Elad Gil’s Next Big Bet: AI-Powered Rollups in the Tech Landscape

Elad Gil, an early investor in AI, found his next venture focus on AI-powered rollups—an innovative approach to revamp traditional businesses. While many investors were just beginning to understand the impact of AI technologies like ChatGPT, Gil had already invested in promising startups such as Perplexity, Character.AI, and Harvey.
For the past three years, Gil has been contemplating opportunities to acquire mature, people-heavy companies like law firms, integrating AI to scale and enhance their profitability. His strategy is to leverage AI’s capabilities to automate repetitive tasks across different domains—ranging from coding to sales outreach—which can significantly boost profit margins. Gil posits that directly owning the businesses allows for quicker transformations than merely selling software.
So far, he’s invested in two companies employing this strategy, with one of them, Enam Co., focusing on worker productivity and already valued over $300 million.
Gil emphasizes that while there have been tech-enabled rollups in the past, the current AI landscape offers a genuine opportunity to significantly alter the cost structure of traditional businesses. The potential for growth through AI rollups intrigues him, particularly the unique leveraging of cash flows to acquire additional companies.
Despite the allure of this path, finding the right team compositions—balancing strong technological expertise with private equity knowledge—has proven challenging, as Gil has encountered many teams that still need to refine their strategies.
Investor interest in AI rollups is burgeoning, with firms like Khosla Ventures exploring similar strategies. Meanwhile, Gil remains passionate not only about financial gains but also about engaging with transformative technology.
With recent advancements in the AI market, he sees clearer victors emerging in various sectors, including legal, healthcare, and customer service. For example, his portfolio company Harvey aims to revolutionize legal proceedings using AI and is reportedly in talks to raise funding at a valuation nearing $5 billion.
Overall, this moment in AI represents both a significant opportunity and an exciting time for Gil, who continues to engage deeply with these technological shifts and the companies shaping the future.
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