The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg
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Jan 19, 2026 
Winston Weinberg, CEO and co-founder of Harvey, leads a discussion on navigating the dynamic landscape of AI in professional services. He shares insights on why enterprise AI adoption is lagging by 3-5 years and the vital role of model performance in this shift. Winston emphasizes the significance of building trusted relationships with investors and the need for effective company routines. He details his approach to deal-making, advocating for listening over negotiating, and reflects on the future of legal firms and the transformative impact of AI on the industry.
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Win Mornings With Early Hard Work
- Get up early and do hard physical activity to clear stress and improve decision-making for the day.
- Use the morning for focused product thinking before Slack and email flood in.
Fundraise By Building Trust Early
- Start fundraising six months early by selling small information-rights checks to build trust with target investors.
- Deliver on promises consistently so future rounds can close quickly without a full competitive process.
Consumer Plateau, Enterprise Acceleration
- Consumer-facing model performance may be plateauing because many consumer problems need app integrations, not better reasoning.
- Enterprise capabilities, especially code generation, will continue to improve fast and unlock productivity gains.