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Enterprise AI spending is soaring, but the financial payoff remains uncertain. In the latest episode of Breaking Analysis, theCUBE Research’s Dave Vellante and Crawford del Prete, former president of IDC and now senior adviser at PSG Equity, examine whether productivity gains can translate into meaningful returns for businesses investing heavily in AI. The conversation explores why improvements in individual tasks aren’t necessarily boosting company profits. Vellante and del Prete discuss the productivity J-curve, changing software business models and the importance of customer retention. They also examine how AI-native companies and established software vendors approach monetization as enterprise expectations continue to evolve. Infrastructure spending adds another layer to the debate. Vellante and del Prete examine financing, workload utilization, security and hybrid deployments, along with the shift toward usage-based pricing. Their discussion highlights what businesses need to prioritize to turn AI investments into sustainable revenue, measurable outcomes and stronger long-term financial returns. Read more: https://siliconangle.com/2026/10/31/can-enterprise-ai-pay-for-the-boom/ Find more SiliconANGLE news and analysis https://siliconangle.com/ Follow theCUBE's wall-to-wall event coverage https://siliconangle.com/events/ Learn about the latest theCUBE events https://www.thecube.net/ Be sure to follow Dave's weekly Breaking Analysis podcast as well, for the deep data dives on enterprise computing trends, from spending patterns to Wall Street implications. https://www.youtube.com/playlist?list=PLenh213llmcZMTRZKjnAwesSCiuLQT21E 00:00 - Intro 00:05 - Enterprise AI Productivity and Investment Returns 02:49 - Anthropic Financing and Enterprise Compute Commitments 07:03 - Matching AI Models to Workload Costs 11:01 - Competitive Pressure Forces Software AI Investment 13:14 - Enterprise Productivity Through Bottom-Up Workflow Redesign 20:06 - The Productivity J-Curve Explains Delayed Returns 22:43 - Workplace Technology Adoption and Organizational Dependence 27:46 - Internet Bubble Lessons and Security Investments 31:27 - Execution Judgment and Accountability in Software 36:05 - Enterprise Buyer Examples Expose Monetization Barriers 38:27 - Redesigning Software Companies for Efficient AI Deployment 42:28 - Usage Pricing and AI Monetization Challenges 47:17 - Sustainable AI Economics From Retention to Cash #theCUBE #BreakingAnalysis #theCUBEresearch #EnterpriseAI #AIeconomics #PSG

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