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Resilience and Vulnerability: JHW Enterprises CEO Shares His Leadership Journey

Written by Amber Stewart, 2023 Fall Leadership Discovery participant

There was no better way to kick off the Chamber’s Leader Discovery class than learning from Jaymes McCloud, founder, and CEO of JHW Enterprise and a board member of the Charleston Chamber of Commerce. Jaymes’ personal experience of facing adversity truly spoke to his wisdom as he discussed developing leadership skills for organizational impact and the capabilities needed to drive positive change within an organization.

Jaymes began his career in property management right after college, starting as a leasing agent and eventually working his way up to become the VP of Property Management. During his time with the company, he played a pivotal role in the company’s growth, establishing solid policies and procedures that laid the foundation for its success. However, life took an unexpected turn when Jaymes attended a conference with the company’s executives, only to be blindsided with the news that he would no longer be part of the team. This news came at a difficult time for Jaymes and his family, as they were preparing to move to Atlanta.

Feeling defeated and unsure of how to support his family, Jaymes received a timely call from a good friend who sparked his interest in starting over and leading a life with impact and purpose. This marked the beginning of JHW Enterprise, a highly successful multi-state, multi-family and investment property management firm, which Jaymes founded to leave a path and legacy for his children.

Building a successful business from scratch was not easy, but Jaymes was determined to surround himself with leaders who could help him think strategically, emphasizing the importance of being vulnerable and asking for help. He shared how effective leaders inspire their employees to perform at their best and motivate team members to work towards shared goals. Trust is a crucial element in leadership, and when hiring, Jaymes looks for individuals who value people and service. In today’s world, where truth, transparency and clarity are highly valued, Jaymes believes that without these qualities, people will not follow you as a leader.

My personal key takeaway from Jaymes’ presentation is his commitment to mindfulness and self-reflection. He sets aside 15 minutes every day for mindfulness and lunch, using this time to reflect on what is working well and how to improve and grow those aspects. This serves as a reminder to give oneself permission to pause and take time to reflect, which ultimately demonstrates respect for one’s own time and shows employees that their time is valuable.

With his guidance and wisdom, we are reminded that we have the power to make a profound impact in our organizations and leave a lasting legacy even when faced with the unexpected and starting over. So, when life hands you lemons, remember to turn them into the sweetest lemonade imaginable.

Interested in learning about Leadership Discovery? Find more information here.

Posted on
September 28th 2023
Written by
Justin Allen
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