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

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Carlo's LinkedIn: https://www.linkedin.com/in/carlosachavezr/

Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/

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"

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Alejandro's LinkedIn: https://www.linkedin.com/in/alguerrero/

Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie

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

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Victor's LinkedIn: https://www.linkedin.com/in/victor-d-cardenas/

Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/

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”

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David's LinkedIn: https://www.linkedin.com/in/davidgcohen/

Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/

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/

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

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 interesting
• Will AI kill marketplaces? The real impact on e-commerce
• The next big play: buying offline businesses and 10x’ing them with AI
• The trillion-dollar opportunity in B2B digitizationDo AI startups really need less capital?

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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

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

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.

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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.

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