Jan. 5, 2026
How This Billion-Dollar CEO Judges Success
Videos
Dec. 16, 2025
Why The Second Decade Is The Best For Startups — A convo w/ Spenser Skates, CEO Amplitude Analytics
In today's episode, Tyler and Sterling sit down with Spenser Skates, Founder and CEO of Amplitude Analytics, the digital Analytics platform that helps thousand of businesses find ways to grow and improve. Spenser shares how he got his first investors, how to have the best relationships with VCs, his mindset…
Oct. 14, 2025
Ex Navy SEAL: When To Quit Vs Persevere In Business + How I Started A Successful Venture Firm!
A question every startup founder has is, "When do I know when to keep going or throw in the towel?" Today, Tyler and Sterling sit down with ex Navy Seal and Olympian, Larsen Jensen, to talk about just that. Larsen is the founder of Harpoon Ventures, an investment firm focused…
Oct. 3, 2025
This Startup Went From $0 To $1 BILLION In A Year
Watch the full episode on the IO Podcast
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. The result? Over $1 Billion in transactions in their first year! In…
Sept. 21, 2025
How This $500M CEO Got His First 10 Customers
Watch the full episode on the IO Podcast
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…
