Monopoly, every mention
42 scenes across 17 shows · ← back to Monopoly
tap a year for its mentions
Capital Allocators 11
20VC 6
How I Built This 5
My First Million 5
Founders 5
Acquired 3
the Y Combinator Startup Podcast 2
the Knowledge Project 29 more shows
every year every show Capital Allocators 11 20VC 6 Founders 5 My First Million 5 How I Built This 5 Acquired 3 the Y Combinator Startup Podcast 2 the Knowledge Project 2 
Big Technology 2 
Another Podcast 1 
Startups For the Rest of Us 1 
the Startup Ideas Podcast 1 
WTF is with Nikhil Kamath 1 
Invest Like the Best 1 
Sourcery 1 
the a16z Podcast 1 
TBPN 1
Verbatim, from the transcripts: passages where Monopoly comes up on Capital Allocators, 20VC, Founders, My First Million, How I Built This
Claude Fable 5 is BACK
- ▶ 0:10 Greg Isenberg I mean, I've seen some crazy examples on X of people one-shotting like a Monopoly game, and that's really cool, but how could I use this super intelligence and just point it to different problems to make me money and be more productive?
Brian Singerman: "If SpaceX Didn't Work, Founders Fund Wouldn't Exist" · Sourcery with Molly O'Shea
- ▶ 3:13 Brian Singerman Anything from Monopoly to Acquire to, you know, any of the old games, and I just got really super into it.
Legendary Trader Paul Tudor Jones on AI Risk, Bubbles and Buffett · Invest Like The Best
- ▶ 49:35 Paul Tudor Jones I, I loved chess, backgammon, Parcheesi, Monopoly, ah, Battle, um, Gin Rummy, you name it, I played it.
Jeremy Grantham – Bubbles, Value Investing, and the Long Game at GMO (EP.493)
- ▶ 9:10 Jeremy Grantham I grew up playing Monopoly seriously, checking off numbers with a little roulette wheel while pretending to watch games of cricket that went on forever.
- ▶ 1:03:13 Jeremy Grantham That was the big turn on for me, thinking of ways to play this game, this monopoly, this complicated thing, and try and work out what made it tick and what could help you outperform.
17 Young Founders | 8 Startups | 20 Lakh Grants | Third WTFund Cohort · Nikhil Kamath
- ▶ 1:23:38 Nikhil Kamath Think of the world as a game of monopoly.
Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
- ▶ 1:12:24 Rory O'Driscoll You remember the monopoly card?
Exploding Kittens: Elan Lee. How cat-themed Russian Roulette changed game night forever
How Bill Gates Works
- ▶ 6:50 David Senra So monopoly risk card games.
Adrian Meli – Active Equity Excellence at Eagle (EP.459)
- ▶ 7:31 Adrian Meli That was growing up and all the games we played growing up were monopoly and acquire.
a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
OpenAI Raises $40 billion, Is AI a Letdown?, Musk Sells X to xAI
- ▶ 55:48 Alex Kantrowitz It's like using Monopoly money to buy Pokemon cards. 2 times in the scene
Indian Premier League Cricket (Audio) · Acquired
- ▶ 2:09:46 David Rosenthal It turns it into a monopoly game.
The END of LUXURY GOODS? (Trump’s Tariffs)
- ▶ 14:46 John Coogan It was like a game of Monopoly.
Striking Oil – CrownRock by Lime Rock Capital (EP.428)
- ▶ 1:04:26 Jonathan Farber I am the 19 to 86 Connecticut Monopoly champion. 2 times in the scene
The Richest Woman In America: Hetty Green
- ▶ 45:03 David Senra This, this jumped out to me because I grew up playing monopoly and I loved buying the railroads.
David Morehead – Top Down Allocation at Baylor (EP.381)
- ▶ 6:53 David Morehead Growing up, my favorite board game was Monopoly.
What I learned from having lunch with Sam Zell
- ▶ 29:47 David Senra And that book is Zeckendorf, the autobiography of the man who played a real life game of monopoly.
- ▶ 1:11:27 David Senra Around the same time, uh, I had read the book Zeckendorf, the autobiography of the man who played a real-life game of Monopoly and won the largest real estate empire in history.
Episode 701 | The Long Journey to Product-Market Fit
- ▶ 15:43 Matt Wensing Meaning it's, I like to say it's the Baltic Avenue of the Monopoly board.
Tom Gayner: Invest Like The Best
- ▶ 1:00:34 Tom Gaynor And, um, when it came time to pay for it, he paid with monopoly money.
Guillaume Cabane: Why Your First Growth Hire Should Be a Former Founder | E1088 · 20VC with Harry Stebbings
- ▶ 1:00:25 Harry Stebbings I've played Monopoly. 2 times in the scene
Sam Zell's Autobiography
- ▶ 37:45 David Senra I read the book Zeckendorf, the autobiography of the man who played a real-life game of Monopoly and won the largest real estate empire in history.
Jerry Colonna: The CEO Whisperer
- ▶ 38:10 Jerry Colonna They could win the game of monopoly.
The magic customer
- ▶ 38:35 Leonard Brody It was like, it was literally like monopoly money, and you would bring it back and pay with it.
How To Grow A Small Agency Into A Billion Dollar Company (#414)
The Secrets To Setting Smarter Goals · Y Combinator
- ▶ 23:56 Dalton Caldwell It's like, we're not playing Monopoly.
Saas Companies that Anyone Can Start with Rob Walling
- ▶ 36:06 Rob Walling So it's like not like a board game is Monopoly, right?
Spin Master/PAW Patrol: Ronnen Harary
Standard Oil Part I · Acquired
- ▶ 1:20:55 Ben Gilbert I think that's on a Monopoly board.
- ▶ 1:20:57 David Rosenthal It is literally on a Monopoly board.
MFM #165: How Jack Butcher is Selling his Art for $76m & How to Research Wealthy People
- ▶ 19:40 Shaan Puri It's not like saying, um, Monopoly. 2 times in the scene
MFM #163: How Chrome Plugins Are Making Millions & How A Studying App is Going Viral
- ▶ 31:07 Shaan Puri And if you get it right, it's like the monopoly game at McDonald's where you actually earn the Bitcoin.
Remembering Tony Hsieh of Zappos
- ▶ 15:56 Tony Hsieh And so I ended up one by one selling off the apartments and it's kind of like when in Monopoly, when you, you buy a hotel or houses
Kevin Hale - How to Evaluate Startup Ideas · Y Combinator
- ▶ 17:59 Kevin Hale And so we don't mean this in the, ah, monocle, monopoly game sense.
20VC: Justin Kan on Why We Have To Normalize Vulnerability in Startups Today, Why Attaching Happiness To Future Outcomes Will Only Lead To Suffering & Why It Is Total BS That You Have To "Suffer" When Doing A Startup
- ▶ 18:52 Justin Kan Talking about one of these, you know, fancy German board games, like settlers of Catan or something, not monopoly, but you're really trying to engage, be engaged in winning and you want to win and you try your hardest.
Zappos: Tony Hsieh (2017)
- ▶ 16:51 Tony Hsieh And, uh, and basically, as Zappos was growing, it was also losing more money, and we also need more money for inventory, and so I ended up, one by one, selling off the apartments, and it's kind of like when in Monopoly, when you, you buy a…
Brent Beshore - Micro Buyout Adventur.es (Capital Allocators, EP.79)
- ▶ 5:50 Brent Beshore I guess Monopoly has kind of a mixed reputation, but I was just, I dominated at Monopoly growing up. 3 times in the scene
Brian Portnoy – From Complex to Simple (Capital Allocators, EP.57)
- ▶ 59:40 Brian Portnoy And we're not talking Candyland or even Monopoly. 2 times in the scene
The Future of Money: Banking on Fintech
- ▶ 11:53 Alex Rampell So, ah, it took Lending Club a while to kind of catch on, and you'll notice that almost all these players are in the lending space, because again, the difference between a depository institution and a lending institution is, ah, does…
Zappos: Tony Hsieh
- ▶ 14:21 Tony Hsieh And, uh, and basically, as Zappos was growing, it was also losing more money, and we also need more money for inventory, and so I ended up, one by one, selling off the apartments, and it's kind of like when in Monopoly, when you, you buy a…