Sam Altman’s 5 most awkward public moments

The tech billionaire, Sam Altman, is one of the most recognisable figures in the tech industry, constantly pushing the boundaries of artificial intelligence (AI).

Known as the face behind ChatGPT and one of the loudest voices in the artificial intelligence (AI) revolution, Altman has built his reputation as a visionary leader with grand ambitions of shaping the future.

However, behind his achievements lies a track record of every time he has embarrassed himself in public.

Awkward moments of the OpenAI CEO

Below are five of Altman’s most embarrassing public moments

1. “Genuinely embarrassed” by OpenAI’s harsh NDAs

In 2024, an investigation revealed that OpenAI employees were being forced to sign unusually restrictive off-boarding agreements.

These included lifetime non-disparagement clauses that essentially gagged ex-employees from ever criticising the company — or even admitting they signed an NDA.

When the story broke, the backlash was swift. Former staffers accused OpenAI of hypocrisy, given its public mission of transparency.

Altman later admitted this was “one of the few times I’ve been genuinely embarrassed running OpenAI.”

He claimed he hadn’t known such clauses existed in company documents but accepted responsibility for not catching them earlier.

2. GPT-5’s launch fiasco

The highly anticipated launch of GPT-5 last month was supposed to be a crowning achievement for OpenAI.

Altman had hyped the model as the “smartest AI ever,” yet within hours, users began complaining of bugs, slow responses, and missing features.

Even worse, GPT-5 stripped away much of the “personality” that many users cherished in earlier models, especially those who relied on it for companionship.

Facing mounting frustration, Altman hosted a Reddit AMA where he candidly admitted, “We totally screwed up.”

3. The TED 2025 interview

At the prestigious TED 2025 conference in Vancouver, Altman sat down with TED head Chris Anderson for what should have been a celebratory interview.

Instead, it turned into one of the most uncomfortable exchanges of his career.

Anderson pressed Altman repeatedly about OpenAI’s shift from nonprofit to a $300 billion for-profit powerhouse.

Altman’s attempts to defend OpenAI’s direction often sounded defensive, and his vague responses about handling power made the moment more awkward.

4. Dodging finance questions

Altman has often appeared visibly irritated when pressed on OpenAI’s financial structure. 

In May 2024, during separate interviews, he dismissed finance-related questions as “the most boring question I can imagine.”

On another occasion, when MIT’s president asked him about AI’s impact on finance, he sidestepped and suggested the discussion move on.

The most awkward moment came at Stanford, where he dodged queries about OpenAI’s profit-versus-nonprofit nature, leaving the interviewer visibly frustrated.

5. The Fallout of over-promising AI

Altman is known for bold predictions and sometimes too bold. He once called GPT-4 “mildly embarrassing” and promised GPT-5 would change everything.

But when reality didn’t meet the hype, critics accused him of overpromising. The disappointment amplified the sense that Altman sometimes lets ambition get ahead of execution.