#425 Waverly Deutsch: Love and Logic—Building Businesses That Actually Work—Part One

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Hi everyone, welcome to our show, Chief Change Officer.

I'm Viz Chen,

your ambitious human host.

Our show

is a modernist community for change progressives in organizational and human transformation from around the world.

10 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 Boo, 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 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 boarded 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 lives' legacy?

With that in mind, I've put together a three-part series called Love and 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 Boom.

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.

It is a fascinating mix of her ever-changing experiences.

Good morning, Waverly.

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.

I was browsing through the website of your new venture, Wise Heart,

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, well, you're 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 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.

As you indicated, that was late 70s and early 80s.

There must be very, very few females in your computer science class.

How did you navigate this deeply men-dominated world?

You're 100% right that in the early 80s, the late 70s, early 80s, I was

one of three or four women women in my classes in my computer science classes

women of course

one of sorry

you're saying one of the one of three or three or four women in the advanced computer science class like how many students were in in that class

anywhere from 20 to 35.

okay yes you're 100 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 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 be 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 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.

I was accepted by my male colleagues and

I thrived.

I did very well.

You asked a follow-up question.

What then took you back to theater?

Yep.

So I loved computer science and I loved programming, but I'm not a solitary person.

I'm a social person.

When I was thinking about what I wanted to do after college, I was pursuing a couple of different tracks.

I had the good fortune during college to be awarded twice the Provost Scholarship to Teach.

And one of the times I taught in the theater department and one of the times I taught in the computer science department.

I knew that what I wanted to do was teach.

That was truly my calling.

And if you think about a marriage of love and logic, if you think about a marriage of theater and computer science, being able to structure a subject in a way to present it to people, but then to present it with a little bit of theatricality, a little bit of entertainment, a little bit of humor to make it more interesting, more intriguing, more engaging as a subject for learning, this is where these two things came together in me.

So as a senior in college, I was applying for graduate degrees, I was applying for fellowships, and I was applying for jobs.

And I was offered jobs in the computer science department of ExxonMobil, in the leadership training program of

what was then MetLife Insurance, in the computer science departments of Digital Equipment Corporation.

But I won a Mellon Fellowship in the humanities to pursue my PhD so that I could teach.

That's what took me back to theater.

I really wanted to teach.

And I thought that the way to be able to teach was to do a PhD.

And I ended up doing a PhD in theater history.

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Teaching has always been your calling.

But I was wondering during this journey

from PhD to teaching.

There's something called Forester.

I believe you joined this firm and helped it grow from a boutique into a major institution over a couple of years.

You joined as employee 20-something, 27, I believe that's what you told me.

So with your calling for teaching, with your PhD degree, you could have stayed in the university building your academic career from assistant professor to associate to a tenure professor, a very well-predicted career path.

Then, what happened in between?

We'll talk about Chicago, your teaching career, 22 years teaching careers in Chicago, but before that, let's talk about what happened in the 90s.

Yeah, my career is nothing but a new example for twists and turns.

It's an excellent question.

How do I end up at Forest?

Graduating with my PhD, we were at the height of the late 80s, early 90s recession, and the baby boomers kids hadn't reached college age.

College enrollments were plummeting.

I was a theater historian.

That's what my PhD was in, theater history.

And colleges were cutting theater programs.

You had to maintain your acting program.

That's what

students came for.

But you could shave down classes like theater history and allow the English department to teach Shakespeare.

You could use the English department to cover some of the theater curriculum.

And so

there were no jobs.

Every job I was applying to was 200 to 400 applicants, many of whom had been tenure track faculty who had lost their jobs, right?

And so they were applying for the few available jobs.

At the same time, I was realizing that

while I loved the teaching part and I had taught at Tufts University where I got my PhD.

I had taught as a graduate student.

I loved that part of my job.

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 Keene, who was a 19th 19th century theater manager.

She was the most successful woman to run a theater on Broadway in the 19th century.

She had her own troop.

It was in fact her troop 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.

So 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 is in a boom.

It's in the very early dages 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.

And

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 forester research.

And I said, I'll bite.

What's a forester 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 Forester.

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 teacher.

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

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 revolutionized the approach to go-to-market and sales.

And the company took off.

And we were the first company to tell

Fortune 1000, chief technology officers, chief information officers, you have to pay attention to the internet.

And that was what put us on the map.

We were working.

in the early days that I joined with their transition from big mainframe computing to client server computing and the PC and the role that the PC would play.

And we were establishing ourselves as a leader in technology market research, but it was really our call around the internet that

took Forrester to the public company that it became and is today.

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 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, loving, 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?

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 that 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 for you?

I love that question, and I think that it for me 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 I actually taught for Stanley Kaplan test prep for 15 years.

Was it 15 years?

Oh my goodness.

No, I guess it, yeah, it was about 15 years from about 18 to about 29, so 11 years teaching people to prepare for the GRE, the GMA, the SAT.

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 Forrester 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, you know, it was very stressful.

We had gone through an IPO.

We had reached 200 million in sales and 400 people in the company all in the seven and a half years I was there.

So I took a little break after I left Forrester.

Instead of joining any one company, I decided I would create a small consulting company and work with all of these companies.

an independent consulting company, work with all of them at some level or

large companies on their e-commerce strategy, internet companies on their go-to-market, technology companies on raising funding from venture capitalists.

I did some consulting to see what kind of work I really liked and to see if there was a company that I wanted to throw in with full time.

So I went from

as a 29 year old, leaving one field that I had deep experience in, the academic field, and getting into a new field and literally just taking the leap based on a leap of faith, that I had this opportunity to join this company, that I really liked these people and knew I could learn a lot.

Fast forward 10 years, almost 10 years, and I'm taking a very different approach to what I want to do next.

There are two other words that perfectly capture the essence of love and logic: they are heart and head.

Can you recall a pivotal moment or a situation when you were torn between following your heart or your head?

What ultimately guided your decision then?

Wow.

I want to tell you a story that I haven't actually told a lot of people about

when I learned

how to manage the conflict between heart and head.

And the time at Forrester

with the entrepreneurial CEO George Colony

was

fabulous and I learned an enormous amount and I grew enormously.

But it was also when I had to confront this hearthead challenge.

Many of us

hate confrontation.

We hate having to deliver bad news or

have a difficult conversation.

We hate it.

And when I

get frustrated, when I

have to face confrontation,

I get teary.

And I was having an incredibly hard conversation with George

about my role at Forrester and my future at Forrester.

And I started to cry.

And George didn't know what to do.

And he wanted to end the conversation.

And I literally said to the man,

George, I can cry and think at the same time.

We can have this conversation.

Yes, I am having tears because my emotions are involved in this incredibly important logical conversation.

We are human beings.

We have emotions.

and we have logic and I can think and cry at the same time.

And for me, that was an extremely liberating moment.

Because in the past, I had always tried to get through the thinking situation and then go off and burst into tears.

That had happened to me when I found out at Tufts that I had passed my exams, my PhD exams, and I was going to be awarded my PhD degree.

The way that the head of the department presented it to me was hateful.

He said, we expected much more of you than this.

And if we could give you a pass minus, we would give you a pass minus.

And had been taking care of a partner who was suffering from chronic fatigue.

And I had been working a job at Stanley Kaplan and I had been studying for my exams and I was emotionally exhausted.

And I said to him, Did I pass?

And he said,

yes.

And I said, thank you.

And I ran downstairs into the bathroom and burst into tears.

To be able to have the confrontation with George and to cry and to have logic and to have a successful outcome was an amazing moment for me in learning that both things can happen at the same time and both can come into play at the same time.

And I think a lot of people

especially women, our emotions tend to be a little bit more at the surface than a lot of men experience.

Although, believe me, I've known a lot of men have sat with me and cried

that this gift of being able to say you can have your emotions and we can have this important, logic-driven discussion at the same time was a really critical moment for me in my evolution as a professional and as a human being, to tell you the truth.

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Growing up, I learned a straight rule.

No crying at work is simply unprofessional.

That was the norm in all the places I've worked and studied, both in the US and abroad.

But let's be real, whether you are a man or a woman, we are human and humans have emotions.

Crying is simply one way we express those emotions.

I believe that as our views on gender roles continue to evolve, it's becoming clear that we also need to rethink our attitudes towards showing emotions in the workplace.

I think that just to comment on what you said, I think one of the biggest myths that we've created in the world of business is, hey, it's not personal, it's just business.

But people...

Businesses are made of people and people are human and they have emotion.

And I also think it's, we're learning that a lot of our emotional sense is tapping into

some

subconscious knowledge that is actually leading us in a better direction than the purely analytical, right?

So no entrepreneur has enough data to make a purely analytical decision.

You have to go with your gut.

The one time that I accepted a job based on the logic of it, the title, the career path, the money, the benefits, the moment in my life where I needed to establish myself in Chicago because I had moved from Boston.

But there's this little red flag in my emotions saying, I don't know about these guys.

There's this little tickle in my gut that I don't know about these guys.

The one time I went with head, it was a disaster.

and lasted six months.

I parted ways with the company.

My intuition about the guys was right.

Ultimately, the VCs that backed the founder of the company had to remove him as CEO and claw back some of their money and allow the business model to change without him.

And so the one time that I actually made a career decision with my head rather than my heart, it was a disaster.

And I think I learned a lot from that.

I think ultimately,

the emotional side of you, the intuitive side of you, you know, what Malcolm Gladwell writes about in Blink

is accessing the fact that our brains are firing off billions of neurons.

We can't keep up with it at a conscious level, but our gut can, and our gut is telling us things that are important to listen to.

And

that's the thing that drives entrepreneurs is the need, the emotional need to do this business, to see if it will work, to bring this value to

improve the world with

a service or an innovation or a technology.

I am firmly in the camp of do all the logical analysis and don't do something that is clearly stupid.

But when ultimately faced with that choice, if your gut is telling you,

this is where I got to go.

And if this gut if your gut is telling you, this is a bad idea, listen to it.

There's a piece of the love and logic puzzle I haven't talked about much yet.

So far, I've discussed following your heart as a standalone element.

But our hearts,

they are heavily influenced by our peers, the people around us, and the social environment we're in.

Take my MBA classmates.

For example, among my classmates, I am the outliner.

Most of them are in finance.

CEO, CFO, senior bankers, senior management consultants, managing partner at PE and VC houses.

If I had stayed long enough at certain companies, I would have ended up in those roles as well.

But I make different choices along the way, guided by both heart and head.

The reason I bring up my own story at this juncture is that I've noticed many people struggle not just with the emotional versus logical decision-making, also with not seeing role models who reflect their aspirations.

There's also often a deep-seated fear of judgment and fear of failure.

These fears influence our hearts and ultimately impact our decisions.

I'm curious about your experience.

How much have external factors like peer pressure, societal judgments, or even social norms influenced you?

You mentioned earlier that you aren't bound by gender norms.

But what about other societal expectations?

How have you managed to filter out the noise and make your laws of change along your career path?

I think you're 100%

right that

our emotions and our heart are influenced by the people around us.

And in fact, there's a lot of evidence that community

is one of the primary sources of happiness in life.

So being able to find a community that supports you and that accepts you is one of the big challenges of people's lives.

And the way that community views you, right, being accepted by that community, like you said, by your peers in graduate school or in the career world or, you know, that's an important part of life and happiness.

I would argue that it doesn't just affect the heart, that it affects the head, that the very value systems that we're using to appraise things from a so-called logical standpoint salary title right career potential use of our talents all of those are based on societal judgment factors that are all driven by society peer upbringing community so i 100 agree with you on the incredible importance of other people humans are a social animal I might disagree with you on that it hits the heart and not the head.

I think it defines a lot of both.

That being said, for me,

one of the things that I think gave me the kind of resilience that I've had in my career and my life

is the fact that I grew up in a fundamentalist Christian household and I had to separate from my community, the community that I grew up with.

the people that I grew up with.

I had to accept myself

as non-conforming with what I had been taught as a kid was right, normal, appropriate.

In fact, made into a life or death decision.

And by doing that, by having as a very young person,

a young teen and a teen, having to give up community, give up, even give up family for a while, it made me more resistant to heavy influence by outside community forces.

It made me more able

to listen to myself, my own values, my ethnic system, my moral system,

and be less judgmental about things like my career, to be able to leave a career in which I was experiencing some success and make a huge change where I had to go back to the beginning again.

not something that was supported by my graduate school friends, my the people who knew me as an academic and as a thought leader in a particular field.

And

I think that

having to lose a community and having to rebuild the community gave me a sense of not a complete inoculation to what other people think about what I'm doing, but much less strength in that particular pressure on me and my life.

We begin today's interview by exploring Waverly's personal journey.

intricate blend of love and logic that has guided her from her undergraduate days all the way to retirement.

To our listeners, I hope today's episode inspire you to integrate your own love and logic in whatever paths you choose to pursue.

In our next episode, which is the second part of our three-part series.

We'll dig deep into a significant chapter of Waverly's career, her 22 years at Chicago Booth.

There, she taught and coached a selected group of highly logical talents, undergrads, full-time, part-time, and executive MBAs from around the world.

all of whom were passionate about innovation, change, and entrepreneurship.

Yet, despite their brilliant, these individuals face their own challenges.

Waverly has learned to tailor her coaching approach, sometimes offering a bigger dose of love, other times amping up the logic.

How exactly did she manage this?

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 to subscribe to our show, leave us top-rated reviews, check out our website, and follow me on social media.

I'm Viz Shen, your ambitious human host.

Until next time, take care.

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