Jessica Robinson
Thinking · Current questions

For entrepreneurs and investors in an era of AI, what is the role of human judgment?

I don't have a framework for this yet. That is intentional.

In progress
Master of Applied Positive Psychology, University of Pennsylvania · Capstone ahead

Every company I work with is finding ways to create efficiency with AI. Some have slowed hiring or reduced headcount as a result. As an investor and board member, I urge the companies I work with to be as capital-efficient as possible. I have also spent years working on the workforce side of technology transitions.

I do not think either view cancels the other.

What interests me now is the person making the decision inside that tension.

The questions I am actually working on
What is good judgment, and how might we develop it among today's entrepreneurs?
What helps a founding team thrive through the hardest years of building a company rather than simply survive them?
How should boards think about resilience without turning it into another demand for endurance?
What does leadership require when increasingly capable software and machines become members of the operating environment?
What decisions should remain human as more of the world gets settled by defaults determined by machines?
Why Penn

Venture deals are partnerships that last ten years or more with founders. Yet I find the rooms I'm in have remarkably little language for the human part of that work: judgment under pressure, resilience, or what sustained performance actually requires.

I chose Penn, the home of positive psychology, to learn firsthand from the field's pioneers. I want tools to complement instinct. I'm inspired by research that shows the psychological capital elements of hope, self-efficacy, resilience, and optimism contribute to performance, stress management, and thriving.

My capstone is where I will take that work next.

In Detroit, this is not hypothetical

There is a Detroit version of the same question. Models for entrepreneurship, workforce transition, and community economic development demand people act under conditions of uncertainty, structural headwinds, and repeated setbacks. “Resilience” can be evoked as its own kind of judgment.

I want to understand what actually moves the needle, particularly in a city where the consequences of a transition are not abstract.

Contact

Write to me about a company, a question, or a room you are organizing.

hello@jessica-robinson.com
Detroit, Michigan
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© 2026 Jessica Robinson