Mar 22, 2024 · 49m · more-or-less
#39: How (Not?) to Exit Your AI Company, Analyzing the New Google-Apple Tie Up · More or Less Podcast
Sam Lessin · 18m spoken Jessica Lessin · 17m spoken Brit Morin · 8m spoken Audio Engineer · 2s spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of the "More or Less" podcast, hosts Jessica Lessin, Brit Morin, and Sam Lessin analyze major industry shifts including Apple and Google's potential AI partnership, Microsoft's pseudo-acquisition of Inflection AI, and Reddit's IPO. They combine sharp corporate and venture critique with lighthearted discussions on emerging pop culture and wellness trends.
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 99.9% of the talking time here. How this is scored →
The hosts as informed peer 5.6 Guest teaching 2.6 Guest disagreement 3.3 The hosts pushing back 3.7
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 13:16 Sam rejects the rebel alliance narrative
Sam aggressively scoffs at Brit's framing of an Apple-Google alliance against Microsoft, ridiculing the idea that trillion-dollar monopolists could ever be viewed as rebels.
Hardest push from the hosts ▶ 28:48 Jessica challenges regulatory evasion in acquihiresJessica firmly challenges Sam's dismissive stance, insisting that Microsoft's talent deals are specifically structured to evade federal antitrust review and competition statutes.
Biggest teaching moment ▶ 38:36 Sam explains why data feeds make terrible business modelsSam educates the hosts on market fundamentals, detailing why one-off data licensing deals cannot sustain multi-billion-dollar public market valuations.
The host holds their own ▶ 23:00 Jessica details the mechanics of the Inflection buyoutJessica leverages direct reporting knowledge from The Information to detail the precise terms under which Microsoft returned capital to Inflection shareholders.
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 |
|---|---|---|---|---|---|---|
| Podcast Title Sequence and Opening Animation | 1 | 0 | 1 | 1 | Introductory banter about fashion, glasses, and setting the episode agenda in Dave Morin's absence. Completely lighthearted with minimal substance or tension. | |
| Apple and Google Gemini AI Talks: Hardware vs. Models | 7 | 3 | 3 | 4 | Jessica and Brit analyze the Apple-Google Gemini discussions, detailing Apple's on-device privacy strengths against Google's search and YouTube training index advantages. Sam offers contrarian views on Apple's product delay history and headset usage economics. | |
| Big Tech AI Alliances, Cloud Credits, and Circular Financing | 7 | 4 | 4 | 5 | Deep discussion on cloud credits and circular balance sheets between hyperscalers and AI startups. Sam dismisses the idea of a 'rebel alliance' while Jessica exposes how deals are structured with non-cash compute commitments. | |
| The Death of Software Venture Capital in the AI Era | 6 | 3 | 5 | 4 | Sam boldly declares that traditional software venture capital is dead due to commoditized code and massive capital moats. Brit and Jessica push back by noting emerging novel fund structures and execution risk. | |
| The Inflection AI Deal: Microsoft's Acquihire and Pi's Pivot | 8 | 4 | 3 | 4 | Jessica breaks down the unprecedented Inflection AI deal terms, explaining how Microsoft recruited Suleyman while compensating investors and avoiding traditional acquihire mechanics. Sam frames it as standard founder pivot dynamics. | |
| Regulatory Playbooks, Founder Ethics, and AI Talent Consolidation | 7 | 4 | 5 | 6 | Heated debate on regulatory evasion and founder ethics, with Jessica arguing Microsoft's move circumvents antitrust scrutiny while Sam defends founder self-interest and shutting down non-viable ventures early. | |
| Analyzing the Reddit IPO: Valuation, Community, and Data Licensing | 7 | 3 | 5 | 5 | Sam heavily dismisses banker marketing around Reddit's oversubscription and ridicules relying on data licensing for sports betting and AI training as poor-quality revenue. Brit and Jessica probe retail community interest. | |
| Pop Culture Corner: Reviewing A Brief History of the Future | 4 | 1 | 2 | 2 | Jessica reviews Catherine Murdoch and Ari Wallach's PBS series 'A Brief History of the Future', discussing pro-technology optimism versus dystopian tropes, met with mild teasing from Sam. | |
| Pop Culture Corner: Kate Middleton Sighting and Medical Leak | 3 | 1 | 2 | 2 | Lighthearted closing banter touching on Kate Middleton conspiracies, health supplements, creatine, and Brit's hydroponic garden berries. |
Statements from this episode (20)
Sam Lessin: Children's entertainer Blippi is worth around a billion dollars
“And he's worth like a billion dollars.”
Morin is extra long on Google in the AI race
“I think as everyone that listens knows, I'm extra long on Google in the AI race for a lot of reasons, but I'm also, I'm not short Apple.”
Morin: Apple delays product launches intentionally to observe and build privately
“Apple's typically behind on a lot of product launches on purpose. They kind of do like a watch and see and private build.”
Sam Lessin: Big tech outruns regulators by opening new fronts
“The companies have way more resources than the government to just continuously open new fronts. That then the regulators have to chase them on, right? So outside of extreme actions, it's clearly the game everyone's gotten wise to.”
Sam Lessin: Apple will release AI as developer APIs reinforcing hardware
“I think Dave made this point, you know, weeks ago. I think he's basically right, or the smart point, which is like, the way Apple would release this is a bunch of APIs for developers. That's the powerful move, right? Is to figure out effectively how to make th…”
Sam Lessin: Incumbents will capture AI value simply through higher profitability
“The big companies that have Distribution and data and business models, they generally just get more profitable, but that's about it.”
Jessica Lessin: Big Tech AI partnerships let giants mask their regulatory control
“Everyone's okay with this because it allows them to argue that they don't control I think any of these, you know, it allows them to argue their sphere of control is smaller than it kind of actually is”
Sam Lessin: Big Tech burning $100B on AI is worth it for downside protection
“The reality is, if any of these companies light even a hundred billion dollars on fire, Right. For downside protection of missing something, it's worth it to them.”
Jessica Lessin: Most of Microsoft's $10B OpenAI deal is cloud credits, not cash
“We saw it with Microsoft's huge, you know, ten billion dollar investment in OpenAI, huge portion of which isn't in cash. But it's in credits”
Lessin: Traditional software venture capital is dead
“The answer might be that software venture capital is dead. It's over.”
Morin: People will comfortably speak aloud to iPhones by 2024's end
“My prediction is by the end of this year, more and more people are just gonna be comfortable talking out loud to their iPhone.”
Lessin: Microsoft Repaid Inflection AI Early Investors Plus a Small Return
“What the information was able to report last night is a little bit more of the terms there. So it looks like Microsoft gave the early shareholders in inflection their money back, plus a little bit of a return and more to come on what that structure looks like.”
Jessica Lessin: Microsoft offered Sam Altman same deal as Inflection
“If Sam Altman hadn't gone back to OpenAI, this, he had a job offer to do exactly the same thing.”
Jessica Lessin: Big Tech AI acqui-hires are tailor-made to skirt antitrust
“There are laws designed to protect, you know, companies from getting so much market power that they're anti-competitive effects, and these deals are tailor-made to skirt those laws.”
Sam Lessin: Slow tells founders to shut down failing companies
“All the founders know that if you're working with offline and slow, we're gonna tell you to shut your fucking companies down when they're not working.”
Sam Lessin: Knowingly wasting employees' time on failing startups is a sin
“The absolute best thing a founder can do is call it and like pivot hard or shut it down, figure out who wants to be on the boat and get off and be honest with employees because it is like, from my perspective, I don't care about the money. The money is the mon…”
Sam Lessin: AI startup talent will recombine into Big Tech within years
“If you believe, as I do, that all the value is going to accrue to the top five players anyway, what you'd expect is that, like, on some non-zero timeline, but in the next few years, all the talent that got excited about these startup opportunities and went fly…”