Hi, I'm Kenneth. Welcome back to Tech Venture Navigator.
It's been a minute. The last two months have moved faster than any period since I started writing this newsletter. Three AI companies are preparing to go public in the same quarter at combined valuations approaching $4 trillion. GitHub's infrastructure physically broke under the weight of AI coding agents. PitchBook published data showing the per-seat SaaS model that built modern software is structurally cracking. Apple put Claude on every iPhone. And ChatGPT quietly crossed a billion monthly active users.
This edition catches you up on everything that matters. Let me get into it.
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I. The $1 Trillion IPO Wave: Anthropic, SpaceX, OpenAI
Goldman Sachs projects 2026 IPO proceeds could reach $160 billion. A quadrupling from 2025. Almost entirely driven by three companies.
Anthropic filed confidentially at a $965B post-money valuation, making it the most valuable private AI company in the world, surpassing OpenAI's $852B. The filing came after a $65B raise with a $36B private credit facility from Apollo and Blackstone. Combined capital: nearly $100B in a single transaction cycle.
SpaceX/xAI is targeting $2 trillion. xAI's Colossus supercomputer, the Grok model family, and a new federal government contract are all part of the combined entity. Pricing day was June 11.
OpenAI is expected to file its own S-1 "in coming weeks."
Three near-trillion-dollar AI IPOs in a single calendar quarter is unprecedented. Institutional investors have finite capacity to absorb this much new AI equity supply. If one prices above target, the others benefit. If one stumbles, the entire window could narrow.
Sources: Bloomberg | CNBC | Goldman Sachs
✈️ NAVIGATOR’S EDGE:
For LPs and investors: The capital absorption question is real. These three companies are competing for the same pool of institutional money. If you're allocating to AI in the next 12 months, understanding the sequencing matters more than any individual company's fundamentals. The winner of the IPO race sets the pricing benchmark for the other two.
For founders: If you're raising in the next two quarters, these IPOs will either unlock a wave of LP liquidity (if they go well) or freeze it (if they don't). Plan your timeline accordingly.
II. GitHub Buckled. 275 Million Commits a Week. Microsoft Called AWS for Help.
This is the infrastructure story that tells you where we actually are with AI adoption.
Microsoft confirmed on June 16 that it's routing GitHub traffic through Amazon Web Services. The reason: AI coding agents overwhelmed the platform's infrastructure. GitHub COO Kyle Daigle confirmed the platform was processing 275 million commits per week, on pace for 14 billion in 2026. In all of 2025, GitHub processed 1 billion total.
AI agent-opened pull requests grew from 4 million in September 2025 to 17 million by March 2026. GitHub logged nine service incidents in May. Availability dropped to roughly 88.4%, well below the 99.9% enterprise SLA.
Microsoft described the AWS arrangement as temporary while GitHub migrates fully to Azure by 2027.
Sources: Business Insider | TechTimes
✈️ NAVIGATOR’S EDGE: When the world's largest code platform has to call its biggest cloud competitor for help, that's not a failure story. That's a demand signal. 14 billion commits this year vs 1 billion last year. 14x growth. If you're building developer tools, infrastructure, or code review products, this is the TAM expansion event.Kenneth Kelly
III. The SaaS Seat Is Dead. PitchBook Says So With Data.
SaaS deal value hit a record $173B across 867 deals in Q1. Strip out OpenAI ($122B) and xAI ($20B), the remaining 865 deals still grew 27.5% quarter-over-quarter. The SaaS model isn't dying. It's being rewritten.
PitchBook's analyst note is the sharpest framing: enterprise software is converging with the $50 trillion global knowledge worker labour market. They call it "Service-as-Software." Vendors that pivot from selling tool access to selling completed work outcomes can capture a share of customer payroll budgets. The addressable market expands by orders of magnitude.
HubSpot moved Customer Agent to $0.50 per resolved conversation. Intercom's Fin crossed $100M ARR at $0.99 per resolution. Sierra hit $150M ARR on pure outcome pricing at a $10B valuation.
Meanwhile, public SaaS multiples compressed from 6.2x (end of 2024) to 4.9x (end of 2025) to 3.3x (end of Q1 2026). Roughly $1 trillion in SaaS market cap was erased in Q1 alone.
✈️ NAVIGATOR’S EDGE: The companies that survive own proprietary data and workflow context, not user seats. If your startup charges per seat, start modelling per-outcome pricing. If you're an investor, the "SaS J-Curve" (where declining seat revenue outpaces outcome revenue ramp) is the key risk to underwrite.Kenneth Kelly
IV. Apple WWDC: Claude is now an option on iPhone. Apple confirmed a $1B Gemini license deal on-balance-sheet. AI embedded across iOS, macOS, and all Apple services.
ChatGPT crossed 1 billion monthly active users. OpenAI running at $13B revenue against $34B spend. The $38.5B net loss in 2025 audited financials makes for fascinating IPO reading.
SoftBank committed €75B to France. Largest single AI infrastructure investment in Europe. 5GW of data centre capacity across three sites by 2031.
Anthropic proposed a global AI pause the same week it filed for a near-trillion-dollar IPO. The paper, "When AI Builds Itself," advocates coordinated slowdown on frontier development. The timing was noted.
Gemini 3.5 Pro still hasn't shipped publicly. Google CEO said "next month" at I/O on May 19. Polymarket odds concentrated on late June windows.
GitHub Copilot switched to token-based billing on June 1. No more flat subscriptions.
Japan's three largest banks confirmed access to Claude Mythos through Project Glasswing. First non-US financial institutions in the programme.
Global M&A hit $1.6 trillion in Q1 (new quarterly record, up 50.6% YoY). Software M&A at $287B including SpaceX/xAI. Google/Wiz ($32B), Palo Alto/CyberArk ($25B), Thoma Bravo/Dayforce ($12.3B), IBM/Confluent ($11B).
PitchBook: "The SaaS Seat Is Dead" - Enterprise software merging with the $50T labour market. Service-as-Software is the new model. The SaS J-Curve is the key risk for incumbents. (PitchBook)
PitchBook: Q1 2026 Infrastructure SaaS VC Trends - Deal value climbed 114% QoQ to $17.1B. Exit activity at six-year high: $40.5B. Databricks, Stripe, Rippling all in IPO pipeline. (PitchBook)
Anthropic: "When AI Builds Itself" - Proposes globally coordinated pause on frontier development. Published same week as IPO filing. Technically substantive regardless of what you think of the timing. (Anthropic Institute)
Perplexity CEO: Micron Will Be More Valuable Than Meta & Power is the Bottleneck to AI
Aravind Srinivas is the Founder and CEO of Perplexity, one of the fastest-growing AI companies in the world. Since the start of the year, Perplexity has tripled revenue to well over $500M in ARR. Aravind has raised over $1BN for the company with reported valuations reaching $20BN.
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Claude - Now on iPhone via WWDC. Glasswing expanding to Japanese banks. 1M+ daily signups.
GPT-5.5 - Agent runtime. "Give it a messy task, it finishes it."
DeepSeek V4 - Open-source, MIT licensed, 1M context, fraction of frontier pricing. Test V4-Flash for high-volume production workloads.
Lovable - Full-stack app generation via chat. The gold standard for non-technical founders shipping MVPs.
Bolt.new - In-browser development using WebContainers. Instant full-stack environment generation.
Averi - GEO. Get cited by Perplexity and ChatGPT.
Gamma - Research to presentation decks in 60 seconds.Lemlist — The outreach tool we recommend for breaking through the noise with personalised fundraising outreach.
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— Kenneth Kelly
Founder @Tech Venture Navigator
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