Very First Win

Tarek Alaruri is the founder of Stuut, an AI platform that helps businesses collect the money they're owed. Companies like Honeywell, PerkinElmer, and CharterUp use Stuut to automate accounts receivable end to end, collecting 40% more revenue in their first few months on the platform. But before Stuut, Tarek was a broke kid out of college who took a commission-only trucking job because a recru...

Chris Farmer got banned from casinos for counting cards. That same obsession with statistics and risk turned into SignalFire, the data-driven venture firm he founded in 2013. In this episode of Very First Win, Chris tells Robert Hilmer how a lucky blackjack run in college sent him down the rabbit hole of modeling the game with a UC Berkeley professor, playing semi pro for years, and learning when...

Chaz Englander has built and sold two companies before most people figure out what they want to do. First was Fat Llama, a peer-to-peer rental marketplace that got into YC and sold for $45M. Then a last mile grocery delivery business he started three months before COVID that sold to GoPuff. Now he's building Model ML, a workflow automation platform for finance that raised $100M in its first ye...

Andrew Parker is the founder and CEO of Papa, the companion care platform pairing older adults with vetted "pals" who help with rides, tech, paperwork, and the thing nobody puts on a care plan: loneliness. In this episode, Andrew tells Rob about the moment that changed everything. He almost deleted the YC interview email at 5am, fished it out of his trash, and walked into a room where he...

What happens when the internet's "Queen of Shitty Robots" decides she wants to build something that outlasts the joke? In this episode of Very First Win, Rob Hilmer sits down with inventor, YouTuber, and founder Simone Giertz. She built a following of nearly 3 million on YouTube, first as the self-proclaimed "Queen of Shitty Robots" with creations like an alarm clock that s...

Mitesh Agrawal, CEO of Positron, joins Robert Hilmer on Very First Win to talk about building AI silicon for frontier inference workloads, coexisting with Nvidia, and the two challenges that define the chip game: talent and supply chain. Then he gets into his very first win, the $100M+ deal that taught him how to sell into a multi-trillion dollar company as a startup worth a fraction of that. The...

Jason Fried, founder of 37signals (Basecamp, HEY), joins Robert Hilmer on Very First Win. Jason has built one of the most well-known bootstrapped software companies of the last 25+ years. 27 years of profitability, ~60 people, zero VC money on purpose. In this episode he shares three early moments that shaped how he thinks about building: the rejection that lit a fire under him, his first $20 ever...

In this episode of Very First Win, Robert Hilmer sits down with Samir Vasavada, founder of Vise AI and the youngest tech unicorn founder in history. Samir started Vise at 15 years old in Cleveland, Ohio, dropped out of high school, and moved to San Francisco with no money, eventually living in the Crypto Castle while bootstrapping the company. Vise is now an AI-powered investment platform that hel...

Jonathan Bush is the co-founder of Athena Health and the co-founder and CEO of Zus Health, a national common patient record and medical record API. He ran Athena for 21 years before the company was taken private, and he's now also running for governor of Maine. In this episode, Jonathan tells the story of how Athena Health almost didn't exist. The company started as a women's health ce...

ElevenLabs is now an $11B company. Three years ago, a16z's Bryan Kim flew from San Francisco to London on 90 minutes notice to win the Series A. He packed in a minute, got his assistant to book the flight, landed, met the founder for lunch, and signed the term sheet on a piece of paper. Four hours on the ground. Then he flew home. In this episode of Very First Win, BK walks host Robert Hilmer...

In 2017, Andrew Antos founded Klarity AI, an artificial intelligence company built years before ChatGPT, before the AI boom, and before most people believed AI could actually work in production. Then he waited. For 7 years, Andrew kept building while the rest of the world ignored AI. Customers were skeptical. The market didn't exist yet. Most founders in his position would have pivoted, quit,...

Most entrepreneurs’ first wins are overlooked - but for Delian Asparouhov, it was a life-changing internship at Square that set his entire trajectory. Imagine going from a rejection just minutes before — only to have your biggest break come through because a CTO saw something in you during a late-stage Zoom call. That moment at Square in 2012 sparked Delian’s journey from Silicon Valley intern to...

Most social media icons will fade out—and often fade fast. But what if your biggest asset isn’t your followers, but your ability to build a real business? Nuseir Yassin, founder of NAS Company and  NasDaily  , reveals how he went from making a thousand one-minute videos to a venture-backed powerhouse with 70 million followers and a mission to democratize entrepreneurship through AI.In this episode...

Most real estate stories end with a closing; ‪@RyanSerhant‬ 's Very First Win begins with a prank call, a last-minute Paris trip, and a deal that seemed impossible - yet changed his entire career. His willingness to follow up relentlessly transformed a random phone call into a $8.3 million sale, all while navigating international scams, con artists, and the chaos of NYC real estate. In this ep...

Join us as we dive into the pivotal first win of Gary Vaynerchuk's entrepreneurial journey. Discover how a simple baseball card trade at age 14 shaped his mindset towards unlimited potential and minimal downside. Learn about the importance of early wins and failures in building confidence, the role of passion over fame, and how maintaining perspective through triumphs and failures fuels growth...