In Part 3, Waverly Deutsch steps into her latest role: founder of Wyseheart, a coaching firm designed to help the most overlooked founders build ventures that last. Focused on meaningful business, not unicorn exits, she brings her full career of coaching, teaching, and hard-won insight to early-stage leaders across age, gender, race, and identity. For Gen Xers who aren’t ready to “retire,” this is a playbook for doing your best work—on your terms, with your values, and no need for external approval.What Retirement Really Means to Her“Retirement means you no longer have to work to cover basic necessities… but you work because you want to.”Waverly explains why Wiseheart was never about building a high-growth company, but creating space for meaningful work in the next chapter of life.Who Wiseheart Is Really For“I might have a session with you and turn you down as a client.”She describes her ideal clients: early-stage founders with strong ideas and potential—but she’s selective, because she coaches from belief, not obligation.Opening Access Where Systems Don’t“I want to make myself available to people who don’t always have access to someone like me.”Waverly shares how Wiseheart is designed to serve women, BIPOC, LGBTQ+, rural, and underestimated founders who often face systemic barriers.LGBTQ+ Advocacy Through Data and Action“You can ask: do you choose to publicly identify as an LGBTQ+ founder?”She calls out the data gap and cultural risks still facing LGBTQ+ entrepreneurs—and how her work with StartOut aims to help change that.Advising Older Entrepreneurs With Realism“You may have to go back to the work that got you there.”She offers grounded advice to Gen X and Baby Boomer entrepreneurs who face ageism and cost-cutting—and encourages them to translate wisdom into flexible, consulting-based careers._________________________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.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<
Chapter 1: Who is Waverly Deutsch and what is her background?
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?
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Chapter 2: What is Wiseheart and why was it founded?
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 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.
Chapter 3: Who are the target customers of Wiseheart?
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.
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.
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Chapter 4: How does Wiseheart support underrepresented 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.
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 of 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 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.
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Chapter 5: What challenges do LGBTQ+ entrepreneurs face and how is Waverly addressing them?
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.
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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