Sept. 16, 2025
How Startups Beat Incumbents
Watch the full episode on the IO Podcast
Videos
Sept. 16, 2025
$500M Founder: Avoid These Critical Mistakes When Competing With Incumbents -Daniel Simon, Coast CEO
Are you a small startup trying to compete with the big dogs? Well then this episode is for you. Tyler and Sterling sit down with Daniel Simon, co-founder of Bread (sold for $500M) who is now working on his next big startup: Coast, a fuel card and payment platform for…
Sept. 2, 2025
Kapital: The Future of Latin-American Banking With Mexico’s Best Startup
If you need some motivation as an entrepreneur, then this is the podcast episode for you. In today's video Tyler and Sterling sit down with Rene Saul, the CEO and co-founder of Kapital, the $1.3 billion-dollar startup from Mexico City that is transforming the Latin-American banking space forever. Rene breaks…
Aug. 22, 2025
Tips on Fundraising from a Multi-Billion-Dollar CEO
Watch the full convo on the IO Podcast
Aug. 18, 2025
The Secret $170M ARR Business NOBODY Knew About
Watch the full convo on the IO Podcast
Aug. 14, 2025
How Property Solutions became Entrata (and worth $4.5B)
Watch the full convo on the IO Podcast
Aug. 12, 2025
Lessons From Building Utah's Next $10B Company — A convo w/ Adam Edmunds, CEO of Entrata
If you haven't heard of Entrata yet, then you need to listen to this. Entrata is a sleeping giant of a company that has quietly been growing in the background...and is on track to be the biggest company to ever come out of Utah. In this episode, Tyler and Sterling…
July 29, 2025
Leading a $1B Revenue Startup AND $1.8B VC Firm – A convo w/ Arjun Sethi (Tribe Capital + Kraken)
Hands-down, Arjun is the most interesting man in venture capital. He thinks differently than everyone else, and as a result, his VC Firm, Tribe Capital, and his startup, Kraken, are completely unique. In this episode, he shares how he got started, and the exact tools he used to get where…
July 21, 2025
Should startups raise money in the age of AI?
Watch the full podcast here: https://youtu.be/GwLPQpI-kHE
July 18, 2025
What startups need to raise their series A
Watch the full podcast here: https://youtu.be/GwLPQpI-kHE
July 16, 2025
NEVER do this when pitching your company
Watch the full podcast here: https://youtu.be/GwLPQpI-kHE
July 15, 2025
How The BEST Founders Go From Seed To Series A - a convo w/ Brett Berson of First Round
What are the questions founders and VC firms should be asking when raising a Series A? How will AI impact things? What are the common pitfalls for Seed-stage startups? In this episode, Tyler and Sterling sit down with Brett Berson of First Round Capital to answer all these questions and…
June 19, 2025
How should you think about choosing and pitching investors as a startup founder?
If you're a founder/entrepreneur, watch the full episode here: https://youtu.be/3U0qgIdYCQU