Podcast Summary: Leap Academy with Ilana Golan

Episode 121 | August 19, 2025

How Case Kenny Turned His Podcast into a Multi-Million Dollar Brand

Episode Overview

In this episode, Ilana Golan interviews Case Kenny—author, entrepreneur, mindfulness expert, and host of the widely popular “New Mindset, Who Dis?” podcast. The conversation dives deep into Case’s journey from corporate advertising executive to mindfulness advocate and multi-million dollar brand founder. Together, they explore overcoming uncertainty, building an authentic brand, the transformative power of journaling, and advice for those leaping to new careers or entrepreneurial ventures.

Key Discussion Points & Insights

1. Origins: From Linguist to Corporate Sales

• Background in Languages: Case’s fascination with languages (Latin, Chinese, Arabic) shaped his understanding of human emotion and communication.
  • “Even in high school...I was always really good at Latin. I took five years of Latin, took like AP Latin...Then I went to Notre Dame and majored in Chinese and Arabic because I was drawn to it.” (02:18)
• Transition to Corporate: Entered advertising, rising from account executive to regional VP.
• Sales as a Foundation for Entrepreneurship:
  • “Sales will really make you realize what you’re capable of. How you could literally start at zero and build something huge.” (03:38)
• Entrepreneurial Spark: The urge for autonomy and creation propelled his shift.

2. Launching the Podcast: Starting Before You’re Ready

• Seeking Clarity Through Action: The podcast began not as a business, but as self-exploration during corporate days—Case lacked full career clarity and wanted to “know himself better.”
  • “I started the podcast because I wanted to know myself better...It was a very simple, self-centered, in a good way, endeavor.” (07:02)
• The Power of Vulnerability:
  • Struggled with embarrassment and “diminishing” the podcast to others in his corporate circle (08:22)
  • “I wish I hadn’t downplayed it. I wish I had stepped fully into it.” (09:11)
• First Episode Reflections: Focused on confidence and personal challenges
  • “If I can describe my experience and then share that back simply, maybe that shows that I explain it.” (07:55)

3. Embracing Uncertainty and Humility

• Unknowing as Growth:
  • “The more that I do this thing...it’s just made me realize how much I don’t know.” (10:55)
• Certainty vs. Openness: Ilana and Case note how driven people, especially men, can struggle to admit uncertainty.
• Faith in Self:
  • “Faith in yourself that you will figure it out is the more overriding masculine quality that reveals itself when you say, ‘I don’t know, but I'm going to figure it out.’” (12:50)

4. Scaling the Brand: From Podcast to Product

• From Content to Commerce: Case waited until after 200 episodes before considering monetization.
  • “I never intended to make any money or a career from it. So I did 200 episodes before I was even like, oh, wait a minute, maybe there is a professional future here.” (14:50)
• Turning Down Short-Term Monetization: Declined brand deals; instead, developed journals inspired by audience needs.
• Guided Journals: Origin and Impact
  • Identified a gap in available journals (“these all stress me out...this is not clarity, this is pressure”) (16:15)
  • Launched a not-instantly-successful Kickstarter, but COVID downtime and posting on Instagram led to exponential growth.
  • Sold nearly 300,000 journals between 2020 and 2022 (17:50)

5. Journaling as a Mindfulness and Growth Tool

• Defining Real Journaling (vs. to-do lists or gratitude lists)
  • “Journaling is the ultimate conduit not only to self-reflect and become self-aware but...like the only way to truly become optimistic in life.” (18:45)
• The Language of Self-Talk:
  • “The words you use to describe your feelings dictate the way you experience them out in the world.” (18:55)
  • Promotes “a part of me feels anxious” over “I am anxious”

6. Building a Portfolio Career with a Central Focus

• Everything Stems from the Podcast:
  • Podcast is the “center of the universe”—all other initiatives (books, events, products, brand deals) stem from it (26:17)
  • “For me, it's just the wheel and spokes...requires you then hedging your bets a little bit on one thing and saying this is going to be the thing from which everything else will come.” (27:48)

7. Biggest Challenges and Business Flops

• E-Commerce Roadblocks:
  • Apple’s privacy changes crushed paid ad efficiency, resulting in inventory backlogs and forced pivots (28:55)
  • “When paid goes away and you're sitting on 100,000 journals warehouse, suddenly the bills add up.” (29:41)
• Learning to Pivot: Shifted to book publishing, diversifying the business model.

8. Battling External Expectations and Non-Conformity

• Resisting Conformity:
  • “We conform because we don’t want to be the odd man out...But overwhelmingly, research shows that non-conforming traits are attractive.” (34:25)
• Qualitative Differences Over Quantity:
  • “Success doesn't come from quantitative measurements, it comes from qualitative differences.” (35:24)

9. Mindset, Grit, and the Compass of Regret

• Using Regret as a Motivator:
  • “For me, regret is a powerful compass. Would I regret not doing this today? The answer is usually always yes.” (37:23)
• Trust as Default:
  • “The trust is your default group made significantly more over the course of their career...Make trust your default.” (39:33)
• Handling Online Criticism:
  • Responds with empathy or simply pauses; criticism often isn’t personal (41:31)
  • “It is interesting...why people lash out. Usually has nothing to do with me.” (43:04)

10. Accessible Mindfulness

• Many routes to mindfulness—starts with language and self-talk for the skeptical.
  • “The mindfulness that I gravitate towards is all about your emotional vocabulary...if you’re a little averse...maybe start with me. Come on over here. The water is warm. Let's start with words.” (43:35)
• Mindful self-talk as foundational to optimism and resilience.

11. Advice for Leaping to New Careers

• No Right Way, Only a Wrong Way:
  • “There’s no right way to live your life, but there’s a wrong way. And the wrong way is to think that there’s a right way.” (48:14)
  • Encourages experimentation, personal paths, and resisting pigeonholes.

Notable Quotes & Memorable Moments

• On Vulnerability:
  • “I wish I hadn’t downplayed it. I wish I had stepped fully into it.” —Case Kenny (09:11)
• On Journaling:
  • “Journaling is the ultimate conduit...to self-reflect and become self-aware but it's frankly like the only way to truly become optimistic in life.” —Case Kenny (18:55)
• On Nonconformity:
  • “Non-conforming traits are attractive. Moving differently, being the thing that helps you break through.” —Case Kenny (35:00)
• On Regret as a Compass:
  • “Would I regret not doing this today?...It’s a compass.” —Case Kenny (37:23)
• On Figuring It Out:
  • “Faith in yourself that you will figure it out is the more overriding masculine quality that reveals itself when you say, I don’t know, but I'm going to figure it out.” —Case Kenny (12:50)
• On No Right Way:
  • “There’s no right way to live your life, but there’s a wrong way. And the wrong way is to think that there’s a right way.” —Case Kenny (48:14)

Important Timestamps

• 02:18 — Case’s early fascination with language and first career steps
• 07:02 — Why Case started his podcast (self-knowledge, not money)
• 09:11 — Reflecting on playing small and learning to own vulnerability
• 14:50 — Decision not to monetize early; the slow path to entrepreneurship
• 17:50 — Journal business explodes during COVID; transition from side project to central business
• 18:45 — Journaling and the science of self-talk
• 26:17 — Podcast as the hub of a portfolio career
• 28:55 — Business challenges (Apple privacy change, scaling pains)
• 34:25 — Battle with external expectations, family, and societal norms
• 35:24 — Success through qualitative, not quantitative, differences
• 37:23 — Using regret as a decision-making tool
• 39:33 — Career benefits of making trust your default
• 41:31 — Handling critics by developing “pause” instead of “thick skin”
• 43:35 — Invitation to explore practical, language-based mindfulness
• 48:14 — Case’s “no right way, only a wrong way” life and career advice

Final Takeaways & Tone

• Authenticity and Self-Exploration: Case’s journey reinforces that real success and fulfillment come from being honest about what you don’t know, accepting vulnerability, and taking small, consistent steps.
• Portfolio Approach: Nothing works in isolation—the podcast (or your chosen core skill) becomes a springboard for all other endeavors.
• Mindfulness Through Words: Mindfulness isn’t only meditation or “woo-woo”—it’s in the language you use with yourself daily.
• Action Over Certainty: Move forward even without full clarity—reflection, regret as feedback, and trust can guide the way.
• Radical Possibility: In today’s world, there is no linear, “right” path to success.

For listeners considering a leap, this episode is a rich blend of practical strategy, mindset shifts, and genuine encouragement that new, nontraditional paths can be not only viable but deeply rewarding.

Links:

• [Case Kenny Podcast: New Mindset, Who Dis?]
• [Leap Academy with Ilana Golan]
• [Case’s latest book: The Opposite of Settling]

Connect:

• Case Kenny: Instagram, Website
• Leap Academy: Website, Free Training (see show notes)

(Summary faithfully captures speaker tone—direct, vulnerable, often humorous, practical, and encouraging.)