Box CEO Aaron Levie joined the show to share his perspective on how AI is reshaping the enterprise landscape. He shared what his customers are actually thinking about when it comes to AI, the shift from closed to open-source models, and why the biggest opportunities might not be in flashy consumer tools but in workflow automation and data-rich enterprise applications.

Aaron also shares his take on the changing business model dynamics in B2B, including the rise of usage-based pricing, and what it means for the next wave of software companies.

00:00 Introduction to AI in B2B and Consumer Worlds

00:32 Conversation with Aaron Levy: AI in the Enterprise

01:10 Defining a Model Company and AI's Role

02:19 Challenges and Opportunities in AI for Enterprises

03:44 Open Source vs. Commercial AI Models

05:40 The Future of AI Agents

11:42 AI's Impact on Business Models and Pricing

15:16 AI's Potential to Transform Industries

27:14 Comparing AI and Cloud Adoption

30:05 Strategizing AI Implementation

31:08 Customer Adoption and Resistance

32:59 Practical Considerations and Challenges

34:58 Building Flexible AI Architectures

37:57 Exploring Agentic Workflows

41:57 Future of AI in Enterprises

43:36 Rapid Fire Questions on AI Impact

53:20 Exciting AI Features at Box

55:53 Conclusion and Final Thoughts

Being Black in Corporate America