Chief Change Officer
#225 Love, Logic, and a Reality Check: Waverly Deutsch on Changing for the Better – Part Three
Wed, 12 Mar 2025
We’re closing out Love and Logic with a powerhouse—Waverly Deutsch, the theater-loving, PhD-earning, startup-coaching dynamo. A fierce advocate for LGBTQ and women entrepreneurs, Waverly doesn’t just give advice; she gives strategies that work. At WyseHeart Advisory, she’s proving that retirement isn’t about slowing down—it’s about lifting up the next generation with tough love and a little bit of stage presence.Key Highlights of Our Interview:A Coach’s Secret Weapon“The key to trust and transformation in coaching lies in active listening. People often speak in long, winding narratives. The magic is in boiling it down to the core message—a few sentences that make them feel truly understood and heard. By distilling and refining, you don’t just hear—they feel heard, understood, and empowered to act.”AI Can Polish, But Can’t Replace the Human Spark“AI can help craft a polished pitch or refine a resume, but it can’t simulate the deep understanding and personal experience that resonate in real-life interactions. The investor meeting? That’s where your own knowledge and authenticity come into play.”The Dating Analogy for Entrepreneurs“Pitching to investors is like dating. The 10-minute pitch? That’s the coffee date. The in-depth meeting? That’s the dinner date. The term sheet? That’s the engagement ring. True commitment comes when the contracts are signed and the check is in the bank.”The Age and Cost Equation“Older professionals face a harsh reality: companies often trade senior salaries for multiple junior hires. This economic shift means adapting, whether through freelancing, consulting, or pursuing entirely new avenues of work.”Consulting as the Bridge“Many transitioning entrepreneurs find opportunities as consultants. Whether it’s an interim CFO role or building sales strategies, the key is to be willing to revisit foundational work while leveraging years of expertise to establish credibility in new ventures.”_________________________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: What is the main focus of this episode featuring Waverly Deutsch?
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. If you've been following closely our special three-part Love & Logic series, you know this episode is the final session, the finale of our trilogy, so to speak.
Today, we'll come full circle and refocus on Waverly herself. She spent 22 years teaching at Chicago Booth, where one of her signature courses was building new ventures. Now, she is building her own venture called Wiseheart. In this episode, you'll hear her pitch. As you listen to our conversation, put on your entrepreneur coach hat and ask yourself, How compelling is her pitch?
She'll discuss the why behind her actions, what Wiseheart is exactly, who the target customers are, and how she plans to help these people. Lastly, where the name Wiseheart originated. If you're just joining this series, I strongly encourage you to check out the previous two parts.
We started the series by focusing on Waverly's personal journey, the love and logic behind her career path and experiences. Then in part two, we explored a significant chapter of her career, 22 years at Chicago Bull. There, she taught and coached a well-defined group of highly logical talents who were passionate about innovation, change, and entrepreneurship.
From that structured environment, we transitioned to discussing her current role as a coach for a broader and more diverse group of entrepreneurs. We also touched on the topic of AI human coaching, where AI serves as the powerhouse of logic. While AI can create flawless pitch decks and resumes, Waverly emphasizes that building a business is about fostering human relationships.
AI might set the stage. but it's the human touch that builds real connections with investors and employers. Let our finale begin. Let's dive into your newest venture, Wiseheart. I'm really curious about how you plan to continue supporting entrepreneurs with this new initiative. Over the years, you've coached and judged so many entrepreneurs. So for a moment, let's switch gears.
I'll put on my coach's hat and step into the shoes of a new venture challenge judge. Imagine you're now pitching Wiseheart to me. So tell me, what exactly is Wiseheart? What's the core mission there? Whose problem are you trying to tackle? I'd like to learn more about the specific characteristics of the people you're trying to help.
More importantly, how are you going about addressing their challenges?
Awesome. I think that... The best pitches talk a little bit about momentum and traction and a little bit about the reason for the existence of the business. As a wise heart advisor, I am an operating partner with OCA Ventures, a venture capitalist in Chicago. I'm an advisor to Pace Healthcare Ventures, a venture capitalist in Chicago.
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Chapter 2: How does Waverly Deutsch define her new venture Wiseheart?
I'm working with anywhere from half a dozen to a dozen entrepreneurs actively in the everything from building their business strategies and processes to raising money. That's what I'm doing with Wiseheart. Wiseheart was started not because I wanted to build a scalable company and sell it for $100 million. Wiseheart was started because I was retiring.
And what that means to me, what retirement means to me is that you no longer have to work in order to cover your basic necessities, to keep your benefits, to have a steady paycheck, but the work you do because you want to do it. And some of that work might be remunerated, paid for, and some of that work might be volunteer, and some of it might be purely recreational.
And your job in retirement is to figure out the balance that you're looking for across those three dimensions. So that's my definition of retirement. I knew I was going to continue to support entrepreneurs. I knew I was going to continue to work with venture capitalists. I'm passionate about that work. I love it. Highly personally rewarding.
And though I feel like I may be working more hours than I worked as a professor at Booth, particularly when I was focused on the EMBA program where the work came in spurts, right? You know, as you know, their classes are very intensive for short periods of time. and I'm making a tiny fraction of what I was making as a fully employed professor, I'm having more fun than I've ever had.
Chapter 3: What is Waverly's vision for Wiseheart in supporting entrepreneurs?
So Wiseheart was a place to put all of that work, an LLC for tax purposes where I could get paid. It was never intended to be a business that makes me millions of dollars. Why Wiseheart? Because I love working with entrepreneurs. I love working with innovators. I love working with investors. Who is my target customer?
My target customer is entrepreneurs who have a really great business who are struggling to bring it to market. That means that I might have a session with you and turn you down as a client because I don't think that either the business or you or the market is compelling. And as an independent consultant, I have the ability to do that, to say no to customers. And I have done that.
I said, this is not a business that I think I can add value to because I don't believe in it. Wiseheart is for early stage companies. and investors who invest in early stage companies. Not interested in taking on corporate innovation clients, not interested in helping a very large growth company get their series D. That is not my skillset. That is not my passion.
But my passion is to help entrepreneurs who have really great business concepts and really great business capabilities bring their products and services to market in the best way possible. I also want Wiseheart to be more accessible to entrepreneurs for whom the rest of the ecosystem is less accessible. So let's talk for a minute about women entrepreneurs.
There's a big statistic that everybody likes to use that women entrepreneurs get 2% of VC dollars. And that's a little bit misleading because the truth of the matter is that Women-only teams of entrepreneurs get 2% of venture capital dollars. Mixed-gendered teams get another anywhere from, depending on the year, 13% to 18% of venture capital dollars.
But that still means that 80% to 85% of venture capital dollars are going to all-male teams. All male founding teams. So there's a lot of room there for improving the way the venture capital world sees opportunity with female entrepreneurs and funds opportunity with female entrepreneurs. I would like to spend more of my time with female entrepreneurs, and I do.
At Booth, I spent more of my time with male entrepreneurs simply because the population of Booth is more male than it is female. Now I can choose. I can spend more of my time with female entrepreneurs than male entrepreneurs. By the way, guys, if you're listening, I have lots of male clients. I do not turn down male clients, but I can make myself available to women, men.
Minorities, minority entrepreneurs, people of color, people from rural areas, people who come from less affluent backgrounds. These are all people who struggle more in the process of building relationships. Businesses that require outside funding. I would like Wiseheart to serve more of those kinds of entrepreneurs.
So I am talking with venture funds that focus on women entrepreneurs, that focus on people of color. I am working with... one of the biggest entrepreneurship, not-for-profit organizations supporting LGBTQ plus entrepreneurs. I want, in Wiseheart, to be able to dedicate my time to the people who don't always have access to someone like me.
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Chapter 4: Why does Waverly emphasize supporting women and minority entrepreneurs?
I'm giving the same kind of coaching to the entrepreneurs that I work with as an independent that I always did to you and your colleagues at Boots.
Absolutely. I remember your tagline, tough love for entrepreneurs. I also recall that a few years back, you published an article about LGBTQ entrepreneurs in the Chicago Booth Review. I read the article myself, and it highlighted how underrepresented this group is in the entrepreneurial community. From what I remember, you discussed challenges like funding and general support.
It wouldn't surprise me if you planned to focus more on supporting them going forward.
Yes. In fact, I just accepted a speaking engagement to talk a little bit about funding. LGBTQ entrepreneurs in today's world with the Association for Enterprise Opportunity. They're doing an event for Pride Month. I am hoping to work with StartOut to refresh the report that we did in 2016 on the state of LGBTQ entrepreneurship in the US because I think that data is now almost 10 years old.
And one of the biggest challenges in thinking about the availability of resources to LGBTQ entrepreneurs is that nobody collects the data. That's something where you have to self-identify. You don't find it in the census.
You can't use AI to screen for names that indicate being a member of the LGBTQ community the way you do for gender research or even BIPOC research where you can triangulate and create a data set that is likely to be made up of people with non-Caucasian heritage. You can't do that. This is a community that has to self-identify.
So you can't say to venture capitalists, how many LGBTQ entrepreneurs do you have in among your portfolio companies? Because they say, how would we know? Unless that entrepreneur has had a direct conversation with them, unless they have self-identified with their investor. It's very difficult to get data.
There's a wonderful group out of Chicago called Blend that is working on diversity in the venture capital community in Chicago. And when they were doing their research, I said, why aren't you asking about LGBTQ entrepreneurs? They said, isn't that intrusive? So we think it's not intrusive to ask about gender.
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Chapter 5: What are the challenges faced by LGBTQ entrepreneurs according to Waverly?
We think it's not intrusive to ask someone about their marital status or if they have kids, but we think it's intrusive to ask if they identify as LGBTQ. Why? Because there's still a risk in identifying that way. So I said, rather than asking, are you an LGBTQ plus founder? You can ask, Do you choose to publicly identify as an LGBTQ plus founder, right?
You can ask your venture capitalists, how many self-identified LGBTQ capital entrepreneurs have you funded in your portfolio? We have to rely on self-identification to even collect data in that space. that makes it much harder to know what's happening with their access to resources, with their support, with their outcomes.
It's just a very difficult community to support for that reason, because in the US and in many cultures around the world, it's still a risk to come out as LGBTQ. We've seen a huge rise of anti-LGBTQ backlash in this country. Cargit, which has annually done a beautiful collection of products for Pride, gave in to the protests about recognizing Pride Month and pulled that line of products.
So there are ramifications in this country to being LGBTQ and in many places around the world. So it's a difficult group of entrepreneurs to support. So you're right. In Pride Month, we should acknowledge that's an area of my personal passion and interest. And I hope that WiseHeart can make a tiny difference with some of the individuals in that community.
Yeah, who knows what the future holds, especially with the election coming up. You mentioned the ongoing issues with LGBTQ identities being illegal in many places. It's a complex landscape. I also want to touch on ageism and other critical but often overlooked diversity issues. You are a baby boomer with extensive experience across various technological and economic cycles.
Speaking of age, many of our listeners, whether Gen X like myself or baby boomers like you might have retired or been laid off for various reasons. Yet, despite their valuable experience, they face entrenched ageism in the workplace and in entrepreneurship. As we discuss how to balance the heart and the head, love and logic, when making career decisions involving
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Chapter 6: How does Waverly plan to tackle data collection challenges for LGBTQ entrepreneurs?
Moving from corporate roles to entrepreneurship, to taking risks. The challenges can be very daunting for more mature individuals. So my question for you is, if an entrepreneur from Gen X or the baby boomer generation approaches you, wanting to do something meaningful to create a legacy.
They have ideas that could solve problems in industry they've known for decades, but they may not be as tech savvy as a lot of people perceive them that way. Or the pitch is not modern or sexy. How would you advise them? How would you help them balance the passion for the project with the logical aspects of launching a new venture at late age?
That's a great question, and you're 100% right. I'm seeing that in the market right now. Right now in this country, we're going through a very strange time when the markets are at an all-time high. The public markets are at an all-time high, and yet the tech companies are announcing layoffs constantly and everything. Valuations for privately held tech companies have fallen off tremendously.
It's a very strange economy and you're 100% right that economic situations make a huge difference in the landscape for entrepreneurs of all kinds. And I think I can't answer this question without acknowledging the incredible privilege that I've had in my life. People hear about the struggles I've gone through and the hard work I've put in, and I honor that. But I was born white,
to a middle class household where I got excellent education and excellent opportunities. And I've been very fortunate to have the kind of career, 22 years at a university where I've been able to accumulate a retirement nest egg. I am still able to get health insurance through the university. albeit I have to pay for it. I am incredibly fortunate and my privilege has been part of my journey.
And I think it's really important to acknowledge that a lot of entrepreneurs come from very different places and they don't have that. And so when I look at
folks of my generation who do not have nest eggs for the future who are being subject to layoffs why because when you're when you are senior in your career you're more expensive so if i lay off someone who is making two hundred thousand dollars as a director in marketing i could take that two hundred thousand dollars and hire three young people out of college um
Age is a factor in these decisions. Seniority is a factor in these decisions. And now you have these incredibly talented, experienced people in their 50s, in their 60s who want to keep working, who have a lot to add, but who are also now pretty expensive people for a full-time job. And they're saying, what do I do? What do I do with all of this experience? What do I do with all of this energy?
I don't want to take a job. that is a $75,000 a year job because I'm forced to it. I want to do something different and people have different levels of choice at different times. So one of the things that I'm noticing in that community and one of the things that I'm talking with that community about is you have been exited from these companies
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