Logan sits down with Bipul Sinha, CEO and co-founder of Rubrik and former VC at Lightspeed and Blumberg Capital. Bipul shares what he learned transitioning from investor to founder, why intuition beats expertise, and how he built Rubrik into a category-defining business by betting on uncool ideas. They talk product-market fit in the AI era, what most VCs get wrong today, and why the enterprise IT market is still just getting started. It’s a conversation packed with hard-earned wisdom and bold takes on building lasting companies.

(00:00) Intro
(01:42) Transitioning from VC to Founder
(02:27) The Genesis of Rubrik
(03:30) Navigating Uncertainty in Business
(06:57) Product Market Fit and Early Success
(08:56) Evolving with the Market
(13:14) AI and Data Security
(18:53) Leadership and Intuition
(28:34) Building a Transparent Culture
(31:52) Handling Tough Questions in Board Meetings
(33:28) Changing Perspectives Over Time
(34:57) Traits of Successful Entrepreneurs
(36:46) The Future of Venture Capital and Startups
(40:38) Balancing Forward and Lateral Motion in Business
(42:35) The Impact of AI on Various Industries
(01:00:28) The Evolution of Work and Technology
(01:02:52) Fostering a Collaborative Company Culture
(01:04:56) Looking Ahead: The Future of Rubrik

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing and editing: Justin Hrabovsky

Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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About the Show

Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.