The $100M Entrepreneur Podcast

Episode: Find Your TRUE Passion by Focusing on USEFULNESS First

Host: Brad Sugars
Guest: John Tanoff
Date: June 4, 2025

Episode Overview

In this episode, Brad Sugars welcomes former film executive turned career coach John Tanoff for a deep dive into redefining success, discovering passion through usefulness, and building lasting self-confidence in entrepreneurship. Together, they challenge conventional wisdom around “follow your passion,” advocate for usefulness as the foundation for fulfillment, and discuss the critical importance of inner work, self-knowledge, and service to others. The conversation is rich with stories from John’s multifaceted career and practical advice for entrepreneurs, business leaders, and anyone contemplating a career shift.

Key Discussion Points & Insights

1. Usefulness Over Passion (00:00-11:38)

• The Central Thesis:
  John challenges the traditional advice to “follow your passion,” suggesting instead that real passion emerges from being useful and making a positive difference.
• Key Quote [00:00]:
  “If you can figure out how you can be useful, helpful, of service… then your usefulness can become your passion.” — John Tanoff
• Ben Horowitz’s Commencement Address [07:42]:
  John credits venture capitalist Ben Horowitz for this reframing, emphasizing that passion alone isn’t enough — real fulfillment and career momentum come from usefulness and service.

2. Rethinking Success: Emerson’s Definition (01:09-02:18)

• Reading Emerson’s Wisdom [01:09]:
  John shares Ralph Waldo Emerson’s classic definition of success, shifting the focus away from material achievement.
• Memorable Emerson Quote [01:36]:
  “To know even one life has breathed easier because you have lived—this is to have succeeded.” — John Tanoff (quoting Emerson)
• Key Insight:
  Success is about impact, appreciation, and lasting positive effects on others, not just personal or financial gain.

3. The Journey from External to Internal Focus (03:51-07:23)

• Hollywood to Coaching [03:51]:
  John narrates his progression from film production (external wins, outward showmanship) to talent management and finally to coaching, where inner alignment and personal evolution became paramount.
• On “Casting” in Life [12:18]:
  Just as films need the right cast, teams and organizations thrive on diversity of perspectives, not uniformity.

4. Attracting Opportunities vs. Chasing Them (09:25-11:38)

• From “Chasing” to “Attracting” [09:25]:
  The futility of relentlessly chasing jobs or clients versus the power of attracting them by knowing and serving from one’s strengths.
• Key Questions for Self-Assessment [10:27]:
  • What am I naturally good at?
  • Where can I be most useful?
  • How aligned am I with my values?
• On Listening [10:39]: “The pathway to do that is to listen. We are really bad at listening… the magic in a conversation happens when you give it a moment to settle…” — John Tanoff

5. Alignment, Values, and Cultural Fit (14:20-15:08)

• The Importance of “Inner Fit”:
  John stresses that fitting company culture and sharing values counts more than matching job descriptions or chasing the biggest paycheck.
• Story of Value Misalignment [15:08]:
  John recounts helping a client from investment banking realize the personal cost of being “out of alignment” with organizational values.

6. Navigating Change and Redefining Failure (17:29-19:56)

• The Startup Roller Coaster [17:29]:
  John shares his experience of scaling up a company during the 90s tech bubble, then losing it all when the Nasdaq crashed.
• Redefining Failure [17:29]: “There is no failure. Failure is a judgment... You want to look at your life as a set of experiences and learn from that feedback.” — John Tanoff
• Career Adaptation [19:56]:
  The traditional 3-phase career model is obsolete; now, it’s about continuous learning, constant generativity, and giving back — not settling into one track for life.

7. Building Confidence Through Action (00:41, 23:47-27:09)

• “Confidence Comes Last” [00:41, 23:47]:
  John repeatedly insists that waiting for confidence means you’ll wait forever — action comes first, and confidence follows through experience.
• Memorable Quote [23:47]: “If you think that you're just waiting to feel more confident before you take this step... you're gonna be waiting forever. Just do it. Feel the fear and do it anyway.” — John Tanoff
• Courage Defined [25:48]:
  Courage is acting from the heart despite fear, cultivated through daily self-nurturing and a sense of worthiness.

8. Top Advice on Success (27:27-28:54)

• Favorite Advice [27:27]: “God fires you from jobs you're too dumb to quit.” — John Tanoff (quoting a teacher)
• Why It Resonates [27:48]: This advice removes the stigma from professional setbacks, reframing them as gentle nudges (or shoves) from the universe to move forward and evolve.
• On Stagnation:
  John urges ongoing self-questioning: Am I aligned? Am I useful? Am I serving others? If not, change is needed, because otherwise, the universe will intervene.

Notable Quotes & Memorable Moments

• [00:00] “If you can figure out how you can be useful, helpful, of service... then your usefulness can become your passion.” — John Tanoff
• [01:36] “To know even one life has breathed easier because you have lived—this is to have succeeded.” — Ralph Waldo Emerson (read by John Tanoff)
• [07:42] “If you subscribe to the Joseph Campbell notion of follow your bliss and the money will follow, Ben Horowitz's idea is … focus on your usefulness.” — John Tanoff
• [17:29] “There is no failure. Failure is a judgment… You want to look at your life as a set of experiences and learn from that feedback.” — John Tanoff
• [23:47] “If you think that you're just waiting to feel more confident before you take this step... you're gonna be waiting forever. Just do it. Feel the fear and do it anyway.” — John Tanoff
• [27:27] “God fires you from jobs you're too dumb to quit.” — John Tanoff

Suggested Listening Timestamps

• Defining Success, Emerson’s Quote — [01:09-02:18]
• From Passion to Usefulness — [07:42-08:41]
• Attracting vs. Chasing Opportunity — [09:25-11:38]
• Inner Fit and Team Casting Philosophy — [12:18-14:20]
• Redefining Failure and Career Change — [17:29-19:56]
• Building Confidence Through Action — [23:47-27:09]
• Best Advice on Success — [27:27-28:54]

Final Takeaways

• Start Inside: Success and fulfillment start with self-knowledge, values, and alignment, not external validation.
• Be Useful: Prioritize being of service and adding value — passion and opportunity flow from usefulness.
• Act, Then Confidence Comes: Waiting for confidence before taking action guarantees inaction; “feel the fear and do it anyway.”
• Redefine Failure: View setbacks as experiences for growth, not indictments of your worth or potential.
• Constantly Reevaluate: Repeatedly assess if you’re living your values and being useful — or risk being “fired by the universe” into needed change.

If you’re navigating your own career shift, building a business, or hungry for a more meaningful path, this episode is packed with insight, candor, and actionable wisdom rooted in real-life reinvention.