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From Wall Street to Creator, a $645,099 Business Pivot, Principled Marketing, and Combatting Inner Narratives with Khe Hy

From Wall Street to Creator, a $645,099 Business Pivot, Principled Marketing, and Combatting Inner Narratives with Khe Hy

This episode with Khe Hy, founder of RadReads, is a conversation that goes beyond the usual topics of content, SEO, marketing, and tech. He discussed his journey of founding RadReads, his transition from Wall Street to being a full-time creator, and his tips on productivity. 

Khe spent 15 years working on Wall Street and was one of the youngest Managing Directors at BlackRock. He’s been called Oprah for Millennials by CNN and the Wall Street Guru by Bloomberg and his work has been featured in the Wall Street Journal, TedX, Barrons, Time Magazine, and Quartz.

Khe also delved into introspection, questioning narratives, and the impact of coaching and emphasized the importance of self-reflection, personal freedom, and exploring deeper emotions. 


  • RadReads and Living an Examined Life 
  • Understanding business games 
  • The tension of breaking societal narratives 
  • The discomfort of pain-based marketing in self-improvement content 
  • Authenticity and the “Oprah for Millennials” Label
  • The power of luck and good timing 
  • The four quadrants of work 
  • Reframing tasks as dollar values 
  • The game of real human connection 
  • Questioning societal narratives
  • The Pivotal Moment and Trade-Off 
  • The psychology of freedom 
  • Uncovering inner thoughts and feelings
  • Carrying grief and its impact on actions
  • The fallacy of the grass always being greener 

Listen to the podcast:

Key Takeaways:

[00:06:47] RadReads and Living an Examined Life 

Talks about RadReads, a platform that helps people live intentional and joyful lives, discussing the topics covered and the approach taken to explore deeper questions.

[00:11:21] Understanding Business Games 

Talks about their focus on work ethic, relationships, and leadership to succeed in their career on Wall Street.

[00:18:10] The Tension of Breaking Societal Narratives 

Exploring the idea of breaking out of the societal narrative and challenging assumptions about career choices and personal fulfillment.

[00:25:48] The Discomfort of Pain-Based Marketing in Self-Improvement Content 

Discussing the challenges of selling info products in the realm of self-improvement, and the discomfort of using pain-based marketing techniques to sell courses and ebooks.

[00:33:06] Authenticity and the “Oprah for Millennials” Label 

Exploration of how the label “Oprah for Millennials” came about and the mixed feelings associated with it.

[00:36:47] The Power of Luck and Good Timing 

Luck and good timing played a significant role in the success of a photo shoot and the release of a feel-good story.

[00:42:40] The Four Quadrants of Work 

Understanding the four quadrants of work (10-dollar, 100-dollar, 1000-dollar, and 10,000-dollar work) and finding the right mix for productivity and impact.

[00:46:15] Reframing Tasks as Dollar Values 

Discussion on the importance of reframing tasks as dollar values and how it helps prioritize work effectively.

[00:54:49] The Game of Real Human Connection

Discussion about the desire for genuine human connection and the potential for events and gatherings to facilitate this.

[01:00:07] Questioning Societal Narratives 

Encouragement to challenge societal scripts and norms, giving oneself permission to explore alternative paths and beliefs.

[01:04:41] The Pivotal Moment and Trade-Off 

Discuss a pivotal moment where they could have taken VC funding for their business but chose not to, reflecting on the trade-off between financial success and personal values.

[01:13:20] The Psychology of Freedom 

Discussion on true freedom and how it is related to unshackling oneself from negative thoughts and beliefs.

[01:14:59] Uncovering Inner Thoughts and Feelings 

Explanation of how coaching practices help surface and examine underlying emotions and beliefs that affect daily actions and decisions.

[01:22:49] Carrying Grief and Its Impact on Actions 

Discussion on how carrying grief tightly can blind one to everything else and how it impacts actions.

[01:29:21] The Fallacy of the Grass Always Being Greener 

Insight into the downsides of pursuing what one thinks they want and the trade-offs involved.

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David Khim

David is co-founder and CEO of Omniscient Digital. He previously served as head of growth at and Fishtown Analytics, and before that was growth product manager at HubSpot where he worked on new user acquisition initiatives to scale the product-led go-to-market.