Greg Whalen (CTO, Prove AI): Why Most AI Projects Fail Before Production episode artwork

EPISODE · Jun 9, 2026 · 43 MIN

Greg Whalen (CTO, Prove AI): Why Most AI Projects Fail Before Production

from Liftoff with Keith Newman: For Founders looking for a new growth playbook and further inspiration. · host Journalist, Startup and GTM whiz Keith N hosts the #1 Podcast for Super founders

In this episode, Keith sits down with an AI infrastructure leader to unpack what is really happening behind the current AI boom.While most conversations focus on models and hype, this discussion goes deeper into the engineering realities of building reliable AI systems at scale.The conversation explores why observability, telemetry, debugging, and system architecture are becoming critical as enterprises move from experimentation to production AI.They also discuss why terms like “agentic AI” are often misunderstood, why many AI projects end up being rebuilt from scratch, and why the future competitive advantage may come from the tooling built around models rather than the models themselves.Topics covered include:Why most AI systems fail due to poor observabilityThe real engineering challenges behind enterprise AIWhy “agentic AI” may be the industry’s most overused termThe shift toward commoditized foundation modelsWhy telemetry and debugging will define reliable AI systemsThe underrated founder skill of ignoring distractionsWhat the AI stack could look like by 2028This episode is a practical conversation about the difference between AI demos and real AI infrastructure.Sponsor Info: We are strategic business advisors with decades of leadership experience and a proven track record of driving businesses’ growth. We specialize in creating custom-tailored strategies to introduce your company, drive growth, build leadership teams, and ensure companies implement appropriate compensation programs. Our mission is to utilize our expansive network to benefit your company https://www.compass-strategic-advisors.com/Connect with Greg Whalen: Website: https://prove.ai/ LinkedIn: https://www.linkedin.com/in/greg-m-whalenDiscord Server (Multi-Agent Systems Engineering Group) - https://discord.gg/sXpr2Hh Subscribe for more founder insights and hit the bell for notifications! Follow us on our channels for exclusive startup content and behind-the-scenes insights from interviews like this one. Spotify: https://open.spotify.com/show/3cFpLXfYvcUsxvsT9MwyAD?si=f5a14e779777487d Apple Podcasts: https://podcasts.apple.com/ca/podcast/liftoff-with-keith-newman/id1560219589 Substack: https://keithnewman.substack.com/ Newman Media Studios: https://newmanmediastudios.com/ LinkedIn: https://www.linkedin.com/company/liftoffwithkeith For sponsorship inquiries, please contact: [email protected]#AI #ArtificialIntelligence #EnterpriseAI #MachineLearning #SoftwareEngineering #AIInfrastructure #StartupGrowth #Leadership #FounderMindset #TechLeadership

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Greg Whalen (CTO, Prove AI): Why Most AI Projects Fail Before Production

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