Why AI Can’t See Most of the Web (Explained by the Founder Building the Fix)

Most leaders assume AI and search already see the whole internet. In reality, they all operate on the same tiny slice of the web. In this episode of IT Visionaries, host Chris Brandt sits down with Sudheesh Nair, Co-Founder and CEO of TinyFish and former CEO of ThoughtSpot, to unpack why only a small percentage of the web is indexable and how that cripples enterprise AI. Sudheesh explains why the next breakthrough won’t come from bigger models or better search, but from agents that can operate the web at scale, logging in, filling forms, running workflows, and surfacing the long tail of opportunities that never appear on page one. He also shares why human craft, taste, and presence will matter more than ever in an agent-driven world. Key Moments: 00:00 - The Deep Web Problem 02:48 - The Amazon Search Trap 04:26 - Why Search is Broken 07:01 - Internet is No Longer a Library 08:29 - AI Answers vs Blue Links 13:05 - Introducing Tiny Fish's Mission 16:00 - Search as a Poor Experience 18:29 - The Deep Web: APIs, Workflows & Logins 22:11 - Tackling the 93% Problem 25:47 - The Eight-Room Hotel Success Story 29:04 - Operating the Web vs Skimming It 32:42 - Real-Time Personalized Workflows 38:31 - Enterprise B2B Strategy 40:18 - Taste Over Tools 43:08 - AI Freeing Human Experience 46:36 - Travel Experiences & Local Discovery 50:00 - Democratizing the Internet 56:39 - The Waving Guide in China 1:01:12 - Optimism for AI's Future -- This episode of IT Visionaries is brought to you by Meter - the company building better networks. Businesses today are frustrated with outdated providers, rigid pricing, and fragmented tools. Meter changes that with a single integrated solution that covers everything wired, wireless, and even cellular networking. They design the hardware, write the firmware, build the software, and manage it all so your team doesn't have to. That means you get fast, secure, and scalable connectivity without the complexity of juggling multiple providers. Thanks to meter for sponsoring. Go to meter.com/itv to book a demo. --- IT Visionaries is made by the team at Mission.org. Learn more about our media studio and network of podcasts at mission.org. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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Why AI Can’t See Most of the Web (Explained by the Founder Building the Fix) is an episode from IT Visionaries by Mission.

This episode is 01:02:45 long.

This episode was published on Jan 22, 2026.

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