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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this rare and deeply honest conversation, we sit down with Jeff Salzenstein — former top-100 tennis player turned executive performance coach — for a soulful exploration of identity, grief, resilience, and the emotional reckoning that comes when success is no longer the point.
Jeff opens up about the moment he knew it was time to leave tennis, the trauma that called him into coaching, and the recent experiences that are humbling him back into his body — and back into his heart. Together, we unpack what it means to be truly seen, the edges of emotional risk that no one talks about, and the surprising places the inner rebel shows up in midlife.
This one’s for the over-functioners, the fixers, the seekers, and the late bloomers. For anyone wondering if it’s too late to change your story — or be truly seen in the one you’re already living.
00:00 Introduction and Setting the Scene
00:42 Meet Jeff Selzen Stein
01:13 Tennis Career Highlights and Challenges
01:40 The Importance of Names and Identity
04:49 Inner Rebel and Personal Growth
07:41 The Role of Creativity in Tennis
11:25 Holistic Approach to Performance
19:31 Navigating Fear and Intuition
26:14 Transitioning from Tennis to Coaching
31:13 Helping My Brother's Transformation
31:57 From Alone to Community: A Journey of Accountability
32:52 Navigating Life Transitions and Embracing New Challenges
33:09 The Struggle with Community and the Lone Wolf Mentality
35:06 Exploring Relationships and the Desire for Family
36:57 The Importance of Self-Work and Vulnerability
43:30 Caring for My Father and Facing Personal Judgments
47:59 Reflecting on My Brother's Journey and Its Impact
53:01 The Pain of Unseen Relationships and the Path to Healing
56:14 Concluding Thoughts and Gratitude
If you loved today’s episode, please leave a review and share your favorite takeaways by screenshotting this episode and tagging us on Instagram! We also have a free virtual monthly community call on the 3rd Thursday of every month, join here!
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