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

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Manage episode 514885603 series 2522425
Content provided by Alex Bridgeman. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Alex Bridgeman or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

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

  continue reading

285 episodes

Artwork
iconShare
 
Manage episode 514885603 series 2522425
Content provided by Alex Bridgeman. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Alex Bridgeman or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

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

  continue reading

285 episodes

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