Jul 23, 2026 · 1h 27m · news

Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal

Rory O'Driscoll · 46m spoken Jason Lemkin · 23m spoken Harry Stebbings · 9m spoken

Clips from this episode (5)

Short vertical cuts produced from the tape, captions burned in. Where a cut lands on a statement from the ledger, its card says so.

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the statementO'Driscoll: Chinese AI models rely on distillation illegal in the USPartly supportedRory O'Driscollread it →
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the statementLemkin: the AI application layer era is not here yetJason Lemkinread it →
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the statementO'Driscoll: 20x-revenue AI valuations demand Microsoft-level 40% marginsRory O'Driscollread it →
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the statementO'Driscoll: tranche structures price away the growth-round excess return, and that is how the trend endsRory O'Driscollread it →
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the statementO'Driscoll: SPACs take venture-grade risk public while the best venture assets stay privateRory O'Driscollread it →
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▶ Watch on YouTube →

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of the 20VC podcast, host Harry Stebbings and venture capitalists Rory O'Driscoll and Jason Lemkin discuss the impact of Chinese open-weight AI models, AI middleware and routing economics, Stripe's acquisition bid for PayPal, and late-stage venture capital dynamics.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 11.8% of the talking time here. How this is scored →

Harry as informed peer 3.4 Guest teaching 3.1 Guest disagreement 2.3 Harry pushing back 2.6
05100:0020:0040:001:00:001:20:001:09–9:10 · Harry as informed peer 2/10 Impact of Chinese Open-Weight AI Models Harry introduces the topic of Chinese open-weight models Kimi and Qwen catching up to frontier Western models. The guests lead the conversation, discussing evaluation accuracy and the political fallout from OpenAI policy staff tweets.9:10–19:35 · Harry as informed peer 3/10 AI Model Policy, Regulation, and Exfiltration Risks Harry challenges Jason on data export fears by pointing out that CIOs are told on-prem deployments remove backdoor risks. Jason pushes back forcefully, arguing that complex LLM behavior cannot be fully audited or trusted regardless of on-prem hosting.19:35–31:27 · Harry as informed peer 3/10 OpenRouter M&A Rumors and Model Routing Infrastructure When Harry asks if a board should sell OpenRouter for $5B to $6B, Jason calls out the question as a classic VC-centric mindset. Jason educates the host on how founder economics differ from investor fund returns.31:27–39:25 · Harry as informed peer 4/10 Fireworks AI Funding and Infrastructure vs Application Value Harry demonstrates strong topic knowledge by presenting the detailed deal terms and operational metrics for Fireworks AI. The guests agree and elaborate on inference unit economics and capex requirements.39:25–52:11 · Harry as informed peer 3/10 Custom Micro-Models, Data Labeling, and Model Economics The conversation moves to fine-tuning, domain-specific micro-models, and data labeling economics. Jason shares hands-on experience building an agentic app and explains how domain expert labeling vastly outperforms generic foundation models.52:11–1:04:18 · Harry as informed peer 3/10 Stripe's Strategic Acquisition Bid for PayPal Harry prompts the guests regarding rumors of Stripe making an acquisition bid for PayPal alongside Advent. Rory and Jason explain public company board dynamics, Delaware law fiduciary duties, and the standard M&A premium negotiation dance.1:04:18–1:18:09 · Harry as informed peer 6/10 Venture Capital Market Dynamics and Tranche Financing Structures Harry takes an active expert role, highlighting a sharp market disconnect where early-stage Series A valuations command 50x-100x revenue multiples while scaled growth companies sell for 10x forward revenue. He defends the risk-adjusted value of growth stage investing.1:18:09–1:27:29 · Harry as informed peer 3/10 Private vs Public Tech Markets and Hardware Supply Chains The panel discusses private versus public tech market inversions, highlighting how pre-revenue speculative companies SPAC while cash-flow monster companies stay private. Rory explains the contrasting dynamics between collaborative chip supply chains and predatory DRAM memory pricing.1:09–9:10 · Guest teaching 2/10 Impact of Chinese Open-Weight AI Models Harry introduces the topic of Chinese open-weight models Kimi and Qwen catching up to frontier Western models. The guests lead the conversation, discussing evaluation accuracy and the political fallout from OpenAI policy staff tweets.9:10–19:35 · Guest teaching 4/10 AI Model Policy, Regulation, and Exfiltration Risks Harry challenges Jason on data export fears by pointing out that CIOs are told on-prem deployments remove backdoor risks. Jason pushes back forcefully, arguing that complex LLM behavior cannot be fully audited or trusted regardless of on-prem hosting.19:35–31:27 · Guest teaching 6/10 OpenRouter M&A Rumors and Model Routing Infrastructure When Harry asks if a board should sell OpenRouter for $5B to $6B, Jason calls out the question as a classic VC-centric mindset. Jason educates the host on how founder economics differ from investor fund returns.31:27–39:25 · Guest teaching 2/10 Fireworks AI Funding and Infrastructure vs Application Value Harry demonstrates strong topic knowledge by presenting the detailed deal terms and operational metrics for Fireworks AI. The guests agree and elaborate on inference unit economics and capex requirements.39:25–52:11 · Guest teaching 2/10 Custom Micro-Models, Data Labeling, and Model Economics The conversation moves to fine-tuning, domain-specific micro-models, and data labeling economics. Jason shares hands-on experience building an agentic app and explains how domain expert labeling vastly outperforms generic foundation models.52:11–1:04:18 · Guest teaching 3/10 Stripe's Strategic Acquisition Bid for PayPal Harry prompts the guests regarding rumors of Stripe making an acquisition bid for PayPal alongside Advent. Rory and Jason explain public company board dynamics, Delaware law fiduciary duties, and the standard M&A premium negotiation dance.1:04:18–1:18:09 · Guest teaching 3/10 Venture Capital Market Dynamics and Tranche Financing Structures Harry takes an active expert role, highlighting a sharp market disconnect where early-stage Series A valuations command 50x-100x revenue multiples while scaled growth companies sell for 10x forward revenue. He defends the risk-adjusted value of growth stage investing.1:18:09–1:27:29 · Guest teaching 3/10 Private vs Public Tech Markets and Hardware Supply Chains The panel discusses private versus public tech market inversions, highlighting how pre-revenue speculative companies SPAC while cash-flow monster companies stay private. Rory explains the contrasting dynamics between collaborative chip supply chains and predatory DRAM memory pricing.1:09–9:10 · Guest disagreement 2/10 Impact of Chinese Open-Weight AI Models Harry introduces the topic of Chinese open-weight models Kimi and Qwen catching up to frontier Western models. The guests lead the conversation, discussing evaluation accuracy and the political fallout from OpenAI policy staff tweets.9:10–19:35 · Guest disagreement 3/10 AI Model Policy, Regulation, and Exfiltration Risks Harry challenges Jason on data export fears by pointing out that CIOs are told on-prem deployments remove backdoor risks. Jason pushes back forcefully, arguing that complex LLM behavior cannot be fully audited or trusted regardless of on-prem hosting.19:35–31:27 · Guest disagreement 5/10 OpenRouter M&A Rumors and Model Routing Infrastructure When Harry asks if a board should sell OpenRouter for $5B to $6B, Jason calls out the question as a classic VC-centric mindset. Jason educates the host on how founder economics differ from investor fund returns.31:27–39:25 · Guest disagreement 1/10 Fireworks AI Funding and Infrastructure vs Application Value Harry demonstrates strong topic knowledge by presenting the detailed deal terms and operational metrics for Fireworks AI. The guests agree and elaborate on inference unit economics and capex requirements.39:25–52:11 · Guest disagreement 1/10 Custom Micro-Models, Data Labeling, and Model Economics The conversation moves to fine-tuning, domain-specific micro-models, and data labeling economics. Jason shares hands-on experience building an agentic app and explains how domain expert labeling vastly outperforms generic foundation models.52:11–1:04:18 · Guest disagreement 2/10 Stripe's Strategic Acquisition Bid for PayPal Harry prompts the guests regarding rumors of Stripe making an acquisition bid for PayPal alongside Advent. Rory and Jason explain public company board dynamics, Delaware law fiduciary duties, and the standard M&A premium negotiation dance.1:04:18–1:18:09 · Guest disagreement 3/10 Venture Capital Market Dynamics and Tranche Financing Structures Harry takes an active expert role, highlighting a sharp market disconnect where early-stage Series A valuations command 50x-100x revenue multiples while scaled growth companies sell for 10x forward revenue. He defends the risk-adjusted value of growth stage investing.1:18:09–1:27:29 · Guest disagreement 1/10 Private vs Public Tech Markets and Hardware Supply Chains The panel discusses private versus public tech market inversions, highlighting how pre-revenue speculative companies SPAC while cash-flow monster companies stay private. Rory explains the contrasting dynamics between collaborative chip supply chains and predatory DRAM memory pricing.1:09–9:10 · Harry pushing back 1/10 Impact of Chinese Open-Weight AI Models Harry introduces the topic of Chinese open-weight models Kimi and Qwen catching up to frontier Western models. The guests lead the conversation, discussing evaluation accuracy and the political fallout from OpenAI policy staff tweets.9:10–19:35 · Harry pushing back 4/10 AI Model Policy, Regulation, and Exfiltration Risks Harry challenges Jason on data export fears by pointing out that CIOs are told on-prem deployments remove backdoor risks. Jason pushes back forcefully, arguing that complex LLM behavior cannot be fully audited or trusted regardless of on-prem hosting.19:35–31:27 · Harry pushing back 3/10 OpenRouter M&A Rumors and Model Routing Infrastructure When Harry asks if a board should sell OpenRouter for $5B to $6B, Jason calls out the question as a classic VC-centric mindset. Jason educates the host on how founder economics differ from investor fund returns.31:27–39:25 · Harry pushing back 2/10 Fireworks AI Funding and Infrastructure vs Application Value Harry demonstrates strong topic knowledge by presenting the detailed deal terms and operational metrics for Fireworks AI. The guests agree and elaborate on inference unit economics and capex requirements.39:25–52:11 · Harry pushing back 2/10 Custom Micro-Models, Data Labeling, and Model Economics The conversation moves to fine-tuning, domain-specific micro-models, and data labeling economics. Jason shares hands-on experience building an agentic app and explains how domain expert labeling vastly outperforms generic foundation models.52:11–1:04:18 · Harry pushing back 2/10 Stripe's Strategic Acquisition Bid for PayPal Harry prompts the guests regarding rumors of Stripe making an acquisition bid for PayPal alongside Advent. Rory and Jason explain public company board dynamics, Delaware law fiduciary duties, and the standard M&A premium negotiation dance.1:04:18–1:18:09 · Harry pushing back 5/10 Venture Capital Market Dynamics and Tranche Financing Structures Harry takes an active expert role, highlighting a sharp market disconnect where early-stage Series A valuations command 50x-100x revenue multiples while scaled growth companies sell for 10x forward revenue. He defends the risk-adjusted value of growth stage investing.1:18:09–1:27:29 · Harry pushing back 2/10 Private vs Public Tech Markets and Hardware Supply Chains The panel discusses private versus public tech market inversions, highlighting how pre-revenue speculative companies SPAC while cash-flow monster companies stay private. Rory explains the contrasting dynamics between collaborative chip supply chains and predatory DRAM memory pricing.

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

0:00 · Harry 47.6% · guest 52.4%0:00 · Harry 47.6% · guest 52.4%3:00 · Harry 10.6% · guest 89.4%3:00 · Harry 10.6% · guest 89.4%6:00 · Harry 0% · guest 100%6:00 · Harry 0% · guest 100%9:00 · Harry 6.6% · guest 93.4%9:00 · Harry 6.6% · guest 93.4%12:00 · Harry 10.7% · guest 89.3%12:00 · Harry 10.7% · guest 89.3%15:00 · Harry 0% · guest 100%15:00 · Harry 0% · guest 100%18:00 · Harry 31% · guest 69%18:00 · Harry 31% · guest 69%21:00 · Harry 0% · guest 100%21:00 · Harry 0% · guest 100%24:00 · Harry 2.2% · guest 97.8%24:00 · Harry 2.2% · guest 97.8%27:00 · Harry 4.3% · guest 95.7%27:00 · Harry 4.3% · guest 95.7%30:00 · Harry 32.3% · guest 67.7%30:00 · Harry 32.3% · guest 67.7%33:00 · Harry 7.3% · guest 92.7%33:00 · Harry 7.3% · guest 92.7%36:00 · Harry 5.1% · guest 94.9%36:00 · Harry 5.1% · guest 94.9%39:00 · Harry 22.3% · guest 77.7%39:00 · Harry 22.3% · guest 77.7%42:00 · Harry 0% · guest 100%42:00 · Harry 0% · guest 100%45:00 · Harry 4.7% · guest 95.3%45:00 · Harry 4.7% · guest 95.3%48:00 · Harry 5.8% · guest 94.2%48:00 · Harry 5.8% · guest 94.2%51:00 · Harry 28.7% · guest 71.3%51:00 · Harry 28.7% · guest 71.3%54:00 · Harry 0% · guest 100%54:00 · Harry 0% · guest 100%57:00 · Harry 2% · guest 98%57:00 · Harry 2% · guest 98%1:00:00 · Harry 0% · guest 100%1:00:00 · Harry 0% · guest 100%1:03:00 · Harry 11.8% · guest 88.2%1:03:00 · Harry 11.8% · guest 88.2%1:06:00 · Harry 52.4% · guest 47.6%1:06:00 · Harry 52.4% · guest 47.6%1:09:00 · Harry 12.9% · guest 87.1%1:09:00 · Harry 12.9% · guest 87.1%1:12:00 · Harry 11.8% · guest 88.2%1:12:00 · Harry 11.8% · guest 88.2%1:15:00 · Harry 14.6% · guest 85.4%1:15:00 · Harry 14.6% · guest 85.4%1:18:00 · Harry 4.7% · guest 95.3%1:18:00 · Harry 4.7% · guest 95.3%1:21:00 · Harry 1.1% · guest 98.9%1:21:00 · Harry 1.1% · guest 98.9%1:24:00 · Harry 7.4% · guest 92.6%1:24:00 · Harry 7.4% · guest 92.6%1:27:00 · Harry 61.1% · guest 38.9%1:27:00 · Harry 61.1% · guest 38.9%
Sharpest disagreement ▶ 25:27 Jason rejects VC-centric framing

Jason forcefully interrupts Harry's line of questioning about selling at a $6 billion valuation, declaring that the question triggered him because it represents a narrow VC return perspective that ignores founder incentives.

Hardest push from Harry ▶ 12:06 Host challenges guest on on-prem AI security

Harry directly refuses Jason's premise about Chinese open model security risks by raising the standard enterprise argument that hosting models on-premises completely eliminates backdoors.

Biggest teaching moment ▶ 25:27 Jason educates host on founder vs VC financial logic

Jason dismantles Harry's selling scenario by explaining that a 3x exit does not change a founder's life stack risk profile, requiring a 10x trajectory to justify continuing.

Harry holds his own ▶ 1:05:56 Host demonstrates market expertise on valuation multiples

Harry shows deep domain knowledge by breaking down actual market data, pointing out the irrationality of paying $300M for $2M ARR at Series A compared to paying 10x ARR for proven scale at Series B or growth rounds.

the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Impact of Chinese Open-Weight AI Models 2221 Harry introduces the topic of Chinese open-weight models Kimi and Qwen catching up to frontier Western models. The guests lead the conversation, discussing evaluation accuracy and the political fallout from OpenAI policy staff tweets.
AI Model Policy, Regulation, and Exfiltration Risks 3434 Harry challenges Jason on data export fears by pointing out that CIOs are told on-prem deployments remove backdoor risks. Jason pushes back forcefully, arguing that complex LLM behavior cannot be fully audited or trusted regardless of on-prem hosting.
OpenRouter M&A Rumors and Model Routing Infrastructure 3653 When Harry asks if a board should sell OpenRouter for $5B to $6B, Jason calls out the question as a classic VC-centric mindset. Jason educates the host on how founder economics differ from investor fund returns.
Fireworks AI Funding and Infrastructure vs Application Value 4212 Harry demonstrates strong topic knowledge by presenting the detailed deal terms and operational metrics for Fireworks AI. The guests agree and elaborate on inference unit economics and capex requirements.
Custom Micro-Models, Data Labeling, and Model Economics 3212 The conversation moves to fine-tuning, domain-specific micro-models, and data labeling economics. Jason shares hands-on experience building an agentic app and explains how domain expert labeling vastly outperforms generic foundation models.
Stripe's Strategic Acquisition Bid for PayPal 3322 Harry prompts the guests regarding rumors of Stripe making an acquisition bid for PayPal alongside Advent. Rory and Jason explain public company board dynamics, Delaware law fiduciary duties, and the standard M&A premium negotiation dance.
Venture Capital Market Dynamics and Tranche Financing Structures 6335 Harry takes an active expert role, highlighting a sharp market disconnect where early-stage Series A valuations command 50x-100x revenue multiples while scaled growth companies sell for 10x forward revenue. He defends the risk-adjusted value of growth stage investing.
Private vs Public Tech Markets and Hardware Supply Chains 3312 The panel discusses private versus public tech market inversions, highlighting how pre-revenue speculative companies SPAC while cash-flow monster companies stay private. Rory explains the contrasting dynamics between collaborative chip supply chains and predatory DRAM memory pricing.

Statements from this episode (35)

Prediction Not checkable as stated
O'Driscoll: Massive AI infrastructure spending will require paying applications eventually
“Some point, the people spending a trillion dollars a year are gonna want some apps to pay for all this.”
Rory O'Driscoll Jul 23, 2026 ▶ 0:42
Insight
O'Driscoll: 10x annual growth with positive margins covers all overhead
“If you're growing 10 X year on year, and you have any kind of positive and improving gross margin, it just covers all the nut.”
Rory O'Driscoll Jul 23, 2026 ▶ 49:23
Assertion Supported
Lemkin: Half of OpenRouter traffic is for Chinese-created AI models
“If you look at you know, if you look at open router data, half the traffic's through China, China created models”
Jason Lemkin Jul 23, 2026 ▶ 2:40
Assertion Not checkable as stated
O'Driscoll: Chinese AI models lag Western frontier models by 6 to 9 months
“They're not state of the art compared to the frontier models, but they're, you know, six, nine months behind, depending on how you measure it.”
Rory O'Driscoll Jul 23, 2026 ▶ 3:50
Assertion Supported
O'Driscoll: Chinese AI model Kimi K-3 has 2.8 trillion parameters
“Conversely, Kimi K-III is, I think, a two-point-eight-trillion-parameter model.”
Rory O'Driscoll Jul 23, 2026 ▶ 4:41
Prediction Open · timeframe Jul 2031
Lemkin: The US government will never use Chinese-built AI models
“It's difficult for me to imagine. The federal government's ever going to use a China built model at this point in the U S right.”
Jason Lemkin Jul 23, 2026 ▶ 7:33
Assertion Supported
O'Driscoll: Chinese open-weight AI startups reach $50B–$70B valuations
“Because, you know, the open weight models in China are getting 50, seventy billion dollar valuations.”
Rory O'Driscoll Jul 23, 2026 ▶ 17:10
Assertion Partly supported
O'Driscoll: Chinese AI models rely on distillation illegal in the US
“Maybe it's because the dirty little secret is a lot of their advantage is distillation, which you can't legally do if you're US-based.”
Rory O'Driscoll Jul 23, 2026 ▶ 17:27
Disclosure
Stebbings: Offered $5M SPV allocation in Chinese AI startup Kimi
“I was offered Kimmy today, by the way, Rory at 20 Berlin. This was the, it fell into my inbox. I have an SPV for you. Do Kimmy at 20 Berlin. We're oversubscribed, but we'll make room for five million for Harry.”
Harry Stebbings Jul 23, 2026 ▶ 18:23
Insight
O'Driscoll: VCs cannot force a startup sale without core founder buy-in
“Even if, as the VCs, we have board control, 70% ownership, and a drag along for the founders. Jason knows this. If the founders who are core to the business don't want to sell, it's not going to happen.”
Rory O'Driscoll Jul 23, 2026 ▶ 24:48
Insight
Lemkin: Founders shouldn't reject major buyout offers unless 10x upside exists
“I think for a founder, when you start to get into nosebleed offers in absolute terms, it has to be 10 X to go for it. It's not worth it for three X. It is not.”
Jason Lemkin Jul 23, 2026 ▶ 26:00
Insight
Lemkin: Ideal startup sale timing is right before market recognizes commoditization
“And the perfect outcome is to sell the moment it becomes commoditized, but before everyone fully realizes it, that's when they'll give you the money, but that's before the value decrease rather than it creates in it.”
Jason Lemkin Jul 23, 2026 ▶ 30:32
Prediction Open · timeframe Jul 2029
O'Driscoll: AI inference providers will become significantly more CapEx-intensive
“If I'm buying data center compute and then effectively selling data center compute with hosted LLM, at some point I'm going to want to own my own data center assets to have more control of my destiny, which means vertically integrating downwards, which also me…”
Rory O'Driscoll Jul 23, 2026 ▶ 35:29
Opinion
Lemkin: the AI application layer era is not here yet
“All the good investments sure seem to be in the infrastructure. So I'm waiting for the era of the application Layer in AI and making bets and seeing some good stuff, but I don't believe it's here yet. I actually don't believe the application layer is here yet.”
Jason Lemkin Jul 23, 2026 ▶ 36:06
Assertion Partly supported
O'Driscoll: AI infrastructure spend hits $900B while AI apps struggle past $50B
“Zooming out a million miles, you know, my mental model is, I divide the AI world up into three buckets. It's the making AI, the infrastructure layer, right? And you're right, the spend there is eight, nine hundred billion dollars a year. Then there's the two f…”
Rory O'Driscoll Jul 23, 2026 ▶ 37:21
Assertion Not checkable as stated
O'Driscoll: OpenAI and Anthropic training data spend exceeds non-Cursor AI app revenues
“There's probably more money being spent on training data for the foundation models, you know, the Mercosurge and that, than pretty much any app company outside of Cursor. In fact, probably the sum of all the apps companies outside of Cursor, right, you know, a…”
Rory O'Driscoll Jul 23, 2026 ▶ 38:16
Prediction Not checkable as stated
Lemkin: Generic AI model usage will drop strictly to prototypes
“Some version of this, I think folks that are going to want to use at any application level, folks that are going to want to use just the generic models is just going to decline to, Prototypes, right? Prototypes and proofing.”
Jason Lemkin Jul 23, 2026 ▶ 40:37
Opinion
Lemkin: Generic LLMs are mediocre compared to expert-labeled domain models
“The generic LLMs, which are a sea of mediocrity combined into one giant LLM. Okay. Every mediocre history professor, every, every mediocre doctor that doesn't even know what caused your runny nose is in the LLM. But if you get the best people training it on th…”
Jason Lemkin Jul 23, 2026 ▶ 42:17
Assertion Contradicted
O'Driscoll: Hyperscaler RPO depends entirely on foundation model commitments
“Because, let me be clear, if you know the answer to that question, that one question, you know the answer to the entire direction of the U.S. Stock market for the next two years. Because all the hyperscaler RPO, all of it, is a function of the commitments they…”
Rory O'Driscoll Jul 23, 2026 ▶ 45:44
Insight
O'Driscoll: 20x-revenue AI valuations demand Microsoft-level 40% margins
“But as you're pointing out here, there are real, even at the margin, even after you've fully paid for your training costs, there are real physical costs to serve these models, and you've got to cover your nut. You got to cover the marginal cost of the model of…”
Rory O'Driscoll Jul 23, 2026 ▶ 48:33
Assertion Supported
O'Driscoll: Stripe and PayPal Each Process $1.8 Trillion Annually
“They both process kind of 1.8 trillion dollars a year, right?”
Rory O'Driscoll Jul 23, 2026 ▶ 52:50
Assertion Supported
O'Driscoll: Stripe Generates Around $6 Billion in Net Revenue
“Stripe supports revenue net, which is around six billion plus or minus.”
Rory O'Driscoll Jul 23, 2026 ▶ 53:44
Assertion Partly supported
O'Driscoll: Stripe's Annual Growth Rate Is Between 20% and 30%
“It's between 20 and 30, so it's not that much bigger, Jason.”
Rory O'Driscoll Jul 23, 2026 ▶ 55:50
Prediction Open · timeframe Jul 2029
Lemkin: PayPal's Board Will Ultimately Accept Stripe's Acquisition Offer
“The board rejected it, right? And the fact that the board rejected it means to me that they're going to accept it.”
Jason Lemkin Jul 23, 2026 ▶ 58:36
Prediction Open · timeframe Jul 2029
Lemkin: Stripe-PayPal Acquisition Premium Will Land at Around 35%
“So it's probably just a dance from 28 to 35. And then it gets parked with advent to while they figure out antitrust and capital issues.”
Jason Lemkin Jul 23, 2026 ▶ 1:02:58
Assertion Supported
Stebbings: Hot AI Series A valuations hit $500M on $5M revenue
“Is I'm seeing Series A is priced at three to 500 on two to five million in revenue, but I'm finding the B at a hundred million in revenue priced at one to 1.5. It's a three X price increase for a 50 X revenue increase.”
Harry Stebbings Jul 23, 2026 ▶ 1:06:13
Insight
Lemkin: Series B VCs now need seed-level picking skills to survive
“I think the real pressure is, it means anything below that growth stage, you better be a damn good picker. Because it used to be when Rory and I met, Series B, even into Series A, you actually didn't have to be a good picker. You just had to be good at math an…”
Jason Lemkin Jul 23, 2026 ▶ 1:07:45
Assertion Not publicly verifiable
O'Driscoll: 40% of early 2025 unicorns get marked up within 18 months
“We looked at every, I mean, if you look at all the unicorns that were minted in Q-one or Q-two of 25, by the end of Q-two 26, at least 40% of them will have had a subsequent markup.”
Rory O'Driscoll Jul 23, 2026 ▶ 1:11:25
Insight
O'Driscoll: tranche structures price away the growth-round excess return, and that is how the trend ends
“So now what you're seeing with these tranche deals is, You know, nature abhors a vacuum, and sequoia abhors leaving a dollar on the table, so what's happening is people are realizing everyone wants these growth rounds, and this is how these trends end. Everyon…”
Rory O'Driscoll Jul 23, 2026 ▶ 1:12:01
Insight
O'Driscoll: Heavy Structure and Excessive Debt Are Worse Than Two-Tranche Rounds
“And I will say they're silly, but they're not horrific. I mean, if you look at that versus other alternatives, like, you know, taking a high price but with a ton of structure, real structure, that's a worse mistake. If you look at it, you know, not raising mon…”
Rory O'Driscoll Jul 23, 2026 ▶ 1:17:33
Opinion
O'Driscoll: SPACs take venture-grade risk public while the best venture assets stay private
“If you think about the kind of companies that should be private, and the kind of companies that should be public, companies trying to do, you know, next generation nuclear products should probably be private. As yet, there's three of them that are public, they…”
Rory O'Driscoll Jul 23, 2026 ▶ 1:18:45
Assertion Supported
Lemkin: C Squared IPO'd at $3B Market Cap with $1B Run Rate
“They're doing a billion dollar run rate growing 16%. Right. And they IPO'd at, with a three billion dollar market cap.”
Jason Lemkin Jul 23, 2026 ▶ 1:20:06
Assertion Partly supported
O'Driscoll: Nvidia and TSMC Have No Written Contract Despite 30-Year Partnership
“You have the NVIDIA relationship with TSMC, which famously, they don't even have a written contract. They've dealt with each other for 30 years.”
Rory O'Driscoll Jul 23, 2026 ▶ 1:21:46
Prediction Open · timeframe Jul 2028
O'Driscoll: DRAM Memory Pricing Will Suffer Brutal Collapse in 1-2 Years
“And when that, the big aha for me is when that Pricing breaks. It'll be brutal to the downside, but maybe that's a year, two years from now.”
Rory O'Driscoll Jul 23, 2026 ▶ 1:24:03
Opinion
O'Driscoll: OpenAI and Anthropic 2026-2027 Growth Is Key Metric for AI Market
“Going back to this first sentence, the only thing that matters is the open AI and anthropic growth rate in 26 and 27.”
Rory O'Driscoll Jul 23, 2026 ▶ 1:26:53
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