Inside the Legal Tech Fund: Tom Dreyfus on Community, Courage & Climbing the Mountain
Update: 2025-11-07
Description
In this Careers and the Business of Law | Pre-TLTF conversation, David Cowen sits down with Tom Dreyfus, CEO and Founder of Josef, to unpack what it really takes to build and scale a legal tech startup from the ground up. From the first Legal Tech Fund investment to today's thriving TLTF community, Tom shares unfiltered insights on grit, growth, and redefining success beyond the 9-9-6 grind.
Key Topics Covered:
- The founder's journey: how Josef became the Legal Tech Fund's first portfolio company.
- Why relationships and listening matter more than capital in startup growth.
- The evolution from outsider to insider in the TLTF community and what that feels like.
- Why there are no shortcuts in building a meaningful business or reputation.
- The balance between grit and grace, navigating startup life and parenthood.
- How TLTF built a warm, human-centered community in an industry full of transactional events.
- A reflection on privilege, partnership, and progress in modern leadership.
🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!
💡To learn more about the future of legal innovation, visit https://cowengroup.com/
See you at TLTF!
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