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A never diluted, designer-made newsletter to keep you updated with the latest news.

In a quaint town in Indiana, a 14-year-old boy named Simon grappled with the perils of alienation. Fresh off the boat from Russia and barely understanding a word of English, he often felt lost. One day, in an act that would transform Simon's life, his English teacher gave him a book, saying, "Read this book with a dictionary, Simon, and your English will improve." She was right. Years later, the same perseverance Simon had shown in mastering the English language became a beacon in the tech world. After aiding RingCentral's meteoric rise from $200M to $2B in ARR, he felt the urge to solve a challenge close to his heart: the funding issues faced by private schools. Drawing from personal experiences and a deep-rooted belief in the power of education, Simon established ChalkBooks. His aim? To ensure that schools could raise sufficient funds to hire exceptional teachers and offer scholarships, transforming countless lives. Traditional fundraising CRMs, designed with generic non-profits in mind, left much to be desired. They overlooked essential roles in the fundraising matrix, from trustees and volunteers to school staff and families. ChalkBooks filled this void, introducing the first task and communication-centric workflow software tailored specifically for school fundraising teams. The system, empowered by AI, automates processes that were once tediously managed on spreadsheets. It fosters stronger donor relationships, translating into increased donations.

A testament to Simon's unwavering spirit, when ChalkBooks faced its first significant challenge—a product built on advisor insights but lacking actual users—he had a choice. He could pivot to another market segment or stay true to his vision. Simon chose the latter, focusing on creating a comprehensive system for private schools' fundraising teams. This gamble paid off. The company soon gained traction, acquiring ten customers, and setting its sight on loftier goals. Under Simon's leadership, ChalkBooks has become more than just a SaaS platform. Its core values, such as ALWAYS BE GROWING and EXPERIMENT BOLDLY, instill a culture of innovation, collaboration, and growth. The future seems bright, with ChalkBooks aiming to reach an ARR of $1M across approximately 100 schools. In the world where private schools grapple with deferred maintenance expenses due to the pandemic, ChalkBooks stands as an essential partner. With an emphasis on doing more with less, it promises to aid schools in navigating financial challenges and staying operational long-term. For those embarking on their entrepreneurial journey, Simon's advice echoes his life's lessons: "Early sales and substantial commercial progress at fast velocity solve nearly all fundraising challenges." As he has demonstrated with ChalkBooks, with vision, perseverance, and a deep understanding of one's target market, success is not just a possibility—it's a guarantee.

Reach out to Simon and explore the future of school fundraising at


Sep 20, 2023




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