In this powerful “From Failure to Launch” episode, host Keira sits down with Monica Grant Cohen, whose journey from a low-income, single-parent household to becoming a leader in philanthropy is nothing short of inspiring. As the eldest daughter who lost her father at age six, Monica shares how her mother’s unwavering strength shaped her—and why she honored her mom by adding her mother’s middle name to her college diploma. A first-generation college graduate who set out to be a guidance counselor, Monica’s path expanded to higher education, nonprofit innovation, and now community investment at DRW. She talks about her “Blue Sky Thinking” approach, the externship program she built from two employers to over fifteen, and her work tackling both headline-making and quiet crises. Along the way, Monica opens up about imposter syndrome, the realities of real access, and the deep influence of her mother on the woman she is today.