Startupable
Enzo Cavalie
0
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.
Jaksot
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Resend CEO: Why Great Startups Enter Bad Markets | Zeno Rocha 16.09.2026 59minresented by Ashurst Perkins Coie. Paul Navarro works with some of the best founders in Latin America, many of them guests on the podcast. I always ask my guests who I should interview next, and the only time anyone recommended a lawyer, it was Paul. Glad to have them as a founding sponsor.👉 ashurstperkinscoie.com/professionals/paul-l-navarro-------------------------Every founder is taught to avoid crowded markets.Zeno Rocha bet his company on one of the most crowded markets in tech: email. He started Resend in 2023, and they're now at 4M users and 100k paying customers.Every other developer category had been rebuilt. Auth0 led auth until WorkOS and Clerk showed up. Heroku led hosting until Vercel. But in email, SendGrid was bought by Twilio for $2B and the product decayed. The rest got acquired too, and stopped improving.His bet was care: dark mode, animated icons, details nobody in the category had bothered with. Then AI turned email into a hot market again, and what he had to care about changed.Also in this episode:* Why the giants in your category are more vulnerable than they look* The advantage of knowing nothing about the market you enter* What changes when your fastest-growing customer is an agentGET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrssZeno Rocha's Linkedin: https://www.linkedin.com/in/zenorochaEnzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/-------------------------Jumpstart is the immigration service I wish I'd had when I moved to the US. Bianca and Fabiano have helped 1,250+ founders get O-1, L-1 and EB visas with a 98% approval rate, and if it doesn't come through, they DON'T charge you. 👉 https://www.gojumpstart.com/ -
Manifest: The $100B Bet on AI-Native Law Firms 09.09.2026 53minThis episode is presented by Ashurst Perkins Coie, the law firm guiding emerging companies from incorporation to exit. → ashurstperkinscoie.com/professionals/paul-l-navarro-----------------------------When Dan Mishin set out to build legal services powered by AI, every investor gave him the same feedback: why not just sell software?He refused. Selling software to law firms didn’t fix the system and incentives behind expensive legal services.The bet underneath it: AI is the leverage that finally makes a services business as good as SaaS.When each lawyer is 10x more productive, the company stops scaling with headcount. Dan’s benchmark: the largest law firm in the world does $7B in revenue with 1,200 attorneys.-----------------------------Also in this episode:The case for and against the hype of AINSThe ownership innovation that made Manifest venture-backableWhether AI services can hold quality and margins as they scaleGET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrssDan Mishin's LinkedIn: https://www.linkedin.com/in/danielmishin/Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/ -
🎧 The 25 yo Brazilian vs Scale, Mercor & Surge | José Nunes, Vetto AI 02.09.2026 1t 2minThis episode is presented by Ashurst Perkins Coie, the law firm guiding emerging companies from incorporation to exit. → ashurstperkinscoie.com/professionals/paul-l-navarro-----------------------------Frontier AI labs have no shortage of companies willing to collect data for them.Their harder problem is determining which data will actually make their models better.José Nunes built Vetto to solve that problem. Instead of waiting for a lab to specify the data it needs, Vetto studies where a model is underperforming and designs the work required to improve it.Also in this episode:His journey from a small town in Brazil to Silicon ValleyWhy the most valuable part of AI data happens before collectionHow Vetto competes with the labs in researchHow it recruits researchers it cannot outbid the frontier labsWhy researchers hired in Brazil can perform alongside people from DeepMindGET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrssJosé Nunes´s LinkedIn: https://www.linkedin.com/in/jose-andrenunes/Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/ -
The CTO Who Turned Down Pro Soccer to Build Firecrawl | Nicolas Silberstein, Firecrawl 26.08.2026 55minAt 12, one of Brazil's biggest soccer clubs offered Nicolas a spot on its pro track. Saying yes meant dropping out of school. He said no.Today he's playing the "main league" of Silicon Valley: building an AI company in SF, against the smartest, best-funded people in the world. In his words, "you're playing against the Pelés and Kakás."That company became Firecrawl, the biggest web-scraping repo on GitHub. 170k stars from a team of 20.Firecrawl does one unglamorous job: it reads webpages for AI. It takes a page full of code and turns it into clean text a model can use. Almost every AI agent needs that and agents now browse the web more than people do. (according to Cloudflare).Also in this episode:His path from Brazilian soccer to Silicon ValleyThe "indie hacker test" for defensibilityWhat he means by building the eyes for AGIWhy the best product is the one your users never seeWhy, if you're not building for agents, you may not be here in 5 yearsGET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrssNicolas's Linkedin: https://www.linkedin.com/in/nicolas-silberstein-camara/Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/This episode is presented by Ashurst Perkins Coie, the law firm guiding emerging companies from incorporation to exit. → ashurstperkinscoie.com/professionals/paul-l-navarro -
From no English at 18 to founding Reach Capital ($1B fund) - Esteban Sosnik 19.08.2026 59minFive 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 LibreWhy Reach invested in Replit at pre-seed in 2016Why AI is raising the bar for technical cofoundersThe “bloodbath” Esteban expects as companies cut ten AI tools down to one or twoWho should move to Silicon Valley and how everyone else should spend time hereGET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrssEsteban's Linkedin: https://www.linkedin.com/in/esteban-sosnik-779159/Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/ -
0 to $1.2B: HappyRobot’s anti-Silicon Valley playbook 04.08.2026 54minHappyRobot 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 waitingGET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrssPablo's Linkedin: https://www.linkedin.com/in/pablorpalafox/Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/ -
BoldVoice: How 7 People Built a $10M AI Company 25.07.2026 42minBoldVoice 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 speakersWhy BoldVoice built its audio AI technology in-houseHow a seven-person team surpassed $10M in revenueHow BoldVoice turns AI research into a better coaching productGET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrssAnada's Linkedin: https://www.linkedin.com/in/anadalakra/Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/ -
GitHub's Plan for the Agents War Isn't an Agent 11.07.2026 1t 21minGitHub 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 yearsWhy coding agents are just the beginning: code review, SRE, debuggingWhat Rappi and Loft, two messy physical-world businesses, taught him about humans in the loopGET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrssLuis LinkedIn: https://www.linkedin.com/in/artificial-intelligence/Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/ -
5 Ways LatAm Founders Break Into Silicon Valley 17.06.2026 59minSantiago 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 SFAlso in this episode:Why San Francisco Runs on Abundance, Not ScarcitySilicon Valley’s Real Advantage Is the Circle of TrustWhy VC Conviction Is Becoming More Psychological Than RationalWhy AI Makes “Informative” Content a Losing GameWhy San Francisco Happens IndoorsGET 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 -
How I Sold 8 US B2B Clients in 3 Weeks as a Foreigner | Carlos Chavez, Braven 10.06.2026 44minCarlos 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 InSelling AI Into a Traditional IndustryRaising From US VCs as an OutsiderWhy San Francisco’s “Boring” Culture Can Be a SuperpowerGET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrssCarlo's LinkedIn: https://www.linkedin.com/in/carlosachavezr/Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/ -
How Act One VC Became One of LA’s Top Seed Funds 31.05.2026 1t 15minAct 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/tssnwsrssAlejandro's LinkedIn: https://www.linkedin.com/in/alguerrero/Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie -
The 25-year-old Venezuelan coming for US banks with AI | Victor Cardenas, Slash 19.04.2026 39minHis 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 softwareHow they’re using internal agents to multiply team productivityWhat to do when your startup loses 60% of its revenue overnightWhy building for one person is better than building for a marketGET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrssVictor's LinkedIn: https://www.linkedin.com/in/victor-d-cardenas/Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/ -
Techstars’ CEO: The Venn Diagram Of Billion Dollar Ideas (How To Create Unicorns) 21.01.2026 47minDavid 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 stuckTechstars’ internal meme: “Replace ‘AI’ with ‘software’”Why AI agents will do venture capital — and probably better than humansJack 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/tssnwsrssDavid's LinkedIn: https://www.linkedin.com/in/davidgcohen/Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/ -
Freepik CEO: "The Day I Realized AI Would Destroy Us" — A Company That Refused To Die 21.12.2025 1t 12minJoaquín 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 edgeGET 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/ -
I Built a $4.4B SaaS and AI Agents Destroyed It: The End "Per Seat" Pricing 10.12.2025 47minMy 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 coveredWhy the Agent Economy is impossible without a new metering layerWhy seat-based pricing is dead and what replaces itWhy generalist agents lose to specific domain expertsHow the tech recession forced Outreach to reinvent itselfGET 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 👉 https://rebrand.ly/NTNENGYTR3 -
#1 Forbes Angel Investor: "Stay Home!" The AI Playbook for Non-US Founders 26.11.2025 53minMy 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/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 👉 https://rebrand.ly/NTNENGYTR3 -
$1B Founder: "AI Voice Infrastructure Doesn't Exist Yet" Here is Why That's $10B Opportunity 13.11.2025 56minMy 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 -
Investor in Uber, Roku & Siri: What He Looks for in Iconic Consumer Products 29.10.2025 1t 13minMy 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 lifeShawn’s key lessons from 20+ years of consumer investing.GET THE BEST OF THE INTERVIEWS IN OUR NEWSLETTER🗞️Read it: https://rebrand.ly/tssnwsrss -
The Forward Deployed Engineering Playbook | Pablo Palafox, Happy Robot 13.10.2025 1t 16minI 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 -
From Immigrant to a $3B Exit: The Story of Sendgrid | Issac Saldana, Sendgrid, Memo 03.06.2024 1t 5minMy 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/
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