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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. 12/21/2025

    Freepik CEO: "The Day I Realized AI Would Destroy Us" — A Company That Refused To Die

    Joaquín Cuenca, CEO and founder of Freepik, had built a $70M revenue company with a team of 500 people. For over a decade, Freepik focused on building the largest image library on the internet. Then DALL·E 2 arrived and overnight, everything they had built suddenly felt at risk.Instead of freezing, Freepik became one of the first major image platforms to integrate generative AI. Today, Freepik is one of the most widely used AI creative apps, according to a16z. This is exactly how they did it. Why launching AI without a clear strategy beat staying frozenThe “Humans vs AI” framework and what machines will never replicateThe hardest conversations with artists who thought their careers were overThe strategic mistake that made Adobe, Getty, and Shutterstock fall behind on AIWhy distribution is a temporary advantage, not a real moatHow building Freepik from Málaga—not Silicon Valley—became a competitive edge GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrssJoaquin's LinkedIn: https://www.linkedin.com/in/joaquin-cuenca-abela-905717a/Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/

    1h 12m
  2. 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
  3. #1 Forbes Angel Investor: "Stay Home!" The AI Playbook for Non-US Founders

    11/26/2025

    #1 Forbes Angel Investor: "Stay Home!" The AI Playbook for Non-US Founders

    My guest today is Fabrice Grinda, co-founder of FJ Labs and one of the most prolific angel investors, with +1,100 investments and key bets like Airbnb, Alibaba, and Flexport.Prior to FJ Labs, Fabrice built multiple companies including Zingy, which he scaled from near bankruptcy into a $200M exit, and OLX, which he grew to 300M users across +40 countries, before it was acquired by Naspers.Today he runs FJ Labs as an “angel investor at venture scale,” evaluating hundreds of deals a week and backing 150–200 startups a year with a fast, founder-friendly process. Why being a public company CEO stopped being interestingWill AI kill marketplaces? The real impact on e-commerceThe next big play: buying offline businesses and 10x’ing them with AIThe trillion-dollar opportunity in B2B digitizationDo AI startups really need less capital?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

    54 min

  4. 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
  5. Investor in Uber, Roku & Siri: What He Looks for in Iconic Consumer Products

    10/29/2025

    Investor in Uber, Roku & Siri: What He Looks for in Iconic Consumer Products

    My guest today is Shawn Carolan, Managing Partner at Menlo Ventures, one of Silicon Valley’s oldest venture firms with more than $5B under management. Shawn led early investments in Uber, Roku, Siri, and Chime, generating over $2B in returns for Menlo’s LPs. Behind those wins is a clear philosophy, what Shawn calls his Consumer Utilitarian Framework: a model for backing companies that use breakthrough technologies to meet timeless human needs in faster, cheaper, and better ways. Today we talked about: His Consumer Utilitarian Framework and Menlo Ventures’ 4 investing pillars. Core principles: timeless human needs × evolving technology. AI as the next “ingredient technology” unlocking new markets. How AI gives failed apps like MyFitnessPal a second life Shawn’s key lessons from 20+ years of consumer investing. GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER 🗞️Read it: https://rebrand.ly/tssnwsrss

    1h 14m
  6. The Forward Deployed Engineering Playbook | Pablo Palafox, Happy Robot

    10/13/2025

    The Forward Deployed Engineering Playbook | Pablo Palafox, Happy Robot

    I spoke with Pablo Palafox, CEO and co-founder of Happy Robot, the AI agents startup that's automating logistics and supply chain. Pablo studied industrial engineering and pursued a Ph.D. in computer vision in Munich. Alongside his brother Javier Palafox (COO) and Luis Paarup (CTO), they were part of Y Combinator's in 2023, where they pivoted from their initial idea to what Happy Robot is today. Recently, Happy Robot raised $44M in its Series B, led by funds like Base10 and a16z. Their "Forward Deployed Engineering" approach allowed them to grow their revenue 20x since their Series A. Today, they work with over 100 clients, including the largest freight brokerage firms in the U.S. Today, Pablo and I talked about: Why implementation is more important than technology.How to get your clients to see you as an "AI partner" instead of just a vendor.How the "Forward Deployed Engineering" model drove their 20x growth.How they went from being a "threat" to a "strength" for their clients.Why building a blame-free culture is essential when working with imperfect technology. YouTube  | Sitio Web

    1h 17m
  7. From Immigrant to a $3B Exit: The Story of Sendgrid | Issac Saldana, Sendgrid, Memo

    06/03/2024

    From Immigrant to a $3B Exit: The Story of Sendgrid | Issac Saldana, Sendgrid, Memo

    My guest is Isaac Saldana, co-founder and former CEO of Sendgrid, the API centric email platform which went public in 2017 and was acquired by Twilio for 3 billion in 2019. Before Sendgrid, Isaac started multiple startups that failed and faced a ton of challenges as a first time founder, with very little business background and a very shy personality. Today, we discussed Isaac’s challenges in transitioning from founder to CEO, his decision to bring in an external CEO to SendGrid, and the lessons he learned along the way. We also covered the company-building lessons he gained at SendGrid, including insights on product development, market timing, and team building. Finally, we talked about his latest venture, Memo, and how he aims to empower introverts to build their personal brands and social capital in a world dominated by social media. Isaac is a very successful yet low-profile and humble founder, so I’m sure many of you will empathize with his personal story. - GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️  Read it: https://rebrand.ly/tssnwsrss - Issac's LinkedIn: https://www.linkedin.com/in/isaacsaldana/  Issac's new company: https://memo.com/

    1h 6m
  8. A Bullish Take on LatAm’s Growth Equity & Lessons from Investing $8BN at Softbank| Paulo Passoni, Valor Capital Group

    05/21/2024

    A Bullish Take on LatAm’s Growth Equity & Lessons from Investing $8BN at Softbank| Paulo Passoni, Valor Capital Group

    Paulo Passoni is Managing Partner at Valor Capital Group, a venture capital and growth equity firm investing across Brazil, LatAm, and the US. Before Valor, Paulo played a protagonic role in developing LatAm’s growth equity ecosystem as a Managing Partner at SoftBank, managing their $8 billion LatAm Fund. Paulo invested and acted as a board member of several Brazilian unicorns including VTEX, Loggi and Creditas. He also invested over a decade in Latin America’s public and private equities at Third Point Management and Eton Park. In this episode, we talked about the non-obvious investing principles he’s learned over his career, why he’s bullish on LatAm’s venture and growth ecosystem, unlike other investors, and his reflections from his time at Softbank. We also d iscussed his frameworks for investing in growth-stage companies in Brazil and LatAm, including markets, regulatory tailwinds, business models, metrics, and teams; and how this has changed since 2020 and 2021. GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️  Read it: https://rebrand.ly/tssnwsrss

    1h 3m
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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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