Study Tree

Ethan Kaiser, a wrestler and below-average student at Drexel University, understood firsthand the struggle that half of all college students face: failing out. While many factors contribute to student dropout, Ethan noticed a pattern—many students lack fundamental skills like self-regulation, time management, and the ability to recognize when they're falling behind. This personal experience combined with the massive problem facing higher education institutions (losing tuition revenue when students drop out) sparked the idea for Study Tree.

Ethan initially coded the product himself as a solo founder. His early work was strong enough to win the Microsoft Imagine Cup's US competition in 2015, which led Microsoft to hire his team. However, this created an unexpected challenge: his entire team departed to work for Microsoft, forcing him to rebuild from scratch. In 2016, he brought on a co-founder from high school and assembled a new team. By 2017, Study Tree was ready to approach its first customers.

Without connections in academia, Ethan had to hustle. He cold called, sent numerous cold emails, and attended higher education conferences relentlessly. Notably, he couldn't even close his alma mater, Drexel University—the VP of Enrollment was new and had other priorities. His persistence paid off, and by 2017 he landed his first few contracts, generating less than $10k MRR (roughly $5k monthly). One customer did delay their launch by a year, representing the only significant churn to date, but this early traction validated the business model.

The key to Study Tree's growth wasn't a single viral moment or clever marketing—it was a combination of direct enterprise sales and proof of efficacy. Ethan created "impressive white papers" demonstrating the platform's impact on student retention. Once universities saw measurable results, word spread within the higher ed community. As Ethan noted, "universities don't really compete against each other and they share best practices. So if you become a best practice, you can grow at a relatively fast rate." The challenge is the long sales cycle and high customer acquisition complexity, which made it difficult to calculate a traditional CAC metric.

What didn't work: trying to close his own university without relationships, and being overly feature-focused rather than business-model focused in early iterations.

By 2018, Study Tree had scaled to 5-20 paying customers (the company prefers discretion on exact count), each paying an average of $70k annually based on enrollment size. This translates to roughly $30k MRR, a 6x increase in a year. With a team of 6 spread across Philadelphia, New York, and remote locations, the company is cash flow positive ("breakeven"). Ethan recently presented at conferences in San Francisco and San Diego, generating 10 new university leads. The momentum is strong enough that he's preparing to raise $750k on a convertible note ($6M cap, 15-20% discount) to fuel growth to $2.5-3M in ARR within 18 months. The next challenge: building systems and sales processes so he's not the sole rainmaker.