Your Startup’s Eccentricity is its Most Valuable IP
The power of defined weirdness
I’ve spent the better part of twenty years in this industry (infrastructure, product, support, leadership, you name it) and I have seen several cycles of boom, bust, and brutal conformity. Every few years, we watch as a thousand ambitious people try to mimic the one or two companies that actually succeeded. We chase the funding formula, the management structure, the exact brand shade of teal (and its accompanying emoji in Slack). We normalize.
And yet, if you look back at the origins of anything truly revolutionary (the shifts, the disruptive moments, the things that truly moved the needle) you find one shared characteristic: it was profoundly, unapologetically weird.
“Weird” is a key differentiator. Keep it weird. Or better yet, define your own weird.
The Weirdness of Connectivity
To understand this, you have to remember where this whole connected thing started. Long before the Internet as we know it, before venture capital had codified how to build software, there were thousands of isolated, single-line computer systems. I’m talking about the Bulletin Board System (BBS) era.
Every single BBS was a kingdom ruled by a SysOp (System Operator), and that meant every BBS was defined by that person’s personal interests, neuroses, and strange coding hacks. One system might be dedicated purely to discussions of Commodore BASIC (the oldest of tech nostalgia) while another was a pirated file-sharing hub with an ANSI graphical theme ripped straight from a 1980s heavy metal album. The point is, there was no central playbook. If you wanted to run a successful board, you had to lean into your specific eccentricities. Your weirdness was the reason people paid for the long-distance call to connect.
My first “job” was when, as a young teenager, I “moderated forums” (politely asked an older teen in my small town to swear less, if possible), “monitored uptime” (called the SysOp’s mom to unplug and replug the modem when I couldn’t reach the BBS), and “strategized on the product’s direction” (went to my friend the SysOp’s house, ate pizza, and looked for new games to add to the BBS).
Later, as the World Wide Web scaled, the biggest disruptions weren’t just better technology (though that helped). They were decisions that defied convention. The speed at which Netscape released its early browsers, the rapid introduction of non-standard HTML extensions, the sheer audacity of bundling a graphical browser with an operating system—these were commercially weird moves that defined an industry for a decade. Disruption, by its very nature, demands non-conformity.
The Empathy Engine is Weird
In today’s startup culture, “weird” isn’t just a product decision; it’s an emotional imperative.
I spend a lot of time writing about emotional intelligence (EQ) and empathy in the tech sector, because for too long, the default professional persona was the silent, hyper-rational, stoic worker. But that is the ultimate form of conformity, and it creates toxic, brittle environments.
When I talk about defining your own weird, I mean identifying the thing that makes you an outlier in a meeting. Is it the courage to ask the “dumb” question (which, invariably, half the room also wants to ask)? Is it your ability to pause a chaotic sprint retrospective and ask the team how they are feeling (not just what they are shipping)? Is it recognizing that your company’s obsession with a specific metric is actually hurting morale (the ultimate infrastructure issue, by the way) and saying so?
In the context of the modern workplace, authenticity is professional weirdness.
The moment you choose to apply a deep, emotional skill (something historically dismissed as “soft” or “not scalable”) within a system built on hard logic, you are defining your own, highly valuable weird. You become the human firewall (protecting against burnout) and the cultural catalyst (ensuring people feel seen). You stop trying to fit the mold of the 10x developer or the MBA-defined leader. You become a 1x human, which is always, always weirder, and infinitely more valuable.
The future of work is not about efficient mimicry. AI handles that beautifully. Our job is to inject the undefinable, the unexpected, the non-standard variable into the equation. It is the only way to build products (and companies) that cannot be easily copied.
Stop aiming for polished perfection. Find the specific, niche, slightly embarrassing truth about your team, your product, or your own leadership style. Build a moat out of that magnificent, singular weirdness.