Founded in California in 2012, Ravel Law Inc. (Ravel) was a legal tech start-up that developed groundbreaking legal analytics products. In 2017, Ravel’s co-founder and chief executive officer (CEO) was deciding between two very different paths to take the company—a decision that would shape Ravel’s future and ultimately determine how the CEO would exit the company. One path would lead Ravel to an acquisition or sale, and the other would allow the company to further develop its technology and eventually lead to an initial public offering (IPO). Should the CEO sell Ravel now and harvest its existing value, or should he hold on to the company and raise money to build internal capital for a future IPO? As the leader of Ravel, the CEO had to weigh the benefits and costs of fundraising for a third round of investor money against the benefits and costs of selling Ravel. While doing so, he also had to consider what would bring the most value to Ravel’s stakeholders as well as satisfy his personal interests in the venture and in an exit.
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