Worklibrary launches AI legal assistant
Plus: Markets react to "Big Short guy" betting on AI bubble
Happy Thursday!
Kia ora Caffeinators, hope you’re well. It’s the time of year where pretty much everyone has quickly become conscious of everything they need to get done by Christmas, so in the interests of fuelling your productivity, let’s get straight into today’s Daily Shot.
Here’s what’s in startup news today:
Worklibrary launches autonomous legal assistant
Report: James Annabell wins EY Master Entrepreneur award
Event: I Wish I Knew with James Sampson
Deel: Getting Compensation Right From Day One
OpenAI launches Atlas in fresh shot at Google
As always, thank you to everyone who has upgraded to a paid subscription or simply recommended Caffeine to friends and whānau. We couldn’t do any of this without you.
Nick and the CAFFEINE team
Worklibrary launches AI legal assistant: In-house lawyers, sit up and take notice. Bootstrapped NZ startup Worklibrary has released its fully autonomous AI legal assistant that promises to remove 30% of your interruptions.
It takes five minutes to set up and can operate as a Slack or Teams channel, or on email, where individuals can go straight to the AI with questions, and it can sift through policies, playbooks, templates etc. to provide answers on the spot or escalate to the right team member if it’s more complex.
Founder and CEO Hayden Mazengarb says “It’s like having a dedicated 24/7 team member who knows your company inside-out, handles all the intake, and only brings you matters that actually need your judgment. This saves hours of manual triage, interruptions, and context switching and lets your team focus on actual value-adding work.”
It feels like this is the kind of product that could easily apply to all sorts of departments, work streams, business leaders etc.. I’m a sucker for sending a “hey, quick question…” message, and the idea of getting an immediate response without interrupting someone else is a game-changer.
They’re targeting 20 new teams by the end of this week and are offering a 50% off deal for anyone who signs up for a free trial before tomorrow. More details here.
Honey maker James Annabell named EY Master Entrepreneur of the year: The EY Entrepreneur of the Year Awards aren’t till next week but they’ve named a range of category winners, who double as finalists for the top gong. Being based in Taranaki, it’s not often I get to shout out winners from the region but this one has been handed to me on a platter so I’m taking it.
James’ journey with Egmont Honey is seriously impressive. It started with him gifting his dad one beehive, and it’s grown into a massive global business with products on the shelves of giants like Costco, Walmart, and Aldi.
He’s among a bunch of Caffeine alumni (is that the right word? Probably not) in the finalists, alongside Simon Malpas, Nick Lissette, Mike Casey, Matt Hayter, Lisa King, Irina Miller, Hengjie Wang and more. The awards night is next Thursday…good luck to the judges trying to figure out how to separate such an outstanding bunch of people.
Event: I Wish I Knew with James Sampson: Last night’s Founders’ Brains on Tap event was seriously cool - more on that tomorrow - so, at the risk of being called an opportunist, it’s an ideal time to promote our next event, which is only a week away.
James Sampson is the founder and CEO of FileInvite, and he’ll share his biggest learnings from growing and scaling businesses, including raising capital, exiting, winning awards, weathering uncertainty and everything in between.
A shout out also for our sponsors Proxi and Kea. These events just don’t happen without fantastic partners, and in this case, we’re extra lucky to have a natural alignment with both of these supporters.
Details
Where: The Commons, 1 Albert Street, Auckland
When: Nov 13 from 5:15pm to 7pm
More details and tickets here - remember, our events are free for Caffeine supporters using the promo code CAFFEINEFRIENDS in the checkout.
Getting Compensation Right From Day One
Startups live and die by their ability to attract and retain great talent. At Caffeine we know seed-stage founders face a recurring challenge: how do you compete for talent when you can’t match corporate salaries? The answer lies in building a compensation strategy that balances cash, equity, and transparency from the start.
That’s where Deel comes in. The global payroll and HR platform has released a free Compensation Guide designed specifically for startups navigating their first hires through to Series A and beyond.
The Guide covers six core elements every founder needs to nail:
Compensation philosophy – defining your market position and pay principles
Salary bands and structures – creating fair, scalable pay ranges
Variable compensation – using bonuses and commissions strategically
Equity distribution – deciding between different forms of options
Founder and early hire pay – balancing minimal salaries with equity stakes
Benefits and perks – offering what matters without overspending
Beyond theory, the Guide walks through practical implementation: how to benchmark against the market, communicate openly with your team, and build processes that scale - and remain compliant - as you grow.
Whether you’re making your first hire or planning for 20, getting compensation right early means fewer headaches later. And in a tight talent market, it might be the edge you need.
Download the free guide here.
Markets react to “Big Short guy” predicting AI bubble: This might be entirely predictable but I find the knee-jerk reaction an interesting case study in human behaviour. You’ve probably seen the news that investor Michael Burry, portrayed by Christian Bale in the movie The Big Short as he predicted the GFC crash, has gone in with a similar $1b+ bet against what he calls an “AI bubble”.
As we’ve reported previously, he’s not the first to pick holes in the way the AI world is developing, but his track record certainly adds weight to the argument. The markets tend to agree (for now), with the Nasdaq and the S&P 500 taking their largest one-day percentage drop in almost a month, and all of the “magnificent seven” AI companies down for the day. Burry took particular aim at Nvidia and data analytics company Palantir; the latter ended up down almost 8% for the day, despite having raised its revenue outlook the day prior.
It’s all a bit cut and thrust, but what’s the bet it’ll be fish and chip paper tomorrow and everyone bounces back until the next time someone prominent pipes up with concerns. Or, the predictions turn out to be right…eek.
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