Chief Change Officer Podcast Episode #337 Summary: Waverly Deutsch on Coaching Founders Most Systems Miss

Release Date: May 2, 2025
Host: Vince Chan
Guest: Waverly Deutsch

Introduction

In episode #337 of the Chief Change Officer podcast, host Vince Chan engages in a profound conversation with Waverly Deutsch, a seasoned educator and entrepreneur with over two decades of experience at Chicago Booth. This episode, the finale of a three-part series titled "Love and Logic," delves into Waverly's transition from academia to entrepreneurship, her latest venture Wise Heart, and her unwavering commitment to supporting underrepresented entrepreneurs.

Waverly's Background and the Birth of Wise Heart

Waverly Deutsch brings a wealth of experience from her 22-year tenure at Chicago Booth, where she specialized in building new ventures and coaching a diverse group of logical, innovative talents. As she embraced retirement, Waverly sought a new purpose beyond the traditional confines of a corporate career. This led to the creation of Wise Heart, an initiative designed to provide "tough love for entrepreneurs."

Waverly Deutsch [05:49]: "Wise Heart 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... but the work you do because you want to do it."

Wise Heart serves as an advisory and consultancy platform, partnering with venture capitalists like OCA Ventures and Pace Healthcare Ventures. Unlike typical businesses aiming for massive scalability and profitability, Wise Heart focuses on early-stage companies and investors, emphasizing quality over quantity and personal fulfillment over financial gain.

Target Audience: Empowering Underrepresented Entrepreneurs

Waverly's mission with Wise Heart is clear: to support entrepreneurs who "have really great business concepts and really great business capabilities" but struggle to bring their ideas to market. She places a special emphasis on women, minorities, LGBTQ individuals, and entrepreneurs from less affluent backgrounds, addressing the systemic barriers these groups face in accessing venture capital and resources.

Waverly Deutsch [05:49]: "Wise Heart is for early stage companies and investors who invest in early stage companies. ... 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."

Waverly actively collaborates with organizations like Startout, a nonprofit supporting LGBTQ entrepreneurs, to make Wise Heart’s services more accessible to those marginalized by the existing entrepreneurial ecosystem.

Diversity and Inclusion in Entrepreneurship

A significant portion of the discussion centers on the challenges faced by LGBTQ entrepreneurs. Waverly highlights the insufficient data collection on LGBTQ founders, which hinders the ability to assess and address their unique needs.

Waverly Deutsch [13:24]: "One of the biggest challenges in thinking about the availability of resources to LGBTQ entrepreneurs is that nobody collects the data... You can't say to venture capitalists, how many LGBTQ entrepreneurs do you have in among your portfolio companies?"

She advocates for self-identification as a means to gather accurate data, enabling better support and resource allocation for LGBTQ founders. Additionally, Waverly addresses the rising anti-LGBTQ backlash, underscoring the precarious environment these entrepreneurs navigate.

Waverly Deutsch [13:24]: "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."

Ageism and Entrepreneurship: Navigating Later Career Transitions

Addressing ageism, Waverly discusses the unique challenges faced by Gen X and Baby Boomer entrepreneurs. As senior professionals transition out of corporate roles, they encounter barriers such as higher salary expectations and a market that often favors younger, more tech-savvy individuals.

Waverly Deutsch [19:18]: "Many of these people are being hired by companies like the companies they came from as consultants... if you want to consult in building a go to market or a sales organization, you might have to write marketing collateral... you may have to go back to some of the work that got you to where you are."

Waverly advises seasoned entrepreneurs to leverage their extensive experience while being adaptable to perform foundational tasks that reaffirm their value in consultancy roles. She emphasizes the importance of reskilling and upskilling, particularly in contemporary tools and technologies like generative AI, to stay relevant in evolving markets.

Waverly Deutsch [26:30]: "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."

Balancing Heart and Logic in Entrepreneurship

Throughout the conversation, Waverly emphasizes the necessity of blending logic and love, especially in coaching and supporting entrepreneurs. She acknowledges the role of AI in streamlining business processes but asserts that human relationships remain paramount in building authentic connections with investors and customers.

Vince Chen [04:06]: "AI might set the stage, but it's the human touch that builds real connections with investors and employers."

Waverly reinforces this by advocating for a heart-centered approach to diversity issues, highlighting that diversity not only aligns with ethical imperatives but also drives better business outcomes.

Waverly Deutsch [27:49]: "Diversity is not only the right thing to do, but there's a lot of evidence out there that it creates better business results."

The Story Behind "Wise Heart"

Towards the end of the episode, Waverly shares the inspiration behind the name Wise Heart. Initially considering Latin terms like "sepentia" (wisdom), she chose a more relatable name that encapsulates both wisdom and compassion.

Waverly Deutsch [28:47]: "I wanted the URL... Wise Heart 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 wanted the URL."

This name reflects her commitment to delivering wisdom-infused, compassionate coaching—a blend that defines Wise Heart's unique value proposition in the entrepreneurial landscape.

Conclusion and Final Thoughts

The episode concludes with Waverly expressing her appreciation for the wide-ranging discussion, spanning career transitions, diversity, ageism, and the integration of heart and logic in entrepreneurship.

Waverly Deutsch [27:49]: "I love the wide ranging conversational topics that you brought up... It was a really excellent conversation."

Host Vince Chan wraps up the series by highlighting the invaluable insights shared by Waverly, encouraging listeners to explore the entire trilogy for a comprehensive understanding of blending love and logic in personal and professional transformation.

Key Takeaways:

• Wise Heart is dedicated to empowering early-stage entrepreneurs, particularly those from underrepresented groups.
• Diversity and inclusion are not just ethical imperatives but also catalysts for better business performance.
• Ageism poses significant challenges for seasoned professionals transitioning into entrepreneurship, necessitating adaptability and continuous learning.
• The balance of heart and logic is essential in fostering meaningful connections and achieving sustainable business success.
• Wise Heart's ethos of "tough love for entrepreneurs" encapsulates the blend of wisdom and compassion needed to navigate the complex entrepreneurial landscape.

For those interested in transformational leadership and inclusive entrepreneurship, this episode offers profound insights and actionable strategies to support and uplift the next generation of changemakers.