The writer and comedian Megan Koester got her first writing job, reviewing internet pornography, from a Craigslist ad she responded to more than 15 years ago. Several years after that, she used the listings website to find the rent-controlled apartment where she still lives today. When she wanted to buy property, she scrolled through Craigslist and found a parcel of land in the Mojave Desert. She built a dwelling on it (never mind that she’d later discover it was unpermitted) and furnished it entirely with finds from Craigslist’s free section, right down to the laminate flooring, which had previously been used by a production company.
“There’s so many elements of my life that are suffused with Craigslist,” says Koester, 42, whose Instagram account is dedicated, at least in part, to cataloging screenshots of what she has dubbed “harrowing images” from the site’s free section; on the day we speak, she’s wearing a cashmere sweater that cost her nothing, besides the faith it took to respond to an ad with no pictures. “I’m ride or die.”
Koester is one of untold numbers of Craigslist aficionados, many of them in their thirties and forties, who not only still use the old-school classifieds site but also consider it an essential, if anachronistic, part of their everyday lives. It’s a place where anonymity is still possible, where money doesn’t have to be exchanged, and where strangers can make meaningful connections—for romantic pursuits, straightforward transactions, and even to cast unusual creative projects, including experimental TV shows like The Rehearsal on HBO and Amazon Freevee’s Jury Duty. Unlike flashier online marketplaces such as DePop and its parent company, Etsy, or Facebook Marketplace, Craigslist doesn’t use algorithms to track users’ moves and predict what they want to see next. It doesn’t offer public profiles, rating systems, or “likes” and “shares” to dole out like social currency; as a result, Craigslist effectively disincentivizes clout-chasing and virality-seeking—behaviors that are often rewarded on platforms like TikTok, Instagram, and X. It’s a utopian vision of a much earlier, far more earnest internet.
“The real freaks come out on Craigslist,” says Koester. “There’s a purity to it.” Even still, the site is a little tamer than it used to be: Craigslist shut down its “casual encounters” ads and took its personals section offline in 2018, after Congress passed legislation that would’ve put the company on the hook for listings from potential sex traffickers. The “missed connections” section, however, remains active.
The site is what Jessa Lingel, an associate professor of communication at the University of Pennsylvania, has called the “ungentrified” internet. If that’s the case, then online gentrification has only accelerated in recent years, thanks in part to the proliferation of AI. Even Wikipedia and Reddit, visually basic sites created in the early aughts and with an emphasis similar to Craigslist’s on fostering communities, have both incorporated their own versions of AI tools.
Some might argue that Craigslist, by contrast, is outdated; an article published in this magazine more than 15 years ago called it “underdeveloped” and “unpredictable.” But to the site’s most devoted adherents, that’s precisely its appeal.
“ I think Craigslist is having a revival,” says Kat Toledo, an actor and comedian who regularly uses the site to hire cohosts for her LA-based stand-up show, Besitos. “When something is structured so simply and really does serve the community, and it doesn’t ask for much? That’s what survives.”
Toledo started using Craigslist in the 2000s and never stopped. Over the years, she has turned to the site to find romance, housing, and even her current job as an assistant to a forensic psychologist. She’s worked there full-time for nearly two years, defying Craigslist’s reputation as a supplier of potentially sketchy one-off gigs. The stigma of the website, sometimes synonymous with scammers and, in more than one instance, murderers, can be hard to shake. “If I’m not doing a good job,” Toledo says she jokes to her employer, “just remember you found me on Craigslist.”
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![OpenAI’s existential questions | TechCrunch
OpenAI has been all over the news recently, whether that news is about acquisitions, competition with Anthropic, or bigger debates about AI’s impact on society.
On the latest episode of TechCrunch’s Equity podcast, Kirsten Korosec, Sean O’Kane, and I did our best to round up all the latest OpenAI news. While the company’s latest acquisitions seem to be classic acqui-hires, Sean suggested they also address “two big existential problems that OpenAI is trying to solve right now.”
First, with the team behind personal finance startup Hiro, the company may be hoping to come up with a product that has “more hooks than just a chatbot, and maybe something worth paying more for.” And with new media startup TBPN, OpenAI could be looking to “better shape its image in the public eye, which lately has not been great.”
Read a preview of our conversation, edited for length and clarity below.
Anthony: [We have] two deals that are worth mentioning, one is that OpenAI acquired this personal finance startup called Hiro. And that comes after another deal that was literally announced when we were recording our last episode of Equity, so we didn’t get to talk about it: OpenAI had also acquired TBPN — a business talk show, like a new media company.
And I think both of these deals are pretty small compared to the scale of OpenAI. These are not things that people expect to really change the course of their business or anything like that, but they’re interesting because it suggests that there’s still this [attitude of,] “Let’s try out different things.”
Especially [with] the TBPN deal […] particularly at this time when it feels like OpenAI, from all the reporting we’re reading, is also trying to really refocus on making ChatGPT and its GPT models really competitive in an enterprise context with programmers.
Techcrunch event
San Francisco, CA
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October 13-15, 2026
Is running a tech talk show, should that really be on the to-do list?
Kirsten: No, this should not be on the to-do list. That’s it.
I do want to mention Hiro because to me, that’s an interesting one, because Julie Bort, our venture editor, super talented, she wrote about this and was I think the first to write about it. She dug in a little bit and basically this looks like an acqui-hire. The company is folding. They basically said, “By this date, you won’t be able to access this anymore.”
This is a personal finance startup. And they only launched two years ago. So this absolutely is about getting talent on board. So I’m very curious to see if OpenAI is going to be just absorbing them into the ether at OpenAI, or if they’re actually interested in some sort of personal finance product that they want to work on. To me, it’s not really clear.
Sean: I think you look at both of these as acqui-hires to a certain extent. I mean, the TBPN acquisition, allegedly they are going to retain their editorial independence on the show that they make every day. And all respect to those guys who’ve put that out there and gotten it off the ground so quickly and grown it into what it has become.
I think any person who follows the media should have a healthy dose of skepticism that when you acquire something like that and you put the people who make the show under the org of the public policy people and comms or marketing adjacent people higher up at the company making the acquisition, that you could have good questions about whether or not saying “editorial independence” is enough. It’s not an incantation that just works.
But you know, what’s interesting to me about these two, while they are similar in their acqui-hire-ness, I think they both represent two major problems that OpenAI is facing.
One is Hiro. OpenAI has a very successful product in ChatGPT. As far as whether or not that will actually ever make them enough money to become a sustainable business that’s not raising the largest private rounds in the world, ever, to keep things going, is a big question. And they also seem to be struggling to keep up on the enterprise side of things where the real money seems to be, so bringing in a team like this seems like taking a shot at, “What else can we do?”
The guy who founded Hiro seems to have a serial entrepreneur streak of creating consumer apps, and so this seems to me like a bet on them being able to come up with something else that may have more hooks than just a chatbot, and maybe something worth paying more for.
And then TBPN is an acquisition made to help better represent what the company does and better shape its image in the public eye, which lately has not been great and certainly is under more questions now than just a few weeks ago, because Ronan Farrow just led a report at The New Yorker that dropped suspiciously right around the time that this and a couple other announcements from OpenAI came out last week.
I think those are two big existential problems that OpenAI is trying to solve right now.
Kirsten: So the thing that you didn’t say is, there’s Anthropic kind of looming in — not in the shadows, I mean, they’re very much taking up a lot of space here — but they’re having a lot of success on the enterprise side of things.
It feels like these guys are competitors and they also feel like very different companies in a lot of ways. Anthony, I’m wondering if you see them as direct competition to OpenAI? Or [are they] just finding their stride in enterprise and in a way, these two companies are clearly going to coexist and they’re really not directly competing with each other — maybe on talent, but not necessarily as we initially thought of them?
Anthony: I think they’re directly competing with each other. There’s definitely a scenario where if AI as an industry, as a technology, is as successful as its proponents hope for, they could both be very successful companies, they could just be the one and two. And the success of one does not necessarily mean that the other will just fade into obscurity.
And again, none of this is official, but there’s just been a lot of reporting around how it seems like OpenAI, more than anyone, is obsessed with and upset about Anthropic’s rise.
Our reporter Lucas [Ropek], he did a great piece over the weekend about the HumanX conference, where he was talking to everyone there and they’re sort of like, “Yeah, ChatGPT is fine, too,” but like they were all about Claude Code. And I think that is exactly what OpenAI is worried about.
Because again, in theory, there could be many other opportunities for generative AI, but it feels like the big growth area, the area where the most money is and where they could at least see a path to having a sustainable business in the future, is in these enterprise and coding tools.
#OpenAIs #existential #questions #TechCrunchAnthropic,Equity podcast,OpenAI](https://i2.wp.com/techcrunch.com/wp-content/uploads/2026/03/GettyImages-2266645295.jpg?w=1024&ssl=1 "OpenAI’s existential questions | TechCrunch
OpenAI has been all over the news recently, whether that news is about acquisitions, competition with Anthropic, or bigger debates about AI’s impact on society.
On the latest episode of TechCrunch’s Equity podcast, Kirsten Korosec, Sean O’Kane, and I did our best to round up all the latest OpenAI news. While the company’s latest acquisitions seem to be classic acqui-hires, Sean suggested they also address “two big existential problems that OpenAI is trying to solve right now.”
First, with the team behind personal finance startup Hiro, the company may be hoping to come up with a product that has “more hooks than just a chatbot, and maybe something worth paying more for.” And with new media startup TBPN, OpenAI could be looking to “better shape its image in the public eye, which lately has not been great.”
Read a preview of our conversation, edited for length and clarity below.
Anthony: [We have] two deals that are worth mentioning, one is that OpenAI acquired this personal finance startup called Hiro. And that comes after another deal that was literally announced when we were recording our last episode of Equity, so we didn’t get to talk about it: OpenAI had also acquired TBPN — a business talk show, like a new media company.
And I think both of these deals are pretty small compared to the scale of OpenAI. These are not things that people expect to really change the course of their business or anything like that, but they’re interesting because it suggests that there’s still this [attitude of,] “Let’s try out different things.”
Especially [with] the TBPN deal […] particularly at this time when it feels like OpenAI, from all the reporting we’re reading, is also trying to really refocus on making ChatGPT and its GPT models really competitive in an enterprise context with programmers.
Techcrunch event
San Francisco, CA
|
October 13-15, 2026
Is running a tech talk show, should that really be on the to-do list?
Kirsten: No, this should not be on the to-do list. That’s it.
I do want to mention Hiro because to me, that’s an interesting one, because Julie Bort, our venture editor, super talented, she wrote about this and was I think the first to write about it. She dug in a little bit and basically this looks like an acqui-hire. The company is folding. They basically said, “By this date, you won’t be able to access this anymore.”
This is a personal finance startup. And they only launched two years ago. So this absolutely is about getting talent on board. So I’m very curious to see if OpenAI is going to be just absorbing them into the ether at OpenAI, or if they’re actually interested in some sort of personal finance product that they want to work on. To me, it’s not really clear.
Sean: I think you look at both of these as acqui-hires to a certain extent. I mean, the TBPN acquisition, allegedly they are going to retain their editorial independence on the show that they make every day. And all respect to those guys who’ve put that out there and gotten it off the ground so quickly and grown it into what it has become.
I think any person who follows the media should have a healthy dose of skepticism that when you acquire something like that and you put the people who make the show under the org of the public policy people and comms or marketing adjacent people higher up at the company making the acquisition, that you could have good questions about whether or not saying “editorial independence” is enough. It’s not an incantation that just works.
But you know, what’s interesting to me about these two, while they are similar in their acqui-hire-ness, I think they both represent two major problems that OpenAI is facing.
One is Hiro. OpenAI has a very successful product in ChatGPT. As far as whether or not that will actually ever make them enough money to become a sustainable business that’s not raising the largest private rounds in the world, ever, to keep things going, is a big question. And they also seem to be struggling to keep up on the enterprise side of things where the real money seems to be, so bringing in a team like this seems like taking a shot at, “What else can we do?”
The guy who founded Hiro seems to have a serial entrepreneur streak of creating consumer apps, and so this seems to me like a bet on them being able to come up with something else that may have more hooks than just a chatbot, and maybe something worth paying more for.
And then TBPN is an acquisition made to help better represent what the company does and better shape its image in the public eye, which lately has not been great and certainly is under more questions now than just a few weeks ago, because Ronan Farrow just led a report at The New Yorker that dropped suspiciously right around the time that this and a couple other announcements from OpenAI came out last week.
I think those are two big existential problems that OpenAI is trying to solve right now.
Kirsten: So the thing that you didn’t say is, there’s Anthropic kind of looming in — not in the shadows, I mean, they’re very much taking up a lot of space here — but they’re having a lot of success on the enterprise side of things.
It feels like these guys are competitors and they also feel like very different companies in a lot of ways. Anthony, I’m wondering if you see them as direct competition to OpenAI? Or [are they] just finding their stride in enterprise and in a way, these two companies are clearly going to coexist and they’re really not directly competing with each other — maybe on talent, but not necessarily as we initially thought of them?
Anthony: I think they’re directly competing with each other. There’s definitely a scenario where if AI as an industry, as a technology, is as successful as its proponents hope for, they could both be very successful companies, they could just be the one and two. And the success of one does not necessarily mean that the other will just fade into obscurity.
And again, none of this is official, but there’s just been a lot of reporting around how it seems like OpenAI, more than anyone, is obsessed with and upset about Anthropic’s rise.
Our reporter Lucas [Ropek], he did a great piece over the weekend about the HumanX conference, where he was talking to everyone there and they’re sort of like, “Yeah, ChatGPT is fine, too,” but like they were all about Claude Code. And I think that is exactly what OpenAI is worried about.
Because again, in theory, there could be many other opportunities for generative AI, but it feels like the big growth area, the area where the most money is and where they could at least see a path to having a sustainable business in the future, is in these enterprise and coding tools.
#OpenAIs #existential #questions #TechCrunchAnthropic,Equity podcast,OpenAI")
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