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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.

Figure’s robots just sorted packages for 200 hours straight

What started as a 10-hour human-versus-robot challenge turned into a continuous marathon shift spanning nine days of continuous work.

Jon Keegan5/22/26

Rani Molla5/22/26

Report: Uber considers full Delivery Hero takeover to take on DoorDash outside the US

Uber appears to be considering upping its competition with DoorDash outside the US, exploring a potential full takeover of Frankfurt-listed Delivery Hero, Bloomberg reports. Earlier this week the US-based ride-hailing service disclosed a 19.5% stake in the food delivery company, but now that could go higher.

The $11.8 billion German company could be particularly vulnerable to a takeover right now, with its CEO having recently stepped down following pressure from activist investors to sell off assets. A full acquisition would give Uber a massive foothold in over 60 countries to combat DoorDash’s European-focused Wolt unit.

Uber has been involved in a lot of deal-making of late, mostly in the autonomous vehicle space, where it now has more than 30 partnerships globally.

Uber extended its losses on the news and is currently down around 1.7%.

Uber Said to Study Full Takeover of European Rival Delivery Hero

Uber has been involved in a lot of deal-making of late, mostly in the autonomous vehicle space, where it now has more than 30 partnerships globally.

Uber extended its losses on the news and is currently down around 1.7%.

Rani Molla5/22/26

Meta released a Reddit dupe. Reddit investors don’t like it.

Fresh on the heels of releasing a Snapchat dupe, which sent Snap down earlier this month, Meta seems to be meddling with Reddit, quietly releasing a Reddit-like Facebook app called Forum yesterday. After news of the “dedicated space built for deeper discussions, real answers and the communities you care about,” Reddit’s stock is down 4.5% today.

Last month, Reddit’s earnings report handily beat analysts’ expectations, but it continues to struggle with the perception that bigger tech companies — including Meta — investing heavily in AI will eat its lunch. The stock is down nearly 40% year-to-date.

Jon Keegan5/21/26

Report: OpenAI’s Q1 revenue was $5.7 billion, beating Anthropic

The neck-and-neck race between OpenAI and Anthropic as the AI companies barrel toward their expected IPOs this year is shaking out some internal numbers for would-be investors to ponder.

The Information is reporting that OpenAI’s first-quarter revenue was ~$5.7 billion, about $1 billion ahead of Anthropic’s revenue for the same period.

The Wall Street Journal recently reported that Anthropic is on course to more than double its first-quarter revenue of $4.8 billion to $10.9 billion in the second quarter. It is not known what OpenAI is projecting for Q2.

Recently, The New York Times reported that Anthropic’s current fundraising round seeking to raise between $30 billion and $50 billion comes with a valuation of up to $950 billion, putting it ahead of OpenAI’s latest reported valuation of $850 billion.

OpenAI Held $1 Billion Revenue Lead Over Anthropic in First Quarter

Rani Molla5/21/26

Alphabet’s Waymos are still getting caught in floods after recall

Waymo, the self-driving subsidiary of Alphabet, has paused operations in Atlanta after a new report of a vehicle driving into a flooded roadway and getting stuck, TechCrunch reports. The news comes just weeks after the company recalled its fleet of nearly 4,000 driverless cars to deal with a previous flood incident in San Antonio, where the service is also paused.

After that incident, Waymo instituted an “interim remedy” to make the vehicles “exclude additional operating conditions that present an elevated risk of encountering a flooded, higherspeed roadway,” but added that it was still “developing the final remedy for this recall.”

As we’ve noted, Waymo has mostly kept its rollout — now public in 11 cities — to more temperate climates, as severe weather poses more challenges to autonomous vehicles.

Waymo pauses Atlanta service as its robotaxis keep driving into floods | TechCrunch