Jeff Stine

I help founders and leaders make high-stakes strategy, team, capital, and board decisions under uncertainty.

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I work with founders, executives, and innovation leaders facing ambiguity, pressure, and organizational complexity.

Across two decades in investing, finance, board work, and military leadership, I’ve helped teams navigate complexity, pressure, and change. For the past decade, I’ve worked as an early-stage investor and board member across startups and emerging technology companies, advising on strategy, org structure, hiring, roles and responsibilities, financing, governance, metrics, culture, and founder resilience.

I also bring this perspective to my work as an Executive in Residence at the University of Chicago Booth School of Business. Earlier, I worked in investment banking at Lazard and served as a U.S. Army Infantry Officer.

I’m most useful when a leader needs to cut through complexity, name the real issue, and leave with a clearer decision, framework, or path forward.

Chicago, Illinois
Startup & Venture Building

Services

Start Here: Free 15-Minute Fit Check

Bring one strategic, organizational, investor, or leadership issue. We’ll clarify the problem, identify the best next step, and determine whether a deeper advisory session would be useful.

15 minFree
Pressure-Test a High-Stakes Decision

For leaders deciding what to prioritize, whether to pivot, what to stop doing, where to place resources, or how to move forward when the data is incomplete.

1 hour$300.00
Prepare for a Board, Investor, or Financing Conversation

For founders who need to sharpen their story, anticipate hard questions, clarify the ask, or align financing strategy with their growth plan.

1 hour$300.00