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HOME/STRICTLYVC/OpenAI Is ThisClose to Filing
NEWS
// NEWSLETTER ISSUE
STRICTLYVC

OpenAI Is ThisClose to Filing

DATE May 22, 2026SOURCE STRICTLYVCPARTICIPANTS CONNIE LOIZOS
// KEY TAKEAWAYS5 ITEMS
  1. 01AI's Competitive Landscape Is Shifting Fast
  2. 02Government Is Becoming a Major Capital Allocator in Deep Tech
  3. 03The IPO Window Is Opening for High-Profile Tech Companies
  4. 04AI Infrastructure Is Attracting Massive Early-Stage Capital
  5. 05AI Regulation Is a Live Policy Battle With Real Market Consequences
In this episode
// SUMMARY

1. Key Themes

AI's Competitive Landscape Is Shifting Fast — and OpenAI May Not Be Winning

Despite being the category definer, OpenAI appears to be losing ground on both revenue momentum and profitability to Anthropic — even as it prepares to go public.

"Anthropic has since appeared to pull ahead, with annualized revenue nearing $45 billion versus approximately $30 billion for OpenAI. OpenAI also remains deeply unprofitable, while Anthropic could generate an operating profit in Q2."


Government Is Becoming a Major Capital Allocator in Deep Tech

The White House is deploying significant capital into quantum computing with equity stakes — signaling a new era of government as co-investor in strategic technology.

"The Trump administration said it will award $2 billion to nine quantum-computing companies, including IBM, D-Wave Quantum, Rigetti Computing, and PsiQuantum, in deals that also give the U.S. government equity stakes as Washington races to accelerate domestic quantum-computing development."


The IPO Window Is Opening for High-Profile Tech Companies

Multiple major tech companies are filing confidentially within the same news cycle, suggesting a meaningful opening in the public markets.

"OpenAI is reportedly preparing to confidentially file a draft of its IPO prospectus as soon as tomorrow." Additionally, "Oura...confidentially filed for an IPO after saying it is on track to surpass five million paid members and nearly $2 billion in annual sales next year." And "Blockchain.com...confidentially filed for an IPO. The company claims over 43 million users."


AI Infrastructure Is Attracting Massive Early-Stage Capital

Serverless AI infrastructure and AI-native hardware are commanding billion-dollar valuations at early funding stages, reflecting investor conviction in the infrastructure layer of the AI stack.

"Hark, a one-year-old San Jose startup that develops personalized AI systems and AI-native hardware devices, raised a $700+ million Series A round at a $6 billion post-money valuation." And "Modal Labs...raised a $355 million Series C round at a $4.65 billion post-money valuation" for "serverless cloud infrastructure for running and scaling AI applications."


AI Regulation Is a Live Policy Battle With Real Market Consequences

The federal government is actively divided on how to regulate AI, and that tension is now visibly shaping executive action — with direct implications for AI company operating environments.

"President Donald Trump postponed signing an executive order that would have expanded federal oversight of AI companies, saying he did not want to slow the U.S. in its AI race with China amid internal White House divisions over how aggressively the fast-moving industry should be regulated."


2. Contrarian Perspectives

OpenAI Filing for an IPO While Deeply Unprofitable Is a Notable Risk Signal

The conventional narrative frames the OpenAI IPO as a triumphant moment. But the financial reality is more complicated — and the timing raises questions about whether the IPO is being driven by strategic momentum or capital necessity.

"OpenAI also remains deeply unprofitable, while Anthropic could generate an operating profit in Q2." OpenAI generated "$5.7 billion in first-quarter revenue, about $1 billion more than Anthropic" just recently, but Anthropic has since surged to "$45 billion" annualized versus OpenAI's "$30 billion." Filing while losing the revenue race and remaining unprofitable is an unusual IPO posture.


Enterprise AI Deployment Is Not Plug-and-Play — Starbucks Is Proof

The dominant narrative is that AI tools are ready for enterprise deployment. Starbucks' rapid reversal on an AI inventory system suggests the operational reality is far messier.

"Starbucks has scrapped an AI-powered inventory-counting tool across North America less than a year after deployment, after workers complained that the system frequently miscounted products and mislabeled items like milk types."


SpaceX's Governance Structure Makes the IPO More About Musk's Liquidity Than Shareholder Opportunity

The SpaceX IPO will be framed as a historic wealth-creation event, but the voting structure means public investors are buying economic exposure, not governance rights.

"Musk controls and can vote those shares now...He owns just under 850 million Class A shares, entitled to 1 vote per share, and another nearly 5.6 billion Class B shares, entitled to 10 votes per share." Furthermore, "even a billion extra super-voting rights shares are immaterial in this company's setup because Musk is, by miles, the largest shareholder in the company."


3. Companies Identified

OpenAI Description: Leading AI research and product company Why mentioned: Preparing to confidentially file for IPO; losing revenue lead to Anthropic; remains deeply unprofitable Quote: "OpenAI is reportedly preparing to confidentially file a draft of its IPO prospectus as soon as tomorrow."


Anthropic Description: AI research company and OpenAI competitor Why mentioned: Surpassed OpenAI in annualized revenue and on track for operating profitability Quote: "Anthropic has since appeared to pull ahead, with annualized revenue nearing $45 billion versus approximately $30 billion for OpenAI...Anthropic could generate an operating profit in Q2."


SpaceX Description: Aerospace and satellite company founded by Elon Musk Why mentioned: S-1 analysis reveals extreme founder control and a projected $1.7 trillion valuation at IPO Quote: "The whisper number on the street is that this IPO will raise a whopping $75 billion, with a post-money valuation of $1.7 trillion."


Hark Description: One-year-old San Jose AI hardware/systems startup Why mentioned: Raised $700M+ Series A at $6B valuation with backing from NVIDIA, AMD, Intel Capital, Qualcomm Ventures, and others Quote: "Hark...raised a $700+ million Series A round at a $6 billion post-money valuation."


Kalshi Description: Prediction market exchange Why mentioned: Raised $200M Series F extension at a $22 billion valuation, signaling mainstream legitimacy for prediction markets Quote: "Kalshi...raised a $200 million Series F extension at a $22 billion valuation."


Modal Labs Description: Serverless cloud infrastructure for AI applications Why mentioned: Raised $355M Series C at $4.65B valuation, backed by Redpoint and General Catalyst Quote: "Modal Labs...raised a $355 million Series C round at a $4.65 billion post-money valuation."


Oura Description: Wearable health and sleep tracking smart ring company Why mentioned: Confidentially filed for IPO; on track for $2B annual sales and 5M paid members Quote: "Oura...confidentially filed for an IPO after saying it is on track to surpass five million paid members and nearly $2 billion in annual sales next year."


Manus Description: Singapore-based agentic AI startup Why mentioned: Meta's $2B acquisition is being unwound after Chinese regulators demanded reversal; founders seeking $1B to go independent Quote: "The co-founders of Manus...are reportedly exploring raising about $1 billion from outside investors to help unwind Meta's controversial $2 billion acquisition of the company after Chinese regulators demanded the deal be reversed."


Blockchain.com Description: Cryptocurrency wallet and trading platform Why mentioned: Confidentially filed for IPO with 43 million users Quote: "Blockchain.com...confidentially filed for an IPO. The company claims over 43 million users."


Scapia Description: Indian consumer travel and rewards platform combining booking, co-branded credit cards, and UPI payments Why mentioned: Raised $63M at $500M+ valuation led by General Catalyst, signaling continued emerging market fintech investment Quote: "Scapia...raised a $63 million round at a $500+ million post-money valuation."


Moment Description: AI applied to wealth management investment workflows Why mentioned: Raised $78M Series C backed by Index Ventures and a16z, reflecting AI-in-fintech investment theme Quote: "Moment...raised a $78 million Series C round led by Index Ventures, with Andreessen Horowitz and Avra also participating."


Starbucks Description: Global coffee chain Why mentioned: Case study in failed AI deployment — scrapped an AI inventory tool after less than a year Quote: "Starbucks has scrapped an AI-powered inventory-counting tool across North America less than a year after deployment, after workers complained that the system frequently miscounted products and mislabeled items like milk types."


4. People Identified

Elon Musk Description: Founder and controlling shareholder of SpaceX Why mentioned: Analysis of his outsized ownership and voting control in the SpaceX IPO Quote: "He owns just under 850 million Class A shares...and another nearly 5.6 billion Class B shares, entitled to 10 votes per share."


Donald Trump Description: U.S. President Why mentioned: Delayed AI oversight executive order due to concern about hampering the U.S.-China AI race Quote: "President Donald Trump postponed signing an executive order that would have expanded federal oversight of AI companies, saying he did not want to slow the U.S. in its AI race with China."


Gavin Newsom Description: Governor of California Why mentioned: Signed executive order exploring labor policy responses to AI-driven job displacement, including universal basic capital Quote: "California Governor Gavin Newsom signed an executive order directing California agencies to explore sweeping labor-policy changes aimed at addressing potential mass job displacement from AI, including expanded retraining programs, subsidies for companies that retain workers, and even concepts like universal basic capital."


Julie Bort Description: Journalist/contributor at StrictlyVC Why mentioned: Author of the SpaceX IPO ownership analysis Quote: "I could argue that the oddball provision where Elon Musk gets up to a billion more shares...once a million people are living on Mars...is perhaps the most jaw-dropping."


5. Operating Insights

AI Tools Require Rigorous Operational Validation Before Enterprise-Wide Rollout

The Starbucks failure is a cautionary tale: deploying AI at scale without sufficient accuracy testing can result in costly reversals, reputational damage with workers, and lost time.

"Starbucks has scrapped an AI-powered inventory-counting tool across North America less than a year after deployment, after workers complained that the system frequently miscounted products and mislabeled items like milk types."


AI-Generated Content Is Approaching Commercial Quality at Dramatically Compressed Costs and Timelines

For media, marketing, and entertainment operators, AI production timelines and cost structures are now viable at professional output levels — with the Cannes milestone as a credibility marker.

"Hell Grind, a 95-minute fully AI-generated film produced by a San Francisco startup in just two weeks, is set to premiere at the Cannes Film Festival. The production cost $500,000, $400,000 of which went toward AI compute costs."


Data Center Siting Is Becoming a Community Relations and Regulatory Risk Factor

Operators building or investing in data center infrastructure need to account for localized environmental and political backlash as physical impact research goes mainstream.

"Researchers at Arizona State University say waste heat from data centers can raise temperatures in nearby neighborhoods by as much as four degrees Fahrenheit, with the effect extending up to roughly five city blocks downwind in parts of the Phoenix metro area."


6. Overlooked Insights

Quantum-Safe Cryptography Is Already Attracting Commercial Investment

Buried in the smaller funding rounds, Quantum Bridge Technologies represents a timely opportunity — building encryption infrastructure that protects against quantum threats using existing networks, a near-term commercial need rather than a speculative future one.

"Quantum Bridge Technologies...develops quantum-safe cryptographic infrastructure that enables organizations to generate, distribute, and manage encryption keys across existing networks and security systems."


The Chinese Regulatory Environment Is Now a Material M&A Risk for U.S. Tech Acquirers

The forced unwinding of Meta's Manus acquisition is a first-mover signal that Chinese regulatory approval is now a blocking condition for acquisitions of China-linked AI startups — a deal-structuring risk that is underappreciated in current M&A frameworks.

"Chinese regulators demanded the deal be reversed...the co-founders of Manus are reportedly exploring raising about $1 billion from outside investors to help unwind Meta's controversial $2 billion acquisition."