Two years and a $250 million lawsuit later, Apple’s AI Siri revamp is on its way to your phones and laptops and even your mixed reality headset, if you happen to be one of like three people who actually uses the Apple Vision Pro. Apple revealed a slew of new information at Monday’s WWDC keynote about these long-awaited, AI-powered updates that can take advantage of the fact that our hardware is supposedly “built for Apple Intelligence.”

To be honest, it’s hard for AI to impress me enough that I’ll use it in my day-to-day life. I still don’t trust LLMs to provide consistently accurate information, I find it ethically untenable (and uncool) to use AI to help me write, and I don’t feel the insatiable urge to know what I would look like as a Studio Ghibli character. But every once in a while, the promise of AI tempts me.

That’s how I felt watching Apple’s Siri AI demos, which depict a world where your phone comes with an always-on, constantly-working assistant who knows everything about you and can help you keep track of all of the conversations happening on like 12 different apps on your phone at any given moment.

To paraphrase Katy Perry, it feels so wrong (what are the privacy implications?), but it also feels so right (I am so overwhelmed by my phone and am begging for help parsing it all).

I want Siri to be my own personal Emily from “The Devil Wears Prada” — a “second brain” that anticipates my needs before I even know what they are. I want Siri to read my texts and automatically make an event when a friend and I decide we’re going to meet up for dinner on Thursday. I want Siri to remind me when I’m walking past CVS that I have a prescription ready for pickup. If I forget to reply to an important work email, I want Siri to remind me that I didn’t write back yet.

Siri AI won’t be able to do all of that out of the box, but it’s moving in the right direction. In one example at WWDC, Justin Titi, an Apple senior director working on AI engineering, asks the smart assistant to remind him of the dessert that his daughter mentioned recently. Siri searches across Titi’s phone to find a text from about a month ago, when his daughter mentioned that she wanted to make coconut cookies. It’s simple, but asking Siri to find that message saves time, rather than scrolling up through an entire month of conversation looking for that one specific text.

The new-and-improved Siri is designed to use “personal context,” which refers to any information you put into Apple-native apps, like iMessage, Notes, Calendar, Mail, Photos, and more. Siri will also be aware of what’s on your screen, so for example, if you scroll past a picture of a nice park on Instagram, you can ask it to find out where that park is. (We still don’t know if Siri will be able to integrate into non-native Apple apps; it seems like it might be up to the developers to make that happen.)

There already are apps like Poppy and Poke that try to create this kind of mobile, agentic AI. But the paradox of these AI personal assistant tools is that you have to give up a lot of personal data and privacy to make them work correctly, which may just cause you more trouble (remember that time when a Meta researcher ran OpenClaw and accidentally deleted her entire inbox?).

I can’t say that I love giving any tech giant my personal data, but Apple at least seems to care more about security than the other FAANG (MANGOS?) companies. On-device AI will always be more secure and less energy intensive than cloud computing, since the data is processed directly on your phone. (This is how current Apple Intelligence features like email summaries and AI emojis are generated.) But for the more complex tasks that Siri will confront, Apple pioneered private cloud compute (PCC), a way for devices to parse complex data over the cloud without even exposing your data to Apple itself. (If it’s possible to hack PCC, it hasn’t happened yet, even though Apple offers a $1 million bug bounty.)

In a recent conversation with the writer Calvin Kasulke — who is so internet-brained that he wrote a novel that takes place exclusively on Slack — I confessed what feels like a taboo desire to outsource all of my “life admin” to an AI.

“When you talk about the nonsense of the tech detritus in your life… I think the question is, ‘Is all that you have necessary?’ If it is necessary, isn’t it worth cultivating the skill and spending the time to do it?” Calvin told me. “I don’t think that those are skills that one should allow to atrophy.”

He makes a good point: Maybe instead of asking Siri to remind me about the TV show that my friend told me I should watch, I could pay more attention when I’m talking to my friends. I don’t want to get into the habit of forgetting more consequential details from my conversations.

“I’m sorry, but all of the commercials that are like, ‘What if I had the computer buy my kid a birthday gift?’ I’m like, ‘What if you learned what your kid likes?’ … Like, I don’t know man, it sounds like [they] don’t want to do the fundamental act of being a person,” he said.

Maybe when I say I want Siri to be like Emily from “The Devil Wears Prada,” I should remember that Emily’s character is on the verge of a crash-out. I know I can’t psychologically impact Siri like Miranda Priestly damaged Emily, but will I become the kind of person who can’t function without the friendly robot voice in my phone? Do I want to be that person?

At least if I decide to opt out from all of this, Apple will make that possible. Unlike Google’s controversial Search overhaul, the new AI Siri can be toggled on and off, so you don’t have to use it. Until then, I’ll have to decide if it’s worth it to taste the forbidden fruit of Siri AI.

Last year, Justin Ernest noticed a massive gap in how venture capital was working: Family offices and smaller institutional investors were eager to invest in the fastest-growing AI companies but couldn’t get access to those cap tables. 

Having spent over five years at Playground Global investing in deep tech and helping lead fundraising, Ernest was confident his connections to both investors and founders would allow him to bridge that gap.

Instead of launching a formal VC fund, a process he says takes new managers anywhere from 12 to 18 months, Ernest used his network to secure allocations of stock in high-profile, later-stage companies. He then offers these individual deals to a group of about 30 smaller institutional investors using special purpose vehicles (SPVs), single-asset funds, and nominee structures. In the latter, his firm, Sabertooth Capital, holds shares on behalf of participating investors rather than through a traditional SPV.

Over the last 12 months, Sabertooth has invested nearly $500 million into 10 companies, including Anthropic, Anduril, Base Power, Databricks, PsiQuantum, and SpaceX. The firm treats each deal as its own separate fund, in most cases structuring it as an SPV, in which the fund’s investors buy shares in the vehicle that owns the stock.

He’s writing checks ranging from $10 million to $275 million — meaning he’s gaining significant chunks of shares — and always participating in official, company-approved funding rounds.

Sabertooth is not the only firm offering family offices an opportunity to purchase equity in individual high-profile, late-stage startups. However, Ernest quickly raised a significant amount of cash from them because, in the sometimes-shady world of small allocations and SPVs targeting family offices, he’s earned a solid reputation.

“Justin is authentically an investor,” said Benjamin Wagner, a CIO for a family office managing the wealth of 50 individuals. “He has judgment, he has expertise, he’s very technical, that really distinguishes him from other organizations that tend to, in my opinion, just trying to aggregate capital.”

When Wagner tried to invest directly in PsiQuantum, the quantum computing startup last valued at $7 billion, the company’s CFO suggested that he invest through Sabertooth.

“So, the first time I met [Ernest], I knew he was legitimate,” Wagner said. “Justin’s access is definitely different from some of these fly-by-night organizations.”

That validation is extremely important. At a time when startups like Anthropic and Anduril are cracking down on unauthorized SPVs, investing through Sabertooth gives smaller limited partners some peace of mind. They know they are entrusting their money to an investor who is directly vetted and respected by the companies themselves.

Beyond technical knowledge, the Harvard Business School graduate honed his communication skills after largely overcoming a childhood speech impediment. Ernest credits his ability to secure allocations of stock when highly coveted tech companies are raising to his wide network.

“I’ve always found that my sort of superpower is being the nucleus of my network, and I like to use that and utilize that in a very strategic way,” he told TechCrunch.

For instance, he can generally obtain investor capital for a new SPV from family offices on a tight timeline.

“I have a captive set of LPs,” he said. “I can usually make four or five or six phone calls, and I know exactly what my LPs will commit.”

Ernest told TechCrunch that for now, he wants to continue growing his business of raising funds for specific companies on behalf of his dedicated LP base. However, his ultimate goal is to eventually raise a traditional venture fund. That’s a difficult task, but he believes Sabertooth’s strong returns via these one-off SPVs to prove his track record, something investors care about most when deciding to back a new fund.

He’s on his way with that wish. Sabertooth has already had one major big return from chipmaker Groq, which was licensed and acqui-hired by Nvidia for $20 billion late last year. Next up is SpaceX’s highly anticipated IPO this Friday, along with Anthropic’s expected public listing later this year. They are poised to deliver an even greater windfall for his investors.

But SPVs don’t have the same kind of street cred as traditional VC funds. Yet Ernest remains confident that starting with them, and earning a solid rep with family offices, rather than launching an emerging venture fund and duking it out with competitors was the right strategic move. “I wanted to be in the action,” he said. “I think this will end up being one of the best vintages of our lifetime.”

Updated to reflect Sabertooth’s total capital deployed.

Google just made its budget AI subscription plan a lot more budget-friendly, bringing a price war that’s been brewing in emerging markets squarely to American consumers.

The company announced Monday that it is cutting the monthly price of Google AI Plus from $7.99 to $4.99 — while doubling the storage included at that tier, from 200 gigabytes to 400 gigabytes.

Vikas Kansal, product lead for Gemini AI subscriptions, said on X that the storage updates would roll out to users over the next several days.

Google AI Plus launched in January as the most affordable paid AI subscription in the U.S. market, aimed at individual users and students rather than enterprise customers. The new pricing makes that positioning even more explicit.

It includes a decent feature set, too, including video generation via Omni Flash; the creative studio Google Flow; and NotebookLM, Google’s AI research assistant. Users who need more — more features, higher usage limits — can step up to Google’s AI Pro or AI Ultra tiers.

But the more interesting story here isn’t about Google’s product lineup. Subscription pricing hasn’t been a key battleground among AI providers in the U.S. until now — and that shift has serious consequences for the broader market, suggests Chi-Hua Chien, co-founder and managing partner at Goodwater Capital, a consumer-focused venture firm in the Bay Area.

Chien sees Monday’s announcement as the next salvo in what he calls the commoditization era for AI infrastructure, pointing to Google’s structural advantages — vertical integration, massive distribution, the ability to bundle — as precisely the kind of force that’s likely to erode margins for purer-play AI providers over time.

The historical parallel he reaches for is instructive. “If you look at the web era, the infrastructure companies were Microsoft, Cisco, Oracle, Northern Telecom, Lucent, Akamai, Equinix,” he told TechCrunch. “A lot of those companies survived for a period of time but aren’t worth a lot today.” The reason, he said, is that during every big tech shift — from PC to web to mobile — the infrastructure players get “commoditized very aggressively because the end customer doesn’t think, ‘Ooh, are my bits moving on Cisco networking equipment?’ They’re just thinking, ‘How do I move my bits as cheaply as possible?’”

None of this is a surprise to the people building foundation models. They’ve always known that raw AI capability would eventually become a commodity, and that the real competition would play out at the application and distribution layer. What Chien is saying is that “eventually” is now.

“My prediction for a lot of these infrastructure companies — and when I say infrastructure, I mean an OpenAI or an Anthropic, or the backend components, energy, chips, hosting — there will be a period of time when these companies are valuable,” he said. “But over time, you will see them get increasingly commoditized.”

It’s certainly something that a bigger pool of investors will be pondering soon. Both OpenAI and Anthropic have filed confidentially to go public, and their ability to command premium valuations may soon be tested by exactly the kind of price competition Chien is describing.

That competition has been building for nearly a year in markets like India, one of the fastest-growing AI user bases in the world. OpenAI drew first blood there in August of last year, launching ChatGPT Go at roughly $4.60 a month — a fraction of its standard $20 Plus plan. Google followed in December with a sub-$5 AI Plus plan of its own for Indian users.

Monday’s announcement suggests the same logic that drove those emerging-market moves — undercut, bundle, and capture users before rivals do — has now crossed over to the U.S. market.

Anthropic, notably, hasn’t followed. Unlike OpenAI and Google, it has yet to introduce localized pricing for India or a budget tier anywhere, a move that may become harder to avoid as its rivals keep slashing prices.