Aaron Levie, the CEO of Box, reflects on the cloud storage company’s entry into the enterprise market. He was skeptical about pivoting away from consumers, and it was challenging. But by staying disciplined with the product and deeply understanding market trends, they've made the strategic shift from B2C to B2B work.
Sep 2025
Aaron Levie: Why Startups Win In The AI Era
For nearly two decades, Box co-founder and CEO Aaron Levie has been at the frontlines of how technology reshapes work—guiding the company through the rise of mobile, the cloud, and now the age of AI.In his fireside with YC General Partner David Lieb at AI Startup School, Aaron re ... Show More
40m 27s
May 2025
Undoing a $5 Billion Acquisition and Building a Durable Standalone Plaid (with Plaid CEO Zach Perret)
We sit down with Zach Perret, CEO of Plaid, to discuss the remarkable journey of Plaid and the broader fintech landscape over the past several years. Zach takes us blow-by-blow through journey of almost getting acquired by Visa, the challenges faced during the COVID-19 pandemic… ... Show More
59m 7s
Aug 2025
Controllers Classified: Weathering tariff risks
Host Erik Zhou, CAO at Brex, sits down with Richie Mashiko, Fractional CFO, to unpack the financial complexities of running high-growth e-commerce and CPG brands. From measuring the right things to navigating ad spend, pricing strategies, and fragile supply chains amidst tariffs, ... Show More
39m 49s
Mar 2025
How to Lead a Successful Turnaround
When a company, division, or product line has been struggling for some time, it can feel nearly impossible to get things back on track. But big turnarounds are possible, provided you have a team willing to work hard, be creative, and embrace change. When he was president and CEO ... Show More
28m 33s