Hunter WalkModify

2026-10-12 22:26:27

Early stage funds have grown to the size where they want/need to exercise their pro rata rights in multiple rounds. This is a change.

The potential for ‘outliers’ being 10x, 100x bigger than last cycle also means Series B, C etc aren’t *just* 5-10x upside bets. They’re still 20x, 50x, 100x potential in the best case scenarios.

The names also have hot secondary markets so you feel like you are buying pro rata shares that you can flip if needed. It’s becoming a trade as much as an investment.

There are also lots of Fund of Funds, SPV Vehicles, etc that will help a smaller fund take/monetize their pro rata when their core fund can’t support it and/or the return profile of the round doesn’t fit the fund’s mandate. These didn’t exist at this scale even just a few years ago.

Rounds are coming faster and faster so more successive rounds are occurring within a fund’s initial investment period versus being ‘out of cycle’

So expect more potential pro rata conflicts, not fewer, going forward.

There are also large firms who have traditionally been quite aggressive with founders about doing their pro rata when they want, relationship/round dynamics be damned, so this isn’t just about smaller managers.

2026-10-05 06:59:17

Mercury is a leading banking++ software platform for businesses (disclosure: happy small investor in the startup). I’ve found their CEO Immad Akhund to be a thoughtful leader, so was excited to see his recently published “Principles of Writing” to steer communications at Mercury, especially in the face of AI usage. Immad credits Clay’s Varun Anand for the inspiration which I too found to be worthy of review in an earlier post:

I’ll re-publish his opening here, but read the whole thing!

Principles of Writing at Mercury

1. Writing is thinking: Spending time on writing is not wasting time, it helps you process ideas, analyze problems, and explore solutions.
2. Less writing is better: Good writing is concise, which makes it easier to understand.
3. Reading should be easy: If >2 people will read your writing you should spend extra time making your writing good + digestible + clear etc. It is not fair for people reading to do work that the writer could have done for them.
4. Writing is expression: Your writing will be taken as an expression of your identity, so give it the care it deserves and be authentic.
5. Writing is important: Writing is the main way we communicate internally at Mercury, as a remote-first firm. We frame important discussions, and document thought processes and ultimate decisions, with our writing.

2026-09-25 03:40:57

Giving at least a courtesy reply to every initial cold email received was a longstanding goal of mine, especially when they were from entrepreneurs or folks trying to break into tech. The ROI in this commitment was always questionable (although we found at least one great investment this way), but it came down more so to values: when someone clearly put the effort into trying to reach me, I wanted to respect them. People did this for me in various ways and I would pay it forward! The evangelism even extended to preaching repeatedly that the power of a good cold email should never be underestimated. But now in 2026 I might need to discard this principle, and it’s because of AI slop.

“Hi Hunter – You’ve written about [non existent blog post, or something I did write that the LLM misunderstood] and your investments in [often the most random of our portfolio companies] makes you an excellent candidate for our current fundraise.”

Of course there are infinite variations of this, but the number of clearly AI-authored and automated cold pitches has increased so dramatically in the last few quarters that reviewing emails from senders I don’t recognize has gone from moderately enjoyable to just awful. What’s even sadder is these folks are poisoning the channel for people actually doing thoughtful outreach. A digital tragedy of the commons?!!?

How to solve this? Well, since my email client Superhuman bought GPTzero I assume some sort of “send AI emails to spam” option is coming but (a) I’m worried about false positives and (b) this seems like a cat and mouse game. Do we need to rethink some version of sender reputation scoring at an individual level (ie how to determine that the sender is of interest to me by some measure – so you don’t need an intro, but you do need a footprint)? This is more nuanced than general spam filtering.

Until then, I’ll try my best.

2026-09-14 01:59:19

“I don’t know if AI is going to destroy humanity. Neither do you. But here’s what I do know: It’s very difficult to have a sober conversation about this when there’s so much money at stake.”

per usual, very much appreciate Dan Primack’s sensibilities here

2026-08-31 06:19:36

Red light, yellow light, green light. That was the simplest example of “Can we use AI?” policy guidelines I saw while touring high schools with my daughter last year. And now corporate version is starting to turn up, one of the first public ones being Clay’s AI Writing Policy (written by one of their engineers Sophie Alpert). Clay Cofounder Varun Anand shared it via LinkedIn the other day, and ’twas interesting enough to highlight here too. He notes four Guiding Principles

1. You must stand behind every idea and sentence
2. Writing is thinking
3. More time should be spent writing a document than consuming it
4. Longer is not better

More explanation of these, as well as the full policy, are included in the post.

Have you seen other examples of work like this being shared publicly?

2026-08-16 08:01:52

Middle of August reads for ya’.

 or : Do Your Emojis Make You Look Old? [multiple authors/NY Times] – The subhead tells you everything you need to know: When it comes to emoji usage, we’re all just following teen girls. “Teenagers now tend to use  where older people use ” and other pieces of fascinating/hilarious data/decoding, including Fastest Rising.

And of course, don’t sleep on

Chinese tech in Royal Navy drones exposes UK defence supply chain dilemma [Carly Page/Resilance Media] – From emojis to sovereign supply chains – I’m just that kind of guy. So it turns out that the UK military has been using British manufactured drones which promised ‘no Chinese components’ but (a) they had Chinese components and (b) it was discovered these components were sending “heartbeat” data (whether camera was on or not) back to an IP address in China. We’re entering a different age of security due to global politics, AI, supply chain risk, and the pervasiveness of software/chips in literally everything.

AI Is Rewiring South Korea’s Careers, Dating and Culture [multiple authors/Bloomberg] –

South Korea is dealing with similar issues to us – maybe even more acutely and rapidly:

“The more than 98% of workers who aren’t in the chip sector are increasingly feeling like bystanders to the bonanza. In a bid to spread the gains, the government plans to establish a dedicated fund to finance long-term investments in strategic industries, education, regional development and youth.The central bank has warned that gains from technology, equity markets and AI are disproportionately benefiting the affluent.”

New Media is Insider Media [Anu Atluru/Working Theories] – “Insider Media is the opposite of journalistic media—outsider media—made for outsiders by outsiders. Outsiders will call Insider Media an echo chamber or bubble, but the proximity is very much the product.” Proximity is the product. That’s such an interesting framing! There are 30 observations in this essay, and obviously I’d recommend reading them all. (for context, things like TBPN are considered ‘Insider Media’ by Anu, who was also early at Clubhouse).

Can Robots Save an Aging Japan? [multiple authors/NYTimes] – Turns out traditional cherry blossoms are grown and harvested by an aging population, without enough young people to replace them. This is true of several labor verticals within Japan (and I assume eventually the case in many below replacement rate societies).

“We had to do something,” said Mitsuya Kaneko, the head of the Nishikawa cherry blossom farmers’ union, whose parents, aged 75 and 84, still plod through the snow to prune and package winter sakura in a largely unheated shed. “We cannot just die out.”

The solution? Potentially robots.

Enter Monster Wolf, a made-in-Japan, fur-sheathed contraption with flashing red eyes and a piercing vocal range. As the couple’s cabbages grew sweet and crisp last season, Monster Wolf reported for duty courtesy of the Yamagata city government, emitting an assortment of sounds every half-hour that fluctuated between vastly annoying and genuinely terrifying. Motion also sets off the machine’s cacophony. The Sakurais were able to work without fear of an attack [from bears].

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Have a great rest of the summer!