Chief Change Officer
#124 Waverly Deutsch’s Coaching Wisdom: 22 Years of Love, Logic, and AI at Chicago Booth
Fri, 27 Dec 2024
Ever had a mentor who became more than just a coach, someone who changed your perspective and your path? This is Part 2 of “Love and Logic,” our special three-part Pride Month podcast series celebrating authenticity and transformation. Waverly Deutsch, a proud LGBTQ advocate and champion of women entrepreneurs, shares her incredible journey—from theater enthusiast to PhD, STEM major to MBA professor, and now, a venture-building coach and founder of WyseHeart Advisory. Known for her candid yet constructive feedback, Waverly’s tough love inspires transformative growth for entrepreneurs worldwide. Key Highlights of Our Interview: Blending Heart and Head “Whether it’s calming executives’ cautious approaches or reining in overly ambitious young entrepreneurs, success lies in balancing heart (vision) with head (practicality). It’s about building a compelling story that resonates with both emotions and logic.” Executives: Breaking the Incremental Mold “Executives often pitch ideas that feel safe but lack innovation. They’re so aware of corporate barriers that their creativity gets stifled. My role? Push them to think beyond incremental improvements and aim for groundbreaking changes that truly stand out.” “Executives often present highly calculated plans—‘$5 million investment for $7 million returns.’ While safe, it doesn’t excite investors. Encouraging them to aim higher, to envision $50 million, injects the passion and ambition their pitches often lack.” Unleashing Undergraduate Imagination “Undergraduates are brimming with ideas because they haven’t yet encountered the roadblocks of the corporate world. The challenge is teaching them the process—how to take their boundless creativity and add logic, research, and structure to turn dreams into sustainable ventures.” Overzealous Optimism Meets Reality “On the flip side, young entrepreneurs brim with optimism, promising billion-dollar outcomes for modest investments. The challenge? Bringing logic into their bold dreams—helping them see the steps, resources, and realistic pathways to scale.” The Power of Experimentation “Sometimes, all it takes is encouraging an entrepreneur to think bigger—just as an exercise. That simple shift in perspective can unlock enormous potential, as it did with Simple Mills, now a model for blending passion and pragmatism to scale innovation.” _________________________ Connect with Us: Host: Vince Chan | Guest: Waverly Deutsch ______________________ --Chief Change Officer-- Change Ambitiously. Outgrow Yourself. Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs, Transformation Gurus & Bold Hearts. 6 Million+ All-Time Downloads. Reaching 80+ Countries Daily. Global Top 3% Podcast. Top 10 US Business. Top 1 US Careers. >>>100,000+ subscribers are outgrowing. Act Today.<<< --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.18 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 1.5% Podcast.Top 10 US Business.Top 1 US Careers.>>>170,000+ are outgrowing. Act Today.<<<
Chapter 1: What is the focus of this podcast episode?
Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chan, your ambitious human host. Our show is a modernist community for change progressives in organizational and human transformation from around the world. This episode is the second part of our three-part series titled Love & Logic, featuring Waverly Deutsch as our special guest.
Here, she explores from three perspectives how the intricate balance of love and logic shapes our career decisions and life choices. The last episode delved into Waverly's personal journey. looking into the love and logic that have guided her career path and experiences.
In this episode, which focuses on her role as a teacher and expert guide, we'll dive into a major chapter of her life, 22 years at Chicago Booth. There, she taught and coached a sharply focused group of highly logical talents, all deeply engaged in their passion for innovation, change, and entrepreneurship.
Since leaving that structured academic environment, she has transitioned to her current role as a coach for a more diverse and larger group of entrepreneurs. Throughout my personal experience, having both official and unofficial mentors and coaches has been profoundly beneficial. It's not just about the outcomes, but the process.
And more importantly, I've learned so much from the real life experiences of humans. My supervisors, teachers, colleagues, classmates, and even my life partner, who was once my teacher. These individuals have provided me with immense love and helped me refine my logic. human experience has always been critical to my personal and professional development.
As we enter the age of AI, Waverly and I will also discuss the role of human coaches. In this still developing scenario, AI is the powerhouse of logic. while seasoned coaches like Waverly represent love, providing that essential human touch in the coaching process. Without further ado, let's get started.
Now, let's dive into a significant chapter of your career at Chicago Booth, where you've dedicated 22 years to teaching and coaching. The environment there was highly structured, and the students, ranging from college undergrads to full-time MBAs about mid-20s and late 20s, and executives who are mid-30s to mid-40s, all of them represented a distinctly logical and talented group of people.
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Chapter 2: How has Waverly Deutsch influenced her students at Chicago Booth?
Many of these students, like myself, came from very strong corporate backgrounds where we were primarily trained to think with our heads over our head. With that in mind, I'm curious about your perspective about them. They came to you very eager to explore and explode their passions for innovation, for change, and for entrepreneurship. What common challenges did you observe them face?
Chapter 3: What common challenges do young entrepreneurs face?
That's the first part of my question. For the second part, given those challenges you've identified, How have you leveraged your own experiences to guide them? Do you find yourself offering more love, i.e. emotional support, over logic, i.e. calculated strategies? Or is it a mix of both? or depending on individuals or segments of individuals?
That's a great question. I think that the cohorts and the individuals all face some similarity of challenge and some difference of challenge. So I'll give you an example. The undergraduate population is hugely innovative because they haven't gone out into the work world yet to see the obstacles that are put in the path of creativity. Right. So we all think about innovation in a large corporation.
Have you done your homework? What's the market analysis? Do we have the resources for this? And, oh, by the way, we have to get approval from 17 layers of corporate to even have a conversation about this or create a working group about this. And eventually, the person with the idea is, never mind. There's a lot of process that's layered on top of things in the corporate world that...
sets up obstacles to innovation i think that every corporation is aware of and battles as they want to become more innovative but also that people become aware of as they progress in the work world so that being said the undergraduates don't know what's possible they don't know what's impossible they don't have the foundation for a lot of that logic and so the chat with them is to give them
a process and I believe entrepreneurship is a process. It's a process of taking an idea or identifying an opportunity and turning it into an organization, a company, a not-for-profit that brings a specific type of value to a specific community in a sustainable way, right? So either profitability or fundability in the nonprofit world, it's a process, right?
It's a process of evaluating opportunities. It's a process of testing solutions. It's a process. So with undergrads, what you're really doing is you're giving them the process by which they can learn to add the logic, the data, the research to their passions. It's almost exactly the opposite with, say, the executive MBAs. The ideas often...
Lack innovation and lack creativity are incremental to the way things are being done because they are so aware of the barriers to innovation, the challenges of getting new things through. But then you say, why does the world need a company? A tiny bit incrementally better than the way you've seen things done in the past, right?
So it's really hard to break through brand loyalty, comfort, without having something that's really innovative, right? How do you overcome the liability of newness? So you're right that a balance...
that you have to use between managing a person's tendency to go with their heart versus their tendency to go with their head to help them bring those two things together in the sense of complementary qualities that an entrepreneur has to have. which is both the vision and the execution, right?
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Chapter 4: How do emotions play a role in entrepreneurship?
They're thinking, okay, good luck to you with your nice little lifestyle business, but there's not much we can help you with. So Caitlin and her New Venture Challenge team and I were sitting in a conference room and I was saying to her, Caitlin, I understand that you haven't thought about taking on money and scaling this business and that you're not even sure that's what you would want to do.
But you'll get the most out of this learning process and you'll get the most out of the resources of the coaches and mentors and judges that we put in front of you. If just for the sake of this exercise, you imagine... the possibilities. You think big. What could this look like if you did want to take on venture capital money? If it was available to you, what's the upside?
What's the biggest you can imagine? Because to me, this shouldn't be just in health food stores or on gluten-free shelves. This is a Very delicious, healthy breakfast option for anybody who wants higher protein, higher fiber, good for you muffins. So to me, this should be on every grocery store shelf. What's the biggest independent baking goods company you can think of in the 20th century?
And she immediately said Betty Crocker. And I said to her, 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? What would that look like? What capital would it require? What distribution channels would you use? And I could see her getting excited. I could see her getting a little angry.
I don't know if that's what I want to do. Why are you making me think about being like, I could imagine the things that are going on behind her eyes. Her team is literally like chewing their fingernails. They've tried to have this conversation with her. I can tell that they're really nervous about her reaction. She comes back later and she says, you know what? I'm going to, I'm going to try that.
Let's maybe think about raising a couple hundred thousand dollars. And for her second pitch, she, in the class for the New Venture Challenge. She starts to talk about distribution at Whole Foods, and she starts to have conversations with people at Whole Foods, and she starts to think about the fact that gluten-free is coming on other...
grocery store shelves and maybe there is bigger distribution and maybe with a few hundred thousand dollars she can expand the number of skus or number of products she's offering so she pitches that at the second round and she gets selected to go into the finals and by the finals she's really thinking about a seed round of six hundred thousand dollars guess what temple mills is a
Billion-dollar valuation company. It is in every grocery store you can imagine in the United States. They've gone from baking mixes to snacks, cookies, crackers, all gluten-free. Caitlin is still the CEO of that company. It is remarkable what she's accomplished. And that was really a... Part, let's work on the fear of the challenge of big. Let's work on what we really want to do with this.
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Chapter 5: What is the importance of balancing heart and head in innovation?
And head, what's possible? What's your model? How would you do it? And by opening up just the completely low-risk experiment of just pitch it in the NVC as a big business, it enabled her to bring her heart and head together around a very different business than the one she had imagined coming into the process.
For listeners, NVC stands for New Venture Challenge. That's what Waverly referred to in her example. NVC is a top-ranked flagship accelerator program for entrepreneurs. That's programmed under Polsky Center for Entrepreneurship and Innovation at the University of Chicago. I'll attach the web link in the show notes in case anyone is interested.
Now, let's step away from the structured environment of a business school. You are now an independent consultant and coach. You are not dealing with a defined group of talents. The world has become your client base. Entrepreneurs of varying ages, generations, and cultures and educational level eat with their unique venture ideas.
While some may resemble MBAs using more logic than passion than love, others might remind you of younger MBAs or even undergrads. Yet the audience you engage with now is much broader and more diverse. I'm curious about how you've adapted or scaled your approach in this new role
How do you tailor your methods to meet the needs of such a varied audience, especially when it comes to refining their pitches and developing their venture ideas?
Great question. I think that Having had 22 years of experience with the incredibly diverse populations of the best and brightest high school kids that I worked with in a summer program, the kids that choose the University of Chicago. undergrad folks who come for MBAs or executive MBAs, I've been exposed not only to the diversity of age groups and education levels.
Also, I've been exposed to business models from all over the world and new ventures from all over the world because the executive MBA program is is taught in Chicago, in London, in Hong Kong, and draws from all over the world. The University of Chicago is well known for having a very large international cohort of students. So our undergrad, I believe, is close to a third international.
Our graduate programs are very international. This foundation of exposure to people in business models from all walks of life really feeds into what I do now. I think the... biggest gap in my experience is the fact that every single person that I've dealt with through the University of Chicago has been incredibly bright, right?
We're talking about top tier intelligence, the high school students that were chosen for the program, the people who get accepted into the University of Chicago, the people who get accepted into the Booth School of Business. We're talking about exceptionally bright people. So the basic level of intelligence is very high.
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Chapter 6: Can you share an example of a successful entrepreneur's journey?
Good.
Absolutely. As a coach, I've realized that true listening is rare. We often hear about the importance of listening skills on social media. But ironically, social media by itself is a one-way means of communication. Switching back to coaching, I've done a fair amount of coaching myself. working with entrepreneurs and professionals.
What I've noticed is that I can make a strong impression right from the first meeting. Often, the subject spends 10 or even 15 minutes sharing the problems and situations, and I listen intently. Then I'll distill everything they've said into maybe 5 to 10 sentences at most. They're usually amazed and say, yes, exactly. That's exactly what I meant. It goes beyond verbal or written skills.
It's about truly listening, capturing the essence of what they are saying. And then reflecting it back to them in their own language. That's how they realize, wow, you really get me. That's how you build trust as a coach. That's been my experience.
Yeah, it's funny that you say that because that's what I do for people, right? So when I'm helping them tell their story, I listen to their story and then I tell it back to them in a way that's more concise, powerful and compelling. And they're like, can you just pitch it for me? I often joke with them that one of my strongest talents is translating English to English.
I don't know any other languages. Unlike you, Vince, I am not multilingual, but I am a really good English to English translator.
Do you think AI could be your competitor in coaching? It's multilingual and has incredible computational abilities with our theme of love and logic. where AI represents logic. And you, as a human coach, embody love. How do you see AI supporting your coaching effort? And on the flip side, how could it possibly diminish the distinctiveness of your skills?
I think that's a fantastic question. I am Super glad that I got out of teaching at the time when generative AI is emerging on the market. I think teaching is going to have to change dramatically. The written assignment. I remember when I was growing up, we memorized the multiplication tables. When we get to high school, they say, okay, now you don't have to do your long division.
Now you don't have to do it all on pencil and paper. You can finally use a calculator. We needed you to learn how to do it so that your brain would actually understand what the calculator was doing for you. Right? But you can now use a calculator. And then you get into college, right? particularly nowadays, where you can now build an Excel spreadsheet.
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Chapter 7: What lessons can be learned from Caitlin Smith's experience?
So what has happened to math and teaching math and the role of memorizing the multiplication tables is what's now happening with English, right? What's happening with language. Not just English, but any language. And that is, I can prompt a chat GPT to write a paper on Moby Dick without even reading the book.
If I don't read the book and write the paper, my brain is not actually growing into the pathways that... Reading and thinking and doing your own analysis allows it to do. And then every kid's paper about Moby Dick says exactly the same thing. How the world is going to deal with this is completely beyond me, but I'm really glad it's not my problem to solve.
So let me go to the question that you asked. How do I think it relates to the coaching? Ultimately, building a business is a human-to-human engagement. You have to acquire customers. You have to take care of those customers. You have to have stakeholders who believe in you, who help you build your business.
You have to have investors that you report to, and you have to have a deep understanding of your business to succeed in all of those things. So let's imagine that you create a brilliant pitch deck using AI, and it gets you a meeting with an investor. What's that conversation look like? I'm convinced that we're in a world now, particularly around HR, Where AI is going to write my resume.
I'm just going to answer questions about what I've done in my life. And an AI is going to write my resume. And I'm going to ship it off to a company where an AI is going to evaluate my resume. And when it rejects my resume, I'm going to feed my resume through an AI that understands why resumes are accepted or rejected. And I'm going to submit a different AI written resume.
resume that's going to pass the ai standards i'm going to find myself in an interview with the hiring manager i'm not going to have the slightest idea what my resume says how it was positioning me how it was presenting me what's going to happen what's the interview going to look like that's where entrepreneurs are
AI can absolutely help them write a polished business plan that appears to answer all of the questions.
But if they haven't done the research, if they haven't figured out what the analogs tell them, if they haven't interviewed the customers, if they haven't attempted the exercises, experiments in social media marketing that will help them figure out what their customer acquisition cost is going to be, if they haven't done the work... The meeting with the investor is going to be a disaster.
I'm actually writing a book right now. It's called Fix Your Pitch, An Entrepreneur's Guide to Winning Coffee Dates with Investors. And I use the dating analogy, the dating metaphor throughout the book to say, you're not creating a pitch deck. You're not creating a 10-minute presentation. You're not creating a story. Because someone's going to hear your 10-minute pitch deck and write a check.
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