I remember the exact moment I realized I was becoming part of the problem.
Standing in a San Francisco hotel ballroom, I caught my reflection in a mirrored wall. Navy quarter-zip sweater. Slim-fit chinos. Allbirds. AirPods. The unofficial uniform was complete. But it wasn't just the clothing that had become standardized. It was the language, the thought patterns, the frameworks, the references.
Okay, fine I was never in that deep. And this was in NYC. But something had changed.
When had I started saying "first principles" in every other sentence? When had I begun prefacing observations with "the reality is" as if I alone possessed some objective truth?
Somewhere along the way, too many investors stop having a job in venture capital and become a "VC." And there's a world of difference between those identities.
The Professionalization of Sameness
Venture capital wasn't supposed to become a personality cult.
It began as a financial discipline with a specific purpose: deploying capital to high-risk, potentially transformative technology companies that traditional financing couldn't properly value or support. The industry attracted iconoclasts and independent thinkers precisely because conventional finance couldn't accommodate truly novel ideas.
But what happens when the unconventional becomes conventional? When the outsiders become insiders? When disruption calcifies into dogma?
You get what we have now: venture capital as identity rather than profession. A community that doesn't just think alike but dresses alike, talks alike, lives alike. A group so busy reinforcing its belonging that it has forgotten its purpose.
The Patagonia vest isn't just a garment. It's a totem. The formulaic LinkedIn posts aren't just content. They're rituals. The buzzwords aren't just terminology. They're shibboleths that separate insiders from outsiders.
None of this would matter if it were merely aesthetic. But conformity in appearance reflects something more insidious: conformity in thought. And when an entire industry tasked with identifying the non-obvious begins to think in obvious ways, we have a fundamental problem.
The Cost of Belonging
My own journey into the center of VC culture wasn't immediate. I entered as an outsider, having started my career washing rental cars at Enterprise before clawing my way through community college night classes. When I finally broke into finance and eventually venture, I carried that outsider perspective with me.
Until gradually, I didn't.
The gravitational pull toward sameness is subtle but relentless. It begins with small adjustments. You learn to frame your thoughts using industry jargon. You discover which references earn nods of approval. You internalize the unwritten rules of which founders deserve attention and which don't.
These micro-adaptations feel innocent enough in isolation. But collectively, they represent something profound: the surrender of original thought for the comfort of belonging.
I remember sitting in a partner meeting where we were evaluating a founder building tools for manufacturing workers. The technology was impressive, the market enormous, the early traction promising. But the room's energy shifted when someone mentioned that the founder hadn't gone to college, had never worked at a tech company, and spoke with a thick regional accent.
No one explicitly rejected the investment because of these factors. The language was more coded than that. "I'm not sure they can scale the team." "The go-to-market feels uncertain." "Do they have the network to recruit senior talent?"
These concerns might have been valid in isolation. But collectively, they revealed an uncomfortable truth: we were more comfortable backing people who reminded us of ourselves or fit our mental model of what a successful founder should be.
I said nothing. And in that silence, I became complicit.
The Danger of Intellectual Monoculture
There is something profoundly risky about an industry whose purpose is finding the unexpected, yet whose composition virtually guarantees it will miss the truly novel.
When everyone in venture comes from the same five universities, has worked at the same ten companies, lives in the same three neighborhoods, and socializes in the same exclusive circles, the industry develops intellectual blind spots so vast they become invisible to insiders.
This isn't just about diversity in the demographic sense, though that remains a critical issue. It's about diversity of perspective, experience, and worldview. It's about who has access to decision-makers. It's about whose problems are seen as worthy of solving.
The startup ecosystem celebrates "first-principles thinking," yet operates within such narrow boundaries of acceptable thought that true originality is often filtered out before it ever reaches a partner meeting.
I've watched promising companies struggle for capital not because their ideas lacked merit but because their founders couldn't perform the specific cultural rituals the industry has come to expect. The pitch cadence. The growth narrative. The casual display of insider connections.
Meanwhile, enormous sums flow effortlessly to founders who have mastered these performances, regardless of their ideas' substance. The ability to pattern-match to previous successes has replaced the capacity to recognize genuine innovation.
And we wonder why so many venture-backed companies feel derivative.
When Fitting In Replaces Thinking
Perhaps the most corrosive effect of VC's transformation into an identity cult is what it does to emerging talent in the industry.
Young investors learn early that advancement depends more on fitting in than developing genuine insight. They study the social dynamics of the industry with far more intensity than they study markets, technologies, or human needs.
I've mentored associates who can perfectly mimic the opinions of prominent VCs on Twitter but struggle to form independent judgments about investment opportunities. They've learned to perform venture capital rather than practice it.
This creates a devastating feedback loop. Each generation of investors becomes more disconnected from original thought, more concerned with social positioning, more vulnerable to groupthink.
The result is predictable: waves of capital flowing to identical companies, valuations detached from fundamentals, and entire sectors collapsing when the music stops.
We saw this with Web3. With delivery apps. With direct-to-consumer. With every boom-and-bust cycle where momentary consensus was mistaken for insight.
The pattern repeats because the industry lacks the intellectual diversity to question its own assumptions. When everyone at the table shares the same biases, those biases become invisible. When everyone reads the same newsletters, attends the same conferences, and follows the same Twitter accounts, contrarian thought becomes impossible.
The False Comfort of Pattern Recognition
The venture industry celebrates pattern recognition as its highest virtue. The ability to see similarities between the present and past successes is considered the mark of a great investor.
But this emphasis on pattern matching has a dark side. It privileges the familiar over the truly novel. It ensures that founders who resemble previous success stories receive capital, while those who don't struggle for attention regardless of their ideas' merit.
Pattern recognition becomes especially problematic when the patterns themselves reflect historical inequities. When we pattern-match based on where someone went to school, which companies they worked for, or how they present themselves, we're often just reinforcing existing privilege rather than identifying genuine potential.
I've sat in too many meetings where a founder was praised for being "one of us" or having the right "pedigree." These statements weren't meant maliciously. They reflected a genuine belief that these attributes predicted success.
But they also revealed how thoroughly the industry had confused correlation with causation. Did these founders succeed because of their elite backgrounds? Or did their backgrounds simply give them access to capital that allowed their ideas to be tested in the market?
The venture model is supposed to identify non-consensus, right ideas before they become obvious. But how can we identify the non-obvious when our perspective is so thoroughly shaped by obvious markers of status and belonging?
Reclaiming the Discipline
My own path back to intellectual independence began with uncomfortable self-awareness. I had to recognize how thoroughly I had internalized the cultural norms of venture, how easily I had surrendered original thought for the comfort of belonging.
This realization wasn't immediate. It accumulated through moments of cognitive dissonance. The promising company we passed on that went on to extraordinary success. The perfect-on-paper investment that failed despite checking every box. The founder from an unexpected background who outperformed everyone's expectations.
These experiences created cracks in the edifice of pattern matching. They suggested something unsettling: that many of our industry's most cherished assumptions might be wrong.
Real progress required more than just noticing these contradictions. It demanded active resistance to the pull of conformity. It meant developing mental models based on observation rather than imitation. It meant risking social capital by challenging consensus views.
At Daring Ventures, we've tried to institutionalize this resistance to groupthink. We deliberately hire investors with non-traditional backgrounds. We question our assumptions in post-mortems of both successes and failures. We track our decisions to identify unconscious patterns in our judgment.
This isn't about performative contrarianism. It's about recognizing that genuine insight comes from authentic thinking, not from consensus.
Beyond the Pedigree
The startups that create extraordinary value aren't always built by people who check the conventional boxes. They often come from founders intimately familiar with problems that elite networks haven't experienced or noticed.
The founder who struggled with financial exclusion before building a fintech company that serves the underbanked.
The founder who experienced medical bureaucracy firsthand before creating a healthcare platform that simplifies access.
The founder who worked in logistics for years before developing software that addresses inefficiencies invisible to outsiders.
These builders bring perspective that can't be acquired through privileged observation. They understand problems at a visceral level that academic study can never replicate.
Yet the venture industry systematically overlooks these founders because they don't match the pattern of past successes. They don't have the right degrees, the right previous employers, the right connections, or even the right vocabulary.
This isn't just inequitable. It's bad business. It means the industry routinely misses opportunities to back transformative companies because they come in unfamiliar packaging.
The Path Forward
Reclaiming venture capital as a discipline rather than an identity requires conscious effort. It means:
Recognizing when we're making decisions based on comfort rather than conviction.
Actively seeking perspectives that challenge our assumptions.
Evaluating founders on their insight and execution rather than their similarity to previous success stories.
Building investment teams with genuine diversity of thought, background, and experience.
Creating feedback mechanisms that help us identify our blind spots.
This isn't just about addressing historical inequities, though that remains important. It's about making better investment decisions. It's about rebuilding venture capital around its original purpose: financing innovation that traditional systems miss.
The firms that thrive in the coming decade won't be those that perfect the art of pattern matching to prior successes. They'll be those that develop the capacity to recognize potential where others don't see it.
They'll back founders who don't look like yesterday's successes but are uniquely positioned to create tomorrow's.
They'll recognize that the qualities that make someone an outsider to Silicon Valley culture aren't weaknesses to be overcome. They're potential strengths that bring fresh perspective to stale problems.
The Personal Practice
My own journey away from the venture capital personality cult hasn't been linear. There are still days when I catch myself slipping into industry clichés or making judgments based on superficial patterns rather than substance.
Authentic thinking isn't something you achieve once and possess forever. It's a practice that requires consistent renewal, especially in an environment designed to reward conformity.
For me, this practice includes regular exposure to contexts where venture capital status markers have no currency. Conversations with people building outside the startup ecosystem. Time in communities where different forms of knowledge and experience are valued.
These experiences help recalibrate my sense of what matters, what's real, and what constitutes genuine insight versus performative wisdom.
I've also learned to notice the physical sensations that accompany independent thought. The discomfort of holding a view at odds with industry consensus. The vulnerability of admitting uncertainty when everyone else projects confidence. The anxiety of backing a founder whom peer firms have overlooked or rejected.
These feelings aren't weaknesses to be suppressed. They're signals that I'm engaging with genuine uncertainty rather than retreating to the false comfort of consensus.
The Venture We Need
The purpose of venture capital was never to create a class of investors with identical perspectives, backgrounds, and thinking patterns. It was to finance the truly novel, to take calculated risks on ideas with transformative potential.
That mission has been compromised by the industry's transformation into a social identity. But it isn't lost.
A new generation of investors is emerging that recognizes the limitations of pattern matching, the dangers of conformity, and the opportunity in genuine independent thought.
They understand that great investments often look wrong before they look right. That truly innovative ideas initially appear risky precisely because they challenge existing mental models. That the founders who create extraordinary value often come from unexpected backgrounds because their experiences reveal problems and solutions invisible to insiders.
These investors are reclaiming venture capital as a discipline rather than an identity. They're developing judgment through observation rather than imitation. They're backing founders based on insight and execution rather than pattern matching to arbitrary markers of potential.
This shift isn't just overdue. It's essential for the industry's survival. Because when venture capital becomes primarily a vehicle for belonging rather than a discipline for identifying non-obvious value, it loses its purpose and, ultimately, its returns.
The firms that thrive going forward won't be those that perfect the performance of venture capital as cultural identity. They'll be those that return to first principles, asking fundamental questions about where extraordinary value gets created and who is positioned to create it.
They'll recognize that conformity might provide comfort, but it rarely leads to insight. And in venture capital, insight is the only sustainable advantage.
The strengths that set you apart from Silicon Valley stereotypes aren't flaws to be hidden. They're the very qualities that might allow you to see what others miss.
Use them.