All Eyes on Apple

Google inks $920M/ yr deal with SpaceX, OpenAI discussing deal with White House, Bending Spoons files for IPO

Jun 08, 2026

Happy Monday.

We’re live on YouTube and 𝕏.

The current thing in tech and business is Cloudflare’s Matthew Prince accusing Khosla Ventures of shady behavior during the company’s fundraise for its Series C.

Today’s lineup

Planet Co-Founder & CEO Will Marshall at 11:45 AM
U.K. House of Lords Member Dambisa Moyo at 12:00 PM
Stematic Labs Co-Founder Samuel Hume at 12:30 PM
Helion Founder & CEO David Kirtley at 12:45 PM
Generalist AI Co-Founder & CEO Pete Florence at 1:00 PM
The Interaction Company of California Co-Founder Marvin von Hagen at 1:10 PM
Antares Co-Founder & CEO Jordan Bramble at 1:25 PM

Run of Show

WWDC Kicks Off Today

What happened: Apple’s annual WWDC (Worldwide Developer Conference) started today and will run through Friday. Tim Cook just kicked it off with the opening keynote. The theme for this year’s conference is “All Systems Glow.”

We’re finally getting answers about the next version of Siri. I think expectations are high, because Apple has taken so long to fully get in the game here, but they aren’t wildly miscalculated. It’s all achievable. Models are good now, so make them available at the click of a button, and users will be happy. Google AI search overviews proved that rolling out LLM responses can be nerve-racking, but ultimately isn’t rocket science. Just spit the text out where people expect the answer, there will be funny viral hallucinations, but those won’t actually show up in the user metrics. Your PR team will have many heart attacks though because you’re not in the world of deterministic outputs yet.

The other big questions are around open ecosystems. Will Apple lean into the OpenClaw Mac mini boom at all? Will there be a pivot around vibecoding apps in the iOS app store? (We discussed this with John Gruber on May 29th)? Will native iOS apps from AI labs have more access to iPhone functionality via Siri App Intents or other previously limited APIs? Excited to dig in this week. We have some great guests lined up to cover it. — John

Jobs up, tech down

What happened: Friday the Labor Department reported that the US added a seasonally adjusted 172,000 jobs in May, and that the unemployment rate remained unchanged at 4.3%.

The bubble popped on Friday, the worst day for the Nasdaq in more than a year. 4.2% down. It’s over. Today, we’re back, up ~1.5%. It’s officially 2003.

Quick explanation of what happened here. First, the US labor market is really picking up. 172,000 seasonally adjusted jobs added in May, according to the Labor Department. Third month in a row of strong gains. Despite the herculean efforts of blackpilled AI leaders, tech just can’t seem to displace American workers. Good news, AI job apocalypse cancelled, at least for the month of May.

But inflation is rising, the closing of the Strait of Hormuz has spiked the cost of gas and overall prices have been increasing more quickly than the Fed would like for some time. This makes the likelihood of a rate cut more and more unlikely. In fact, it looks like we might be in rate hike territory soon, and that’s always bad for tech companies that have earnings forecasts that stretch out far into the next decade. The silver lining in high rates is at least the Fed has something useful in the tool chest in case the economy does slow down. Still, rocky territory in the market for the foreseeable future and some major tests coming down the pipe with somewhere between one and three trillion dollar IPOs currently in the works. — John

VC horror stories

What happened: Greg Isenberg kicked off a big discussion about founders’ bad experiences with venture capital, and a number of high profile firms/ VCs caught strays. Mercor CEO Brendan Foody detailed what he calls the “Sequoia scam,” and Cloudflare’s Matthew Prince accused Vinod Khosla of offering to invest in his Series C only if he would fire a few of the people at the pitch meeting, who had just left the room momentarily to go to the bathroom.

Lots of chatter on the timeline over the weekend about “VC horror stories.” Certainly a discussion worth having, but Silicon Valley has always been so high-growth and positive-sum that relatively good behavior is usually the equilibrium. Even when a startup fails, investors can’t write off the founder entirely, because they might start the next generational company, so they might give on a founder-friendly acquihire or help them land somewhere to earn a paycheck.

There does seem to be a wide gap between VC pitch horror stories and VC board action horror stories. I have much less sympathy for the former. Your job as a founder is to sell equity from time to time, it’s your job to find investors who want to purchase that equity with cash (VCs). You need to reference check them beforehand, make sure they are a fit, think through their competitive investments, and keep them entertained (and awake) during the pitch. VCs shouldn’t be disrespectful (and literally falling asleep certainly is), but this is far from the worst thing that regularly happens in the course of growing a business.

Here’s a tip for keeping VCs awake during pitch meetings: analogize your business to an Air Horn. “Like this air horn, with one simple button press, we amplify your business by 100x.” Then blast the air horn. Works every time. Here’s a link. — John