Happy Tuesday. For those keeping track at home, my rotator cuff appears to still be intact about a week after barely being able to move it. I appreciated all the kind messages many of you sent me, even if I wish I could blame the pain on some fantastic feat of adventure or athleticism rather than a mystery injury exacerbated by sleeping funny in a hotel bed. But I’m mostly painless now, so I’ll count that as a win. Thanks again.
Before we get into this week’s interview, a quick note on two launches happening today that I’m paying attention to.
First, the healthcare startup General Medicine, from the founders of the online pharmacy PillPack, is launching a conversational AI experience that allows customers to “ask questions, note concerns, share observations,” and then be connected to the appropriate doctor for either a virtual or in-person appointment. The tool creates summaries for doctors to give them the right context before the appointment, alongside whatever other health history the patient has shared with the service.
You can try out the new AI feature here and read more about the startup in an exclusive piece I wrote at Fortune earlier this year.
I also plan to keep tabs on a new travel startup launching today called TripTap. Using AI apps to research travel options and create itineraries has become a popular use case (as perfectly highlighted by The Aisle subscriber Steve Frazier’s experience recounted in this newsletter a couple of weeks back). TripTap is trying to take such ideas a step forward by marrying trip inspiration and discovery via a conversational interface with the ability to actually book hotels, restaurants, and experiences. TripTap CEO Michael DiLorenzo was one of the first employees at Drizly, the liquor delivery company that Uber acquired in 2021.
Shoot me a note and let me know what you think if you try out one of the above services. And if you’re launching something new soon, give me a heads up and I’ll consider a mention in a future newsletter.
Now on to the good stuff…
Profound co-founders James Cadwallader (left) and Dylan Babbs (right). Courtesy of Profound
The Center Aisle
As I started paying closer attention to the agentic commerce space over the past year, I was struck by the rush to remake SEO for the AI age. Whether you prefer the term Answer Engine Optimization (AEO), Generative Engine Optimization (GEO), or Artificial Intelligence Optimization (AIO), this marketing discipline has exploded in 2025, with companies of all sizes and backgrounds sensing a gold rush opportunity.
As companies jockey to convince brands that their tools can help marketers reliably show up in AI-generated answers, hype has ballooned—and investors have taken notice.
For those reasons and others, I plan to report deeply on the space in the coming months. If you have ideas or tips—juicy or otherwise—reply and let me know.
With that in mind, I wanted to talk to one of the entrepreneurs behind New York City-based Profound, one of the startups sucking up a lot of oxygen in this space. The startup, which launched in 2024, has raised more than $50 million from blue-chip venture capital firms including Sequoia Capital. The company lists Walmart, Wayfair, Figma, Brex, and LG among its clients.
I caught up recently with Profound co-founder and CEO James Cadwallader to ask him about differentiation in an increasingly crowded space, the fear that we’ll be overwhelmed by AI-generated marketing slop, and more.
The conversation has been edited for length and clarity.
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