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HOME/STRICTLYVC/GameStop's CEO Struggles to Expl…
NEWS
// NEWSLETTER ISSUE
STRICTLYVC

GameStop's CEO Struggles to Explain His eBay Offer

DATE May 5, 2026SOURCE STRICTLYVCPARTICIPANTS CONNIE LOIZOS
// KEY TAKEAWAYS5 ITEMS
  1. 01Enterprise AI Adoption Is Accelerating
  2. 02AI Infrastructure Capital Is Pooling Into Deployment Vehicles, Not Just Models
  3. 03Amazon Is Moving Aggressively to Disrupt Legacy Logistics
  4. 04Non-Human Identity Security Is a Validated M&A Category
  5. 05Clean Energy Infrastructure Is IPO-Ready and Commanding Premium Valuations
// SUMMARY

1. Key Themes

Enterprise AI Adoption Is Accelerating — and Expensive Before It Pays Off

The race to deploy enterprise AI is creating massive funding rounds and real revenue traction, but the cost curve hits hard before returns materialize. Sierra went from four design partners to "more than 40% of the Fortune 50 as customers" and grew ARR from $100M in November to $150M by February — roughly $50M in ~90 days. Yet even large, sophisticated adopters are burning through budgets fast.

"Uber CTO Praveen Neppalli Naga put it plainly…saying that Uber 'blew through our [AI] budget' soon after opening the door to agentic AI tools late last year. He also said the company is starting to see meaningful results."

"Taylor…has said that the best-case outcome for agentic AI is lower costs and higher revenue for clients, but before those returns materialize, the ramp-up phase can be pricey."


AI Infrastructure Capital Is Pooling Into Deployment Vehicles, Not Just Models

Both Anthropic and OpenAI are now standing up structured capital vehicles specifically to fund enterprise AI deployment — signaling a maturation from R&D funding to commercialization infrastructure.

"Anthropic is forming a roughly $1.5 billion venture, with investors including Blackstone, Hellman & Friedman, and Goldman Sachs; while OpenAI has raised more than $4 billion for a new venture called The Deployment Company backed by 19 investors including TPG, Brookfield, Advent, and Bain Capital."


Amazon Is Moving Aggressively to Disrupt Legacy Logistics

Amazon is now openly competing with UPS and FedEx by opening its logistics infrastructure to all businesses — a direct challenge to incumbents who lack Amazon's scale and data advantages.

"Amazon is opening its logistics network to all businesses through a new service called Amazon Supply Chain Services, putting it in more direct competition with UPS and FedEx."


Non-Human Identity Security Is a Validated M&A Category

Cisco's acquisition of Astrix Security confirms enterprise demand for tools that govern AI agents, API keys, and automated systems — a category that will only grow as agentic AI proliferates.

"Cisco has acquired Astrix Security, a roughly five-year-old Israeli cybersecurity startup that helps enterprises monitor and control 'non-human identities' such as AI agents, API keys, and automated systems to prevent breaches. The deal is valued at about $400 million."


Clean Energy Infrastructure Is IPO-Ready and Commanding Premium Valuations

Fervo Energy's IPO valuation more than doubled from earlier in the year, signaling strong public market appetite for credible clean energy infrastructure plays.

"Fervo Energy…is seeking to raise more than $1.3 billion in an IPO that could value the company at about $6.5 billion, more than double the valuation it was targeting earlier this year."


2. Contrarian Perspectives

GameStop's eBay Bid Looks Like a Meme Move, Not a Strategic One

The market and media are treating the GameStop/eBay bid as a serious M&A story, but the article makes clear it lacks coherent strategic logic — and the CEO couldn't explain it on live television. A $56B unsolicited cash-and-stock offer from a company with GameStop's fundamentals, backed by up to $20B in debt, raises serious questions about whether this is shareholder value creation or narrative manipulation.

"Cohen could not explain the deal when he was asked about it on CNBC's Squawk Box."

The implication: this may be a meme-stock maneuver designed to move GameStop's stock price rather than a bona fide acquisition strategy — a pattern worth watching for regulatory and market signal distortion.


Prediction Markets Aren't Democratic — They're Dominated by Algorithmic Traders

The popular framing of prediction markets like Polymarket as "wisdom of the crowd" instruments is undermined by data showing extreme concentration of profits among a tiny elite of algo-driven traders.

"A Wall Street Journal analysis finds that 67% of profits on Polymarket go to just 0.1% of accounts, as sophisticated traders using data and algorithms consistently outperform casual users."

For investors, this means Polymarket prices likely reflect the views of a narrow, technically sophisticated cohort — not broad market consensus.


Offshore AI Computing Is Becoming a Real Infrastructure Thesis

Panthalassa's $140M raise — led by Thiel, Doerr, and Founders Fund — for ocean-based AI computing and wave power generation suggests serious investors are betting on geographically distributed, off-grid compute infrastructure as a legitimate alternative to land-based data centers. This is well outside mainstream AI infrastructure discourse.

"Panthalassa…builds autonomous ocean-based systems to generate wave power and run AI computing at sea, raised $140 million in a Series B round led by Peter Thiel, with John Doerr, TIME Ventures, SciFi Ventures…Founders Fund [and others] also piling on."


3. Companies Identified

CompanyDescriptionWhy MentionedQuote
SierraAI-powered enterprise customer experience platformRaised $950M at $15B+ valuation; rapid ARR growth from $100M to $150M in ~90 days"The company says it started with just four design partners a couple of years ago. Today it claims to have more than 40% of the Fortune 50 as customers."
GameStopLegacy video game retailer turned meme stockMade an unsolicited, unexplained $56B bid for eBay"Cohen could not explain the deal when he was asked about it on CNBC's Squawk Box."
eBayE-commerce marketplaceTarget of GameStop's unsolicited $56B acquisition offer"GameStop has made an unsolicited $56 billion bid to acquire eBay, offering $125 per share in a mix of cash and stock."
AmazonE-commerce and cloud giantLaunching Amazon Supply Chain Services to compete directly with UPS and FedEx"Amazon is opening its logistics network to all businesses through a new service called Amazon Supply Chain Services."
AnthropicAI safety and LLM companyForming a ~$1.5B enterprise deployment venture with major PE/financial backers"Anthropic is forming a roughly $1.5 billion venture, with investors including Blackstone, Hellman & Friedman, and Goldman Sachs."
OpenAIAI foundation model companyRaising $4B+ for The Deployment Company to accelerate enterprise adoption"OpenAI has raised more than $4 billion for a new venture called The Deployment Company backed by 19 investors."
PanthalassaOcean-based wave power and AI computing infrastructureRaised $140M Series B from high-profile investors for offshore compute"Builds autonomous ocean-based systems to generate wave power and run AI computing at sea."
CerebrasAI chipmakerTargeting $26.6B valuation in U.S. IPO, raising ~$3.5B"Targeting a valuation of up to $26.6 billion in its U.S. IPO and plans to raise about $3.5 billion."
Fervo EnergyEnhanced geothermal power developerIPO targeting $6.5B valuation — more than double earlier target"More than double the valuation it was targeting earlier this year."
Astrix SecurityIsraeli cybersecurity startup focused on non-human identitiesAcquired by Cisco for ~$400M"Helps enterprises monitor and control 'non-human identities' such as AI agents, API keys, and automated systems."
SunoAI music generation startupReportedly closing Series D at $5B+, more than 2x its November valuation"Reportedly weeks away from closing a Series D round at a $5+ billion valuation, more than twice the valuation of a round it raised in November."
LinkerbotDexterous robotic hands for humanoid robotsSeries B+ at $3B valuation"Develops highly dexterous robotic hands for humanoid robots."
PolymarketPrediction market platformCited as example of algo-driven profit concentration"67% of profits on Polymarket go to just 0.1% of accounts."
OusterLidar sensor companyUnveiled color lidar combining camera-quality imagery with depth sensing"Aims to replace traditional camera-and-lidar setups in robotics and autonomous vehicles."
SAPEnterprise software giantAcquiring Dremio and Prior Labs; investing €1B in Prior Labs"SAP also announced plans to invest €1 billion in Prior Labs over four years."
DremioOpen data lakehouse softwareAcquired by SAP"Builds open data lakehouse software."
Prior LabsEuropean AI research startup for structured dataAcquired by SAP with €1B investment commitment"A young European AI research startup focused on building models for structured data."
Haun VenturesCrypto and fintech-focused VC firmRaised $1B across new funds"Raised $1 billion across new early- and late-stage funds to invest in crypto and startups at the intersection of financial services, AI, and alternative assets."

4. People Identified

PersonDescriptionWhy MentionedQuote
Bret TaylorCEO of Sierra; Chairman of OpenAI; former co-CEO of SalesforceLeading Sierra's $950M raise and $15B+ valuation"Taylor…has said that the best-case outcome for agentic AI is lower costs and higher revenue for clients, but before those returns materialize, the ramp-up phase can be pricey."
Ryan CohenCEO of GameStopMade an unsolicited $56B bid for eBay but could not explain the rationale publicly"Cohen could not explain the deal when he was asked about it on CNBC's Squawk Box."
Praveen Neppalli NagaCTO of UberDisclosed Uber's agentic AI budget overrun while noting early positive results"Uber 'blew through our [AI] budget' soon after opening the door to agentic AI tools late last year."
Greg BrockmanPresident and co-founder of OpenAICentral figure in OpenAI vs. Musk trial; holds ~$30B stake in OpenAI"Musk's lawyers pressed president Greg Brockman over his $30 billion OpenAI stake, arguing it undercuts the company's claim to prioritize AI safety over profit."
Elon MuskCEO of Tesla and SpaceX; founder of xAIDefendant in OpenAI lawsuit; settled SEC disclosure case for $1.5M"By the end of this week, you and Sam [Altman] will be the most hated men in America."
Sam AltmanCEO of OpenAIReferenced in Musk's alleged threat during legal disputeReferenced alongside Brockman in Musk's alleged text message threat.
William SavittWachtell litigatorLeading Sam Altman's defense against Musk; previously won against Musk on Twitter acquisition"A former cab driver and rock band singer who is leading Sam Altman's defense against Elon Musk after previously scoring a victory against Musk over his attempt to back out of acquiring Twitter."
Jack ClarkAnthropic co-founderIssued a stark warning about AI timelines"Anthropic co-founder Jack Clark believes that there is a good chance we only have about two years."
Jeff BezosAmazon founderSelling his $500M superyacht due to operational difficulties"Partly because its sheer size makes it difficult to dock and operate."
Peter ThielFounders Fund; prominent tech investorLed Panthalassa's $140M Series BListed as lead investor alongside Doerr and Founders Fund.
John DoerrKleiner Perkins; prominent investorParticipated in Panthalassa's $140M raiseListed alongside Peter Thiel as a key backer of Panthalassa.
Dylan FieldCEO of FigmaParticipated in Panthalassa's $140M raiseListed among Panthalassa investors.

5. Operating Insights

Budget AI Separately and Expect Overruns Before You See ROI

Enterprise operators deploying agentic AI should plan for a distinct "ramp-up" budget that is separate from ongoing operational costs. Uber's experience is a real-world signal that even well-resourced companies hit budget ceilings quickly when agentic tools are activated at scale — but the results can follow.

"Uber 'blew through our [AI] budget' soon after opening the door to agentic AI tools late last year. He also said the company is starting to see meaningful results."


Design Partner Strategy Still Works at Scale — If You Move Fast to Enterprise

Sierra's trajectory from four design partners to 40%+ of the Fortune 50 in roughly two years demonstrates that a tightly curated early customer cohort can become a credible enterprise reference base with remarkable speed — if the product solves a measurable, high-frequency workflow.

"The company says it started with just four design partners a couple of years ago. Today it claims to have more than 40% of the Fortune 50 as customers, and says the agents running on its platform are handling billions of interactions, from refinancing mortgages to processing insurance claims, managing returns, and powering nonprofit fundraising campaigns."


Non-Human Identity Governance Is Now a Board-Level Risk Item

With Cisco paying ~$400M for Astrix, operators should treat governance of AI agents, API keys, and automated systems as a security and compliance priority — not a future roadmap item.

"Cisco has acquired Astrix Security…that helps enterprises monitor and control 'non-human identities' such as AI agents, API keys, and automated systems to prevent breaches."


6. Overlooked Insights

State Health Insurance Marketplaces Have Been Leaking Sensitive Data to Ad Tech for Years

A Bloomberg investigation found that misconfigured tracking pixels on government health insurance sites have been sharing citizenship status, race, and incarceration data with ad tech companies. This is a significant regulatory and liability exposure for companies operating in govtech or healthtech adjacent spaces — and may trigger new compliance requirements.

"Most U.S. state-run health insurance marketplaces shared sensitive application data — including citizenship, race, and incarceration status — with ad tech companies due to misconfigured tracking pixels."


"Emotion AI" Is Already Deployed in Mainstream Enterprise Operations

While most investor attention is on generative and agentic AI, a quieter category — emotion AI for workforce monitoring — is already in production in customer service, logistics, and retail. The regulatory and reputational risk for companies deploying these tools is rising, and the backlash may create openings for privacy-forward alternatives.

"Companies in sectors like customer service, logistics, and retail are increasingly using 'emotion AI' tools to monitor workers' tone, facial expressions, and behavior to assess agreeability and productivity even as critics say the technology is unreliable and invasive."