May 25, 2026 · 57m · big-technology

Is OpenAI Ready To IPO?, The Datacenters in Space Myth, The Kids Boo AI

Ranjan Roy · 27m spoken Alex Kantrowitz · 24m spoken
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Alex Kantrowitz and Ranjan Roy analyze the financial pressures pushing OpenAI and Anthropic toward public market listings, critique the viability of space-based data centers, and examine mounting cultural backlash against AI leaders.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 47.4% of the talking time here. How this is scored →

Alex as informed peer 6.1 Guest teaching 3.1 Guest disagreement 2.6 Alex pushing back 3.6
05100:0015:0030:0045:000:00–7:37 · Alex as informed peer 4/10 Episode Preview and Breaking Tech Headlines Alex cites reporting from The Information on OpenAI's -122% operating margin, but explicitly defers to Ranjan's Wall Street background to explain why operating losses matter despite excluding stock-based compensation. Ranjan explains line-item mechanics and pushes back on the conventional wisdom that AI companies can flip to profitability like traditional SaaS.7:37–14:07 · Alex as informed peer 7/10 The Competitive IPO Race Between OpenAI and Anthropic Alex articulates a detailed thesis explaining why OpenAI is rushing to IPO before Anthropic, connecting Dario Amodei's comments, infrastructure buildouts, and the drying up of Gulf state funding. Ranjan fully agrees with Alex's macro framing.14:08–21:27 · Alex as informed peer 6/10 Anthropic Projected Profits and SpaceX Accounting Deals Ranjan reveals a clause from the SpaceX S-1 showing Anthropic secured a reduced-fee deal for May/June 2026, arguing Anthropic engineered temporary profitability to leak to the press ahead of an S-1. Alex pushes back vigorously saying he doesn't buy that showing artificial profit benefits Anthropic long-term, though he admits he has no answer for the specific May/June timing.21:27–28:36 · Alex as informed peer 7/10 Growth Plateaus, Token Costs, and Enterprise Pullbacks Alex presents multiple concrete data points including ChatGPT's active user dip, Google's 3.2 quadrillion token processing stats, and Microsoft revoking Claude Code licenses due to unchecked token consumption. Ranjan elaborates from his industry perspective on enterprises moving toward model routing to rein in costs.28:37–36:46 · Alex as informed peer 5/10 Assessing IPO Readiness and Public Market Transparency Both host and guest align in answering whether OpenAI and Anthropic are ready to go public, concluding they should file if only to bring audited financial transparency to the broader tech sector.36:47–45:05 · Alex as informed peer 7/10 SpaceX S-1 Disclosures and the Orbital Data Center Debate Alex tears into SpaceX's $28.5T addressable market projection and mocks orbital data centers as an operational fantasy where broken servers would require astronaut technicians. When Ranjan playfully defends space data centers, Alex immediately shuts down the notion.45:06–57:06 · Alex as informed peer 7/10 College Commencement Boos and AI's Deepening PR Crisis Alex cites verbatim leaks from Mark Zuckerberg's internal Meta all-hands regarding keystroke tracking, alongside Marc Andreessen's podcast rhetoric, to diagnose tech's deepening public relations crisis among college grads. Ranjan contributes satirical alternatives for corporate communication.0:00–7:37 · Guest teaching 5/10 Episode Preview and Breaking Tech Headlines Alex cites reporting from The Information on OpenAI's -122% operating margin, but explicitly defers to Ranjan's Wall Street background to explain why operating losses matter despite excluding stock-based compensation. Ranjan explains line-item mechanics and pushes back on the conventional wisdom that AI companies can flip to profitability like traditional SaaS.7:37–14:07 · Guest teaching 2/10 The Competitive IPO Race Between OpenAI and Anthropic Alex articulates a detailed thesis explaining why OpenAI is rushing to IPO before Anthropic, connecting Dario Amodei's comments, infrastructure buildouts, and the drying up of Gulf state funding. Ranjan fully agrees with Alex's macro framing.14:08–21:27 · Guest teaching 6/10 Anthropic Projected Profits and SpaceX Accounting Deals Ranjan reveals a clause from the SpaceX S-1 showing Anthropic secured a reduced-fee deal for May/June 2026, arguing Anthropic engineered temporary profitability to leak to the press ahead of an S-1. Alex pushes back vigorously saying he doesn't buy that showing artificial profit benefits Anthropic long-term, though he admits he has no answer for the specific May/June timing.21:27–28:36 · Guest teaching 3/10 Growth Plateaus, Token Costs, and Enterprise Pullbacks Alex presents multiple concrete data points including ChatGPT's active user dip, Google's 3.2 quadrillion token processing stats, and Microsoft revoking Claude Code licenses due to unchecked token consumption. Ranjan elaborates from his industry perspective on enterprises moving toward model routing to rein in costs.28:37–36:46 · Guest teaching 1/10 Assessing IPO Readiness and Public Market Transparency Both host and guest align in answering whether OpenAI and Anthropic are ready to go public, concluding they should file if only to bring audited financial transparency to the broader tech sector.36:47–45:05 · Guest teaching 3/10 SpaceX S-1 Disclosures and the Orbital Data Center Debate Alex tears into SpaceX's $28.5T addressable market projection and mocks orbital data centers as an operational fantasy where broken servers would require astronaut technicians. When Ranjan playfully defends space data centers, Alex immediately shuts down the notion.45:06–57:06 · Guest teaching 2/10 College Commencement Boos and AI's Deepening PR Crisis Alex cites verbatim leaks from Mark Zuckerberg's internal Meta all-hands regarding keystroke tracking, alongside Marc Andreessen's podcast rhetoric, to diagnose tech's deepening public relations crisis among college grads. Ranjan contributes satirical alternatives for corporate communication.0:00–7:37 · Guest disagreement 3/10 Episode Preview and Breaking Tech Headlines Alex cites reporting from The Information on OpenAI's -122% operating margin, but explicitly defers to Ranjan's Wall Street background to explain why operating losses matter despite excluding stock-based compensation. Ranjan explains line-item mechanics and pushes back on the conventional wisdom that AI companies can flip to profitability like traditional SaaS.7:37–14:07 · Guest disagreement 1/10 The Competitive IPO Race Between OpenAI and Anthropic Alex articulates a detailed thesis explaining why OpenAI is rushing to IPO before Anthropic, connecting Dario Amodei's comments, infrastructure buildouts, and the drying up of Gulf state funding. Ranjan fully agrees with Alex's macro framing.14:08–21:27 · Guest disagreement 5/10 Anthropic Projected Profits and SpaceX Accounting Deals Ranjan reveals a clause from the SpaceX S-1 showing Anthropic secured a reduced-fee deal for May/June 2026, arguing Anthropic engineered temporary profitability to leak to the press ahead of an S-1. Alex pushes back vigorously saying he doesn't buy that showing artificial profit benefits Anthropic long-term, though he admits he has no answer for the specific May/June timing.21:27–28:36 · Guest disagreement 2/10 Growth Plateaus, Token Costs, and Enterprise Pullbacks Alex presents multiple concrete data points including ChatGPT's active user dip, Google's 3.2 quadrillion token processing stats, and Microsoft revoking Claude Code licenses due to unchecked token consumption. Ranjan elaborates from his industry perspective on enterprises moving toward model routing to rein in costs.28:37–36:46 · Guest disagreement 1/10 Assessing IPO Readiness and Public Market Transparency Both host and guest align in answering whether OpenAI and Anthropic are ready to go public, concluding they should file if only to bring audited financial transparency to the broader tech sector.36:47–45:05 · Guest disagreement 4/10 SpaceX S-1 Disclosures and the Orbital Data Center Debate Alex tears into SpaceX's $28.5T addressable market projection and mocks orbital data centers as an operational fantasy where broken servers would require astronaut technicians. When Ranjan playfully defends space data centers, Alex immediately shuts down the notion.45:06–57:06 · Guest disagreement 2/10 College Commencement Boos and AI's Deepening PR Crisis Alex cites verbatim leaks from Mark Zuckerberg's internal Meta all-hands regarding keystroke tracking, alongside Marc Andreessen's podcast rhetoric, to diagnose tech's deepening public relations crisis among college grads. Ranjan contributes satirical alternatives for corporate communication.0:00–7:37 · Alex pushing back 3/10 Episode Preview and Breaking Tech Headlines Alex cites reporting from The Information on OpenAI's -122% operating margin, but explicitly defers to Ranjan's Wall Street background to explain why operating losses matter despite excluding stock-based compensation. Ranjan explains line-item mechanics and pushes back on the conventional wisdom that AI companies can flip to profitability like traditional SaaS.7:37–14:07 · Alex pushing back 2/10 The Competitive IPO Race Between OpenAI and Anthropic Alex articulates a detailed thesis explaining why OpenAI is rushing to IPO before Anthropic, connecting Dario Amodei's comments, infrastructure buildouts, and the drying up of Gulf state funding. Ranjan fully agrees with Alex's macro framing.14:08–21:27 · Alex pushing back 6/10 Anthropic Projected Profits and SpaceX Accounting Deals Ranjan reveals a clause from the SpaceX S-1 showing Anthropic secured a reduced-fee deal for May/June 2026, arguing Anthropic engineered temporary profitability to leak to the press ahead of an S-1. Alex pushes back vigorously saying he doesn't buy that showing artificial profit benefits Anthropic long-term, though he admits he has no answer for the specific May/June timing.21:27–28:36 · Alex pushing back 3/10 Growth Plateaus, Token Costs, and Enterprise Pullbacks Alex presents multiple concrete data points including ChatGPT's active user dip, Google's 3.2 quadrillion token processing stats, and Microsoft revoking Claude Code licenses due to unchecked token consumption. Ranjan elaborates from his industry perspective on enterprises moving toward model routing to rein in costs.28:37–36:46 · Alex pushing back 2/10 Assessing IPO Readiness and Public Market Transparency Both host and guest align in answering whether OpenAI and Anthropic are ready to go public, concluding they should file if only to bring audited financial transparency to the broader tech sector.36:47–45:05 · Alex pushing back 7/10 SpaceX S-1 Disclosures and the Orbital Data Center Debate Alex tears into SpaceX's $28.5T addressable market projection and mocks orbital data centers as an operational fantasy where broken servers would require astronaut technicians. When Ranjan playfully defends space data centers, Alex immediately shuts down the notion.45:06–57:06 · Alex pushing back 2/10 College Commencement Boos and AI's Deepening PR Crisis Alex cites verbatim leaks from Mark Zuckerberg's internal Meta all-hands regarding keystroke tracking, alongside Marc Andreessen's podcast rhetoric, to diagnose tech's deepening public relations crisis among college grads. Ranjan contributes satirical alternatives for corporate communication.

speaking balance: gold is Alex, purple is the guest (3 minute bins)

0:00 · Alex 81.2% · guest 18.8%0:00 · Alex 81.2% · guest 18.8%3:00 · Alex 34.8% · guest 65.2%3:00 · Alex 34.8% · guest 65.2%6:00 · Alex 52.5% · guest 47.5%6:00 · Alex 52.5% · guest 47.5%9:00 · Alex 29.8% · guest 70.2%9:00 · Alex 29.8% · guest 70.2%12:00 · Alex 57.6% · guest 42.4%12:00 · Alex 57.6% · guest 42.4%15:00 · Alex 6% · guest 94%15:00 · Alex 6% · guest 94%18:00 · Alex 41.8% · guest 58.2%18:00 · Alex 41.8% · guest 58.2%21:00 · Alex 65.4% · guest 34.6%21:00 · Alex 65.4% · guest 34.6%24:00 · Alex 35.9% · guest 64.1%24:00 · Alex 35.9% · guest 64.1%27:00 · Alex 50.3% · guest 49.7%27:00 · Alex 50.3% · guest 49.7%30:00 · Alex 11.3% · guest 88.7%30:00 · Alex 11.3% · guest 88.7%33:00 · Alex 52.1% · guest 47.9%33:00 · Alex 52.1% · guest 47.9%36:00 · Alex 71.1% · guest 28.9%36:00 · Alex 71.1% · guest 28.9%39:00 · Alex 63.4% · guest 36.6%39:00 · Alex 63.4% · guest 36.6%42:00 · Alex 50.3% · guest 49.7%42:00 · Alex 50.3% · guest 49.7%45:00 · Alex 49.4% · guest 50.6%45:00 · Alex 49.4% · guest 50.6%48:00 · Alex 49.6% · guest 50.4%48:00 · Alex 49.6% · guest 50.4%51:00 · Alex 50.7% · guest 49.3%51:00 · Alex 50.7% · guest 49.3%54:00 · Alex 46.9% · guest 53.1%54:00 · Alex 46.9% · guest 53.1%57:00 · Alex 55.4% · guest 44.6%57:00 · Alex 55.4% · guest 44.6%
Sharpest disagreement ▶ 18:38 Ranjan interrogates Alex on Anthropic's SpaceX deal

Ranjan repeatedly interrupts and challenges Alex to explain why SpaceX gave Anthropic a fee reduction exclusively in May and June 2026 if not to manufacture a profitable quarter.

Hardest push from Alex ▶ 42:09 Alex rejects orbital data center viability

Alex forcefully rebuffs Ranjan's defense of space data centers, telling him not to be ridiculous and questioning what planet he is living on.

Biggest teaching moment ▶ 16:20 Ranjan exposes Anthropic's SpaceX S-1 sweetheart clause

Ranjan brings up obscure disclosures from the SpaceX S-1 showing Anthropic's monthly spend is temporarily discounted, educating Alex on how Anthropic's reported profitability was likely engineered.

Alex holds their own ▶ 38:40 Alex deconstructs SpaceX's $28.5T TAM claim

Alex systematically dismantles SpaceX's S-1 filing, citing specific breakdown numbers to show that 93% of the claimed space TAM is actually enterprise AI software where Grok severely lags competitors.

the scores for every segment, with the reasoning behind each
ChapterTopicAlex as informed peerGuest teachingGuest disagreementAlex pushing backWhy
Episode Preview and Breaking Tech Headlines 4533 Alex cites reporting from The Information on OpenAI's -122% operating margin, but explicitly defers to Ranjan's Wall Street background to explain why operating losses matter despite excluding stock-based compensation. Ranjan explains line-item mechanics and pushes back on the conventional wisdom that AI companies can flip to profitability like traditional SaaS.
The Competitive IPO Race Between OpenAI and Anthropic 7212 Alex articulates a detailed thesis explaining why OpenAI is rushing to IPO before Anthropic, connecting Dario Amodei's comments, infrastructure buildouts, and the drying up of Gulf state funding. Ranjan fully agrees with Alex's macro framing.
Anthropic Projected Profits and SpaceX Accounting Deals 6656 Ranjan reveals a clause from the SpaceX S-1 showing Anthropic secured a reduced-fee deal for May/June 2026, arguing Anthropic engineered temporary profitability to leak to the press ahead of an S-1. Alex pushes back vigorously saying he doesn't buy that showing artificial profit benefits Anthropic long-term, though he admits he has no answer for the specific May/June timing.
Growth Plateaus, Token Costs, and Enterprise Pullbacks 7323 Alex presents multiple concrete data points including ChatGPT's active user dip, Google's 3.2 quadrillion token processing stats, and Microsoft revoking Claude Code licenses due to unchecked token consumption. Ranjan elaborates from his industry perspective on enterprises moving toward model routing to rein in costs.
Assessing IPO Readiness and Public Market Transparency 5112 Both host and guest align in answering whether OpenAI and Anthropic are ready to go public, concluding they should file if only to bring audited financial transparency to the broader tech sector.
SpaceX S-1 Disclosures and the Orbital Data Center Debate 7347 Alex tears into SpaceX's $28.5T addressable market projection and mocks orbital data centers as an operational fantasy where broken servers would require astronaut technicians. When Ranjan playfully defends space data centers, Alex immediately shuts down the notion.
College Commencement Boos and AI's Deepening PR Crisis 7222 Alex cites verbatim leaks from Mark Zuckerberg's internal Meta all-hands regarding keystroke tracking, alongside Marc Andreessen's podcast rhetoric, to diagnose tech's deepening public relations crisis among college grads. Ranjan contributes satirical alternatives for corporate communication.

Statements from this episode (23)

Assertion Contradicted
Kantrowitz: SpaceX filed for an IPO this week
“SpaceX, of course, filed to go public this week.”
Alex Kantrowitz May 25, 2026 ▶ 0:33
Assertion Supported
Kantrowitz: Speakers at three commencements were booed after mentioning AI
“We had three commencements so far where the speakers have mentioned AI and then actually seemed somewhat baffled by people booing them.”
Alex Kantrowitz May 25, 2026 ▶ 1:11
Prediction Not checkable as stated
Kantrowitz: OpenAI and Anthropic are gearing up to file for IPOs
“OpenAI and Anthropic as both gear up towards filing for IPOs. Maybe even this year we could potentially even see the paperwork for OpenAI come through as you and I record today, Ranjan.”
Alex Kantrowitz May 25, 2026 ▶ 1:23
Assertion Supported
Kantrowitz: OpenAI generated $5.7B in Q1 revenue, beating Anthropic by $1B
“OpenAI generated about 5.7 billion in revenue in Q-one. Nearly one billion more than archrival Anthropic generated in the same period.”
Alex Kantrowitz May 25, 2026 ▶ 1:57
Assertion Supported
Kantrowitz: OpenAI reported a -122% adjusted operating margin in Q1
“OpenAI told investors that its adjusted operating income margin was -122% in the first quarter. That means for every dollar of revenue the company generated, it lost one dollar and 22 cents, even after excluding some large items such as stock based compensatio…”
Alex Kantrowitz May 25, 2026 ▶ 2:08
Insight
Roy: AI economics are more akin to industrials than software
“The economics of a general or an AI company are just fundamentally different than software. That like, it's more akin to industrial companies or something, because you're paying for The compute costs. So the resources in can scale linearly or somewhat linearly…”
Ranjan Roy May 25, 2026 ▶ 6:54
Opinion
Kantrowitz: OpenAI's IPO push is driven by Anthropic's rapid revenue growth
“I think it is entirely a result of Anthropik's success. So you have a couple of curves that are running in parallel right now. So you have OpenAI, which made more money than Anthropik, but Anthropik's revenue and user growth, it seems like has, well, revenue i…”
Alex Kantrowitz May 25, 2026 ▶ 7:53
Assertion Supported
Kantrowitz: WSJ reports Anthropic will generate $10.9B in Q2, reaching profitability
“So they're going to make 10.9 billion In the second quarter, and the journal says it's an explosive rate of growth that will help it turn an operating profit for the first time.”
Alex Kantrowitz May 25, 2026 ▶ 8:17
Opinion
Roy: SpaceX's S-1 filing positions it as an AI company, not space
“But, so they have already filed their S-one, and have positioned themselves squarely in the AI camp. Like, this is not a space company anymore. This is an AI company.”
Ranjan Roy May 25, 2026 ▶ 10:09
Assertion Supported
Roy: SpaceX is targeting a $40B to $80B IPO raise
“Again, like SpaceX is targeting a raise between 40 and eighty billion dollars.”
Ranjan Roy May 25, 2026 ▶ 13:43
Insight
Kantrowitz: AI lab profitability indicates underbuilt compute infrastructure
“If you're trying to Hit that Goldilocks zone of building out enough to keep growing without mortgaging the company or without going bankrupt, you actually underbuilt if you're profitable.”
Alex Kantrowitz May 25, 2026 ▶ 14:13
Opinion
Roy: Anthropic's projected $10.9B Q2 revenue is overly ambitious
“There's been a lot of growth, but we all know Codex show a five point show up from open AI recently. I've seen endless chatter around people actually switching over from anthropic. So the idea that it's going to be a straight line or not even straight line, I'…”
Ranjan Roy May 25, 2026 ▶ 14:59
Assertion Supported
Roy: SpaceX S-1 shows Anthropic committed to $1.25B monthly spend
“In the SpaceX S one document, they talk about how Anthropic has agreed. And this is one of the big, like revenue boosters for them. To spend 1.25 billion dollars per month through May 2029. But they explicitly say in May and June, 2026, it is at a reduced fee.”
Ranjan Roy May 25, 2026 ▶ 16:01
Assertion Supported
Kantrowitz: OpenAI Averaged 905M WAU, Missing 1B Year-End Target
“OpenAI's weekly active users for the quarter averaged about nine hundred five million users. Although the company hit about nine hundred twenty million weekly active users in February, the lower average figure for the quarter implies that usage during the rest…”
Alex Kantrowitz May 25, 2026 ▶ 22:03
Assertion Supported
Kantrowitz: Google Token Volume Grew to 3.2 Quadrillion Monthly
“Google gave this week they're now processing three quadrillion tokens. It's gone. It's at 9.7 trillion to 3.2 quadrillion per month in two years, according to Sundar Pichai”
Alex Kantrowitz May 25, 2026 ▶ 26:10
Assertion Supported
Kantrowitz: Microsoft Plans to Cancel Claude Code Licenses for Copilot CLI
“Microsoft, according to the verge, Starts canceling cloud code license licenses. Microsoft first started opening up access to cloud code in December. It was part of an effort to get product manager, project managers, designers, and other employees to experimen…”
Alex Kantrowitz May 25, 2026 ▶ 27:39
Prediction Not checkable as stated
Roy: AI will shift to multi-model routing over single dominant models
“Interoperability model routing based on request being model provider agnostic on the foundation model side is where I see this going. It's not gonna be one, and I mean, we've talked about this for a long time, one model to rule them all, systems that can route”
Ranjan Roy May 25, 2026 ▶ 30:29
Prediction Not checkable as stated
Roy: Claude will never repeat its previous six-month revenue growth
“The graph of revenue growth for Claude for the last six months, we will never see again. It was just something where no one was checking anything.”
Ranjan Roy May 25, 2026 ▶ 31:20
Assertion Supported
Kantrowitz: SpaceX lost $4.28B on $4.69B Q1 revenue
“SpaceX had a net loss. 4.28 billion on revenue of 4.69 billion for the first quarter compared with a net loss of five hundred twenty eight million on revenue of about four billion a year earlier.”
Alex Kantrowitz May 25, 2026 ▶ 37:15
Assertion Supported
Kantrowitz: xAI rented Colossus 1 compute cluster to Anthropic
“You just rented your AI warehouse Colossus One to Anthropic.”
Alex Kantrowitz May 25, 2026 ▶ 40:43
Assertion Supported
Kantrowitz: Blue Origin filed FCC plans for 51,600 orbital data centers
“Blue Origin, which is his space company, recently submitted plans to the FCC to send 51,600 data center satellites into low Earth orbit as part of an initiative dubbed Project Sunrise.”
Alex Kantrowitz May 25, 2026 ▶ 42:47
Assertion Supported
Kantrowitz: Eric Schmidt was booed at University of Arizona commencement
“Eric Schmidt, the former CEO of Google, was booed this week at the University of Arizona's graduation ceremony.”
Alex Kantrowitz May 25, 2026 ▶ 45:07
Prediction Not checkable as stated
Kantrowitz: AI communication failures will cause political moratoriums and data center blocks
“Like, you're not, the botching of the storytelling on this front, and you know, we talk a lot about comms, so fine, get the criticism, but like, this is gonna have real implications. You're gonna have candidates talking about kill switches, moratoriums, you're…”
Alex Kantrowitz May 25, 2026 ▶ 52:37
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