Selling "Chaos" to the Fortune 100 Almost Killed His Company (Kolton Andrus)

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His pitch — "let us break your systems on purpose" — thrilled engineers and terrified the Fortune 100 executives who signed the checks. So Kolton Andrus did something few founders have the nerve to do: he stopped using the very term his company was built on.

In this episode of We Built It Because We Had To, host Jonathan W. Buckley sits down with Kolton Andrus, founder, chairman, and CEO of Gremlin — the company that carried chaos engineering out of Amazon and Netflix and into the Fortune 100, then repositioned it as reliability engineering to win the enterprise. Kolton shares how a brand-new Gremlin landed Twilio and Expedia as its first customers, what a six-to-nine-month MSA negotiation taught him about enterprise sales, and why the COVID quarters were among the hardest of his life — a stretch in which he hired an outside CEO, rebuilt the product around standardization and reliability scores, and later stepped back into the CEO seat himself. He breaks down the real math behind the nines of uptime (and why five nines means things simply cannot fail), explains why reliability is a change-management and accountability problem more than a software problem, and tells the story of the customer Gremlin lost to an outage and won back. The conversation closes with his take on agentic AI: "10x the code means 10x the problems" — and why reliability guardrails matter more now than ever.

About the guest: Kolton Andrus is the founder, chairman, and CEO of Gremlin, backed by Amplify Partners, Index Ventures, and Redpoint. Before founding Gremlin in 2016, he built failure-injection systems at Amazon and Netflix, where his team helped take Netflix from three nines to four nines of uptime.

Connect with Kolton Andrus: https://www.linkedin.com/in/kolton-andrus-77315a2/
Learn more about Gremlin: https://www.gremlin.com

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Key Takeaways

Kolton Andrus founded Gremlin in 2016 after building failure-injection systems at Amazon and Netflix, where his team improved Netflix's uptime from three nines to four nines.

Gremlin rebranded from 'chaos engineering' to 'reliability engineering' to overcome Fortune 100 executives' resistance to the concept of intentionally breaking systems.

Gremlin's early customers included Twilio and Expedia, acquired during the company's early stages.

During COVID, Andrus hired an outside CEO, rebuilt the product around standardization and reliability scores, then returned to the CEO role himself.

Andrus emphasizes that reliability is fundamentally a change-management and accountability problem rather than purely a software problem, and warns that increased AI code generation requires stronger reliability guardrails.

Frequently Asked Questions

What was Gremlin's original pitch?

Let us break your systems on purpose — a concept that excited engineers but alarmed Fortune 100 executives who controlled budgets.

Why did Gremlin change its messaging from 'chaos engineering' to 'reliability engineering'?

The term 'chaos engineering' terrified enterprise executives, so Andrus repositioned the company's offering as reliability engineering to win Fortune 100 business.

What does 'five nines' of uptime mean?

Five nines means systems cannot simply fail — it represents an extremely high standard of reliability.

What major challenge did Gremlin face during COVID?

The COVID quarters were among the hardest of Andrus's life; he hired an outside CEO, rebuilt the product around standardization and reliability scores, and later stepped back into the CEO role himself.

What is Andrus's concern about agentic AI?

He states that '10x the code means 10x the problems' and emphasizes that reliability guardrails matter more now than ever.