The Funds Doing Something Different

I spent this week having compliance review for a fund's marketing materials.

Understandably, this has been painfully boring. Which naturally got me thinking about the opposite - what it looks like when funds do something fun, or weird.

I also believe that being weird matters now more than it ever has.

“Weird” doesn’t have to mean comedic, or cringe. But non-standard, specific to you.

What can you do that is hard to copy? and how to think about that as a deliberate part of your content strategy?

The asset class for risk takers, presented as blandly as possible

Venture capital brands itself as the asset class for risk takers. The founders it backs are supposed to be unconventional, contrarian, willing to look wrong before they are right. And yet the way the industry presents itself - content, language it uses, the formats it defaults to - is often startlingly flat. Buzzwordy thought leadership or content optimised for inoffensiveness that it says almost nothing.

This was not always the case.

During venture’s rise to ‘adolescence’ (2000-2015) startups remained for eccentric people, and it showed in how those people showed up.

First Round Capital used to produce an annual holiday video that was anticipated across the tech industry - peep the comments from Jason Calacanis.

Brad Feld made a rap video called I'm a VC. It is 2010-coded and cringe by today's standards, but it is also the kind of thing people still reference, which is more than can be said for most VC content from that era or any other.

The industry used to be willing to look a bit silly in public. That willingness has largely disappeared as the asset class has grown up, institutionalised, and started taking itself very seriously…

I'm not saying make a rap video. I'm saying the impulse behind it, to demonstrate humanity or at least a real POV, is worth recovering.

Why weirdness matters more now

AI is also about to make that choice - between the safe and the specific - more consequential.

There's a particular trap in VC content specifically. The industry attracts people who are smart and who have built a professional identity around being right. That makes the instinct to only publish authoritative or defensible content very strong. But being right all the time in public is not the same as being interesting, and interesting is what compounds.

We touched last week on how the volume of technically adequate content is going through the roof.

AI makes B-tier writing easy.

The baseline question for VC content was once - are you publishing anything at all? The new bar is whether anyone cares when you do.

When competence gets commoditised, distinctiveness becomes the scarce resource. So differentiation moves to taste, originality, weirdness, specificity, and that final 10% of human flourish. That last layer matters disproportionately, where the work becomes personal, strange, unpredictable, and unmistakably human.

What authentic weirdness actually looks like

Examples of original VC content are not weird in a random way. They are weird in a specific way - they reveal something true about the fund that a more conventional format would have buried.

Long Journey Ventures raised their most recent fund at $181,818,181.81. A deliberate number, because 18 represents life in Jewish numerology and they wanted even their fund size to signal something about who they are.

Long Journey’s tagline is "second believers in the magically weird." They’ve back SpaceX, Uber, Airbnb - they take money seriously, and they say so explicitly. But they also want to show that they have fun doing it, and that they are the right people for founders who are themselves a bit unconventional.

You may remember their GP Arielle Zuckerberg (yep, the youngest sibling) published a piece called Rizz and Tizz laying out their framework for what they look for in founders, in language the average VC firm would go near.

The piece is not just memorable because it uses internet-native language. It is ironically much clearer and more useful articulation of an investment thesis than most of the polished, buzzwordy frameworks that funds publish.

It cuts through corporate obfuscation by being genuine. The weirdness is the clarity. A founder reading it immediately understands what Long Journey values and whether they fit - which is exactly what that content is supposed to do.

Likewise, Yohei Nakajima announced Untapped Capital Fund 2 with an super original video made for $120 using Runway + posted a thread about how he made it.

The video is memorable in a way a static announcement never would be. More importantly, the format and the fund's thesis are the same thing. Untapped's identity is built around building in public and playing with the latest technology (check out his build in public log here).

Making a weird AI launch video and documenting the process is not a departure from that strategy. It is the strategy. When the content and the investment philosophy are inseparable the content works.

What weirdness is doing

Attention is the shallow version of the argument...

Yes, Lomax Ward's video this week framed around "don't raise from outside ventures" stops the scroll in a way a standard raise announcement would not.

Yes, also this week Slow Ventures hosting an etiquette conference gets talked about in a way a panel discussion would not. (btw wrote a whole blog post about Spacecadet here)

Yes, both last week, Space Cadet’s fictitious AI Ryanair ad gets 10 million views (!) Bulletpitch (and Antler) ran their pitch event as a carnival - where sponsors had to run a game to get access to founders - is more memorable than any conventional sponsorship package.

BUT… attention is not why this matters. The deeper thing these pieces of content are doing is showing who the fund actually is, in a way that is almost impossible to convey through a thesis post or an investment announcement. It is very hard to get across in writing what a fund is like to work with, what the partners are like as people, what the culture of the firm actually feels like.

A video, a weird event format, an unexpected frame… these do that job in seconds.

and if all that is too avant-garde for your serious or old school fund, consider…

Founders Fund interviewing Grimes rather than another tech founder, then producing Anatomy of a New World - a series exploring questions like how to build an ocean or what sex looks like in space a hundred years from now - are signals to Founders who resonate with that worldview to find their way to Founders Fund.

The practical question worth asking of any piece of content you make…

Does this show who we actually are? or only what we invest in - how can it answer who we are as people, and what it would be like to work with us?

The barbell and the budget

I am not advocating weird content as an all-or-nothing decision (which is why most funds never do it). The better frame is a barbell.

One side is the baseline - consistent, reliable content that builds the muscle and the audience. The newsletter, the investment announcement, the partner thesis piece. Not exciting, but necessary. You cannot do the weird stuff without the foundation, and trying to be weird without consistency just looks erratic.

The other side is a deliberate experimental allocation. A portion of your resources pointed at things that might not work. UK fund Haatch is a recent example of how to try things, without completely going off the course.

But all this is to say, most funds spend everything on the safe side and wonder why nothing breaks through. The question worth asking honestly is whether you have any budget (time, money, attention) allocated to trying things that might not work.

For most funds, the answer is no.

The cost of getting this wrong is also lower than it used to be. Yohei made a memorable fund launch video for $120. Space Cadet made a 10,000,000 view piece of content with AI tools. The production barrier to experimentation has dropped significantly, which means the risk calculation has shifted.

Why this gets more important

As AI takes on more of the functional work in venture - market underwriting, deal flow filtering, initial screening - the human differentiator becomes culture, personality + being interesting.

Content that is weird and specific is a preview of that. It is evidence, before any meeting has happened, that there are real humans here with real opinions and a genuine point of view on the world. If VC surface-level communication gets automated, that evidence becomes more valuable, not less.

The industry used to know this. The people who built venture capital in its early days were, by and large, weird - and proud of it. The asset class has grown up and in doing so has largely stopped expressing that, but founders it wants to back are still unconventional and original.

Try things, at least its human to get it wrong.

Laurie, Refinery Media

If you made it all the way through, thanks so much for reading! Several hundred VCs now open this every week. If it's helped you think differently about marketing, Venture, or storytelling, please send it to someone in your orbit.

• What is Full Stack VC Marketing?

• VC Marketing in 2035: What Changes When AI Does the Work

• The Future of VC Marketing is Interactive