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Building Trust in a Divided World with Jess Flynn | Ever Onward - Ep. 86
Manage episode 499610529 series 2591441
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What does it take to build a thriving business while making a lasting impact on your community? Jess Flynn’s journey from reluctant Idaho transplant to respected PR agency CEO is a masterclass in authentic leadership.
As Founder and CEO of Red Sky, a Boise-based PR and marketing agency, Jess brings 25 years of journalism and PR expertise to a diverse portfolio of clients. She leads the agency’s reputation management and executive training programs, advising private- and public-sector leaders through high-stakes communications and crisis response. An Emmy Award-winning former broadcast journalist, she began her career after graduating from the University of Texas and eventually returned to Idaho to launch Red Sky in the middle of the 2008 recession.
Under her leadership, Red Sky has been named the Boise Chamber’s 2025 Small Business of the Year (under 10 employees) and built a team known for long-term loyalty, with staff tenures ranging from four to fifteen years. Jess credits this culture to surrounding herself with people who challenge her perspective—one of her guiding principles as a leader.
Her influence extends beyond business. She has served as a federal appointee to the National Women’s Business Council, led its Rural Subcommittee, and acted as an Honorary Commander of the Idaho Air National Guard. She currently serves as a Director of First Federal Bank and is President-Elect of the Women’s and Children’s Alliance.
In this episode, Jess reflects on the evolving media landscape, the growing need for trusted communications, and the double-edged sword of artificial intelligence in the industry. She shares her strategies for balancing business growth with authentic connection, creating cultures where people stay, and focusing energy on what truly matters.
Whether you’re an aspiring entrepreneur, a seasoned executive, or simply someone passionate about strengthening communities, Jess’s story offers practical strategies and an inspiring vision for leading with trust in today’s divided world.
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Chapters
1. Introducing Jess Flynn of Red Sky (00:00:00)
2. Alquist Update: The Homedale Project (00:05:13)
3. New York to Boise: Finding Home (00:14:36)
4. Building Red Sky PR Agency (00:24:17)
5. Leadership Qualities and Self-Awareness (00:33:43)
6. Media Evolution and Trust Crisis (00:38:18)
7. AI's Impact on Communication (00:46:41)
8. Travel, Growth, and Idaho's Future (00:53:24)
156 episodes
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