The Investor + Operator (IO) Podcast
The Investor + Operator (IO) Podcast hosts the most candid, applicable conversations about building companies with the world’s best operators and investors.
Brought to you by Pelion Venture Partners
Recent Episodes
Sept. 30, 2025
Zero To $1 BILLION In Payments In Just One Year: How To Crush Product-Market-Fit w/ Joshua Silver
Usually small startups fail when trying to take on big companies. Rainforest, however, is a different story. In the payments space dominated by Stripe and PayPal, founder Joshua Silver saw a gap no one was paying attention to...
Sept. 16, 2025
$500M Founder: Avoid These Critical Mistakes When Competing With Incumbents - A convo w/ 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: C...
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 Me...
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 episode. 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 o...
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 shar...
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 B...
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