1. Menlo Ventures Just Cashed In a $500M Bet Nobody Else Wanted to Make

Menlo Ventures raised $3 billion in new capital, the largest fundraise in the firm’s 50-year history, after its early investment in Anthropic, now worth nearly $14 billion as Anthropic’s valuation climbed past $900 billion. Menlo led Anthropic’s Series D in 2024 by structuring roughly $500 million of that round as a special purpose vehicle, at a time when no major firm was writing three-quarter-billion-dollar checks. AI Funding TrackerTech Funding News

Spence’s take: Everyone calls these bets “contrarian” after they pay off. The actual contrarian move happened in 2024, when nobody knew if it would work.

2. XCures Doubled Its Valuation Cleaning Up Medical Records With AI

XCures landed a $46 million Series B led by Innovius Capital, bringing total funding to more than $76 million and valuing the company at $127 million post-money, more than double its prior round. The company grew from roughly $3 million to $10 million in annualized recurring revenue in 2025 and is on track to break $20 million in 2026, while achieving cash-flow breakeven last year. Calcali Tech

Spence’s take: A profitable company intentionally entering a burn phase to grow faster is one of the most underrated signals in venture. It means the founders chose growth, not the other way around.

3. Healthcare AI Just Crossed an $8.5 Billion Threshold This Year Alone

Investors have put an estimated $8.5 billion into seed- to growth-stage funding for AI-powered health tech companies in 2026 as of late June. Calcali Tech

Spence’s take: Healthcare moves slower than every other sector until it doesn’t. This number says we’re past the “if” stage and into the “how fast” stage.

4. Twenty’s $1B Cyber Warfare Bet Is Still the Story Nobody’s Fully Priced In

Twenty, the Arlington-based offensive cyber startup for the U.S. military, became America’s first venture-backed cyber warfare unicorn earlier this month after raising a $100 million Series B at a $1 billion valuation, less than two years after founding.

Spence’s take: A billion-dollar valuation with no disclosed revenue isn’t proof of a great company. It’s proof that investors believe the category just became fundable. Those are very different things.

5. Menlo’s Anthology Fund Shows the New VC Playbook: Be the Insider, Not Just the Investor

Menlo launched a $100 million fund called Anthology in partnership with Anthropic, which has since grown to roughly $250 million deployed, backed more than 60 companies, and produced exits including Graphite (acquired by Cursor) and Astrix Security (acquired by Cisco). Tech Funding News

Spence’s take: The smartest funds aren’t just writing checks anymore. They’re building proprietary pipelines into the company they bet the firm on. That’s a moat most LPs don’t fully appreciate yet.

Why Menlo Is the One to Watch

I want to run this through asymmetric bets, a model I cover in my book, Mental Models: How to Think, Act, and Win. Menlo’s 2024 Anthropic investment had a defined downside: the capital they put in. The upside, if Anthropic became one of the most valuable private companies in the world, was essentially unbounded. That’s the entire logic of venture capital distilled into one decision. Most investors talk about asymmetric bets. Menlo actually structured a $500 million SPV around one, at a moment when the broader market had gone quiet on big checks. The lesson isn’t “go invest in AI labs.” It’s that real conviction shows up as structuring your bet correctly when consensus is against you, not just picking the right company.

——————————————————————————————————————

If this was useful, share it with someone who builds things. And if you want the full toolkit of 50 mental models, you can grab my book, Mental Models: How to Think, Act, and Win, right now.

Get it Here

——————————————————————————————————————

Next week’s deep-dive:

——————————————————————————————————————

1. Odyssey Just Raised $310M to Teach AI How the Physical World Actually Works

Odyssey, a world model AI startup founded by self-driving vehicle veterans Oliver Cameron and Jeff Hawke, raised a $310 million Series B at a $1.45 billion valuation, led by Natural Capital with Amazon, AMD Ventures, GV, and others participating. Instead of predicting the next word in a sentence, the company’s models learn to predict how the physical world behaves, including how objects move and what happens after something is touched or pushed. Odyssey’s CEO says the field is approaching the “GPT-3 moment” for world models, the point where the technology shifts from promising research into a breakthrough foundational layer.

Spence’s take: Everyone’s been racing to make AI talk better. This round is a bet that the next unlock is making AI understand physics better. Different race, same stakes.

2. SiFive’s $400M Says the Chip Wars Aren’t Just an Nvidia Story

Semiconductor startup SiFive raised a $400 million Series G round led by Atreides Management, challenging incumbent Arm Holdings with chip designs built on an open rather than proprietary standard.

Spence’s take: Open standards versus proprietary lock-in is one of the oldest fights in tech. SiFive just got $400 million more ammunition to fight it in chips.

3. Capital Is Concentrating Around Problems Nobody Can Commoditize

This week’s funding tape shows investors concentrating capital around a narrow set of hard-to-commoditize problems: sovereign cyber defense, enterprise workflow automation with measurable ROI, custom silicon design, and infrastructure sitting close to the AI compute bottleneck. Deals like Dream’s $260 million round, Gradial’s $65 million Series C, and Architect Labs’ $24 million seed all point to the same investor instinct: back teams attacking expensive, mission-critical systems where incumbents are slow to adapt.

Spence’s take: When investors stop chasing novelty and start chasing bottlenecks, that’s usually a sign the easy money phase of a cycle is ending.

4. Odyssey’s Amazon Deal Is the Real Story Buried in the Headline

Alongside the funding, AWS became Odyssey’s preferred cloud provider, with the startup committing to optimize its models for Amazon’s Trainium AI chips, positioning them as an alternative to Nvidia’s hardware.

Spence’s take: Funding rounds get headlines. Cloud and chip commitments get ignored. This one’s worth watching, because it’s Amazon picking a side in the AI infrastructure fight before most people noticed there was a fight.

5. The Smartest Money in the Room Showed Up as Individual Investors, Not Funds

Odyssey’s investor list includes existing backers like Jeff Dean, Google’s chief scientist, Elad Gil, Qasar Younis, co-founder and CEO of Applied Intuition, Garry Tan, president and CEO of Y Combinator, Guillermo Rauch, founder and CEO of Vercel, and Kyle Vogt, founder of Cruise.

Spence’s take: When the people building competing AI companies personally write checks into a rival, that’s not just a vote of confidence. That’s insiders hedging their own thesis.

Why Odyssey Is the One to Watch

I want to run this through second-order thinking, a model I cover in my book, Mental Models: How to Think, Act, and Win. The first-order story is “AI startup raises $310 million.” The second-order story is what happens if world models actually work: robotics, gaming, autonomous systems, and scientific simulation all get access to AI that understands cause and effect in the physical world, not just language patterns. That’s a bigger shift than a better chatbot. It’s AI gaining a working model of reality itself, and the company that gets there first doesn’t just win a product category. It potentially becomes the infrastructure layer everyone else builds on top of.

——————————————————————————————————————

If this was useful, share it with someone who builds things. And if you want the full toolkit of 50 mental models, you can grab my book, Mental Models: How to Think, Act, and Win, right now.

Get it Here

——————————————————————————————————————

Next week’s deep-dive:

——————————————————————————————————————

1. Bezos Bets $12B That AI Can Replace the Slowest Part of Engineering

Prometheus raised $12 billion in a Series B from JPMorgan Chase, Goldman Sachs, BlackRock, and Bezos himself, pushing total funding past $18 billion after launching just seven months ago. That puts the company’s valuation at roughly $41 billion, placing it among the top five most valuable AI startups on the planet. The 150-person company is building an “artificial general engineer” designed to compress the design-to-manufacturing cycle for physical products from years down to months.

Spence’s take: Seven months, $18 billion, zero disclosed revenue. This is either the smartest bet in physical AI or the most expensive science project in history. There’s no third option.

2. Robinhood’s Prediction Markets Playbook Just Got a $1.4B Validation in Germany

NEURA Robotics, a German physical AI robotics company, raised up to $1.4 billion in Series C funding led by Tether, alongside Qualcomm, Amazon, and NVIDIA, marking the largest round ever for a full-stack robotics company.

Spence’s take: When crypto-native capital and chip giants write the same check, that’s not hype. That’s two completely different risk appetites agreeing on the same thesis.

3. The Gaming Industry Just Bought a Piece of Its Own Plumbing

Interchecks, an instant payments platform serving sportsbooks and fintechs, raised $50 million in a Series C led by Bettor Capital, a growth fund focused entirely on real-money online gaming, with Commerce Ventures, Decades Holdings, and Thayer Street Partners also joining. The company has processed more than $50 billion in transactions over a decade, with triple-digit revenue growth for seven straight years and profitability since 2023.

Spence’s take: A profitable, decade-old company raising venture money on its own terms is rarer than the unicorn headlines. Pay attention when boring and profitable decide to raise anyway.

4. Voice AI Is Crowded, But Investors Still See Room for a Winner

Bland closed a $50 million Series C led by Dell Technologies Capital, with HubSpot Ventures and others joining. The company says it handles more than 3.5 million calls per week and has processed over 175 million AI phone calls total.

Spence’s take: Crowded markets don’t scare good investors. They just raise the bar for who gets funded next.

5. Wall Street’s Biggest Names Just Quietly Bet on Tokenized Assets

Receipts Depositary Corporation announced a $7 million oversubscribed round led by LiveOak Ventures, with Hivemind Capital, OTC Markets Group, and GTS also participating, to issue depositary receipts on digital and alternative assets.

Spence’s take: Small check, big signal. Traditional market infrastructure players are building the plumbing for tokenized assets before retail even notices. This is the kind of deal that looks irrelevant until it isn’t.

Why Prometheus Is the One to Watch

I want to run the Prometheus deal through second-order thinking, one of the models in my book. The first-order story is “AI startup raises a lot of money.” The second-order story is what happens if this actually works: entire categories of physical engineering jobs get compressed into a software workflow, and the bottleneck for inventing new jet engines, drug compounds, or hardware shifts from human design cycles to compute and data access. That’s not an incremental shift. That’s a complete rewrite of who controls the pace of physical innovation, and right now Bezos and a handful of banks are betting $41 billion that they’ll own that rewrite.

If this was useful, share it with someone who builds things. And if you want the full toolkit of 50 mental models, my book is out now.

Get it Here

Next week’s deep-dive:

Five rounds closed this week. Add them up and you get roughly $89 billion moving in a handful of days. That’s not noise. That’s a market telling you exactly what it wants, if you bother to read the tape instead of the headlines.

Here are the five that actually matter, and the one signal sitting underneath all of them.

1. SpaceX priced the largest IPO in history

SpaceX priced its IPO Thursday night at $135 a share and debuts on Nasdaq today under the ticker SPCX. The raise: about $75 billion across roughly 555.6 million shares, valuing the company near $1.77 trillion. For scale, the prior record holder, Saudi Aramco, raised $29.4 billion back in 2019. This deal is more than 2.5 times bigger. Musk keeps north of 82% voting control. Reported 2025 revenue was $18.7 billion, up 33% year over year, against a net loss near $4.9 billion.

Spence’s take: A rocket company is going public, but the asset doing the heavy lifting is Starlink’s recurring revenue. The hardware gets the headlines. The subscriptions pay the bills.

2. Bezos raised $12 billion for a startup that’s seven months old

Prometheus, the industrial AI company where Jeff Bezos is co-CEO, announced a $12 billion Series B at roughly a $41 billion valuation. The company launched in November 2025 with a $6.2 billion Series A, so its valuation has quadrupled in about seven months. Backers include JPMorgan, BlackRock, Goldman Sachs, DST Global, and Arch Venture Partners. Headcount: around 150 people. The pitch is an “artificial general engineer” that helps small teams design and manufacture physical things.

Spence’s take: $41 billion for 150 people is a bet on the founder and the category, not the cash flow. Sometimes that bet’s right. The check size tells you how badly nobody wants to miss it.

3. NEURA Robotics landed the biggest full-stack robotics round ever

Germany’s NEURA Robotics announced a Series C of up to $1.4 billion at a reported ~$7 billion valuation, led by stablecoin issuer Tether, with Nvidia, Amazon, Qualcomm, Bosch, Schaeffler, and the European Investment Bank alongside. The company raised $55 million in 2023, so this is a roughly 25x jump in capital in three years. Read the word “up to” carefully: the full amount is tied to performance milestones. It’s a ceiling, not a wire transfer.

Spence’s take: The investor list maps almost perfectly onto the supply chain a humanoid business needs to exist. The money’s strategic before it’s financial.

4. Digital Asset pulled $355 million into regulated-finance rails

New York’s Digital Asset closed about $355 million this week, led by a16z crypto with Citi Ventures, Dragoneer, Accel, and 70-plus other investors, pushing total funding to roughly $500 million. The product is blockchain infrastructure for regulated financial markets. Less flashy than a rocket. Arguably stickier.

Spence’s take: Building in regulated markets is slow, unglamorous, and brutally hard to copy once you’ve done the compliance work. It’s the same reason a platform like /mkt runs Reg A+ offerings through established trading infrastructure rather than reinventing the rails. The moat is the paperwork nobody else wants to do.

5. PhysicsX raised $300 million to simulate the physical world

London’s PhysicsX closed a $300 million Series C at about a $2.4 billion valuation, led by Singapore’s Temasek, with NVIDIA, Siemens, Applied Materials, and Atomico in the mix. The company builds AI that simulates physics for engineering and hardware design.

Spence’s take: Notice who’s investing. Siemens and Applied Materials don’t write checks for vibes. When your customers fund you, the round is also a contract.

The signal underneath all five

Look at the list again. Rockets. Industrial engineering AI. Humanoid robots. Regulated finance rails. Physics simulation. Not a single pure software app in the bunch. Capital this week ran straight at companies fusing software with hard, physical, or regulated systems. The “AI wrapper” era is over. Atoms and regulation are back.

Going deeper on #1: the Margin of Safety

The mental model worth applying to the SpaceX debut is Margin of Safety, the gap between what you pay and what a thing is worth. At a $1.77 trillion valuation against $18.7 billion in revenue, the price works out to roughly 95 times sales, with a real net loss underneath it. That doesn’t make it a bad company. It makes the price one that leaves very little room for error.

Pair that with a deliberately thin float and a fixed offer price, and you get a setup primed for sharp moves in either direction. The model isn’t a verdict on SpaceX. It’s a discipline: when price runs far ahead of demonstrated value, your cushion is thin, and thin cushions punish surprises. Treat the opening sessions as price discovery, not a referendum. The first earnings report will start settling the argument the offer price can’t.

That’s not a call to do anything. It’s a lens for reading what’s in front of you.

If this was useful, share it with someone who builds things. And if you want the full toolkit of 50 mental models, my book is coming soon.

Next week’s deep-dive:

1. Anthropic Is Raising $50 Billion at a $900 Billion Valuation — And the Round Is Almost Closed

Anthropic asked investors to submit allocations within 48 hours last week for what is expected to be its final private round before an IPO, targeting roughly $50 billion at a valuation approaching $900 billion. For context: Anthropic raised at a $380 billion valuation in February — meaning this round more than doubles that in under three months, driven by a revenue run rate that has climbed from $9 billion at year-end 2025 to closer to $40 billion today.

Spence's take:

Revenue going 4x in four months earns a valuation doubling. The number isn't the story. The trajectory is.

Mental model: Compound Growth.

This is what exponential actually looks like in real time — not the hockey stick on a deck, but $9B to $40B in annualized revenue inside one calendar year. Over 1,000 enterprise clients are now spending more than $1 million a year each on Anthropic's AI services. That's not a consumer product with viral distribution. That's enterprise compounding: each new customer validates the next, each deployment generates proprietary data, and the cost of switching to a competitor grows with every integrated workflow. The moat isn't the model. It's the installed base building on top of it. Once that flywheel reaches critical mass, the valuation math starts looking less insane than it does on a spreadsheet.

2. Parker Files Chapter 7. $200M in Funding. Gone.

Parker, a YC-backed corporate credit card startup for e-commerce businesses, filed for Chapter 7 bankruptcy on May 7, citing assets and liabilities each between $50 million and $100 million. The company had raised more than $200 million in total funding, including a $125 million lending facility, and reportedly hit $65 million in revenue before going dark.

Spence's take:

$65 million in revenue and a Chapter 7 filing in the same week is the clearest possible proof that revenue and unit economics are not the same scoreboard.

3. Big Tech Is Spending $725 Billion in Capex This Year — While Cutting Headcount

Meta, Amazon, Microsoft, and Alphabet have collectively signaled roughly $725 billion in capital expenditures for 2026, almost entirely earmarked for data centers, chips, and AI models, a more than 75% increase year-over-year. At the same time, Meta plans to cut 8,000 employees in May, Amazon has shed roughly 30,000 roles in recent months, and Microsoft has offered voluntary buyouts to about 125,000 employees.

Spence's take:

The pattern is simple: more capital into infrastructure, less capital into headcount. The companies that built AI tools to automate operational work aren't being hypocritical. They're being consistent.

4. Ramp Is in Talks for $750M at $40B — Six Months After Closing at $32B

Ramp is in advanced talks to raise $750 million at a pre-money valuation exceeding $40 billion, co-led by GIC and Iconiq Capital. The company crossed $1 billion in annualized revenue in 2025 and has been raising at step-up valuations multiple times per year. Meanwhile, Brex — its nearest competitor — was acquired by Capital One earlier this year for $5.15 billion, roughly 60% below its peak valuation.

Spence's take:

Same market, same product category, two completely different outcomes. Ramp built moats. Brex built scale. The difference compounds fast when the environment gets competitive.

5. Iridius Raises $8.6M to Embed Compliance Directly Into AI Workflows

Seattle-based Iridius raised $8.6 million in seed funding led by Chalfen Ventures with Accenture Ventures as both investor and strategic partner, building a platform that transforms regulatory standards into machine-readable executable logic and embeds them directly into enterprise AI workflows — so compliance happens continuously as systems run, not as a retrospective audit layer.

Spence's take:

Most compliance software manages paperwork after the fact. Iridius is building the layer that makes paperwork unnecessary. That's a fundamentally different bet — and Accenture writing a check alongside strategic partnership tells you the market is real.

1. The AlphaGo Guy Just Raised $1.1B — Before Writing a Single Line of Product Code

Read more