Emery Wells, co-founder and CEO of Frame.io, details his incredible journey from NYC bartender to startup founder, culminating in a $1.3 billion sale to Adobe. He shares insights from his work with SNL that ignited his entrepreneurial spirit. Discussing the importance of design and a unique company culture, he rejects the lean startup model and emphasizes maintaining high standards. Emery also navigates the intense processes of fundraising and acquisitions, along with the impact of AI on creativity—highlighting lessons learned along the way.

Dara Khosrowshahi, the CEO of Uber and a leader in transforming the company to profitability since 2017, shares insights into autonomous vehicles and consumer behavior shifts. He discusses overcoming challenges in AV strategy, emphasizing the societal importance of safety and user preferences. Dara also reflects on Uber's cultural reset, evolving company values, and the significance of operational efficiency. He highlights innovative adaptations in global markets and the vital role of transparent leadership in fostering trust and driving performance.

Mike Maples, an 8x Midas List investor and founding partner at Floodgate Fund, shares his insights on startup success and the future of venture capital. He explores how top startups redefine categories and discusses the significance of 'pattern-breaking' ideas. The conversation dives into pivotal moments in startup history, including the rise of Twitch and Tesla. Maples also highlights the traits of successful founders, emphasizing storytelling and community movements as key elements in creating impactful products.

Josh Reeves, Founder and CEO of Gusto, discusses the early days and strategic growth of Gusto, highlighting the importance of proving product viability before scaling. He emphasizes building a culture aligned with company values, work-life balance, long-term success, and empowering teams for efficient product development. Reeves also shares insights on hiring executives, company growth, and Gusto's vision to become an entrepreneurship platform.

Eric Glyman, CEO of Ramp, shares insights on leveraging AI internally, building moats in AI for startups, and the concept of self-driving money. The discussion also covers hiring strategies, motivations, and success factors in leading a fast-growing startup.

Klarna CEO Sebastian Siemiatkowski discusses turning the company profitable, boardroom drama with Sequoia, and building a digital financial assistant. Topics include leadership, company culture, handling valuation resets, regulatory challenges, AI integration, and lessons in venture capital.

CEO of Datadog, Olivier Pomel, shares insights on fundraising, building the right product, open beta transition, platform vision, customer-centric approach, bottom-up sales strategy, collaborative management, staying close to customers, pricing strategy, fostering culture of discipline, AI impact, choosing NYC over Silicon Valley.

Steve Kaufer, Co-Founder of Tripadvisor, shares insights on handling negative reviews, the psychology of user behavior, and the impact of AI on review platforms. He also discusses the importance of agility in business, setting company culture, and hiring the right people. Additionally, Steve reflects on his entrepreneurial journey, managing through crises like 9/11 and COVID-19, and his new venture Give Freely.

Bill Shufelt, CEO of Athletic Brewing, shares the journey from hedge fund trader to leading non-alcoholic craft beer producer. Topics include unscalable brand strategies, celebrity partnerships, market challenges, personal sacrifices, innovative brewing processes, and cultural differences in the non-alcoholic beer industry.

Robinhood CEO Vlad Tenev discusses meme stock crisis, crypto views, AI in finance, brand strategy, Gold Card launch, X1 acquisition, remote work challenges, and hiring talent in an engaging podcast conversation.