Brotherhood, Business & Being a Man | The Sidney Gordon Podcast

Today Sidney Gordon sits down with Cory and Ray to talk about what it really means to be a man in today's world. From jiu-jitsu mats to boardrooms, from childhood trauma to financial freedom — nothing is off the table. This episode is for the men who are tired of surface-level advice and are ready to level up in business, family, and life.

 

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TIMESTAMPS:

00:00 – Introduction: How Corey, Ray, and Sid met
00:48 – The gun store encounter that sparked a friendship
02:00 – Behind the scenes of the Core Medical event
03:00 – Brotherhood forged through jiu-jitsu and suffering
05:00 – Why fighting builds connection, not conflict
07:00 – Real talk on fatherhood, showing up for your kids & being present
10:30 – Losing parents, grief, and emotional transformation
13:00 – Childhood stories: growing up in Brooklyn & the Philippines
17:00 – Early business failures, betrayal, and bouncing back
21:00 – Building a family-focused business and redefining masculinity
26:00 – What most people misunderstand about wealth & private equity
30:00 – Getting into Facebook, Uber, and SpaceX pre-IPO
32:00 – How AI is changing healthcare, real estate & everything
35:00 – The power of gratitude and surrounding yourself with the right people
42:00 – Why most advisors and entrepreneurs fail
45:00 – Gen Z, entitlement, and hiring based on grit — not degrees
48:00 – Why Sidney refuses to stop — even after “success”
50:00 – Powerful war stories from veterans and operators
52:30 – Closing thoughts: suffering, humility, and winning the inner war