May 9, 2025 · 56m · more-or-less
OpenAI Acquires Windsurf for $3B, Google's Stock Dips | #98 · More or Less Podcast
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In episode 98 of the 'More or Less' podcast, hosts Jessica Lessin, Brit Morin, and Dave Morin evaluate tech's latest consolidation wave led by OpenAI's Windsurf acquisition, unpack Google's AI search crisis, and explore a cultural shift back toward analog experiences.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. The hosts hold 100% of the talking time here. How this is scored →
The hosts as informed peer 6.0 Guest teaching 2.9 Guest disagreement 2.5 The hosts pushing back 3.0
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 39:56 Jessica dismisses Marc Andreessen's VC exceptionalism
Jessica openly scoffs at Andreessen's claim that venture capital requires unique human empathy that AI cannot disrupt, comparing it to Blockbuster rationalizing VHS rentals.
Hardest push from the hosts ▶ 26:49 Brit checks Dave on Google stock performanceWhen Dave attempts to dismiss Google's stock dip as sideways movement, Brit firmly corrects him with market data showing a 25% drop and an $150 billion market loss in a single day.
Biggest teaching moment ▶ 15:48 Dave critiques novice vibe coders' architectureDave recounts diagnosing an amateur vibe coder's sluggish app to reveal they used two massive CSV text files as a database instead of Core Data tables.
The host holds their own ▶ 34:48 Jessica details reporting on Apple's internal AI strugglesJessica draws upon The Information's reporting to assert that Apple's internal LLM efforts are chaotic and ill-prepared to match standalone AI search engines.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The hosts as informed peer | Guest teaching | Guest disagreement | The hosts pushing back | Why |
|---|---|---|---|---|---|---|
| Episode Welcome and Countdown to Episode 100 | 5 | 3 | 1 | 2 | The co-hosts engage in lighthearted banter around Dave Morin topping Stanford's historical unicorn angel investor list. Dave explains the likely cap-table methodology behind individual rankings while Brit points out the absence of female angel investors. | |
| M&A Wave and OpenAI's Windsurf Acquisition | 6 | 2 | 2 | 2 | The conversation shifts to the M&A landscape, focusing on OpenAI acquiring Windsurf for $3B alongside Cursor's valuation bump. Dave analyzes why developer-layer tools are strategically acquirable while foundational models dominate the app layer. | |
| The Reality of Vibe Coding and Engineering Impact | 7 | 4 | 3 | 3 | Jessica raises reports of engineer backlash against 'vibe coding', which Dave grounds with firsthand board-level feedback from a VP of Engineering on production crashes and non-architectural coding mistakes. Brit also highlights tools like Bubble and Lovable bridging the gap for non-engineers. | |
| M&A Valuations and the Analog Media Renaissance | 5 | 2 | 2 | 3 | Jessica and Brit debate whether digital media M&A is undervalued or dead, prompting Brit to advocate for an analog print renaissance. Jessica counters Dave's bullish digital media stance by pointing out lack of acquirers. | |
| Apple AI in Safari and Google's Search Crisis | 7 | 4 | 4 | 4 | Discussing Eddy Cue's antitrust testimony regarding Apple evaluating AI search to replace Google in Safari, Dave claims Google stock has traded sideways while search collapses. Brit and Jessica push back with hard figures, noting Google's stock plunged 25% from its highs and 8% in a single day. | |
| Netflix UI Overhaul and the TikTokification of Streaming | 4 | 2 | 1 | 2 | The hosts break down Netflix's UI overhaul toward short-form, TikTok-like previews and natural language searching. The tone is collaborative and comedic as they review user personalization and recommendation algorithms. | |
| Coatue's Retail Fund and Marc Andreessen on AI | 8 | 3 | 4 | 5 | The panel assesses Coatue's $50k retail evergreen vehicle, parsing whether it democratizes investing or exposes an LP capital crunch among endowments. Jessica fiercely dismantles Marc Andreessen's assertion that venture capital will be immune from AI automation. | |
| Barry Diller's New Memoir and Jessica's Media Cameo | 6 | 3 | 3 | 3 | Jessica shares her connection to Barry Diller's upcoming memoir before the group analyzes why tech luminaries were absent from the Met Gala. Dave contends that technology merely distributes art rather than generating organic culture. |
Statements from this episode (21)
Lessin: DoorDash Acquired Deliveroo for Just Under $4B
“DoorDash bought Deliveroo leading delivery, food delivery service in the UK for I think just under four billion.”
Brit Morin: DoorDash Is Acquiring SevenRooms for $1.2B
“DoorDash is also acquiring seven rooms for 1.2 billion.”
Brit Morin: OpenAI acquired AI coding startup Windsurf for $3B
“Windsurf obviously got sold to OpenAI for three billion.”
Dave Morin: Windsurf Is the First Big AI Acquisition
“This one kind of is the first, it's the first big acquisition in, in AI land.”
Brit Morin: Cursor raised approximately $900M at a $9B valuation
“Cursor raised like nine hundred million this week for at a nine billion dollar valuation, I believe.”
Brit Morin: AI will supercharge, not replace, senior software engineers
“The sort of senior software engineer that's based inside of some of these very large tech companies, I don't think are going to be replaced anytime soon. As much as they will be augmented and able and supercharged, which is just like the rest of what AI is doi…”
Dave Morin: Digital media is the most undervalued asset class right now
“I think digital media is the most undervalued asset class right now.”
Jessica Lessin: There will not be a wave of digital media acquisitions
“I'll make the bold predictions that you will not see a wave of digital media acquisitions.”
Brit Morin: The New York Times has surpassed 11M subscribers
“New York Times passed eleven million subscribers, so they're still growing.”
Dave Morin: Search is dying as query volumes drop 45% to 50%
“I think it's okay to actually say search is dying. I've seen enough data in the last two or three weeks that suggests this is the case that it's actually, I mean, we're not talking about little two percent dips. We're talking about 45, 50% dips. Like these are…”
Lessin: Internal reporting reveals Apple's LLM efforts are in complete disarray
“Apple really It needs, if it's going to be in the sort of LLM type game in search and AI, as opposed to like optimizing cool on device use cases, it's really got up its game. And by all accounts, all our reporting of the information just shows a huge freaking …”
Lessin: Courts Likely to Bar Apple-Google Search Deal in Current Form
“The courts are likely to say that the Apple Google search deal cannot continue in its current form for antitrust reasons.”
Brit Morin: Google stock dropped 25%, shedding $150B in one day
“No, it's dropped from like two Oh seven to currently one 52. So that's like 25%. Today it dropped eight percent alone, which on like a two trillion dollar market cap companies, like a hundred and fifty billion dollars, which is just crazy.”
Brit Morin: Netflix UI redesign adds TikTok-style video clip feeds
“There's also video shorts that you can click on to sort of watch trail. It's not trailers. They're like shorts. They're clips from the shows that are in like a TikTok like feed that then you can click in and watch the show.”
Lessin: Coatue launches $1B permanent capital fund with a $50K minimum
“Led by Philippe, they announced something that is, I think a bill, it's anchored with a billion dollars from Bezos and Michael Dell. But the premise is that they will accept investments for the relatively low capital amount of 50 K, which is traditionally a mu…”
Dave Morin: The S&P 500 outperforms almost all venture capital funds
“If you've got an incremental dollar, putting it into the S into an S and P 500 index fund for the most part performs better than almost all of the venture capital asset class.”
Morin: Trump Administration Endowment Threats Have Blown Up VC Deals
“And, you know, now you've got the Trump administration threatening to decimate college endowments. We know we've already seen this blow up many different deals across the venture capital ecosystem in the last few weeks.”
Dave Morin: Seed to Series A Graduation Rate Down Over 25%
“If you look at the number of series A's graduating from the seed ecosystem, it's down like over 25% now.”
Lessin: 2025 Met Gala Had Virtually No Silicon Valley Startup Presence
“And it wasn't like Silicon Valley flood the Met Gala, but like there was, you know, the cool, you would, it would not be out of place to see the cool, young, fashionable startup dude who was sort of in with that crowd. And it was sort of none of that this year…”