Meet Our Team
Alan Cashdollar, M.Ed.
CEO & Founder
If you grew up in North Florida in the 80s, there’s a good chance you saw a young Alan Cashdollar tearing up the BMX track, checkmating opponents in chess, or smashing forehands on the tennis court. With three sisters keeping him on his toes and a mom who worked as a nurse in a maximum-security prison, Alan learned early about grit, focus, and a good sense of humor.
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In the late 80s and early 90s, Alan swapped the
helmet for a microphone, recording four albums​​​ with his rock band Sistene Slam—because why not? In 2002, he went solo with an ambitious project called 12, recording 12 songs on a 12-string guitar in just 12 hours. The album earned rave reviews and can still be found on SoundCloud for anyone curious enough to give it a spin. After the music scene, Alan hit the books at Stetson University, earning a degree in English with minors in Leadership and History. He returned home to teach high school English and journalism while coaching varsity soccer at Bradford High School. Three years later, he headed north to teach at the prestigious Eagle Hill School in Greenwich, Connecticut, helping students with learning differences unlock their potential. Along the way, he earned his master’s degree in Educational Technology at Pace University, focusing on assistive technologies. From there, Alan became the Upper School Learning Specialist at The Allen-Stevenson School for boys in Manhattan, then took the leap into entrepreneurship—founding his own tutoring company in 2012. He later served as VP of Education at Mentored.com, where he trained over 400 tutors and led the development of three educational platforms. When the world shut down in 2020, Alan shifted gears to help frontline workers’ children keep learning, serving as Virtual Tutoring Director for Vivvi and eventually partnering through his company, Clear Prep Learning, to deliver thousands of online sessions. With over 10,000 hours of one-on-one tutoring (5,000+ of those online), Alan blends experience, creativity, and a dash of rock-and-roll energy into everything he does. These days, his latest passion is competing in World Series of Poker tournaments, finding them a great place to challenge himself and grow. Alan lives in Jersey City with his wife, Venesha—a fellow educator and Head of Student Support at The Allen-Stevenson School—and their daughter, Cameron, who’s studying neuroscience at the University of Delaware. They spend their summers in the Pocono Mountains, where you might catch Alan playing guitar on the porch… or practicing his poker face.
Janette Kennedy, MAEd, MFA
Director of Enrollment and Operations
Meet Janette Kennedy, a creative force who thrives at the intersection of technology, writing, and education. She's spent her career helping others find their voice by bringing a unique blend of analytical problem-solving and innovative thinking to every challenge.
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Fresh out of college in the late 1990s with degrees in English and Philosophy, Janette jumped into the burgeoning world of websites. As the bridge
between creative and tech teams at an advertising agency, she helped build new digital platforms and discovered her passion for what's possible with new technology. That excitement for innovation led her to the classroom, where she earned a master's degree in Curriculum and Instruction at the College of William and Mary. There, Janette continued to explore how creative technology can enhance learning, designing "webquests" and demonstrating how graphic novels and comics can be powerful learning tools. At Eagle Hill School, she put this approach into practice, teaching both math and writing while developing curricula for neurodivergent students. She even created her own "Technology Applications for Study Skills" program to help students overcome barriers. Always looking to empower others, she designed professional development guides for fellow educators and co-taught a graduate class at Columbia University. Janette's problem-solving skills extend beyond the classroom. She stepped into leadership roles, co-managing a remote team of over 40 tutors as Virtual Tutoring Coordinator for Vivvi. Her entrepreneurial spirit also led her to found her own coaching business, where she worked directly with young adults on their most challenging reading, writing, and research projects. Today, Janette is the Director of Enrollment and Operations at CLEAR Prep Learning, all while continuing to teach undergraduate writing and literature courses. A published poet and Pushcart Prize nominee, her collection Backbeat Ocean is a testament to her artistic exploration. Whether she's judging writing awards, authoring articles on family advocacy, or presenting on executive functioning, Janette's unique passion and creative energy shine through. When she's not working, you can find Janette exploring a new project, writing, or getting lost in a good book. Her absolute favorite thing, though, is joining her husband to cheer on her soccer, singing, and theater-loving teens from the sidelines.