OpenAI is shopping. In the span of two weeks, the company behind ChatGPT has snapped up a personal finance startup and a business talk show. On the surface, these look like talent grabs—classic acqui-hires to bulk up the team. But dig deeper, and you see a company wrestling with two existential questions that could determine whether it becomes the next Google or the next cautionary tale.
The Deals Nobody Saw Coming
First came TBPN, the buzzy founder-led business talk show that OpenAI acquired in early April. The deal was announced so quickly that the TechCrunch Equity podcast crew missed it during their last recording. TBPN's hosts promised to retain "editorial independence," a phrase that should trigger healthy skepticism in anyone who follows media. When you put content creators under the org chart of a company's public policy and communications team, independence becomes more aspiration than reality.
Then came Hiro, a personal finance startup that had only been around for two years. The company announced it was shutting down its service and folding into OpenAI. Julie Bort, TechCrunch's venture editor, was first to report the deal and noted what everyone suspected: this wasn't about the product. It was about the people.
Specifically, it was about Andrew Kortina, Hiro's founder, who has a track record of building consumer apps that people actually use. OpenAI didn't buy a personal finance app—it bought a serial entrepreneur with consumer instincts and a team that knows how to ship products fast.
Problem One: The Revenue Question
Here's the uncomfortable truth about OpenAI: ChatGPT is a phenomenon, but it's not yet a sustainable business. The company has raised the largest private funding rounds in history, yet it's still burning through cash at a rate that would make even SoftBank nervous. The enterprise market—where the real money lives—has proven trickier to crack than expected.
Enter Anthropic.
While OpenAI has been grabbing headlines with its CEO's world tour and media acquisitions, Anthropic has been quietly eating its lunch in the enterprise market. At the recent HumanX conference in Nashville, TechCrunch's Lucas Ropek found that developers weren't talking about ChatGPT. They were talking about Claude Code.
"Yeah, ChatGPT is fine, too," one developer told Ropek, before immediately pivoting back to Claude's coding capabilities. This is exactly what keeps Sam Altman up at night.
The enterprise and coding tools market represents the clearest path to sustainable revenue for AI companies. It's where budgets are largest, where integration matters most, and where technical users drive adoption. Anthropic has found its stride here while OpenAI has been chasing consumer glory.
The Hiro acquisition signals OpenAI's recognition of this problem. Kortina and his team are being asked to answer a critical question: What else can we build that people will pay for? ChatGPT Plus subscriptions are nice, but they're not enough. OpenAI needs products with more hooks, more stickiness, more reasons for users to open their wallets.
Problem Two: The Narrative Crisis
If the Hiro deal is about revenue, the TBPN acquisition is about reputation.
OpenAI's public image has taken a beating lately. Ronan Farrow's explosive New Yorker piece—"Sam Altman May Control Our Future. Can He Be Trusted?"—dropped suspiciously close to OpenAI's announcement of these acquisitions. The timing wasn't coincidental. OpenAI needed to change the conversation.
The article painted a picture of a company and a CEO that have moved fast, broken things, and accumulated power without sufficient oversight. It raised questions about OpenAI's commitment to safety, its governance structure, and whether the benefits of its technology will be distributed fairly or concentrated in the hands of a few.
For a company that wants to be seen as building the most important technology since electricity, this is a problem. You can't simultaneously claim to be developing artificial general intelligence for the benefit of humanity while looking like just another Silicon Valley startup playing by move-fast-and-break-things rules.
TBPN is OpenAI's attempt to solve this through content. By bringing a respected business talk show in-house, the company gains a platform to shape its own narrative. The hosts can interview OpenAI researchers, discuss AI policy with company executives, and present a more human face to a skeptical public.
Whether this works depends on whether anyone believes the "editorial independence" promise. History suggests they shouldn't. When a company pays your salary, your incentives change—even if nobody explicitly tells you what to say.
The Anthropic Shadow
Throughout all of this, Anthropic looms. The company founded by former OpenAI researchers has become the elephant in every room where AI strategy is discussed.
On the surface, the two companies could coexist. If AI becomes as transformative as its proponents claim, there's room for multiple winners. They could be the Microsoft and Apple of the AI era—different philosophies, different strengths, both wildly successful.
But OpenAI doesn't seem to see it that way. Multiple reports suggest the company is "obsessed with and upset about Anthropic's rise." The competitive tension is palpable, and it's driving decisions that might not make sense through any other lens.
The difference in approach is striking. Anthropic has focused relentlessly on enterprise and developer tools. It hasn't made splashy media acquisitions. Its CEO, Dario Amodei, hasn't embarked on a world tour. The company has kept its head down and built products that solve real problems for businesses.
OpenAI, meanwhile, has chased consumer attention, media coverage, and the aura of being The Future. This strategy has made it the most talked-about company in tech. It hasn't necessarily made it the most profitable—or the most sustainable.
🔥 Our Hot Take
OpenAI is at an inflection point that will determine its trajectory for the next decade. The company has built something remarkable with ChatGPT, but building a hit product and building a durable business are different skills. Right now, OpenAI is learning this lesson the hard way.
The acquisitions of Hiro and TBPN reveal a company trying to buy its way out of two fundamental challenges: finding sustainable revenue beyond chatbot subscriptions, and controlling a narrative that's spinning out of its grasp. These are smart tactical moves, but they're tactical. They don't solve the strategic problem.
That problem is this: OpenAI is caught between two identities. It wants to be the research lab building artificial general intelligence for the benefit of humanity—a noble, almost academic mission. But it's also a venture-backed startup with investors who expect returns, employees who want equity value, and competitors who aren't playing by the same idealistic rules.
The tension between these identities is showing. Every media acquisition raises questions about independence. Every consumer app experiment distracts from enterprise priorities. Every defensive move against Anthropic suggests a company more worried about its position than its purpose.
The next 12 months will be critical. OpenAI needs to prove it can build products that enterprises will pay premium prices for. It needs to demonstrate that its safety commitments are more than marketing. And it needs to show that it can compete with Anthropic without losing its soul in the process.
The shopping spree is understandable. But acquisitions don't solve existential questions—they just buy time to answer them.