Podcast Summary

Podcast: The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Host: Harry Stebbings
Guests: Jason Lemkin, Rory O'Driscoll
Episode Title: Will SpaceX IPO at $1.5TRN | Will Cursor Kill Figma | Lightspeed Raises $9BN | OpenAI: $1BN from Disney, New CRO & #1 App in App Store | Oracle and Broadcom Hit: Now the Time to Buy?
Date: December 18, 2025

Episode Overview

In this dense and spirited episode, Harry Stebbings convenes Jason Lemkin (SaaStr) and Rory O’Driscoll (Scale Venture Partners) to dissect a blockbuster week in tech and venture capital. Major topics include multi-billion-dollar fund raises in VC, the delayed IPO supercycle and its implications, aggressive moves by AI leaders like OpenAI and Anthropic, the shifting sands beneath legacy SaaS/tools as AI-native competitors rise, and whether SpaceX could IPO at a stratospheric $1.5 trillion. The crew also examines the knock-on market effects on giants like Oracle and Broadcom, and closes out with high-level “would you rather” debates on valuations and industry leadership.

The trio’s conversation is insightful, fast-paced, and laced with irreverence—a must-hear for anyone wanting to understand the tectonic shifts driving today’s innovation economy.

Key Discussion Points & Timestamps

1. Lightspeed’s $9 Billion Raise: Venture’s Barbell Gets Heavier

• [05:02 – 11:10]
• Lightspeed raised $9B across six funds—$2B for venture/early, $7B for growth and other strategies.
• Jason Lemkin: “It just continues to contribute to the barbell side of venture.” [05:33]
• Multi-stage VCs' ability to pay at seed makes it harder for pure-play seed funds.
• True success as a large manager now means: (a) early-stage winners over 10+ years and (b) huge late-stage conviction ("stuffed a ton of money in the hot late stage deals").
• Multi-stage dominance is undermining traditional seed economics.
• Lemkin sees declining LP appetite for new early-stage managers since 2021: “I don’t actually see that appetite… I don’t see a resurgence.” [08:48]
• The supercycle is still “all about private companies staying private—the greatest gift to venture in our lifetime.” [11:10]

2. The Private IPO “Supercycle” and Retail Investor Lockout

• [11:10 – 13:44]
• Venture funds now reap exceptional compound returns from late-stage investments in companies like OpenAI, SpaceX, Databricks.
• Harry Stebbings: “All that value has been taken in the private arena… it’s been great for late-stage firms.” [12:05]
• Comparison of then-vs-now: Tesla IPO’d at $1.7B; SpaceX prepping for $1.5T IPO. It’s “a thousand x more.” [13:09–13:44]
• The “cost of capital” now is lower in private markets, a key shift in why companies are delaying public listings.

3. OpenAI’s Big Week: Disney Partnership, CRO Hire, App Store #1

• [14:15 – 18:49]
• Disney announces a $1B investment in OpenAI (largely cross-licensing/IP; not transformative cash).
• Harry Stebbings: “It’s fairly experimental for Disney... we’re effectively getting a billion dollars in equity in return for allowing these guys to play with our characters.” [14:58]
• Markers of the new AI + IP template—Disney experimenting while sending Google a cease & desist (for unlicensed use).
• OpenAI’s app becomes the most downloaded in the US ("the moat is 800 million users"). [18:05]
• Discussion on proprietary IP vs. open content and future economic returns.

4. OpenAI vs Anthropic vs Gemini: The AI Platform Horse Race

• [18:49 – 22:24]
• Can OpenAI retain its lead as growth slows and the "law of large numbers" sets in?
• Jason Lemkin: “There is nothing as terrifying as a high-growth bet that slows down… you go from being valued on growth to being valued on cash flow.” [21:30]
• OpenAI ends cliff vesting due to intense hiring competition and extraordinary sums of money being offered (“maybe at the current rate, I'm vesting on 2 or 3 million bucks…” [22:32])
• The risk of sudden valuation resets if growth slows while private.

5. Oracle and Broadcom Hit: AI Megatrend or Margin Canary?

• [24:24 – 33:42]
• Oracle shares plunge ~45%; Broadcom loses $300B+ in two days off Anthropic chip order worries.
• Oracle’s “sugar high” from major cloud contracts now confronted with immense capex (“you just opted to enter a very capital-intensive…data center business… with someone who may or may not be able to afford to pay”). [24:51]
• Jason Lemkin: “They’re at high risk of margin compression… but overall trend is still anti-gravity.” [26:23]
• Discussion of market volatility as necessary truth-finding about the AI narrative.
• On Broadcom and Anthropic: lower chip margins expected compared to Nvidia; market gets “excited about revenue, less excited about EPS.” [30:09]
• Broader implication: Not all AI supply chain players get a free pass on margins.

6. Cursor’s AI Coding Power Play: Will It 'Maim' Figma?

• [36:08 – 49:00]
• Cursor’s new UI for coding—blurring lines between design and development tools.
• Jason Lemkin: “AI is creating convergence where the same products can do more things… you shouldn’t have different tools for design, prototyping, and production. The agents are just too good.” [36:41]
• Figma is slow to respond, risk of being “maimed” rather than killed: “Logo retention remains good, but NRR drifts down and new customers…defer that purchase.” [47:45]
• The “meta agent” vision: unified tools spanning multiple silos of the software process.
• Move to “outcome” based enterprise software—AI sees the customer rather than departmental silos.
• Jason calls out the risk for many SaaS leaders: “A lot of founders aren’t being honest about how they’re being maimed by AI leaders.” [48:49]

7. Mauling the Incumbents: How AI is Reshaping B2B SaaS

• [49:00 – 54:38]
• Many public SaaS names are being “maimed”—slow growth, pressured expansion, e.g., Atlassian, GitLab, MongoDB, UiPath.
• Jason Lemkin: “It’s this maiming that I think people aren’t— a lot of founders aren’t being honest about how they’re being maimed by AI leaders. They’re not being crushed, they’re being maimed.” [48:49]
• The “refounding” imperative: B2B leaders need to drive through agentic, AI-first upgrades into their customer base—rapidly.

8. Moonshots, Deep Tech, and SpaceX’s $1.5TRN Manifestation

• [56:24 – 72:35]
• Boom Supersonic: pivot from planes to selling generators to data centers—“walk into the factory and say, strip those engines off those planes…make them generate electricity for a data center.” [59:45]
• SpaceX’s $800B secondary round and rumored $1.5T IPO.
  • Harry Stebbings: “You can’t run the numbers on SpaceX and come up with 1.5 trillion. You just can’t. But what you can say is someone who’s… literally might find you another trillion-dollar market.” [61:45, 64:14]
  • “EOV: Elon Option Value”—the premium on Elon’s ability to create new, game-changing markets.
  • If EOV ever evaporates, look out.
• Narrative and "manifesting" as core to mega-unicorn valuations: “He’s manifesting a 1.5 trillion dollar company… he’s doing it.” [64:14]
• Who buys at $1.5T? “You’re asking me to assess something that’s not within the bounds of logic.” [67:40]
• Importance of key backers (Google, Nvidia, Fidelity) to build deal momentum: “All of a sudden you start to panic that you’re not going to get your shares.” [70:28]
• Founders Fund/Thiel–Elon story: “Be kind. It may just pay off. Like owning 10% of a $1.5 trillion IPO…” [72:35]

9. Lightning Round: Figma vs Cursor / OpenAI vs Anthropic vs Google

• [74:31 – 77:59]
• Figma at $17B vs Cursor at $29B? Both Jason and Harry lean Figma, but acknowledge nothing is stable.
  • Jason Lemkin: “We are so early in AI that... there was a lot less stability in these so-called leaders than we thought.” [75:18]
• OpenAI at $500B, Anthropic at $360B, Google at $2T?
  • Jason: “I have to take Google… just the level of ... confidence I see across the team.”
  • Harry: “I think I'd go Anthropic… they're converging on profitability, will go public, will be a very nice public company.” [77:13]

Notable Quotes

• “You can’t run the numbers on SpaceX and come up with $1.5 trillion. You just can’t.”
  — Harry Stebbings, [61:45]

• “There is nothing as terrifying as a high-growth bet that slows down.”
  — Jason Lemkin, [21:30]

• “AI is creating convergence where the same products can do more things… You shouldn’t have different tools for design, prototyping, and production. The agents are just too good.”
  — Jason Lemkin, [36:41]

• “All that value has been taken in the private arena… it’s been great for late-stage firms.”
  — Harry Stebbings, [12:05]

• “It’s this maiming that I think people aren’t— a lot of founders aren’t being honest about how they’re being maimed by AI leaders. They’re not being crushed, they’re being maimed.”
  — Jason Lemkin, [48:49]

• “Manifesting a $1.5 trillion company. I don't know if all the kids can manifest it, but… he's doing it.”
  — Jason Lemkin, [64:14]

Segment Timestamps

• [05:02] Lightspeed’s $9B: impact on venture, seed market dynamics
• [11:10] Delayed IPO cycle is gift to late-stage VC; public market lockout
• [14:15] OpenAI: Disney, app, exec hires; IP licensing
• [18:49] AI app platform battle: OpenAI, Gemini, Anthropic
• [22:32] OpenAI kills vesting cliff; high-stakes comp in AI
• [24:24] Oracle/Broadcom market shocks—AI capex risk
• [36:08] Cursor AI—convergence, risk for Figma/design stack
• [47:29] AI ‘maiming’ incumbents; SaaS retention, expansion headwinds
• [56:24] Deep tech: Boom Supersonic, hard tech risk, moonshot IPOs
• [61:45] The EOV (Elon Option Value); SpaceX’s mega-IPO narrative
• [74:31] Figma vs Cursor, OpenAI vs Anthropic vs Google

Memorable Moments

• Cursor vs Figma Debate:
  “The bigger risk for so many vendors is that it maims Figma. Not the old customers don't leave... the new guys are just taking enough of the new budget that your growth materially decreases.”
  — Jason Lemkin [47:45]

• The Grand Challenge of IPO-ing SpaceX:
  “Is there $120 billion of raw risk capital that says what I really need in my portfolio in 2026 is some 70x run rate revenue space investments?”
  — Harry Stebbings [69:06]

• Kindness Pays, Literally:
  “Be kind. It may just pay off. Like owning 10% of a $1.5 trillion IPO, even for a billionaire. It might pay off.”
  — Jason Lemkin [72:35]

• Refounding in the Age of AI:
  “You just got to say we are refunding the company in the age of AI. We are not going to lose any of these AI-first deals and we're going to make it happen.”
  — Harry Stebbings [51:10]

TL;DR Flow

• Mega VC funds are getting bigger, crowding out early-stage pure plays.
• The delayed IPO cycle means late-stage VCs are compounding massive returns—public investors are left out.
• OpenAI’s big week includes a Disney partnership (primarily IP licensing) and top app store ranking, but user growth is plateauing.
• Figma and similar SaaS leaders face existential and ‘maiming’ threats from AI-native upstarts like Cursor.
• Market volatility hits Oracle and Broadcom, as investors debate who really benefits in the AI gold rush.
• Deep tech moonshots (SpaceX, Boom Supersonic) are back—SpaceX prepping to IPO at $1.5T, but most of that value is pure “Elon Option Value.”
• Founders and legacy SaaS leaders must “refound” their businesses around AI or risk stagnating.
• Segment closes with lightning-round takes on Figma vs Cursor and OpenAI vs Anthropic vs Google.

For the full episode, show notes, and to learn more, visit 20VC.com.