👜 AI tool Perplexity goes shopping

In partnership with

Hi AI Futurists,

Perplexity AI is stepping into the next phase of chat-based commerce through a new partnership with PayPal, allowing users to shop, book travel, and buy tickets directly within its chat interface. Let’s take a look.

Here’s our agenda.

• Our Sponsor: Artisan

• Top AI news

• Perplexity goes shopping

• Top 3 selected AI tools

• AI in the wild

Best,
Lex

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Top AI news

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Perplexity 🤝 PayPal

With a new PayPal partnership, Perplexity AI is moving deeper into chat-driven commerce, letting users shop, book trips, and buy tickets directly in the interface. Payments will be processed seamlessly through PayPal and Venmo, with shipping, tracking, and support also handled by PayPal. The move marks a shift toward “agentic commerce,” where AI agents manage full transaction workflows. According to VP of Business Ryan Foutty, Perplexity’s goal is to be "wherever users are asking questions and making decisions" a vision that reflects the increasing integration of generative AI into everyday buying behavior. More here.

The announcement coincides with Perplexity’s ongoing funding push: it’s in late-stage talks to raise $500 million at a $14 billion valuation. That figure is lower than the original $18 billion target floated earlier this year, suggesting a recalibration of investor expectations as competition in AI search heats up. Accel is leading the round, which follows a rapid valuation climb from $3 billion to $9 billion just six months ago. Despite the adjustment, Perplexity remains one of the most closely watched players in the AI search market, going head-to-head with OpenAI, Google, and Microsoft. Details here.

The push into in-chat shopping puts Perplexity ahead of ChatGPT in commerce capabilities and shows how AI agents are being built not just to inform users, but to act for them. As Jack Forestell of Visa put it, these agents will be expected to “browse, select, purchase and manage on their behalf.” The trust infrastructure built by PayPal makes this vision plausible. For consumers, this signals less friction in everyday purchases. For businesses and creators, it raises new questions about where decision-making power and customer loyalty will reside.

Takeaways at a glance

• In-chat purchases are now possible via PayPal and Venmo within Perplexity search

• PayPal handles end-to-end transaction logistics

• Partnership launches as part of broader trend toward agentic AI

• Perplexity’s valuation climbs, despite coming in below initial $18B target

• Competing with OpenAI, Google, Anthropic in AI-enhanced search and commerce

What We Think About It:

• The most interesting shift here isn’t just tech, it’s behavior. If users adopt in-chat buying, it sets a precedent for how autonomous agents can operate commerce flows. That changes not only UI expectations but also backend architecture and trust models.

What You Can Do Right Now:

• Try out the new flow for yourself and see how in-chat shopping feels as a user within Perplexity. If you're working on anything in AI or product design, this is a good moment to study where the friction disappears and where the trust gaps still show up.

Get more done with these AI tools

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AI in the wild

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