The Art of Coaching: What 22 Years at Chicago Booth Have Taught Waverly Deutsch About Love, Logic, and AI

Ever had a mentor who changed your life, or maybe a coach who wasn’t just a coach but more of a life-saver?

This is Part 2 of a special three-part podcast series titled “Love and Logic.”

This Pride Month, we’re celebrating the spirit of championing our true identities with a special three-part podcast series titled “Love and Logic.” Waverly Deutsch, a proud member of the LGBTQ community and a staunch advocate for women entrepreneurs, navigates her multifaceted identity with aplomb— from a theater lover to PhD, from a STEM major to MBA professor, and from retiree to a baby boomer coaching venture builder.

Waverly, often compared to “the Simon Cowell of the Chicago Booth New Venture Challenge,” is celebrated not just for her straightforward feedback but for coupling it with practical, transformative advice. It’s this combination of tough love and insightful guidance that has influenced her approach to teaching and entrepreneurship at WyseHeart Advisory.

Episode Breakdown:

00:23 — Continuing the Journey in “Love & Logic”: Picking up where we left off last episode, what can listeners expect from this one and the next?

2:57 — Two Decades at Chicago Booth: “Undergrads bubble over with innovation, while executive MBAs might hold back on creativity,” Waverly observes. Explore how she navigates the diverse challenges faced by students at a top school, applying her signature blend of love and logic in teaching and coaching.

8:57 — Case Study in Compassion and Calculation: Meet Katlin Smith, who evolved Simple Mills from a fledgling startup in 2012 into one of 2023’s most innovative food companies, as named by Fast Company. How did Waverly’s guidance play a role?

NVC = New Venture Challenge

18:07 — Coaching a World of Entrepreneurs: Transitioning from academic halls to the entrepreneurial arena, Waverly discusses the unique advantages and challenges of coaching a broad spectrum of innovators.

23:48 — The Art of Active Listening: “Excellent listening skills are crucial for effective learning and connecting,” says Waverly. She shares insights on engaging with entrepreneurs from diverse backgrounds.

27:11 — AI and Human Coaching: The Love and Logic Mix: While AI excels in logic, crafting flawless pitch decks and resumes, Waverly emphasizes, “Building a business is about fostering human relationships. AI might set the stage, but it’s the human touch that builds real connections with investors and employers.”

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Host: Vince Chan | Guest: Waverly Deutsch

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