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.20 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 1% Podcast.Top 5 US Business.Top 1 US Careers.>>>180,000+ are outgrowing. Act Today.<<<See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Full Episode
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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