Happy Tuesday!
Kia ora Caffeinators,
Every time we have a weekend around these parts there’s a whole bunch of news dropping which I get to retroactively react to on a Tuesday. What’s the lesson? I should never take time off, apparently. Lets get into your Daily Shot now before even more news happens as I write the newsletter.
Here’s what’s brewing in your Daily Shot:
Sudden visa changes rattle US-NZ pipeline
Pod Pick: Investing in the grey zone of dual use technologies
Event: Auckland Bootstrapper's Breakfast / September 2025
In defence of Meta’s live demo fail
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Finn and the CAFFEINE team
Sudden visa changes rattle US-NZ pipeline: ‘Think about the US from day one’ is something you often hear in this world. Cracking the US can put your growth on the kind of hockey stick curve that startup dreams are made of but sudden changes implemented by the Trump administration have potentially put at least one path to the US out of reach.
A wild $100,000 USD ($170,000NZD) fee was summarily slapped on the H-1B, a popular US work visa which allows highly skilled workers to live and work in the US for three years( renewable once). It seems to be a play by the Trump administration to ensure businesses are incentivised to hire local workers into key growth areas but like so much coming out of the US currently, there was a lot of confusion about the roll out.
For a while it seemed as if the fee might apply to existing holders which would have upended many Kiwi founders who have already made the jump using H1Bs but it has since been clarified that it will only apply next to new applicants on the lottery next year. Kevin Park, co-founder of new Crimson Education spinout Concord Visa and man with a very well timed new business specialising in this exact area was on RNZ yesterday breaking it down and would recommend listening here.
He reminds people not to panic and believes this will be resolved with ambitious Kiwis still finding their path to the US. He also notes there are other visa options which get less attention than the H-1B, like the O1 path for those with ‘extraordinary ability’ - which is all you reading this, obviously.
Pod Pick: Investing in the grey zone of dual use technologies - As I listen to the terrifyingly titled book ‘If anyone builds it, everyone dies’ about the potential world ending consequences of our race to build AI, I have been thinking more and more about the ethical implications of technologies which can simultaneously be used for utopian good and dystopian evil. It’s a core problem of building powerful tech which NBR dive into in their latest pod - what are the ethics of investing in technology that has civilian and military applications? Drones, AI, cloud services are all examples of civilian technology with a military application in the "grey zone" of investing. Should New Zealanders take sides or not invest at all? I think for any founder operating in the aerospace sector particularly, it’s a pressing question. Check out the full (unpaywalled) pod here.
Event: Auckland Bootstrapper's Breakfast / September 2025 - Great event for founders next week where entrepreneurs share experiences, swap ideas, and learn from each other, all over coffee and croissants. Each month at the Auckland Bootstrapper’s Breakfast they invite a guest founder or expert to spark the conversation with insights you can apply right away in your own startup journey.
Director, Copywriting & Courses – Words for Breakfast
Helen is one of New Zealand’s most well-regarded copywriting trainers, working with teams from some of the country’s top startups, corporates, and delivering the Marketing Association’s most popular courses.
More recently, she’s been helping founders and writers unlock the power of AI tools to make their writing sharper, more authentic, and more impactful.
At this Bootstrappers’ Breakfast, Helen will help founders:
Find their authentic voice – move beyond the technical pitch to tell the real story of your venture.
Connect with audiences – speak in a way that makes you seen and remembered.
Use AI wisely – learn how different AI tools can complement your voice, the dos and don’ts, and how not to get lost in “Wikipedia/ChatGPT-lingo.”
Why You Should Come
As a founder, it’s easy to get stuck in the technical details of your product. But your story — told with clarity, authenticity, and confidence — is what helps customers, investors, and partners connect with you.
This session is designed for entrepreneurs who want to:
Communicate their journey in a way that resonates.
Build stronger connections with customers and supporters.
Explore practical ways to make AI work for them, not against their authenticity.
Event Details
📅 Tuesday, 30 September 2025
⏰ 7:30 – 8:30 AM
📍 GridAKL / Lysaght – 101 Pakenham Street West, Wynyard Quarter (Opposite Woolworths Metro)
Get your tickets here
In defence of Meta’s live demo fail: Okay we missed this one last week but the internet had a field day with the live tech demo fail of Meta’s new Ray-Ban glasses. There is a certain amount of schadenfreude watching a billionaire squirm as his new device which he promises could make the smartphone obsolete absolutely tanks on stage which I can completely relate to but I argue we need to see more of this not less.
There’s been as trend in these demos towards incredibly sterile, polished and clinically clean presentations where people with expensive teeth and forced smiles say obviously rehearsed lines with punishing faux enthusiasm. That’s if they’re live at all, post covid many tech companies just embrace a pre-recorded stream which is even worse.
I think there’s no point in doing live product demos unless there’s some potential for the unexpected - including things going wrong. Bring on the awkward fails, technical hiccups and awkward pivots. As so much of our online experience is getting flattened out into a bland AI slop monotony, viscerally human moments, even the cringiest ones, should be cherished.
That’s it for today, thanks for reading. Want to get in touch with a news tip, bit of feedback or just to chat? Email hello@caffeinedaily.co