Jason

The proposed $60 billion Cursor/xAI-SpaceX tie-up is an IPO-contingent option, not a transaction closing today. SpaceX can acquire Cursor after going public or pay a $10 billion break clause; Jason Lemkin sees meaningful execution conditions, but Rory O’Driscoll thinks the public promotion signals intent to close. Industrially, Cursor brings several billion dollars of coding revenue but weak gross margins, while xAI brings Colossus, “hundreds of thousands of GPUs,” roughly $20 billion of infrastructure and little revenue — “a marriage made in heaven.”

SpaceX’s extraordinary multiple makes Cursor cheap even if $60 billion sounds unprecedented. At an alleged $2 trillion valuation, SpaceX would spend about 3% of its equity value to acquire perhaps 15%-20% of combined revenue; even at $1 trillion, Jason’s comparison is stock trading near 50X revenue buying Cursor near 10X year-end revenue. “If your stock is valued at 100 times revenues, you can buy things that are trading at 10 or 15 times revenue all fucking day long.”

The deal split the panel on whether $60 billion is an M&A high-water mark or merely the new floor for strategic urgency. Jason predicts a $100 billion acquisition within 12 months because seven roughly $2 trillion companies can spend 5% of market cap to avoid falling behind; Rory predicts this remains private M&A’s high-water mark for a decade, given the finite buyer pool and sub-10X revenue multiples elsewhere. They agree on the mechanism: every major CEO is asking, “Who the hell can we buy to get ahead?”, and Cursor has expanded the Overton window for $10 billion-$20 billion deals.

Anthropic’s trillion-dollar secondary price reflects peak scarcity and FOMO, not a settled judgment about the AI winner. Harry says European families want “Anthropic and nothing else,” but Jason notes Codex usage rose 50% in one month and argues the autonomous-agent war has only started: “I can’t honestly predict 30 days out.” Rory expects Anthropic to exploit the moment with an October/Q4 IPO, potentially raising at $1 trillion while accessing the equity, convertibles and debt needed for a stated $200 billion-$300 billion capital appetite.

Claude Design need not replace Figma, Adobe or Canva to impair their growth. Jason’s crucial distinction is that Anthropic built an application — with users, sharing, hierarchy and saved assets — rather than another prompt or purple-gradient artifact generator. It is not yet Figma or Illustrator, but its Claude Code integration lets product and engineering teams bypass slow design handoffs; over four, six or eight quarters, “if it maims you, it maims you.”

Tim Cook’s orderly exit masks a broader warning for pre-AI incumbents: paid retention can coexist with disappearing usage. Cook leaves Apple at 65 after market capitalization rose from roughly $350 billion to $4 trillion, with the stock barely reacting to internal successor John Ternus. Jason’s “stealth churn” test is more forward-looking: he still pays Netflix while watching YouTube, and he said Amelia had not used OpenAI for four months even though they were still paying for it — making MAUs, WAUs and DAUs growing faster than revenue a new survival indicator.

Rippling’s $1 billion ARR and 78% growth demolish “SaaS is dead,” but agents will reorder winners through APIs. The company reportedly accelerated from below $500 million only 11 months earlier, which Rory calls “a win against the run of play”; payroll remains deterministic, regulated infrastructure that customers will not vibe-code. Yet Jason may switch providers after six years on Brex in one week based solely on an agent/API bake-off: “Our AI VP of Finance… don’t care what the UX is.”

Salesforce’s headless strategy is really a bid to become the trusted control plane for enterprise agents. Its two-decade-old API can preserve the data and workflow layer as human seats disappear, but Jason sees the larger prize as “agent fabric”: real-time governance, security, context and auditability across hundreds of agents and sub-agents. Salesforce is well placed because CIOs trust incumbents, but execution must arrive before that advantage expires: “You can’t let these crazy agents run amok.”

🔗 Original source & video: Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead?

Anthropic’s $30B raise at $380B post (upsized from $10B) is “the only play in venture,” per Jason Lemkin — with public software down ~20% this year, every multi-stage fund needs its 0.01% just to show up in the one thing working. Rory O’Driscoll’s caveat: “in the short term momentum massively outperforms value,” and Anthropic’s last two 2025 rounds ($60B, then $160B) each roughly 2x’d, so nobody fights the tape.

The growth is genuinely unprecedented — and so is the fragility. Rory plowed through early Microsoft, Google and Compaq: “you’ve never seen a company grow 10x in GAAP revenue… year-on-year for 3 years… you’re leaning into the singularity here.” But those companies were wildly profitable; Anthropic is structurally closer to a semiconductor company, and Dario himself frames under- vs over-investing in compute as a bankruptcy-adjacent tightrope. At ~$4.5B GAAP revenue last year, maybe $15B this year, “30, 40 times GAAP revenue is a little pricey” once growth slows.

Anthropic went from 5% of OpenAI’s revenue to 64% in 14 months — “that is stealing budget.” Enterprise is deciding, not evaluating: Jason’s core call is that Corporate America will “will AI into existence” regardless of ROI — Klarna’s Sebastian went 6,000→3,000 employees and wants 2,000 — meaning 1-2 years of mega AI budgets on “the presumption of success,” then, per Rory, probable over-investment and retrenchment two-plus years out.

Public SaaS has entered the “dead zone”: the cohort is approaching 10% annualized growth, and if AI shaves another 30% off that, “it’s all just price increases and suing customers.” Jason can’t see a bottom because nobody wants more seats for humans “who complain and whine and quit every 3 months”; Rory’s rebuttal — “price clears all markets” — there’s a level where these compound at 12-15%, just not one holders will like.

Even the anointed aren’t safe: Figma IPO’d in July as “the best of the best,” then Replit and Lovable took ~$350M each in ARR from product-prototyping — revenue Jason says Figma should own outright (“Figma Make is a failure”). And Shopify — which all three call oversold — carries a real agentic-commerce bear case: Tobi has done more code commits in 60 days than in his history because the software “in 2 years may be obsolete.”

Stripe ($130-140B) vs Adyen ($40-50B): Rory buys Adyen — half Stripe’s revenue ($2B vs $5B), ~50% operating margins, 21% H2 growth, and public data you can actually value — while Jason takes Stripe for private-market flexibility. Both agree Adyen’s leadership “wildly miscommunicates” while Stripe tells a brilliant narrative. Rory’s prediction: Anthropic, OpenAI and SpaceX dive for the public line by year-end because capex-hungry companies have exhausted private capital.

OpenClaw’s sale to OpenAI (Harry guesses ~$100M, not the rumored $1B) marks “a freaking movement in AI”: a product designed to break guardrails that ignited developers, forced Anthropic into a cease-and-desist it may regret, and made autonomous 24/7 agents inevitable — “the horse has left the stables.” Downstream trades: agent-first security products, and inference managed via Haiku 4.5 at ~1/20th the cost of Opus 4.6.

Monday at ~$3.5B (down 51.3% YTD, $1.25B revenue growing 27%, ~$1B cash) is “the greatest buy of the value stocks” — if you still believe the December durability thesis. The tell that conviction is gone: Jason planned to buy $200K of four beaten-down names for the show, Shopify first — it crushed earnings, the stock didn’t move, and he couldn’t pull the trigger: “I couldn’t see the floor.” A live four-stock, $200K bet is now on for a coming episode.

🔗 Original source & video: Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued?

Benchmark’s latest partner loss says more about the leverage of elite individual investors than about Benchmark’s durability. Harry called it stunning that someone can hold “one of the top gigs in venture” and still decide it is not enough; Jason warned that Benchmark’s brand remains “freaking powerful,” while Harry argued Victor’s relationships, multistage appetite and ability to retain 100% of the carry make independence rational.

LPs are financing exceptions to long-standing rules on small funds, team cohesion, board service and stage discipline when an exceptional investor asks them to. Jason’s hedge matters: some discarded rules are obsolete, but others may reveal their wisdom in the next downturn. Elad Gil embodies the override: access to category leaders, the ability to pick from pre-seed through late stage and a 10-to-15-year record let him effectively say, “Thank you for your advice. Now, thank you for your money.”

Fast deployment creates immediate relevance, but only correct deployment sustains it. More checks bring more deal flow and markups; bad selection merely produces “relevance in the short term and failure in the long term,” as Tiger and SoftBank demonstrated. The more durable model combines elite early-stage access with huge follow-ons—the playbook Rory sees at Thrive, Greenoaks, Founders Fund and Elad Gil.

Anthropic’s valuation reset from $100 billion toward $150 billion–$180 billion reflects apparent revenue reacceleration and extraordinary developer demand. The discussed trajectory was roughly $1 billion late last year to $4 billion this year, leaving a “brutal” two-horse race with OpenAI. Jason’s central call is that top developers could consume $8,000–$10,000 monthly—not $200—because agents can work in parallel around the clock.

Google is the panel’s best-executing hyperscaler, while Microsoft’s loss of developer-tool leadership is the clearest incumbent failure. Jason’s provisional trade was buy Google and short Amazon: Google Cloud is smaller but fastest-growing, while AWS appears the hyperscaler laggard. Microsoft began with GitHub Copilot yet let Cursor reach roughly $900 million against Copilot’s cited $500 million.

There is still no visible break in AI infrastructure demand, but capex is running much faster than monetization and eventually must clear the income statement. The panel contrasted roughly $600 billion of investment with a $30 billion growing revenue line and noted that the chips will eventually be depreciated; Jason conceded that shorting the thesis early would have taken Nvidia from $100 to $170 against you. “The market can stay irrational longer than you can stay solvent.”

The trillion-dollar incumbents are rich, but the panel sees them as being on the back foot rather than too powerful in AI. Google has a working model; Apple “doesn’t even have a product that works”; Microsoft bought access it does not fully own; and Meta is spending from a “terrible psychological need for a product.” Apple’s hardware and App Store toll may protect it, but Harry—despite Apple being his largest position—said five years without growth should force a board-level management question.

The closing forecasts favored Cursor above $4 billion and Lovable above $400 million by end-2026, while OpenAI at $800 billion split the panel. Harry leaned under; Jason argued over on GPT-5, Codex and a first Jony Ive product. Jason also argued that if OpenAI needs $800 billion, deeply committed investors and sovereign capital will “solve for it.” AI capex already equals about 1.2% of GDP, above the cited 1.1% bandwidth peak but far below the railroad boom’s 6%—enough room for further spending, but also for a painful reset.

🔗 Original source & video: Why Apple Needs a Management Overhaul & Why Google is Catching Up with Hyperscalers