When Andrea Bibbs, Owner of June Dragonfly, reflects on her leadership journey and her experience as a Legacy Leadership Executive, she doesn’t hesitate to call on her support system and highlight the contributions of other women entrepreneurs and mentors to her success. Seeing herself as a “solopreneur,” or someone who is building and running a business on their own without any employees, Andrea views her leadership trajectory as one centered in community value systems. Her approach is shaped and strengthened through relationships, something that her Upstander, Heather Gibbons, Founder of INMO Creative, and her Emerging Leader, Mayenie Conton, Georgia Institute of Technology, can greatly attest to. After a successful summer of achievements and collaboration, this trio represents the heart of our Executive-Upstander mentorship model, where growth, accountability, and support flow in every possible direction.
Building a Relationship with Trust in Mind
Andrea and Heather have been friends and business partners for years, even serving as each others clients at different points—experiences that have made their bond extremely special. However, stepping into the Executive-Upstander relationship has allowed them to engage on a deeper and more intentional level in their work and their mission.
Heather willingly volunteered to join the Upstander ranks because she wanted to move beyond reflection into action. “This felt aligned with the work I was already doing,” she shared in her interview with Mayenie. Heather reflected on her mindset since early 2020, where she has been “learning, unlearning, and sitting with discomfort.” The work that she does with Andrea was what she believed to be the next step in doing the work in a relationship with someone that she cares deeply for.
For Andrea, having Heather as an Upstander has been invaluable. Together, they have had honest conversations about racial relations, business development, and community-centered leadership, while also tackling practical challenges around the logistics of her work, like pricing her offerings and relaunching her website.
With an already established connection, their relationship can sometimes lead them off into tangents. This is purely driven by the passion that they have for the nature of this work. Andrea sees it as a strength. Heather sees it as a pathway to a stronger bond. Both agree that their conversations fortify their already formidable relationship
“Heather’s encouragement and perspective mean so much,” Andrea said. “She’s not just supporting me emotionally, she’s helping me actively grow my business and thrive.”
With an already established connection, their relationship can sometimes lead them off into tangents. This is purely driven by the passion that they have for the nature of this work. Andrea sees it as a strength. Heather sees it as a pathway to a stronger bond. Both agree that their conversations fortify their already formidable relationship
“When we talk about this work publicly, it encourages others to have these conversations with their own friends.” – Andrea Bibbs
The Upstander Perspective
Heather jumped at the opportunity to participate in the Upstander program as a mentor to Andrea. She had already engaged in the Seeing Whiteness program and saw this as an additional opportunity to further the work that she was already doing and wanted to do. It also gave her the chance to do the work with someone she considers a good friend. In addition to Seeing Whiteness, Heather is participating in a professional project through the National Center for Civil and Human Rights, which felt incredibly timely given what she might like to take away from this experience.
Both Andrea and Heather lead with excellence, and their leadership paths are naturally aligned, strengthening one another along the way. Heather’s leadership journey has always been about exploration and believing that she can learn from anyone, young or old, experienced or inexperienced. There is something to learn from everyone, and this is something where the duo are most similar: They are helping each other to be better people and leaders by supporting each other.
“Leadership can be hard and lonely, so it’s nice to have support from other people who are leading.”
– Heather Gibbons
Mentorship in Action with Unwavering Support
Andrea’s mentorship extends to her Emerging Leader, Mayenie, who has quickly become a trusted collaborator and source of fresh perspective.
“This is the first time I’ve had someone see the behind-the-scenes of my business,” Andrea reflected.
“Having Mayenie there to ask questions, challenge my thinking, and offer her generational perspective has been incredible. I couldn’t have pulled off my last big event, the MLB All-Star Sports Power Brunch, without her.”
For Mayenie, the experience has been equally transformative.
“Andrea is a true mentor. She’s growing my network, sharing resources, and showing me how to lead as a solopreneur,” she said. “I can run anything by her and trust she has my best interests at heart.”
The Ripple Effect of Mutual Aid
Both relationships have deepened Andrea’s leadership, allowing her to gain insights from two people whom she has deeply connected with regardless of age.
“I get perspective I wouldn’t have on my own,” she said. “Heather and Mayenie both help me grow, and I hope I do the same for them. This relationship reinforces how important it is to take the time to connect with someone as a mentor and really build that relationship.” -Andrea Bibbs
The relationship between an Executive and their Upstander is not based on mentorship, as learning is a two-way street. Their relationship takes this a bit further: Heather, Andrea, and Mayenie actively show up for one another, spending Wednesdays during the summer for cowork and brainstorming sessions at The LOLA.
While Heather’s work has undoubtedly contributed to the progress of Andrea’s business, the partnership has also provided Heather with invaluable insights and opportunities for growth.
“It is really important for everyone to have a thriving network,” Heather shared, “even if that means working through the personal aspects of life as much as the professional side.”
Through her collaboration with Andrea, a leader who built her own enterprise from the ground up, Heather is gaining firsthand access to a wealth of knowledge and a powerful network, proving that true collaboration is a reciprocal exchange that elevates all involved.
The LOLA is their space for Growth and Connection
Programs like Legacy Leadership thrive at The Lola, where leaders and their allies find community, resources, and intentional space for honest conversations. The relationships between Executives, Upstanders, and Emerging Leaders are strengthened by this environment, one designed to spark both personal and professional growth.
Support The Legacy Leadership Project
You can help sustain these powerful mentorship experiences for our mission-driven leaders. Donations to the Legacy Leadership Executive Membership provide resources, professional development, and the network necessary to keep this work alive.
Based on an interview conducted by Mayenie Conton, 2025
