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Lyt når som helst, hvor som helst 

Joe Saul-Sehy and Josh ‘OG’ Bannerman

Named Best Personal Finance Podcast by Bankrate.com and Kiplinger — and the only podcast the Plutus Awards retired from competition after winning twice — The Stacking Benjamins Show is personal finance that doesn’t put you to sleep.

Hosts Joe Saul-Sehy (former 16-year financial advisor, ex-WXYZ-TV “Money Man”) and Josh “OG” Bannerman, CFP (Certified Financial Planner, Bannerman Wealth) sit around the card table in Joe’s mom’s half-finished basement in Texarkana and talk money with the smartest guests in personal finance, investing, and behavioral economics. As Fast Company wrote, the show “strikes a great balance of fun and functional.”

Every Monday, Wednesday, and Friday: expert guests, real headlines, listener questions, and Doug’s trivia. Topics include investing, retirement planning, budgeting, real estate, behavioral finance, taxes, and financial independence — for anyone who wants to be smarter about money without being talked down to.

Subscribe to The 201 — the free newsletter that goes deeper than the show — at stackingbenjamins.com/201

The Stacking Benjamins Show

Most people measure a bad boss in bad days: the meeting that went sideways, the credit that got stolen, the comment that stung longer than it should have. Money Mentor Mel Abraham, along with Paula Pant and the crew, argues that's the wrong unit of measurement entirely. A toxic work situation has a real, compounding financial cost, in stalled raises, atrophied skills, drained energy, and years quietly lost to a job that was never going to get better. Today's episode puts a number on it, and gives you the exact steps to build your way out.

What You'll Walk Away With

 • Why a bad boss almost always means you're being underpaid too, and the compounding effect that has on your entire career
 • A simple "stay, fix it, or go" framework for evaluating your specific work situation, tested against real scenarios
 • Why waiting for the "right time" to leave a toxic job often means waiting far too long
 • The financial prep work worth doing now, even if your job is fine today, so you're ready to move fast if it isn't tomorrow
 • Why your skills and confidence can quietly atrophy under a bad boss, even if your paycheck stays the same
 • How to separate your relationships with great coworkers from your relationship with a bad workplace
 • A practical first-week plan for anyone who gets laid off or walks away suddenly, starting with what actually needs to be true immediately

Why This Matters Now

A difficult boss or a dead-end job rarely shows up as one dramatic moment. It shows up as a slow leak: a raise you didn't ask for, a skill you didn't build, an idea you didn't pitch because you'd stopped believing it mattered. That slow leak is expensive, and it's also fixable. Building financial and career readiness before you need it, savings, low fixed costs, a sharpened skill set, means the decision to leave becomes a choice you're making on your own terms, not a scramble you're forced into.

From the Basement

The crew's trivia detour into Philippe Petit's famous 1974 high-wire walk between the Twin Towers turns into a surprisingly close four-way guessing game, complete with hometown bragging rights and a mid-season trivia standings shakeup that's still anyone's game.

Resources Mentioned

Building Your Money Machine by Mel Abraham • — Mel's USA Today bestseller on building financial freedom
Building Your Money Machine podcast • — Mel's weekly show on wealth-building and financial freedom
Afford Anything podcast • — Paula Pant's show, referenced episode: "Should We Retire in Our 40s with $4 Million?"
Granola • — AI-powered meeting notes tool mentioned in the sponsor break

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What a Bad Boss Is Actually Costing You (SB1881)

It's easy to walk out of a rushed appointment, an unexplained bill, or a denied claim and quietly blame the person in the white coat. Doc G (Doctor Jordan Grumet), the hospice physician and longtime Stacking Benjamins favorite, argues that's exactly the wrong target, and that the confusion isn't an accident. Somewhere between the insurance company, the pharmaceutical company, the private equity firm, and the electronic records system, a lot of people are getting paid, and the two groups actually providing and receiving care are left holding the bag. Here's the good news: almost nobody appeals a denial, and appeals win far more often than you'd expect. This episode gives you the real playbook.

What You'll Walk Away With

 • The exact first move to make when a claim gets denied, and why documenting it matters more than people realize
 • Why a procedure can get pre-approved and still get denied months later, and what to save to protect yourself
 • A simple "who do you call first" framework for untangling a prescription, billing, or coverage problem
 • The pharmaceutical industry trick of repackaging old drugs as "new" ones, and the one question that sidesteps it completely
 • How to spot whether your doctor's office is privately owned or backed by private equity, and why it changes the care you get
 • Why so much unnecessary testing exists purely to protect doctors from lawsuits, not to protect you
 • The real math on insurance appeals, and why giving up is exactly what the system is counting on

Why This Matters Now

Healthcare confusion isn't just an annoyance, it's a real financial risk hiding in plain sight. A denied claim, a surprise bill, or a medication that suddenly isn't covered can undo months of careful budgeting in a single afternoon. The difference between losing that fight and winning it usually isn't luck, it's knowing the specific, doable steps to push back before you give up. This isn't about becoming your own doctor or insurance expert. It's about not getting steamrolled by a system that's counting on you not knowing what to do next.

From the Basement

A story about FedEx's founder famously saving the company with a lucky night at a Vegas blackjack table becomes the day's trivia detour, and somehow ties neatly back into an episode all about refusing to give up when the system says no.

Resources Mentioned

The Healthcare Heist by Jordan Grumet, MD • — Doc G's new book on fixing the doctor-patient relationship
Earn & Invest podcast • — Doc G's award-winning personal finance podcast

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What to Do When Insurance Denies Your Claim (And Why They Count on You Giving Up) SB1880

There's a strange thing that happens to a lot of people as their income grows: the anxiety doesn't go away, it just changes shape. More money, more accounts, more to track, and somehow the same low hum of worry every time a bill comes due. Jesse Mecham, founder of YNAB and one of the most trusted voices in budgeting, has spent over two decades helping people fix that, and his conclusion isn't a better spreadsheet or a stricter budget. It's a single question, one that sounds almost too simple to matter, until you actually try to answer it.

What You'll Walk Away With

 • The one question that replaces budgeting guilt with genuine clarity, and why it works even for people who "already have money figured out"
 • Why looking backward at your spending almost never makes you feel better, and what to do instead
 • The five categories every dollar actually falls into, and why skipping even one of them creates financial blind spots
 • Why future income should never be allowed to rescue your current plan, and how that habit quietly leads to credit card debt
 • A surprisingly simple system for making irregular bills stop feeling like emergencies
 • The real story of a Costco cashier who became a millionaire without doing anything complicated, and what it says about the myth of needing to "get fancy" with money
 • Why money worry doesn't disappear once you have more of it, and what actually makes it go away

Why This Matters Now

It's easy to assume that financial peace is just one income bump away. Get the raise, pay off the card, hit the next savings milestone, and the anxiety will finally quiet down. But that's rarely how it actually works. Real financial confidence comes from knowing exactly what your money is for, not from having more of it. That clarity is available at any income level, and it's the difference between managing money and constantly feeling managed by it.

From the Basement

A story about a seventh-grade inline skating competition, complete with donated gear, mystery sponsors, and an unauthorized parking lot, turns out to be the unexpected origin story behind one of personal finance's most beloved communities. Some of the best lessons about building something people care about show up in the most unlikely places.

Resources Mentioned

Never Worry About Money Again by Jesse Mecham • — Jesse's new book on purpose-based spending
YNAB (You Need A Budget) • — Jesse's budgeting app and free trial

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Jesse Mecham (YNAB Founder) On The One Question That Ends Money Anxiety For Good (SB1879)

Most people only think about taxes twice a year: while filing, and while dreading filing next time. That gap is exactly where expensive surprises are born. Today's episode is a genuine mid-year tax tune-up, the kind of checkup that takes maybe twenty minutes and can quietly save you from an ugly bill, an unexpected penalty, or a refund that wasn't actually a win. No jargon-heavy lecture, just a clear walkthrough of what to check right now while there's still time to fix it.

What You'll Walk Away With

 • Why a big tax refund last year tells you almost nothing about whether you're on track this year
 • The four numbers you actually need to know to build your own mini tax forecast in one sitting
 • How the IRS "safe harbor" rule works, and the two different percentage thresholds that keep you penalty-free
 • A common myth about side hustle income that trips up more people than you'd expect
 • Why switching to a Roth 401k without a plan can quietly blow a hole in your monthly cash flow
 • The real math behind donor-advised funds, and why writing a check to charity may be leaving money on the table
 • A simple gut-check for figuring out whether you need a professional or can handle a financial fix yourself

Why This Matters Now

In your 40s, your financial life usually gets more complicated before it gets simpler: a raise here, a side hustle there, maybe two incomes in the household, maybe a bonus that shows up at an inconvenient time. Each of those changes quietly shifts what you owe, and waiting until April to notice means you've lost your best chance to do anything about it. A twenty-minute check now isn't about becoming a tax expert. It's about making sure next spring is boring instead of stressful, which, when it comes to taxes, is exactly the goal.

From the Basement

A home AC disaster turns into an unexpectedly useful lesson about getting a second opinion before writing a big check, whether it's for a repair, a service, or apparently, a $3,000 HVAC estimate that turned out to be a $300 fix. Consider it a bonus lesson in trusting your gut when something doesn't add up.

Resources Mentioned

Stacking Benjamins Tax Guide • — free guide for organizing your mid-year tax review
Stacko Financial Action Month board • — the interactive game with a money move for each day
Field Kit Finance • — track net worth, spending, and subscriptions in one place
Daffy • — donor-advised fund platform referenced for charitable giving strategy
IRS Estimated Tax Payments • — where to make an estimated payment directly

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Your Mid-Year Tax Checkup: Fix Problems Before They Become April's Problem (SB1878)

Three genuinely sharp financial minds sit down today and, one by one, admit to the same kind of dumb money moves everyone else makes. Not because they didn't know better. Because knowing better and doing better turn out to be two completely different skills, and your brain is very good at making bad ideas feel reasonable in the moment. This episode isn't about learning new investment tactics. It's about learning to recognize the exact moment your own mind starts working against you, and what to do about it before it costs you.

What You'll Walk Away With

 • The three specific flavors of overconfidence that combine into what one expert calls "a recipe for disaster"
 • Why "I'll wait until it comes back" is one of the most dangerous sentences an investor can say to themselves, and when it's actually true
 • The surprising reason financially literate people still make emotional money mistakes, according to research on an unrelated profession
 • A simple writing exercise that makes you far more likely to stick to your own financial plan
 • Why betting on what's familiar, your employer's stock, your home country's market, is quietly one of the riskiest things you can do
 • A martial-arts-inspired mental trick for turning your own biases into tools instead of traps
 • The real reason "this time is different" almost always feels true and is almost always the wrong conclusion to act on

Why This Matters Now

In your 40s, you've likely made enough financial decisions to have a track record, some smart, some you'd rather not revisit. The goal isn't to eliminate emotion from money; that's not realistic, and it's not even the point. It's to recognize the specific moments your gut is about to overrule your plan, and to have something in place, a rule, a person, a system, that catches you before it does. Confidence with money doesn't come from never being tempted to make a bad call. It comes from knowing exactly what you'll do when you are.

From the Basement

The crew's year-long trivia championship takes a wild turn with a Spanish treasure fleet question that somehow ends in someone getting bonus points for pure luck, which is a fittingly ironic way to close an episode all about how bad we are at judging our own luck.

Resources Mentioned

The Behavioral Investor by Daniel Crosby • — second edition available for preorder
Afford Anything podcast • — Paula Pant's show
Personal Finance for Long-Term Investors podcast • — Jesse Cramer's show

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Why Smart People Make Dumb Money Decisions SB1877

Homeowners insurance prices are up a whopping 24% since 2022. One in seven homeowners now has no insurance at all. In some parts of the country, companies aren't just raising rates -- they're refusing to write policies. Bob Litterman co-created the Black-Litterman model that the financial industry still uses to price risk, spent 23 years running risk at Goldman Sachs, and now chairs the Coalition for an Insurable Future. He joins Joe and OG on a special Thursday episode to explain what's actually happening, why it's not going to stop, and what you can do about it right now.

What You'll Walk Away With

 • Why the insurance market breaks down when probabilities stop being stable -- and how billion-dollar weather events went from three per year in the 1980s to 23 per year today
 • The domino chain: how rising insurance costs in one ZIP code can drive down home values, freeze bank lending, shrink local businesses, and quietly hollow out an entire community
 • Why this isn't 2008 -- and the one important way it's actually worse than what the mortgage crisis taught us
 • Why one in seven homeowners now carries no insurance at all -- and what that means for the next major weather event
 • The 100-year flood problem: why homes built to withstand a once-in-a-century event are now getting hit every five to ten years
 • What first-time homebuyers should ask that their realtor almost certainly won't bring up -- and why the insurance question is now as important as the mortgage rate
 • How to actually read your renewal letter: what to look for beyond the premium, what hidden changes insurance companies are legally required to disclose, and why your deductible may have quietly doubled
 • OG's Claude trick: how he uploaded both his old and new policy documents, asked for the differences, and found actionable savings plus a jewelry rider gap he didn't know he had
 • Why Bob says the real mispricing isn't in the insurance market -- it's in the pollution market -- and what that means for how this eventually gets resolved
 • The risk management reframe: why thinking about insurance is the wrong starting point, and what to think about instead

Why This Matters Now

This isn't an inflation blip. The risk is genuinely increasing, the models are being rewritten in real time, and the insurance companies pulling out of markets are the canary in the coal mine. The good news: there are specific things you can do right now -- at your house, with your policy, and in how you think about risk -- that most homeowners haven't done yet.

From the Basement

Bob Litterman joins Joe and OG on a special Thursday episode to walk through the home insurance crisis from the inside -- the pricing models, the domino chain, the reinsurance squeeze, and the difference between a tail event and the slow-moving sea level rise underneath it. OG's takeaway: upload both your old and new policy to Claude and ask it to find the differences before your next renewal. Doug arrives with flood insurance trivia tied directly to the episode content. The Coalition for an Insurable Future, a nonpartisan cross-industry group, made this episode possible. Stacking Benjamins received compensation for this episode.

Resources Mentioned

 • Coalition for an Insurable Future -- nonpartisan cross-industry group on climate and insurance risk; coalitionforaninsurablefuture.com
 • Black-Litterman Model -- referenced for Bob Litterman's background in risk pricing
 • Climate Central -- tracks billion-dollar weather events annually; climatecentral.org
 • National Flood Insurance Program -- referenced for the 1968 government backstop for flood risk; floodsmart.gov

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Why Your Homeowners Insurance Bill Keeps Going Up (And What to Do About It) Special Episode SB1876

Odds are good that part of your paycheck disappears into an account with the Fidelity name on it every two weeks. Almost nobody stops to ask who's actually on the other end of that relationship. The answer isn't a faceless Wall Street institution, it's one family that has quietly controlled a $15 trillion company for three generations, through boardroom near-mutinies, a succession fight that almost ended in the company being sold, and enough family drama to fill a book. It did, actually. Wall Street Journal reporter Justin Baer spent years uncovering it, and today he brings the whole story down to the basement.

What You'll Walk Away With

 • Why one of the biggest financial companies in America has never had a single outside shareholder, and what that's actually protected them from
 • The surprisingly personal origin story behind Fidelity's founder, and the market-crash lesson that shaped the entire company's philosophy
 • Why Fidelity almost missed the money market fund revolution, and the workaround that changed how everyday people access their cash
 • The near-sale that almost happened in 2005, and how close the company came to becoming something completely different
 • Why checking your 401k balance more often might actually be good for your financial decision-making, according to Fidelity's own research
 • How a family succession battle nearly pushed the current CEO out of the business entirely
 • A useful mental gut-check for figuring out how much of your "checking account cushion" should actually count as part of your emergency fund

Why This Matters Now

If you're in your 40s, there's a good chance you've had a relationship with Fidelity, Vanguard, or a similar company for two decades without ever really knowing how they work or who's behind them. That's not a knock on you, it's just how most financial relationships start: automatically, through a job, without much choice involved. Understanding the incentives and history behind the company holding your retirement money doesn't change your investing strategy overnight, but it does replace a vague, faceless trust with something more informed, and informed trust is a lot more durable than blind trust.

From the Basement

A conversation about $189 average dates turns into a surprisingly sharp point about not overspending to impress someone before you even know if it's a match, in relationships or business. And a basement community note about "hidden" emergency funds sitting in checking accounts sparks a genuinely useful reframe worth stealing for your own budget.

Resources Mentioned

House of Fidelity: The Rise of the Johnson Dynasty and the Company That Changed American Investing • — Justin Baer's book on the Johnson family and Fidelity's history
Field Kit Finance • — the all-in-one net worth, budgeting, and credit tracking tool mentioned in the sponsor break

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Meet the Family That Quietly Controls Your Retirement Money (SB1875)

There are three words that quietly end up costing more than almost any bad investment: "he handles it." Not because delegating is wrong, but because somewhere between division of labor and total disengagement, a line gets crossed that most couples never notice until a crisis forces them to. This episode is about that line, and about the less obvious ways money stress shows up when it's not just a spreadsheet problem, it's a physical one. Jill Schlesinger and Kristy Talorico both join the show, and each brings something you didn't know you needed to hear.

What You'll Walk Away With

 • The real difference between splitting responsibilities and losing all visibility into your own financial life
 • A simple, low-stakes way to start a money conversation with a partner who's checked out, without triggering defensiveness
 • Why financial advisors dread meeting a client's "uninvolved" spouse for the first time after a death
 • What actually happens to your financial life if your money-handling spouse suddenly can't do it anymore
 • How financial stress physically changes your body, according to a major new health study
 • Why the standard advice to "just put more in your 401k" completely misses people who are financially struggling right now
 • The surprising first place financial counselors suggest looking before you take out any kind of loan
 • A behind-the-scenes look at how employers are (and aren't) using workplace benefits to actually help people

Why This Matters Now

In your 40s, you're often the connective tissue for your whole household's financial life, sometimes for a spouse, sometimes for aging parents, sometimes for kids just starting out. It's easy to assume that as long as someone in the relationship understands the money, everyone's fine. But real financial confidence means everyone involved has at least a working map of where things stand. This episode isn't about becoming an expert. It's about making sure "I don't really know" is never the answer when it matters most.

From the Basement

Doug's trivia question drags in an unexpected lesson about knowing what things actually mean, not just recognizing the name, which somehow ties together German car history and financial literacy in the same segment. Basement logic, but it works.

Resources Mentioned

Money Moves with Jill Schlesinger • — Jill's new podcast with Mark Talercio
Jill on Money podcast • — Jill Schlesinger's long-running personal finance show
"The Most Dangerous Words I Hear From Married Couples: 'He Handles It'" • — the Kiplinger piece referenced in the episode
Brightside Financial Care • — Kristy Talorico's company, financial care benefits for employers
Findhelp.org • — the free navigation tool for local financial and hardship resources

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

The One Financial Conversation People Avoid (Plus a Discussion about Stress and Money) SB1874

There's a new bill in Washington that sounds like a fix but is really just a promise to eventually have a debate about one. That's not why this episode matters. What matters is that Social Security is suddenly everywhere in the headlines, and if you've been putting off understanding how your own claiming decision actually works, that's a gap that gets more expensive the longer it sits. This episode is the one to finally close it. No single mistake, no one hot take, just a real walkthrough of the claiming ages, the spousal rules, the survivor benefits, and the myths that trip people up most, so you can stop guessing and start deciding with confidence.

What You'll Walk Away With

 • Why the "estimated benefit" number on your Social Security account can be wildly wrong, especially if you're not planning to work until 67
 • The real reason waiting until 70 pays off, and why it has almost nothing to do with growth
 • A subtle, surprisingly common mistake that can quietly wreck a smart claiming strategy years after you made it
 • What actually happens to your benefit if your spouse passes away first, and how remarriage timing can change everything
 • Why the industries where workers never pay into Social Security create a completely different retirement math
 • The dollar threshold that can force you to pay back benefits you already claimed
 • A 2024 rule change that may directly affect certain public employees and hasn't gotten nearly enough attention
 • Why raising the retirement age matters a lot less than people assume, depending on how you actually want to retire
 • How a totally different tax, the Medicare surcharge, quietly rides along with your Social Security decisions
 • A quick true-or-false round that separates Social Security fact from the myths everyone repeats

Why This Matters Now

If you're in your 40s, Social Security can feel like something to figure out later, right up until a headline makes it feel urgent and confusing at the same time. The truth is, you don't need to predict what Congress will do. You need to understand the mechanics that are already in your control: when you claim, how you and a spouse coordinate, and how your own work history shapes the number. Get that right, and you turn a source of money stress into one less thing you have to worry about, freeing up mental space for the parts of your financial life you actually want to think about, like the next trip, not the next committee hearing.

From the Basement

Doug tests his trivia chops with a game built to separate fact from political fantasy, and OG gets fired up about something that has absolutely nothing to do with retirement, and everything to do with golf tickets. It's the reminder that even a deep dive into claiming strategy still comes with a little basement chaos along the way.

Resources Mentioned

The PROMISE Act, explained • — CNBC's breakdown of the bipartisan bill and the 2032 trust fund deadline
Create your SSA.gov account • — check your earnings history and benefit estimate
id.me login for SSA.gov • — the identity verification step for your Social Security account
The Walt Disney Company: Walt's Era — Acquired podcast • — the four-hour deep dive Doug referenced on Disney, Oswald the Rabbit, and protecting your name
Stacking Benjamins Guides • - Scout + a quick and easy checklist are just two of the reasons these complete reference tools are your top choice to manage your HR Benefits, your taxes, or college planning.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Everything You Actually Need to Know About Social Security Right Now (SB1873)

A former OpenAI researcher went on Diary of a CEO and said there's a 70% chance AI ends badly for humanity, told his wife they shouldn't have more children because they'd never enter the workforce, and gave up $2 million by refusing to sign a non-disparagement clause to say it publicly. Joe asks Paula Pant, OG, and Jesse Cramer to react -- not as AI experts, but as people who've watched the internet, robots, computers, and cars all supposedly end the economy, and as people who actually know what to do with your money when the world feels uncertain.

What You'll Walk Away With

 • Paula's case for being a negative 10 on the worry scale: why 60% of jobs that exist today didn't exist in 1940, and why AI is more likely to create new categories of work than eliminate work entirely
 • Jesse's case for a four: why knowledge is being commoditized the same way gasoline was -- and what that means if your competitive advantage has always been what you know
 • OG's framework for separating the parts of your job AI will gladly take from the parts it never will -- and why that distinction is more useful than panicking about either half
 • The Jevons Paradox: why making something cheaper almost always creates more demand for it, not less -- and why that applies to patents, legal filings, and every other knowledge-work category people think AI will eliminate
 • Safe, evolving, or replaced: the roundtable verdict on CPAs, software engineers, and customer service reps -- and the Capital One research that reveals why some people actually prefer talking to a machine
 • Why learning the AI tools right now -- even if you're 58 and four years from retirement -- is the modern equivalent of learning email in 1993
 • JL Collins' line that applies to careers just as much as portfolios: flexibility is the only true security
 • Should you buy an AI sector fund? OG, Paula, and Jesse each answer -- and the answer that surprised everyone is probably not the one you'd expect
 • Why OG's Triple Bypass bike race analogy is the best career advice in the episode: if you're always ready, you never have to get ready
 • The window tax trivia that AI got spectacularly wrong -- proving, on an episode about AI taking all our jobs, that it can't even count windows yet

Why This Matters Now

The fear is real. The timeline is uncertain. And the people most likely to be okay are the ones who are building flexibility into their finances and their careers right now -- not because AI is definitely coming, but because it's always smart to be ready for the thing that might come.

From the Basement

Paula Pant, OG, and Jesse Cramer react to a former OpenAI researcher's apocalyptic Diary of a CEO interview -- and spend most of the episode arguing about whether to panic, which jobs survive, whether to buy the AI sector fund, and what OG's fighting robot would do to Jesse's house. Doug arrives with window tax trivia that AI generated incorrectly -- which Joe caught just before air -- and handing one of our contributors a huge win. Financial Action Month is coming next week: five episodes, a bingo sheet, and more to come.

Resources Mentioned

 • Diary of a CEO -- Steven Bartlett interview with Daniel Kokotajlo, former OpenAI researcher
 • Tony Robbins interview with Ray Kurzweil -- referenced for additional AI perspective; linked at stackingbenjamins.com
 • Afford Anything episode 693 -- Paula Pant interview with Dr. Ben Zweig on AI and the workforce; affordanything.com/episode693
 • Personal Finance for Long-Term Investors (PFLTI) -- Jesse Cramer; upcoming AMA episode 19 and episode 150 personal AMA
 • Anthropic Skill Jar -- free AI training; referenced by Paula for learning Claude features
 • Delivering Happiness by Tony Hsieh -- referenced for the Zappos customer service model
 • OG financial planning calendar -- 
stackingbenjamins.com/og • Stacking Benjamins Newsletter (The 201) -- 
stackingbenjamins.com/201 • Stacking Benjamins Community -- 
stackingbenjamins.com/basement

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A Former OpenAI Researcher Says 70% Chance of Human Extinction -- Here's What to Do With That SB1872

How many times have you said the words, “You should sell these?” to someone after experiencing their creativity? We all have. Let’s admit it. We’re built to think about selling things that we’re good at. From our handiwork to our speaking skills, whenever you’re good at something, the highest compliment seems to be, “You’re good enough to sell this! Start a business!”

But should we?

Today we talk to THREE business owners about this very topic. Our special guest, Caleb Guilliams, runs the successful Better Wealth YouTube channel and podcast. OG runs a successful financial advisory firm, and our newest roundtable regular, Paulette Perhach, operates a successful writing/coaching operation. Does it make sense to mix your passion with your business? What are the surprises you encounter if you even try? We’ll cover all of that PLUS continue our yearlong trivia contest between our contributors on today’s show.

You’ll find show notes for this episode at www.stackingbenjamins.com/caleb-guilliams-roundtable-1254.

Deeper dives with curated links, topics, and discussions are on our newsletter, The 201, available at StackingBenjamins.com/201.

Enjoy!

 

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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Passion & Business: Match Made in Heaven or Hell?

Lyt når som helst, hvor som helst

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