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.
