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 on building the financial stack that will power the next wave of autonomous agents — and helping AI-native businesses build real, durable revenue.

🚀 In this episode, we cover:

🧠 What an AI Agent really is — and why it changes everything
💸 Why the old SaaS pricing models don't work for agent-native businesses
📊 Outreach’s year-by-year revenue climb — and how they avoided collapse
🪙 Why durable growth matters more than fast growth
🔥 How Paid.ai is redefining payments, margin tracking, and monetisation for agents
🛠️ Building new infra for a world where humans no longer press the buttons
📈 Creating categories — and why most startups get it wrong
⚠️ Why many startups confuse market pull with product genius
👀 Insights into retention challenges at tools like Lovable, Cursor, and Bolt
💰 Manny’s fundraising advice — why sometimes raising less is more dangerous

Manny is one of the most respected builders in SaaS and now sits at the bleeding edge of the agentic future. If you’re building with agents, selling B2B, or navigating a shift from software to automation, this is a must-listen.