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Will Cursor Kill Figma? Lightspeed Raises $9B & OpenAI’s $1B from Disney & #1 App in App Store

Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more. Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as Bill.com (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others. ----------------------------------------------- Timestamps: 00:00 Intro 01:19 Lightspeed's $9 Billion Fundraise 06:20 The Impact of Mega Funds on Seed VCs 11:28 The Supercycle of Growth and Late-Stage Investments 14:01 Disney Invests $1BN into OpenAI and What It Means 21:46 Oracle Hit Hard: Is Now the Time to Buy 27:23 Broadcom's Market Cap Drop and Anthropic's AI Chip Orders 34:40 Cursor Competes with Figma: The Convergence of Design & Coding Tools 47:02 The Biggest Danger for Incumbents: Being Maimed by AI 56:43 Boom Supersonic Raising $300M to… Power Data Centres… WTF 01:02:23 Will SpaceX IPO at $1.5TRN and The Elon Option Value 01:17:17 Would You Rather… ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: https://x.com/harrystebbings Follow Jason Lemkin on X: https://x.com/jasonlk Follow Rory O’Driscoll on X: https://x.com/rodriscoll Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/con... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #openai #spacex #lightspeed #disney #figma #cursor #elonmusk

Rory O’DriscollguestJason LemkinguestHarry Stebbingshost
Dec 18, 20251h 21mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Mega-funds, AI platform shifts, and SpaceX’s valuation narrative collide

  1. Lightspeed’s $9B raise is framed as a multi-stage play where seed pricing matters less than securing access to later, concentrated bets on potential $100B+ outcomes.
  2. Late-stage AI investing is described as a new “growth supercycle” amplified by delayed IPOs, which keeps compounding gains (Databricks, SpaceX, OpenAI/Anthropic) in private markets and away from public investors.
  3. Disney’s reported $1B OpenAI deal is treated as an early template for paid IP licensing in generative AI, signaling a shift from scraping-era dynamics to negotiated content economics.
  4. Market reactions to Oracle and Broadcom illustrate growing scrutiny of AI-adjacent businesses where CapEx intensity and gross-margin dilution can overwhelm headline revenue wins.
  5. Cursor’s move toward design highlights rapid AI-driven category convergence, with the biggest incumbent risk being “maiming” (NRR and new-budget erosion) rather than sudden churn-driven collapse.

IDEAS WORTH REMEMBERING

5 ideas

Mega-funds turn early checks into strategic access, not valuation discipline.

The panel argues that when a platform fund is measured on $100B outcomes, paying $30–50M pre at seed becomes an “entry ticket” to win follow-on rounds, reinforcing a barbell where a few winners drive returns.

The “no IPO” era is a structural tailwind for late-stage venture returns.

Keeping elite companies private longer lets growth investors deploy huge dollars with venture-like upside, while public-market/retail investors miss the steepest compounding phase (e.g., Databricks, SpaceX).

In AI infrastructure, revenue announcements can be sugar highs if CapEx and margins deteriorate.

Oracle’s OpenAI-driven commitments highlight how exciting RPO/backlog can reverse when markets price in the cost to deliver—especially in capital-intensive data center buildouts.

Custom silicon demand can still be ‘bad news’ if it signals margin compression.

Broadcom’s selloff is framed as a rational repricing: customers like Anthropic pursue alternatives to Nvidia precisely to pay less, so headline orders may come with structurally lower gross margins.

Paid IP licensing may become a defensibility lever for consumer AI fronts.

Disney’s deal is interpreted as a precedent-setting negotiation: top-tier IP could create switching friction for consumer chat/image products, and later entrants may face worse terms as rates ratchet up.

WORDS WORTH SAVING

5 quotes

All these leaders not IPO-ing is the greatest gift to venture in our lifetimes. It's playing the growth supercycle bet today. That's the winning play.

Jason Lemkin

There is nothing as terrifying as a high-growth bet that slows down.

Rory O’Driscoll

I think what we're, what, what, uh, all of us need to be hyper-aware of in '26 and '27 is massive convergence of categories.

Jason Lemkin

I think the bigger risk for so many vendors is that it maims Figma.

Jason Lemkin

What I realized is you have to factor in what I'm now gonna refer to as the EOV, the Elon Option Value. You can't run the numbers on SpaceX and come up with the 1.5 trillion. You just can't, right?

Rory O’Driscoll

Lightspeed $9B fundraising mechanics (venture vs growth vehicles)Barbell venture outcomes and seed economics under multi-stage pressureDelayed IPOs and private-market compoundingDisney–OpenAI IP licensing as a content templateOracle/CoreWeave as high-beta AI infrastructure betsBroadcom custom chips and margin compression fearsCursor vs Figma and design–code convergenceIncumbents being “maimed” by AI (NRR drift, slower new logo growth)Boom Supersonic pivoting engines toward data-center powerSpaceX IPO rumors, valuation logic, and “Elon Option Value”

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