Ep 133: Empowering Communities and Unlocking Self-Awareness with Anne Descalzo and Rachel Zillner

Bob sits down with Anne Descalzo and Rachel Zillner, co-founders of The RADZ Group, to trace their path from banking colleagues to serial entrepreneurs building a diverse portfolio of companies. Anne and Rachel share what it felt like to step back from the CEO seat at Clutch, the company they built from scratch, and how they grew a venture fund that invests in historically underserved founders. The conversation turns to LQ: Listening Intelligence, their behavioral AI platform built on cognitive science, and how it helps people uncover blind spots and communicate more effectively at work and at home. They also discuss how AI shows up across their portfolio and why they want more founders to share their stories.

Keywords

The RADZ Group, Anne Descalzo, Rachel Zillner, Clutch, Minerva Fund, LQ Listening Intelligence, behavioral AI, cognitive listening assessment, venture capital, underserved founders, CEO transition, self-awareness, communication, coaching, Rancho Cordova, AI ecosystem, candidate fraud, cybersecurity, workforce development

Takeaways

Anne and Rachel built Clutch together before growing it into The RADZ Group, a portfolio spanning government consulting, co-working, venture capital, marketing, and technology.
Stepping back from a CEO role you built from scratch can bring genuine grief, even alongside pride and trust in new leadership.
Their Minerva venture fund intentionally invests in historically underserved founders, with most portfolio companies female founded or led by a founder of color.
LQ: Listening Intelligence draws on 15 years of cognitive science research to help people understand their own listening habits and adapt how they communicate.
Behavioral AI built on that research can prep people for difficult conversations and reframe misunderstood behaviors, like mistaking reflective listening for indecisiveness.
New AI risks are emerging too, including candidate fraud and cybersecurity threats tied to remote work.
Anne and Rachel see in-person community as essential to how their region and portfolio companies keep pace with AI.
They're on a mission to help more founders and leaders feel comfortable sharing their stories instead of staying under the radar.

Quotes

We think of projects like Play-Doh and everything has, you know, like a new shape that it can take.
I came downstairs, very dramatically draped myself across to Anne's desk and just, if I could ever leave this place, would you go with me? And I now call that my proposal.
Grief is associated a lot of times with death, but grief can also show up with transition and change.
We have 15 years of scientific research. It's the only scientifically backed cognitive listening assessment in the world.
We decided to start a venture capital fund to support other folks who don't always get the type of lending or support that they need.
Imagine what could happen in the workplace when folks show up with that understanding.

Chapters

00:02 Welcome and introductions

00:56 Meet Anne and Rachel

02:54 From banking colleagues to co-founders

04:15 The Clutch origin story

05:38 Building The RADZ Group portfolio

10:04 Stepping back as CEO and navigating grief

15:03 Introducing LQ Listening Intelligence

19:51 Behavioral AI for difficult conversations

22:34 Bringing the tool into everyday work

26:08 Uncovering hidden biases and rethinking labels

35:02 The future of listening as a standardized skill