Digital Disruption with Geoff Nielson (Info-Tech Research Group)

Episode: “Siri Creator: How Apple & Google Got AI Wrong”

Guest: Adam Cheyer, Co-founder of Siri

Date: August 25, 2025

Episode Overview

This episode features Adam Cheyer, the pioneering co-founder of Siri, in a probing conversation about the present and future of artificial intelligence, digital assistants, and their impact on technology and society. Cheyer reflects on how AI’s trajectory deviated from early visions, what’s fundamentally missing in today’s AI products, and where the true “magic moments” of technology still lie ahead. He offers candid insights on design, ecosystem, the role of government research, timing, and the next paradigms of computing—touching on everything from AR to collective intelligence.

Key Discussion Points & Insights

1. The Current State & Limitations of AI (00:00–08:28)

• Cheyer’s Perspective on Modern AI:
  Adam Cheyer is both "amazed and frustrated" by today’s generative AI, noting that language models like ChatGPT excel at knowing but are poor at doing (executing tasks) and integrating with real-world services.
  • “On the knowing side, ChatGPT is incredible, but ... it just feels so wrong and broken and just the wrong direction.” (B, 02:44)
• Siri vs. ChatGPT Functionality:
  While ChatGPT trumps Siri in conversation, Siri integrated with personal services—something current LLMs don’t do:
  • “With Siri, I can say, hey Siri, tell my wife I’m going to be late. Can ChatGPT do that? ... Oh, no, it can’t send a message to my wife.” (B, 01:50)

2. Three Big Missing Pieces in Today’s AI (03:50–08:28)

Cheyer identifies three core challenges that must be solved together for AI assistants to achieve their promise:

A. User Interface is All Wrong

• Most AIs rely on text-chat, whereas tasks like travel require visual, graphical interaction.
• “Travel is emotional, it’s visual. You want to work with maps and timelines like you need visual information. Having a text chat to do that type of task is ... a bad experience.” (B, 04:32)

B. Knowing vs. Doing

• LLMs are “know-it-alls” based on pre-trained, cached data. Real-task execution (doing) requires trustworthy API access, real-time calls, and authentication—barely addressed so far.
• “Users don’t make a distinction … What’s the right architecture that combines both?” (B, 06:33)

C. The Ecosystem/App Store Analogy

• There’s no “app store” for AI—no open, standardized marketplace enabling companies to plug in differentiated services.
• “Service providers want things like brand ... They want to own the user … What’s the AI equivalent?” (B, 07:23)

3. Siri’s Original Vision & Apple’s Missed Opportunity (08:51–11:30)

• Siri was designed with all three elements in mind: balanced GUI and language, APIs for doing, and an open ecosystem.
• Steve Jobs’ death halted the app-store-like vision for Siri—Cheyer emphasizes how the lack of open ecosystem stunted its potential.
  • “[The ecosystem] was always, for me, the whole point of Siri, got left on the cutting room floor after Steve Jobs died.” (B, 09:04)
  • Jobs delayed his passing to witness Siri’s launch—an emotional detail underscoring the vision’s importance. (B, 09:39)

4. Paradigm Shifts and the 10+ Theory (11:30–15:37)

• Cheyer’s “10+ Theory”: Every 10–12 years, a major interaction paradigm emerges:
  • 1984: GUI/mouse
  • 1995: Web browsers
  • 2007/8: iPhone/App Store
  • 2021: Conversational AI (his prediction)
  • 2035: Augmented reality (“the next major paradigm shift”)
  • “To be a paradigm scale system, you need the right interface, you need knowing and doing, and you need an ecosystem. All of these have that.” (B, 13:31)
• AR will only deliver on potential when the user experience, APIs, and marketplace are integrated as in previous tech revolutions.

5. AR’s Future & The Nature of “Killer Apps” (15:37–20:06)

• Cheyer argues the future isn’t about a single “killer app,” but about a “killer OS”—a paradigm that makes new forms of computing natural and widespread.
  • “I always think about the killer OS. It’s a framework, a paradigm for doing things that is better than the way we can do computing today.” (B, 16:34)
• Screens will become obsolete as AR matures; physical and digital worlds will blend seamlessly.

6. Multimodal Design & Principles for Ubiquitous Computing (20:06–30:19)

• Good design means integrating the right input/output modes for context: touch/typing for what’s visible, language for what’s not.
  • “If it’s on the screen, the best way is to interact with it. If it’s off the screen, the best way is to ask for it.” (B, 22:12)
• Original Siri supported type, tap, and talk—maximizing beginner and expert usability, a lesson lost in modern assistants.

7. The Lost Art of “Beginner” Experience (25:00–32:51)

• Cheyer highlights how “speech is an expert modality,” and modern assistants ignore the discovery needs of beginners, making them less approachable.
  • “A spoken interface you can't discover. Speech is an expert modality. In a sense, it’s not a beginner. You can’t browse, you can’t discover.” (B, 27:14)
• Original Siri offered menus, semantic autocomplete, and contextual suggestions—ways to guide and educate users.

8. The Path Forward: Blending GUI and Language (32:51–36:36)

• The future is a seamless blend of graphical and conversational interfaces, not one replacing the other.
  • “You will use a mix of GUIs and language in the seamless, perfect way … users don’t have to think about which they’re doing.” (B, 23:21)
• Cheyer likens the current AI landscape to the early web: great at some things, lacking in interactivity and real-world impact, but poised to mature.

9. “Magic,” Design, and Entrepreneurship (37:35–43:55)

• Cheyer draws parallels between magic and entrepreneurial technology reveals—citing Steve Jobs’ keynote trickery as a lesson in building anticipation and desire.
  • “There are lessons in magic about how to present your products and your tech systems in a way that makes people feel, that builds anticipation, that creates wonder.” (B, 38:00)
• The “magic” of AI and breakthroughs is always a moving target; what wowed us yesterday soon becomes ordinary, as with Deep Blue and early Siri.

10. Timing, Trends, and the Next Big Shift (43:55–47:00)

• Cheyer’s “superpower” is timing—spotting the right moment for breakthrough products (Siri, Change.org, Viv Labs, Sentient).
• Today’s AI will soon become “boring infrastructure,” like the web; the real magic is likely to happen in areas adjacent to, but not identical with, mainstream AI.

11. The Next Frontier: Collective Intelligence & The Role of Research (47:10–54:20)

• Beyond AI and AR, Cheyer places his bet on Collective Intelligence (CI): new tools and systems to help humans collaborate and tackle global problems (e.g., climate, poverty).
  • “We are going to have to build new tools that … allow us to collectively solve problems better, big and small. I think it's a huge need that's getting ever more present … the next big breakthroughs … will be in CI.” (B, 49:02)
• Cheyer credits government-funded research and cross-pollination for the genesis of both Siri and the internet, urging continued public investment:
  • “All of the work on arpanet and Internet was government funded. Early on it laid all of the foundations … research matters.” (B, 51:23)

12. Advice for Leaders & Builders (54:57–57:13)

• AI is as transformative as the web and mobile—every business must adapt, but should acknowledge today’s barriers (e.g., customer support is still “not quite there”).
• “It is still early in its maturity … you should also know it's still immature and not quite there for some applications.” (B, 55:40)
• Proceed pragmatically, using AI internally with controls; the real “magic” is not universal yet.

Notable Quotes & Memorable Moments

• “The approach is not right. So I'm both amazed and sometimes frustrated.” (B, 02:39)
• “The original 2010 launched Siri had 95% task completion rate success. I don't think any voice assistant since then has that.” (B, 28:52)
• “If it's on the screen, the best way is to directly manipulate it ... If it's off the screen, the best way is to ask for it.” (B, 22:12)
• “The web let us magically now compute using software around the world. But you were still chained at your desk ... Mobile interface now freed you ... Conversational AI lets you now ... do computing if you're driving in your car. ... And so what's missing for AR?” (B, 17:29)
• “Entrepreneurs and magicians are exactly the same. They imagine an impossible future, desirable future … and then … you solve the math and the science to make it come true.” (B, 41:50)

Key Timestamps

• 00:00–03:31: Cheyer’s amazement and frustrations with modern AI compared to Siri
• 03:50–08:28: Three missing pieces: user interface, knowing vs. doing, ecosystem
• 08:51–11:30: Siri’s vision, Apple, and what was lost after Steve Jobs
• 11:30–15:37: The 10+ theory of tech paradigm shifts (GUI → web → mobile → conversational AI → AR)
• 16:27–20:06: The killer OS vs “killer app” philosophy in new paradigms
• 20:06–24:11: Principles of multimodal design; cross-device experiences
• 25:00–30:19: Iterative design, first impressions, and supporting all user expertise levels
• 32:51–36:36: The blend of GUI and language, and future interface predictions
• 37:35–43:55: Magic as presentation, emotional impact, and moving-target definition of AI
• 47:10–50:00: The next “magic moment” and the rise of collective intelligence
• 51:07–54:20: The role of government- and research-funded innovation in creating foundational technologies
• 54:57–57:13: Cheyer’s advice for leaders and product-builders: balance hype, embrace AI, but respect its immaturity

Closing Thoughts

Adam Cheyer offers a nuanced, historically rich perspective on the ongoing digital disruption. He urges leaders to think deeply about interface, architecture, and ecosystem—not just to chase the latest tech hype. The real breakthroughs, he contends, will come from blending human-centric design, collaborative intelligence, and timing—the true ‘magic’ of technology innovation.