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.
Ugh
“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.
“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.”
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’sAI 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
You must stand behind every idea and sentence
Writing is thinking
More time should be spent writing a document than consuming it
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.
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].
Picking Rocketships Is a Bad Career Strategy [Molly Graham/Lessons] – We all know the legendary advice from Google’s Eric Schmidt to Sheryl Sandberg, “When you’re offered a seat on a rocketship, you don’t ask which seat. You just get on.” While it certainly worked well for Sheryl, Molly suggests a different approach to career management: “My ultimate litmus test for a job is: If this company struggles or fails, will I still be glad I took the job?”
Why? Because narratives – and company trajectories – can change quickly. But a good decision isn’t simply about the financial outcome, it’s about the lessons, the people, the experience, and the reputation effect.
The Creator Economy Has a New Middle Class [Melos Ambaye/Bloomberg] – Covering how a variety of monetization streams (affiliate links, brand deals, loyal fans) has helped influencers beyond the top of the pyramid construct annual incomes at/above salaries they would otherwise earn from standard jobs. It’s a lot of hustle though and most still don’t come anywhere close to these levels.. That said, one of the most fun implications is that you can niche up – becoming a voice in areas that otherwise might not have pop culture level awareness – like dentistry, accounting, etc
Why People Hate Capitalism [Vijay Pande] – Entrepeneur turned VC Vijay Pande has been writing a series of what is ailing our asset class and capitalism more generally. Here he notes how capitalism has become captive to entrenched rent seekers, which pull opportunity away from the individual. While some might disagree with one of his optimistic takes [AI is going to kill some – but not all – of the rackets], I love him engaging in this question and evangelizing that there *is* a massive problem in today’s economy and culture.
Knockoff– Ok sharing this one because it’s fascinating to me. A Chrome extension which tries to focus on product quality while you shop Amazon: “Knockoff filters trademark-squat pseudo-brands (the SZHLUXes and HORUSDYs) out of Amazon search, and can tell you when an Etsy “handmade” listing is mass-market catalog stock. What’s left is brands with a reputation to lose.”More details in this Fast Company article.
The Post-Agentic Founder [Rex Woodbury/Digital Native] – VC Rex Woodbury shares his list of ‘post-agentic’ founder attributes – that is, what are some things he notices/looks for in this wave of startups. To best enjoy this post don’t think of it as canonical but rather what one investor believes fits the type of founder he seeks out. One of my favorites:
Founders who are good at RTS games. The best chess and StarCraft players don’t win with a single move or unit. They win by maintaining a model of the entire board, allocating scarce resources, sequencing actions, and directing many pieces toward a unified objective. Post-agentic founders do the same. They are unusually good at decomposing large problems, assigning work across agents, deciding which tasks should run in parallel, and knowing when to intervene themselves. It all becomes about orchestration. And that only grows in importance as the agents can do more and more.
TLDR: I’m fanboying for Junova because it uses AI to claim $$ credit when an airline ticket drops below the price I’ve paid for it
This Bloomberg article basically sums up why I keep pushing Junova on you all: Bargain Flights on Busy Routes Face Squeeze Due to AI Pricing. From the report: artificial intelligence is enabling carriers to change seat prices more quickly by weighing dozens of variables in real time, helping capture more revenue while shrinking the pricing gaps that once allowed travelers to find bargain fares.
There are several products that automatically track the flights you’ve booked (once you submit them) and them claim flight credits for you if the price drops. This works on US flights for the major carriers. Of these I’ve chosen to use Junova because
a) I know the founder but am not an investor in the company or receiving anything additional for posting about it
b) It has worked really well for me so far across three airlines (Delta, American, United)
c) The business model makes sense to me – there’s no subscription fee or payment upfront. It basically charges your credit card 20% of what value it claims for you. Example, let’s say it gets me $100 flight credit on United. I should then expect $20 charge on my credit card. This seem fair.
So far I’ve saved $3,000+ on tickets for me and my family in less than a year. And the people using my referral link have saved $13,000+. If you use my referral link we each get $25 credit [eg in the United example above your credit card wouldn’t get charged]. I like when people use my link not so much for the $25, but because it allows me to see the total amount of money my friends have saved which is cool. But whatever, use a generic link if you want. I rather everyone just arm up against the airlines!
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.
