Coburn Ventures Podcast #258: AI Workshop, Part 2 - Three Modules
9 snips
Mar 5, 2026 They unpack three workshop modules for partnering with AI to surface uncommon investment questions. They explain giving AI your investment DNA and using multiple stakeholder lenses. They show tactics like many short answers, selective deep dives, and iterative complaining to refine AI outputs.
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Treat AI As A Partner Not A Tool
- Partnering with AI (not just using it as a tool) unlocks a qualitatively bigger jump in uncommon understanding for investment work.
- Pip argues framing AI as a partner enables exploration beyond single answers and expands the possible insights available to investors.
Do A Type Three Error Question Check
- Run a Type Three Error check by asking AI whether you have the right question, why it might be wrong, and to propose 3–7 better pivotal questions.
- Pip recommends feeding full context then asking: do we have the right question, why, and list alternative pivotal questions (3/5/7).
Use Role Lenses To Simulate Stakeholders
- Use the lenses module: prompt AI to take roles (regulator, head of sales, procurement, competitor researcher) and surface uncommon, role-specific questions and tripwires.
- Brynn and Pip suggest simulating multiple stakeholders to reveal granular daily decision points and unseen risks quickly.