Chief Change Officer
#223 Love, Logic, and a Reality Check: Waverly Deutsch on Changing for the Better – Part One
Mon, 10 Mar 2025
Welcome to Part 1 of “Love and Logic,” where Waverly Deutsch shows us how balancing passion and reason leads to real impact. Today, we explore her journey—how she carved her path and why she’s committed to helping others find theirs. In later episodes, we’ll cover her work at Chicago Booth and WyseHeart Advisory, where she dishes out “tough love for entrepreneurs.”Waverly is famous for her blunt yet brilliant coaching style—think “Simon Cowell of Chicago Booth,” but with actual solutions. She’ll tell you your business pitch makes no sense, then hand you a roadmap to make it airtight. If you’re looking for sugarcoating, look elsewhere. If you want to grow, listen in.Key Highlights of Our Interview:A Love for Theater and Logic“I fell in love with theater and acting as a child. My mother and I would go to the theater together—it was a special time for us. At the same time, I was good at math and logic puzzles. I ended up with two majors, one in theater and one in computer science. They were separate disciplines, but in my mind, I was always bringing them together.”The Gut-Driven Leap“At 29, with a fresh PhD, analysis didn’t guide my career move. Joining Forrester was pure gut instinct. I saw it as a chance to dive back into technology, learn from brilliant people, and expand my horizons—no spreadsheets, no market evaluations, just a leap of faith.”Academia or Impact? The Career Crossroads“Graduating with a PhD in theater history during a recession, teaching jobs were scarce. Colleges were cutting back on theater programs, and the research focus in humanities felt too esoteric. I wanted to do something more contemporary, more impactful.”Burnout and Breakthroughs“After nearly eight years at Forrester, experiencing explosive growth, an IPO, and 60-hour weeks, I needed a reset. By 1999, I was ready for a new direction and decided to approach my next move more strategically.”Empathy for Everyone“Emotions aren’t just a ‘women’s thing.’ I’ve sat with many men who’ve cried during challenging discussions. The key is understanding that emotions are human, not a weakness, and they have a place in even the most logic-driven conversations.”_________________________Connect with Us:Host: Vince Chan | Guest: Waverly Deutsch______________________--Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.10 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.130,000+ 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.12 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>140,000+ are outgrowing. Act Today.<<<
Chapter 1: Who is Waverly Deutsch and what is her unique teaching approach?
Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Our show is a modernist humility for change progressives in organizational and human transformation from around the world. Ten years ago, during the summer term of the executive MBA program at Chicago Booth, I had the pleasure of meeting today's guest, Waverly Deutsch.
She taught one of the standout courses in the executive program called Building New Ventures. In just a moment, I'll let Waverly introduce herself. But first, I would like to share a memorable memory that really sets her apart.
Throughout my extensive MBA studies at both Yale and Chicago Booth, where I completed the full-time and executive programs respectively, I've sat through countless lectures taught by highly intelligent scholars and well-experienced practitioners. Yet, Waverly is the only professor I've encountered who dared to use the word love in a business school classroom.
In the field of business education, dominated by discussions of numbers, strategies, formulas, and models, all the logical stuff, the concept of love has never surfaced in any curriculum or textbook I've come across. Yet, she bought it into our discussions on angel investing.
It makes you wonder, how does love fit into building a business, advancing a business career, and fulfilling our life's legacy? With that in mind, I've put together a three-part series called Love & Logic, featuring Waverly as our special guest. She will be sharing and exploring from three perspectives how the intricate balance of love and logic shapes our career decisions and life choices.
Today's episode zooms in on Waverly's personal journey, the love and logic that have guided her career path and experiences. In our next episode, which is about her being a teacher and expert guide, we'll dive into a major chapter of her career, 22 years at Chicago Bull.
There, she taught and coached a sharply focused group of highly logical talents, all deeply engaged in the passion for innovation, change, and entrepreneurship. From that structured academic environment, she has transitioned to her current role as a coach for a more diverse group of entrepreneurs. In the third part of our series, we'll come full circle and focus back on Waverly herself.
She's now more than a coach. She's an entrepreneur herself, actively building her own new venture. is a fascinating mix of her ever-changing experiences. Good morning, Wayfully. Welcome to my show. Good morning, Vince. I am thrilled to be here. Usually, I kick off our interview with a little introduction about my guest. Today, I'd like to switch things up a bit.
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Chapter 2: How did Waverly Deutsch balance theater and computer science?
I was browsing through the website of your new venture, Wiseheart, and a specific sentence really stood out to me. It said, as a young person, I had an enormous love for the theater and a passion for logic. Love and logic, what a fascinating combination. So Waverly, can you unpack that for us? Tell us, who are you really at the intersection of these two worlds?
Wow, what an interesting question to start with. I think a lot of people gravitate towards one or the other. And what I mean by that is we are taught that we have a right brain and a left brain and our right brain is rational and our left brain is emotional. But people have both sides of their brain and they're using both sides of their brain. So for me, the way this manifested as a child,
I fell in love with theater. I fell in love with performance. I fell in love with acting. I fell in love with theater. My mother and I would go to the theater together. It was a very special time for us. But at the same time, I was good at math and logic puzzles. And people would say, were you good at computer science? You have to remember, I'm fairly old.
We didn't have computers when I was growing up. As I was approaching my college years... And really thinking about what I wanted to do with college. I had done so much in high school with theater and so much in high school with many other subjects. Economics, psychology, math. I went to an excellent high school. And I was approaching my college years thinking I still want to do theater.
But I recognize in myself that I... don't necessarily want to have the kind of career where you have a job and then you don't, and then you have a job and then you don't, that I wanted something that would create stability for me. So I approached college saying, I'm going to do a dual major in theater and business.
And ultimately what happened was I had a conversation with a guidance counselor in my freshman year of college. He said, don't do an undergraduate business degree. Companies want MBAs and MBA programs want to teach you their methodology.
do something, do a deep dive in something that's related to business that you can leverage in the business world, but would also be a good foundation for going to business school. So I said, okay, I will take the computer science class for computer science majors instead of the one for business majors, and I will check out computer science. And
Again, being a child of the 70s and 80s, this is the very early 80s, I had not been exposed to computers before. And I fell in love with the logic of computers and how it was incumbent on a programmer to break something down into its fundamental elements to teach a computer how to do it. That's programming. I ended up with two majors, one in theater and one in computer science.
Computer science was starting to have an impact on theater. I had to learn how to program a lighting board, for example. But they were really very separate disciplines that I was bringing together in my own life and in my own mind.
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Chapter 3: What challenges did Waverly Deutsch face as a woman in computer science?
Anywhere from 20 to 35. Oh, okay. Yes. You're a hundred percent correct in thinking that it was very male dominated. I think today in college classes, in computer science, in STEM, you'll have a higher percentage of women, but it still won't exceed. It won't reach 50% in a lot of cases, but it was 5% at best when I was studying computer science.
I was very lucky in that the head of the computer science department at the University of Pittsburgh happened to be a woman. So I at least had visual role models because, of course, in computer science, most of my teachers were also men. So I did have a female role model to look to when I was a computer science student. I got along really well with the nerdy guys.
I've always had nerdy guys as friends. I have my nerdy side. I'm a science fiction fantasy fan. I cut school in high school to go see The Empire Strikes Back on its very first day in release with my friend Michael, who we called Zonar. I am a nerd, and I got along really well with my nerdy, computer science classmates, I also got along really well.
I have, I don't want to brag, but I have what I think is a fairly well-developed EQ from my mother. I got along really well in theater and I got along really well with my much more artsy feeling theater friends. They were two totally different worlds. They did not overlap at all.
The question of gender, I think, is a really important one in the conversation that we're having because you're talking about love and logic. And very often, love gets attributed to the feminine and logic gets attributed to the masculine. And they have always been a blend in my life. And I fundamentally believe that they are a blend in humanity.
that we artificially separate into, have to be honest, and maybe this is a little too much information for your podcast audience, but I do not comply with gender norms. I never have. I was a tomboy growing up. I am... tall for a woman. I wear my hair very short. I have a deep voice. I frequently get mistaken for a man. I identify 100% as a woman, as female. My pronouns are she, her.
But I have always felt this blend of the masculine and feminine in my life. And it goes right to this question of love and logic. So as a woman who had tomboy characteristics, that's what they would have been called in that day.
Even when I grew up, I'm younger than you by about 10 years. Tomboy was still a commonly used term in my generation. Don't forget, we're now in June 2024. The month of June is the month of Pride. So we are proud of our identities.
Yes, and I love that you bring in Pride Month because I think one of the amazing things to watch over the last... several generations is how the younger generations have embraced this gender ambiguity, gender fluidity that when you and I were growing up was not really available to us. Nevertheless, let's go back to this conversation of how I did as a female in the computer science department.
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Chapter 4: Why did Waverly Deutsch transition from academia to technology?
I did not love the research requirements of the theater history discipline. In the humanities, you have to publish on things that nobody has ever written about before, and you end up getting very esoteric. My dissertation is on the career of a woman named Laura Keane, who was a 19th century theater manager. She was the most successful woman to run a theater on Broadway in the 19th century.
She had her own troupe. It was in fact her troupe that was playing Our American cousin in Ford's Theater the night Lincoln was shot, she was the person who identified John Wilkes Booth, and no one has ever heard of her. And you get into these very esoteric topics. What does it mean to have been a woman theater manager in the 19th century?
And what happened to women theater managers as theater changed in the 19th century? And I started to realize these are not really impactful issues in... our day-to-day lives. I wanted something that was more current, more contemporary. But when I couldn't get a job as a junior faculty member in theater, I said, I am not going to stay in the world of academia.
I am going to return to the world of technology, which is much more pressing, more relevant now, again, beloved logic. I love the theater. I love teaching. But I don't love academia. I don't love a career as a humanities academic. I will go back to technology. Now, this is the early 90s. This is 1991, 1992. So technology's in a boom. It's in the very early stages of the internet bubble.
In fact, it's a little bit pre-bubble. It's as the internet is becoming part of our daily life, we're really using dial-up AOL or CompuServe. I'm having a conversation one night with a friend, and we're out to dinner with my partner and her husband, my friend's husband. We're having this conversation and she turns to her husband, she said, she'd be perfect for Forrester Research.
And I said, all right, what's a Forrester Research? I had never been in the business world. I had never thought about careers in business. And turns out he was an analyst for Forrester. They were a tiny little boutique market research company that looked at the impact of technology change on big business. Their tagline was helping companies thrive on technology change.
So why was this an unbelievably opportunistic moment? I call it luck, karma, fate, the world, just throwing open a door when you need one. If there's one thing a PhD proves that you can do, it's research. That is the fundamental thing that you do, right, as a PhD student. And I had a technology background. I knew how computers worked. I knew how to talk that language.
I could very quickly learn the modern technologies. And I joined Forrester as the first research associate that they had. Hired directly. The woman who preceded me had created the position. She had been an admin on the sales side. She created the position of research associate. I was the first person they hired into that job.
I went on to experience a growth company with the entrepreneur, founder, CEO still in place. We were less than $10 million in revenue. We were 20 people. I was employee number 27. There had been a little bit of modest churn and we went on our rocket ship. We had hired a new VP of sales out of IBM and he
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Chapter 5: How did Waverly Deutsch's career evolve at Forrester Research?
The founder CEO, still the CEO, personal friend, lifelong relationship. But I got to work very closely with him, see his journey, see what it means to scale a company, see what it means to take a product idea and turn it into reality. And that's where I fell in love with the entrepreneurial process.
While listening to you, I felt like we were having coffee together. Your story had me nodding, laughing, and utterly fascinated. You present this blend of strong analytical thinking with a very human, social side. Considering your career shifts and external pressures you faced, you mentioned some kind of luck or perhaps karma.
It got me thinking, how aware are you when it comes to making what you call calculated decisions? This ties into our theme of love and logic, the heart and the head. When you reach a critical point in your career path, how much do you lean on your analytical side? I'm not just talking about money or job titles, but evaluating the broader prospects of a position, diving deep into the industry.
How much of it is a calculated assessment? Or perhaps is it more about a gut feeling that tells you, hey, this is the right move. So do you consider yourself primarily analytical when making career decisions? Or do you tend to go with the flow? Or maybe you have your own unique approach or system for navigating these decisions. How does that work with you?
I love that question. And I think that it, for me, it changed very much over time. The moment in my life, I was 29 years old when I graduated with my PhD. The moment in my life where I had the opportunity to join Forrester, no analysis was involved. No examination of the job, the market size, the career potential, no analysis.
It was a gut feeling that this was an entry back into the world of technology that I wanted to get into. And a real sense that I could learn a ton from the people I met in my interview process. I could learn about business. It's not that I hadn't been working. I had only been doing a PhD. I actually taught for Stanley Kaplan test prep for 15 years. Was it 15 years? Oh, my goodness.
No, I guess it was about 15 years. From about 18 to about 29, so 11 years, teaching people to prepare for the GRE, the GMAT, the SAT exam. I had been working in the office at Stanley Kaplan. So I had been in the world of business education. But this was an entry back into technology. And there was no, is this the right job for me? Let me look at the market size, due diligence on the company.
This was, I am so lucky to have this opportunity presenting itself to me. Fast forward... I leave Full Rooster in 1999 and I take a much more strategic approach, a much more logical, thoughtful approach to what I want to do next. I see a career coach, get some skills assessments done.
I evaluate some jobs and realize that I don't want any of them as full-time jobs, but I enjoy the people that are coming to me. So rather than take another full-time job after recovering from my stint at Forrester, and I say recovering because we were growing so fast. We were working 50, 60 hour weeks. It was very stressful. We had gone through an IPO.
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