Chief Change Officer Podcast

Episode #427: Waverly Deutsch—Love and Logic: Building Businesses That Actually Work—Part Three

Host: Vince Chan
Guest: Waverly Deutsch
Aired: July 9, 2025

Episode Overview

This finale of the “Love and Logic” series shifts focus onto Waverly Deutsch herself—her latest venture Wise Heart, the driving philosophy behind it, and Waverly’s candid perspectives on inclusion, ageism, and impactful entrepreneurship. The conversation blends deeply personal reflections with pragmatic advice, aimed at anyone aspiring to outgrow themselves through meaningful work. The wide-ranging discussion addresses supporting non-traditional founders, reimagining post-retirement careers, and why the blend of wisdom and love is at the heart (“Wise Heart”) of building businesses that actually work.

Key Discussion Points & Insights

1. The Motivation and Mission of Wise Heart

[04:48 - 10:50]

• Not a Typical Scalable Venture:
  Waverly clarifies Wise Heart isn’t about VC-style growth or an exit—“Wise Heart was started not because I wanted to build a scalable company and sell it for a hundred million dollars. Wise Heart was started because I was retiring.”
• Defining Retirement:
  She views retirement as a chance to “figure out the balance ... between remunerated work, volunteer work, and recreation.”
• The Passion for Coaching:
  Although now earning “a tiny fraction” compared to her years at Booth, Waverly emphasizes, “I'm having more fun than I've ever had.”
• Selective About Clients:
  She seeks entrepreneurs with great business potential. “I might have a session with you and turn you down as a client because ... I don't believe in it.”
• Early-Stage Focus:
  Wise Heart is for early-stage companies and investors, not large corporations or late-stage startups.
• Expanding Access:
  Waverly wants to serve founders “for whom the rest of the ecosystem is less accessible,” specifically women, minorities, people from rural or less affluent backgrounds, and LGBTQ+ individuals.
• Tagline:
  “Tough love for entrepreneurs”—Waverly provides honest coaching, not sugar-coated encouragement.

2. Addressing Gender and Diversity Inequities

[10:50 - 15:29]

• Women in VC:
  Waverly calls out persistent gender gaps—“All-male founding teams get 80 to 85% of venture capital dollars.” While all-women teams land only 2%, even mixed-gender teams see relatively little.
• Agency to Choose Clients:
  She now has the “ability to say no to customers,” unlike previously.
• Engagement with Diversity-Oriented Funds:
  Actively working with “funds that focus on women entrepreneurs, people of color ... and StartOut, one of the biggest not-for-profit organizations supporting LGBTQ+ entrepreneurs.”
• Part Remunerative, Part Giving Back:
  Wise Heart functions as both business and purpose-driven platform: “part remunerative and part giving back. That’s the goal.”

3. Supporting LGBTQ+ Founders—Barriers and Advocacy

[11:53 - 15:29]

• Lack of Data Collection:
  “One of the biggest challenges ... is that nobody collects the data.”
  Names and AI can’t reliably indicate LGBTQ+ identity, leading to underrepresentation and lack of targeted support.
• The Need for Self-identification:
  Proposes reframing questions to, “do you choose to publicly identify as an LGBTQ+ founder?” rather than intrusive inquiries.
• Societal Risks:
  Emphasizes ongoing risk and stigma: “there’s still a risk in identifying that way.”
• Recent Events:
  Points to recent backlash such as Target pulling Pride products as symbolic of these ongoing challenges.
• Hope for Wise Heart:
  “I hope that Wise Heart can make a tiny difference with some of the individuals in that community.”

4. Addressing Ageism and Career Reinvention for Senior Talent

[15:29 - 25:58]

• Entrenched Ageism:
  Many Gen X and Boomer professionals face layoffs and struggle to find new roles despite deep expertise.
• Economic Context:
  The “strange economy” sees high public markets, tech layoffs, but lagging valuations for private tech firms.
• The Privilege Factor:
  Waverly acknowledges her own advantages—race, class, education, institutional support—as instrumental, in contrast with others lacking such privileges.
• Advice for Senior Entrepreneurs:
  • Companies value senior wisdom but often rehire laid-off leaders as consultants rather than full-time employees.
  • Senior professionals may need to “go back to some of the work that got you to where you are” to prove value to young companies.
  • “You may have to let go of” legacy compensation expectations and embrace new, possibly less-defined, consulting and project-based work.

Notable Quotes:

"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."
— Waverly Deutsch [20:42]

5. Adapting to the Evolving Work Landscape

[23:05 - 25:58]

• The Future of Work:
  Vince and Waverly agree that emerging roles—enabled by AI and new tech—will require “people skills and relationship building” even in the most technical companies.
• Upskilling is Key:
  “I can't tell you how many people I know who are signing up on Coursera for a prompt engineering class ... Engage with the newer technologies ... You have to be able to communicate in the language of today’s companies if you want to build a new career.”
  — Waverly Deutsch [25:00]

6. On the Name “Wise Heart”

[26:58 - 28:23]

• The Origin Story:
  Initially wanted to use “Sapientia” (Latin for wisdom), but the agency discouraged it as too obscure.
• Blending Wisdom and Love:
  “You talk about tough love ... what you’re bringing is also the love. That’s where the combination Wise Heart came in.”
• Practicality Behind Spelling:
  “If you spell it with an I, you can’t get the URL. I wanted the URL.”
  — Waverly Deutsch [27:16]

Notable Quotes & Memorable Moments

• On Selective Client Work

  “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.”
  — Waverly Deutsch [07:48]

• On Inclusive Coaching

  “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.”
  — Waverly Deutsch [09:44]

• On LGBTQ+ Founder Representation

  “This is a community that has to self-identify. ... There are ramifications in this country to being LGBTQ and in many places around the world.”
  — Waverly Deutsch [13:21]

• On Ageism Solutions

  “You may have to actually go back to some of the work that got you to where you are ... to establish your value as someone that now charges consulting rates instead of full time salary rates.”
  — Waverly Deutsch [19:36]

• On Tech Adoption for Senior Talent

  “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 ... You have to be able to communicate in the language of today’s companies if you want to build a new career.”
  — Waverly Deutsch [25:12]

Timestamps of Key Segments

• [00:13] Introduction and context by Vince Chan
• [04:48] Wise Heart: Mission, model, target customers, and values
• [11:12] Waverly’s advocacy for LGBTQ+ and underrepresented founders
• [15:29] Ageism in entrepreneurship and workforce challenges for older professionals
• [23:05] The emerging landscape of work, upskilling, and the blend of human/AI capability
• [26:58] The story behind the Wise Heart name

Conclusion

This episode is a candid, insightful portrait of Waverly Deutsch’s journey—beyond academia and traditional entrepreneurship—rooted in a deep commitment to enabling underrepresented founders and senior professionals. With a blend of realism (“tough love”), optimism, and advocacy, Waverly and Vince Chan together sketch a future in which love, logic, wisdom, and constant reinvention are the real engines of sustainable success.

Listen for: raw advice, practical inspiration, and an honest conversation about making impact—at any age, in any climate, and always with a wise heart.

For full benefit, explore Parts One and Two of this “Love and Logic” series with Waverly Deutsch.