We Hired Hackers to Break Our AI

Published 2024-10-06 · Updated 2026-05-23 · 8 min read · AI Ethics and Regulation · By Sahin Boydas

We hired a team of hackers to break our own AI. It was scary and eye-opening. I'm taking you inside our first AI red-teaming exercise—what we did, the crazy vulnerabilities they found, and how we're fixing them. This is a raw look at what it takes to build responsible AI.

The best advice I ever got about we hired hackers to break our ai came from a founder who'd failed at it three times.

We hired a team of hackers to break our own AI. It was scary and eye-opening. I'm taking you inside our first AI red-teaming exercise—what we did, the crazy vulnerabilities they found, and how we're fixing them. This is a raw look at what it takes to build responsible AI.

The Reality Nobody Talks About

Most people approach we hired hackers to break our ai with assumptions that made sense five years ago. The world has moved on. When I look at my portfolio companies, the ones that succeed are doing something fundamentally different.

The first thing to understand is that simplicity beats complexity every time. I've seen this play out across dozens of companies. The pattern is unmistakable.

At RemoteTeam, we learned this the hard way. We spent months going down the wrong path before realizing that the market doesn't care about your roadmap. Once we made the switch, everything changed.

Why Most Approaches Fail

Let me be direct: about 70% of the approaches I see to we hired hackers to break our ai are fundamentally flawed. Not slightly off. Fundamentally flawed.

The root cause is usually one of three things:

  • Copying what big companies do without understanding why they do it. What works for Google doesn't work for a 10-person startup.
  • Over-engineering the solution when a simple approach would work better. I've seen teams spend six months building something that could have been done in two weeks.
  • Ignoring the human element. Technology is the easy part. Getting people to actually use it is where the real challenge lives.

The AI Angle

I can't talk about we hired hackers to break our ai in 2026 without mentioning AI. As someone who's invested in Anthropic, OpenAI, Scale AI, and Hugging Face, I have a front-row seat to how AI is transforming this space.

The short version: AI makes good practitioners better and bad practitioners worse. It's an amplifier, not a replacement.

I've seen companies use AI to 10x their we hired hackers to break our ai capabilities. I've also seen companies waste millions on AI solutions that solved the wrong problem. The difference comes down to understanding what you're actually trying to achieve.

This connects to broader themes around EU AI Act, deepfakes, AI regulation 2026 that I've been thinking about a lot lately.

What's Next

The world of we hired hackers to break our ai is moving fast. What worked last year might not work next year. That's both the challenge and the opportunity.

My advice: stay curious, stay humble, and stay close to the people who are actually doing the work. Read less thought leadership and do more experiments. Talk to fewer consultants and more practitioners.

And if you're a founder building in this space, remember that the best time to get we hired hackers to break our ai right is before you need to. Don't wait for a crisis to force your hand.

I'll keep sharing what I learn. This stuff matters too much to keep to myself.

Frequently Asked Questions

What's the most common pushback you get on this?

People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.

What experience informs this perspective?

This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.

Do all experts agree with this view?

No, and that's fine. The best ideas in business are often contrarian. I share my perspective based on my experience and data, but I encourage you to seek out opposing viewpoints and form your own conclusions.

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