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American Focus > Blog > Tech and Science > Early AI investor Elad Gil finds his next big bet: AI-powered rollups
Tech and Science

Early AI investor Elad Gil finds his next big bet: AI-powered rollups

Last updated: June 1, 2025 12:59 pm
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Early AI investor Elad Gil finds his next big bet: AI-powered rollups
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Elad Gil, a prominent venture capitalist, has been at the forefront of investing in artificial intelligence (AI) long before it became a mainstream trend. His early bets on startups like Perplexity, Character.AI, and Harvey have proven to be successful, positioning him as a key player in the AI space. However, Gil’s focus has now shifted towards a new opportunity: using AI to revolutionize traditional businesses and scale them through roll-ups.

The concept behind this strategy is to acquire established, labor-intensive businesses such as law firms and professional services firms, implement AI technologies to enhance their operations, boost profit margins, and then acquire similar businesses to repeat the process. This approach, which Gil has been pursuing for the past three years, aims to leverage AI to transform repetitive tasks into software, thereby significantly increasing profitability and creating more efficient enterprises.

Gil explains that by owning the business outright and improving its gross margins from 10% to 40%, one can generate substantial cash flow, allowing for the acquisition of other companies at higher prices. This increased cash flow provides a competitive advantage, enabling the execution of roll-up strategies that would be challenging for others to replicate.

Two companies backed by Gil are actively pursuing this AI-driven roll-up strategy. Enam Co., a worker productivity-focused startup, has garnered significant valuation from investors like Andreessen Horowitz and OpenAI’s Startup Fund. Gil believes that using AI in this manner can fundamentally alter the cost structure of businesses, distinguishing it from previous technology-enabled roll-up attempts that lacked true technological innovation.

While Gil’s track record includes successful investments in companies like Airbnb and Coinbase, the effectiveness of his AI roll-up strategy remains to be seen. The key challenge lies in assembling the right team with a balance of technical expertise and private equity acumen, a combination that is not always easy to find. As more venture capital firms explore similar opportunities, Gil may face increased competition in the market.

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Despite the potential financial gains, Gil emphasizes that his motivation stems from a genuine passion for technology and progress. His hands-on approach to working with AI technologies, such as GPT-3, reflects his deep engagement with the industry. With a dedicated team of engineers, Gil continues to explore AI front-end companies and monitor their performance closely, leading to valuable insights and informed investment decisions.

As the AI landscape evolves, Gil identifies clear winners in sectors like legal, healthcare, and customer support, including his own portfolio companies like Harvey, Abridge, and Sierra AI. These companies are at the forefront of developing innovative AI solutions that are reshaping their respective industries. Despite these successes, Gil remains cautious about declaring victory, recognizing the dynamic nature of the AI market and the need for ongoing innovation to stay ahead of the competition. The landscape of AI startups is rapidly evolving, with only a handful emerging as the likely winners in each vertical. What was once a crowded field of two dozen promising companies has now narrowed down to just three or four per sector. This consolidation signals a maturation in the industry, where the map of success is becoming more defined.

Despite this shift, it’s not the end of the game. Rather, it’s a sign that the competition is heating up, and only the strongest players will survive. Venture capitalist Gil sees this moment as an exciting time filled with opportunities for growth and innovation. He views it as more than just another investment cycle, recognizing the profound impact AI will have on reshaping industries across the board.

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Gil’s position at the intersection of two major transformations – the future of AI and its implications for other sectors – provides a unique vantage point. He believes that navigating this dynamic landscape is thrilling, as companies must adapt to stay ahead of the curve. In a rapidly changing environment, those who can effectively integrate cutting-edge technologies will thrive while others may struggle to keep up.

In an upcoming episode of the StrictlyVC Download podcast, Gil will delve deeper into topics such as setting guardrails, overcoming gatekeeping challenges, and maximizing the potential of transformative technologies within businesses. This insightful discussion promises to shed light on the strategies that will define success in the era of AI-driven innovation. Stay tuned for more insights from Gil and other industry experts as they navigate the ever-changing landscape of technology and entrepreneurship.

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