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The fastest SaaS company ever just doubled again

Cursor's revenue doubled to $2B ARR in just three months — the kind of trajectory that rewrites venture math. Reflection AI is reportedly seeking $2B+ at a $20B valuation just five months after its last raise. Meanwhile, Musk is cleaning house: X and xAI plan to repay $17.5B in debt ahead of a potential SpaceX IPO. And MongoDB's 24% post-earnings plunge is the latest signal that even strong growth can't save you when forward guidance disappoints.

Paul Smalera

Block just cut half its workforce. Wall Street loved it.

Feb 27, 2026

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14 min read

Block just cut half its workforce. Wall Street loved it.

Block laid off 4,000 employees—nearly half its workforce—and the stock surged 24%. CEO Jack Dorsey called it a shift toward becoming "intelligence-native." Meanwhile, OpenAI told investors it's targeting $280B in revenue by 2030, Nvidia's best quarter ever wasn't enough for Wall Street, and the week's biggest funding rounds signal capital is flowing away from software and toward the physical world.

Paul Smalera

Feb 26, 2026

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10 min read

Pulse: The $100 billion market nobody can measure

PitchBook's annual secondary market report is out, and the headline number is staggering: U.S. venture secondaries hit an estimated $106.3 billion in 2025 — rapidly closing in on the scale of IPOs and acquisitions. But perhaps the most interesting finding is the one that says the most about where this market actually stands: the margin of error on that estimate is $58 billion. Meanwhile, Stripe just repriced at $159B in a tender offer yesterday, and Wall Street keeps buying its way deeper into secondaries. Time for the Deep Dive.

Paul Smalera

Pulse: A Substack post helped tank the Dow 800 points. Here's why it matters for private markets.

Feb 24, 2026

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9 min read

Pulse: A Substack post helped tank the Dow 800 points. Here's why it matters for private markets.

A 7,000-word thought experiment from a Substack newsletter helped fuel an 800-point Dow selloff Monday, crystallizing Wall Street's deepening anxiety about AI disruption. And as of midnight, a new 10% global tariff took effect—creating fresh uncertainty for the 2026 IPO pipeline.

Paul Smalera

The $1 trillion question hanging over private markets

Feb 20, 2026

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12 min read

The $1 trillion question hanging over private markets

Blue Owl's decision to permanently halt redemptions in a retail private credit fund sent shockwaves through alternative asset managers this week. Meanwhile, Nvidia is reportedly finalizing a $30B equity investment in OpenAI, Fei-Fei Li's World Labs raised $1B for spatial AI, and Robinhood is betting that retail investors want exposure to pre-IPO companies.

Paul Smalera

Wall Street just bought the private markets. Here's what that means for you.

Feb 19, 2026

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10 min read

Wall Street just bought the private markets. Here's what that means for you.

Two of the largest independent secondary marketplaces — Forge and EquityZen — are becoming units of Schwab and Morgan Stanley. For individual accredited investors, the structural implications run deeper than the headlines suggest. Here's what's actually changing, and what to watch next. Welcome to the Deep Dive.

Paul Smalera

Feb 13, 2026

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10 min read

Friday the 13th came for the IPO market

The IPO market had a rough week — Clear Street fully suspended its offering after slashing it by 65% and still failing to generate enough investor demand. The software selloff is freezing deal activity, and PitchBook says more than a quarter of unicorns may no longer deserve the title. Meanwhile, Anthropic closed yet another mega-round ($30B at $380B), and asset management consolidation accelerated with Nuveen's surprise $13.5B acquisition of Schroders.

Paul Smalera

Feb 12, 2026

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11 min read

What a discount actually tells you

When secondary shares trade below a company's last fundraise, the instinct is "bargain." But discounts aren't coupons — they're signals. Today we break down a framework for reading what the secondary market is actually saying. Plus: humanoid robots raise almost $1B, a Twilio co-founder bets on fusion, and more. Here's our Thursday Deep Dive:

Paul Smalera

The AI business model war just went live on national television

Feb 10, 2026

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12 min read

The AI business model war just went live on national television

OpenAI officially launched ads inside ChatGPT — hours after Anthropic roasted the idea during the Super Bowl. Meanwhile, Databricks closed $7B in financing at $134B, Stripe is eyeing a $140B tender offer, and Harvey AI is reportedly raising at $11B just weeks after closing at $8B. Plus: Byrne Hobart on why Benchmark is quietly raising SPVs, and Tomasz Tunguz on what software stock declines actually tell us about the AI threat.

Paul Smalera

The $285B wakeup call—and the $100B+ bet on what comes next

Feb 6, 2026

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10 min read

The $285B wakeup call—and the $100B+ bet on what comes next

Anthropic's open-source legal plugins triggered the largest software selloff since the tariff shock—wiping out $285 billion in market cap from a batch of markdown files on GitHub. Meanwhile, NFX argues AI gaming's technology window just cracked open, Cerebras raised $1B at a $23B valuation and over $2B in fresh funding landed across inference chips, voice AI, autonomous SREs, and construction robotics. The message from capital markets this week: AI infrastructure is the trade, and incumbent software is the short.

Paul Smalera

From $68B to $11B: Figma's lesson for private investors

Feb 5, 2026

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11 min read

From $68B to $11B: Figma's lesson for private investors

Figma peaked at a $68 billion market cap days after its July IPO—a 250% first-day pop that marked the largest gain for a billion-dollar IPO in three decades. Seven months later, it trades at roughly $11 billion, down 84% from that high. The fundamentals? Still strong: 38% revenue growth, 131% net retention. For private market investors, this is a real-time lesson in how AI narrative risk can compress valuations faster than business performance changes. Here's our Thursday Deep Dive:

Paul Smalera

Musk just created a $1.25 trillion company

Feb 3, 2026

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8 min read

Musk just created a $1.25 trillion company

SpaceX acquired xAI yesterday in a deal that creates the world's most valuable private company at $1.25 trillion—and reshapes what investors will be buying in the coming IPO. Waymo closed its own mega-round at $16 billion and a $126 billion valuation. And Nvidia's Jensen Huang says his OpenAI investment will be "huge"—but not $100 billion.

Paul Smalera

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The fastest SaaS company ever just doubled again

Block just cut half its workforce. Wall Street loved it.

Pulse: The $100 billion market nobody can measure

Pulse: A Substack post helped tank the Dow 800 points. Here's why it matters for private markets.

The $1 trillion question hanging over private markets

Wall Street just bought the private markets. Here's what that means for you.

Friday the 13th came for the IPO market

What a discount actually tells you

The AI business model war just went live on national television

The $285B wakeup call—and the $100B+ bet on what comes next

From $68B to $11B: Figma's lesson for private investors

Musk just created a $1.25 trillion company

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