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OpenAI’s Multi-Billion Ad Strategy, Modal Labs CEO on AI Infrastructure, Twilio’s Voice AI Surge

May 26, 2026

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Polymarket’s Regulatory Hurdles, Pre-IPO Betting Boom on Prediction Markets, AI Increasing Workloads

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Episode Description

E-commerce reporter Ann Gehan talks with TITV Host Akash Pasricha about OpenAI's rapid push into conversion-oriented ads ahead of its anticipated IPO. We also talk with Modal Labs CEO Erik Bernhardsson about the company's new $4.65 billion valuation and infrastructure roadmap, and we get into Twilio's stock performance and voice AI agent risks with Financial Analysis Columnist Anita Ramaswamy.

Articles discussed on this episode:

https://www.theinformation.com/articles/twilios-ai-boost-double-edged-sword

https://www.theinformation.com/articles/openais-next-ad-move-going-small-scale-big

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Chapters:

00:00 - Introduction

01:13 - OpenAI Scales Conversion Ads and Targets Small Businesses

08:26 - Modal Labs CEO Erik Bernhardsson on $4.6B AI Infra Roadmap

16:10 - GitHub’s Maintenance Issues and the Need for AI Native Code Tools

25:19 - Twilio Defies the SaaS Apocalypse on Voice AI Hype

29:26 - Usage-Based Pricing Risks & Telecom Cost Pressures on Twilio

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