Kiwi founder pay data revealed and an interview with Twitter employee #1

PLUS: A check in on Apple VS Epic and is a social media ban coming for NZ?

Welcome to mid week!

We made it to hump day and I feel like as a reward we should all get the rest of the week off. Failing that, at least help yourself to a shiny newsletter to help you through your morning.

Kicking off today, for paid subscribers we have an interview with Twitter employee #1 and an ultimate insiders look at one of the most consequential and controversial social media companies on Earth.

Considering the big social media news yesterday, that timed out well, huh? And for regular subscribers, not to worry, we have a full newsletter free to read with some fascinating data on founder pay first up.

Here’s what’s in your Daily Shot of news you don’t want to miss

• Twitter #1 on how the bird was broken and what should come next

• NZ’s first founder salary survey lifts the lid on pay

• National moves to ban social media for under 16s (sort of)

• Apple Vs Epic games takes another turn but looks like Apples losing

• Podpick: From Canvas to Clove, how Anna Gerrerro is redesigning how we cook at home

Got a tip, press release or just a comment? Drop us a note: hello@caffeinedaily.co - we love to hear from you.

Finn & the Caffeine team

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Twitter’s employee #1 on how the bird was broken

“No-one ever sets out to make the world worse with what they’re building,” Evan "Rabble" Henshaw-Plath told me at the start of our interview.

It’s a pretty innocuous statement from most in the startup space. But when you were the first employee at Twitter and the person who hired Jack Dorsey, it hits a little different.

Rabble, who features in a recent documentary ‘Breaking the Bird’ on the tumultuous history and present day of Twitter, kindly sat down with Caffeine recently to share his unique perspective on one of the most controversial and powerful social media companies on Earth.

I got to hear his insights into the platform’s evolution, its unexpected consequences, and his observations on the New Zealand startup ecosystem now that he lives down under

I started by asking him to reflect on the difference between the Silicon Valley that start up founders might be imagining now, and the ecosystem as it existed back in the early oughts.

“What is really most surreal about that period like 2004 to 2008 in San Francisco is how small it was. We are not talking about a large industry. There was no abundant venture capital. There was no one moving there to do a startup. It was basically a place where the startup boom in the late 90s and early 2000s had come and gone,” Rabble explained.

Paid subscribers can check out the full interview below

NZ’s first founder salary survey lifts the lid on pay, wellbeing and the gender gap: A fascinating report has just dropped this morning which reveals for the first time what Kiwi startup founders are paying themselves. LiveRem and our mates at Oxygen Advisors (who wrote those great blogs for us last week) have dropped the New Zealand Founder Pay Report 2025 which analyses anonymised payroll data from founders across the motu at Kiwi startups and scaleups earning anywhere from under $1 million to more than $10 million in annual revenue and employing teams that range from a handful of people to well over 100.

Key Findings in the report

• Average time to paycheck is 29 months and revenue drives reward: Founders of companies earning over $10m in annual revenue earn twice as much as those under $1m.

• 50% of founders pay themselves more than $195k: The average founder pays themself $205k per year, or $195k at a median measurement.

• Gender pay gaps persist. Male founders are paid, on average, more than women.

• Roles and location matter. Other pay gaps include location (more in Auckland) and skillset (‘Technical founders’ earn less than CEOs.)

• Long-term rewards often trump immediate paybacks. 42% of founders are taking home less than at least one member of their team and successful exits typically don’t come quickly - 56% of founders exited after 6 - 7 years.

Check out the full report here.

National moves to ban social media for under 16s (sort of): Well, considering the topic of our lead article today, let’s take a rare foray into domestic politics. The National Party is proposing a ban 16-year-olds from accessing social media by forcing companies to use age verification measures.

National MP Catherine Wedd has put forward a members' bill which would follow Australia's lead on cracking down on the social media giants. Notably, this was announced with the PM at her side giving it his full, or at least vocal, support.

This is a real nerdy side bar here but currently this currently doesn’t actually mean much in terms of it becoming law as a members bill has to be drawn by ballot out of a literal biscuit tin in parliament before it can be debated and moved through the legislative pipeline (It’s a whole thing, just look it up but tl;dr it’s super cute and I kinda love it for our democracy).

Luxon said he wanted to explore putting this forward as a government bill, meaning it could get passed quicker but that hope was scuppered by his coalition partner David Seymour who said ACT will not support it.

That means it will need support across the aisle if its going to pass and currently Labour are making broadly positive noise sin that direction but there is going to be a hell of a lot of detail and debate to be ironed out before anything moves here, I imagine.

While it might not seem like earth shattering news to the founder community, I think it’s one of the most potentially consequential intersections of politics and tech we will see for some time.

It could set NZ directly at odds with the most powerful companies in the world and radically change the online life for many young Kiwis. Check out this wrap from RNZ for more details.

Apple Vs Epic games takes another turn but looks like Apples losing: It’s almost Thursday and I like checking in on the broader tech space at least once. Amid all the chaos and noise you might have missed this story but one of the world’s tech titans has been locked in a bitter battle with a gaming giant for years and recently suffered a major loss.

Very basically, Epic games - the Fortnite people - sued in 2020 alleging Apple had monopoly power over its app store and too much control over transactions in applications. The judge agreed and a prior order required Apple to give developers more power to steer app users to non-Apple payment options that avoid Apple's 30% commission.

Now in the past week that same court has ruled Apple failed to comply, with the judge saying “Apple sought to maintain a revenue stream worth billions in direct defiance of this court’s injunction,”

Now she has ruled Apple could no longer take commissions from sales outside the App Store and cannot write rules preventing devs from creating buttons or links to pay outside the store or discourage users from making purchases through warning popups.

It essentially removes all in app payment restrictions in the US app store which could be transformative for businesses on there to the tune of many billions. NYT has a good wrap here.

Podpick: From Canvas to Clove, how Anna Guerrero is redesigning how we cook at home - Another cracker episode from our friends over at Blackbird in their Wild Hearts podcast series. In this episode, Wild Hearts guest host, Silk Kadala - investor at Blackbird - chats with Anna Guerrero, founder of Clove, a cooking app that’s reimagining how we cook at home.

You might know Anna from her nine years scaling the creator marketplace at Canva—but it was a stint as a pasta chef in the Dolomites that ultimately set her on the path to launching Clove.

🔍 In this conversation, they cover:

📲 Why Clove’s approach to AI is more whisper than shout—and why that matters for creativity

📚 Building for creators: how Clove is giving food bloggers, TikTok cooks and chefs a new way to publish and earn

🎯 From pitch decks to real traction: Anna’s high-stakes decision to pause Clove’s creator program and set a new quality bar

🚀 The leap from Canva exec to culinary school student—and what working in a Michelin-starred restaurant taught Anna about product

🧠 Low ego, high initiative: what Clove looks for in early team members and building a culture of adaptability

🧭 What it means to follow the dots—why you don’t need to have it all figured out to move forward

🍽️ The long-term ambition: turning Clove into the global go-to for “what’s for dinner?”—with a billion recipes cooked through the platform

Listen to the full pod here.

Considering the news above, thought it was fitting to finish on a Jack Dorsey quote from when he was much fresher faced and full of optimism.

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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