In this episode of Don’t Be a Jerk, host Healey Cypher sits down with Adam Greenfeld, co-founder of Frij and former co-founder of Thesis, to explore how his greatest obstacle wasn’t building companies… it was his relentless inner critic.

Known for transforming brands into thriving businesses, Adam opens up about his battle with self-doubt and perfectionism, revealing powerful insights and practical tools for founders and leaders to cultivate true self-compassion, clarity, and success.

In this honest and eye-opening conversation, you’ll discover:

• How Adam realized the inner voice pushing him to be perfect was actually holding him back—and the practical steps he took to break free from it.

• Why an “exit lifestyle” isn’t something you need to wait until your company is acquired to experience—and exactly how Adam started living his ideal life decades ahead of schedule.

• How intentional pauses can radically transform your day-to-day interactions, relationships, and overall happiness.

• Why Adam believes self-love isn’t just a nice-to-have. It’s the essential foundation of sustainable success and happiness.

• Adam’s unique daily journaling practice that helped him uncover hidden truths, reduce anxiety, and clarify his real purpose.

• How your internal state and mindset directly shape your external leadership style—and why your “vibe” matters far more than your words.

• Powerful lessons Adam learned from working closely with high-profile entrepreneurs like Adam Neumann, including how visionary leaders consistently inspire excitement rather than chase happiness.

If you’re tired of the endless hustle, internal negativity, and chasing false definitions of success, Adam’s story is your invitation to step into a kinder, more intentional way of leading and living.

Join Healey and Adam for this vulnerable yet empowering episode—and learn how silencing your inner critic can be your greatest competitive advantage, both professionally and personally.

Listen and subscribe wherever you get your podcasts!