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Dan Calano
Two-time search-fund entrepreneur and operator with prior experience as CEO of Utility Cloud and current CEO of Fleetflo; focuses on building trust in M&A, talent management, and process-driven growth.
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Oct 21, 2025
• 1h 12min
Right to Win Series EP.2: Building Trust as Second-Time CEO with Dan Calano - EP. 273
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Dan Calano, a two-time search-fund entrepreneur and current CEO of Fleetflo, shares his invaluable insights on building trust and navigating the complexities of leadership. He reflects on overcoming challenges like intellectual property disputes during his acquisition of Utility Cloud and emphasizes the importance of transparency in building relationships with sellers. Dan also discusses the significance of thoughtful hiring practices, recovering from COVID-related setbacks, and how his experiences shaped a more confident and strategic approach in his second CEO role.
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