Chief Change Officer

#426 Waverly Deutsch: Love and Logic—Building Businesses That Actually Work—Part Two

37 min
Jul 9, 20259 months ago
Listen to Episode
Summary

Waverly Deutsch, former 22-year Chicago Booth instructor, discusses how balancing emotional passion (love) with logical analysis (logic) shapes entrepreneurial success across different cohorts—from undergraduates to executives. She explores how AI will transform coaching and business education, arguing that human relationships remain irreplaceable in building ventures despite AI's computational power.

Insights
  • Different entrepreneur archetypes require opposite coaching approaches: undergrads need process and logic to ground their passion; executives need emotional permission to think bigger and take calculated risks
  • The most effective coaching combines active listening with strategic reframing—translating entrepreneurs' stories back to them in more compelling, concise language builds trust and clarity
  • AI can polish business plans and pitches but cannot replace the homework, customer research, and relationship-building required for genuine entrepreneurial success
  • Entrepreneurship is fundamentally a process of identifying opportunities, marshaling resources, serving customers, and sustaining economic returns—this framework applies across all business models and education levels
  • The future of coaching and education must evolve to use AI as a human partner for enhancement, not replacement, particularly as generative AI disrupts traditional teaching methods like written assignments
Trends
AI-human partnership model emerging as the preferred approach in coaching and business education rather than AI replacementShift from teaching content/memorization to teaching critical thinking and research skills as AI commoditizes information deliveryGrowing recognition that pitch decks and business plans are relationship-initiation tools, not closing mechanisms—courtship metaphor replacing transactional sales approachIncreased focus on founder homework and customer validation as differentiators in investor meetings, as AI-generated materials become commoditizedExpansion of entrepreneurship coaching beyond elite institutions to diverse, underserved small business owners with varying education levelsRecognition that emotional intelligence and listening skills are becoming more valuable as AI handles logical/analytical tasksVenture capital evaluation shifting toward founder credibility and relationship fit as AI-generated business plans become indistinguishableTeaching methodology evolution: moving from assignment-based learning to experimentation and real-world problem-solving as AI handles content generation
Topics
Entrepreneurship as a structured processBalancing emotion and logic in business decisionsCoaching methodologies for diverse entrepreneur populationsAI's role in business education and coachingPitch deck and investor pitch strategyCustomer acquisition and market validationVenture capital fundraising dynamicsActive listening and communication skillsBusiness model scaling and growth strategyInnovation barriers in corporate environmentsFounder psychology and risk toleranceNew Venture Challenge program designInternational entrepreneurship and cultural diversitySmall business owner developmentHuman-AI collaboration in professional services
Companies
University of Chicago Booth School of Business
Deutsch taught entrepreneurship and innovation for 22 years; hosts New Venture Challenge program
Simple Mills
Founder Caitlin Smith pitched gluten-free baking mixes in New Venture Challenge; grew to billion-dollar valuation
Groupon
Referenced as example of venture-backed company that reached billion-dollar valuation through acquisition strategy
Whole Foods
Distribution channel discussed in Simple Mills case study as expansion opportunity
Betty Crocker
Mentioned as comparable company model for Simple Mills' potential market positioning
University of Chicago Polsky Exchange
Program through which Deutsch coaches small business owners in Hyde Park with diverse backgrounds
People
Waverly Deutsch
Primary guest; 22-year entrepreneurship instructor now independent coach and book author
Vizchen
Podcast host and interviewer; former Booth student with personal mentoring experience
Caitlin Smith
New Venture Challenge participant whose gluten-free baking company grew to billion-dollar valuation
Quotes
"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."
Waverly Deutsch
"You have to see the potential for the future, but also be able to figure out the tiny step by step that's going to allow you to build the foundation of a company that can reach that vision."
Waverly Deutsch
"When you're talking you're not learning. You learn when you listen."
Waverly Deutsch
"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."
Waverly Deutsch
"AI is never going to be able to build those kinds of human relationships. AI is never going to substitute for the homework you have to do until a good story that begins that conversation."
Waverly Deutsch
Full Transcript
Hi everyone! Welcome to our show, Chief Change Officer. I'm Vizchen, your ambitious human host. Our show is a modernist humility for change, for aggressive, in organizational and human transformation from around the world. This episode is the second part of our three-part series titled Love and Logic, featuring Wafely 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, delve into Wafely'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, will dive into a major chapter of her life, 22 years as Chicago Booth. There, she caught and coast a sharply focused group of highly logical talents, or deeply engaged in the passion for innovation change and entrepreneurship. Since leaving that structured academic environment, she has transitioned to her current role as a coach for 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, Wafely and I will also discuss the role of human coaches. In this still developing scenario, AI is the powerhouse of logic. While decent coaches like Wafely represent love, providing that essential human touch in the coachy process. Without further ado, let's get started. Now, let's dive into a significant chapter of your career as Chicago Booth. Where you've dedicated 22 years to teaching and coaching. The environment there was highly structured and the students ranging from college undergrad 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. 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 the passions for innovation, the change, and for entrepreneurship. What common challenges did you observe them face? That's the first part of my question. For the second part, given those challenges you 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 statements of individuals? That's a great question. I think that the cohorts and the individuals all faced some similarity of challenge and some difference of challenge. 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. 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 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 ideas is never mind. There's a lot of process that's layered on top of things in the corporate world that set 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. 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. So either profitability or fundability in the not profit world. It's a process, right? It's a process of evaluating opportunities. It's a process of testing solutions, each the process. So with undergrad, 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. And 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 brands, loyalty, comfort without having something that's really innovative, right? How do you overcome the liability of new? 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 set of complimentary qualities that are not for no time to have, which is both the vision and the execution, right? You have to see the potential for the future, but also be able to figure out the tiny step by step that's going to allow you to build the foundation of a company that can reach that vision. It is different across different cohorts, different people, whether they're in school or their entrepreneurs in the world, but certainly at Booth, dealing with a range of students from high school through Booth for a while, all the way to very senior season executives. It is your job as a teacher, as a coach, as a mentor to figure out where the strengths of weaknesses are and bring techniques, tools, and advice that balances the strengths of weaknesses for that particular individual. Can you share with us some specific examples? Let me start with some examples from the executive level MBA program. Very often, because they've been in the corporate world, they don't want to present anything that isn't absolutely doable, low risk. They feel super confident in, and so they say, if you give us $5 million to build out this software, we can generate $7 million in five years. I feel pretty comfortable that if you built out this software, you could get to $7 million in five years. That's, by the way, most companies never get to a million dollars in revenues. That's a pretty interesting company, but it doesn't create a return on investment for a $5 million investment. It's a mismatch of the resources you'll need to get there and the outcome that you're telling the investors you're going to be able to create for them. That's a very common story with the executive MBAs. We don't want to say that we can be a $50 million company, because we don't know if we can be a $50 million company. If you, the entrepreneur, don't believe that you can be a $50 million company, if you, the entrepreneur, don't believe that this is a powerful, disruptive high value add to your customers in such a way that if you're given this kind of capital, $5 million plus, that you can't bring it to market in a way that in five years gets you to $50 million, what's the investor going to think about the business? Yep. Then you have at the other end of the spectrum, the young entrepreneurs who are so excited about their product and they've showed it to their friends and their friends are so excited about their product. And they're like, if you give me $200,000 to put this product into the market, I will be a billion dollar company in five years. This is going to go viral. Everybody's going to want it. It's going to just catch fire and you say, okay, how does that happen? Can you show me an example where for so little money somebody's been able to get so big, so fast because the product was so exciting. And they'll say, Groupon got to a billion dollars in a year and I said, yeah, Groupon had tens of millions of dollars of venture back. They got there that fast by acquiring a lot of companies that took a lot of money. So what makes you think for a very small amount of money, you're going to be able to do it. That's the case where you're bringing the logic into it. In the case of we are only going to get 7 million. You got to bring their emotion into it. The excitement, the thrill, the fomo as it's called in Silicon Valley, fear of missing out. With the younger entrepreneur, you've got to bring the logic back into it. What's the step by step? Has anybody else done it? Is there a path that you can follow a playbook you can follow? You're definitely bringing different things in with the full time and part time MBAs. It could be a little bit of folks. I'll give you an example that I've used many times and I, Caitlin, forgive me if I'm getting this wrong, but I'm going to talk to you about the conversation that I had with the founder of Simple Mills, Caitlin Smith. Caitlin came to booth because she was working on a startup. She was working on making gluten-free baking mixes for people who suffer with celiac and gluten issues. And she had created using nut flour instead of many of the other gluten substitutes. I'm really fabulous muffin mix. I mean, it was delicious and I paint gluten-free baked goods, but I really liked her for muffins. She came and pitched in the New Venture Challenge class and she said, here's what I've done. Here's how I did it. I'm in about 13 health food stores in North Carolina. I've got another 14 signed up. So we'll be in 27 health care stores and healthy stores in North Carolina area. Thank you very much. And everybody's paused and said, what do you want from us? I'm not sure I want anything from you. I'm not sure I want to raise money for this. I'm not sure that I need anything from you. So the judges for the New Venture Challenge are angel investors, venture investors. They're thinking, okay, good luck to you with your nice little lifestyle business, but there's not much we can help you. 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 the mistake of this exercise, you imagine the possibilities. You think big. What? 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 good 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 defensive. 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 it? 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 at the reaction. She comes back later and she says, you know what? I'm going to try that. Let's maybe think about raising a couple hundred thousand dollars and for her second pinnitch in the class for the New Venture Challenge. She talks, 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. 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 $600,000. Guess what? Simple 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 heart. Let's work on the fear of the challenge of big. Let's work on what we really want to do with this 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 NBC is 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, NBC stands for New Ventured Challenge. That's what Waverly referred to in her example. And we see is a top-ranked flagship accelerated program for entrepreneurs. That's a program under Post-Key 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 and fireman of a business school. You are now an independent consultant in 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 the unique venture ideas. While some may resemble NBAs using more logic than passion than love, others might remind you of younger NBAs or even undergrids. Yet the audience you engage with now is much broader and more diverse. I'm curious about how you've adapted or skilled you approved 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 pictures and developing the 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 NBAs or executive NBAs, I've been exposed not only to the diversity of age groups and education levels, but also to business models from all over the world. The second NBA program is taught in Chicago, London, 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. 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. So, coaching entrepreneurs in the real world, outside of this world of exceptional levels of intelligence has to bring in to play a different set of challenges for me personally. One of the things that you have to be able to do as a teacher is explain things in a bunch of different ways for people who learn differently. You have to be able to teach things at different levels and you have to be able to adapt what you're doing for the capabilities of the person that you're doing at home. I am now coaching people with different backgrounds, different education, different levels, and I have worked with particularly through the Polsky Exchange, small business owners in Hyde Park, who have very different backgrounds and very different education, and in my coaching. I would think that's a gap for me, like doing that, that if I were to take on a lot of small business clients in Wyse Art Advisory, I would have to become attuned to the limitations that they face, the reality of their situation. Fortunately, the process of entrepreneurship is the same. You have to identify the opportunity, you have to marshal the resources, you have to serve the customer, you have to do it in a way that generates enough economic return that you can sustain the business. So, it's a matter of being careful about my vocabulary, my expectation that they have a grounding in things like accounting, or business strategy, or social media, I have to find out where they are and match them and meet them where they are. I think that the biggest skill that I've developed over my career that works for me in this setting is that I am a very active listener, that I hear what someone is saying, I make sure that I repeat back to them so that I'm understanding what they're presenting to me. That's how I will learn the language of different entrepreneurs of the kind that I have not encountered, extensively in my career at Booth. I think that's what I will do. You really are an excellent listener. I think part of that comes from the deep understanding of the situation at hand, and another big part is your communication skills. You're not just articulate, once you understand what someone is going through, you take the time to think and analyze before responding in a way that really resonates with them. I think that's what makes you such a good listener. It's not just about using your ears, but also engaging your brain, and then responding, thoughtfully. I can definitely vouch for that. Thank you. Thank you, because I take that is the critical skill set for learning. You learn when you listen, it's funny, I coach my entrepreneurs when they're pitching, particularly they're pitching in the practice rounds. Right? In the Q&A. Yeah, put it up. Yes, talking. Answer the question briefly, and either get more questions or get feedback because when you're talking you're not learning. 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 mouth 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 spend 10 or 15 minutes sharing the problems and situations, and I listen intently. Then, all the still efforts they've said into maybe 5 to 10 sentences. At most, they usually amaze and say, yes, exactly, that's exactly what I meant. It goes beyond verbal or written skills. That is 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. It's funny that you say that, because that's what I do for people, right? 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. 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? Is multilingual and has incredible computational abilities? With our theme of love and logic, where AI represents logic, and you as a human coach and body 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. Let me 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. Then you get into college, particularly nowadays, where you can now build an Excel spreadsheet. So what has happened to math and teaching math and the role of memorizing the period of 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 real in pitch deck using AI and it gets you a meeting with an investor. What's that conversation look like? I 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 in 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 exercise and 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 meaning with the investor is going to be a disaster. I'm actually writing a book right now. It's home picture pitch and entrepreneurs died to winning coffee dates with investors. And I used 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 for you. You're writing this pitch deck. You're creating this story. You're creating this messaging in order to intrigue somebody to want to know more to have a conversation with you. You can think of the new venture challenge, 10 minutes to pitch 15 minutes to answer Q and a like a half an hour coffee date. You've got to get the dinner date. You've got to get invited to that one hour meeting with the partners. And you don't get invested in after the dinner date. There's a courtship. Are you right for me? Am I right for you? Do the economics make sense? Does the market make sense? Does our partnership make sense? A Turk sheet is just an engagement ring. We still haven't decided to consummate the relationship. That's when the contracts are signed in the checks in the bank and guess what? You are now married to that investor. They now have a say in your business the way your spouse has a say in your life. Right? If marriage still does do us part, an investment is still exit do us part. AI is never going to be able to build those kinds of human relationships. AI is never going to substitute for the homework you have to do until a good story that begins that conversation that begins that relationship. It might help you impregn the writing of that story. It might help you clean up your deck, but it's never going to build that story for you. I think the smart people in AI are starting to talk about AI human partnership. Now does our job evolve to use AI to make us better? The human brain we've already talked about this is fire not billions of neurons. There's no computer that's doing the magnitude of what the human brain is doing. Quantum computing maybe has the potential to deliver some of that, but for the foreseeable future, generative AI needs to be a human partner, not a human replacement. We kick off today's episode with wavily sharing how her roles as a teacher, coach and guide have helped different kinds of entrepreneurs and business people strike the right balance between logic driven calculations and emotionally driven desires for new ventures. Then we shifted the angle, depth up and look into the role of human coaches in the age of AI. In this still developing scenario, AI is the powerhouse of logic, while seasoned coaches like wavily represent love providing the essential human hut in the coaching process. As we speed, we are already seeing a new wave of tech products called AI agents. So what will happen with this new norm? As wavily argues, building a business is fundamentally about building human relationships. She likens it to kosher, moving from one stage to the next. So while the future might be digital, human connections will remain at the part of business and personal growth. In the third part of our series, will come full circle and focus back on wavily herself. She is now more than a coach. She is an entrepreneur herself actively building her own new venture. She is a fascinating mix of her ever changing experiences. Stay tuned, we'll explore that in the next episode. Thank you so much for joining us today. If you like what you heard, don't forget, subscribe to our show, leave us top rated reviews, check out our website and follow me on social media. On this channel, your ambitious human host. Until next time, take care.