B2BaCEO (with Ashu Garg)

Frank Slootman turns the 'founder mode vs. manager mode’ debate on its head. 

Frank’s track record in B2B land is iconic: He took Data Domain from pre-revenues to a $2.5B acquisition by EMC. He led the IPO at ServiceNow, and when he left the company, it was worth $34B. Frank then took Snowflake public, and the company was worth over $70B when he retired earlier this year. 

After three successful CEO stints, Frank isn’t buying Silicon Valley’s fairytales about founders. His leadership style combines a manager’s prowess with a founder’s passion. Frank epitomizes what some might call “owner mode!”

(00:07) Frank's thoughts on 'founder mode' vs. 'manager mode' 

(00:47) The role of non-founder managers and CEOs 

(09:59) How to manage effectively without micro-managing 

(17:11) The importance of intellectual honesty (18:32) Frank's thoughts on being 'in the arena' 

(21:04) What it really takes to build a viable business 

(28:34) Contrasting ServiceNow and Snowflake 

(33:40) The impact of AI on business 

(39:01) The future of app ecosystems 

(44:50) Becoming a student of leadership 

(46:31) Managing investor relationships 

(48:04) Why Frank doesn't think about his legacy 

(50:17) Closing Thoughts

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

My guest today is Sanjit Biswas, the co-founder and CEO of Samsara, a platform that helps companies digitize their physical operations. In 2023, Samsara reached $1 billion in ARR, making it one of the fastest startups in history to hit this milestone. 

But this wasn't Sanjit's first major success. Before starting Samsara, Sanjit left his Ph.D at MIT to build Meraki, a cloud networking company that Cisco acquired for $1.2 billion in 2012.

In our conversation, Sanjit shares his journey from grad school research to bootstrapping Meraki in the early days. He reflects on the lessons he learned from Meraki's pivot to the enterprise, the decision to sell to Cisco, and the insights that led him to start Samsara. 

We then turn to how Samsara found product-market fit, Sanjit's philosophy on allocating capital, and the areas where he believes generative AI will have the biggest impact. 

It was a really fun and insightful conversation that I think you'll enjoy!

(00:00) Intro
(00:16) Sanjit's background and the genesis of Meraki
(06:25) Meraki's pivot to the enterprise and rapid growth
(09:45) Lessons from building Meraki's enterprise sales motion
(16:15) The decision to sell Meraki to Cisco
(20:05) Founding Samsara and its mission
(27:11) Defining Samsara's product strategy based on customer feedback
(31:00) Samsara's unique journey to $1B in revenue
(39:16) Sanjit’s "70/20/10” framework for allocating capital
(43:13) The importance of board alignment and company culture
(50:58) Sanjit's thoughts on AI and hype cycles
(54:22) Sanjit's advice for aspiring entrepreneurs