Skippy and Doogles Talk Investing

By Skippy and Doogles

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Category: Investing

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Episodes: 297

Description

For years, two of the world's greatest investing minds, Skippy and Doogles, have debated their investing philosophies. They started recording their phone calls to bring that stock market wisdom to the masses. Buckle up, because you never know where these conversations might go, and what kind of priceless investment knowledge will soon hit your mentals.

Episode Date
The Long And Short Of It (CoreWeave, trolley problem)
Oct 19, 2026
A Fool and His Money Are Having a Blast (Chinese manufacturing, SpaceX, Robinhood)
Oct 12, 2026
The Zuck Stops Here (Zuckerberg, student loans)
Oct 05, 2026
America Is 75% Off
Sep 28, 2026
Don't Let Facts Ruin a Good Forecast (OpenAI, the Lakers)
Sep 21, 2026
The Check Is In the Mail (Trump dividend, Coast FI)
Sep 14, 2026
Debt It Like It's Hot (Robert Kiyosaki, Nvidia, Broadcom)
Sep 07, 2026
If You Can’t Beat the House, Maybe Buy the House (Inside FanDuel's Stock) [Investment Committee]
Aug 31, 2026
You Had Me at Pancake Robot (Travis Kalanick's journey to Atoms)
Aug 24, 2026
I'm Not Profit, You're Profit
Aug 17, 2026
Reread My Returns Until You Understand
Aug 10, 2026
Leopold and the Terrible, Horrible, No Good, Very Leveraged Month
Aug 03, 2026
No Train, No Gain
Jul 27, 2026
AI Better Work Out
Jul 20, 2026
You Reap What You Seed
Jul 13, 2026
All Eggs, No Goose
Jul 06, 2026
The Joneses Are Everywhere
Jun 22, 2026
A Degree Too Far
Jun 15, 2026
Anthropic Thunder
Jun 01, 2026
Houston, We Have a TAM Problem
May 25, 2026
A Dog’s Life Economy
May 18, 2026
Our Losers Lose Better
May 11, 2026
Slow and Steady Wins the Balance Sheet
May 04, 2026
Chamath is Still Dancing When the Music Stops
Apr 27, 2026
The Future of Investing is Lies
Apr 20, 2026
What's a Little Tax Lie Between Friends?
Apr 13, 2026
Private Credit is Hotel California For Your Money
Apr 06, 2026
What Are We Doing?!
Mar 30, 2026
Betting on Missiles is Not Investing
Mar 23, 2026
You Too Can Be a Sucker
Mar 16, 2026
SaaSpocalypse Now? AI, Block Layoffs & the Trust Premium
Mar 02, 2026
Pinterest: Hidden Gem or Just a Pretty Picture? [Investment Committee]
Feb 23, 2026
Is Software Dead or Just On Sale?
Feb 16, 2026
Finding Value Where No One Is Looking w/Lee Roach (author of The Value Road Substack)
Feb 09, 2026
Hi-Ho Silver, and Away
Feb 02, 2026
Got it Goin On Like Kroenke Kong
Jan 26, 2026
The 5-Minute Buffett Test
Jan 19, 2026
Play Stupid Games, Win Stupid Economies
Jan 12, 2026
CEO of Berkshire is a Job I'm Glad I Don't Have [2025 Greatest Hits]
Jan 05, 2026
Jim Beam Shuts Down, Tax Apps Block Holidays, and the $700M Wedding Ring Repo
Dec 29, 2025
Mitt Romney Says Tax the Rich? Plus Sports Betting Regret and Gen Z Financial Nihilism
Dec 22, 2025
Private Equity Invades College Sports: Utah’s $100M Gamble and Affordability is Broken
Dec 15, 2025
Michael Burry Speaks, Prediction Markets Explode, and Why TiVo Just Died
Dec 08, 2025
The Real Poverty Line, Ray Dalio’s Bubble Math, and Charlie Munger’s Last Lessons
Dec 01, 2025
Operating Margins, 4,000 Terrible Stocks & the Wild Google Comeback
Nov 24, 2025
20 Lessons from 2008 That Still Matter (Especially Now)
Nov 17, 2025
OpenAI is a Masterclass in Market Mispricing
Nov 10, 2025
A $20K Robot Butler and Why 57% of Americans Don’t Invest
Nov 03, 2025
How the NFL Prints Money, and Why College Tuition Just Crashed
Oct 20, 2025
AI Hype Circle, and ETFs Are the New Casino Chips
Oct 13, 2025
Japan, Debt, and the Downside of Free Money
Oct 06, 2025
Ponzi Nation — RadioShack Scams, First Brands Shenanigans & PE’s Retirement Heist
Sep 29, 2025
Robinhood’s New Private Fund Is a Terrible Idea
Sep 22, 2025
$300 Billion of Fake AI Money and the Oracle OpenAI Bubble
Sep 15, 2025
House Rich, Cash Poor: Why Americans Are Tapping Their Homes for Survival
Sep 08, 2025
Deckers Outdoor: Stock Turnarounds, Sheep Lawsuits & $11B Moonshots (Part 2)
Sep 01, 2025
Deckers Outdoor: From Surf Bums to a $30B Shoe Empire (Part 1)
Aug 25, 2025
ETF Survivorship Bias, Intel Drama, and the $1.3 Trillion Buyback Binge
Aug 18, 2025
Michael Mauboussin, PE Ratios & The Art of Future Value
Aug 11, 2025
South Park, Skinny Shots & the Market Meltdown
Aug 04, 2025
Ferrari Status & the Passive Investing Bubble
Jul 28, 2025
Passive Income Lies, BrewDog Drama, and Zip Code Economics
Jul 21, 2025
Youth Sports Are a $40B Racket — And Other Ways We Misallocate Money
Jul 14, 2025
Trump Accounts Debunked, PE Myths, and Incentivized Stupidity
Jul 07, 2025
Venture Returns Unpacked, AI’s Internet Disruption, And The Dangerous Success of Stablecoins
Jun 30, 2025
Stablecoins, Speculation, and When to Sell a 10X Investment
Jun 23, 2025
Circle IPO Frenzy, Tip Tax Madness, and America’s Adulting Crisis
Jun 09, 2025
[Replay] How the World’s Best Investors Stay Rich, Wise, and Sane | William Green Revisited
Jun 02, 2025
No Free Lunch — Tipping, Student Loans, and Complex Investing Truths
May 26, 2025
Leverage Looks Brilliant, Until It Blows Up
May 19, 2025
Is Warren Buffett Actually the GOAT?
May 12, 2025
McRecession, Doritos, and a Side of Disappointment
May 05, 2025
Yes Risk, No Rari (Yale’s $6B Sale, Student Debt Trouble, and YOLO Traders Gone Wild)
Apr 28, 2025
Who Owns America? Foreign Capital, China’s Strategy & the Private Equity Squeeze
Apr 21, 2025
Compounding When the World’s on Fire
Apr 14, 2025
I Tariff So Hard Economics Can’t Find Me (How Bad Math Crashed the Market)
Apr 07, 2025
Burrito Bowls, Now With Zero Percent Down
Mar 31, 2025
Preferred Shares of Chaos
Mar 24, 2025
Is America Really Going Bankrupt?
Mar 17, 2025
Rewriting the Economy: Trump’s GDP Plan, Market Crashes & a Shifting World
Mar 10, 2025
Booz, Buffett, and Billionaires
Mar 03, 2025
Bill Ackman’s Berkshire Bootleg
Feb 24, 2025
Bargains Gettin More Bargainy
Feb 17, 2025
What Have You Done For Me Bukelatley?
Feb 10, 2025
The Stocks From Ipanema Go Walking
Feb 03, 2025
Let’s Play Hide and DeepSeek
Jan 27, 2025
The Conundrum of the Personal Burger Taxi
Jan 20, 2025
Reading Between the Lines
Jan 13, 2025
Brought to You By the Year 2035 [2024 Episode Compilation]
Jan 06, 2025
Who is Buying This Hogwash?
Dec 30, 2024
First There Was the War, Then the Capitulation
Dec 23, 2024
Pop Goes the Bubble ‘Cause the Bubble Say Pop
Dec 16, 2024
While Your Feet Are Stomping And the Coins Is Pumping
Dec 09, 2024
Oh The Places Stocks'll Go
Dec 02, 2024
The Quest for Insufferable Geniuses w/ Josh Scott and Adam Burrows
Nov 25, 2024
Doogles Jumps the Shark
Nov 18, 2024
Curmudgeonry McMuffinry
Nov 04, 2024
Millennials Do Debt Better
Oct 28, 2024
Mr. Statman, Bring Me Some Risk
Oct 21, 2024
Unicorns, 10 Years Hence w/Aileen Lee (Founder of Cowboy Ventures)
Oct 14, 2024
Don't Let An Accounting Professor Run Your Company
Oct 07, 2024
David Tepper Just Don’t Care
Sep 30, 2024
Silly Yeltsin, Trix Are For Kids
Sep 23, 2024
Boyz II Men, ABC, BBD...Less Tax For Your Family
Sep 16, 2024
Rub a Dub Dub, Costco is Da Club
Sep 09, 2024
A Branded Tattoo, I’ll Always Have You
Sep 02, 2024
Some Guy On Some Other Job is Mr. Market
Aug 26, 2024
Confirmation Bias, And it Feels So Good
Aug 19, 2024
Warren’s Hoarding Cash and Putting Apple in the Trash
Aug 12, 2024
Will the Real Andy Grove Please Stand Up?
Aug 05, 2024
Pull Yourself Up By Your Pigtails
Jul 29, 2024
Wonk and Circumstance
Jul 22, 2024
The Skippyonaire Next Door
Jul 15, 2024
NYC’s $700 Million Schurprise
Jul 08, 2024
Walgreens’ Milkshake Brought No Investors to the Yard
Jul 01, 2024
Why’d You Have to Go And Make Things So Concentrated?
Jun 24, 2024
[Replay] Your Consumerism is Killing Me
Jun 17, 2024
My AI Juice Is Worth Your Squeeze
Jun 10, 2024
Get Your 10 Year Old to the Ballot Box
Jun 03, 2024
Hi-ho, the Derry-o, the Fama In the Dell
May 27, 2024
Google Has Gone Full Hooli
May 20, 2024
Chocolate’s Called Liquid Gold For a Reason
May 13, 2024
Skippy & Doogles Go To NewBraska
May 06, 2024
Debt La Soul is Dead
Apr 29, 2024
Pretty Ricky’s What They Call Him
Apr 22, 2024
Keep the Credit Where Credit’s Due
Apr 15, 2024
Tap That Social Security, Baby
Apr 08, 2024
Absolutely Never Always Use Absolutes
Apr 01, 2024
[Replay] The Market Has the Mouth of a Saylor
Mar 25, 2024
Six of One and 4000 Billion of the Other
Mar 18, 2024
Norway Or the Highway
Mar 11, 2024
It's Coal, It's Got the Juice
Mar 04, 2024
I Like to Be In America! For a Small Fee in America!
Feb 26, 2024
ETF Yields So Hiiiiiiiiigh, High Above Me
Feb 19, 2024
Choke the Woke, End Up Broke
Feb 12, 2024
Smart Money Bets on Liberty Biberty
Feb 05, 2024
Housing is a Lens Into Civilization w/ Conor Dougherty (author of Golden Gates)
Jan 29, 2024
Celebrating That Rent-a-Center Culture
Jan 22, 2024
Dat Money Be Gone
Jan 15, 2024
Running 5Ks Does Not An Investor Make [2023 Episode Compilation]
Jan 08, 2024
Bird Bird Bird, the Bird Ain’t the Word
Jan 01, 2024
When They Move, We Move, Just Like That
Dec 25, 2023
Rich Elon, Poor Elon
Dec 18, 2023
All You Can Eat Debt Buffet
Dec 11, 2023
Feeling That Munger Hunger
Dec 04, 2023
Junk Bonds Got the Yields to Make Your Booty Go Smack
Nov 27, 2023
I Do Not Like It Sam I Am
Nov 20, 2023
Just Stop, Dave Ramsey
Nov 13, 2023
Ye And His Adidas Do the Illest Things
Nov 06, 2023
Free Will(y)
Oct 30, 2023
Snitches Get Riches
Oct 23, 2023
Slimmer Waistlines, Slimmer Returns
Oct 16, 2023
Impendio Infinitus
Oct 09, 2023
For the Love of the Fat Bears
Oct 02, 2023
Government Does Itself No Favors
Sep 25, 2023
Would a Stock Without a Dividend Earn As Sweet?
Sep 18, 2023
Indebted and Fretted
Sep 11, 2023
Getting My Stock Tips At Auntie Anne’s
Sep 04, 2023
SPAC’d In the Face With Reality
Aug 28, 2023
When I Rich, You Rich, We Rich
Aug 21, 2023
A Mighty Big Bite of the Apple
Aug 14, 2023
Retire? I Don’t Even Know Her!
Aug 07, 2023
Seeing the World Through Yellow Colored Glasses
Jul 31, 2023
We Will All Be Robots Soon
Jul 24, 2023
TayTay Day
Jul 17, 2023
Gotta Lose Money to Make Money
Jul 10, 2023
Things Are Going South
Jul 03, 2023
The Billionaire Death Match
Jun 26, 2023
Nuggets of Wisdom
Jun 19, 2023
When Puts Comes to Shove
Jun 12, 2023
All Hail the Salvatious Seven
Jun 05, 2023
From the Pub to Your Ear Buds
May 29, 2023
Scurry Burry Investing Up a Flurry
May 22, 2023
Mungermania LVIII
May 15, 2023
No Pain, No Premium
May 08, 2023
I Feel REITs In My Fingers, I Feel REITs In My Toes
May 01, 2023
One Way Ticket Out of Pity City
Apr 24, 2023
Turning Kohl's Into Diamonds
Apr 17, 2023
No Work And All Play Makes Jack A Dull Boy
Apr 10, 2023
Two Good Friends and a Microphone [Seafarer Investor Podcast Interview]
Apr 03, 2023
Stay In Your Lane, Liam Neesons
Mar 27, 2023
Why Can't Banks Just Be Normal?
Mar 20, 2023
You Down Wit SVB? Yeah FDIC!
Mar 13, 2023
America’s Got 99% Problems And Housing Is One
Mar 06, 2023
Fees, Sir, I Want Some More
Feb 27, 2023
Munger Don’t Care About You Or Anything That You Do
Feb 20, 2023
Beware the Sharknado Recession
Feb 13, 2023
Johnny Needs a Fast Car
Feb 06, 2023
Simply the Best, Worse Than All the Rest
Jan 30, 2023
Fantastical Rates and Where to Find Them
Jan 23, 2023
I Left My Wallet in El Tokyo
Jan 16, 2023
Office Space is a Comedy, Not a Blueprint [2022 Episode Compilation]
Jan 09, 2023
Closing Out An Eggstraordinary Year
Jan 02, 2023
Bow Knows This And Bow Knows That
Dec 26, 2022
Deion Sanders Up In China
Dec 19, 2022
The Pied Piper of New York City
Dec 12, 2022
Little Caesars is Dead, Long Live Little Caesars
Dec 05, 2022
You Gotta Spend Money to Spend Money
Nov 28, 2022
The SEC Doesn't Regulate Poop Emojis
Nov 21, 2022
Angela Lansbury Would Be Disappointed
Nov 14, 2022
Welcome to the Janet Jackson Market
Nov 07, 2022
It's Cool to Be Kind w/ W. David Marx (author of Status and Culture)
Oct 31, 2022
Sideways Markets From Wayside School
Oct 24, 2022
Wood You Mind Slowing Down?
Oct 17, 2022
Can You Keep Up? FDR Make Me Lose My Breath
Oct 10, 2022
Housing Be Beamin' While the Market's Screamin' Lehman
Oct 03, 2022
Weak Ties, Strongly Held
Sep 26, 2022
Peloton is the Jim Cramer of Companies
Sep 19, 2022
Interest Rates Are Up…But Not For Your Savings
Sep 12, 2022
It's Not Right, And It's Not OK
Sep 05, 2022
It’s APE’s World, We Just Live In It
Aug 29, 2022
Out of the Frying Pan, Into the Prison
Aug 22, 2022
Playing Hot Potato With Dynamite
Aug 15, 2022
The Predictive Power of Trousers and Trainers
Aug 08, 2022
TINA and TASA in a TUSSLE
Aug 01, 2022
The Value In Preparation w/ William Green
Jul 25, 2022
Powell, Just Get On With It Already
Jul 18, 2022
Post Malone Saves the Metaverse
Jul 11, 2022
Is Radio Shack the Next Berkshire Hathaway?
Jul 04, 2022
Dear Bitcoin, Do You Know How Hedges Work?
Jun 27, 2022
The Market Has the Mouth of a Saylor
Jun 20, 2022
When Bees Are Fish, No Portfolio Is Safe
Jun 13, 2022
Don't Slap Grandpa at Costco
Jun 06, 2022
Blue Chips and Red Crackers
May 30, 2022
If Being Rich is Sexy, Getting Rich Sure Isn't
May 23, 2022
Numbers Don't Matter in Canada
May 16, 2022
Sticking Through Thick and Thin w/ Justin Carbonneau (Validea Capital Management)
May 09, 2022
This Never Happens, Except All the Time
May 02, 2022
Blame It On the P-p-p-p-p-password Sharing
Apr 25, 2022
A Twitter By Any Other Price Would Smell More Sweet
Apr 18, 2022
Bill Gross' Extraordinary Playlist
Apr 11, 2022
Between a JPEG Rock and a Hard Place
Apr 04, 2022
America's Self-Induced Filibuster
Mar 28, 2022
One Large Popcorn, Light on the Gold Please
Mar 21, 2022
I'll Give You $100K for That Nickel
Mar 14, 2022
Your Cash is No Good Here
Mar 07, 2022
Our Hearts Are With Ukraine
Feb 28, 2022
Inspector Gadget Hacks Bitcoin
Feb 21, 2022
Tesla, the King!
Feb 14, 2022
Peeps Be Done Gone Crazy
Feb 07, 2022
I Can Has Sweden?
Jan 31, 2022
Calm Down Chicken Little
Jan 24, 2022
I Feel Tippy, Oh So Tippy
Jan 17, 2022
Nonsense and Glory [Your 2021 Favorites]
Jan 10, 2022
Confusing Buffett, Bernie and Orville
Jan 03, 2022
What a Difference a Year Makes
Dec 27, 2021
Who Moved My Cream Cheese?
Dec 20, 2021
Metaversially Controversial
Dec 13, 2021
Some Turkey With a Side of "Audio Issues"
Dec 06, 2021
ARKK You Kidding Me Right Now?
Nov 29, 2021
Never Underestimate Florida Man
Nov 22, 2021
Your Consumerism is Killing Me
Nov 15, 2021
Tesla vs. the World
Nov 08, 2021
Zuck is Officially Off His Rocker
Nov 01, 2021
The DWAC SPAC is BACK
Oct 25, 2021
NIMBY, NIMBY Everywhere
Oct 18, 2021
Hips Don't Lie, But Bank Accounts Do
Oct 11, 2021
Nancy Pelosi, Queen of the Markets
Oct 04, 2021
A Future of Negative Interest Rates w/ James Mackintosh (Wall Street Journal)
Sep 27, 2021
Narratives Up, Facts Down
Sep 20, 2021
A Broken Market is Still Right Twice a Day
Sep 13, 2021
Sorry, Jenna, Maybe This NFT Will Help
Sep 06, 2021
Investing in the Fashion Metaverse
Aug 30, 2021
Hedgehogs, Foxes, and Woods — Oh My!
Aug 23, 2021
TINA Scouts Out Some Mobile Homes
Aug 16, 2021
Buying is Easy, Selling is Harder
Aug 09, 2021
Credit Suisse And the 1000x Rounding Error
Aug 02, 2021
Nonprofit Stocks Are All the Rage
Jul 26, 2021
Don't Trust Teenagers With Your Bitcoin Money
Jul 19, 2021
Like a Bear in a China Shop
Jul 12, 2021
A Dollar, A Dollar, My Kingdom For a Dollar!
Jul 05, 2021
Delawarean Gumption Moves Markets
Jun 28, 2021
Give Me All Your Inflation, Give Me All Your Debt
Jun 21, 2021
Bukele vs the Volcano
Jun 14, 2021
To Cow or Not to Cow, That is the Question
Jun 07, 2021
Skippy Becomes a Lumberjack
May 31, 2021
Investing Where You Have An Edge w/ Adam Burrows (Managing Partner, Range Ventures)
May 24, 2021
Blissfully Wasteful Car Wrecks
May 17, 2021
Compounding Goodwill w/ William Green (author of Richer, Wiser, Happier)
May 10, 2021
All Your Debt Are Belong to Us
May 03, 2021
Let's Talk About Tax, Baby
Apr 26, 2021
The Profitability of Unprofitability
Apr 19, 2021
Hot Takes From the Dimons and the Damons
Apr 12, 2021
Biden's Comin' in Hot!
Apr 05, 2021
Can't Drive? Blame the Wind
Mar 29, 2021
On the Path to a SPACtacular Disaster
Mar 22, 2021
An Ode to Excel
Mar 15, 2021
Who is talking about Ford Motor Company?
Mar 08, 2021
Redistribute the Bubble
Mar 01, 2021
The Case of the Cryptic Crypto
Feb 22, 2021
HVAC is the New Black
Feb 15, 2021
Brady and Buffett Walk Into a Bar
Feb 08, 2021
GameStop Keeps Printing Tendies
Feb 01, 2021
The Search for the Deep Cheap
Jan 25, 2021
The Harbaugh Fire Sale
Jan 18, 2021
Will the Real Jack Ma Please Stand Up?
Jan 11, 2021
No one's ever gone wrong by buying a Chinese stock
Jan 04, 2021