Feb 19, 2026 · 1h 37m · news
Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
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In this episode of 20VC, host Harry Stebbings, along with veteran investors Jason Lemkin and Rory O'Driscoll, analyze the profound disruption generative AI is bringing to traditional SaaS business models, the emergence of autonomous software agents, and the shifting dynamics of venture capital and corporate leadership.
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 10.9% of the talking time here. How this is scored →
Harry as informed peer 4.6 Guest teaching 3.5 Guest disagreement 2.3 Harry pushing back 3.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:13:38 Jason Dismisses Early-Stage Venture Motivations
Jason forcefully rejects the idea that VCs leave mega-funds out of a passion for early-stage investing, claiming everyone just wants carry from mega-rounds.
Hardest push from Harry ▶ 23:21 Harry Refuses Conversational UI PremiseHarry directly pushes back on Jason's claim that e-commerce is shifting to conversational commerce, arguing consumers prefer visual browser discovery UIs.
Biggest teaching moment ▶ 6:35 Rory Contextualizes Anthropic Growth HistoryRory educates the room by benchmarking Anthropic's three-year 10x revenue growth against early Microsoft, Google, and Compaq to demonstrate its unprecedented nature.
Harry holds his own ▶ 47:37 Harry Demonstrates Fund Mechanics ExpertiseHarry counters Jason's slow-category AI investing thesis by explaining why it fails without lifecycle reserve capital given cash opportunity costs.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| The Unprecedented Rise of Anthropic and AI Momentum | 5 | 4 | 1 | 2 | Harry introduces Anthropic's $30B round at $380B valuation and cites data on early-stage oversubscription ($30M Series A with $1.2B demand) and Dario Amodei's compute risk quotes. The guests expand with historical market analogies to early tech giants. | |
| Enterprise AI Budgets and the Fight for Dominance | 5 | 4 | 1 | 1 | Harry prompts with precise quantitative questions regarding Anthropic vs OpenAI enterprise revenue splits and software spend forecasts. Rory gently reframes the dynamic as overlapping enterprise/consumer focus rather than purely zero-sum customer theft. | |
| The SaaS Gravity Well and Seat-License Devaluation | 3 | 3 | 3 | 1 | Harry asks what happens to mid-tier SaaS stocks hitting lower growth. Rory and Jason engage in a mild debate over public software bottoms and whether price eventually clears all markets. | |
| Wall Street's Shift and the Threat to E-Commerce Giants | 6 | 3 | 4 | 6 | Harry directly challenges Jason's premise that conversational UI will replace e-commerce web browsing, arguing consumer behavior favors visual browsing and discovery over chat boxes. | |
| Managing Portfolio Whiplash and the Redefinition of SaaS | 0 | 2 | 1 | 0 | A guest-dominated discussion defining old school SaaS versus new school AI-native applications and private portfolio whiplash. The host does not speak in this segment. | |
| Figma's AI Adjacent Vulnerability vs. Replit and Lovable | 5 | 4 | 1 | 2 | Harry corrects the ARR scale for Lovable and Replit to $350M and questions if Figma is being unfairly discounted. Jason provides a sharp breakdown of how Figma missed the prototyping product wave. | |
| AI SDRs and the Rapid Pace of Autonomous Software | 1 | 3 | 4 | 0 | Jason recounts an AI SDR booking a six-figure deal autonomously. The host barely speaks, while Rory pushes back on Jason to clarify whether it booked actual revenue or just an introductory meeting. | |
| AI Investing Strategies and the Speed of Sequencing | 7 | 2 | 2 | 6 | Harry challenges Jason's slow-category VC strategy by demonstrating why lifecycle funding mechanics make it capital inefficient. Harry also shares firsthand market observations from legal tech pricing pressures. | |
| Stripe vs. Adyen: The Battle of Growth and Flexibility | 6 | 4 | 2 | 6 | Harry offers a counter-thesis on the Stripe vs Adyen valuation discrepancy, asserting that Adyen leadership's poor investor communication directly causes its valuation discount. | |
| OpenClaw and the Advent of Autonomous Agents | 5 | 4 | 2 | 4 | Harry asks probing questions about inference demands and whether Anthropic made a strategic error by not acquiring OpenClaw. Jason details the developer movement around autonomous agents breaking platform guardrails. | |
| AI Security, Agentic Guardrails, and Security Liability | 5 | 3 | 1 | 4 | Harry interjects to point out that CISOs bear primary organizational blame for rogue agentic security breaches and reveals an active investment in agent security. | |
| Late-Stage Capital Growth and Thrive's $10B Fund | 4 | 5 | 1 | 2 | Harry asks how large venture growth funds can scale. Rory educates on the fund sizing math required to maintain 10% ownership stakes in $100B+ private tech leaders. | |
| The Talent Drain: VC Partner Departures and Autonomy | 6 | 4 | 6 | 6 | Jason combatively claims VCs never leave mega-funds for early-stage passion and only care about carry. Harry directly rejects this monetary reductionism, highlighting post-economic motivations and citing specific high-profile partner moves. | |
| The Return of the Founder CEO in the Age of AI | 5 | 4 | 2 | 2 | Harry brings in context from his interview with 11 Labs' sales leadership regarding extreme quotas. Jason and Rory explain why returning founder CEOs possess the unique organizational authority needed to execute painful AI transitions. | |
| CEO Predictions and the Durability of SaaS Giants | 5 | 3 | 2 | 2 | Harry asks which public tech founder will return next, citing HubSpot's valuation drop. The guests reframe the premise around who is likely to quit instead. | |
| Monday.com and the Durability Matrix of Public Cloud Stocks | 6 | 4 | 3 | 4 | Harry presents detailed financial guidance and margins for Monday.com and presses the guests on whether it's a buy. Jason proposes a real $200k public stock portfolio challenge for the podcast. |
Statements from this episode (42)
Stebbings: Anthropic raised $30B at a $380B valuation, up from $10B
“Anthropic raises thirty billion at a three hundred and eighty billion dollar post money. Now, it was originally ten billion and it upscaled to a thirty billion dollar round.”
Stebbings: $30M Series A rounds are seeing $1.2B in investor demand
“I'm doing rounds today where even at the early stage, a thirty million dollar series A round has 1.2 billion dollars of demand.”
O'Driscoll: Anthropic is clearly the best AI model for enterprise
“Anthropic looks like, for enterprise, it's clearly the best model.”
O'Driscoll: Anthropic's three-year 10x revenue growth is unprecedented in tech history
“The truth is you've never seen a company grow 10 X in gap revenue and runway year on year for three years. Right? At this scale. It just hasn't happened.”
O'Driscoll: Less than 20% of Anthropic's Claude revenue comes from consumers
“Most of OpenAI's revenues comes from ChatGPT on the consumer side, and Claude, less than 20% of the revenue is consumer.”
Lemkin: Anthropic revenue surged to 64% of OpenAI's in 14 months
“Anthropic said it's hundred K customers are up seven X in the last year. So there's not enough time to steal deals. Having said that, going from five percent of OpenAI's revenue to 64% in 14 months, that is stealing budget.”
Lemkin: Fortune 500 will actively replace human employees with AI by year-end
“By the end of this year, that, that train is going to be so far out of the station that, that these growth numbers will be jaw dropping because we will decide enterprises will the fortune 500 or global 2000 will decide we are replacing humans with AI.”
O'Driscoll: Enterprise AI spending will surge for two years before retrenchment
“My gut would be people will overbet, overinvest, and you will have a retrenchment period, you know, two plus years from now, but I think right now you're just looking at two years where, you know, just as the hyperscaler said two years ago, we're going to do t…”
Lemkin: Public SaaS revenue growth has dropped to nearly 10% annualized
“As a cohort, public Software stocks are approaching, have fallen to almost 10% growth annualized.”
Lemkin: Dropbox is currently experiencing negative 1% annual growth
“Dropbox growing minus one percent a year is not crushing it, is it?”
O'Driscoll: Shopify's Core Infrastructure Safe From Near-Term AI Displacement
“I don't think there is a credible near-end story that replaces a shopping, a website for shopping, and a payments mechanism, which is, you know, 60, 70% of their business, with some kind of AI arm wave in a way that there is for many of the workflow automation…”
Lemkin: Shopify's storefront software interface may become obsolete within two years
“That software in two years may be obsolete.”
Lemkin: Open Platforms Risk Better AI Agents; Closed Platforms Risk Bypass
“I believe every platform that is open is at risk that an agent is better than the native platform. And every platform that is closed is, is at risk of being At least slightly bypassed.”
Lemkin hasn't logged into Salesforce in six months; AI agents run it
“I haven't logged into Salesforce in six months. But we use it every, every minute. Our agents use it every minute.”
O'Driscoll: Software accounts for four percent of US GDP
“Software was the best industry of the last 2030 years. At the end of 2030 years, it accounts for four percent of the US GDP.”
Lemkin: Fund sits at 4.5x, but non-AI startups are struggling
“When I look at my last fund, right, you know, and I see what's happening and it, the funds in good shape, whatever, 4.5 X. But honestly, like two companies are like, Massively benefiting from the current world and B to B massively benefit in accelerating. One …”
Stebbings: $8M-$20M ARR portfolio startups are stepping off the venture track
“I just see a realization in my portfolio now of companies that are in the eight to twenty million ARR range, not benefiting massively, but growing 80 to a hundred percent that are basically like, okay, we've raised our last venture dollars and we're going to h…”
Lemkin: Figma missed $300M-$400M in AI prototyping revenue to Replit and Lovable
“That lovable and replet should not be owning product prototyping and development for product people. Figma should own this. They don't. They missed a whole generation. Here. And that's the, that ties into all of this. Figma, can't argue with Figma today. That …”
O'Driscoll: SaaS companies ignoring AI will see multiples fall to 4x-5x
“If you don't get on top of this soon, That 10 X revenues is going to go on a five and four and where the other seven percent growth was are. Fast forward five years, there's really only one or two stories. They get on top of this, they get a third market share…”
O'Driscoll: 80% of accounting software value is independent of AI
“I believe the next generation of accounting software companies, we've looked at them. They're super interesting. They're adding AI, but fundamentally, 80% of the value in an accounting software package is independent of AI. It's just, it's debits and credits a…”
Lemkin: AI agent vendors lack defensibility because customers rapidly switch products
“I'd actually don't think any of the agent vendors are safe from disruption because we will, even us, like everyone's promiscuous with agents. We will switch it. Like, this is so much better than what we had two weeks ago. We'll switch to the next one.”
O'Driscoll: AI coding tools Lovable and Replit generate $300M-$400M in revenue
“If you take, you know, again, to your example of, I'm sorry, my brain Figma, right? The maker, the next generation product tools like lovable, And Replit, right, they're doing three, four hundred million in space.”
Lemkin: Distressed SaaS companies in 'hospice care' never recover
“If you've gone on to hospice care, does it really matter how long you stay in hospice? I mean, to the kid, to the employees, it does to the family, but everybody pretty much knows when that SAS company goes into hospice, it ain't coming out.”
O'Driscoll: Legal tech was miserable in SaaS but thrives with AI LLMs
“Legal was a miserable category in SAS land. It's been amazing in AI land because LLMs manipulate language and lawyers manipulate language too.”
O'Driscoll: Stripe generates $5B in revenue compared to Adyen's $2B
“Stripe's doing five billion plus or minus, Addians doing A two billion, right? So it's half the size. So two and a half times the size.”
O'Driscoll: Adyen operates at nearly 50% operating margins
“Addion's a wildly profitable company. It's like almost 50% operating margins.”
Lemkin: Stripe is a better bet than Adyen due to private flexibility
“So I'm going to bet on Stripe on this one, just because I think you have more flexibility today to respond to change.”
Lemkin: Replit V4 will autonomously build software features overnight
“I know on the next release of Replit, not only does it happen because they've built their own set of guard roles, but the agents do it at night. So in the next release of Replit, when you log in the next day, it will have built three to four features for you o…”
O'Driscoll: Founders are building agent-first AI security software
“So my guess is, even as we speak, there's people building really compelling agent-first security products to make darn sure that doesn't happen.”
O'Driscoll: Thrive executed exceptional stock-picking with Stripe, Databricks, OpenAI
“I mean, I think, we said it in one of the shows earlier on, Thrive has done an amazing stock picking job of backing Stripe, of backing Databricks, of backing OpenAI, and of backing them at scale.”
O'Driscoll: Thrive Capital specifically declined Anthropic investment due to OpenAI stake
“They actually specifically, unlike some of the other funds that have invested in both, they've Specifically our fund that said, no, we backed open AI. We're not going to back on tropics.”
Lemkin: Peak XV almost imploded because the managing partner hoarded economics
“I mean, peak, peak 15 almost imploded, right? Because the managing partner wanted to keep all the economics, right?”
Lemkin: Chamath Palihapitiya has been sued by all his former partners
“Chamath, all his ex-partners have sued him. Mamoon sued them. The Grok guys he sued.”
Lemkin: VC Funds Vest Carry Over 10 Years to Penalize Leavers
“These are carries many funds now vest over 10 years. Some even backload carry, right? Because they want to penalize the folks that leave.”
O'Driscoll: AI disruption requires founder knowledge over generic executive skills
“What you don't need in this kind of situation is generic business skills. What you need is massively specific knowledge and skills and courage to make the changes that you know you have to make. And that is where a founder's advantage.”
Lemkin: Traditional 2022 SaaS playbooks still work at top AI companies
“The 2023, 20 22 toolkit works perfectly well at the hottest AI companies. It really does. It really does.”
Stebbings: HubSpot's market cap has fallen 45% to $12.5B
“You're looking at 12 and a half billion now market cap for them down 45% in the last six months.”
Lemkin: Mistreated founder CEOs will return if boards offer humble pie and big packages
“When you're treated terribly as a CEO was like Jeff is, if people come back with humble pie and you care, you get over it. You got to pay the price. Like they might have to have to have given them a half million billion dollar package, but if there's a little …”
Lemkin: Yelp's valuation is down 47% this year to $1.2 billion
“Yelp's down to 1.2 billion dollar valuation. I mean, Jeremy's young, but it's been what? 20 something years, right? And it's down 47% this year to almost just over a billion.”
O'Driscoll: 10x Cash Flow for 20% Growth Is Wildly Cheap
“10 times cash flow for something growing sustainably at 20% is wildly cheap.”