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The biggest unresolved question in AI right now, and more takeaways from Madrona’s IA40 Summit

2 October 2026 at 15:17
Madrona Managing Director Matt McIlwain speaks at the IA40 Summit in Seattle on Wednesday. (GeekWire Photo / Todd Bishop)

Executives from companies such as Microsoft, Amazon, Anthropic and Stripe agreed on a lot this week about where AI is headed. But one big question was left unresolved: who keeps the relationship with the customer, and the data that comes from it, once an AI agent is in the middle?

That question was a recurring theme at Madrona’s IA40 Summit, the venture capital firm’s annual gathering of AI startups, investors and tech executives, held Wednesday at the Four Seasons Hotel on the downtown Seattle waterfront.

As Madrona Managing Director Matt McIlwain said in his closing remarks, the question of who gets to use the data that comes from people’s engagement with AI systems came up “over and over and over again” during the day.

GeekWire attended the entire day and came up with these takeaways, reducing our own human bottleneck (see below) with lots of back-and-forth with Anthropic’s Claude and other AI tools.

AI agents are coming between companies and their customers: Charles Lamanna, the Microsoft executive vice president who oversees Microsoft 365 and the platform behind Copilot, predicted most business software will end up being used by AI assistants on a person’s behalf, leaving software makers with less power to set prices.

Jean-Denis Greze, CEO of Town, a startup that makes an AI assistant for work, went further. Since about July, he said, AI has been able to operate a browser or a computer almost as well as a person, at a reasonable cost. That means an AI assistant can work through an app’s user interface the way a person does, without needing an API from the software maker, he said.

“Everything is going to become a thin app because the better the AI gets at using the computer, the less the app matters as a unit of software,” Greze said, echoing the term Lamanna had used that morning for software that people open only briefly.

The same shift is under way in retail. Maia Josebachvili, Stripe’s chief revenue officer for AI, said commerce by AI agents on Stripe was roughly flat for eight or nine months and then rose sharply in the past six weeks.

Many merchants make their money by getting shoppers to add to their orders at checkout and by showing them ads, she said, and they lose those chances when an agent does the buying. That won’t work over the long term, Josebachvili said.

That conflict is playing out in real time in a high-profile dispute between two tech giants. Amazon blocked Meta’s Muse assistant from shopping on its site last month.

Anthropic Chief Technology Officer Rahul Patil at Madrona’s IA40 Summit. (GeekWire Photo / Todd Bishop)

The data side of the question came up in a session with Anthropic Chief Technology Officer Rahul Patil. Moderator Raphaëlle d’Ornano asked who owns the record of an AI agent’s work, including its mistakes and corrections, and whether it belongs to the customer. She said she has never gotten a clear answer.

Patil didn’t answer directly. He said each company that supplies the software for running agents will work to improve them, and “will use every data that’s available to them to make it better.”

“It’s good for the ecosystem if the agents actually improve,” he said.

Swami Sivasubramanian, Amazon Web Services’ vice president of Agentic AI and Emerging Technologies, said one of the least appreciated parts of making AI agents work is getting them the right company data for the task.

AWS in June announced a service for that purpose, called AWS Context, which maps the relationships in a company’s data for agents to use. Sivasubramanian said it’s meant to work across platforms and cloud providers, and he expects this kind of service to be a basic building block for the next 20 years, as cloud storage and databases were two decades ago.

Swami Sivasubramanian, left, Amazon Web Services’ vice president of Agentic AI and Emerging Technologies, with Madrona Managing Director Tim Porter. (GeekWire Photo / Todd Bishop)

Most companies aren’t keeping up with the technology: Patil said Anthropic writes about 200 times as much code as it did 18 months ago. Some customers have doubled or tripled their output, he said, but almost none have seen gains like Anthropic’s.

“The bottleneck is actually not AI. The bottleneck is human,” said Archana Vemulapalli, global head of AI product management at Goldman Sachs. A company’s roles and processes were built before AI, she said.

Archana Vemulapalli, global head of AI product management at Goldman Sachs, speaks at Madrona’s IA40 Summit in Seattle on Wednesday. (GeekWire Photo / Todd Bishop)

Sivasubramanian said teams inside Amazon were showing him impressive AI agents they had built in two or three weeks. When he asked when the agents could be rolled out, he said, almost every team told him it still had to work out security, identity and monitoring.

McKinsey senior partner Lari Hamalainen said about 40% of companies say AI has increased their profits, but only 6% describe the increase as substantial.

Even as AI becomes more and more capable, there’s still lots of work to do to close the gap between “the goals, the capabilities, and what we all are aspiring to do,” McIlwain said.

Companies are split on depending on a single AI provider: Anthropic’s Patil, notably, argued that large companies are spending too much effort preserving the ability to switch between AI providers. To keep that option open, he said, they end up building for the least common denominator, limiting themselves to the features every AI model shares. That effort also takes their engineers away from the work that sets their own company apart.

Carlos Guestrin, co-CEO of the AI startup Noeri, offered an alternative take on the same panel. Intelligence shouldn’t be controlled by one or two companies that own the models, he said, and every company should be able to build and own its own AI systems.

Carlos Guestrin, co-CEO of Noeri and a Stanford computer science professor, at Madrona’s IA40 Summit. (GeekWire Photo / Todd Bishop)

Guestrin is a Stanford computer science professor and former University of Washington professor who founded the Seattle machine learning startup Turi, which Apple acquired in 2016.

Eno Reyes, co-founder and chief technology officer of Factory, a startup that makes AI coding tools, said on a later panel that many businesses don’t see a way to build their future without ceding control to one AI lab. Thomas Dohmke, the former GitHub CEO who now leads the startup Entire, said developers always want choice.

Amazon works with more than one AI lab. It is a major Anthropic investor and partner, and Dan Grossman, Amazon’s vice president of business and corporate development, pointed out on an investor panel that Amazon had launched a managed agents product with OpenAI that week.

Amazon also sells its own product for running AI agents, AgentCore, which overlaps with Anthropic’s Managed Agents.

Companies don’t yet trust AI with important decisions: Zico Kolter, the Carnegie Mellon professor who chairs the safety and security committee of OpenAI’s board, said the ability to control AI systems has to keep pace with their capabilities, which might mean developing them more slowly than is possible.

Sivasubramanian said executives worry about whether an AI agent will always follow their company’s rules and regulations. Companies can keep the creativity of AI models, he said, by pairing them with separate systems that check a model’s work against the company’s rules and catch violations.

The money is concentrated in a few companies: The companies on this year’s IA40 list have raised $410 billion since they were founded, according to Madrona’s data. OpenAI, Anthropic and Databricks account for 92% of it.

Anthropic raised $143 billion of its $161 billion total in the 12 months ending Aug. 15, a figure that includes debt. The company has filed confidentially for an initial public offering and is seeking a valuation of about $2 trillion, Reuters reported this week. Bloomberg reported that it could go public as early as mid-November.

Capital spending by Amazon, Alphabet, Microsoft, Meta and Apple is projected to rise 74% this year to about $742 billion, according to PitchBook figures Madrona presented.

Lamanna said Microsoft’s heaviest AI users among its software developers are each on track to spend more than $1 million a year on AI usage, even with the company’s internal discount.

Madrona’s closing slide said returns on AI are still early for most of the companies using it but look inevitable based on what the earliest adopters are seeing.

‘Agents are very harsh customers’: Microsoft exec warns many apps will lose pricing leverage

30 September 2026 at 13:48
Microsoft’s Charles Lamanna, executive vice president of Copilot, Agents and Platform, left, speaks with Madrona Managing Director Matt McIlwain at Madrona’s IA40 Summit in Seattle on Wednesday. (GeekWire Photo / Todd Bishop)

Charles Lamanna, the Microsoft executive who oversees Microsoft 365 and the platform behind Copilot, says most business software will end up running behind AI agents rather than in front of users. That’s bad news for a lot of apps.

“If my agent interacts with your app exclusively, the agent’s your customer, not the end user,” Lamanna said Wednesday morning, speaking with Madrona’s Matt McIlwain in the opening keynote at the venture capital firm’s annual IA40 Summit in Seattle. “And agents are very harsh customers.”

Agents will pick whatever service is cheapest, fastest and most reliable, he said, and they’ll move people to another one quickly. Apps that sit behind agents will have a hard time holding on to pricing power or customer loyalty.

Lamanna splits software into two groups.

  • “Thick” apps are where people spend most of their workweek, such as CAD programs, contact-center software, or Excel for a full-time financial modeler.
  • “Thin” apps are the ones people drop into and leave. He said that describes the vast majority of business software, and those apps will end up running “headless,” with AI assistants such as Copilot and ChatGPT doing the work through the back end.

Microsoft’s own apps aren’t exempt. Word, Excel and PowerPoint won’t go away, Lamanna said, but most people will use them inside Copilot, which can now run Office without switching apps. In his view, the standard setup for an office worker ends up as Copilot for AI and Teams for communication, “and that’s maybe it.”

He compared a headless app to a company that sells only on Amazon. It can be a business, he said, but prices get squeezed when buyers are simply choosing between “your pencils or those pencils.” A brand such as Nike has more leverage.

Amazon itself is resisting that role. Earlier this week it blocked Meta’s Muse agent from shopping on its site, saying Meta never asked permission and that the agent doesn’t identify itself and appears to store customer credentials. Meta has said Muse can’t see users’ passwords or payment methods. Amazon is also in a legal fight with Perplexity over that company’s Comet shopping agent.

Amazon is open to agents on its own terms. Days after blocking Muse, it opened its seller tools to Anthropic’s Claude, letting merchants manage inventory, prices and listings without going into Seller Central.

Lamanna brought up Muse himself onstage, predicting it will reach far more people than work-focused agent tools such as Copilot and Claude Cowork.

Microsoft is on the other side of the same question. Copilot depends on other companies’ software being willing to work behind it. In an August profile, Lamanna said Copilot uses connectors to pull data from services such as Salesforce and ServiceNow, so people don’t have to leave the app.

Live show: Amazon, Meta and the fight over the future of AI; Plus, is Seattle still the place to build?

26 September 2026 at 11:13
GeekWire co-founders Todd Bishop, left, and John Cook open the GeekWire Podcast and VIP dinner, presented by Northern Trust, at Daniel’s Broiler in downtown Seattle. (Photo by Tanya Srisuthisuriya)

This week: Amazon is blocking Meta’s new Muse AI assistant from shopping on Amazon.com, saying the agent doesn’t identify itself and violates the site’s conditions of use. We explain why the standoff is an early sign of a much bigger fight over whether AI agents can use websites and apps on people’s behalf, and why Amazon has so much riding on the answer.

For the definitive word on the issue, we ask Muse what it has to say for itself, and get an impressively sophisticated and evenhanded response. 

We recorded this week’s show live at Daniel’s Broiler in downtown Seattle, in front of a room of startup founders and CEOs, at a dinner hosted and sponsored by Northern Trust.

Mike Fridgen, a longtime Seattle entrepreneur and Madrona venture partner now working on a stealth startup, joins us to talk about whether Seattle is still a good place to build a company. The conversation covers the region’s talent, its history and the debate over taxes including Seattle’s JumpStart payroll tax, which Mayor Katie Wilson’s new budget holds flat.

Then we take questions from the room. Ridge AI CEO Ellie Fields asks how business leaders can engage productively in building the region, Latch CEO Stefan Kalb asks why Seattle has less venture capital than the Bay Area and ACME Brains founder Mary Jesse asks how to get past polarization.

Todd Bishop, left, and John Cook talk with Mike Fridgen during the live recording of the GeekWire Podcast at Daniel’s Broiler in downtown Seattle. (Photo by Tanya Srisuthisuriya)

We close with a satellite-themed GeekWire Trivia Challenge and an unexpected announcement from Starfish Space co-founder Austin Link.

Related links

With GeekWire co-founders John Cook and Todd Bishop. Music by Daniel L.K. Caldwell. 

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