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

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 Partners

Trilogy Search Partners

(00:00:00) - Intro
(00:04:27) - Dan's background and career
(00:10:03) - Building trust and overcoming challenges
(00:23:19) - Navigating talent and reducing friction
(00:33:01) - Deciding to sell Utility Cloud
(00:37:51) - Reflecting on team and autonomy
(00:40:23) - Post-acquisition role and insights
(00:44:21) - Starting Grouper Companies
(00:45:32) - Autonomy and community
(00:50:36) - Second-time search and CEO experience
(01:04:59) - Approach to risk and decision making
(01:11:06) - Conclusion and final thoughts