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.
Episodes
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. T
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
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 misse
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:
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 SFAlso in this episode:Why San Francisco Runs on Abundance, Not ScarcitySilicon Valley’
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 VC
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.
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 valu
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 Tec
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
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:
#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
$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 In
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 breakthrou
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.Rec
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 transi
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
The AI Investing Strategy of Uber’s 1st Head of Data Science | Kevin Novak, Rackhouse Ventures
My guest is Kevin Novak, the founder and Managing Partner of Rackhouse Ventures, an early-stage venture firm focused on the intersection between AI and the real world. Kevin has had a long and respected career in Data Science and AI, serving as Uber’s first head of data science and inventing Uber's dynamic pricing feature. Before Rackhouse, he was the Chief Data Officer of Tala Financial, advised
The Past, Present and Future of Brazil’s Venture Ecosystem | Rodrigo Baer, Upload Ventures
My guest today is Rodrigo Baer, co-founder and General Partner at Upload Ventures. I met Rodrigo a year ago during a trip to Brazil and was impressed by his knowledge of the history of the Brazilian market and the trends of where it is going.Rodrigo investing in Brazilian startups in 2010, then went on to become a Managing Director for Redpoint eventures and a Partner at SoftBank's Early Stage fu
How to Raise from Emerging LPs: A Guide for GPs | David Zhou, Alchemist
This week I talked to David Zhou, Head of Investor Relations at Alchemist Accelerator, to understand who emerging Limited Partners (LPs) are and what motivates them, and how General Partners (GPs) can raise capital from them.Over a year ago, David wrote “The Non-Obvious Emerging LP Playbook”, which has become one of the best blog posts on the somewhat obscure world of Limited Partners, the money b
Why Every US Company Needs a Latino Strategy | Sean Salas, Camino Financial | S1:EP5
There are nearly 5 million Latino-owned businesses in the US and nearly 1 in 4 new businesses are started by Latinos. And yet, access to banks and financial products is not as easily available for these entrepreneurs. Sean Salas decided to change that by co-founding Camino Financial. Through technology and AI, they offer affordable loans to satisfy the demand for credit that rises to 20 billion d
The Edtech that Acquired a University: Alura, One of Brazil’s Largest Online Education Platforms | Paulo Silveira, Alura | S1:EP4
Numerous startups like online bootcamps and MOOCs have tried to disrupt and reimagine the higher education system. However, the idea of merging these modern educational models with traditional universities seemed far-fetched until recently.With over 120k paid subscribers and 1M users, Alura made headlines by acquiring FIAP, a well-known private technology university in Brazil. This move was a str
Building the AWS of Fintech and How Payments Will Shape the Future of Software | Richie Serna, Finix | S1:EP3
Today’s guest has a habit of explaining how the payment ecosystem works on any opportunity he gets. Leveraging this expertise, Richie Serna founded Finix, a fintech that started as a payment infrastructure startup and gradually expanded into facilitating and processing payments.To date, Finix has raised more than 130 million dollars and processes tens of billions of dollars in payments.Riche and I
Elias Torres, Drift & Novy | Embracing Conflicting Advice, Why Product Defensiblity is Dying & The Future of SaaS | S1:EP2
Elias is the co-founder of Drift, a software platform that’s reimagining the B2B buying experience by helping businesses deliver personalized conversations with their customers. Drift serves over 50,000 customers including companies like ServiceNow, Okta, Mindbody, Adobe and Snowflake; and reached unicorn status in 2021 when private equity firm Vista Equity Partners acquired a majority stake. Prio
Kevin Efrusy, Accel | From Investing in Facebook to Investing in LatAm’s Startups and Youth | S1:EP1
This is my first episode, and I couldn't be more grateful to start with such an incredible guest. Today, I had Kevin Efrusy on the show. Kevin joined Accel Partners in 2003 and was the lead investor in companies like Groupon, Couchbase, and Facebook, which is likely one of the best venture investments of all time. The story of how he leveraged a “prepared mind” to source Facebook and convince Mark
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