Leo Climaco built the kind of life that looks like winning from the outside — self-made money, proximity to billionaires, momentum in business. Then he had to sit with the fact that none of it made him feel whole. The entrepreneur and podcast host joined Sean Kelly on the Digital Social Hour to talk about what happened next.
The conversation traces his path from high school dropout to the orbit of hedge fund billionaires, through an ayahuasca journey he describes as an ego death, and into the questions that followed: why so many men feel drained, what trust really buys you, and how spirituality and success are connected.
About Leo Climaco
Leo Climaco is an entrepreneur, podcast host, and self-made millionaire whose story runs against the usual startup arc. He dropped out of high school, worked his way into rooms with hedge fund billionaires, and built real wealth — only to discover that money didn't fix what was broken inside.
That realization pushed him toward deeper work: a psychedelic journey in the jungle, an honest confrontation with his past, and a reframing of ambition from ego-driven hustle to purpose-driven leadership. Today, Climaco channels that perspective into podcasting, which he sees as a way to build trust and authority in a business world being reshaped by AI.
What Leo Climaco and Sean Kelly Talked About
- Why Climaco says the millions he made never fixed what was broken inside
- What an ayahuasca journey and ego death revealed to him about identity and purpose
- His path from high school dropout to working alongside hedge fund billionaires
- Why he believes so many men feel drained — and how they can reclaim their energy
- The mindset shift he describes from warrior to master, and from hustler to leader
- Why building trust has to come before making money in any lasting business
- How podcasting builds authority in an era being transformed by AI
- The connection he draws between spirituality and meaningful, sustainable success
Why This Conversation Matters
Plenty of podcast guests can explain how to make money. Far fewer can speak honestly about what happens when the money arrives and the emptiness stays. Leo Climaco's conversation with Sean Kelly lives in that rarer second category, and it will resonate with anyone chasing success who quietly suspects the finish line keeps moving.
▶ Watch the full episode on YouTube
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About Sean Kelly & the Digital Social Hour
Sean Kelly is an entrepreneur and the host of the Digital Social Hour, one of the fastest-growing interview podcasts in the world, where he sits down with entrepreneurs, athletes, creators, and cultural voices for candid, long-form conversations. The show draws over 100 million views a month across platforms. Explore more guest features on SeanKelly.io.
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