Startupable

The outsider’s guide to Silicon Valley. I came here as a foreigner to learn what truly sets the best apart: the decisions, strategies, and mindsets that outsiders often see more clearly than insiders. Each week, I go deep with founders, investors, and operators to uncover the real reasons behind their success. Past guests include the founders of Vercel, Auth0, Nubank, Mercado Libre and Kavak.

  1. I Built a $4.4B SaaS and AI Agents Destroyed It: The End "Per Seat" Pricing

    12/10/2025

    I Built a $4.4B SaaS and AI Agents Destroyed It: The End "Per Seat" Pricing

    My guest today is Manny Medina, the founder who defined the last decade of sales tech with Outreach and is now building Paid.ai , the infrastructure for the next decade of AI. Manny’s path took him from a shrimp farm in Ecuador to the heights of Silicon Valley, where he built Outreach into a $4.4B SaaS. But in 2023, a conversation with the CEO of DocuSign handed Manny a "Red Pill" moment: if AI agents do the work of humans, companies will hire fewer people, and the seat-based SaaS model will collapse . He realized the current infrastructure—giants like Salesforce, Netsuite, and Datadog—was "conspiring against him." They could track closed deals or API calls, but they couldn't distinguish between an agent's cost (tokens) and its value (reasoning) .  Manny founded Paid to solve this: a way to interpret agent behavior so builders can stop selling cheap software and start selling valuable work. Paid has raised +$30M from investors like Sequoia, Lightspeed and EQT. What we covered Why the Agent Economy is impossible without a new metering layer Why seat-based pricing is dead and what replaces it Why generalist agents lose to specific domain expertsHow the tech recession forced Outreach to reinvent itself GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER 🗞️ Read it: https://rebrand.ly/tssnwsrss Marcelo's LinkedIn: https://www.linkedin.com/in/marcelocamberos/ Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/ Do you want AI powered productivity? Get 3 Months Free of Notion: Business Plan + Unlimited AI 👉 https://rebrand.ly/NTNENGYTR3

    48 min
  2. 11/13/2025

    $1B Founder: "AI Voice Infrastructure Doesn't Exist Yet" Here is Why That's $10B Opportunity

    My guest today is Marcelo Camberos, co-founder and former CEO of IPSY, the beauty subscription that grew to over 3M subscribers and $200M ARR, creating a $1B digital beauty powerhouse.Born in Buenos Aires and raised in the US, Marcelo’s career took him from finance at J.P. Morgan (where he invested in Mercado Libre) to Funny or Die, a comedy startup backed by Will Ferrell. Later, he joined Real Influence, a platform that connected brands with YouTubers long before influencer marketing was mainstream.Today, he’s building Evalion, a testing and monitoring platform for voice AI agents, based on the belief that in the near future millions of companies will build their own agents, as voice becomes the primary interface for how we interact with technology.[10:30] – The moment Marcelo realized you can’t outcompete Google. [11:48] – How Ipsy started: turning creators’ attention into a business model[23:00] – Founder–market fit vs. curiosity-driven founders[26:10] – Why passion for the process matters more than passion for the industry[32:40] – Voice as the next interface: from websites → apps → agents[48:40] – Building Evalion: why trust and reliability will be the next real moat in AI.GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrssMarcelo's LinkedIn: https://www.linkedin.com/in/marcelocamberos/Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/Do you want AI powered productivity?Get 3 Months Free of Notion: Business Plan + Unlimited AI 👉 http://rebrand.ly/NTN8YTR3

    57 min

About

The outsider’s guide to Silicon Valley. I came here as a foreigner to learn what truly sets the best apart: the decisions, strategies, and mindsets that outsiders often see more clearly than insiders. Each week, I go deep with founders, investors, and operators to uncover the real reasons behind their success. Past guests include the founders of Vercel, Auth0, Nubank, Mercado Libre and Kavak.

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