OpenAI Takes Out Another Niche

Summary

Tech Brew Ride Home – May 18, 2026

Episode Theme:
This episode dives into OpenAI’s new push into personal finance for ChatGPT Pro users, AI’s growing dominance (and the increasing gap between mega-players and the rest), arXiv’s crackdown on AI-generated "slop", an underwhelming preview of Apple’s forthcoming Siri overhaul, and the often-unspoken vibes of anxiety, malaise, and transformation rippling through Silicon Valley and the wider workforce due to accelerating AI trends.

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1. OpenAI Expands Into Personal Finance (00:53–04:31)

Key Points:

• OpenAI has launched personal finance tools for US ChatGPT Pro users, partnering with Plaid.
• Users can connect accounts from 12,000+ financial institutions (e.g., Schwab, Fidelity, Chase, Robinhood, Amex, Capital One) for analysis of spending, investments, subscriptions, and more.
• This follows OpenAI’s recent acquisition of personal finance startup Hero.
• The tool was enabled by the Hero team’s expertise; it’s unclear if they developed the full feature.
• Access is via the "Finances" sidebar or by typing in a conversation. There is also a data privacy flow—users can remove account connections, and their data is deleted within 30 days of disconnection.
• Upcoming support for Intuit will expand analytics, especially for tax impact and credit applications.
• Over 200 million users reportedly ask financial questions to ChatGPT monthly.
• OpenAI says GPT-5.5 is better at contextual reasoning, with input from finance experts to benchmark and improve its abilities.

Sample User Scenarios:

• "Have I been spending more recently?"
• "Help me build a plan to buy a house in five years."

Quote Highlight:
"OpenAI users can access the tool by selecting Get Started in the Finances option in the sidebar or typing, '@Finances, connect my accounts,' in a ChatGPT conversation. Once users do that, the chatbot will guide them about linking accounts through Plaid." — (02:45)

Notable Details:

• Users have control over linked accounts and can manage or delete financial memory (03:49).
• AI companies, including Anthropic, are making specialized products for sectors like health and finance (04:03).
• The product is exclusive to Pro users initially; wider rollout will depend on feedback.

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2. arXiv Cracks Down on AI-Generated “Slop” (04:40–07:03)

Key Points:

• Academic preprint server arXiv is banning submissions with clear evidence of unchecked AI-generated content.
• If a paper includes “incontrovertible evidence” (like hallucinated references or leftover LLM comments), authors face a one-year ban and future submissions must first be accepted by a reputable peer-reviewed venue.

Notable Quote:
"Our code of conduct states that by signing your name as an author of a paper, each author takes full responsibility for all its contents, irrespective of how the contents were generated." — Thomas Dietrich, arXiv Section Chair (05:22)

• The policy is enforced upon moderator and section chair confirmation, and appeals are allowed (06:15).
• This follows last year’s move to require some computer science review articles to be peer-reviewed before arXiv publication (06:39).

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3. Revenue Gap in the AI Industry Widens (07:03–10:22)

Key Points:

• Anthropic, OpenAI, and a handful of others are pulling far ahead in the generative AI race.
• 34 leading AI startups are generating nearly $80 billion in annualized revenue — up 112% in six months (07:12).
• Much of this revenue is concentrated with the biggest model developers; smaller AI firms depend heavily on OpenAI and Anthropic’s APIs, which puts them in direct competition with their own suppliers.
• Perplexity, ElevenLabs, and Cognition newly joined the half-billion-dollar annualized sales club (08:53).
• There is also “double counting” — startups’ revenues include significant spend on foundational model access.
• Nvidia profits hugely, both powering and investing ($40 billion into OpenAI and Anthropic) (09:32).
• Major public firms (Microsoft, Google, Salesforce, etc.) are also generating billions from AI-powered features, largely built on these same models.

Quote:
"Almost all the AI application companies in our analysis depend in part or almost entirely on models from Anthropic and OpenAI..." (07:44)

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4. Apple’s Siri Overhaul: Still “Beta” After All These Years (12:11–13:05)

Key Points:

• Apple is preparing to release an upgraded Siri with iOS 27, but it's still branded as “beta” internally (12:38).
• The cautious rollout echoes the original Siri’s 2011 launch and suggests low expectations for transformative change.
• The new Siri label may persist even with the public release, after a two-year delay versus rival AI features in Android.

Notable Quote:
“Apple historians may remember… the original Siri [was] branded as a beta… But let’s be honest, Siri has still felt like a beta or even rougher for the better part of 15 years.” — quoting Mark Gurman (12:16)

---

5. The Vibes: AI Anxiety, Cheating, and Silicon Valley Malaise (13:24–18:27)

A. AI in Academia—Cheating Now Normalized

• Stanford senior op-ed highlights how pervasive AI cheating has become – every student uses ChatGPT or Claude now (13:32).
• Early LLM adoption was a geek status symbol; now it’s mundane and almost expected.
• Quote:
  “Half of the laptops in any lecture seem to be open to ChatGPT or Claude. In just a few short years, however, AI has become a fact of life. 'It’s all we talk about,' my ancient Greek art history professor remarked recently.” (14:38 & 14:58)

B. Silicon Valley: Wealth Divide, Job Anxiety, and Existential Malaise

• Viral tweet summarizes the “frenetic” vibes: a few AI insiders have amassed rapid wealth ($20M+), while most tech workers fear permanent underclass status or obsolescence (15:23–16:02).
• Layoffs are common; even tech workers feel their skills are suddenly devalued.
• Quote:
  “The day-to-day role of most jobs has changed overnight with AI… There’s a deep malaise about work and its future. Why even work at all? For peanuts?” (15:54 & 16:19)
• Middle managers feel particularly “paralyzed” and out of step with the new AI world (16:38).
• Even the newly rich lack fulfillment, with “post-economic founders” unsure what to do after sudden wealth (17:01).
• Quote:
  “I once asked a post-economic founder friend why they didn’t just sell the company and they said, ‘and do what? Right now, everybody wants to talk to me and if I sell, I will only have the money.’” (17:24)
• The social and psychological impact: status anxiety, stagnation, and the pressure to “vicode your path to economic enlightenment.” (18:02)

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6. Looking Ahead: Google I/O and Breaking News (18:27–19:08)

• Google I/O is tomorrow; host signals they’ll recap the most important AI news in the next episode, rather than doing a real-time rundown (18:33).
• The Musk v. OpenAI trial verdict just came in and will be covered soon.

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Notable Quotes & Memorable Moments

• “OpenAI and Anthropic have launched health related tools.” (04:03)
• “If a submission contains incontrovertible evidence that the authors did not check the results of LLM generation, this means we can’t trust anything in the paper. The penalty is a one year ban from arXiv...” (05:44)
• “What is often well off anywhere else in the world is being average here.” (17:38)
• “Ironically, a frequent side effect of this torment is to spin up the very products, making everyone rich in hopes that you too can vicode your path to economic enlightenment.” (18:02)

---

Timestamps for Important Segments

• OpenAI Personal Finance Tools: 00:53–04:31
• arXiv AI Slop Ban: 04:40–07:03
• AI Revenue Gap & Industry Dynamics: 07:03–10:22
• Apple Siri Beta Rumors: 12:11–13:05
• AI’s Impact on Education and Work: 13:24–18:27

---

Overall Tone

Informative, concise, and slightly sardonic, with a pulse on both the product and emotional shifts in the tech world. The episode combines fast-paced industry news with deeper reflection on tech culture’s mood swings during a period of rapid AI disruption.

Transcript

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Welcome to the Techbrew Ride Home for Monday, May 18, 2026. I'm Brad McCullough.

[C]

Today, OpenAI debuted personal finance tools via

[B]

Plaid for pro users. The big are getting richer in the

[C]

AI race and pulling away from the

[B]

rest of the industry.

[C]

Archive is cracking down on AI slop,

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Apple's Siri relaunch may still be in beta, and the vibes around AI are getting feverish everywhere.

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dop Late last week, OpenAI debuted personal finance tools for US ChatGPT Pro users,

[C]

partnering with Plaid to give access to more than 12,000 financial institutions to analyze spending and more. Quoting TechCrunch users can connect over 12,000

[B]

financial institutions, including Schwab, Fidelity, Chase, Robinhood, American Express and Capital One. Once users connect these accounts, they will see a dashboard of their portfolio, performance, spending, subscriptions and upcoming payments.

[C]

The new product comes just one month after OpenAI acquired the team behind personal finance startup Hero, which was backed by firms like Ribbit, General Catalyst and restive.

[B]

In April, OpenAI said that the Hero team's expertise and finance was useful in launching this product, but didn't specify if

[C]

the entire feature was built by them.

[B]

OpenAI users can access the tool by

[C]

selecting Get Started in the Finances option

[B]

in the sidebar or typing at Finances,

[C]

Connect my Accounts and a chatgpt conversation

[B]

Once users do that, the chatbot will guide them about linking accounts through Plaid.

[C]

The company said it plans to support Intuit soon, which would enable analysis such as the impact of a stock sale on taxes or the odds of a credit card approval.

[B]

According to OpenAI, more than 200 million users already ask financial questions to ChatGPT every month.

[C]

The company also noted that the new GPT 5.5 model is stronger at reasoning with context, which is crucial for answering finance related questions. The company said it worked with Franklin

[B]

Finance experts to create a benchmark for

[C]

the model to improve on personal finance questions.

[B]

With the new financial tool integration, users can get detailed answers to questions such

[C]

as I feel like I've been spending more recently, has anything changed?

[B]

Or Help me build a plan to

[C]

be ready to buy a house in

[B]

my area in the next five years. Users can go to Settings, then Apps, then Finances to remove connections to certain accounts if they want.

[C]

Once they disconnect a service, the sync data will be removed from ChatGPT in 30 days.

[B]

What's more, users can also view and delete financial memory from the Finances page.

[C]

Generalized chatbots are designed to answer anything

[B]

leading people to ask questions about data

[C]

sensitive topics such as health, finance and personal life. AI companies are realizing this and making specialized products for these sectors. Both OpenAI and Anthropic have launched health related tools.

[B]

Earlier this month, Perplexity launched its own

[C]

financial research product based on its computer agent. OpenAI said its personal finance tools will be available on ChatGPT on the web and on iOS for pro users.

[B]

It noted that based on the feedback from these users, it wants to improve

[C]

the product before making it available to plus users. End quote.

[B]

Archive has had enough of the AI

[C]

slop quoting the Verge arXiv, a popular

[B]

platform for preprint academic research, is taking a new step to attempt to reduce the volume of papers that include AI slop. If a paper has quote incontrovertible evidence that the authors did not check the

[C]

results of LLM generation, such as hallucinated

[B]

references or meta comments Left by an LLM, authors will be banned from arXiv for a year. According to Thomas Dietrich, Archives Section Chair of its Computer Science section, future archive submissions will also have to be accepted at a reputable peer reviewed venue. Here's what he said on X Quote Attention at Archive authors. Our code of conduct states that by

[C]

signing your name as an author of

[B]

a paper, each author takes full responsibility for all its contents, irrespective of how the contents were generated. If generative AI tools generate inappropriate language, plagiarized content, biased content, errors, mistakes, incorrect references, or misleading content, and that output is included in scientific works, it is the responsibility of the authors.

[C]

We have recently clarified our penalties for this.

[B]

If a submission contains incontrovertible evidence that the authors did not check the results of LLM generation, this means we can't trust anything in the paper.

[C]

The Penalty is a one year ban

[B]

from arXiv, followed by the requirement that subsequent ARXIV submissions must first be accepted accepted at a reputable peer reviewed venue.

[C]

Examples of incontrovertible Evidence Hallucinated References Meta Comments from the LLM Here's a 200 word summary. Would you like me to make any changes?

[B]

The data in this table is illustrative.

[C]

Fill it in with the real numbers from your experiments, et cetera.

[B]

Authors can appeal ban decisions, Dietrich told 404 Media. He also noted that this policy will only apply to cases of incontrovertible evidence, and that our internal process requires first a moderator to document the problem and then for the section chair to confirm

[C]

before imposing the pen penalty.

[B]

Last year, Arxiv also updated its policies to reduce AI slop by only allowing computer science review articles and position papers to be published if they have been

[C]

peer reviewed and have been accepted at a conference or a journal. The advent of large language models have

[B]

made this type of content relatively easy to churn out on demand, and the majority of the review articles we receive are little more than annotated bibliographies with

[C]

no substantial discussion of open research issues, arxiv said at the time. End quote Foreign.

[B]

Suggests that there is a widening revenue gap between Anthropic OpenAI and the rest

[C]

of the entire AI industry. Quoting the Information A group of 34

[B]

leading startups in the AI sector, including Anthropic and OpenAI, is generating nearly $80 billion in annualized revenue, or 6.6 billion

[C]

per month, from selling AI applications or access to the models that power such apps, according to the Information's generative AI database. That's up 112% from just six months ago.

[B]

Investors at firms like Sequoia Capital have made the bet that the vast majority of software value in the current AI era will be generated by the top developers of advanced AI models rather than by developers of pure AI apps.

[C]

That's because almost all the AI application

[B]

companies in our analysis depend in part or almost entirely on models From Anthropic and OpenAI, the smaller startups reliance on Anthropic and OpenAI could be a problem

[C]

because those two leaders have been developing new kinds of models or versions of their products targeting specific industries or white collar work roles. See the earlier segment putting themselves in

[B]

direct competition with their startup customers.

[C]

That could eventually make it harder for those startups to keep up their growth.

[B]

That dynamic could help explain the frenetic funding environment for so called AI NEO labs that are seeking to leapfrog anthropic and OpenAI by developing new kinds of AI models. The $80 billion annualized sales figure is remarkable as few of the companies existed or generated revenue before 2023. Anthropic can claim about half amount as

[C]

its Revenue recently surpassed OpenAI's on the strength of its AI for coding tasks and other white collar work.

[B]

The 32 AI model or application startups not named Anthropic or OpenAI may not

[C]

be growing as fast as the leaders,

[B]

but they aren't far behind in that

[C]

regard and continue to hit new revenue milestones largely through sales of subscriptions and some usage based Feees.

[B]

Since December, three of those companies crossed

[C]

$500 million in annualized sales, joining coding

[B]

app Cursor in that club, according to our analysis. The three newbies are search firm Perplexity, voice AI provider ElevenLabs and coding app Cognition.

[C]

Our analysis doesn't include the infrastructure startups that rent out Nvidia AI servers.

[B]

Now there is some double counting going on.

[C]

The four aforementioned startups that are generating more than $500 million in annualized sales, as well as the other companies on

[B]

the list likely collectively pay OpenAI and anthropic billions of dollars a year for

[C]

models to power their products. Almost all of the company's products are powered by Nvidia servers, helping the chip designer generate the vast majority of profits so far in the AI boom, Nvidia has partly returned the favor, investing capital

[B]

in at least 13 of the 34 companies on our list, including about $40 billion in OpenAI and anthropic combined.

[C]

The capital helps the companies keep renting Nvidia servers.

[B]

Our analysis doesn't cover public companies that are also generating revenue from AI applications and selling models they develop themselves. Microsoft, for instance, has generated at least $6 billion in actual revenue from selling Copilot branded apps, power in part by

[C]

OpenAI models that it uses for free.

[B]

Google sells a lot of Gemini AI

[C]

models and Gemini powered features in enterprise apps, and AI Answers appear to be boosting its core search engine and by extension, the search advertising business.

[B]

A dozen major enterprise software firms such

[C]

as Salesforce and ServiceNow are collectively on pace to generate billions of dollars a

[B]

year selling AI powered features and agents in their products. There are also major customers of Anthropic and OpenAI, both for internal use and

[C]

to power their products. They sell these AI buyers have been enduring recent price hikes from Anthropic End quote.

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to underwhelm once again. Quoting Mark Gurman, what's old is new again.

[B]

Apple historians may remember that when the company rolled out the original Siri back in 2011, it did so by branding the voice assistant as a beta, a

[C]

label meant to denote that it's not a fully baked product and may include some issues. The company ended up dropping that nomenclature in 2013 as part of iOS7. But let's be honest, Siri has still

[B]

felt like a beta or even rougher

[C]

for the better part of 15 years.

[B]

Anyways, back to the point. Test versions of iOS 27 within Apple use this label for the new Siri and include a toggle to leave the the Siri beta.

[C]

Given that we're only a month out

[B]

from wwdc, there is a strong chance

[C]

that this approach will be used in developer beta versions and even when iOS27 ships this fall.

[B]

This all means that even after a two year delay, the revamped Siri was

[C]

supposed to arrive in 2024, the company

[B]

could still brand the new features as unfinished.

[C]

It's a far cry from what we're seeing in the Android universe. End quote. Which yeah, Google I O's keynote is tomorrow and expect a metric ton of AI announces there.

[B]

Let's end with a couple of vibey

[C]

stories around the Vibes of AI at the moment. In a Times Opinion piece, a college

[B]

senior at Stanford describes how AI has changed classwork and college generally.

[C]

Cheating using AI has, according to them,

[B]

become omnipresent, with students fudging just about everything. Students were probably the earliest wide scale adopters of AI.

[C]

After all, it was far and away the quickest route to an A. When I took CS107, the only viable

[B]

way for people to cheat was to

[C]

seek out a student who'd gone through

[B]

the class before and beg for solutions

[C]

to the notoriously difficult problem sets.

[B]

There was no alternative to putting in a large amount of work, even if one did obtain the answers from another student.

[C]

Engaging, by the way, in a social act if nothing else.

[B]

The students I knew who did this

[C]

still spent hours sculpting their stolen code so as not to be caught.

[B]

Few cheated in this most overt fashion back then, but a month later, any student could instead turn to a chatbot,

[C]

plugging in a prompt, alone in a dorm room, and mindlessly regurgitating the result.

[B]

I remember the first time I used

[C]

it, feeling an immediate sense of guilt. A friend recently told me. Now it's just normal.

[B]

Half of the laptops in any lecture

[C]

seem to be open to ChatGPT or Claude. In the beginning, experimenting with models was a pastime for the nerds showing off the the early access you got to the next frontier. Large language model was a status symbol,

[B]

and people would come pleading for your

[C]

authorization keys to try it out for themselves.

[B]

In just a few short years, however, AI has become a fact of life.

[C]

It's all we talk about, my ancient Greek art history professor remarked recently. End quote.

[B]

And

[C]

on X had a tweet that

[B]

got people either schadenfreuding or popcorn eating

[C]

or mocking or all three over the weekend. I'm just going to read it.

[B]

Quote the Vibes in San Francisco feel pretty frenetic right now. The divide in outcomes is the worst I've ever seen. Over the last five years a group

[C]

of around 10,000 people employees at Anthropic OpenAI XAI Nvidia Meta TBD founders have hit retirement wealth of well above $20 million back of the envelope AI estimation.

[B]

Everyone outside that group feels like they

[C]

can work their well paying jobs but sub 500,000 dol a year for their

[B]

whole life and never get there. Worse yet, layoffs are in full swing.

[C]

Many software engineers feel like their life skill is no longer useful. The day to day role of most jobs has changed overnight with AI as a result.

[B]

Number one, the corporate ladder looks like the wrong building to climb.

[C]

Everyone's trying to align with a new set of career paths. Should I be a founder? Is it too late to join Anthropic or OpenAI? Should I get into AI?

[B]

What company stock will 10x next?

[C]

People are demanding higher salaries and switching jobs more and more.

[B]

Number two, there's a deep malaise about

[C]

work and its future. Why even work at all?

[B]

For peanuts?

[C]

Will my job even exist in a few years? Many feel helpless. You hear the permanent underclass conversation a lot, especially from young people. It's hard to focus on doing good work when you think man, if I joined Anthropic two years ago I could retire.

[B]

Number three, the mid to late middle managers feel paralyzed.

[C]

Many have families and don't feel like they have the energy or network to just start a company. They don't particularly have any AI skills. They see the writing on the wall. Middle management is being hollowed out in many.

[B]

Number four, the rich aren't particularly happy either. No one is shedding tears for them and rightfully so. But those who have quote made it

[C]

experience a profound lack of purpose as well.

[B]

Some have gone from less than $150,000

[C]

to greater than $50 million in a few years with no ramp.

[B]

It flips your life plans upside down.

[C]

For some, comparison is the thief of joy. For some they escape to New York City to just live life. For others they start companies just cause often to win status points.

[B]

They never imagined that by age 30

[C]

they I once asked a post economic founder friend why they didn't just sell the company and they said and do what?

[B]

Right now everybody wants to talk to

[C]

me and if I sell I will only have the money.

[B]

I understand that many reading this scoff

[C]

at the champagne problems of the valley. Society is warped in this tech bubble. What is often well off anywhere else in the world is being average here

[B]

Unlike many other places, tenure, intelligence and hard work can be loosely correlated with

[C]

outcomes in the Bay. Living through a societally transformative gold rush in that environment can be paralyzing.

[B]

Am I in the right place?

[C]

Should I move?

[B]

Is there still time left?

[C]

Am I going to make it? It psychologically torments many who have moved here in search of success. Ironically, a frequent side effect of this torment is to spin up the very products, making everyone rich in hopes that you too can vicode your path to economic enlightenment. End quot.

[B]

So tomorrow is Google I o.

[C]

But as I mentioned earlier in the

[B]

show, there will be so much announced

[C]

and it will get started only at

[B]

1pm Eastern that I think the only sensible thing to do is delay talking

[C]

about IO until Wednesday's show.

[B]

That way things can settle out and

[C]

we'll have a better sense of what was important and what wasn't. As opposed to me just rattling off everything announced in chronological order without having the visibility to emphasize the importance of

[B]

stuff over the unimportant.

[C]

And also, as I'm putting the final touches on this episode, the jury just came in on the Musk v. OpenAI trial, so we need to make room for that. Talk to you tomorrow.

[D]

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