CEO's $800,000 Mistake Taught Valuable Leadership Lesson

The CEO of an AI startup says a major gaffe he made earlier in his career taught him what good bosses do when employees screw up.

Published on Mar. 4, 2026

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Alex Levin, the CEO of AI startup Regal, recounts a major mistake he made earlier in his career when he was a senior VP at Handy. Levin's team accidentally spent an extra $800,000 on Google ads without a daily spending limit, a mistake Levin takes responsibility for. Levin's boss at the time handled the situation well, which taught Levin the importance of quickly owning up to mistakes and using them as learning opportunities rather than placing blame. Levin now applies these lessons at Regal, where he encourages his team to raise issues quickly and sets strict guardrails to prevent similar mistakes.

Why it matters

Levin's experience highlights the importance of leadership and company culture when it comes to how organizations handle employee mistakes. By taking responsibility and using the incident as a learning opportunity, Levin's boss demonstrated the kind of approach that can foster an environment where people feel empowered to be transparent about errors, which is crucial for innovation and growth.

The details

While at his previous role at Handy, Levin was responsible for a $1 million budget to recruit handymen for a new service. Due to a mistake by someone on his team who failed to set a daily spending limit on Google ads, the company ended up spending an extra $800,000 with little return. Levin took full responsibility for the error, even though he wasn't directly responsible for the oversight. Rather than punishing Levin, his boss at the time handled the situation well, which taught Levin valuable lessons about leadership.

  • In 2026, Levin was the senior VP at Handy when the $800,000 mistake occurred.

The players

Alex Levin

The cofounder and CEO of Regal, a New York-based maker of AI agents for customer experience. Previously, he worked at Handy, which was later acquired by Angi.

Handy

An online marketplace that connects homeowners with local service professionals for home projects, where Levin previously worked as a senior vice president.

Regal

The AI startup that Levin co-founded in 2020, where he currently serves as CEO.

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What they’re saying

“I try to teach people at Regal that it's OK to make new mistakes, as long as you don't repeat them, largely because of my past experience making a major one.”

— Alex Levin, CEO, Regal (Business Insider)

“I always tell people I want bad news fast. Good news can be slow. You need to identify that you made a mistake so it doesn't keep happening.”

— Alex Levin, CEO, Regal (Business Insider)

What’s next

Levin plans to continue applying the lessons he learned from his $800,000 mistake at Handy to how he runs Regal, emphasizing transparency, accountability, and using errors as opportunities for growth.

The takeaway

Levin's experience underscores the importance of leadership and company culture in how organizations handle employee mistakes. By taking responsibility and using the incident as a learning opportunity, Levin's boss demonstrated an approach that can foster an environment where people feel empowered to be transparent about errors, which is crucial for innovation and growth.