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

Manny and Raj sit down to celebrate closing Paid's $21M seed round just 10 months after starting the company in an Airbnb with four people. This is your inside look yet at what it takes to build a company at AI speed. 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 the fuckton of arguing that almost tore the cofounders apart.

The valuation question

"I can sell 100 million of anything. So I'm not scared of 100 million. If the evaluation was 300 or like 250, I would be super scared. 100, I can sell 50, I can sell 100 of whatever. I'm not scared of that number."

Manny explains why they took a valuation between $100-200M when everyone warned them it was too high. Sales is a game of confidence. He didn't have the confidence for higher, but he's not scared of this number. They got the term sheet when their product was half demo, not more. The key insight is knowing which bar you can actually clear.

From fear to winning

The shift from Outreach to Paid represents a fundamental mindset change. At Outreach, survival mode drove every decision. At Paid, with $31M in the bank ($10M pre-seed + $21M seed) for 11 people, they have time to design the future they want to build. Raj shares how his last startup died because he avoided fighting. Now he's learned that hard conversations with experienced cofounders create purer relationships. Manny reveals the marriage lesson that changed everything: give each other grace, walk away when heated, and come back to the same problem with fresh perspective and no assumptions. Be a goldfish. Have a shorter memory on the shit that bothers you.

The Palantir playbook

Raj brings forward deployment to Paid. Every single one of the engineers has been deployed to customers and nobody died. The traditional setup has customer research, product managers talking to customers, feeding devs tickets. That's incredibly low bandwidth. An engineer being there, talking to customers, contains everything in their head with zero information loss. Big secret: engineers can talk to people. They can figure this out. They don't need to be locked in a cupboard.

Why Winning Is The Only Metric

Raj doesn't consider the time somebody spends building something as precious. He considers winning precious. Getting a customer precious. The time you take to iterate is just reps. At Outreach, they considered developer time the most valuable thing. In reality, winning is the most valuable thing. This creates different behavior. When team member Atta volunteered to redeploy customers from three months ago because the technology is significantly better now, Manny knew they had something special. No public company does that. Salesforce, ServiceNow, Workday give you code to get you over the line and you're stuck with it. They don't give a fuck about you. Paid operates from duty and pride, like a doctor with a Hippocratic oath. We found new science and we're going to give it to you whether you like it or not.

The UK vs US Mindset

Raj from Coventry gets asked by school friends: why are you doing this when you had such a good job? Manny nails the difference between US and UK entrepreneurship. In the US, people celebrate the ability to sell your way into financial independence and doing whatever you want with your life. Why is getting a job the bar for a university student? How about starting something? Making money? Financial independence? The UK has a class system and a culture where it's not cool to be successful. You want to be like everyone else, not upper class.

But Raj sees Paid as a mechanism to get Britain building again. Not cars, that ship sailed to China. But in a world where you can talk to an AI and it builds something, if you have a real problem, you have the opportunity to sell it. The positive vision of AI versus the dystopian version that robs everyone of agency.

Between Seed and Series A Is Everything

"Whatever you did in the between seed and A is what you're locking in. That's a time of defining how straight the tree is gonna grow. If you ended up crooked, just to put points on the board, and you try to grow crooked by putting more points on the board, you screwed it."

Not quid pro quo deals, everyone does that. It's about sales efficiency, technical debt, operational debt, culture in general. Are you devoting enough time to getting it right? Culture is like being a gardener. Making sure the soil is ready, pulling weeds, giving plants water and sun so they grow. Eventually you step back from fighting and make sure your garden is flourishing.

That's leadership.

Companies Mentioned

• Paid
• Outreach
• Palantir
• Salesforce
• ServiceNow
• Workday
• Replit

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