Jeff S. | Leland

Jeff Stine

5.0

(13)

Admissions Committee at Chicago Booth

Works at Foundations Advisory

Successful clients at

Not currently taking new clients

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About Jeff

I've spent my life in high-stakes environments where leadership isn’t theoretical—it’s real, urgent, and consequential. I started my career leading soldiers in combat as an Army Ranger- and Airborne-qualified Infantry Officer, an experience that shaped my approach to leadership, decision-making, and building trust in the toughest conditions. After the military, I transitioned to finance, working in investment banking before co-creating and acting as Managing Partner of two venture funds. My work took me around the world, investing in mission-driven startups across 26 countries and helping entrepreneurs navigate the complexities of leadership, growth, and raising capital. Over the years, I’ve advised executives, startup founders, and investors, and served on multiple Boards—including as Chairman—helping teams make better decisions, align their cultures, and scale effectively. But leadership isn’t just about high-stakes decisions—it’s about clarity, structure, and making life easier for yourself and your team. I bring a systems-thinking approach to my work, helping clients shift from reactive problem-solving to proactive leadership. Whether I’m coaching founders, executives, or emerging fund managers, my goal is the same: to help them lead with confidence, navigate complexity, and get out of their own way. Outside of work, I live in Chicago with my wife, Karen. I’m an avid reader, a lifelong student of psychology and human behavior, and constantly thinking about how we can design better systems—whether in business, leadership, or life.

Why do I coach?

I coach because I’ve seen firsthand how mindful leadership can result in transformative change. Early in my career, I led soldiers in combat, where leadership wasn’t optional—it was the difference between success and failure, trust and chaos. Later, as an investor and advisor, I worked with founders and executives facing their own kinds of high-stakes decisions. Time and again, I saw the same patterns: leadership challenges weren’t about intelligence or effort—they were about structure, clarity, and making the right decisions at the right time. I coach because I know leadership doesn’t have to feel like an uphill battle. With the right systems and perspective, founders can stop putting out fires and start scaling with intention. Investors can make better decisions with confidence. Executives can build cultures that reinforce their values instead of contradicting them. For me, coaching isn’t about giving advice from the sidelines—it’s about helping leaders build frameworks that make their lives easier. I do this work because I know what it’s like to carry the weight of leadership, and I want to help others navigate it with confidence, clarity, and conviction.

Work Experience

Advisor

eighty2i

June 2023 - Present

Advising 82i and its clients on topics such as leadership, Board dynamics and best practices, strategic transactions, and organizational design & effectiveness.

Architect

Stealth Initiative in Science and Innovation

June 2023 - Present

Owner

Foundations Advisory

April 2023 - Present

Helping leaders achieve their audacious goals to have positive impact on the world. Primarily for emerging fund managers and mission-driven startups. Areas of support include: leadership & management, Board dynamics & best practices, strategic narrative & communications, fund structuring & operations & thesis development, strategic transactions, and organizational design & effectiveness.

Mentor

Obuntu Foundation

January 2023 - Present

Obuntu Foundation is a nonprofit on a mission to advance the next generation of Fund Managers. Obuntu is their support ecosystem, there to give them the knowledge, community, and resources they need to succeed. I teach a session to each class of Obuntu Fellows, and act as a mentor to emerging fund managers.

Investor

Gricd

October 2022 - Present

Investor and former Board Director

So Fresh

August 2022 - Present

Investor and Advisory Board Member

WellaHealth

April 2022 - Present

Investor and former Board Director

Viamo

September 2020 - Present

Investor and former Board Chair

Get It

April 2020 - Present

Investor

Sendy Ltd

April 2019 - Present

Class of 2019

Presidential Leadership Scholars

January 2019 - Present

The Presidential Leadership Scholars program is a partnership among the Presidential Centers of George W. Bush, William J. Clinton, George H.W. Bush, and Lyndon B. Johnson that brings together a select group of leaders who share a commitment to create positive change. Participants enhance their leadership abilities through interactions with former Presidents Bill Clinton and George W. Bush, administration officials, leading academics, and business and civic leaders.