The Stacking Benjamins Show

Ryan Hawk arrived at Miami University the day after high school graduation, with a plan to earn the starting quarterback job and make it to the NFL. Two years later, a 6'5" kid from somewhere in Ohio showed up and took the job away from him. That kid turned out to be Ben Roethlisberger. What Ryan did with that moment became the entire foundation of The Learning Leader podcast, one of the most respected leadership shows in the country, and his new book The Price of Becoming. He joins Joe and OG to talk about the habits, frameworks, and daily actions that compound into something exceptional -- and what to do when the plan doesn't survive contact with reality.
What You'll Walk Away With
Coach Hepp's three-sentence leadership philosophy that Ryan has never forgotten: have a plan, work the plan, and plan for the unexpected
Why being told "he gives us a better chance to win than you do" was the most valuable coaching Ryan ever received -- and what it teaches about adding value versus wanting credit
The imitate-then-innovate framework: why The Beatles were a cover band first, why Wayne Gretzky took handwritten notes watching players smaller than himself, and why copying the greats isn't theft -- it's the fastest path to finding your own voice
Ryan's first draft pick for becoming exceptional: a five-to-ten minute nightly prompt exercise built around one Charlie Munger question that compounds like a great investment
Why truth tellers -- people willing to look you in the eye and tell you what you need to hear rather than what you want to hear -- are the most underrated asset in any high performer's life
The superpower Ryan has found in every great leader he's interviewed across 11 years and hundreds of conversations: deep, specific curiosity -- and why it's the ultimate form of showing love
Sweat more than you watch other people sweat: Scott Galloway's physical discipline framework applied to every area of life
The Brock Purdy late-round pick: why bringing a notebook to every meeting -- something almost no intern or young employee does -- is the single easiest way to stand out and learn faster
The boomerang kids debate: why nearly half of Americans under 30 now live with a parent, when OG thinks it's a great idea, when he thinks you suck, and why it only works if there's a real plan with a real end date
James from the community: how retiring at 52 let him become his daughter's bank in a hot real estate market -- loan document, market rate, free labor but zero say in the house

Why This Matters Now
The gap between people who become exceptional and people who almost do isn't talent -- it's the daily actions they're willing to stack. This episode is the practical blueprint for what those actions actually look like.
From the Basement
Ryan Hawk joins Joe and OG to talk about getting benched, the imitate-then-innovate path from cover band to original voice, and the five draft picks that build a great life -- including one that Joe immediately connects to hiding money from himself. The Wall Street Journal's piece on boomerang kids gives OG a platform to explain exactly when it's smart, when it's lazy, and why his kids should not take this as an invitation. Doug arrives with Cleveland trivia and the story of how a newspaper's cheap typesetting permanently changed the name of a major American city. James from the community sends a letter that makes OG quietly admit he was wrong about the appraisal.
Resources Mentioned
The Price of Becoming: The Compounding Practices of High Performance by Ryan Hawk -- available wherever books are sold
The Learning Leader podcast -- Ryan Hawk; available wherever you listen to podcasts; learningleader.com
Steal Like an Artist by Austin Kleon -- referenced for the imitate-then-innovate framework
Set for Life by Scott Trench -- referenced for Joe's kids; biggerpockets.com
Broke Millennial by Erin Lowry -- referenced for Joe's kids; brokemillennial.com
Wall Street Journal -- "Living With Your Parents Is No Longer Viewed as a Failure to Launch" by Rebecca Picciotto and Nicholas G. Miller
Stacking Benjamins Field Kit -- stackingbenjamins.com/fieldkit
Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201
Stacking Benjamins Community -- stackingbenjamins.com/basement

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An alarming number of people have access to a 401(k) and are either not using it, not getting the full employer match, or not making the simple moves that turn a good account into a great one. Joe and OG dedicate a full episode to the retirement account that most people take for granted -- covering contributions, matching, investment selection, Roth versus traditional, and the specific decisions that separate people who retire comfortably from people who almost got there. Plus wins from the Stacker community and trivia that will make you the most dangerous person at your next dinner party.
What You'll Walk Away With
Why the employer match is the single highest guaranteed return available to any investor -- and the specific contribution level that captures every dollar of it
Roth 401(k) versus traditional 401(k): the one question that cuts through all the noise and tells you which one to use right now
Why your investment menu feels overwhelming and how to make a great choice in under five minutes using one simple filter
The auto-escalation feature most people never turn on -- and why setting it up once can add tens of thousands of dollars to your balance without you doing anything else
What to do with your 401(k) when you leave a job: the four options, which one is almost always wrong, and which one most people choose anyway
Why contribution limits are higher than most people think -- and the catch-up contribution that becomes available at 50 that most people in their 40s don't know to plan for
The vesting schedule trap: why your employer match might not actually be yours yet -- and what that means for anyone thinking about leaving their job
Why 403(b) and 457 plans follow most of the same rules -- and the one unique advantage the 457 has that almost nobody knows about
OG on the single most common 401(k) mistake he sees in client portfolios -- and how long it typically takes to fix
Stacker wins from the community: the specific moves people made this month that are already paying off
Why This Matters Now
Every year you don't optimize your 401(k) is a year of compounding you don't get back. The moves in this episode are not complicated -- but most people either don't know about them or keep putting them off. This is the episode to send to anyone who has a 401(k) and has never really looked at it.
From the Basement
Joe and OG celebrate the 401(k) in mom's basement while OG recovers from completing the Triple Bypass -- a Colorado cycling event that covers three mountain passes and approximately all of the elevation gain in the western hemisphere. OG's wife asked if he'd do it again. He answered with a childbirth analogy. Doug arrives with trivia that will be re-shared all week. The community delivers wins that prove the system works.
Resources Mentioned
Stacking Benjamins Basics Guide -- stackingbenjamins.com/basicsguide
Stacking Benjamins Field Kit -- stackingbenjamins.com/fieldkit
Stacking Benjamins BAD Groups -- stackingbenjamins.com/bad
Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201
OG financial planning calendar -- stackingbenjamins.com/og
Stacking Benjamins Community -- stackingbenjamins.com/basement

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A Wall Street Journal story about a 17-year-old helping his family with financial decisions kicks off a much bigger Stacking Benjamins question: who should you actually trust with your money? Joe, Doug, Paula Pant, Jesse Cramer, and special guest Roger Whitney dig into where great advice comes from, why bad advice often comes from people who love you, and how to build a better filter before you act. Along the way, they talk books, podcasts, family advice, AI, confirmation bias, homebuying myths, index funds, retirement plans, and why "smart" isn't enough.
What You'll Walk Away With
Why Roger says "advice" has a high bar: real advice should apply to your specific life, not just sound smart in public
The difference between information and advice -- and why confusing the two can lead you into trouble
Why books often beat random internet advice: they usually have more vetting, structure, and accountability
How well-meaning friends and family can still give terrible money advice when they speak confidently about things they don't really understand
Paula's advice pyramid: avoid people who profit from outrage, be skeptical of people with no accountability, and seek sources with both expertise and vetting
Why AI can be useful as a sparring partner, but not as a substitute for your own thinking or fact-checking
The danger of "always" and "never" advice: always buy a house, always max your 401(k), never finance a car, always buy index funds
Why renting isn't automatically throwing money away -- and how the price-to-rent ratio can help you think more clearly
Why maxing out your workplace retirement plan may not always be the right move, especially when tax flexibility, business investment, or other goals matter more
How confirmation bias, present bias, and absolute certainty can fool you into believing your plan is stronger than it is
What to look for in your personal board of directors: people you respect, people with a high signal-to-noise ratio, and people who are kind enough to tell you the truth
Why Roger says a kind person is better than a merely nice one when you need real feedback
Why This Matters Now
Financial advice is everywhere: podcasts, books, TikTok, AI, coworkers, relatives, advisors, and confident strangers with strong opinions. The hard part isn't finding advice. It's knowing which advice deserves your attention. This episode gives Stackers a filter for separating useful guidance from noise before the wrong voice gets too close to their money.
From the Basement
Joe uses a Wall Street Journal piece about a teenage family financial advisor to launch a bigger card-table debate with Paula Pant, Jesse Cramer, and Roger Whitney. The crew builds a money-advice pyramid, debates which financial rules should be ignored, and explores when to trust yourself versus when to bring in your board of directors. Doug celebrates Art Linkletter with Game of Life trivia, Paula admits she's never played it, and OG's trivia lead might get a little more uncomfortable.
Resources Mentioned
The Wall Street Journal piece by Oyin Adedoyin about a 17-year-old helping his family with financial decisions
Roger Whitney -- The Retirement Answer Man podcast
Paula Pant -- Afford Anything podcast
Jesse Cramer -- Personal Finance for Long-Term Investors podcast
Seth Godin -- Linchpin
Thomas Stanley and William Danko -- The Millionaire Next Door
Robert Kiyosaki -- Rich Dad Poor Dad
Robert Cialdini -- Influence
Richard Feynman -- Surely You're Joking, Mr. Feynman!
Beth Kobliner -- referenced as an upcoming Afford Anything guest
Stacking Benjamins Newsletter, The 201 -- stackingbenjamins.com/201
Stacking Benjamins YouTube channel -- youtube.com/stackingbenjamins
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In the 1800s, the smartest financial advice your grandparents could receive was: don't save money, because it will probably go to zero. Stocks were considered scams. Real estate was the only real path to wealth. Crypto isn't the future, it's a replay of something that happened dozens of times before the Civil War. Dr. Joseph Moore is a historian, a New York Times bestselling author, and someone who has spent his career proving that what always worked was always changing. His book is How to Get Rich in American History, and this conversation will make you rethink at least three things you currently believe about money.
What You'll Walk Away With
Why grandparents in the 1800s told their grandchildren never to save money -- and why that advice was completely rational at the time
The crypto-as-past argument: why self-issued currencies have existed since before the Civil War, why they all eventually went to zero, and what the one thing is that actually made the US dollar trustworthy
Why stocks beating bonds in the long run is only true since World War II -- and what that means for treating any historical financial truth as permanent
The go-ahead philosophy: why Americans used to define success as actively moving forward rather than passively not falling behind -- and why that shift in language reveals something important
Why financial gurus get a worse reputation than they deserve -- and the German economist's study that showed Dave Ramsey alone has saved the US economy the GDP of a mid-sized nation state
The FIRE movement isn't new: the original four-hour workday, a man with Ten Acres Enough in 1850s New Jersey, and what the Nearings' Vermont maple farm story actually teaches about the selling of early retirement
Fast time versus slow time: why the financial media is paid to tell you it's always fast time, why it's almost never fast time, and how to know the difference when it actually matters
Why the 4% rule and the safe withdrawal rate are research findings worth knowing -- and exactly why building a 30-year financial plan around a fixed number is still a mistake
Five first-half 2026 lessons from the Stacking Benjamins mentor vault: creativity, adversity, mistakes, the go-ahead mindset, and compounding
The compounding belief problem: why OG's framework for trusting the math you've already lived is the most underrated motivational tool in personal finance

Why This Matters Now
Every financial truth that feels permanent right now -- index funds always win, real estate always appreciates, crypto is either the future or a scam -- is newer than you think and more conditional than it sounds. The investors who build real flexibility into their plans are the ones who survive when the conditions change. And the conditions always change.
From the Basement
Dr. Joseph Moore joins Joe and OG to pick fights with crypto, passive income, real estate mythology, Napoleon Hill, and the entire academic finance establishment -- while making the case that financial gurus, properly understood, have done more measurable good for American wealth than all the finance professors combined. OG is in Colorado acclimating for a bicycle climb that has Doug genuinely concerned about whether a financial co-host counts as a dependent. Doug arrives with trivia tied to today's birthday that connects Nintendo's origins to something nobody expected. Five mentor highlights from the first half of 2026 close the episode -- including clips from George Newman on creativity, Jim Murphy on adversity, Bola Sokunbi on surviving a very expensive rollover mistake, Beth Kobliner on why young people are gambling instead of saving, and Cody Berman on the compounding moment that changes everything.
Resources Mentioned
How to Get Rich in American History by Dr. Joseph Moore -- New York Times bestseller; available at bookstores and on Amazon; josephmoore.com
Inner Excellence by Jim Murphy -- referenced for mental strength and adversity; available wherever books are sold
Clever Girl Finance -- Bola Sokunbi; clevergirlfinance.com
Afford Anything podcast -- Paula Pant; referenced in first-half mentor recap
Retire by 30 by Cody Berman -- retireby30book.com
Get a Financial Life by Beth Kobliner -- referenced in first-half mentor recap
Stacking Benjamins Field Kit -- stackingbenjamins.com/fieldkit
Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201; write Joe at joe@stackingbenjamins.com with your favorite first-half lesson
Stacking Benjamins Community -- stackingbenjamins.com/basement

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Small company stocks were up nearly 22% in the first six months of 2026. Emerging markets were up 24%. Meanwhile, plenty of people sat on the sidelines convinced those asset classes were dead, chased last year's winners, or just didn't know what they owned. Joe, OG, and Len Penzo break down the first-half scorecard, explain why the lesson isn't about timing -- it's about diversification -- and walk through what an investment policy statement actually is and why having one would have kept most people out of trouble.
What You'll Walk Away With
The first-half 2026 scorecard: Russell 2000 up 21.9%, MSCI Emerging Markets up 24%, S&P 500 up 9.6%, and why the breadth of the rally matters more than the headline number
Why OG's one-sentence takeaway -- "the plan always works" -- is both right and incomplete, and what Len's personal experience this year adds to the conversation
What an investment policy statement actually is: the one-page written decision tree that protects you from making bad moves when markets spike or crash
Why the market closes at an all-time high roughly 30% of the time -- and what that means for the "I'm waiting for it to come down" crowd
How to x-ray your portfolio: the specific inventory OG recommends taking before you make any changes
Why you should rebalance all at once rather than filling in holes slowly -- and the one asterisk that applies before you do anything in a taxable account
Len on the mining sector: why GDX returned 154% last year and is down 10% this year -- and exactly what that pattern teaches about chasing returns
Why trying to explain your investment plan to another human being is the best stress test you have
The allowance micro-economy problem: what happens when you pay kids per task and they start pricing everything in units of dog poop
Jessica's win from the Basement: how one Stacker helped her 25-year-old cousin sign up for her first 401(k), get the full company match, and choose index funds
Why This Matters Now
The second half of 2026 starts now. If you don't know what you own, why you own it, or what you'd do if it dropped 30%, this is the episode to act on before the next six months get away from you.
From the Basement
Joe, OG, and Len Penzo review the first half of 2026, build a case for why diversification beats prediction every time, and explain what an investment policy statement is and how to write one. Doug celebrates the Hollywood sign's origin as a real estate advertisement and shares two things social media actually taught us -- including a TikTok comedian voicing the thoughts in Mark Zuckerberg's ear during a very long beef discussion. Len's annual sandwich survey is about a month away. True Money Stories is climbing the Amazon charts.
Resources Mentioned
True Money Stories by Len Penzo -- available on Amazon; lenpenzo.com
Len Penzo dot com -- lenpenzo.com; 3,000 articles, 18 years of personal finance writing
Stacking Benjamins Field Kit -- stackingbenjamins.com/fieldkit
Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201
Stacking Benjamins Community -- stackingbenjamins.com/basement
OG financial planning calendar -- stackingbenjamins.com/og
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.