Dec 18, 2025 · 1h 21m · news
Will Cursor Kill Figma? Lightspeed Raises $9B & OpenAI’s $1B from Disney & #1 App in App Store · 20VC with Harry Stebbings
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A panel of tech investors analyzes the shifting dynamics of venture capital, exploring how massive late-stage funds keep tech giants private longer, how AI code generators threaten to disrupt legacy SaaS incumbents, and the volatile public market reactions to massive AI infrastructure spending.
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 9.9% of the talking time here. How this is scored →
Harry as informed peer 3.1 Guest teaching 3.9 Guest disagreement 2.8 Harry pushing back 2.4
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 11:35 Rory dismisses Harry's Disney OpenAI topic
Rory bluntly rejects Harry's framing, calling the $1B Disney partnership one of the least interesting news items and dismissing it as round-tripping.
Hardest push from Harry ▶ 14:47 Harry defends strategic logic of Disney IPHarry pushes back against Rory's dismissal, arguing that locking up Disney IP provides essential consumer retention against model commoditization.
Biggest teaching moment ▶ 31:06 Rory explains Apollo entry PE return correlationRory provides a deep analysis of Vanguard and Apollo historical data, explaining how entry PE multiples dictate 10-year equity returns using Cisco in 1999 as evidence.
Harry holds his own ▶ 4:07 Harry cites fund return data from David George interviewHarry counters guest skepticism about large multi-stage venture fund math by citing specific fund multiples from Databricks and Coinbase.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Lightspeed's $9B Fund Expansion & The Barbelled Venture Market | 4 | 3 | 3 | 3 | Harry calculates Lightspeed's fund split and cites data from his show with David George on Databricks and Coinbase returns. Jason and Rory reframe his point about seed manager appetite, noting that multistage speed can swamp seed dynamics. | |
| Late-Stage Capital Flood & The 'Greatest Gift' of Staying Private | 2 | 4 | 2 | 1 | Harry asks if late-stage venture has ever been more competitive. Jason and Rory reframe competition around structural private market compounding, contrasting Tesla's early IPO with SpaceX staying private. | |
| OpenAI's Dominance: Disney's $1B Partnership & App Store Success | 4 | 5 | 5 | 4 | Rory aggressively dismisses Harry's topic on Disney's $1B deal with OpenAI as round-tripping and uninteresting. Harry pushes back by arguing Disney IP provides defensible lock-in against model commoditization. | |
| The Death of the One-Year Cliff: A New Era in Tech Talent Acquisition | 2 | 3 | 1 | 1 | Harry introduces the trend of eliminating 1-year vesting cliffs. Rory explains the financial mechanics of large equity packages that drive talent to reject cliffs. | |
| Oracle & Capex Jitters: The Reality of Capital-Intensive AI Infrastructure | 3 | 4 | 4 | 3 | Harry asks if Oracle's stock drop signals market jitters or a deeper breakdown. Jason forcefully disagrees with Rory's pessimistic take, framing it as brief market jitters for non-IP infrastructure providers. | |
| Broadcom's $300B Drop: Custom Silicon & Public Market Valuations | 3 | 6 | 2 | 2 | Harry asks about Apollo's forecast of zero 10-year public equity returns. Rory educates on entry valuation multiples and 10-year return correlations, using Cisco's 1999 peak as historical proof. | |
| Cursor vs. Figma: The Convergence of Design & Engineering | 3 | 3 | 2 | 2 | Harry asks if Cursor poses a direct threat to Figma. Jason lays out his category convergence thesis across sales, support, design, and code. | |
| The Maiming of SaaS: AI Category Disruption & Incumbent Grinds | 5 | 3 | 3 | 3 | Harry quotes Alex Rampel on distribution versus innovation to challenge incumbent dynamics. Rory and Jason discuss how AI maims existing SaaS growth without killing customer logos outright. | |
| Boom Supersonic's Pivot: From Aviation to AI Data Center Energy | 1 | 4 | 2 | 1 | Harry asks about Boom Supersonic selling jet engines to AI data centers. Rory passionately details how jet engine architecture directly overlaps with power generation turbines. | |
| The Challenge of Hard Tech Ventures | 4 | 5 | 3 | 3 | Harry asks if a $1.5T SpaceX IPO could hold up post-listing. Rory outlines the Elon Option Value model while Jason details an anchor scenario with Google and Nvidia. | |
| Would You Rather: Figma vs. Cursor & OpenAI vs. Anthropic | 3 | 3 | 4 | 3 | Harry runs a quickfire Would You Rather segment. Jason and Rory disagree on Cursor vs Figma, leading to banter about Rory questioning Harry's interviewing skills. |
Statements from this episode (31)
O'Driscoll: Slowing growth in high-valuation bets is venture's worst nightmare
“There is nothing as terrifying as a high growth bet that slows down.”
O'Driscoll: Traditional financial metrics cannot justify SpaceX's $1.5T valuation
“You can't run the numbers on SpaceX and come up with that 1.5 trillion. You just can't.”
O'Driscoll: Lightspeed put $1B into Anthropic across two rounds
“In the last 1224 months, Lightspeed put, you know, by all accounts, a billion in two rounds of Entropic.”
Calacanis: LP appetite for new seed managers faded after 2021
“I see that appetite having faded since 2021, and I do not see a resurgence of finding tiny new managers.”
O'Driscoll: Multi-stage VCs treat seed investing as marketing expense
“The dynamics of a multistage firm mean that if they choose to, they can swamp a seed business to some extent and just ride it off as marketing.”
Calacanis: Delayed IPOs are the greatest gift to VC in modern history
“These, all these leaders not IPO-ing is the greatest gift of venture in our lifetimes. The greatest gift of venture capital, the fact that you can flood these top 20 companies With venture capital”
Calacanis: SpaceX will go public at a valuation of $1T or more
“Tesla had to IPO. Now it was a different time. It really barely had any revenue, but same guy running them. It IPO'd at 1.7 billion, which seemed very expensive. 1.7 billion. The sister company will IPO at 1.7 trillion or one trillion.”
O'Driscoll: Disney issued a cease-and-desist letter to Google over IP usage
“They sent a cease and desist letter to Google Because for unlicensed use of the content.”
O'Driscoll: ChatGPT was Apple's most downloaded app in 2025
“2025, the most down, and I checked, was the most downloaded app on Apple was ChatGPT.”
Calacanis: ChatGPT monthly user growth has slowed to single digits
“If you look at the numbers, the growth is down to single digits. Like, it's just, it is empirically true on any source. The growth is down to single digits on monthly growth.”
Calacanis: One-year equity cliffs hinder poaching talent in competitive markets
“And so on the one hand, it seems like a dumb idea, like you're creating mercenaries and perhaps you are, but in the age and you're asking someone that's 18 months into somebody else to leave and wait 12 months to make a dollar. That can be a tough sell in, in,…”
O'Driscoll: Oracle's OpenAI data center deal is a capital-intensive sugar high
“It's a sugar high, a total sugar high on a huge contract that with someone who may or may not be able to afford to pay for it, that's open AI. And even if they can afford to pay for it, it's not a great business because it's capital intensive and doesn't, not …”
Calacanis: Oracle and CoreWeave stock pullbacks are temporary market jitters
“And there's no reason actually, listen, I'm not saying that, that these are even the best companies we've ever had, but there's no reason I don't think they will rebound as the overall trends. I think these are just jitters. The overall trend I think is still,…”
O'Driscoll: Pure-play compute infrastructure acts as an amplified, high-volatility AI proxy
“They, these companies become the high octane bet on AI. If you think it's going to go up, you buy Google, you get 20% appreciation, but if you buy CoreWeave and you're right, you could get a double. You're right. So they are the highly amplified bet because th…”
O'Driscoll: Anthropic buys Broadcom chips to bypass Nvidia's 75% margins
“Why is Entropic buying chips from Broadcom? Answer. They don't want to pay 75% gross margins to Nvidia.”
O'Driscoll: Public markets will fall 30% in the next two to three years
“What tends to happen is, at one point in the next two or three years, things drop 30%, and then you crawl back slowly over the rest of the decade, right?”
Calacanis: Standalone marketing software will disappear by 2026
“In 2026 26, there will be no such thing as marketing software that got Klaviyo public. Marketing sales support have already converged to one agent.”
O'Driscoll: SaaS silos existed because human roles were siloed
“On a lot of these processes, the reason you have these separate siloed companies is the humans were siloed. There was a sales person and a marketing person, but if the AI is doing everything, let's just take the customer journey. You can have a single AI agent…”
O'Driscoll: Coding tools account for 55% of enterprise AI spend
“Citing the Menlo work, which is really nice, that, you know, 50, 60% of all the end user spend on AI right now is coding and coding related. This is the big kahuna, right? Everything else, even customer support, all the other stuff is, everything else to a rou…”
O'Driscoll: Enterprise AI revenue is $16B vs $400B in CapEx
“End users in the enterprises are spending about fundamental data 15, sixteen billion dollars on AI. And the people who make AI are spending four hundred billion dollars on quote, making AI, right?”
Jason Calacanis: Cursor will maim Figma and SaaS incumbents by lowering NRR
“I think the bigger risk for so many vendors is that it maims Figma... HubSpot and box and even anthropic using it, they don't leave, they renew, they don't buy as many seats, right? Because the team is also using cursor, but of course they don't churn. The log…”
Rory O'Driscoll: AI budget prioritization by CIOs drives public SaaS slowdown
“The way you see it is, you're, you see those CIO surveys where they rank their priorities. And what happens is, you know, as AI has gone up the zeitgeist, it's gone up the priority list, and just something that was number three goes to number six, and then it …”
Calacanis: UiPath NRR dropped from 140% at IPO to 107%
“Come, 1.8 billion in ARR, but he's got 98% GRR and a 107% NRR. Okay. So mathematically one problem is his NRR has fallen from the 140% peak at the IPO because people aren't buying that much more for UiPath, but he's got 98% GRR, 98% retention.”
Rory: Boom built a prototype aircraft with under 100 employees
“They got a prototype out for, you know, with less than a hundred headcounts.”
Calacanis: Boom crashed to $500M valuation before rising to $1.5B
“December, 20, 24, a year ago crashes down round, maybe five hundred million dollar valuation, but it might be worse when you think about the cram down and the effects. That's like not, that's a tough moment. AI, AI booms, and now you're back up to 1.5 billion.”
Calacanis: Boom Supersonic Has Sold Zero Planes and Jet Turbines
“Well, they've sold zero of either. They've sold no planes and no jet turbines for AI power.”
O'Driscoll: SpaceX is generating $15B to $16B in revenue in 2025
“The company's doing 15, sixteen billion this year, 20, 25.”
Calacanis: Google almost bailed out Tesla when it faced bankruptcy
“Google almost bailed out Tesla at the last hour when it almost went bankrupt.”
Calacanis: Peter Thiel fully vested Elon Musk's stock when firing him
“He fired him, but he treated him like a human being. Okay. He vest fully vested all his stock, took nothing out of his pocket, thanked him for it and told him that was the way it was going to be.”
O'Driscoll: Founders Fund's SpaceX deal will return $50B–$100B
“There's no doubt in a world where one investment might return 50 to a hundred Billion dollars. Everyone else has to feel just a teeny tiny tad irrelevant compared to that return for founders fund and good on them. It's a 20 year compounder at 50% plus or minus…”
Rory O'Driscoll: Anthropic will reach profitability and IPO while OpenAI faces overcommitment
“I think the difference between Anthropix and OpenAI is, OpenAI has more ambition, perhaps, but it's more likely to just get caught In the middle with commitments it can't meet. Whereas I think Entropic is very sensibly and boringly converging on profitability,…”