Craig Weiss is a leading Entrepreneur, Investor, and an Author. Currently, he is the Managing Partner of Flagstaff Ventures, where he brings entrepreneur-focused perspective to the venture capital field as one of the few institutional investors to have both built a unicorn as a CEO and also identified and invested in an early-stage startup that has achieved unicorn status. Craig has been a 3i Member since 2023.
In this episode, Craig discusses his experience writing two books on Israel's War of Independence, coining the concept of a "karmapreneur," and finding deep community value in Зі. He reveals how spiritual and commercial aims merge to create both financial and societal impact.

Listen to the podcast to learn more about:

Lessons from Authorship: Through archival research, interviews, and declassified military documents, Craig uncovered overlooked historical narratives-an approach he sees as mirroring the diligence required in startup investing.

Pivoting from Patent Attorney to CEO: How a background in patent law primed Craig for evaluating inventions and led to growing a vaping-tech startup that helped bring about a near smoke-free generation.

Integrating Business & Spirituality: Craig reflects on seeing seemingly different domains—venture investing, intellectual life, and moral purpose—as fundamentally connected, guiding his vision for future “karmapreneurs.”

Craig's Books:

• I Am My Brother’s Keeper: American Volunteers in Israel's War for Independence 1947-1949
• Fighting Back: Stan Andrews and the Birth of the Israeli Air Force

Documentary:

• Above and Beyond (2014 documentary featuring Craig Weiss)

Craig's Professional Links:

• Flagstaff Ventures (Craig Weiss's Venture Firm)
• Craig Weiss LinkedIn

Additional References from Conversation:

• Reason.com article covering Sen. Rockefeller’s vaping remarks
• Cast a Giant Shadow (1966 film about Mickey Marcus, mentioned in episode)

3i Members Links:

• 3i Members Official Website
• 3i Members LinkedIn