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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 6:56AM

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.

Chris Stokel-Walker

Bot bias

6/17/26

Companies are getting AI chatbots to smear their competitors

The race to influence AI chatbots is leading to some companies to adopt shady competitive tactics.

Tom Jones6/17/26

Prediction markets have, predictably, been given a boost by the summer of sports

Major platforms like Kalshi and Polymarket have seen huge upticks in users of late, thanks in no small part to what’s felt like a recent sporting smorgasbord, with major competitions across hockey, basketball, and soccer soaking up fans’ time (and spending, clearly) at the outset of summer.

While gaming industry groups may not like it, there’s been a huge change in the methods people are using to put money on the big games, with everyone from fortunate NYC bar owners, to a far less fortunate Spanish supporter, turning to prediction markets to try and turn their sports know-how into cold, hard cash.

According to a new report from Adam Blacker for apptopia, that shift might have been even more seismic than imagined in the wake of the NBA and NHL finals and around the 2026 World Cup kicking off.

2026 World Cup Reverses Seasonal Lull for Sports Betting Apps

According to a new report from Adam Blacker for apptopia, that shift might have been even more seismic than imagined in the wake of the NBA and NHL finals and around the 2026 World Cup kicking off.

South by Southwest Conference and Festivals

Gold Tesla Cybercabs are piling up, but they’re not picking up passengers yet

Low-volume production started in April. Now people are noticing them more and more in the wild.

Rani Molla6/15/26

Millie Giles

TAKING ACCOUNTS

6/15/26

Britain announces social media ban for under-16s starting early 2027

The UK government plans to use the same model for the restrictions as Australia — but how successful has that case study been so far?

UK Prime Minister Announces Under-16s Social Media Ban

Jon Keegan6/15/26

Anthropic pulls Fable and Mythos access worldwide after Trump administration bars their use by foreign nationals

Only days after releasing two versions of its next-gen AI model, Anthropic has disabled them for users worldwide.

Anthropic says it received a Friday night order from the Trump administration to suspend access to the models for any foreign national (anywhere in the world) — a group that included some Anthropic employees. In response, the company turned off access to everyone.

Last week, the company released to the public its much-anticipated Claude Fable 5 model (and its restricted version Claude Mythos 5, which is still being tested with trusted partners). Anthropic said in a blog post announcing the action that officials cited national security concerns with the new models, while offering few specific details.

The post said that the government gave the company “verbal evidence of a potential narrow, non-universal jailbreak” of the public Fable 5 model. A jailbreak is a means by which users can evade restrictions built into the code to unlock prohibited functionality. Anthropic downplayed the significance of the attack, and said other major models, such as OpenAI’s GPT-5.5, could also be affected by the technique described.

Fears of these first Mythos-class models being misused are running high, after Anthropic warned the cybersecurity world in May that the advanced cyber capabilities of Mythos have rapidly discovered thousands of vulnerabilities in ubiquitous software, leading to the decision to restrict the full version of the model to a close group of trusted partners for testing.

This morning, Axios reported that Anthropic technical staff have flown to Washington to meet with White House officials to resolve the issue.

The Wall Street Journal is reporting that the Trump administration’s decision to take action against Anthropic was prompted by discussions that Amazon CEO Andy Jassy had with officials, including Treasury Secretary Scott Bessent. According to the report, Amazon researchers said they had been able to evade some of Fable 5’s security restrictions using specific prompts. Amazon is a major investor in Anthropic.

Anthropic is currently suing the US government to fight the Pentagon’s blacklisting of the company on national security grounds.

Statement on the US government directive to suspend access to Fable 5 and Mythos 5