Right to Win Series EP.2: Building Trust as Second-Time CEO with Dan Calano - EP. 273

About this episode

Dan Calano shares insights from his experiences as a two-time CEO, focusing on trust, leadership, and navigating challenges in acquisitions.

In this second installment of the Right to Win series on Think Like an Owner, host Alex Bridgeman sits down with Dan Calano to unpack the lessons learned from his journey as a two-time search fund entrepreneur. Dan reflects on his first acquisition of Utility Cloud, navigating challenges like intellectual property disputes and customer concentration, and how trust, discipline, and process shaped his leadership. He then shares what it was like to sell the company, transition through an acquisition, and ultimately launch Grouper Companies and acquire Fleetflo for his second CEO chapter. They discuss: • Building trust with sellers through transparency, follow-through, and "show me" actions • The importance of hiring slowly, managing talent thoughtfully, and reducing organizational friction • Navigating customer concentration risk and recovering from COVID-era setbacks • The decision-making and emotional process behind selling a company • How Dan approached his second search and CEO role differently, focusing on autonomy, community, and process-driven risk-taking Links: Dan on LinkedIn - https://www.linkedin.com/in/dcalano/ Fleetflo - https://fleetflo.com/index.html Pacific Lake…

People in this episode

Host: Alex Bridgeman

Guest: Dan Calano

Topics covered

• building trust
• leadership lessons
• search fund entrepreneurship
• acquisition challenges
• talent management
• decision-making process

Keywords

• trust
• leadership
• acquisition
• search fund
• talent management
• COVID recovery
• decision-making

Mentioned in this episode

Organizations: Utility Cloud, Grouper Companies, Fleetflo, Pacific Lake Partners, Trilogy Search Partners

Places: COVID

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