Transforming Education for Underserved Students with Alyssa Bowlby

SummaryIn this episode of ‘Tell Me More,’ CJ Quartlbaum engages in a deep conversation with Alyssa Bowlby, exploring the intersections of education, socioeconomic status, and personal growth. Alyssa shares her journey from professional opera singer to founder of the Yleana Leadership Foundation, which significantly improves college graduation rates for underserved students. They discuss the challenges faced by students in underfunded education systems, the importance of mentorship, and the impact of adverse childhood experiences on learning. The conversation also touches on the ethics of capitalism, the need for genuine political leadership, and the importance of fostering a culture of inquiry in children. Ultimately, the episode emphasizes the power of hope and the potential for change in both education and society.Alyssa Bowlby is a nonprofit founder, strategist, and leader who has spent the last twelve years building and scaling programs at the intersection of education, equity, and innovation. As Co-Founder and Executive Director of the Yleana Leadership Foundation, she transformed a three-week pilot summer program into a four-city, 10+ year wraparound model serving more than 1,500 first-generation, low-income, and BIPOC students from New York City, Boston, Philadelphia, and Baltimore. Under her leadership, Yleana students achieved 130–180 point SAT gains over three weeks and an 83% college graduation rate—approximately eight times the national average for their demographic.Alyssa led Yleana’s growth from a $350K budget to a $1.7M operation, raising $8.7M across major gifts, foundations, government contracts, and earned revenue, and building an over-50% earned-revenue model to support long-term sustainability. She also conceived, designed, and product-managed apply.yleana.org, a $400K+ in-house technology platform that centralized student admissions, diagnostics, SMS-based persistence coaching, and real-time reporting for funders and partners. The platform was recognized as a finalist for the NYC Imagine Awards for Innovation.Today, Alyssa focuses on helping mission-driven organizations scale without losing their core values—through rigorous fundraising strategy, data-informed systems, and partnerships that reflect and respect the communities they serve. She currently leads fundraising strategy as a volunteer for Swing Blue Alliance, where she has rebuilt donor operations, coached an experienced team of volunteers, and introduced more data-driven approaches to grassroots fundraising. She is at her best where bold vision meets operational discipline, and where the work expands opportunity in tangible ways for people who need support.Check out her YouTube Channel Alyssa the College ExpertFollow me on Instagram: CJ_QuartlbaumWatch the full conversation on YouTubeListen on AppleListen on Spotify Get full access to CJ's Substack at tellmemorewithcj.substack.com/subscribe