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Oliver Buchannon
Paul Smalera
The robot money is here

Mar 31, 2026

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8 min read

The robot money is here

Physical Intelligence is raising $1 billion at an $11 billion valuation — doubling in four months — as robotics AI becomes the next major capital destination. Meanwhile, legal AI platform Harvey closed $200 million at $11 billion, with Sequoia leading for the third time. The pattern: AI capital is migrating from foundation models to domain-specific applications with clear enterprise moats.

Paul Smalera
Paul Smalera
SpaceX is finally going public. Here's what it actually means.

Mar 27, 2026

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10 min read

SpaceX is finally going public. Here's what it actually means.

SpaceX is preparing to file its IPO prospectus this week or next — targeting a $1.75 trillion valuation and a $75B raise that would be the largest public offering in history. Meanwhile, Anthropic is eyeing a Q4 IPO of its own. And defense AI is having its own capital moment: Shield AI closed $2B at a $12.7B valuation. The IPO window is open.

Paul Smalera
Paul Smalera
The world's largest software buyer says the market is wrong about AI

Mar 26, 2026

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9 min read

The world's largest software buyer says the market is wrong about AI

Thoma Bravo — the world's largest software buyout firm — says the market has the AI-disruption story wrong. Software fundamentals are intact. The real divide is between easily-replaced point solutions and mission-critical, compliance-heavy systems that AI won't touch. They're buying. Private markets investors should pay attention.

Paul Smalera
Paul Smalera
 Musk just announced the biggest chip factory in history. Investors should pay attention.

Mar 24, 2026

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8 min read

Musk just announced the biggest chip factory in history. Investors should pay attention.

Elon Musk unveiled Terafab on Saturday — a $20-25B joint chip fab between Tesla, SpaceX, and xAI that targets a scale no private company has attempted in semiconductors. Meanwhile, the White House released its national AI policy framework pushing to preempt state AI laws, and Kalshi doubled its valuation to $22B in three months. A busy weekend for private markets.

Paul Smalera
Paul Smalera
OpenAI is eating the developer stack

Mar 20, 2026

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10 min read

OpenAI is eating the developer stack

OpenAI announced it will acquire Astral, the team behind Python's most-used developer tools, as part of an accelerating push to own the full software development lifecycle. Meanwhile, Microsoft is weighing legal action against OpenAI and Amazon over a $50B cloud deal it says violates its Azure exclusivity rights — a dispute that could reshape how Big Tech structures AI partnerships. And a new PitchBook analyst note asks the question no one in venture wants to answer: if SpaceX, OpenAI, and Anthropic all go public in 2026, is there enough capital left for anyone else?

Paul Smalera
Paul Smalera
When ”markets” and gambling mean the same thing

Mar 19, 2026

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9 min read

When ”markets” and gambling mean the same thing

Arizona filed the first-ever criminal charges against a prediction market company, accusing Kalshi of running an illegal gambling operation. Meanwhile, both Kalshi and rival Polymarket are in talks to raise at $20 billion valuations — roughly double where each sat just a few months ago. The collision of criminal exposure and record fundraising ambition tells you everything about where prediction markets are right now. Today's Deep Dive:

Paul Smalera
Paul Smalera
Jensen Huang just set the AI infrastructure agenda for the next two years

Mar 17, 2026

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7 min read

Jensen Huang just set the AI infrastructure agenda for the next two years

Nvidia kicked off GTC yesterday with Jensen Huang unveiling the Vera Rubin architecture and officially putting the Feynman GPU on the 2028 roadmap — the clearest view yet of how AI compute scales from here. Meanwhile, Meta is reportedly planning to cut 20% of its workforce as AI infrastructure costs balloon, and the Anthropic-Pentagon standoff continues to grind through the courts with no resolution in sight.

Paul Smalera
Paul Smalera
Vibe coding is the new AI infrastructure trade

Mar 13, 2026

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13 min read

Vibe coding is the new AI infrastructure trade

Cursor is reportedly in talks to raise billions at a valuation of up to $60 billion — more than doubling its $29.3B November 2025 mark. Lovable crossed $400M in ARR this week with just 146 employees. Replit raised $400M at $9B on a path to $1B ARR. In under 18 months, a category that barely existed has become one of the fastest-growing capital deployment patterns in private markets history. Meanwhile, Anthropic deepens its enterprise push via a potential Blackstone JV, and the Pentagon feud gets louder. Here's a bonus Friday Deep Dive about what this all means for private market investors.

Paul Smalera
Paul Smalera
The private market access trade is getting its first real stress test

Mar 12, 2026

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18 min read

The private market access trade is getting its first real stress test

Robinhood's new private markets fund raised $658 million and dropped 11% on day one. Fundrise had its own fund scheduled to list the same week — stronger portfolio, better fees — and quietly postponed. Two signals, one category. We dig into what the structure of these products gets right, what it gets wrong, and why the lockup these funds are trying to eliminate may actually be a feature. The Deep Dive:

Paul Smalera
Paul Smalera
Anthropic's $380B valuation has a new problem

Mar 10, 2026

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8 min read

Anthropic's $380B valuation has a new problem

Anthropic filed suit against the Pentagon over its "supply chain risk" designation — and the filing itself contains the most important number: the company's contracts are already being canceled, with hundreds of millions in revenue at risk. Meanwhile SoftBank's public stock is flashing warning signs about private AI valuations, and Nasdaq just announced the infrastructure that could eventually reshape how private securities trade.

Paul Smalera
Paul Smalera
 SpaceX is filing for its IPO. The window is officially open.

Mar 6, 2026

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9 min read

SpaceX is filing for its IPO. The window is officially open.

SpaceX is reportedly preparing to file confidential IPO papers with the SEC this month — targeting a valuation above $1.75 trillion and a June listing that could be the largest in history. Anduril is raising $4B at a $60B valuation as defense tech capital floods the market. OpenAI launched GPT-5.4 and hired IPO counsel, hitting $25B in annualized revenue. And Anthropic's Pentagon standoff is still live — the company is back in talks with the DoD even as the supply-chain risk designation stands.

Paul Smalera
Paul Smalera
The AI infrastructure boom has legs. Literally.

Mar 5, 2026

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12 min read

The AI infrastructure boom has legs. Literally.

Humanoid robotics is experiencing an AI-infrastructure-style capital surge — Neura Robotics raising ~€1B backed by Tether, Embo raising $100M+ for world models, and Arda raising $70M for manufacturing AI, all announced this week. Combined with Skild AI ($1.4B), Figure AI ($1B at $39B), and Apptronik ($935M at $5.3B) from recent months, investors have committed over $15 billion to humanoid and embodied AI startups since mid-2024. The question: is this the early innings of a trillion-dollar market, or the next overheated category? Let's Deep Dive and find out.

Paul Smalera
Paul Smalera
The fastest SaaS company ever just doubled again

Mar 3, 2026

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12 min read

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
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
Paul Smalera
Pulse: The $100 billion market nobody can measure

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
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
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
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
Paul Smalera
Friday the 13th came for the IPO market

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
Paul Smalera
 What a discount actually tells you

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
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
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
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
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
Paul Smalera
SpaceX and xAI in merger talks ahead of IPO

Jan 30, 2026

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8 min read

SpaceX and xAI in merger talks ahead of IPO

SpaceX and xAI are reportedly in merger talks ahead of SpaceX's planned IPO—a potential combination that could create the most valuable private company in history. Meanwhile, Waabi raised $1B and partnered with Uber to deploy 25,000+ robotaxis, PaleBlueDot AI hit unicorn status, and Northwood Space landed both $100M in funding and a $50M Space Force contract.

Paul Smalera
Paul Smalera
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