Frank Slootman, Chairman of the Board at Snowflake, shares his groundbreaking perspective on leadership by blending passion with managerial skill. He challenges the traditional 'founder vs. manager' mindset, emphasizing the importance of intellectual honesty and the need for adaptable leadership. Frank also discusses the critical balance between empowerment and hands-on involvement, drawing insights from his experiences at Snowflake and ServiceNow. Lastly, he touches on the transformative impact of AI and the future of app ecosystems in business.

Aaron Levie, co-founder and CEO of Box, has guided the cloud content management platform from a dorm room project into a publicly traded company with over $1B in annual revenue. In his second appearance on B2BaCEO, Aaron reflects on his founder journey, sharing how Box capitalized on cloud computing and their recent push to integrate generative AI.But our conversation goes far beyond Box. Aaron’s role has given him a unique vantage point on what the latest advances in AI mean for founders. We explore the AI applications that excite him most, where he sees opportunities for startups over incumbents, and the potential areas in AI that founders might be overlooking.(0:00) Intro(2:26) The Box journey(4:23) Transitioning to enterprise(8:26) Building a GTM flywheel(11:45) Lessons from the enterprise journey(15:16) Where AI is heading(18:14) Facing the innovator's dilemma(20:54) AI agents(26:15) Why AI is positive sum for the economy(30:24) The AI doomer debate(34:22) The evolving model ecosystem(40:30) Parting advice for founders

In this episode, I talk with Srinath Sridhar, CEO & Cofounder of Regie.ai, who has always been ahead of the AI curve. Sri and his co-founder Matt Millen started Regie.ai in 2019 with the idea that GPT-3 would transform how all of us write emails. Today, Regie uses AI to automate sales prospecting for the enterprise. The company's Auto-Pilot automates most of the repetitive tasks involved in demand generation, including writing sequences, scheduling calls and responding to emails. Sri knew in early 2019 that LLMs would be a game-changer. What he didn’t know was exactly what product to build. In this episode, we’ll dig into the details of how he did it.

Mohit Aron, founder of Cohesity and Nutanix, shares startup validation frameworks, product-market fit insights, and team building lessons. He emphasizes founder honesty, market evaluation, and scaling challenges. The discussion also covers generative AI's potential impact on enterprise technology and recommendations for new CEOs.

In this conversation, Sanjit Biswas, co-founder and CEO of Samsara and former Meraki co-founder, shares his remarkable journey from leaving a Ph.D. program at MIT to building two successful startups. He discusses Meraki's pivot to enterprise sales and its acquisition by Cisco for $1.2 billion. Sanjit reveals how Samsara achieved $1 billion in ARR through customer feedback and strategic capital allocation. He also shares insights on generative AI's potential and the vital role of company culture in scaling businesses. Engaging and inspiring!

My guest today is Doug Winter, the founder and CEO of Seismic, a leading enterprise sales enablement platform. Today, Seismic has a team of 1,500 people and nearly $400 million in recurring revenue. We start the conversation with Doug explaining what sales enablement actually means. From there, we turn to the early days of Seismic and unpack Doug’s approach to finding product-market fit, positioning, and targeting enterprise customers from day one. He speaks candidly about the challenges of scaling and closes with actionable advice for founders in 2024. Fewer than 1% of B2B software companies reach Seismic’s scale. Doug’s story offers a valuable blueprint for founders with similarly audacious ambitions. I hope you find this conversation as inspiring as I did. Let’s dive in! (00:00) Cold open (2:21) Doug explains what sales enablement is (3:39) Genesis of the idea for Seismic (7:08) Seismic's scrappy early days (13:10) Lessons from fundraising (18:23) Targeting large enterprises from day one (22:32) Scaling a GTM engine (28:23) Making proactive leadership changes (37:12) Running great board meetings (40:59) Impact of AI on Seismic's business (44:42) Advice for founders starting in 2024

Naveen Rao, Co-founder of MosaicML and head of Generative AI at Databricks, shares insights on AI landscape, MosaicML acquisition, urgent AI questions, and future of generative AI. He reflects on past successes, challenges, and offers valuable lessons for founders navigating the AI moment.

Robert Nishihara, Co-Founder & CEO of Anyscale, discusses building a distributed computing system for AI, the challenges of managing deployment models, hiring and building a team, importance of repetition and learning from founding stories, and optimism for the future of technology.

My guest this month is Tracy Young, the co-founder and former CEO of PlanGrid, a productivity tool for construction companies. From going through YC and losing a co-founder to cancer, to being acquired by Autodesk for $875 million, Tracy has picked up many valuable lessons that other founders and CEOs can learn from. Our conversation unpacks these lessons, including finding (and keeping!) product-market fit, navigating startup growing pains, showing up effectively to board meetings, and managing the emotional toll of fundraising. We also speak about Tracy’s new venture, TigerEye, and what she’s doing differently the second time around. After having countless conversations with founders over the years, I thought I’d heard it all. Tracy proved me wrong. Her story serves as an inspiration for aspiring entrepreneurs in any industry.

If you’re not hardcore about AI, then stop the podcast now — because this episode for real technology nerds. Ashu’s guest is Matei Zaharia, CTO and cofounder of Databricks, and a professor of computer science at Stanford University. Ashu and Matei cover a lot of ground — most of it technical, all of it very relevant for anyone who’s serious about building with artificial intelligence. They start with a discussion of Databricks’ early days: how the startup established a foothold in a market dominated by entrenched incumbents and some of the challenges Matei and his cofounders faced. The rest of the conversation is all about AI. Matei breaks down the most common challenges that enterprises run into when attempting to adopt AI. He shares tips for how startups can best deploy foundation models. And he speculates on what the game-changing new use cases for AI will be over the next two years. Matei also pulls back the kimono on some of the cutting-edge machine-learning research he and his team at Stanford are working on. Finally, listen to the end for a fascinating exchange about artificial intelligence beyond large language models.