What if the very traits that make you successful… are also the ones slowly breaking you?
In this episode of Not Another Podcast, Brennan Pothetes sits down with Alex Song, former Goldman Sachs and Pershing Square investor turned founder & CEO of Proxima, to explore the brutal, hidden side of building.
Alex has lived every founder archetype:
Finance prodigy. Serial entrepreneur. Operator of a fast-growing AI data company.
But beneath the résumé lies the same question every founder eventually faces:
How much can you build before you break?
This is a story about the anxiety that never leaves. The fear of slowing down, the ego that fuels you, and what happens when “making it” doesn’t feel like enough.
Together, Brennan and Alex unpack:
• The chaotic childhood patterns that drive high performer• Why ego can quietly sabotage your best decisions• How therapy, spirituality, and presence sharpen your leadership• Why fatherhood made Alex a more empathetic (and effective) CEO• The quiet loneliness of being “the one who’s supposed to have it together”
This episode is for founders who look successful on paper but can’t sleep at night.
If you’ve ever asked yourself what’s the point of all this? …this one’s for you.
Timestamps:
00:00 – Cold open: The pressure that never fades
03:00 – The West Coast “fake nice” vs. NYC directness
06:30 – From Goldman Sachs to entrepreneurship
09:00 – Why most holding companies fail
14:00 – The ego trap: when validation runs your business
17:00 – Redefining purpose inside the AI gold rush
25:00 – Brennan’s burnout story and what it revealed
27:00 – Alex’s chaotic childhood and how it shaped his resilience
32:00 – The pain tolerance every founder learns to hide
35:00 – Why therapy matters more than your next investor
37:00 – The “work hard, play hard” myth that destroys founders
40:00 – Spirituality, presence, and finding your center
43:00 – How vulnerability builds real trust with your team
49:00 – Hiring people who are smarter than you
54:00 – Learning to say, “I don’t know” as a CEO
58:00 – What activist investing taught Alex about conviction
1:04:00 – The mentorship trap: transactional vs. authentic help
1:08:00 – Fatherhood, empathy, and redefining success
1:15:00 – The Everest metaphor: building without breaking
1:18:00 – Closing thoughts on purpose and longevity
