A costly advertising mistake at Handy taught Alex Levin valuable lessons about leadership that he now applies at his AI startup, Regal. Levin, who overspent by $800,000 on a Google ad campaign for a new handyman service, credits the experience for shaping how he manages his current team.

At Handy, Levin was responsible for launching a new service with a $1 million budget. A team member failed to set a daily spending limit on Google ads, resulting in the massive overspend. Levin took full responsibility, admitting he should have monitored the account more closely. His boss's measured response - focusing on solutions rather than punishment - became a defining moment in his management philosophy.

Levin now encourages his team at Regal to take calculated risks and learn from mistakes. He's implemented strict spending limits and emphasizes transparency when errors occur. The experience taught him that punishing mistakes stifles innovation, while creating a culture that accepts new errors (but not repeated ones) fosters growth. His approach balances accountability with psychological safety, recognizing that in programmatic marketing, the infinite inventory requires careful guardrails. The $800,000 lesson continues to influence how he builds his company's culture and manages risk.