Startupable

Hosted by Enzo Cavalie

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Aug 2026

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About the show

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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25 recent

August 19, 202659 min

From no English at 18 to founding Reach Capital ($1B fund) - Esteban Sosnik

Five years ago Esteban Sosnik brought me to the US, helped me get my visa, and gave me a seat at Reach Capital. Those have been the best and highest-growth years of my life. Today his episode goes live, and I finally get to tell his story, because most people don't know the arc. The wildest part? He's too humble to tell you any of this himself. So I got it out of him on today's episode. This was a special one for me. Hope you enjoy it! Also in this episode: How Argentina’s first VC circle found and backed Mercado Libre Why Reach invested in Replit at pre-seed in 2016 Why AI is raising the bar for technical cofounders The “bloodbath” Esteban expects as companies cut ten AI tools down to one or two Who should move to Silicon Valley and how everyone else should spend time here GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️ Read it: https://rebrand.ly/tssnwsrss Esteban's Linkedin: https://www.linkedin.com/in/esteban-sosnik-779159/ Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/

August 4, 202654 min

0 to $1.2B: HappyRobot’s anti-Silicon Valley playbook

HappyRobot went from zero to a $1.2B valuation in three years. DHL, Repsol and Koch Industries on the customer list. Four industries, three continents. The company just raised a $150M Series C led by Prism Capital and Eurazeo. A little over a year ago, Pablo Palafox came on the show as a YC founder building AI voice agents for freight brokers. He just came back a unicorn. They got there by doing what the Silicon Valley playbook says not to. Also in this episode: * Why he almost quit his own company to work as a freight broker * Why DHL has more in common with a telco than with a regional logistics shop * How forward-deployed engineers became their biggest go-to-market lever * Why they went global at Series B instead of waiting GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️ Read it: https://rebrand.ly/tssnwsrss Pablo's Linkedin: https://www.linkedin.com/in/pablorpalafox/ Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/

July 25, 202642 min

BoldVoice: How 7 People Built a $10M AI Company

BoldVoice reached $10M+ in ARR with a team of seven. Five million users across 150 countries. In January, the company raised a $21M Series A led by Matrix. What looks like a simple coaching app is powered by proprietary AI models trained to hear how people actually speak English. That technical foundation became the moat behind BoldVoice. Also in this episode: What conventional speech recognition misses about non-native speakers Why BoldVoice built its audio AI technology in-house How a seven-person team surpassed $10M in revenue How BoldVoice turns AI research into a better coaching product GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️ Read it: https://rebrand.ly/tssnwsrss Anada's Linkedin: https://www.linkedin.com/in/anadalakra/ Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/

July 11, 20261 hr 21 min

GitHub's Plan for the Agents War Isn't an Agent

GitHub Copilot started the AI coding market. Today, barely a serious developer touches it. Not even a vibe coder like me: we mostly live in Claude Code, Cursor, and Codex. These players are at war to own the coding agent, maybe the biggest AI market there is. Luis Bitencourt runs GitHub Copilot. So I asked him straight up: is Copilot losing the race? His answer: Everyone's fighting on two layers: the harness and the model. Luis thinks neither is winnable. Also in this episode: Why Microsoft's distribution buys a head start of months now, not years Why coding agents are just the beginning: code review, SRE, debugging What Rappi and Loft, two messy physical-world businesses, taught him about humans in the loop GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️ Read it: https://rebrand.ly/tssnwsrss Luis LinkedIn: https://www.linkedin.com/in/artificial-intelligence/ Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/

June 17, 202659 min

5 Ways LatAm Founders Break Into Silicon Valley

Santiago Zavala sat me down in front of the 500 Global community in San Francisco.The room was full of founders spending a few weeks in the Bay trying to crack the city.So Santiago pushed me on the one thing I get asked most: how do you actually break into Silicon Valley?Here’s what I think now after 5 years in SF Also in this episode: Why San Francisco Runs on Abundance, Not Scarcity Silicon Valley’s Real Advantage Is the Circle of Trust Why VC Conviction Is Becoming More Psychological Than Rational Why AI Makes “Informative” Content a Losing Game Why San Francisco Happens Indoors GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER 🗞️Read it: https://rebrand.ly/tssnwsrssSantiago's LinkedIn: https://www.linkedin.com/in/santiago-zavala-47a68b7/Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie

June 10, 202644 min

How I Sold 8 US B2B Clients in 3 Weeks as a Foreigner | Carlos Chavez, Braven

Carlos Chávez grew up watching his father work in insurance. Today he’s building Braven, AI agents that take over what underwriters still do by hand: processing submissions, quoting policies, binding coverage. One underwriter on Braven handles 30x the volume they did before.But the story isn’t the product. Carlos arrived from Colombia with no network in the US insurance industry. Latin American VCs told him directly that a Latin team couldn’t run commercial processes in the US.Braven raised $6M from Collide Capital, Fiat Ventures, Broom Ventures, Aito Capital, and a16z scout. Also in this episode: Moving to the US Gradually vs. Going All In Selling AI Into a Traditional Industry Raising From US VCs as an Outsider Why San Francisco’s “Boring” Culture Can Be a Superpower GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrss Carlo's LinkedIn: https://www.linkedin.com/in/carlosachavezr/ Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/

May 31, 20261 hr 15 min

How Act One VC Became One of LA’s Top Seed Funds

Act One Ventures’ Fund 1 was $4M. Their second investment was AuditBoard. Every other investor passed. “The market is too small”, they said. In 2024 it sold for $3.1 billion, one of the biggest software exits of the year, on just $43.5M ever raised. Alejandro didn't learn to spot that in venture. He learned it in music. His early career was A&R, the people who find talent before anyone signs it. He came up under the man who discovered Linkin Park, a band every label had passed on. He reads founders the way a scout reads a raw artist. Not by the resume. By whether they've lived the thing they're building. That instinct isn't an accident. Alejandro grew up fifteen minutes from the Tijuana border. Son of a mechanic, first in his family, no network. Also in this episode: - The Linkin Park analogy for how real pattern matching works - How a $73M fund accidentally became a native AI fund - The hard conversations, in person not over Zoom, with founders whose model no longer works’ - The investing principle from the border: "I try to keep it real" GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️ Read it: https://rebrand.ly/tssnwsrss Alejandro's LinkedIn: https://www.linkedin.com/in/alguerrero/ Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie

April 19, 202639 min

The 25-year-old Venezuelan coming for US banks with AI | Victor Cardenas, Slash

His name is Victor Cardenas, founder of Slash.$250M in revenue. 65 people. Profitable.2% of all Facebook ad spend runs through Slash. More than 5,000 businesses spend almost $10B a year on its corporate cards.A year ago, Mickey Malka of Ribbit Capital, the world’s #1 fintech investor (Robinhood, Nubank, Coinbase), said, “fintech is dead.”Today, Ribbit is leading Slash’s $100M round at a $1.4B valuation.Also in this episode: How Slash found a new opportunity when “fintech was dead” Why the real advantage in the AI era isn’t in software How they’re using internal agents to multiply team productivity What to do when your startup loses 60% of its revenue overnight Why building for one person is better than building for a market GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrss Victor's LinkedIn: https://www.linkedin.com/in/victor-d-cardenas/ Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/

January 21, 202647 min

Techstars’ CEO: The Venn Diagram Of Billion Dollar Ideas (How To Create Unicorns)

David Cohen (founder of Techstars) was an angel investor in Uber. He also had the opportunity to invest in Lyft — and passed. Same market. Same timing. Two completely different outcomes in his portfolio. The difference? At Uber, he met Ryan Graves (the first employee) through Techstars. “I clicked with him.” He invested without ever meeting Uber’s founders. At Lyft, Matt Van Horn was a mentor at Techstars. They were friends. But the idea seemed stupid to him: “Intercity transportation for college students? I didn’t get it.” That same team pivoted, followed Uber, and built a multi-billion-dollar company. After 20 years evaluating startups, the pattern behind his misses is always the same. Also in this episode: Why AI creates a "barbell effect" for startups — the middle gets stuck Techstars’ internal meme: “Replace ‘AI’ with ‘software’” Why AI agents will do venture capital — and probably better than humans Jack Bogle’s philosophy applied to VC: “The financial industry only subtracts value” GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrss David's LinkedIn: https://www.linkedin.com/in/davidgcohen/ Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/

December 21, 20251 hr 12 min

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 frozen The “Humans vs AI” framework and what machines will never replicate The hardest conversations with artists who thought their careers were over The strategic mistake that made Adobe, Getty, and Shutterstock fall behind on AI Why distribution is a temporary advantage, not a real moat How 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/