Chief Change Officer - #225 Love, Logic, and a Reality Check: Waverly Deutsch on Changing for the Better – Part Three

Episode Date: March 12, 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 Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.

Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Our show is a modernist community for change progressives in organizational and human transformation from around the world. If you've been following closely our special three-part love and 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 Wise Heart. 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?

Should we 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 2, we explored a significant chapter of her career, 22 years at Chicago Blue. 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 the 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. I'm working with anywhere from half a dozen to a dozen entrepreneurs actively in 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. 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? 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.

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. What, 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. 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 skill set. 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 gender teams get another anywhere from, depending on the year, 13 to 18% of venture capital dollars. But that still means that 80 to 85 percent 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, 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 businesses that require outside funding. I would likewise heart 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 DardOut, 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. If I teach again, it will likely be at a community college where those people are unlikely to ever experience a professor like me. I want Wiseheart to be part.

Renumerative and part giving back. And that's the goal of Wiseheart. And by the way, my tagline is tough love for entrepreneurs. So I'm not pulling my punches here. I'm given 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 Booth. Absolutely. I remember you tag-lined, 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 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 U.S. 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. Right? That's something where you have to self-identify. You don't find it in the census. You don't, 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 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. 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 for Pride, gave into 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, that 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, is a complex landscape.

I also want to touch on ageism and other critical, but often overlooked, diversity issues. You're 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 head, love and logic. When making career decisions involving 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, is 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 their project with the logical aspects

of launching a new venture at lay 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 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 incredible. 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 are senior in your career, you're more expensive. So if I lay off someone who is making $200,000

as a director in marketing, I can take that $200,000 and hire three young people out of college. 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 because they need to reduce costs because you're expensive and yet they still see the value of your wisdom and experience. Many of these people are being hired by companies like the companies they came from as consultants. There is generational knowledge capture that is lost when people are laid off without thought to transition plans. And I think a lot of companies have made that mistake. So I see a friend of mine who is a financial expert laid off from her CFO job now consulting as

an interim CFO for various companies in the industry that she came out of. Same thing with sales executives being brought in. What I would say to those people is you may have to do work that you outgrew in your career. You may as a CFO have to go back to work you did as an accountant or a controller to establish your value to a young company that's growing that needs financial knowledge. You may not be able to be a strategic CFO. You may have to actually go back to some of the work that got you to where you are. If you want to consult in building a go-to-market or a sales organization, you might have to write marketing collateral.

You might have to get on sales calls. You might have to do the kind of work you did when you were coming up to establish your value as someone that now charges consulting rates instead of full-time salary rates. If you're able to do that, there's a lot of room out there to find consulting work, to find engagements that could lead you to your next job. But your dream of, I'm going to go from my $200,000 job to a bigger, better $250,000 job when you're in your 60s in this market, that's a difficult one. You may have to let go of that. It's not just about stricking your mindset or upgrading your skill, learning new technologies and branching out.

The market itself is transforming. I see a future where new types of jobs and careers emerge. Roles we haven't even imagined. The names or labels for these positions might not even exist today. But even a year, two or three years max. Thanks to advancement in AI and other technologies, we're going to see work processes and roles evolve in ways we can't yet imagine. I view this shifting career landscape not just as a transition, but as an ocean of growth opportunities for everyone, whether they are in 40s, 50s, or even 60s. Health is, of course, a vital consideration. As long as we're healthy, those of us with sound minds and cross-generation experience,

particularly in people skills and relationship building, will find immense value. These skills are crucial even for AI-focused tech companies like OpenAI. They're looking for individuals who can bridge the human-technology gap, making these seemingly complex, more approachable, and human-relevant. Absolutely, you mentioned re-scaling and upscaling. I can't tell you how many people I know who are signing up on Coursera for a prompt engineering class to learn how to better leverage generative AI. People are going to need to use the contemporary tools

to deliver the value that they bring as experienced professionals. Definitely engage with the newer technologies because you can't walk into a growth company populated by a bunch of 20 and 30 somethings and not understand the impact of generative AI or not understand the impact of social media marketing or not know what TikTok is. You have to be able to communicate in the language of today's companies if you want

to build a new career after your corporate career. So we are at the end of our interview, Waverly. This is the first time in my podcast that I create a three-part series on a single topic and a single guest. You are the first person. How do you find this experience yourself? I just want to say I love how this conversation ranged from career and heart and head into AI,

continuing with the heart and head metaphor because AI is all head so you got to bring the heart, to diversity issues which are very much heart and head. Diversity is not only the right thing to do but there's a lot of evidence out there that it creates better business results, that focusing on diversity actually improves your business results. So I think I love the wide ranging conversational topics that you brought up, Mintz. Today, it was a really excellent conversation. Oh, I almost forgot.

That's one important question I haven't asked you yet. I kind of guessed the reason, but I'd like you to share with us in the show. The name of your firm, Wise Heart, and thought process behind it. Could you share your little secret with us? So I'm working with a great agency on the book, and I was creating the LLC as a place

to put revenues from the book, consulting revenues, things like that. And I was working on what to name it. And I, of course, being very head-oriented was thinking of things like Cepentia, which is Latin for wisdom. And the agency was like, no, nobody knows what that means. They both know what you're doing. It makes no sense. And I'm like, okay, so I want to think about wisdom because I had, I am in the latter portions of my life and I have gained a lot of wisdom over my years and I think that's one of the

things I bring in. And they said, you know what, you talk about tough love because what you're bringing is also the love. And that's where the combination Wiseheart came in. And you commented earlier that I spell it with a Y. The reason for that is quite simple. I could get the URL. I could be wiseheart.com. If you spell it with an I, you can't get the URL. I wanted the URL. So Waverly, thank you so much. We got so much good insights from you today. So I'll definitely

would invite you back for another session. Thank you so much for your time. Then it's been my sincere pleasure. A special thanks to Waverly for sharing two hours of her valuable time for such amazing and candid conversation. That's a wrap on our three-part series on love and logic. For those who appreciate Waverly's insights and teachings, be sure to explore the other two episodes of this series if you enjoyed this finale. And don't forget, subscribe to our show, leave us top-rated reviews, check out our website, and follow me on social media. I'm Vince Chen, your ambitious human host.

Until next time, take care.