Chief Change Officer – Episode #426

Guest: Waverly Deutsch

Host: Vince Chan

Title: Love and Logic—Building Businesses That Actually Work—Part Two
Date: July 9, 2025

Episode Overview

This episode, the second in a three-part series with celebrated educator and entrepreneurial coach Waverly Deutsch, examines the nuanced interplay of love (empathy, encouragement, support) and logic (strategy, process, reason) in coaching entrepreneurs—and how this dynamic evolves in our AI-driven era. Vince and Waverly trace her journey from 22 years coaching at Chicago Booth to her current broader, more diverse coaching practice, discussing approaches to different entrepreneur profiles, how to sustain genuine human connection, and the irreplaceable aspects of human coaching even in a world augmented by AI.

Key Discussion Points & Insights

1. Love and Logic: Teaching Across Cohorts

[03:31–09:24]

• Challenge Spectrum:
  • Undergraduates are innovative but inexperienced—unhindered by “what’s impossible,” yet lacking foundational logic for process.
  • Executive MBAs are logical to a fault—over-cautious, incremental, and constrained by knowledge of bureaucratic barriers, often lacking bold vision.
• Coaching Style:
  • For undergrads: Teach structure, logic, and process to channel passion effectively.
  • For executives: Infuse emotion and vision, pushing them to imagine and communicate bigger possibilities.

Quote:

“With undergrads, you’re giving them the process... to learn to add the logic, the data, the research to their passions. It’s almost exactly the opposite with executive MBAs… you have to bring the emotion into it.”
— Waverly Deutsch, 07:13

2. Case Study—Simple Mills: Blending Heart and Head

[12:57–17:55]

• Example: Caitlin Smith, founder of Simple Mills, initially pitched a “small” business model. Waverly urges her, just for the sake of the class, to “imagine the possibilities”—could Simple Mills be the Betty Crocker of the 21st century?
• Outcome:
  • Caitlin moves from caution to ambition.
  • Simple Mills evolves into a billion-dollar brand, transforming gluten-free from niche to mass-market.

Quote:

“Why shouldn't Simple Mills be the Betty Crocker of the 21st century? What if, just for the sake of the New Venture Challenge, you modeled that out?”
— Waverly Deutsch, 15:39

Memorable Moment:

Caitlin’s visible discomfort and eventual willingness to think bigger — “I could see her getting defensive... Her team is literally chewing their fingernails.”
— Waverly Deutsch, 15:55

3. Transitioning from Academia to Coaching Entrepreneurs Globally

[18:04–24:17]

• Broader Clientele: Now coaching entrepreneurs of all backgrounds, ages, and education levels, far beyond the selectivity of Booth.
• Critical Adaptation:
  • Must tailor language, expectations, and teaching style to match client understanding—no assumptions about business savvy.
  • Strong emphasis on active listening: meeting clients where they are, reflecting their ideas back in clear, empowering ways.

Quote:

“I am a very active listener… I make sure that I repeat back to them so that I’m understanding what they’re presenting to me.”
— Waverly Deutsch, 24:01

Memorable Moment:

Waverly jokes, “I often joke with them that one of my strongest talents is translating English to English.”
— Waverly Deutsch, 27:17

4. The Art of Listening in Coaching

[24:17–27:39]

• Listening is not passive; it’s the key to learning and building trust.
• Coaches distill a client’s story and reflect it back, more powerfully, in their own words—building rapport and clarity.

Quote:

“You learn when you listen. … When you’re talking, you’re not learning.”
— Waverly Deutsch, 25:07

5. Coaching in the Age of AI: Love versus Logic

[27:39–34:50]

• AI’s Role: AI excels in generating logic, process, and content; it's a "powerhouse of logic."
• Human Coach’s Value:
  • Only a human can foster genuine love—empathy, encouragement, the nuanced relationship-building that is the heart of entrepreneurship.
  • AI can draft resumes or pitch decks, but only people can convince investors, partners, and customers through authentic relationships.

Quote:

“Building a business is a human-to-human engagement... AI is never going to be able to build those kinds of human relationships.”
— Waverly Deutsch, 33:44

• Business as Courtship:
  • Waverly analogizes entrepreneurship to dating—pitch decks get you “coffee dates," but lasting partnerships (aka investment) are built through trust and ongoing dialogue, not just logical presentations.

Quote:

“A term sheet is just an engagement ring. We still haven’t decided to consummate the relationship... An investment is till exit do us part.”
— Waverly Deutsch, 33:17

Notable Quotes & Memorable Moments

• On structuring coaching by client needs:

  “It is your job as a teacher, as a coach, as a mentor to figure out where the strengths and weaknesses are and bring techniques, tools, and advice that balances the strengths and weaknesses for that individual.”
  — Waverly Deutsch, 08:30

• On the core of coaching:

  “True listening is rare... Is about truly listening, capturing the essence of what they are saying and then reflecting it back to them in their own language.”
  — Vince Chan, 26:15

• On AI in entrepreneurship:

  “Generative AI needs to be a human partner, not a human replacement.”
  — Waverly Deutsch, 34:44

Timestamps for Key Segments

| Segment | Timestamp | |-----------------------------------------------|------------| | Introducing love and logic in entrepreneurship| 03:31 | | Undergrad vs Exec MBA challenges | 06:30 | | Simple Mills case study | 13:08–17:55| | Active listening and coaching approaches | 22:39–25:07| | Coaching as "English to English" translation | 27:17 | | AI vs Human Coaching—love and logic | 28:16–34:50| | Business as relationship-building | 32:19–33:47|

Episode Tone

Warm, direct, practical yet deeply human. Vince and Waverly speak candidly about both the logic (strategy, process) and love (courage, connection) required to build transformative businesses, maintaining a conversational tone laced with vivid real-world stories and down-to-earth humor. Their rapport is genuine, their wisdom hard-earned and open-handed.

Summary

• Waverly Deutsch recounts decades coaching elite entrepreneurs and how she’s adapted her blend of empathy and rigor from the halls of Chicago Booth to the wider, wilder entrepreneurial world.
• The episode provides both pragmatic frameworks and inspiring stories—a masterclass in how love and logic, when balanced, help people outgrow their limitations.
• While AI automates the logical, human coaches champion the emotional: inspiring clients to be bolder, listen more deeply, and build meaningful businesses and lives.
• Tune in next week for Waverly’s “full circle” journey—as not just a coach but a founder going through her own transformational new venture.