After 12 years of working in corporate advertising, Case Kenny launched a podcast, New Mindset, Who Dis? as a personal experiment. In its first month, the show drew 57,000 downloads, yet Case kept it hidden, afraid it didn’t fit his professional image. Over time, he embraced his vulnerability, created bestselling guided journals, and built a brand helping millions live more optimistic and mindful lives. In this episode, Case joins Ilana to share how a side project turned into a multi-million-dollar portfolio career, why regret is his decision-making compass, and how choosing the right words can change the way you live.

Case Kenny is an author, entrepreneur, and host of the globally recognized podcast, New Mindset, Who Dis?. Known for his work in mindfulness and personal growth, he has built a multi-million-dollar brand through writing, guided journals, and speaking engagements.

In this episode, Ilana and Case will discuss:

(00:00) Introduction

(01:42) From Language Studies to Corporate Advertising

(05:07) Starting the Podcast Without Clarity

(07:43) Overcoming the Fear of Vulnerability

(09:04) Stepping Fully into a New Identity

(14:14) When Passion Becomes a Business

(16:53) COVID, Journals, and a Turning Point in Sales

(18:10) Why Journaling Works and How to Start

(25:01) Building a Connected Portfolio Career

(27:40) Business Challenges and Six-Figure Losses

(33:09) Battling Expectations, Regret, and Trust as a Default

(42:10) Defining Mindfulness and Advice to Case’s Younger Self

Case Kenny is an author, entrepreneur, and host of the globally recognized podcast, New Mindset, Who Dis?, a podcast with tens of millions of downloads. Known for his work in mindfulness and personal growth, he has built a multi-million-dollar brand through writing, guided journals, and speaking engagements. His work has been featured on The Today Show, Good Morning America, Forbes, and NBC.

Connect with Case:

Case’s Website: casekenny.com

Case’s LinkedIn: linkedin.com/in/casekenny/

Case’s Instagram: instagram.com/case.kenny

Case’s YouTube: youtube.com/c/CaseKenny

Resources Mentioned:

Case’s Podcast, New Mindset, Who Dis?:  pod.link/1383599078

The Opposite of Settling by Case Kenny: https://www.amazon.com/Opposite-Settling-Everything-Without-Losing/dp/1401995918

The Soul’s Code by James Hillman: https://www.amazon.com/Souls-Code-James-Hillman/dp/0517271036

That’s Bold of You by Case Kenny: https://www.amazon.com/Thats-Bold-You-Thrive-Vibrant/dp/B0BRDFLJNZ