This is Matt Reustle. Today we are breaking down Duolingo, the learning app built on language learning that is increasingly expanding into other territories like math and music. Founder Luis von Ahn is constantly looking for ways to make this accessible and free to use for people all around the world while simultaneously finding reasonable ways to monetize a ... Show More
May 29
Toast: Sticky SaaS - [Business Breakdowns, EP.247]
Today, we are breaking down Toast, a name we have covered before but are revisiting because the story has changed enough to be worth telling again. Most listeners will have tapped a Toast terminal without thinking much about the business behind it. Our guest is Sean Barrett, foun ... Show More
49m 24s
May 15
Auto1: EU-sed Car Marketplace - [Business Breakdowns, EP.246]
Today, we are breaking down Auto1, and this is an interesting episode because we are tackling a business that most US listeners will not be familiar with, even though it resembles names they already know well. Our guest is Harrison Moot, co-founder and CIO of Sandstone, who walks ... Show More
1h 5m
May 8
Opendoor: Q1 2026 Earnings - [Business Breakdowns, EP.245]
Today, we are breaking down Opendoor, and this is a unique episode. We recorded with Kaz Nejatian, the CEO of Opendoor, shortly after the company reported its first quarter 2026 earnings, and we covered both what is happening inside the business right now and how he is thinking a ... Show More
25m 34s
Dec 2024
TIP680: Investing in Exceptional Businesses for the Long Run w/ Dev Kantesaria
On today’s episode, Clay is joined by Dev Kantesaria to discuss the current market environment, the types of investments he is looking for, FICO, S&P Global, and much more. Dev is the founder and portfolio manager at Valley Forge Capital Management. The firm has been highly succe ... Show More
58m 21s
Nov 2024
Why Duolingo Worked (with Luis von Ahn, CEO)
Duolingo has fundamentally changed the landscape of self-guided education, starting with language learning. It is now a $9B publicly traded company in a space where everyone thought you could never build a large and exciting company. We’re joined by Duolingo founder and CEO, Luis ... Show More
1h 3m
Mar 2024
Anthony Pompliano: Investing, Operating and Distributing - [Making Markets, EP.20]
My guest this week is the Anthony Pompliano, better known as Pomp. Pomp is an investor, entrepreneur and one of the biggest media personalities in the world of crypto. In today's conversation, we talk about Pomp’s early career, his evolution as a capital allocator, and how he vie ... Show More
1h 1m
Oct 2025
TIVP043: MSCI (MSCI): The Financial Giant Enabling Passive Investing w/ Shawn O’Malley & Daniel Mahncke
Shawn O’Malley and Daniel Mahncke break down MSCI Inc. (MSCI), the global leader in financial market indexes that power the passive investing revolution. They explore how MSCI built its dominant, utility-like business model, its compounding potential, and whether the stock remain ... Show More
1h 12m
Aug 2025
176. Chamath's New SPAC (Detailed Breakdown) Plus Europe’s Yield Curve Warning
Send us Fan MailThis week on The Skinny on Wall Street, Kristen and Jen dive into the resurgence of SPACs and yes, Chamath Palihapitiya, the once-dubbed “SPAC King,” is back with a brand-new deal. We unpack what a SPAC really is, why they exploded in 2020, changes in the new stru ... Show More
46m 31s