In the fast-evolving world of legal technology, few stories capture the imagination like that of Harvey, the AI startup that’s reshaping how law firms operate. Founded by Winston Weinberg, a former lawyer turned entrepreneur, Harvey has skyrocketed to a $5 billion valuation, drawing attention from investors and industry watchers alike. Weinberg, who left a promising legal career to launch the company, attributes much of this success to disciplined personal habits that keep the operation lean and focused amid rapid expansion.

At the heart of Harvey’s growth is its mission to automate tedious legal tasks, allowing attorneys to focus on high-level strategy. Recent reports highlight how the startup’s tools are being adopted by major firms, with Weinberg emphasizing the need for human oversight in AI applications. As detailed in a Business Insider interview, Weinberg’s approach involves meticulous self-management to steer the company through its hyper-growth phase.

Mastering Time Through Calendar Audits

One of Weinberg’s key habits is conducting regular calendar audits, a practice he swears by for maintaining productivity. He reviews his schedule weekly, categorizing entries into core priorities like product development and team building, while eliminating low-value meetings. This method, he explains, ensures that every hour aligns with Harvey’s strategic goals, preventing the dilution of focus that plagues many scaling startups.

In the same Business Insider piece, Weinberg notes that these audits have helped him reclaim up to 20% of his time, which he redirects toward innovation in legal AI. This discipline echoes advice from tech leaders, but Weinberg tailors it to the unique demands of the legal sector, where precision and efficiency can make or break client outcomes.

The Art of Hands-On Hiring

Equally critical to Harvey’s ascent is Weinberg’s hands-on involvement in hiring, a process he oversees personally to ensure cultural and skill alignment. Rather than delegating to recruiters, he interviews candidates at all levels, probing not just technical expertise but also their passion for transforming legal work through AI. This approach has built a team of over 100 specialists, many drawn from top law firms and tech giants.

According to insights shared in an Observer profile, Weinberg views hiring as the foundation of scalable innovation, emphasizing the need for diverse talents who can bridge law and technology. He credits this method with fostering a collaborative environment that accelerates product iterations, such as Harvey’s specialized workflows for contract analysis and due diligence.

Navigating Challenges in Legal AI

Yet, growth hasn’t come without hurdles. Weinberg has publicly addressed criticisms, including a recent Reddit spat where he defended Harvey’s adoption rates with data on client usage. As reported in Business Insider, this incident underscored the scrutiny facing AI firms in regulated fields like law, where trust is paramount.

Weinberg’s habits also extend to broader leadership strategies, including investing in junior lawyers’ training amid AI disruptions. In a podcast appearance detailed by Sequoia Capital, he argues that tools like Harvey enhance rather than replace human roles, reducing burnout and elevating strategic work. This perspective has resonated, helping Harvey secure partnerships with global firms.

Looking Ahead: Sustaining Momentum

As Harvey eyes further expansion, Weinberg’s routines provide a blueprint for other founders in high-stakes industries. He plans to apply calendar audits company-wide, ensuring the entire organization remains agile. Meanwhile, his hiring philosophy continues to attract top talent, positioning Harvey to lead in AI-driven legal services.

Industry observers, including those at Yahoo Finance, note that with $100 million in revenue achieved in just 36 months—as per a Latka analysis—Weinberg’s methods are proving effective. By blending rigorous self-discipline with a deep understanding of legal workflows, he’s not just building a startup; he’s redefining an entire profession for the AI age.