Building Outreach to a $4bn unicorn and helping AI agents get paid with Paid.ai - Manny Medina, Co-Founder & CEO @ Paid.ai

This week on Riding Unicorns, we’re joined by Manny Medina, the visionary founder behind Outreach — the $4B sales engagement unicorn — and now co-founder & CEO of Paid.ai, a startup pioneering how AI agents get priced, paid, and scaled. We dive into Manny’s remarkable journey from zero to $250M+ ARR with Outreach, the gritty early days of selling door-to-door with no cash, and how he turned that experience into a masterclass in category creation. Now, with Paid.ai, Manny is laser-focused ...

Om Podcasten

Riding Unicorns is the go-to podcast for anyone interested in venture capital and high-growth startups. Hosted by VCs James Pringle and Hector Mason, the show explores what it takes to build and back successful tech unicorns.Each episode features candid conversations with top founders, operators, and investors—unpacking the strategies, challenges, and insights behind scaling category-defining companies. From fundraising and product-market fit to hiring, growth, and beyond, no topic is off-limits. Whether you're a founder, VC, angel investor, or just curious about the world of startups, you’ll find valuable takeaways in every episode.