Yesterday Podcast

Aaron Levie, co-founder and CEO of Box, shares his incredible journey of building a $5B cloud storage company from a dorm room. He reveals how he cold-emailed Mark Cuban for investment, leading to a pivotal freemium strategy. Levie discusses Box's shift from consumer to enterprise, leveraging the iPhone's launch to drive adoption. He also dives into the transformative impact of AI on business workflows, and offers advice for young founders about navigating innovation without existing templates.

Jonathan Neman, co-founder and CEO of Sweetgreen, shares his journey from a young entrepreneur to leading a multi-billion dollar salad chain. From his parents' immigrant story to the cultural inspiration behind Sweetgreen, he reveals how Australian cafes sparked the concept for healthy fast food. Neman discusses the challenges of scaling operations, the importance of technology in enhancing customer experience, and his commitment to scratch cooking. He reflects on the emotional significance of the company's IPO and the role of family in his entrepreneurial journey.

Zach Sims co-founded Codecademy with Ryan Bubinski after dropping out of Columbia. And over a decade later in 2021, they sold to Skillsoft for $525M.We discuss his family, scrappy upbringing that led to Columbia, and early life stories before Codecademy.We also discuss YC, growing to hundreds of thousands of users in a few days, the reason they exited, and much more.Zach’s on the precipice of a new chapter in his life & work, and it was a pleasure to profile his life up until now. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit yesterdayy.substack.com

Joe Lonsdale co-founded Palantir (now worth ~$400B) and went on to found venture firm 8VC, the University of Austin, OpenGov, Addepar, and several other companies. In this wide-ranging conversation, Lonsdale traces his life story from deep family roots and early childhood to the present day. He shares the formative experiences that shaped his thinking, his years at Stanford, and the lessons learned from macro investing with Peter Thiel, especially digging into U.S. and Japanese bond markets. We explore chess, philosophy, and warfare; the courage to invent and build talent clusters; the founding stories behind Palantir and Formation 8 (now 8VC); and the vision behind the University of Austin. A rare look at one of Silicon Valley’s most prolific founders & investors, and one of my favorite conversations we’ve recorded so far. Enjoy! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit yesterdayy.substack.com

Gordon Ritter, co-founder of Emergence Capital and an influential figure in venture capital, shares his fascinating life story. He opens up about his childhood, shaped by curiosity and resilience, and his transition from banking to founding pivotal tech companies. Ritter discusses the immense returns from his investments in cloud computing, highlighting a philosophy of tackling hard challenges. He also reflects on life lessons from extreme mountain climbing and the importance of diverse partnerships in innovation.

Akshay Kothari, co-founder of Notion, shares his inspiring journey from a childhood in India to his role in creating a $10 billion productivity tool. He reflects on the challenges of shifting dreams from cricket to engineering and how a transformative trip to the U.S. changed his life. Akshay's experiences founding Pulse, its acquisition by LinkedIn, and his eventual partnership in Notion reveal the unpredictable nature of entrepreneurship. He also emphasizes the importance of mentorship and supporting young innovators in tech.

Dwarkesh Patel, host of The Dwarkesh Podcast, shares his journey from India to the U.S., highlighting cultural challenges and the impact of family expectations on his career choices. He details how a pivotal cold email saved his podcast, connecting him with influential figures like Jeff Bezos. Patel discusses the evolution of his intellectual interests and the power of networking, along with humorous ice cream anecdotes. He also reflects on navigating podcast monetization and the importance of meaningful content over popularity.

This week, we cover the life story of Guillermo Rauch, the founder and CEO of Vercel. Rauch grew up in Lanús, a working-class neighborhood in Buenos Aires, Argentina. He taught himself to code and by 11, he was freelancing online for clients abroad. In his teens, he became well-known for creating several influential open-source projects, including Socket.IO and Mootools. Rauch then dropped out of high school to work in Switzerland, and after a stint there, he moved to San Francisco. Around 2015, he founded Vercel (originally called ZEIT) out of Dogpatch Labs with the vision of radically simplifying frontend deployment through tools like Next.js, which his team also maintains. Today, Vercel powers the websites of Netflix, MrBeast, Supreme, and many more… and valued multiple billions of dollars. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit yesterdayy.substack.com

This week, we cover the life story of John Andrew Entwistle. He was once a Formula race car driver, during which he broke his back multiple times, and he even threw a house party that shut down his entire town. Amidst similar teenage years, John Andrew was sued by Microsoft, where he subsequently cc’d his dad on the email — a famed lawyer who did the Bernie Madoff and FTX cases. Later on, John Andrew became a Thiel Fellow and then sold his first company — Coder.com. From there, he started Wander.com… a luxury home rental company that’s now worth hundreds of millions of dollars. John Andrew has some of the most unique life stories and is a sheer force to compete with. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit yesterdayy.substack.com

Jessica Mah is the founder of inDinero and Mahway, a venture studio backing companies in aerospace, legaltech, and biotech. We discussed growing up in Westchester to immigrant parents, teaching herself to code at 10, and burning out from her first startup by 14. At 15, she dropped out of high school, enrolled in college, and later founded inDinero through Y Combinator at just 19 — at the time, the youngest female founder accepted. We covered her early struggles with retention, laying off most of her team, and rebuilding inDinero from the ground up. In her early 20s, she was on the cover of Inc. magazine and deemed “female Mark Zuckerberg". Later, Jessica stepped down as CEO after realizing she was miserable despite the company’s success. That shift led her to start Mahway — her “dream job”. Today, she lives radically transparently, races cars, flies planes, and redefines what it means to play the long game. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit yesterdayy.substack.com