I made an $800,000 mistake at my job. It taught me what good bosses do when an employee screws up.
Business Insider
March 4, 2026
AI-Generated Deep Dive Summary
Alex Levin, CEO of Regal, a startup focused on AI agents for customer experience, shares how a costly mistake during his tenure at Handy shaped his leadership philosophy. While overseeing a $1 million budget to recruit handymen for a new service, Levin and his team overlooked setting a daily limit on Google ads, resulting in an $800,000 loss with minimal return. Recognizing the error, Levin immediately informed his boss instead of hiding it, highlighting the importance of transparency in addressing mistakes. His boss’s measured response taught him that punishing errors discourages risk-taking and innovation, which are crucial for growth.
Levin emphasizes that while new mistakes are inevitable when venturing into uncharted territory, repeating them is unacceptable. At Regal, he fosters a culture where employees are encouraged to speak up quickly about issues to prevent recurring errors. This approach has led the company to implement safeguards, such as setting spending limits on marketing channels and infrastructure providers, as seen with one provider capped at $100 daily. These measures ensure accountability without stifling creativity.
Leadership plays a critical role in shaping team behavior. By reacting constructively to mistakes, leaders can create an environment where employees feel safe to innovate and learn from their missteps. Levin’s experience underscores the importance of turning mishaps into opportunities for improvement rather than focusing on blame. This mindset
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Originally published on Business Insider on 3/4/2026