcast, we'll say hello to the lovable Paula Pant and the guy with the dry sense of humor from this very podcast...OG!

How old will you be when you die? Will you have enough money? It turns out, many of us will live for a long, long time, according to science. What if you run out of money late in life? Worse yet, what if a family member runs out of money and you have to sacrifice your retirement to take care of them. Today, during our FinTech segment, we'll share details about a company working on that very issue. Blair Baldwin joins Joe in the basement to talk about AgeUp.

And finally, during our MagnifyMoney segment, we will answer a question on HSA accounts and the military. Is our caller eligible for an HSA?

As always, of course, we'll quiz our contributors with an epic gameshow question regarding the number of people who really do celebrate Valentine's Day! It's a circus as usual on today's Stacking Benjamins Show!

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Why are some of the coolest financial tools rarely used? For example, people by-and-large avoid HSA accounts, when they're the Swiss-army knife of a healthcare plan. Today we'll shine a light on another type of plan that's not often used: the Roth 401K. A recent piece in a major publication predicted that Roth 401K plans will become bigger now that the SECURE Act has been enacted. What do Joe & OG think? Do THEY like the Roth 401K? You'll find out during today's episode!

After that, we're all about your letters! You've been kind enough to ask us lots of questions, and Joe & OG today grab the mailbag and sort through it. We'll tackle everything from buying a home to investing in a Roth IRA to whether Monopoly is a good game or a great game. We didn't say that they were good questions....we just said there were lots.

But that's not all. We'll also throw out the Haven Life line to a lucky caller AND we'll hear some great trivia from Doug about one of our greatest Presidents...Abe Lincoln. Enjoy!

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Don't look now but Friday is Valentine's Day! You're probably wondering what a "chocolates and roses" holiday has to do with finances... and the answer is...A lot. As we'll find out today, many people don't hesitate about turning their wallets over and shaking out ALL their cash. But today we'll help you celebrate in style (or in jest) WITHOUT breaking the bank. Today we've invited Sara Skirboll from ReatilMeNot to share with us plenty of great advice on how to find great Valentine's day dining deals WITHOUT using your whole stack of Benjamins.

Plus, how much do you hate love reading through dense paperwork and contract terms? It's safe to assume you probably hate paperwork as much as we do, which is why covering some good news from Fidelity: they're cutting out 20% of the information that clients must review before opening an account. And in our second headline, we'll share the latest from a lawsuit between Shannon Dougherty and State Farm. It's ugly and just got...uglier.

During our Haven Life Line call, we're going old-school and tearing open a letter from our new BFF Diane. She's looking for some alternatives to HSAs and long-term care plans. What options are available for people who can't use the more traditional options?

Of course, we'll save some time for Doug's trivia.

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Would $250,000 a year be enough for you to "get by"? It wasn't for one early retiree. Today we're going to dive into income, expenses, priorities and bucket lists. Helping us today is a roundtable team of fantastic personalities. First, our special guest today comes from Revele Financial Group, Dawn Dahlby! From the Afford Anything podcast, we have Paula Pant, and Len Penzo joins in the fun from Len Penzo dot com!

What is the most expensive piece of artwork you own? Do you think you could ever own a Andy Warhol piece or a Monet? Well today, during our FinTech segment we'll share a company helping people do just that. Joe'll talk buying fractional shares of art with Scott Lynn, the founder of Masterworks.io. We'll discuss not only the types of art that newbies mistakenly buy, but also, liquidity, the long term returns of art, and more.

And finally, during our MagnifyMoney segment, we'll answer a question on whether you should take risks while you are still in debt?

As always, of course, we'll quiz our contributors with an epic game show question about The Beatles! How much did they receive for performing on the Ed Sullivan Show?

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JT and Tamzon had a great start. After paternity leave from a fantastic job, JT thought he knew that with his burgeoning side-gig, he could quit his job and live happily ever after without going back to full-time work. Then, he found out that the math wasn't working. What would you do? We'll share one family's story of taking control of your goals and then rebooting when the math still doesn't make sense. On today's show early-retirees JT and Tamzon join us to talk about adding flexibility into your planning.

Plus, are you a Medicare recipient? If so, it's an important open enrollment time for many. If not, you should plan ahead for the (ahem) increasing cost of healthcare. Danielle Kunkle Roberts from Boomer Benefits joins us to chat about all things Medicare. And in our second headline, we'll share how much your peers have saved for retirement. Want to gauge how you're doing? We'll have all the numbers.

Of course, we're also going to toss out the Haven Life Line and we'll still make room for Doug's trivia. Step aside, people! There's a new episode coming!

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Much of the game around managing money is in doing the little things...not being tripped up by the small mistakes and doing those little things that can turn failure into success in a hurry. Today, Norm Champ (formerly of the Securities and Exchange Commission), joins us to talk about mastering your money. What are some of the moves you can make to be a better money manager? We'll talk about controlling expenses (with some ideas to help you hone your budget), automating your money, and more on today's show.

Plus, where does the money come from that most Americans use during retirement? The ugly answer we'll share during our headlines segment. Plus, we'll discuss lessons learned from the terrible event that dominated the headlines last week: Kobe Bryant's tragic helicopter accident.

Later we'll throw out the Haven Life Line to Julie, who asks about a fund many investors "in the know" talk about often. What's the difference between "VTSAX" and the rest of the less-often suggested crowd of funds that do the same thing? ...and of course, we'll save some time for Doug's trivia.

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So, how much money do you make? Could a borrow a big sum of cash? Ever had any of THOSE moments? What do you do? Well today we'll discuss some seriously awkward questions. To help us, we welcome from Afford Anything the amazing Paula Pant, the almost retired Len Penzo from Len Penzo dot com, and from this podcast the straight shooter OG!

If you or anyone you know is in the job market, watch out! Recruiters are now corresponding more and more via text. What could go wrong with that? We'll dive into how to apply some ettiquette to your text messages with Suzanne Lucas, AKA the Evil HR Lady. At the halfway mark of today's episode, we'll hear from the Evil HR Lady about the correct way to communicate via text to recruiters and future employers.

And finally, during our MagnifyMoney segment we will answer a question from Facebook Group on a few tax questions on who to have prepare your taxes?

As always, of course we'll quiz our contributors with an epic gameshow question about the world record for longest roller coaster marathon ride! Hope you can join the fun!

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She'll tell you over and over that her job isn't interesting. But if you're a money nerd, do we have a treat for you today, because accountant Tracy Coenen spends her time chasing down bad guys using spreadsheets and bank statements (I'll stop if you need a moment). Today she'll tell us stories of two stories where she helped catch perpetrators by using financial records (and some amazing ingenuity) to help bring "bad guys" to bear.

Plus, are you interviewing soon? Even if you aren't we'll talk about some useful tips if you're interested in moving up the ladder at work or with another pursuit (and who isn't?). Plus, we'll discuss the new milestone one fund company just passed and pause for a moment...man, that's a lot of money.

Of course, we're also going to toss out the Haven Life Line to Dillon and get Joe and OG's take on how Dillon should approach his investments. All and and we'll still make room for Doug's trivia. Step aside, people! There's a new episode coming.....this plate is HOT!

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How did America get its start? Of course, by relying on the financial fortunes of a few of our founding fathers. Today we're rolling back the clock to look at how some founding fortunes helped launch our country. We'll dive into the topic with Tom Shachtman, the author behind the Founding Fortunes, to discuss the roll of money in uniting revolutionaries, both rich and poor.

Plus, should we be paying more attention to sustainability while investing? During our headlines we'll cover one report from Barron's that shows mutual funds ranking high on sustainability are actually outperforming the market. I know! We were surprised, too.

And finally, we'll answer a question from Heather during our Haven Life line call, who just opened up a Fidelity account. Heather and her husband want to start investing, but aren't sure which funds to put money into. Thoughts?

And of course, we'll save some time for Doug's trivia.

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If the FIRE movement is so inspirational, why is it constantly under attack? More heat was lobbed at the early retirement movement last week by a couple of industry insiders on Twitter. To help us, we welcome the FIRE-y woman behind the Fiery Millennials blog, Gwen Merz, Len Penzo from Len Penzo dot com, and the wonderful Doc G from the What's Up Next podcast! These intelligent, retirement-focused people will be discussing the tweet that started quite the firestorm.

If you or anyone you know has student loans, you'll want to listen to our Friday FinTech guest, Michael Block. He's the CEO and Founder of Pillar which is an app to help you pay back your student loans and save money. Early users have reported some huge wins, so we had to get the details from Michael about how it works.

And finally, during our MagnifyMoney call in segment we will answer a question from an anonymous woman on how she will be affected by inheriting a ROTH IRA.

As always, we'll quiz our contributors with an epic game show question about National Beer Can Appreciation Day from our neighbor, Doug. We'll have all that and more on today's show! We hope you can join the fun!

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If having more money guaranteed happiness, we’d all just set our financial targets, cash the checks, and live joyfully ever after. But as Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Joel Larsgaard (How to Money) unpack in this lively roundtable, life’s richest rewards often have little to do with your net worth. They explore why some wealthy people still feel miserable, how Benjamin Franklin’s approach to living can still teach us a thing or two, and why optimism may be your secret investing edge.

From the science that says peak life satisfaction might just happen around age 70, to the underrated role of good friends in a rich life (financially and emotionally), this episode blends timeless wisdom with modern money smarts. Whether you’re chasing financial independence, already there, or just trying to make sure your journey is as fulfilling as your destination, you’ll find ideas you can put into practice right now.

And because this is the basement, expect the conversation to meander into relatable stories, some eyebrow-raising trivia, and a few debates on what balance really looks like when you factor in both spreadsheets and smiles.

What You’ll Learn in This Episode:

• Why money alone won’t guarantee happiness (and what really does)

• How Benjamin Franklin’s life principles still apply in today’s financial world

• The connection between optimism and long-term investing success

• The surprising age when happiness may peak (and what to do before you get there)

• How to balance financial independence with enjoying the present

• Why strong social circles are a must-have part of your wealth plan

Questions to Ponder (and maybe share your answers with the Basement Facebook Group!):

• Do you think your happiness will peak at a certain age—or is it more about circumstances?

• How do you balance saving for the future with enjoying your money today?

• What’s one small, intentional change you’ve made that had a big impact on your happiness?

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Let's get back to the basics. Everyone talks about retirement tools, projections, timelines, and tax strategies...what about answering, "How do I begin?" If that's you, we've got you covered on today's show because we're talking to CPA Michele Cagan about Retirement 101. We'll start off with how you fare against other savers (or non-savers), and then discuss how you should frame retirement. Is it one long process? Should you begin with picking investments? We'll cover all of that and more on today's show.

Student loan borrowers everywhere cheered recently when a Navy vet had his loans discharged in court (something people said couldn't be done). In our headline segment we'll talk to attorney Leslie Tayne about how that happened, and maybe spill a little bad news (spoiler) about you and your student loans. But don't worry--all hope isn't lost. Leslie will also share some good advice for student loan borrowers.

Of course, that's not all. We'll also throw out the Haven Life line to a lucky listener AND save time for some of Doug's cat vs. dog trivia. It's another fun day down in the basement. Hope you can join us!

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Is debt crushing your dreams? Are your relationships affected by students loans or credit card problems? You NEED to hear today's guest, Reshawn Lee, talk about her situation. Reshawn and her husband Rob had horrible credit card debt, student loans, and couldn't ever seem to begin saving...until they took some drastic actions and everything turned out (spoiler!) not just great, but with a trip around the world! Today we'll talk about the work they do on their Learn Hustle Grow blog and YouTube channel, and learn about how they overcame their issues and began their path to financial independence.

Are you hearing (like we are) the buzzword "AI" all over the financial arena lately? We'll discuss one headline about how much of the artificial intelligence out there is more artificial than intelligent.

Later we'll throw out the Haven Life Line to Christina, who can no longer contribute to an employee sponsored retirement plan after a job change. How should she continue saving for retirement? Of course we'll also share some of Doug's trivia AND much, much more.

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Happy Birthday to our namesake Benjamin Franklin!! Today we'll celebrate by talking about one of our favorite topics, leaving your 9-5 job early. To help us, we welcome the woman behind the new EconoMe Conference, Diania Merriam, Len Penzo from Len Penzo dot com, and the wonderful OG from our very own podcast! This piece, written by Jessica Garbarino for her Every Single Dollar blog, is titled Why I Walked Away from a Six-Figure Job, and goes over some very good reasons to leave a "good" job AND many of the strategies she used to ensure she wouldn't have to return. (Big thanks to Mindy Jensen from BiggerPockets Money for reading it today as well!)

Frustrated with your money management skills? Don't feel like you have enough of a handle on your monthly expenses? At the halfway mark of today's episode, we'll hear from Belinda Rosenblum and Joe, as they unveil the exciting new course offered by the Stacking Benjamins team, Making Money Easy. We'll walk through all of the details today. It's been a long time since we've had a Stacking Benjamins course, so we're thrilled to tell you about it today.

And finally, during our MagnifyMoney segment we will answer a question from Reddit.com on whether or not a man is in the wrong for not wanting "free" childcare from his mother-in-law. Where do you stand? Is he on the right side of this argument?

As always, of course we'll quiz our contributors with an epic gameshow question about Ben Franklin from our neighbor, Doug. We'll have all that and more on today's show! Hope you can join the fun!

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Your retirement options just became more robust. A new law called The SECURE Act passed late last year and today we're sharing ALL of the information you need to know to change your plan to take advantage of this new, exciting legislation. If this is new to you, don't worry, we've got you covered. We'll begin the show with Joe & OG bringing you up to speed on the details. But if you're wondering how to use it well, we have something even better. Joining us on today's show we'll have Aimee Kwain from Fidelity Investments, Dan Keady from TIAA, and the Retirement Answer Man himself, Roger Whitney to walk us through their thoughts about the new law. Our goal today is to help you to understand how the SECURE Act impacts you, and we're excited about all you're about to learn.

Of course, this is a Stacking Benjamins episode, so that isn't all....later we'll throw out the Haven Life Line to Leo, who is wondering what he should do with his money while he's saving up for a downpayment on a house. Should he invest, or keep the money safe in a high-yield savings account?

Hoping for more? We've gotcha covererd. We'll also save some time for Doug's amazing weight loss trivia.

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Are you frustrated that your average day doesn't start out chasing your goals but instead reacting to everything else going on? Between kids, spouse or friends, and co-workers, how are you supposed to get ahead on YOUR agenda? Good news, today we chat with Romi Neustadt, the bestselling author of You Can Have It All...just not at the same damned time! We'll have an amazing conversation focusing on how to REALLY set goals that stick (hint: you don't start with goal setting), how to keep your priorities in line, and the key to focus like a laser on the things that are most important if you want to get everything possible out of life.

Plus, during our headlines, we'll examine some financial horror stories that very well could happen to you. Have you had some big changes in your life and haven't gotten around to updating your beneficiaries? While this may seem like something you can wait on, we're fairly certain today's ugly stories of people who put it off will make you jump on it sooner rather than later. Then, in our second piece, we're taking a broader view on "rules of thumb." Everyone considers the 10,000 steps a day mantra as a hard fact, but experts say there's a better goal you should have in mind. Being the savvy people we are (no eye-rolls please), we'll make some parallels to when people go wrong with financial rules of thumb.

During our Have Life Line segment we'll answer a question from Richard, who can't get happy hour off his mind. With plenty of birthdays he feels obligated to attend in the next couple of months, how should Richard balance out budgeting and social obligations?

And of course, we'll always save some time for Doug's trivia.

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What money moves are you planning for 2019? From creating an emergency fund and increasing your 401k contributions, to downsizing and starting a side hustle, there are plenty of smart financial steps you can take to make this year your best one yet. Joining our roundtable discussion about your best money moves today, we welcome Paula Pant from Afford Anything and OG from our very own podcast.

Halfway through the roundtable we'll take a break for our Friday Fintech segment and talk to David Chang from Gradifi. Gradifi is setting out to give employers an easy system to help employees pay down student loans and fund 529 plans.

We'll also answer a MagnifyMoney.com question from Zach, who's interested in the FIRE movement. Should he be following the advice of the FIRE movement and forgo his Roth account in favor of using a traditional?

And of course, we'll still have time for Doug's trivia.

Thanks to Skillshare for sponsoring the show. Start your two months of unlimited access to Skillshare by visiting SkillShare.com/SB.

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For many of us, "charity begins at home" is our constant refrain. But you have to admit, it feels good to give and to be a part of a community. Not only are you helping those around you, but you're also working together with your family or friends on a higher purpose. That's why we're thrilled today to talk with our friends, Scott Maderer from Inspired Stewardship, our good friend Paula Pant from the Afford Anything podcast, and the wonderful OG from our very own podcast about how they give! We'll share a piece from Marriage, Kids, and Money's Andy Hill about how he teaches his kids to give and get LOTS of great ideas from the team.

Plus, at the halfway mark of today's episode we'll hear from Saul Cohen from Round during our Friday FinTech segment. Round helps investors find exclusive investment opportunities so they can invest actively like the 1%. How does it work? Saul will walk us through Round's mission and how they work with investors.

And during our Magnify Money call we'll hear from our good friend Mollie, who wonders about gifts to nephews and nieces. How does she solve the giving problem?

As always, of course we'll quiz our contributors with an epic gameshow question by our neighbor, Doug. All that and more on today's show! Hope you can join the fun!

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What goals do you want to achieve? It's easier to reach any destination with the right people around you. To help YOU find your best route toward your goals, today we welcome Tim Rhode, author of Tribe of Millionaires, and founder of nonprofit 1 Life Fully Lived, to talk about building your network to reach your ultimate potential.

Plus, during our headlines, we'll cover a piece from Bloomberg about how credit card debt has hit an 10-year high, and what that means to you. Spend too much money this last year? Maybe it's time to go back and listen to Monday's debt cleanse episode.... PLUS, how about fees that drive you crazy? We'll highlight a BIZARRE fee that a hotel in West Virginia charged. So random...

Later we'll throw out the Haven Life Line to Anthony, who calls in to give the those of us in the basement some helpful advice about TSPs (Thrift Savings Plans) that you may have been unaware of. Thanks, Anthony!

Of course, we'll save some time for Doug's possum-heavy trivia.

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Wake up January 1 with a hangover? Even if you didn't "over-imbibe" on alcohol, there's another hangover people suffer from: excess spending. Let's make January a reset month if you overspent last year. As many financial gurus say, "Tomorrow is a new day" and you can decide that you want to grab the reins and control not just your debt but your money in general. Today we sit down with Brian Karimzad, CEO of Magnify Money, on all of the things you can do to make your debt cleanse a success.

During our headlines portion of the show, we'll take a look at how the average 401k fared in 2019. Good, bad... great? If you didn't do well with your retirement plan last year, how do you make a change to improve in 2020? We'll share some ideas. Plus, during our second piece, we'll examine the reason popular financial company Vanguard just eliminated even MORE trading fees.

That's not all, though! We'll throw out the Haven Life Line as well, and answer a voicemail from James who asks for investment advice. What do we think about James choosing top funds from different sectors to invest in? Is it a good strategy? Also, when he leaves the USA, what does he do with his retirement funds?

And of course, we'll always save some time for Doug's trivia.

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Where is the market going to go in 2020? Who will win the election? What did we learn from the Magic 8 Ball predictions of 2019? We'll start by looking at ALL of our last year's predictions and discuss LOTS of financial planning themes. Between emerging markets, individual stocks, playing the lottery, and more, we'll cover a wide range of money topics that you (gasp) might learn from. Calling in today to help out is our good friend, Paula Pant from the Afford Anything podcast, plus Len Penzo from LenPenzo.com...and OG from our very own podcast!

We'll take a break halfway through this monster podcast episode to talk to Ryan Falvey from Financial Venture Studio. What does the future hold for FinTech? Ryan has a front row seat for some of the hot new ideas coming out of this sector and will share some of the important themes you'll see coming to your phone, your computer, and your portfolio in the future.

As always, we'll also help a listener Magnify their Money...but today we're joined by special guest Brian Karimzad. Because Carter has a question that's specific to MagnifyMoney, it's fantastic that Brian dropped by just in time to help us answer!

It's a great, two-hour episode of Stacking Benjamins. Hope you can join the fun!

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What can you learn about leadership from someone who’s served four U.S. Presidents, navigated some of the most intense moments in American politics, and still believes the future depends on building more leaders, not fewer? In this Greatest Hits Week replay, Joe Saul-Sehy, OG, and Neighbor Doug welcome David Gergen—former White House advisor, Harvard professor, and author—to the basement for a masterclass on leadership that applies as much to your career and investments as it does to running a country.

Gergen pulls back the curtain on life inside the White House, from the early lessons he learned in the Navy to the behind-the-scenes moments that revealed the human side of Presidents. Along the way, he shares what separates great leaders from the rest, how to evaluate leadership in others (and yourself), and why service and responsibility are the cornerstones of lasting influence. Whether you’re leading a team at work, managing your family’s financial future, or just trying to be the kind of person others trust, you’ll find plenty here to sharpen your approach.

And because no visit to the basement is complete without some SB-style surprises, you’ll also hear stories of presidential humor gone sideways, a White House prank or two, and reflections on how good leadership isn’t about perfection—it’s about purpose. Plus, the guys tackle a listener question on investing without specific goals, and Doug tests the panel’s trivia chops with a leadership twist.

What You’ll Learn in This Episode:

• How David Gergen defines real leadership (and how it’s changed over time)

• The telltale signs you’re working with—or for—a great leader

• Lessons from the Navy, the West Wing, and history’s most memorable leaders

• Why building leaders is just as important as being one

• Practical ways to evaluate leadership in politics, business, and investing

• How a clear sense of service can make you a better investor and decision-maker

Questions for you while you listen (share with our Facebook group!):

• Who’s the best leader you’ve ever worked for, and what made them stand out?

• How do you evaluate whether someone is worth following—whether in politics, business, or life?

• What’s one leadership skill you wish more people would develop?

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While everyone else fights over whether this year or next is the beginning of a new decade, we'll help you focus your attention on the REAL issue: how awesome you'll plan to be in 2020 and beyond. Bestselling author and TED speaker Neil Pasricha joins us today to tell us stories about his amazing mother's search for awesome, his own lessons from past failures, and best of all, the history of the ellipses. They're hopefully the inspiration you'll need to kick off the Roaring 20's with a bang.

What are your New Year's Resolutions? We'll share some that were recently featured in a top publication during our first headline, plus some ideas from our team about how you can make them actionable (the most important part of any plan).

Of course we'll save time to throw out the Haven Life Line AND save some time for Doug's incredible Roaring 20's trivia.

We all hope you're as excited about a great New Year as we are here in the basement! Mom sends her love!

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We're ending 2019 with a fantastic look back at our interview with James Clear, author of Atomic Habits. One of the best thing you can do for yourself this next decade is building great habits and STICKING to them. Whether it's in your career, finances, relationships, or otherwise personal life, you'll find that developing great habits will be the best present you can give yourself moving forward.

It's been a blast this past week, we hope you enjoyed it as much as we did. Happy New Year!

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Jill Schlesinger gave us her top money lessons at the end of 2018, and we still think they're pretty great lessons to keep in mind a year later.

We'll start the episode with a special open, and then dive into our show with Jill.

Enjoy!

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Jean Chatzky gave us some fantastic lessons that we should've learned in 2017. Those financial lessons are still applicable two years later. We'll give the show a special open featuring Joe and OG, and then take a listen to our show with Jean.

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Back in 2016 we sat down with NYT Bestselling author David Bach to ask, "What should we have learned in 2016?" He had some great answers that still apply here at the end of 2019. Enjoy!

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CBS Business Analyst and host of the wildly popular Jill On Money Show, Jill Schlesinger joins us in the basement to recap 2015. What should we have learned? She'll have five lessons from events of the past twelve months.

Joe & OG share headlines and take your letters, including one asking about "too big to fail" and another asking about multi-level marketing schemes. Should our listener take a "free" plan from an MLM company rep?

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Welcome to day 2 of our look back at the lessons we've learned from the past decade. This year we took a special look at credit and family finances, take a look at our original show description below:

There are TONS of takeaways from 2014, and Rod Griffin from Experian joins us in the basement to tackle his top five that had to do with your credit and family finances. You'll be surprised how easily Rod takes current events and shows you what impact they have on your financial picture.

Fidelity may be creating their own robo-advisory arm? Joe & OG share that headline plus others. PK gives some of the BEST advice you've heard during 2014 during his segment. Doug gives the gift of trivia, and much, much more.

Thank you to MagnifyMoney.com for sponsoring our podcast.

Have a careful and safe New Year everyone! Thanks for being part of the SB family in 2014!

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With the end of the decade quickly approaching, we decided to mix things up a bit. Leading up to our first brand new show of the year on January 1st, we'll be releasing each of our special "what should we have learned" episodes. It's not only a look at how our financial focus has changed since 2013, but also how much our show has changed!

You can read the original show notes below:

Top advisor Scott Tiras (Barrons top 100 independent advisor list) joins us with five lessons we should have learned from 2013. What are some ideas we can glean to avoid mistakes next year? 

PK goes contrarian in this episode. Doug sneaks downstairs to borrow mustard. Len, Paula and Greg ask the magic 8 ball important questions about 2014....and much more.

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We've got the best linens out and mom's favorite table settings because Liz Weston is FINALLY headed down to the basement today to help us put a cap on all of the lessons we should have been learning this year. We'll say a HUGE welcome to our last Monday show of the year, as we wrap up another year of podcasting. We'd like to thank you for joining us in what we consider our biggest year yet. We've made some big changes to how we put this show together, and we'll continue to do so as we continue to grow and improve, which is only possible because of your continued support. We recognize that we live in a fast-paced world with a thousand distractions, so we remain humbled that you CHOOSE to listen to us time and time again. Thank you.

On today's show, we're taking a look back at 2019 to ask the big question: what should we have learned this year? While there is timeless investment advice, each year also brings some unique lessons for the future. Sitting down with us today to distill the big financial lessons of 2019 is Liz Weston, award-winning personal finance columnist and certified financial planner.

During our headlines we'll talk to Harlan Landes from the Plutus Foundation about what's going on in financial literacy. December is prime giving-season, and Harlan has plenty of advice on what you can do to support financial literacy in your own local area. During our second piece, we'll tackle one financial planning quandary: why in the world is it so difficult to follow your own rules for asset allocation? When a piece of your portfolio becomes overweight, it makes sense to sell it... right? On the other hand, why would you sell a "winner"? We'll talk about emotions and investing during our second headline.

Of course, we'll save some time for Doug's trivia too! Enjoy!

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What have you learned from the past 10 years? We'll do a deeper dive on today's show with our roundtable gang...who (not surprisingly) have some takeaways from the last ten years that we can all learn from. On today's show we welcome special guest Doc G from the What's Up Next podcast, Paula Pant from the Afford Anything podcast, plus from Len Penzo from LenPenzo.com!

Plus, at the halfway mark of today's episode we'll talk about a FinTech company who's figured out a more cost-effective and quicker way to put non-traditional investments in your self-directed IRA or solo 401(k) plan. We'll all get an introduction to Rocket Dollar, as we talk with Dan Kryzanowski from the company in today's Friday FinTech segment.

And during our Magnify Money call we'll hear from our new friend Tyler who wonders how to maximize his savings.

As always, of course we'll quiz our contributors with an epic gameshow finale question by our neighbor, Doug. All that and more on today's show! Hope you can join the fun!

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Not all financial advisors are created equal—and some will steer you straight into the rocks while smiling the whole way. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug share the top five warning signs your advisor may not have your best interests at heart. From shady investment recommendations to fee structures that deserve a magnifying glass, we unpack the behaviors and practices that can quietly drain your portfolio.

This isn’t just about avoiding bad actors—it’s about knowing what great advice looks like so you can spot the difference. You’ll hear why “fun money” accounts can be a trap, how to sniff out overly speculative pitches, and why transparency isn’t optional when it comes to your financial future. Along the way, we sprinkle in a few stories, historical nuggets, and plenty of those classic “Doug moments” that make a trip to the basement worth your time.

If you’ve ever wondered whether your financial guide is truly on your side—or if you just want to sharpen your radar—this episode will give you the practical tools to tell the difference between a trusted partner and a wolf in a well-tailored suit.

What You’ll Learn in This Episode

• The five biggest advisor red flags that should send you running

• How to evaluate an advisor’s investment recommendations for risk and suitability

• Why fee transparency can make or break a relationship

• The subtle clues in an advisor’s office environment and interactions

• The difference between fun money accounts and dangerous speculation

• How to ensure your advisor’s plan matches your long-term goals

Questions to Think About:

• When’s the last time you reviewed exactly how your advisor gets paid?

• Are you clear on the why behind each investment they’ve recommended?

• Would you feel confident explaining your advisor’s strategy to a friend—or does it sound like a foreign language?

  
  

  This episode originally aired on August 2, 2023. Please disregard any mention of current events. You can find the original show notes here.

  FULL SHOW NOTES: https://stackingbenjamins.com/how-to-spot-a-subpar-advisor-greatest-hits-week-1732

  Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

  Enjoy!

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What were your favorite moments of 2019? Today we'll lay our cards on the table and show you ours, plus what we learned from each of these stellar guests. From composers to chefs, and from iconic investors to artists, today we're going to actually learn something...and from LOTS of different types of personalities. We're very proud of the wide range of topics we covered in 2019, and today we'll take a glimpse of just a few of them with you.

That's not all...of course, we'll leave time for Doug's trivia! Enjoy!

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Money used to be easy. Go to the bank, make a deposit. Maybe you had a pension. Nearly everyone in America had Social Security. How did money become dangerous? We'll sit down with Chris Varelas, the man responsible for brokering some of the biggest mergers and acquisitions in finance. Between working as the head of Citi's technology, media, and communications, and co-founding a private equity firm in Silicon Valley, Chris has acquired a special insight into just how the money game has changed, and his role in some of the biggest financial moments of the last 30 years.

What problems will you encounter on your journey toward financial independence? We'll cover many of those during our headlines. While financial headwinds like expenses, loss, and taxes are roadblocks to a bigger portfolio, we'll key into the main problem nearly everyone will face: YOU standing in the way of your own success. Plus, in our second piece, we'll examine how one rogue broker singlehandedly took down his whole firm. Now THAT is dangerous.

Later we'll throw out the Haven Life Line to Colton, who calls in with a question about paying off some debt with his pension. Colton recently bought a new house and is having a cash-flow crunch. He has $5000 in his pension that he could use to pay off some short-term bills. Should he use the pension, which has a lower interest rate than the bills, to pay off his debts? His pension would grow to be about $15,000 in retirement.

Of course, we'll save some time for Doug's trivia.

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