He lost his events and production company to the pandemic. The internal tool he built to stop wasting his own time became the product strangers emailed him to pay for, four days after it launched.

Ilai Szpiezak is a three-time founder, originally from Argentina and based in London, who came into tech "because of the pandemic" and stayed. With his co-founder Charlie Day he built Dolphin AI, won a UK government contract, and then noticed he was spending most of his day writing prompts. So he built something to fix that. That side tool, Pretty Prompt (a browser extension that improves any AI prompt in one click), launched on Product Hunt as the #2 product of the day, and within four days people were emailing to pay for it. The pivot wrote itself.

In this Ops or Die conversation with Katie Whitcraft and Maria Pienaar, Ilai makes the case that the model is becoming a commodity and the context you bring to it is the real advantage. He explains why "it doesn't know what it doesn't know" sits underneath every AI interaction, why he treats a prompt as a task he hands off rather than a conversation, and the one thing that separates a mediocre output from a 10x one: focus. Along the way the three of them get into the "LLM (large language model) passport" idea, the security "shield" that flags when you are about to paste an API key into a chatbot, the AI slop showing up in cold sales email, the ethics of creative AI, and why the skill the next workforce gets hired for is critical thinking rather than prompting.

If you have ever typed a lazy ask into ChatGPT, waited ten minutes, and gotten back something useless, this is the episode that explains why, and what to do about it.

Key topics: startup operations, AI prompting, prompt engineering, agentic AI, context engineering, LLMs as a commodity, browser extensions, product-market fit, pivoting, building in public, AI governance and security, creative AI ethics, ops stack, fractional COO, SmartOps

Guest: Ilai Szpiezak (Co-founder & CEO, Pretty Prompt)
Website: https://pretty-prompt.com
LinkedIn: https://www.linkedin.com/in/ilaiszp/

Hosts: Katie Whitcraft and Maria Pienaar

Katie Whitcraft: https://www.linkedin.com/in/katiewhitcraft/
Maria Pienaar: https://www.linkedin.com/in/mariapienaar/

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