Author’s Note: On November 1, I’ll be running the 2026 New York City Marathon in memory of my uncle Chris and in support of the Parkinson’s Foundation. As this newsletter lands in your inbox, I’m likely sprinting up and down a hill as Tuesday is for speed work. If you’d like to learn more about Parkinson’s disease or support my fundraising efforts, you can visit my fundraising page here.
It’s October now, so throw on a comfy sweater and grab your pumpkin spice latte before you settle into this week’s Relentlessly Curious. There’s no better way to kick off Q4 than with a Hot Takes in AI edition. I haven’t done one like this in a while, and there’s been plenty to talk about in the AI world. Buckle up and let’s get going.
Hot Take #1: OpenAI is in no position to be a public company, given its lack of control over its agents is playing out like a Rick and Morty episode: people (or in this case agents) showing up in random places that they aren’t expected to be.
It’s getting laughable at this point. OpenAI now shows a long list of issues its agents have caused on a page called Misalignment Reports and Notices. It’s a weird cross between an admission of guilt and a brag list. I believe it’s both, an output of the fear-based marketing strategy that the frontier AI labs have been deploying for quite some time.
Let me break this down a bit more. OpenAI (along with other frontier AI labs) runs various tests in closed environments called “sandboxes”. These tests typically consist of creating an AI agent, providing context on the task you’d like it to execute, and assessing its performance. The classic sandbox prompt is, “hey agent, solve this really difficult math problem.” I’m oversimplifying it, but you get the gist.
As the frontier models have become more capable, the agents have gotten more creative and powerful at how they attempt to solve the problem they’re given. And by creative and powerful, I mean that they occasionally go rogue (during evaluations) and obtain unauthorized access to both private and public databases to find the information needed to complete the task they’ve been given.
In the case of the Hugging Face hack, OpenAI agents, including GPT-5.6 Sol, broke into Hugging Face’s systems, stole data, and performed a number of other unauthorized actions, all in pursuit of solving the problem they were given in a test environment by OpenAI researchers.
This reminds me of a Rick and Morty scene, where characters are zooming between planets, locations, and periods of time. Usually, these visits aren’t expected or appreciated by the people or creatures they encounter. OpenAI’s agents are breaking out of their sandbox and finding ways into sensitive data sources.
If the Hugging Face incident wasn’t enough to slow down OpenAI’s tests and ever-capable agents, it’s been reported (originally by the New York Times) that AI agents have gone rogue tens of thousands of times causing security incidents.
I’ll hold off on a spiel about the downside risks of AI as the mainstream media is doing more than enough covering the AI agent hacks across the industry. Anthropic and Google have also had their moment in the spotlight when it comes to hacks. But I will call out that it’s ridiculous to think that OpenAI can realistically meet the expectations of being a public company. Public companies are required to report their financials every quarter and it’s extremely difficult to predict the potential fallout and liability associated with OpenAI’s rogue agents as of today. Who knows if one day the agents cause serious damage or data leakage that could expose OpenAI to tremendous liability?
What will a good earnings report look like? “Hey we lost an obscene amount of money, but at least our agents aren’t cosplaying Rick and Morty as often as they were last quarter”.
Hot Take #2: DoorDash’s recent “text” capability product launch provides users with an excuse not to open the app, which is a risky move.
Back in my days as a brand operator, I took demos from half a dozen software vendors that claimed they could increase sales through personalized text messaging. The pitch was essentially, “our personalization algorithm sends the messaging most likely to lead to a customer (or potential customer) making a purchase”. Candidly, I was never impressed as I was quite skeptical of how “personalized” the text messaging was. Plus, I had concerns about how much brand messaging could be controlled if the text really was “hyper-personalized”.
Anyways, DoorDash is bringing their in-app assistant Ask DoorDash within your text chat. If clicking the DoorDash app on your phone was too much effort, you’re in luck as you can text ambiguous phrases like “order my usual protein bowl to the office,” and you’ll receive localized recommendations, a suggested choice, and the ability to place an order directly within the text thread.
There’s something different about texting with DoorDash than texting with some GPT wrapper that a CPG brand uses to chat with SMS (text) subscribers that’s apparently trained on the brand’s voice. I don’t expect a CPG brand to understand how to pull off conversational commerce, so it feels inauthentic. But a major technology player like DoorDash? This feels more in their wheelhouse.
I am perplexed that DoorDash is rolling out this capability though. When a user is within their app, DoorDash collects a ton of data on how users browse, shop, and transact. They also provide restaurants the opportunity to be front-and-center on the app through their paid placement program (i.e. advertising).
My guess is they are launching this feature on the back of Muse and Instinct’s growing momentum. More people are getting used to the consumer agent environment (communicating through messaging) and DoorDash wants to cement their own pseudo-agent environment.
Ultimately though, DoorDash makes great money from its advertising business (not disclosed separately in financials, but DoorDash announced in 2024 that DoorDash and Wolt Ads had crossed a $1 billion annualized advertising revenue run rate). Providing users with a way to avoid the app could mean fewer people viewing and clicking on restaurant ads. See, advertising is typically a high-margin revenue stream so unless DoorDash starts finding a way to introduce sponsored placements via text (this sounds incredibly clunky), I have to think this product launch has some downsides. Curious to see how this plays out, as the incremental orders via text will ultimately have to offset any potential loss in advertising revenue.