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SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR

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 01:17 SpaceX’s $1.8T IPO: Genius Move or Disaster Waiting to Happen? 08:50 Day One vs Year One: Predicting SpaceX’s Future 15:51 OpenAI Files to Go Public — The Next Mega IPO? 18:27 Always-On AI: Is Persistent Memory the Future? 21:32 Apple Rebuilds Siri With Google AI — Smart or Surrender? 25:15 Uber Cuts 23% of HR 27:48 Robotaxis Are Back: Uber’s Autonomous Driving Bet 29:50 Revolut Hits $115B 31:29 Founder Fundraising Horror Stories & VC Grudges 39:47 Lovable & Cursor’s Explosive Growth: The New Startup Playbook 50:59 Did Elon Pull Off the Acquisition of the Year With Cursor? 53:25 Ramp’s $44B Valuation: Fintech’s Next Giant? 55:28 AI Music Startups Are Raising Massive Rounds — Why? 56:38 Where Is All This Money Coming From? The Risk-On Market Debate 59:33 The Surprising European Tech Success Story Nobody Saw Coming 01:04:48 Should Great Companies Even Go Public Anymore? 01:06:35 Data bricks, Mega Rounds & The Private Market Boom 01:08:58 Lightning Round: The Biggest Stories We Missed ---------------------------------------------------------------------------------------------- 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... ----------------------------------------------- Legal Disclaimer: The content of this podcast is for informational and entertainment purposes only and does not constitute financial or investment advice. Any discussion of stocks, public markets, or investment strategies reflects the personal opinions of the speakers and should not be relied upon when making investment decisions. Figures, valuations, and financial data referenced may be estimates or subject to error. Always consult a qualified financial adviser before making any investment decision. The views expressed are those of the individual speakers and do not represent the views of 20VC or its affiliates. ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #spacex #ai #openai #startups

Rory O’DriscollguestJason LemkinguestHarry Stebbingshost
Jun 11, 20261h 15mWatch on YouTube ↗

CHAPTERS

  1. 0:00 – 3:50

    SpaceX sets an unprecedented $1.8T IPO price upfront: what it changes

    The group breaks down SpaceX’s decision to pre-set the IPO price (around $135/share) rather than letting bankers run traditional price discovery. They discuss how this increases the odds of a messy first-day trade—up or down—because the usual “engineered pop” mechanism is removed.

    • Elon bypasses normal bookbuilding and price discovery by fixing the price early
    • Why early fixed pricing increases exposure to macro/news volatility before listing
    • What a typical IPO process does to maximize a first-day pop
    • How pre-pricing shifts the question from 'what’s the price?' to 'how much demand exists at that price?'
  2. 3:50 – 7:43

    Will it pop or break? Reading the early order book and subscription dynamics

    They examine indications that the IPO book is only ~2x covered and debate what that implies. Jason argues muted near-term trading; Rory notes that without banker-led price tuning, downside risk increases even if the company is extraordinary.

    • How to interpret '2x covered' in the context of an unusually large $75B raise
    • Why most IPOs seek 8–10x demand and what’s different at SpaceX scale
    • Downside break risk vs retail/day-trader enthusiasm driving a spike
    • Difference between tactical first-week trading and long-term fundamentals
  3. 7:43 – 11:01

    Day-one vs year-one: base rates, valuation gravity, and 'iconic company' reality

    They zoom out from mechanics to the bigger moment: an iconic technical company finally going public. Rory makes a 12‑month call that valuation may reassert; Jason predicts a possible “whimper IPO” but strong long-term appreciation tied to continued milestones.

    • Three plausible day-one scenarios: down, flat, or up—mechanics dominate
    • Rory’s view: 12 months later valuation likely lower as base rates bite
    • Jason’s view: weak debut doesn’t matter if execution keeps compounding
    • How huge IPO outcomes reshape LP expectations and founder/GP pressure
  4. 11:01 – 15:51

    Second-order effects: LP liquidity, co-investing, and rising performance expectations

    The conversation shifts to how giant liquidity events affect the broader VC ecosystem. They discuss LPs reinvesting more, co-investing behavior, and how fund size forces expectations for larger and larger outcomes.

    • Liquidity from a mega IPO can increase LP appetite for venture and direct deals
    • Why 'once-in-a-decade' outcomes distort return expectations across the stack
    • Fund size dictates required outcome size (venture math / 'arrogance index')
    • Debate: are mega outcomes becoming more frequent or just more visible?
  5. 15:51 – 18:07

    OpenAI files to go public: timing hedges, expectation management, and a crowded exit window

    They unpack why OpenAI would file while refusing to commit to a timeline. The panel frames it as expectation management while still pushing internally to move quickly, especially in a market that currently feels risk-on.

    • Why companies file early but avoid committing to a public timetable
    • The 'everyone’s gunning for the door' dynamic as capital needs explode
    • How SpaceX’s IPO outcome could influence OpenAI’s fundraising/IPO optics
    • Risk-on market conditions and the incentive to act while the window is open
  6. 18:07 – 21:39

    Always-on AI and persistent memory: from novelty to standard operating mode

    They debate Sam Altman’s push toward continuous, persistent AI and OpenAI’s 'Dreaming v3' memory upgrade. The key idea: memory improves user experience and potentially reduces token/context overhead, pushing AI beyond a browser-bound tool into an ambient layer.

    • Why non-persistent, browser-based AI will feel archaic soon
    • Memory as part of the 'harness' around models: usability + cost efficiency
    • Token economics: reducing repeated context can lower inference costs
    • How persistence changes product expectations for both consumers and enterprises
  7. 21:39 – 24:37

    Apple rebuilds Siri with Google’s AI: pragmatism, context advantage, and consumer realities

    They react to Apple paying Google to power Siri-like experiences and whether that signals surrender. Rory argues it’s a pragmatic catch-up move: Apple’s real advantage is device context and consumer UX, not owning the frontier model.

    • Apple’s priority: deliver delightful consumer experiences, not win model benchmarks
    • Device context (calendar, identity, intent) as a powerful differentiator
    • Consumer AI market challenge: 'consumers don’t want to work'—they want experiences
    • Competitive implications for OpenAI’s consumer strategy vs Anthropic’s enterprise focus
  8. 24:37 – 27:42

    Uber cuts 23% of HR: what AI can (and can’t) automate in knowledge work

    They discuss Uber’s HR layoffs alongside claims that AI wasn’t a driver, despite broad internal AI usage. Jason argues HR is ripe for AI augmentation; Rory doubts AI alone explains a 23% cut and emphasizes the broader question of task vs job automation.

    • Why recruiting/HR are often the first functions cut in downturns or reorganizations
    • Case for AI-augmented HR: consistency, auditability, bias reduction (in theory)
    • Rory’s calibration: adoption outside engineering lags; 23% feels high for pure AI savings
    • The core question: automation of tasks vs elimination of whole roles
  9. 27:42 – 29:44

    Robotaxis return to the thesis: Uber’s autonomous driving partnerships and existential risk

    The panel flags robotaxis as the more strategically important Uber thread. They argue the timeline is slower than early hype, but Uber’s platform could remain central if it becomes the coordinator for multiple autonomous fleets.

    • Uber’s renewed robotaxi experimentation (e.g., Madrid) via partners
    • Why autonomous driving is one of the biggest labor automation targets
    • Two futures: robotaxis as existential threat vs Uber as fleet aggregator
    • The long arc: slow, steady progress rather than sudden overnight tipping points
  10. 29:44 – 31:29

    Revolut at $115B: fintech wins where incumbents are weakest

    They celebrate Revolut’s scale while explaining why fintech valuations correlate with how badly incumbents price and serve customers. Rory contrasts Europe’s weaker bank UX (bigger opening for Revolut) with the U.S. market, where fintech outcomes can be smaller due to stronger incumbents.

    • Revolut’s value as a mirror of incumbent inefficiency and consumer pain
    • Why European banking structure/fees created a massive wedge for challengers
    • Comparison to Chime and Nubank: opportunity size varies by market failure
    • Caveat: long-term lending and the broader banking system role
  11. 31:29 – 39:47

    Founder fundraising horror stories & VC grudges: rejection, scars, and sales reality

    They respond to viral threads of founders recounting bad VC experiences, including the Cloudflare/Khosla story. Jason stresses founders hold grudges more than VCs, and fundraising is sales; Rory adds that rejection feels personal because founders are selling themselves.

    • Why fundraising rejection cuts deeper than product sales rejection
    • VCs say no to ~99% of deals—structural dissatisfaction is inevitable
    • When grudges are justified (e.g., being fired) vs when to move on
    • Direct feedback about team balance: sometimes useful, often poorly delivered
  12. 39:47 – 50:58

    Lovable & Cursor’s explosive growth: ultra-lean startups, token costs, and the new efficiency bar

    They analyze staggering ARR-per-employee numbers and what it means for company-building. Jason argues founders now aim for $1M+ revenue per employee; Rory notes many AI-native companies substitute labor with heavy token/inference spend, changing margin structure and headcount needs.

    • Why extreme revenue-per-employee is becoming an explicit founder goal
    • The trade: fewer employees but high 'intelligence' (token) cost structure
    • PLG vs enterprise sales: lean models work best when distribution is product-led
    • Prediction: many startups will be ~half the headcount of prior generations at similar revenue
  13. 50:58 – 53:25

    Elon’s 'acquisition of the year' (Cursor) and the compute pivot: from model struggles to infrastructure wins

    They argue Elon turned a perceived AI weakness into strength by building massive compute capacity and landing large external customers—then adding Cursor to backfill demand. The framing: even if the foundation model lags, owning scarce compute and high-usage apps can create a powerful economic engine.

    • Compute-first strategy: build capacity ahead of demand to capture the wave
    • Revenue flywheel: selling compute to major AI labs + owning a high-usage app
    • Cursor acquisition economics: paying a high multiple if growth targets land
    • Distinction between being a top model provider vs being the best 'CoreWeave-like' supplier
  14. 53:25 – 59:33

    Mega private rounds (Ramp, Suno) and the 'where is all the money coming from?' risk-on debate

    They discuss Ramp’s $44B valuation and Suno’s rapid repricing as examples of aggressive risk-on behavior. Rory frames fintech valuation as financial-multiple-plus-growth; Jason likes Suno’s product but questions whether the trajectory justifies such fast doubling without seeing the durable endgame yet.

    • Ramp valuation logic: growth-adjusted financial services multiple
    • Suno’s momentum: impressive utility, but questions about durability and pricing power
    • Market psychology: money doesn’t disappear—confidence does ('money gets scared')
    • Broadcom/chip guidance as a reminder that 'priced for perfection' markets snap on small misses
  15. 59:33 – 1:15:55

    Bending Spoons’ roll-up machine and the late-show lightning round: private market boom, Databricks, and model consolidation

    They examine Bending Spoons’ consumer roll-up strategy (cut costs, raise prices, acquire growth) and debate whether markets care about organic vs inorganic expansion. They close with broader themes: Databricks staying private despite massive valuation, Microsoft’s models as a strategic necessity, and why model consolidation vs open ecosystems matters for the whole stack.

    • Bending Spoons as 'Vista/Thoma Bravo for consumer': cost cuts + price increases
    • Debate: quality of turnarounds vs financial engineering; valuation skepticism vs admiration
    • Databricks: reasons to avoid IPO (capital need, currency, liquidity) and why private markets can be cheaper/higher-multiple
    • Microsoft shipping its own models: strategic control even if not frontier-best; consolidation risk and the need for non-China open-source competitors

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