Crash Expert: “This Looks Like 1929” → 71,105 Diversifying Here

Mark Spitznagel, who made $1B in a single day during the 2015 flash crash, warned markets are mimicking 1929. Seems extreme but we did just see the worst quarter for the S&P since 2022.

So it’s not so surprising that Vanguard and Goldman Sachs forecasted 5% and 3% annual S&P returns respectively for 2024-2034.

Late last year, Apollo’s chief economist Torsten Slok put it this way: "expect zero in return in the S&P 500 over the coming decade."

So, what’s something investors can actually do to diversify this week?

Almost no one knows this, but postwar and contemporary art appreciated 10.2% annually with near-zero correlation to equities from 1995–2025 overall.*

And sure… billionaires like Bezos can make headlines at auction, but what about the rest of us?

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^{*According to Masterworks data. Past performance is not indicative of future returns. Investing involves risk. Important Reg A disclosures: masterworks.com/cd.}

U.S. and China put frontier AI safety on the table

The U.S. and China are now talking about AI guardrails at a Beijing summit, according to Reuters, with a specific protocol aimed at keeping non-state actors away from the most powerful models. That is a notable shift: frontier AI safety is no longer just a lab policy debate or a regulatory headache -- it is becoming a geopolitical issue with national-security stakes. (investing.com)

What to watch next: whether the talks produce anything concrete, whether the agenda expands into verification or access controls, and whether other governments or major labs get pulled into the same framework. If this turns into an actual protocol rather than a photo-op, it could shape how model access and export controls are discussed for the rest of the year.

My Writing

As promised, I have a new FastCompany article about AI’s coming tipping point.

Other AI News

• OpenAI says it updated ChatGPT to better recognize warning signs that build over the course of a conversation, especially in high-risk cases (openai.com)

• OpenAI is also rolling out a beta Ads Manager for ChatGPT, with self-serve buying and CPC bidding for advertisers in the U.S. -- a clear sign the product's business model is getting more serious, and more commercial. (openai.com)

• Cerebras priced its IPO at $185 a share and then jumped hard in its debut, another reminder that AI infrastructure is still the market's favorite expensive habit. (investing.com)

Today's Strangest AI

Former Roomba chief Colin Angle has a new robot project: Familiar, a plush, four-legged AI pet prototype that looks part household gadget, part emotional support animal, part sci-fi demo piece. It is weird in exactly the way product demos are supposed to be -- slightly adorable, slightly unsettling. (apnews.com)

Someone just spent $236,000,000 on a painting. Here’s why it matters for your wallet.

Late last year, a Klimt sold for the highest price ever paid for modern art at auction.

An outlier sure, but it wasn't a fluke. U.S. auction sales grew 23.1% in 2025. The $1-5mm segment even grew 40.8% YoY.

Meanwhile, Apollo’s chief economist Torsten Slok said to expect ‘zero in return in the S&P 500 over the coming decade.’

So, that's where it gets interesting.

Each environment is unique, but after dot-com, post war and contemporary art grew about 24% annually for a decade. After 2008, about 11% for 12 years.

It’s also had near-zero correlation with the S&P 500 since ‘95.*

Now, Masterworks lets you invest in shares of artworks featuring legends like Banksy, Basquiat, and Picasso.

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^{*Investing involves risk. Past performance is not indicative of future returns. See important Reg A disclosures at masterworks.com/cd.}

OpenAI Wants a Consulting Practice, Too

OpenAI is launching the OpenAI Deployment Company, a new business unit built around getting AI into real customer workflows. The company says it is acquiring Tomoro and starting with more than $4 billion in initial investment to embed forward deployed engineers inside enterprise systems. That is a notable shift in posture -- from shipping models to owning the messy middle where software actually gets used.

The strategic point is simple: the next AI fight is not only about who has the best model. It is about who can make AI work inside security reviews, legacy systems, compliance teams, and the daily habits of real businesses. If this unit gets traction, expect OpenAI to look less like a model vendor and more like a deployment partner. Watch which customers adopt first, how the service is packaged, and whether rivals answer with their own integration arms.

Tom’s Take

Anthropic did literally the same thing earlier this month. We can only assume that OpenAI was planning this for a while longer (although it would be very Sam Altman to throw $4 billion at something just because Anthropic did that something.)

Most likely, Anthropic just beat OpenAI to the punch. Either way, two big AI companies doing the same thing indicates that this is the direction the industry is moving.

Building models only gets you so far. Actually getting enterprises to build your AI deeply into the systems is when really impactful things start to happen.

I’ll have a new article on a similar topic coming out later this week. Stay tuned!

Other AI News

• Google says Android is moving toward an intelligence system, with Gemini taking on more task automation across apps and devices. Read the developer note on the Android developer blog -- this could change what phone software is for, not just how it looks.

• OpenAI launched Daybreak, a cyber defense platform that connects models, Codex, and security workflows for code review, threat modeling, patching, and verification. It is a sign that frontier AI is moving deeper into security ops, where the upside is real and the governance questions are unavoidable.

• Google is updating AI Mode and AI Overviews to surface more source links, original sources, and richer previews. That is good news for anyone who wants the web to stay visible inside AI search -- and not just get swallowed by it.

Buy This

I asked the company BougeRV to send a car cooler for me to test, and they sent me an ultra-powerful, motor-driven wagon instead.

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I’m obligated to tell you that people can’t ride in it like a Go Kart, and to assure you that if they did decide to ride in it, that would be no fun at all for them and certainly wouldn’t make a really hilarious video to send to their family members.

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Today's Strangest AI

South Korea ordained a robot monk named Gabi. The image in the linked article is exactly as strange as it sounds -- robotics, religion, and ritual all sharing the same room.

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Anthropic's $200 billion compute bet

Reuters reports that Anthropic has committed to spend $200 billion with Google Cloud over five years, including Google's chips -- a reminder that frontier AI is as much an infrastructure business as a model business.

If the deal holds up as described, it would deepen one of the industry's biggest compute relationships and push the price of staying at the frontier even higher. See the reports from Reuters via Investing.com and Anthropic's own note on its Google/Broadcom compute partnership here.

The broader signal is hard to miss: the bottleneck is still compute, and the biggest labs are now among the biggest customers in tech. That matters for pricing, capacity, and how quickly Claude can scale. The thing to watch next is whether the deal is confirmed in full detail -- and whether rivals respond with their own long-term commitments.

Tom’s Take

While we hear the most about exciting companies like Anthropic and OpenAI, it’s the “hyperscalers” (giant companies like Google, Microsoft, Oracle and Meta) that are building the datacenters powering the AI boom.

Anthropic and OpenAI are increasingly dependent on these companies to feed the massive demand for computing capacity that powers frontier models. And it’s now a multi-hundred-billion dollar prospect.

Other AI News

• The US government is widening pre-release testing for frontier models. NIST said CAISI signed new agreements with Google DeepMind, Microsoft and xAI for pre-deployment evaluations and targeted research.

• OpenAI reportedly gave GPT-5.5 to the US for national security testing before public release, another sign that government review is becoming part of the launch process for top-tier models.

• OpenAI and PwC are teaming up on finance agents for CFO workflows, including planning, forecasting, reporting, and procurement. The announcement is a useful marker for where enterprise AI is still most believable: inside messy, repeatable business processes.

Today's Strangest AI

Anthropic says it will use the full computing capacity of SpaceX's Colossus 1 data center, which has 220,000 NVIDIA GPUs. It’s the craziness of 2026’s AI scene in a nutshell: a frontier lab renting massive compute from a space company.

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Anthropic moves from model maker to enterprise operator

Anthropic is no longer just selling Claude. It is now helping build the plumbing around it. The company announced a $1.5 billion enterprise AI joint venture with Blackstone, Hellman & Friedman, Goldman Sachs, and other financial sponsors, aimed at deploying AI services inside large businesses.

The setup is less about a flashy model release and more about putting engineers and implementation muscle directly into portfolio companies. Read more in TechCrunch and Fortune.

That matters because it shows where the real money and control may be heading: not just in training frontier models, but in distribution, services, and operational lock-in.

If this works, it becomes a template for how AI gets sold into big enterprises -- not as software you buy, but as capability you install. The big question now is whether this turns into repeatable revenue, or just a very expensive way to dress up partnership theater.

Tom’s Take

Software companies have long used so-called “forward deployed engineers” to help their clients adopt the company’s tech.

These FDEs essentially embed with a client company, directly setting up software for the client’s team.

It’s a fantastic strategy in the software world, as client companies quickly become dependent on the FDE and the tech they’re installing.

Now, Anthropic wants in on the action! This new venture looks like an attempt to apply the FDE model to the world of AI.

If it works, it could be a huge boon both to Anthropic and to AI adoption more generally. Implementing AI is hard, but the payoffs are huge. Having a pro from Anthropic do the dirty work for you will likely be irresistible to many big companies.

Other AI News

• Anthropic also released The 2026 State of AI Agents report, which should help separate real adoption from the usual agent hype.

• NIST launched the AI Agent Standards Initiative, a slow-burn effort that could matter a lot once agents become normal enterprise software.

• Google expanded Deep Research with a new Max tier built on Gemini 3.1 Pro, pushing autonomous research deeper into knowledge-work workflows via its product update.

Today's Strangest AI

Beeple's robot dogs with tech-bro heads are roaming a Berlin museum, printing AI-generated images and generally making the future feel more like satire than product demo. AP covered the whole gloriously unsettling scene.

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AI May Actually Make Money, Google's Results Show

Alphabet (Google’s parent company’s) Q1 2026 results were a blunt reminder that AI is no longer just a product story for Big Tech -- it is a revenue story.

The company said total revenue rose 22% to $109.9 billion, Search revenue grew 19%, and Google Cloud revenue jumped 63% to $20.0 billion. Sundar Pichai said AI experiences are driving Search usage and that Cloud growth is being led by enterprise AI solutions and infrastructure.

That matters because it is the cleanest sign yet that AI can move from demo to durable business engine at platform scale. Alphabet is now saying the same thing three ways -- more Search usage, faster Cloud growth, and rising demand for Gemini-based products -- which is exactly what investors and competitors have been waiting to see. The open question is whether it can keep turning AI usage into demand.

Tom’s Take

There’s an old saying from the 1990s that “Technology is showing up everywhere except the productivity figures.”

Nerdy, I know. But the gist is that the computer tech taking off at the time wasn’t really changing the business world.

Then, over time, of course it changed everything.

People have been watching to see if AI follows a similar path. So far, the tech hasn’t earned much, in the grand scheme of things. Again, as I shared in a previous newsletter, OpenAI’s total revenue is comparable to the $17 billion earned by the pizza delivery industry last year.

Google’s results, though, show that AI might finally be “showing up in the figures” in a meaningful way. If that continues, all the money poured into AI data centers might actually pay off!

Other AI News

• Microsoft says next-generation AI is speeding up vulnerability discovery and changing the definition of security risk, a useful reminder that better AI also means faster offense and a more demanding defense.

• Nebius agreed to acquire Eigen AI and fold its inference and post-training optimization stack into Nebius Token Factory, another signal that the inference business is becoming a competition over cost, speed, and unit economics. (nebius.com)

• Palo Alto Networks said it plans to acquire Portkey to help secure autonomous AI agents, underscoring how quickly AI governance is becoming a standard enterprise security category. (investors.paloaltonetworks.com)

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America's Weapons, Powered by Google's AI

Axios reported that the Pentagon has reached an agreement with Google to use its model for "all lawful use.”

The reported deal would expand Google's role in military work and push frontier AI further into the procurement pipeline, where policy, contracts, and real-world deployment start colliding fast. (axios.com)

Also colliding fast? AI-guided bombs and anything America wants destroyed!

The larger significance is less about one contract than about normalization. If major labs keep taking government work in this direction, the debate shifts from "should AI be used by the military?" to "what limits, if any, are actually enforceable once it is?"

That is where oversight gets real -- and where lawmakers may decide they need clearer guardrails, especially if other frontier labs move to strike similar deals. (axios.com)

Tom’s Take

This is a huge change for Google. Most Googlers don’t want to feel like they’re working for a defense contractor, and in the in past, they’ve cratered deals like this one.

The fact that Google is getting cozy with the DoD suggests that it’s put an end to its employee revolts.

With their own jobs disrupted by AI, engineers may feel lucky to be employed and less inclined to speak out against their employer’s choices than they did in the go-go days of 2022.

For Silicon Valley newcomers, big tech companies working with the military might seem like a departure. But in reality, Silicon Valley’s history is deeply intwined with defense. In many ways, Google’s deal reflects the Valley’s origin story coming full circle.

Other AI News

• OpenAI and Anthropic separately briefed House Homeland Security Committee staff on their cyber-capable models, a sign that advanced AI is becoming a congressional cybersecurity issue, not just a product launch talking point. (axios.com)

• OpenAI says ChatGPT Enterprise and its API Platform have reached FedRAMP Moderate authorization, opening the door to broader U.S. government use if agencies choose to adopt them. (openai.com)

• Microsoft said its AI business hit a $37 billion annual revenue run rate and Azure revenue rose 40% in the latest quarter, underscoring that enterprise AI spending is still very real even when investors want faster proof of payoff. (news.microsoft.com)

Today's Strangest AI

Waymo has found another killer app for its self-driving tech: fixing potholes! The company is now working with cities like Los Angeles to use the sensors on its self-driving cars in order to map the city’s potholes and get them repaired faster.

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Microsoft Loves OpenAI And Lets it Go

To paraphrase the immortal Sting, if you love something, you shouldn’t jealously hoard it all for yourself. This week, Microsoft followed Sting’s advice and let OpenAI be free, rather than keeping the company’s tech locked down in its own cloud.

To be clear, OpenAI’s tech decidedly isn’t free for you to use. But it’s free from the closely-guarded garden of Azure. And that’s a big deal for one Microsoft cloud competitor: Amazon.

AWS says OpenAI models, Codex, and Managed Agents are now available in limited preview on Amazon Bedrock. That puts OpenAI inside Amazon's enterprise cloud stack for the first time in a meaningful way, and gives customers another path to frontier models outside Microsoft's ecosystem. For buyers who already live in AWS, that's not a side note -- it's a routing change.

The bigger point is distribution. If OpenAI's products can be bought and governed through AWS, enterprise AI gets a little less tied to one cloud vendor and a little more normal, in the boring, expensive, multi-cloud way companies actually operate.

Axios and TechCrunch both frame this as an important shift in the cloud relationship. What to watch next: whether the preview widens to general availability, whether Microsoft pushes back, and whether large customers start standardizing on OpenAI through AWS instead of treating it as a Microsoft-only option.

My Stuff

Along with my friend Jared Bauman, I built an AI-powered poem generator, and released it onto the open internet.

I had no idea how people would use it. And it turns out, the answer is fascinating.

That’s the subject of my latest FastCompany article, which came out this morning.

Other AI News

• The White House is reportedly looking for a way to bring Anthropic back into government work, with Axios reporting that agencies could get new guidance to work around Anthropic's supply-chain-risk designation.

• Bipartisan lawmakers are taking aim at AI chatbots and fraud, with new bills that would add family accounts, child chat log access, and time limits, according to Reuters coverage.

• DeepSeek is still pressing on price, with its V4 preview reportedly offering a 1 million-token context window, open weights, and aggressive pricing -- a reminder that frontier competition is not just about model quality.

Today's Strangest AI

The Vatican is trying to build digital defenses and guidelines for AI-driven manipulation. An ancient institution is now acting a little like a tech regulator. What a world!

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OpenAI's Growth Math Gets a Little Less Magical

OpenAI is reportedly running into a very unglamorous problem for a very glamorous company: it is missing internal revenue and user targets while pushing toward an IPO.

Reuters, via StreetInsider and TradingView, says leadership is worried about whether the company can support its huge data-center commitments. The report also says ChatGPT growth has slowed and OpenAI fell short of a goal to reach 1 billion weekly users.

That is the kind of update investors tend to notice. For most of the last two years, the AI story has been about model launches, distribution, and who gets the biggest slice of attention. This version is about capex, conversion, and whether the market's most important private AI company can turn usage into a business that justifies the bill.

Tom’s Take

Since ChatGPT rolled out, OpenAI has been on a pretty magical trajectory—raising over $100 billion without an IPO, building some of this century’s hottest tech, and the like.

There’s also been some magical thinking about the company’s valuation, though! OpenAI only earns around $20 billion in revenue.

For context, pizza delivery is a $17 billion industry. AI is cool, but it doesn’t earn much.

Investors overlooked that while OpenAI was still growing rapidly. Any signs that growth has slowed, though, could have severe consequences—especially going into an IPO.

You can bet that future OpenAI investors will be watching carefully to see if this downward trend continues.

Other AI News

• A federal trial began in Oakland over Elon Musk's claim that OpenAI abandoned its nonprofit mission and became a profit-seeking machine, a case that could shape how courts think about the company's governance and obligations.

• Reuters reported that Google signed a classified AI deal with the Pentagon, adding more defense work to the list of real customers for frontier models.

• OpenAI and Microsoft amended their partnership so OpenAI can serve products across any cloud provider, while Microsoft's license to OpenAI IP becomes non-exclusive -- a meaningful shift in the cloud and distribution fight.

Today's Strangest AI

Meta reportedly signed onto a plan to use satellites to beam infrared light to solar farms at night. It sounds like a pitch from a sci-fi studio memo, but it is being floated as actual infrastructure for AI power demand.

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The Race to Unseat NVIDIA Is On

Google used Cloud Next '26 to unveil TPU 8t and TPU 8i, its eighth-generation AI chips split between training and inference. The company is framing the move as part of a broader push around the "agentic enterprise" -- not just faster silicon, but a fuller cloud stack for model builders and corporate buyers. (blog.google)

That is what makes this more interesting than a normal product launch. Google is not just adding another cloud feature -- it is trying to chip away at Nvidia's hold on AI infrastructure economics.

Basically, Google Cloud is launching two new AI chips to compete with Nvidia. The real question now is whether customers actually move workloads, or whether this becomes another impressive demo that mostly helps Google show its investors that it’s still on the cutting edge.

Tom’s Take

As the old adage goes, during a gold rush it’s not the miners who get rich…it’s the shovel sellers.

NVIDIA is the quintessential “shovel seller” of our current AI gold rush. The company sells the chips on which nearly every AI company depends. And that has made it fabulously valuable.

Unsurprisingly, other companies want a piece of that AI pie. Making cutting-edge chips is hard though; a single piece of chip-making equipment can cost hundreds of millions of dollars.

Who has the resources to compete? Other big tech companies. That’s why we’re seeing Google enter the race. Others will surely follow.

Other AI News

• DeepSeek previewed V4 Flash and V4 Pro, saying both models support 1 million-token context windows and come in at aggressive price points. The pitch is simple: close the gap on frontier performance while keeping costs low.

• Thinking Machines Lab keeps pulling in Meta talent, and it is also benefiting from a multibillion-dollar Google cloud deal that gives it access to Nvidia GB300-based systems. That is the AI race in one sentence: people, compute, and who can pay for both. (techcrunch.com)

• OpenAI published a child safety blueprint. It is a reminder that the safety work around frontier models is getting more concrete, and more public. (openai.com)

Today's Strangest AI

Noscroll is an AI bot that doomscrolls for you, then texts you when it finds something worth your attention. We have now automated one of the least admirable human habits, which is either efficient or deeply on brand.

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Google Cozies up to Anthropic With $40 Billion Bet

Alphabet is reportedly preparing a deal worth up to $40 billion in cash and compute to deepen its relationship with Anthropic, according to Bloomberg and TechCrunch. If it lands as reported, this is a very public sign that frontier AI is settling into a small number of alliances between model labs and the companies that control the chips, cloud contracts, and balance sheets.

Why it matters: model competition now depends as much on infrastructure access as on clever research. A tighter Google-Anthropic relationship would sharpen that reality for rivals, regulators, and enterprise buyers alike. The next things to watch are whether the deal is finalized on these terms, what strings come with the compute commitment, and whether competitors answer with their own financing or cloud tie-ups.

Tom’s Take: This deal suggests that Google is only afraid of one competitor: OpenAI. The company is willing to cozy up to Anthropic, nominally a rival, if it means a better shot at beating its true rival, Sam Altman’s world-leading company.

Basically, I read this as a modern instance of “the enemy of my enemy is my friend” and an indicator that Google sees frontier AI as a two horse race.

More Top AI Stories

• Anthropic also expanded its Amazon relationship with a compute pact reportedly worth more than $100 billion over 10 years, with Axios framing it as a fresh sign that cloud capacity is becoming the real choke point in the frontier race.

• In a Pentagon-related dispute, Anthropic told an appeals court it has no "kill switch" for Claude once the system is deployed inside classified customer environments, according to Axios and the court filing. That is a dry legal detail with a sharp edge -- it gets at how much control an AI company really has after deployment.

• OpenAI released GPT-5.5, pitching it as a stronger model for coding, research, data analysis, and multi-step computer work, with TechCrunch calling it a major new shot in the frontier model race. Amid all the financing news, this is the reminder that product capability still moves the market.

Today's Strangest AI

Sony AI's Ace robot is now beating elite table tennis players, according to a new Nature paper and an AP report. It sounds faintly ridiculous until you think about what table tennis requires -- fast perception, planning, control, and constant adaptation. A gimmick, in other words, that is also very much not a gimmick.

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George From Seinfeld Interviewed Me About AI and Investing

I’ve been sitting on this one for a while!

In December (on my birthday!) I sat down with Jason Alexander (known to many for his iconic role as George Costanza in Seinfeld) and his co-host Peter Tilden on the Really? No Really? Podcast to talk about my ChatGPT investing experiment.

If you missed that experiment, last year I asked ChatGPT to pick $500 worth of stocks for me to invest in.

Then I pulled up Robinhood, transferred $500 actual dollars from my bank account, and bought exactly what it recommended. Here’s the article on FastCompany and Medium.

I spoke with Jason and Peter around the halfway mark in my experiment. And boy, was it a wild ride (the experiment—Peter and Jason were lovely)!

We also talked about how to raise kids in an AI-dominated world, why chatbots’ confidence can be their downfall, and the right way to pronounce “Johns Hopkins.”

Here’s the episode on YouTube (if you want proof that this was actually Jason Alexander and not an Elevenlabs clone of his voice) and Apple Podcasts.

(Ps. Sadly, the clip of Jason and Peter singing me “Happy Birthday” didn’t make it onto the show, but their harmonies were top-notch).

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There used to be a huge chasm between the performance of “Instant” models from the likes of OpenAI and Anthropic, and their more resource-intensive “Thinking” models.

Most pro users wouldn’t touch the “Instant” ones. They were for free ChatGPT users, or for very basic tasks, like reformatting text or answering a question for your kid’s science project.

With OpenAI’s most recent model release, though, that has changed. The new GPT-5.3 Instant model is extremely good. It’s also extremely fast.

That suggests a new direction for how frontier models get built. Will it mean the end of “Thinking” models for regular users? Here’s an article I wrote exploring this.

OpenAI’s New Frontier Models Mark a Huge Change in How AI Will be Built

Goodbye to “thinking” LLMS?

medium.com/the-generator/openais-new-frontier-models-mark-a-huge-change-in-how-ai-will-be-built-fea58b9a239d?sk=abad9360e0ed06e8d50db17ce33772bc

Why Timothée Chalamet is Wrong

If you care about culture, you were probably very angry when actor Timothee Chalamet said opera was dying.

In my latest FastCompany article, I explore a strange trend: as AI eats the world, people are turning to analog artforms (yes, including opera) more, not less.

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OpenAI Raises $110 Billion in Gigantic New Funding Round

OpenAI said Friday (February 27, 2026) that it has secured $110 billion in new investment in what ranks among the largest private funding rounds ever, pegging the company at a $730 billion pre-money valuation.

Who put up the money

OpenAI says the round includes:

• Amazon: $50 billion

• Nvidia: $30 billion

• SoftBank: $30 billion

OpenAI also noted the round is expected to expand with additional financial investors as it progresses.

The funding is not just about cash — it is tied to major infrastructure commitments.

Credit: Thomas Smith

Reuters reported that Amazon Web Services will become the exclusive third-party cloud provider for OpenAI Frontier (OpenAI’s enterprise platform for managing AI agents), and that OpenAI will use 2 gigawatts of compute running on Amazon’s Trainium chips as part of the deal.

OpenAI emphasized that its relationship with Microsoft remains intact. Reuters reported Microsoft Azure stays the exclusive cloud provider for OpenAI’s API services, and Microsoft’s exclusive license to OpenAI models and products remains unchanged.

My Take

This gigantic deal means the AI bubble is likely not yet close to popping. OpenAI has said that it plans to burn through hundreds of billions of dollars before it becomes profitable.

There were some concerns about whether investors would be able to stomach that. Apparently, they had no issue with it—the round is done, and major companies and investment groups are onboard.

OpenAI will now have enough cash to sustain itself and grow for quite some time. That influx alone should allay fears about an immediate bubble burst.

It’s also a huge deal for private companies. Before, you needed to do an IPO and go public to raise these kinds of sums. Now, that’s apparently no longer required.

The round reportedly values OpenAI at $730 billion, with no public money onboard. Of course, OpenAI could still go public later to raise even more colossal sums!

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OpenAI and Anthropic keep releasing new, wildly powerful frontier models. But that's not what everyone is talking about.

Instead, the AI hype cycle is right now focused on a tiny, weird, open-source AI tool: OpenClaw.

Why this oddly independent system, you ask?

Big AI companies have long promised consumers “agentic AI" that could take action on their behalf. So far, that has largely failed to materialize.

In contrast, OpenClaw puts AI agents that can truly do useful things into the hands of anyone willing to undertake the (admittedly, very annoying) process of setting up the system.

I decided to do just that. I built an OpenClaw agent to do my job at FastCompany for me.

The results were powerful—and way more expensive that I expected. In building my agent, I got a good sense for why agentic AI isn't mainstream yet. That’s all covered in today’s FastCompany article (not actually written by OpenClaw!)

I built an OpenClaw AI agent to do my job for me. The results were surprising—and a little scary

OpenClaw did a surprisingly good job following journalistic best practices. 

www.fastcompany.com/91495511/i-built-an-openclaw-ai-agent-to-do-my-job-for-me-results-were-surprising-scary

Everything to Know About GEO

Want to learn about applying GEO in your own business? Jared Bauman and I are doing a webinar for DMLA members later today.

It’s free if you work for companies like Getty Images, Shutterstock, etc. and about $30 for non-members.

GEO and Search in 2026: Everything to Know

Search has moved beyond blue links. AI Overviews and chatbots now drive buying. LLM traffic up 357%—learn GEO best practices for 2026.

www.eventbrite.com/e/geo-and-search-in-2026-everything-to-know-tickets-1982727040953

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The Real, Sci-Fi Reason Elon Musk Merged His Companies

Elon Musk is officially merging two of his companies, xAI and SpaceX. The former makes generative AI models, and the latter flies things into space.

Lots of things—fully 95% of the objects that America sends to space are put there by SpaceX.

At first, it seems like the two companies have nothing to do with each other. But as I explain in my most recent FastCompany article, there’s a real reason to merge the companies: data centers in space.

Sound outlandish? Feel like a sci-fi dream?

Perhaps it is. But Elon Musk is taking the idea of launching AI data centers into space extremely seriously. And it’s actually gaining mainstream interest, too.

Here’s a look at why the merger of these two companies could mean flying data centers orbiting the earth (yes, really), and sooner than you might expect.

Generative Engine Optimization (GEO) is the art of getting your brand mentioned—and talked about favorably—in powerful chatbots like ChatGPT and Claude, and in Google’s AI Overviews.

Having a great About page is crucial for GEO. To a far greater extent than traditional search engines, the LLMs behind today’s chatbots look at your About page (and related ones like Team and Press) to understand who you are and whether you’re legit.

In my own GEO consulting practice, it’s the #1 content mistake I see brands make. They neglect the About page, or worse, publish an outdated version with press from 6 years ago and a mission statement they forgot they wrote.

That’s why I built a powerful new system that polls popular LLMs, crawls news sources, looks at customer reviews, reads your LinkedIn page, and then gathers all that data into one place to help you create an About page that LLMs love.

Now that it’s ready, I’m offering it to my newsletter subscribers for FREE for a short time, as a “thanks” for following me.

Here’s how this works. Send me your brand name and URL, and I’ll run the system on your brand, gather all the data, and then apply my own expertise to craft it into an About page for you.

I’ll send it along for you to check out. If you like it, you’re welcome to grab any of the language on there and use it on your site. No strings attached and no commitment. I’d love your feedback on how the system does.

I’m going to limit this to 50 brands (one per subscriber, please) to preserve my own time/sanity. So please reach out right away if you’re interested.

To do this, just reply to this message with your brand name and URL.

Thanks, and let’s get you a proper About page!

Last Time the Market Was This Expensive, Investors Waited 14 Years to Break Even

In 1999, the S&P 500 peaked. Then it took 14 years to gradually recover by 2013.

Today? Goldman Sachs sounds crazy forecasting 3% returns for 2024 to 2034.

But we’re currently seeing the highest price for the S&P 500 compared to earnings since the dot-com boom.

So, maybe that’s why they’re not alone; Vanguard projects about 5%.

In fact, now just about everything seems priced near all time highs. Equities, gold, crypto, etc.

But billionaires have long diversified a slice of their portfolios with one asset class that is poised to rebound.

It’s post war and contemporary art.

Sounds crazy, but over 70,000 investors have followed suit since 2019—with Masterworks.

You can invest in shares of artworks featuring Banksy, Basquiat, Picasso, and more.

24 exits later, results speak for themselves: net annualized returns like 14.6%, 17.6%, and 17.8%.*

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_{*Investing involves risk. Past performance is not indicative of future returns. Important Reg A disclosures: masterworks.com/cd.}

Is Google's $260 Billion Ad Empire Doomed?

Advertising is the engine that drives the Internet. And it’s an incredibly powerful one.

Google still makes most of its money from ads. To be precise, it makes over $260 billion every year from advertising alone.

Even Amazon—best known, of course, for its Ecommerce business—now makes almost $60 billion per year from ad sales.

Now, a new player is getting into the market: OpenAI.

As my most recent article in FastCompany shares, OpenAI has a huge running start. It already has a user base that includes almost 10% of humans on the planet. And it knows a LOT about those people.

People spend an average of 10-20 second on a Google search. In contrast, they spend an average of 12 MINUTES on each “session” with ChatGPT. That’s enough time for the bot to learn a lot about their wants and needs.

Here’s why that matters—and why OpenAI could be threatening Google’s ad empire in short order.

OpenAI could take down Google’s $260 billion ad empire. Here’s how

OpenAI’s exquisite knowledge of its users’ needs means it can likely sell ChatGPT ads for a premium.

www.fastcompany.com/91481063/openai-could-take-down-googles-260-billion-ad-empire

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How to Mine ChatGPT's Memory for Killer New Year's Resolutions

ChatGPT remembers everything. That’s the someone creepy conclusion I came to recently when I tried mining ChatGPT’s memory to come up with a killer list of New Year’s resolutions.

Many people don’t realize that ChatGPT is quietly parsing everything you ask it, and storing lots of details about who you are and what you care about.

In my most recent FastCompany article, I show how to check what ChatGPT knows about you.

In my case, I found that the bot knows my age, marital status, where I live and the names of my kids. It also thought I was “writing an article about asphalt”. Figure that one out!

Sam Altman says that OpenAI will lean heavily into its “Memory” system in 2026. He called it a breakthrough AI technology. So ChatGPT is going to learn even more about what makes you tick.

That’s creepy. But it’s also useful!

In my article, I share an experiment with mining ChatGPT’s memory to craft a list of killer, highly-specific New Year’s resolutions. I even share the prompt that I used to do it for myself, so you can try this, too.

Here’s the article.

I asked ChatGPT to help me come up with killer New Year’s resolutions. Here’s what happened

It creeps me out a bit to see how much ChatGPT knows about me.

www.fastcompany.com/91470687/chatgpt-new-years-resolutions

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Meet The Guy Whose Obscure PHD Research is Our Best Shot for Fighting AI Image Chaos

One of the coolest things about working in tech is that you get to see your friends do amazing things, build them into companies, and ideally thrive.

I met Victor Riparbelli back in 2018, for example, while his company was a tiny, scrappy startup. Now it’s worth a reported $4 billion.

Likewise, I spent two years during the pandemic volunteering to help my industry’s non-profit trade group pivot its annual in-person conference to an online format. During that time, I met Dr. Eric Wengrowski of Steg AI.

For years, Eric toiled away on a very specific, largely obscure technology for invisibly tracking images, derived from his PHD research. He had some traction, but it was in very specific sectors and a bit esoteric.

Then, all of a sudden, AI image generators arrived. Tracking images became a matter of truth, veracity and even national security. And tech like Steg’s became humanity’s best shot for fighting AI image chaos.

Formerly working mostly in the background, Eric woke up one day to find the President of the United States had called out his company’s tech in an Executive Order from the White House.

Steg has exploded. The company’s revenue is up 500%, and Eric’s life has changed dramatically. I caught up with him for my most recent piece in Fast Company and shared his story.

This guy’s obscure PhD project is the only thing standing between humanity and AI image chaos

Images look no different after being marked with a steganographic watermark than they did before.

www.fastcompany.com/91458224/steg-ai-images-watermark-phd-project-wengrowski

If you don’t have Fast Company access, you might enjoy this interview I did with Eric four years ago on my YouTube channel.

Our focus on NFTs dates the video a lot 🙂 But in it, we talk a lot about what Steg’s tech does and why it matters.

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OpenAI's GPT-5.2 is Out. Everything to Know.

On Thursday, OpenAI released its new GPT-5.2 model. So naturally, I headed to their SF headquarters, walked around (getting a definite stink-eye from a security guard, and narrated exactly what you need to know about the new model.

Here’s the video:

For a deeper analysis, I also did a writeup for FastCompany:

OpenAI just released its new GPT-5.2 model. Here’s what you need to know

OpenAI's new GPT-5.2 model is faster, more efficient, and better at solving technical problems.

www.fastcompany.com/91459501/openai-just-released-new-gpt-5-2-model-heres-what-you-need-know