Is Google’s search monopoly coming to an end? Alex Immerman, Partner at a16z, joins us to explore how generative AI tools like ChatGPT and Perplexity are reshaping the $200 billion search market. We discuss why users are shifting to AI-powered tools for direct answers, the growing legal and competitive pressures on Google, and the rise of verticalized search engines for specialized industries. Timecodes: 00:00: Introduction to the Search Market 01:20: The Rise of AI in Search 02:18: User Experience: Links vs. Answers 03:06: The Shift to Personalized and Conversational Search 04:45: Verticalized Search Engines 08:08: The Future of Search: Consolidation and Fragmentation 09:05: Enterprise vs. Consumer Search 09:51: Ad-Based vs. Subscription Models 11:16: Looking Ahead: Opportunities and Challenges Resources: Find Alex on X: https://x.com/aleximm Check out all 50 Big Ideas: https://a16z.com/big-ideas-in-tech-2025/ Stay Updated: Let us know what you think: https://ratethispodcast.com/a16z Find a16z on Twitter: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Subscribe on your favorite podcast app: https://a16z.simplecast.com/ Follow our host: https://twitter.com/stephsmithio Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.