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A seed stage venture partner at Homebrew, previously managed consumer products at YouTube and worked at Google and Linden Lab.
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AI: “It’s very difficult to have a sober conversation about this when there’s so much money at stake”

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

Does Your Startup Have an AI Writing Policy Yet? Here’s One from Clay.

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?

AI is Changing South Korea Even Faster Than it’s Changing the US; Why 🥀 Is The Fastest-Rising Emoji; How Robots Might Save Cherry Blossom Season; +++ [link blog]

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.

Fastest Rising Emoji usage

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].

Japan robot

Have a great rest of the summer!

Why “Grab Any Seat on the Rocketship” is a bad career strategy; this VC thinks people are right to hate today’s capitalism; look for founders who play RTS games; and a Chrome extension which blocks slop ecom brands ++ [link blog]

2026-08-03 00:40:39

Hot August URLs coming right up!

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.

Have a great sunday!

Airlines Are Using AI to Maximize Prices – Here’s How You Fight Back

2026-08-01 01:46:21

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!

Startup Kool-Aid; Why You’re Making Enough Money but Still Anxious; $100 Million in Odyssey Popcorn Buckets; the World’s Best Fake $50 Bill, +++ [link post]

2026-07-26 05:57:09

When I grew up on the East Coast, August was still summer, but here on the West Coast the kids start school so early! Anyways, some July URLs for you.

Salty, Buttery, Astonishingly Lucrative: The $100 Million Market of Popcorn Buckets [Nicole Sperling/New York Times] – I don’t go to movies often and I rarely eat popcorn but the fanboy side of me throbbed a bit looking at these increasingly ornate (and sometimes weird) ‘collectibles.’

Popcorn Buckets

The Fun Shortage Is Real, and It’s Making America Miserable [Ben Steverman/Businessweek] – Oh this is a great read that has a bunch of interesting observations/questions about the decrease of affordable public recreational activities. Obviously some of this is nostalgic love for the chosen venues of past generations, but it’s also, um, not wrong? K-Shaped Recovery moment too – with upscale pricing going through the roof and funding for municipal spaces falling in urban and low income communities.

The Kool-Aid Must Flow [early days] – The authors (Camille and Brie) make the case that the importance of standing for something as a startup is greater than ever. Note, they’re not evangelizing for a particular set of values, nor are they suggesting ‘being controversial/noisy’ for its own sake. Rather they’re talking about core beliefs that are consistent, interesting, and articulated well enough to create a gravitational pull. They also include a set of tactics for ‘getting the Kool-Aid flowing.’

I make good money. Why do I still feel like this? [Hanna Horvath/Your Brain on Money] – Especially during periods of economic mania [aka current state of AI investing/startups in tech], having a good handle on your own attitudes about money/wealth is really important. Otherwise you, at the very least, walk around anxious and unsure, let alone unmoored (which can result in poor short-term decisions). Hanna here makes the case that we’re experience an unmooring; that the middle class itself was the result of a policy experiment, not a permanent aspect of American capitalism. And its shrinking (disappearance?) results in a sense of precariousness with ones position as the country sorts into Have So Much and Never Have Enough.

The Hunt for the Counterfeiter Trying to Make the Perfect Bill [Yudhijit Bhattacharjee/New York Times] – Guess where the best counterfeiter of the US $50 bill hails from…. Russia? China? North Korea? The US itself? Until recently the answer may have been Colombia.

It was clear that Rodriguez took pride in his work as an artist. “He wanted to make the perfect bill,” Prieto said. Trying to design a flawless bank note, he told investigators, was a passion that helped him relax.

How One Man Makes Millions Selling Coins Live on the Internet [Dalvin Brown/Wall Street Journal] – “I’m just here selling coins,” Bergstrom said, “but also being people’s therapist.” With platforms like Whatnot, every collectible category feels like it has exploded – if not in total volume, at least in what the whales can do. “The coin-selling category ranked third by sales volume [on Whatnot] over the past six months, according to Resellbot, an e-commerce analytics firm.”

Enjoy your weekend!


My friends have saved $13,000+ since I posted this link!

Someone told me this was jarring to see on a VC blog – what am I shilling for an Junova? Well, I’m not being paid and I’m not an investor in the product. I just think it’s brilliant and effective and I like the idea of using AI to “fight” against big business pricing models. ¯\_(ツ)_/¯

Tip DON’T LET AIRLINES RIP YOU OFF ESPECIALLY AS OIL PRICES CLIMB: I’m using Junova to track purchased airline tickets and auto-reclaim credit if the price drops. It was started by a friend and so far has recouped $3000+ of American and United credits for me. Their business model is: service is no cost, but if they successfully get you credit, they charge 20% of the value to your credit card. If you use this referral link, your first $25 of fees (ie $125 of flight credit) is free. Let me know how it works for you!

Recent savings

My total to date