On Being Weird

2025.08.03

CXI

[An Idyllic Summer, Cybermen, Good Peer Pressure, Truth Not Trend, Idiosyncratic Startups, Be Weird]

Thesis: Being you, even if you're weird, is the best decision you can make.

[An Idyllic Summer]

Between my sophomore and juniors years of college, while all of my b school compatriots were off interning at banks and consultancies, I found myself in Maine, near Bar Harbor, sharing a one room cabin with a software engineer, as well as a family of garter snakes.

By that time my then business partner & I had already decided we were to launch our fund, but my partner was taking a proper internship that summer before we began moving in earnest in the Fall.

Rather than getting an internship myself, I decided to do a work away program. I found this very interesting performing arts barn in Maine founded by a dynamo of a man, Walter Nowick.

I did this because I thought I would learn more spending the summer there & self studying than I would during the internship interview & application process combined with the actual internship itself.

My days were pretty idyllic. In the morning, I would help the proprietor, Alan, with whatever he needed done, whether it be designing & printing & distributing flyers, updating the website & facebook page, bookkeeping, cleaning, or setting up for events.

Then, I had the afternoons totally to myself, and this was maybe the most beautiful part of the summer. I would go on bike rides by the ocean a mile or two away, jump in the water and sit in the sand. I spent 2-3 hours every day studying for the FRM, a finance exam I would never take. I traded a bit, too. I read a lot, and wrote a lot, too—60,000 words of a still unfinished novel.

The summer was characterized by silence & focus. I loved it!

But, I don't know if it's possible to over state how fucking weird this was. There I was, a 20 year old at one of the best business schools in the country, and instead of running down the path everyone else was towards consulting or finance, I decided that I would learn more by working at an eclectic collection of barns & cabins in a pretty remote part of Maine and reading and writing and hiking in my spare time.

The best part is, I am still really glad I did it.

The moral of the story is… well, just be you. And do things that you think are the right call, even if they’re weird or out of the box.

[Cybermen]

There is an insane societal pressure towards sameness and superficial differentiation.

Your physical tribes, whether it be your school mates or co workers, are one thing. But, on top that, you also have your digital tribe that are more or less an echo chambers amplifying who you think you want to be until you forget who you actually wanted to be.

It was bad 5 years ago, but it's somehow worse now that everything is amplified by an incessant stream of ai slop. Everything is vacuously personalized, so nothing is.

It kind of makes me think of the Cybermen from Doctor Who. The Cybermen are more or less the og source of the conformist cyborg trope played out in Star Trek with the Borg & probably echoed in a lot of less Lindy material now. The whole idea is that they want everyone to be better, but the same.

In modern day, the fear of this assimilation is similar, but each cyborg is superficially personalized & telling you that you can be too.

If rather than reading & being outside, I would have spent my summer in Maine staring at all of my friends posting about their internships & living in big cities or whatever, I would see that they were all doing similar things and I was doing something VERY different. At the best, I would have felt left out and doubted myself, while at the worst, it might have mutated into strong self loathing.

The pressure on conformity now is more insidious because the "personalization" of having a "custom feed" or a chatbot that "knows you" creates the feeling of difference, but there's still that pressure towards being the same.

And while there are ways to use these tools to amplify genuine creativity, if you don't understand how little this happens in practice, go on a linkedin feed so you can get taken aback by the mono-tonal output of everyone's gpt generated content that they all prompted to “sound like me.”

The point is, it's never been easier to be like everyone else, because the tools we use, both social media and ai, push us towards conformity without us realizing it.

[Good Peer Pressure]

Don't get me wrong, peer pressure can be good.

If some portion of your population is unhealthy due to their habits, it can be very good for the rest of the population to help push them towards healthiness.

And likewise, if a portion of your population is acting abysmally (think racist, violent, deceitful), having the rest of your population push against them also is a very good thing.

I've been in the boat of going overboard on alcohol, and I'm grateful for friends & family who helped me see just how extreme & negative my behavior was.

But what if the bigger portion of your population is the part that’s acting poorly? It's not impossible, as history has shown, for some large chunk of a society to exhibit a negative behavior.

Well, that’s when it's good to be weird. In a social sense, you are a change agent. And, when being different is not dangerous enough to be fatal, it can lead to strong outperformance.

[Truth Not Trend]

So how do you navigate the tricky business of behaving the "right way" when everyone else... well, may or may not be?

By seeking truth and doing stuff you believe in. In other words, perform independent analysis and stick with it for as long as you believe it's right.

That’s why I went to Maine. I analyzed the pros and cons, and realized that the worst case scenario for the alternative path I was taking really wasn’t so bad. Interestingly enough, I underestimated all of the roadblocks that could appear and all of the work that would be required to ultimately build a business, but did pretty accurately gauge that the worst likely outcome wasn’t so bad.

It's not actually about being weird or contrarian for the sake of being weird or contrarian. Rather, it's about doing what you believe is right, after careful analysis, and sticking with it.

A lot of the time, you'll seem weird and might end up at a barn in Maine.

But, in the long run, you might just learn to have independent thoughts that you can arrive at again and again, even when other people aren't.

[Idiosyncratic Startups]

Right now, the most important way that I'm weird is reflected in the way Jack & I run BirdDog. From the perspective of a lot of our peer companies, it is really, really weird.

• We haven't raised money and don't plan on doing so

• We're not touching ai agents

• We want to see how far we can get WITHOUT hiring anyone

• We haven't outsourced anything in the name of 'scale' yet

• We're remote.

• We have no deck explaining our 10 year moat

• We care about customer success & margins more than we care about revenue growth

• All of our marketing is done through one channel, LinkedIn

A lot of these things are the opposite of the decisions that other software startups would make. It's quite strange!

And for that reason sometimes, we second guess ourselves. How could you not when a lot of other people are doing different things?

But, we've done the analysis and keep repeating it, and we really like the trajectory of our business that these decisions is creating.

And, finally, we're at the point where I believe a level headed, non vc indoctrinated third party would look at the numbers and firmly agree.

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[Be Weird]

This post might not be very profound or thinky, but I hope the message is clear…

Just be you & do you & do what you think is right, even especially when everyone else’s actions disagree with yours.

The best thing about getting go at analysis and coming up with your own opinions is that when facts change, your opinion that you derived from facts will change, too. Which, will usually give you a more proactive stance than the crowd has.

Make bets and stick with them until you think they’re wrong, not until everybody else does.

One parting quote from Henry Singleton, the man who pioneered stock buybacks in the 70s. In the 90s, when everybody was finally copying him, someone asked what he though about the buybacks now. He said:

Live Deeply,