Money Meets Mystery: Aaron and Trevor on the Art of Scaling the Right Mountain ⛰️

With money, mountains, and mystery, we explore the journeys of two visionaries redefining the quest for purpose and the art of scaling the right peaks. Aaron Holiday, venture capitalist and co-founder of 645 Ventures, and Trevor Paglen, artist and investigator of the unseen, reveal how they navigate complex landscapes to reach meaningful summits in their respective worlds of finance and art. From Aaron’s early days challenging venture capital conventions to Trevor’s pioneering artwork that unveils hidden networks, both have honed the skill of selecting the right mountains to climb in worlds where the stakes are high and the paths are rarely marked.

Venture Capital: Aaron Holiday on 645 ventures' data-driven approach to sourcing deals and bringing the invisible to life

⛰️ Imagine a mountain rising before you, the peak symbolizing your goal. You begin the climb, step by step, feeling the weight of your hopes and dreams. Near the top, you catch sight of another mountain, taller and more challenging just beyond. It makes you wonder: are you on the right mountain?

Aaron embodies this spirit of exploration. Driven by curiosity and fearless in his pursuit of new challenges, he willingly moves from peak to peak, undaunted by the journey. Ultimately, this dedication led him to establish his own highly successful venture capital fund, a peak uniquely his own.

"We pioneered outbound deal sourcing at the early stage using proprietary software... The software surfaces opportunities daily, bringing 'aces to the top of the deck.' Even if I met a company three months ago, if it starts to pop off, the software flags it, saying, 'Hey, you need to look back at that.' It goes beyond human capacity, keeping our focus on high-signal growth"​.

Art: Trevor Paglen with a bold artistic approach to challenging societal thinking and setting new precedents

Trevor is another kind of explorer. With a Ph.D. in Geography, he coined the term “Experimental Geography,” bringing a fresh lens to how we navigate landscapes—both literal and conceptual. Trevor understands the art of scaling mountains and capturing peaks, yet he values what lies beyond the frame just as much as what’s within it. For him, the unseen edges of exploration are as essential as what we encounter directly.

"When I was in art school, you know, I was always told what is in the frame is the art. And if you need something outside of the frame to inform that, then you're a bad artist. And I always thought that's ridiculous. Like, 'cause we always have stuff that's outside of the frame that's informing us.”​

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