S2E23: Building Paid: $31M Raised on Confidence, Not Fear (Manny Medina, Raj Dosanjh)

Manny and Raj sit down over a scotch to celebrate closing Paid's $21M seed round at a valuation between $100-200M, just 10 months after starting the company in an Airbnb with four people. This is the most candid conversation yet about what it actually takes to build a company at breakneck speed in the AI era. They unpack why Manny took a high valuation he's confident he can deliver on, how they closed the round with a 60% working demo, and why Raj moved from India to London despite living like a king. Manny and Raj get honest about the cultural foundation we’ve built between seed and Series A, the arguing that nearly tore cofounders apart, and why they're done optimizing for the next round. They discuss forward deployment tactics borrowed from Palantir, why engineers don't need product managers, and the difference between playing for market share versus wallet share. Cofounder Manoj crashes the recording to share why he left retirement after two days of not being able to stop thinking about Paid's mission. This is the story of building with conviction, abundance mindset, and the belief that winning is the only metric that matters.