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Early AI investor Elad Gil finds his next big bet: AI-powered roll-ups | TechCrunch

Jun 02, 2025 - techcrunch.com
Elad Gil, a prominent venture capitalist, has been investing in AI startups like Perplexity, Character.AI, and Harvey before the technology gained widespread attention. He is now focusing on using AI to transform traditional businesses, such as law firms and professional services, by improving their efficiency and margins through AI-driven roll-ups. This strategy involves acquiring mature, people-intensive businesses, enhancing them with AI to boost profitability, and then using the increased cash flow to acquire additional companies. Gil believes this approach can significantly alter cost structures and create new business models.

Gil has backed companies like Enam Co., which focuses on worker productivity and has been valued at over $300 million. He acknowledges challenges in finding the right team composition for roll-ups and potential competition from other investors. Despite these challenges, Gil remains optimistic about the transformative potential of AI, citing clear winners emerging in sectors like legal, healthcare, and customer support. He emphasizes his passion for technology and progress, noting that the current period of rapid change is exciting and offers numerous opportunities for innovation.

Key takeaways:

  • Elad Gil is focusing on using AI to reinvent traditional businesses and scale them through roll-ups, aiming to transform mature, people-intensive outfits like law firms and professional services firms.
  • Gil has backed companies like Enam Co., Harvey, Abridge, and Sierra AI, which are leveraging AI to improve productivity and efficiency in various sectors such as legal, healthcare, and customer service.
  • He believes that AI can radically change the cost structure of businesses, allowing for increased margins and the ability to acquire other companies at higher prices due to improved cash flow.
  • Gil emphasizes the importance of having a strong team composition for successful roll-ups and acknowledges the potential challenge of competition from other investors pursuing similar AI strategies.
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