Riding Unicorns: Venture Capital | Entrepreneurship | Technology · Riding Unicorns Productions

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

September 17, 2025·49 min·2 clips

Agents do human work, but your pricing model still assumes humans.

Manny Medina joins Riding Unicorns as the founder of Paid.ai and previously the founder and CEO at Outreach, and maybe now in an executive chairman role. The conversation starts by defining an agent as software that does work autonomously and can replace a human task without needing human intervention, which sets up the commercial question behind Paid.ai. Medina explains that the idea for Paid.ai came out of building agents at Outreach, where the software was already doing more work than the seed monetization model was built to handle. He frames the company as part of the plumbing for an agentic era, where autonomous systems still need a way to be priced, tracked, and paid. The host keeps pulling the thread back to practical startup mechanics. Medina is pushed to explain what stage the business is really in, what milestones matter, and how investors should think about deploying capital. That shifts the talk toward people, products, and the order of operations inside an early company. He argues for more investment in product than growth at the beginning, with the idea that durable growth comes from building something genuinely useful and understanding the customer problem first. The conversation is blunt about premature spend. A Times Square ad buy may be funny in theory, but not if the company is still figuring out its real advantage. Medina also walks through the idea that funding is a result of hitting milestones, not the milestone itself. Revenue sits underneath that thinking. The point is not simply to raise again, but to prove that the business solves something customers will pay for. Throughout, the interview stays conversational and founder-led rather than polished or academic. Medina uses experience from Outreach and Paid.ai to ground abstract AI talk in the realities of sales, monetization, and company building. The result is a discussion that moves easily between technology and operating discipline. It leaves room for enthusiasm about agents without pretending the commercial layer has been solved. It also makes clear why pricing and payment infrastructure matter if agents are going to become standard work tools. Listeners get a clear look at how a seasoned founder thinks about the next platform shift. They also get a practical reminder that good product work still outruns hype when the business is young.

As heard by us

The sharpest thread is how agents get priced and paid, not just how they work.

The episode centers on a real business problem behind agent software: if software is doing human work autonomously, how should it be priced and paid for?

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Why you'd press play

See how Outreach founder Manny Medina thinks about how AI agents get priced and paid for.

Read the full recommendation in PlayNext →

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