Rural communities face many economic barriers and there are many challenges to finding solutions to address poverty, both of which have been heightened since the onset of COVID-19. At the time of recording, Mike Swindle was Hendry County Commissioner and Director of Workforce Development for Hendry County Schools. He has since been elected to Superintendent of Hendry County District School. Mike explains to us how COVID-19 affected the challenges Hendry County was facing before the onset of the pandemic, and the new challenges it has created for the community. He shares valuable information about what it takes to help students and other individuals defeat generational poverty and shared some of the successful outcomes of his program. He also expressed the need for change in how adult-learners are reached and encouraged to finish their degrees and provides us with some examples used by his program and the benefits they have seen. Mike explained what it is like to finish a certification program with Workforce Development for Hendry County and the ease of connecting students to jobs right after completion due to the high workforce demands. He shares the benefits his program has experienced through collaboration with other organizations, while also expressing the challenges rural communities face when trying to collaborate and how external entities can help minimize these challenges and support rural communities.