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OpenAI Wrestles with Existential Questions

OpenAI Wrestles with Existential Questions

June 22, 2026
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OpenAI Wrestles with Existential Questions

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OpenAI has been dominating headlines lately, covering everything from acquisitions and competition with Anthropic to broader debates about AI's societal impact.

In the latest episode of TechCrunch's Equity podcast, Kirsten Korosec, Sean O'Kane, and I wrapped up the most recent OpenAI news. The company's latest acquisitions appear to be typical acqui-hires, but Sean noted they also tackle "two big existential problems OpenAI is trying to solve right now."

First, by bringing in the team from personal finance startup Hiro, OpenAI may be aiming to develop a product with "more hooks than a simple chatbot—something people would be willing to pay more for." Meanwhile, acquiring new media startup TBPN could help OpenAI "polish its public image, which has taken a hit lately."

Below is a preview of our conversation, edited for brevity and clarity.

Anthony: There are two deals worth highlighting. First, OpenAI bought the personal finance startup Hiro. That follows another deal announced right as we were recording our last Equity episode, so we didn't discuss it then: OpenAI also acquired TBPN, a business talk show and new media company.

Both deals are relatively small for OpenAI. They're not expected to significantly shift the company's direction, but they're intriguing because they hint at a mindset of "Let's experiment with different things."

Especially the TBPN deal comes at a time when, based on what we've seen, OpenAI seems to be doubling down on making ChatGPT and its GPT models more competitive for enterprise developers.

Should running a tech talk show really be on the to-do list?

Kirsten: Absolutely not. That's all.

I want to highlight Hiro because I find it interesting. Julie Bort, our talented venture editor, was likely the first to cover it. She looked into it, and it appears to be an acqui-hire. The company is shutting down. They told users, "After this date, you won't have access anymore."

It's a personal finance startup that launched just two years ago. So this is clearly about hiring talent. I'm curious whether OpenAI will absorb them into its broader operations or if they're genuinely interested in building a personal finance product. To me, it's ambiguous.

Sean: I'd say both are essentially acqui-hires. For TBPN, they supposedly retain editorial independence on their daily show. I respect how quickly the team launched and grew it into what it is today.

Anyone following media should be skeptical. When you acquire a show and place its creators under the public policy, communications, or marketing teams at the acquiring company, saying "editorial independence" isn't a magic spell.

What I find interesting is that despite both being acqui-hires, they each highlight a key problem OpenAI is facing.

The first is Hiro. ChatGPT is a hit, but whether it can generate enough revenue to make OpenAI a sustainable business—without relying on record-breaking private funding rounds—is a major question. They also appear to be struggling in the enterprise space where the real money lies. So bringing in a team like this is a bet on "What else can we do?"

Hiro's founder has a track record of building consumer apps, so this looks like a bet that they can create something with more depth than a chatbot—something people would pay more for.

TBPN is meant to help OpenAI present itself better and improve its public image, which has been suffering. The timing is notable: Ronan Farrow's New Yorker report dropped right around the same time as these announcements last week.

Those are two existential problems OpenAI is currently trying to address.

Kirsten: What you didn't mention is Anthropic looming large. Not in the shadows—they're very visible—and they're finding significant success in the enterprise.

They seem like competitors but also very different companies in many ways. Anthony, do you see them as direct rivals, or are they just finding their footing in enterprise? Could they coexist without directly competing—maybe on talent, but not in the way we initially imagined?

Anthony: I think they're direct competitors. If the AI industry lives up to its promise, both could be huge—number one and two. Success for one doesn't mean the other fades away.

None of this is official, but reporting suggests OpenAI is more obsessed and rattled by Anthropic's rise than anyone else.

Our reporter Lucas Ropek wrote a great piece about the HumanX conference over the weekend. People there said, "ChatGPT is fine, too," but they were all about Claude Code. That's exactly what OpenAI fears.

In theory, generative AI has many opportunities, but the biggest growth area—where the money is and where a sustainable business path exists—is enterprise and coding tools.

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