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Perplexity is in talks to raise again, as the battle for second in the AI chatbot race heats up

The latest funding round could peg Perplexity at a $14 billion valuation.

5/14/25 5:56AM

Like a lot of AI startups, Perplexity isn’t having a hard time finding new investors.

According to exclusive reporting by The Wall Street Journal, the company is in closing talks for a new $500 million funding round that would see it valued at a whopping $14 billion. For context on just how quickly valuations are still soaring in the AI sphere, Perplexity closed a funding round in November that saw its valuation reach $9 billion… which was already triple what the startup was worth just six months before that.

Though it’s certainly had its critics, the company’s eponymous AI search engine has proved popular since its release in late 2022, while plans to launch Comet — an AI-powered browser that could land as soon as this month — clearly have investors excited as well. In the ever-expanding universe of AI tools and chatbots, though, OpenAI’s star still shines brightest.

ChatGPT domination chart — Sherwood News

ChatGPT has been breaking its own traffic records every month of the year so far, hitting an almighty 780 million visits from American users in April, while web-based versions of other AI efforts have yet to build anywhere near as much steam. Indeed, discounting rivals from Big Tech giants like Meta’s new MetaAI platform or Google’s Gemini, ChatGPT really is a deus amid machinas, clocking over 8.5x more April site visits than the web versions of DeepSeek, Perplexity, Anthropic’s Claude, and Elon Musk’s Grok combined.

Among those chatbots and AI search engines not set up by Sam Altman or trillion-dollar tech companies, DeepSeek — the Chinese startup whose R1 model rocked AI stocks in January — leads the way, though it has lost momentum more recently.

AI platform visits chart — Sherwood News

Since DeepSeek burst onto the scene, causing a flurry of hurried explainers and inspiring a wave of online evangelists, tens of millions have flocked to sample the chatbot, reportedly built at a fraction of the cost of OpenAI’s flagship model. Still, monthly visit numbers are slipping from the February peak of 43 million.

Jon Keegan

Report: Microsoft adds Anthropic alongside OpenAI in Office 365, citing better performance

In a move that could test its fraught $13 billion partnership, Microsoft is moving away from relying solely on OpenAI to power its AI features in Office 365 and will now also include Anthropic’s Claude Sonnet 4 model, according to a report from The Information.

The move is a tectonic shift that boosts Anthropic’s standing, heightens risks for OpenAI, and has huge ramifications for the balance of power in the fast-moving AI field.

Per the report, Microsoft executives found that Anthropic’s AI outperformed OpenAI’s on tasks involving spreadsheets and generating PowerPoint slide decks, both crucial parts of Microsoft’s Office 365 productivity suite.

Microsoft will have to pay the competition to provide the services —Amazon Web Services currently hosts Anthropic’s models while Microsoft’s Azure cloud service does not, The Information reported.

OpenAI is also reportedly working on its own productivity suite of apps.

Microsoft to Buy AI From Anthropic in Partial Shift From OpenAI

The move is a tectonic shift that boosts Anthropic’s standing, heightens risks for OpenAI, and has huge ramifications for the balance of power in the fast-moving AI field.

OpenAI is also reportedly working on its own productivity suite of apps.

Jon Keegan

Apple announces extra slim iPhone Air, iPhone Pro with longer battery life, updated AirPods Pro 3 with live language translation, and refreshed Apple Watch line

At today’s “Awe Dropping” Apple event, the company announced its yearly refresh of the iPhone lineup. The new iPhone 17, iPhone 17 Pro, and iPhone 17 Pro Max were joined by a brand-new addition: the iPhone Air, a superthin model with tougher glass and faster processors.

Apple shares dipped on news of the product releases and are down about 1.4% on the day in afternoon trading.

The company also announced an updated Apple Watch line — Series 11, SE3, and Ultra 3 — with new features like 5G, high blood pressure detection, 24-hour battery life, and satellite communication.

Apple iPhone 17 — Apple’s iPhone 17 (Photo: Apple)

Here’s a breakdown of the new products Apple announced:

The ultrathin iPhone Air was described by Apple as “a paradox you have to hold to believe.” The sleek 5.6-millimeter-thin iPhone features a crack- and scratch-resistant front and back and “Macbook Pro levels of compute,” which you can pair with a weird $59 cross-body strap. It starts at $999.
The iPhone 17 has a faster A19 chip, an improved smart selfie camera, and a higher-resolution screen. It starts at $799.
The iPhone 17 Pro has a new design, ever-faster A19 Pro chip, a tougher “ceramic shield” on the front and back, better cameras, and a bigger battery that gets an extra 10 hours of video playback compared to its predecessor. It costs $100 more than the previous generation, but the minimum storage has doubled to 256 gigabytes. It starts at $1,099.
The iPhone 17 Pro Max starts at $1,199.
The AirPods Pro 3 have AI-powered live translation, a new heart rate sensor, eight hours of battery life, and improved active noise cancellation. The new AirPods can also track workouts, and Apple says they are built to fit more people’s ears with a new design and foam ear tips. They start at $249.
The Apple Watch Series 11 has 5G, a new high blood pressure detection feature, improved sleep tracking, a more scratch-resistant face, and 24 hours of battery life.
The entry-level Apple Watch SE 3 gets 5G, new health-tracking features, and an always-on display. It starts at $249.
The chunky Apple Watch Ultra 3 has an impressive 42-hour battery life, satellite communications for emergencies, and a brighter and bigger display. It starts at $799.

Rani Molla

10h

Tesla could sell a record number of vehicles in the US this quarter

That won’t be enough to keep full-year global sales from falling.

Guy waving an American flag in a tiny Tesla Cybertruck

Claire Yubin Oh & Jon Keegan

15h

Nebius soars after signing a 5-year deal with Microsoft to supply nearly $20 billion worth of AI computing power

Artificial intelligence infrastructure group Nebius jumped more than 50% in early trading on Tuesday after the company announced after the close on Monday a major deal to supply computing power for Microsoft’s AI operations.

Under the agreement, Nebius — which rose from the ashes of Russian tech giant Yandex — will provide Microsoft “access to dedicated GPU infrastructure capacity in tranches at its new data center in Vineland, New Jersey over a five-year term.” The New Jersey data center has a capacity of 300 megawatts. The total contract value through 2031 is $17.4 billion, though, if further capacity is required, the contract value could rise to $19.4 billion.

The deal represents a sizable portion of Microsoft’s proposed annual capital expenditure on AI, which is expected to reach $120 billion by the end of fiscal 2026.

Nebius and competitor CoreWeave are both on the short list of startups that Nvidia has invested in. Nvidia’s small stake in the former is now worth about $120 million.

Nebius announces multi-billion dollar agreement with Microsoft for AI infrastructure

The deal represents a sizable portion of Microsoft’s proposed annual capital expenditure on AI, which is expected to reach $120 billion by the end of fiscal 2026.

Nebius and competitor CoreWeave are both on the short list of startups that Nvidia has invested in. Nvidia’s small stake in the former is now worth about $120 million.

President Trump hosts tech executives and their guests to a dinner at the White House in the Oval Office.

Here are the Trump ties among the tech leaders who had dinner at the White House

Many of the attendees have donated to, vocally supported, or even worked for the president.

Jon Keegan9/8/25