Hi {{first_name}}!
Things keep getting spicy in AI this week.
Anthropic's biggest customer just hired away their key talent, two companies simultaneously launched $200/month tiers, and Apple's considering outsourcing Siri. The drama continues, and the stakes keep getting higher.
As we continue to build at Context Ventures, we've launched Startup Intros with a simple mission: to help early-stage founders find the right investors, faster and smarter.
Before getting into the newsletter, you should check out our events this week:
🔥 Context VC & Startup Intros Events Coming Up
July 7: Live AdvancingVC Podcast Interview Series with Tim Hsia from Context VC:
10:30 AM: Amanda Robson, Founder of Modern Technical Fund, which recently closed a $22M debut fund. Sign up on Luma!
2:00 PM: Chris Douvos, Founder of Ahoy Capital, who is known for his unique LP perspective. Sign up on Luma!
3:30 PM: Jeff Clavier, the Founding Partner at Uncork Capital, one of the valley’s top seed-stage VCs. Sign up on Luma!
July 17: Caffeine & Capital: The next round of our morning coffee series. Come ready to get caffeinated and talk startups. Sign up on Luma!
Keep reading for the latest edition of the Trending Trending covering the past week:
🎯 BLUF: Bottom Line Upfront
Awkward for Anthropic: Its biggest customer just poached two star employees
Pricing Wars Escalate: Everyone's suddenly charging $200/month for premium AI features
Apple's Identity Crisis: Apple might finally admit Siri needs outside help to compete
VC Reality Check: VC alpha generation is getting harder, while wealthy clients avoid the asset class
Wealth Wars Lost: Private credit and real estate are winning the wealth wars against venture capital
🎭 On This Week's Episode of "As the Bay Turns"
Boris Cherny on “Mastering Claude Code in 30 minutes”
🔥 When Your Biggest Customer Becomes Your Biggest Threat
Anthropic just hit a mind-blowing $4B ARR (4x growth since January), but here's the plot twist: their biggest customer just hired away two of their star employees:
The Drama: Cursor, crushing it with $500M+ ARR and a $9.9B valuation, snagged Boris Cherny and Cat Wu, the brains behind Anthropic's competing Claude Code product.
The Awkwardness: Cursor relies on Claude to power their product, but now they're building competing features using the same AI while employing the people who built Anthropic's version.
The Numbers: Anthropic generates ~$333M monthly while burning $3B annually on AI infrastructure. Cursor doubled revenue growth since March and launched autonomous web/mobile agents.
AI development has gotten so competitive that companies are willing to risk key partnerships to get top talent. With Windsurf exiting to OpenAI for $3B, Cursor is staying in the ring to compete.
💰 The $200 AI* Club Just Got a Lot More Crowded
Remember when $20/month felt steep for software? When OpenAI introduced Pro at $200/month, it seemed really high. Now those days are officially dead.
The Pattern: AI pricing has three tiers: free (with painful limits), "SaaS-ish" $10-30 range, and "power user premium" at $200 for AI power users:
December 5, 2024 - ChatGPT Pro
April 9, 2025 - Claude Max: Includes Claude Code, integrations, advanced research, global web search, and priority access.
June 16, 2025 - Cursor Ultra: Backed by multi-year partnerships with OpenAI, Anthropic, Google, and xAI.
July 1, 2025 - Perplexity Max: Offers unlimited Labs, early Comet browser access, top-tier models, and priority support.
What started as OpenAI's expensive experiment has become the new industry standard in just seven months:
Autonomous Agents: These tools crossed a critical threshold. They're handling entire workflows autonomously, not just simple queries.
Use It or Lose It: Perfect time to use these models aggressively. You're getting way more value than you're paying for, especially with Claude Max.
The Strategy: Hook users with immense value to drive retention, then dial back features or hope compute efficiency improves profitability. Heavy users are getting an incredible deal that may not last.
🍎 Apple's AI Identity Crisis
Photo by omid armin on Unsplash
Apple finds itself admitting it needs help. The company that builds everything in-house is considering outsourcing Siri's brain to OpenAI or Anthropic.
Reality Check: Internal testing showed Claude and ChatGPT outperform Apple's models. Siri's 2025 upgrade flopped, leadership reshuffled after morale plummeted.
Brain Drain: Top AI talent jumps to Meta and OpenAI, who offer compensation packages Apple struggles to match.
The Stakes: Potentially putting Claude or ChatGPT in front of 2B+ iPhone users. Anthropic (valued at $61.5B) getting the nod over OpenAI ($300B) would be ultimate David vs. Goliath.
The Catch: Apple wants third-party models on their infrastructure for privacy. Anthropic demands multibillion-dollar annual fee.
If the company that built its reputation on controlling user experience hands Siri's brain to a third party, it's a clear sign AI is too big to get wrong, even if it means swallowing decades of pride.
🗳️ OpenAI vs Anthropic's Regulatory Showdown
Photo by Harold Mendoza on Unsplash
OpenAI and Anthropic were on opposite sides of a major regulatory battle. The US Senate killed a provision that would have banned states from regulating AI for 10 years.
The Provision: Sen. Ted Cruz's measure would have withheld federal broadband funding from states that regulated AI. VCs and AI CEOs lobbied heavily for it.
The Vote: Senators killed it 99-1 Tuesday morning, with Sen. Thom Tillis as lone dissenter.
The Split: OpenAI's Sam Altman supported the ban, arguing "regulatory patchwork" would slow progress. Anthropic's Dario Amodei opposed it, calling the moratorium "far too blunt" in a NYT op-ed.
The Stakes: This comes as New York passed a bill requiring AI companies to publish safety protocols, exactly what the provision would have prevented.
While OpenAI pushes for less regulation, Anthropic positions itself as the safety-conscious alternative and advocates for measured oversight. The AI industry's power struggles are spilling into DC.
📊 The Venture Capital Reality Check
Photo by Leo_Visions on Unsplash
📈 The Hunt for Alpha in VC Just Got Harder (And More Rewarding)
Level VC's new analysis reveals why generating alpha, those excess returns that separate great investors, has become both more challenging and more critical in venture capital.
Size Matters Less: Structural inefficiencies favor smaller, nimble funds over large ones as markets become more efficient
Expertise Beats Trends: Deep sector understanding beats following obvious trends in an increasingly crowded field
Network Effects Matter: Non-redundant sourcing networks matter as founder ecosystems shift rapidly
Speed Plus Smarts: Analytical edge combined with quick decision-making continues to provide advantages
While alpha generation has become tougher, the rewards are bigger than ever, as companies stay private longer and achieve larger valuations before going public.
💸 VC Loses the Wealth Wars Despite Creating Them
Fifteen years after AngelList democratized startup investing, wealthy individuals are avoiding the very asset class that taught them about private markets.
The Preference Gap: Only 26% of wealth advisers want VC allocations vs. 56% for private credit and 66% for private equity
Cash Flow Reality: Private credit and real estate offer actual cash flows and shorter time horizons that wealthy clients prefer over VC's decade-long wait times
Selection Risk High: Performance dispersion between top and bottom VC funds makes manager selection incredibly risky for advisers
The Liquidity Problem: With institutional LPs tapped out, VC desperately needs the $150T wealth channel, but first must solve its fundamental liquidity problem
The asset class that created modern wealth management is now losing to the alternatives it inspired.
💸 What Other Startups are Popping Off
Here’s a roundup of this week’s trending startup activity:
🚀 AI No-Code Dev Platforms
Bolt: Build your site or app today with AI - the go-to platform for rapid dev with intelligent automation
Pythagora 2.0: All-in-one AI dev platform that revolutionizes how you build software from concept to deployment
mysite.ai: AI that builds your website & gets leads, turning ideas into functional sites with built-in lead generation
Dyad: Free, local, open-source alternative to Lovable / v0 / Bolt for building sites with AI assistance
HeyBoss AI Boss Mode: Complete AI workforce that builds your website and runs your entire business
🤖 AI Agents & Systems
Cursor Agents: Browsers & Mobile: Work with a powerful coding assistant anywhere, bringing AI dev help
Portia AI: Secure AI agents with tools, auth, and smart control for enterprise-grade automation workflows
Handit.ai: The open-source engine that auto-improves your AI agents, making them smarter with every interaction
🎨 AI Productivity & Content Tools
Tabl 1.0: Multi-player web browser revolutionizing how teams collaborate and browse together in real-time
Lazy 2.0: One shortcut to capture & chat with your notes, everywhere you work and think
Pokecut: Use AI to create photos with just a few clicks or a prompt, democratizing professional images
Picsart Ignite 2.0: AI for Creators - instantly generate branded assets, ads, videos, fonts and more at scale
Jotform Presentation Agents: Create AI presentations that talk, listen and answer questions for interactive experiences
MyLens.ai: Visualize what matters in your content & ideas with AI-powered data visualization and insights
NativeMind: Completely private, open-source AI assistant that runs entirely on your device for ultimate privacy and control
Runbear: The perfect AI team member that integrates seamlessly into Slack and works like your best new hire
🛠️ Developer Tools & Infrastructure
Rybbit: The open-source Google Analytics replacement offering privacy-first web analytics for modern teams
FlashDocs API: AI-powered API that generates custom Slides and PowerPoint presentations automatically
Ops AI by Middleware: Intelligent observability copilot that resolves production issues before they become problems
Dynamic Mockups: Create realistic mockups at scale with automated design generation and API integration
Byterover: Memory layer for your AI coding agents, helping them remember context across dev sessions
Optibot: Agentic security-first code review with clear cues and no noise, streamlining dev workflows
📱 CRM & Relationship Management
Pally - AI Relationship Management: Intelligent connection manager that unifies all your social relationships
Twenty: The definitive open-source CRM that's redefining customer relationship management
Clarify: The autonomous CRM that helps you sell more by intelligently managing customer relationships
🎙️ Voice & Communication AI
Cekura: Lightning-fast platform for launching production-ready voice and chat AI agents in record time
AssemblyAI: Power voice agents with real-time speech API for next-generation audio applications
🌟 Editor's Note
At Startup Intros, our mission is to keep you informed and help you raise in the fast-paced world of Silicon Valley. Our free weekly newsletter delivers curated insights, deals, and trends to help you navigate the startup ecosystem.
Stay tuned for our upcoming paid daily newsletter and fundraising app to help you close your next round!
💭 Parting Thoughts
Silicon Valley's AI drama reveals an industry transforming from collaboration to cutthroat competition. Companies are willing to pay hundreds monthly for AI access, signaling we're witnessing the birth of truly indispensable AI tools.
Bottom line: The AI industry is getting expensive, getting everywhere, and getting powerful enough to justify premium pricing. Your move, traditional software.
Hit reply and let me know what you're seeing in your world.
Till next time,
Dev Chandra
CEO @ Startup Intros
Associate @ Context VC
LinkedIn: /in/devchandra
Tim Hsia
Investor @ Context VC
Co-Founder @ Startup Intros
LinkedIn: /in/timhsia
P.S. Raised this week, and we missed you? Want to be featured? Have tips or funding questions? Reply or DM us as we’re here to help.
Startup Intros Weekly Download: Your trusted source for founder-investor insights, delivered with clarity and focus.
