OpenAI and Oracle reportedly ink historic cloud computing deal

In this Newsletter Today:

• OpenAI and Oracle reportedly ink historic cloud computing deal

• Box CEO Aaron Levie on AI’s ‘era of context’

• Perplexity reportedly raised $200M at $20B valuation

• AI Tutorial

• 5 Best AI Tools

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OpenAI and Oracle reportedly ink historic cloud computing deal

OpenAI is reportedly entering a groundbreaking cloud computing agreement with Oracle. OpenAI will buy $300 billion in compute power from Oracle over five years, starting in 2027.

Key Points:

• Big scale: The total—$300 billion over five years—is one of the largest cloud computing contracts ever.

• Starts in 2027: The actual purchase of computing power begins in 2027.

• OpenAI is moving beyond Microsoft. This shows their shift away from relying solely on Microsoft Azure. They are also expanding their partnerships for infrastructure.

• Part of “Project Stargate”: This deal connects to the bigger “Stargate” initiative. It involves OpenAI, Oracle, and SoftBank. Their goal is to build large AI data centre infrastructure.

Why it matters:

• Such a massive commitment underlines how much compute power AI companies believe they will need in the coming years.

• It may reshape the balance of power among cloud providers—Oracle is stepping up as a major player in AI infrastructure.

• OpenAI expects big projects and high usage. This shows that AI development costs are rising fast.

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Box CEO Aaron Levie on AI’s ‘era of context’

Box has launched Box Automate. This new system adds AI agents to its cloud content workflows. Aaron Levie, CEO of Box, says the company helps organisations manage unstructured data, such as documents and marketing files. They use AI agents to make smart decisions, while ensuring there are guardrails to keep them on track.

Key Points:

• Why Box is pushing this now: Traditional automation works well with structured data, like databases. Most business workflows handle unstructured data, like documents, legal contracts, and marketing assets. These are messy and not clearly formatted. Box wants to automate those workflows using agents.

• What is Box Automate: It’s like an operating system for AI agents. We break workflows into segments and assign agents to them. For example: a submission agent, a review agent, etc. Each with its own scope. This helps manage complexity and avoid errors.

• The problem with “too much context”: Levie warns that more information isn’t always better. AI models have limited “context windows.” If you overload them, they get confused, lose focus, or make mistakes. So Box lets you define boundary points in workflows—when one agent stops, another begins. This keeps things more predictable and safe.

• Guardrails and trust: A core part of Box's strategy is to enforce access control, data permissions, and security. This helps ensure agents don’t access or share data that users shouldn’t see. It’s not just about what the AI can do, but what it should do reliably.

• Stance on model size vs. reliability: Box doesn’t commit to one kind of model (super large vs smaller reliable ones). The goal is to create an architecture that lets customers choose the level of agentic behaviour and complexity that suits them best. As models improve, Box’s system can adapt.

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Perplexity reportedly raised $200M at $20B valuation

Perplexity, the AI-search startup famous for its conversational answers and citations, has secured $200 million in its latest funding round. Now, it's valued at around $20 billion.

Key Points:

• Valuation jump: Just two months ago, Perplexity was valued around $18 billion. This new funding lifts the valuation to $20 billion.

• Revenue is growing quickly. Its annual recurring revenue (ARR) is almost $200 million, up from over $150 million.

• Total funding: Since its founding (~3 years ago), Perplexity has raised about $1.5 billion in total.

• Competition: Perplexity aims to challenge Google’s dominance in search. It focuses on its conversational search features.

• Bold moves: Recently, Perplexity grabbed attention by proposing to buy Google’s Chrome browser for $34.5 billion. This was partly driven by antitrust talks.

Why it matters:

• This is a strong signal that investors believe there’s room to disrupt traditional search engines. Perplexity is making a strong move in the AI search market. They have rising revenue, ambitious product launches like the Comet browser, and increasing user demand. This valuation shows that expectations are high. This applies not only to user growth but also to monetization, differentiation, and long-term impact.

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They’re a private company, but Pacaso just reserved the Nasdaq ticker “$PCSO.”

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