In mid-2011, as global markets corrected amid worldwide economic uncertainty, Drew Houston, co-founder and CEO of Dropbox, the fast-growing file synchronization and sharing company, found himself in a difficult, albeit enviable, situation. Houston, who had already raised over $7 million through two rounds of venture funding (one seed round and a Series A round) and developed a large and growing user base, began receiving significant investor interest. With positive cash flows and profitability achieved, additional financing was not necessarily needed. However, in order to pursue future strategic efforts, Houston knew that additional cash was essential. After all, Houston and his team had already successfully executed the freemium business model but they had a greater vision-one that included a "path" to one billion users. In order to achieve this goal, the team delineated a number of strategic initiatives: extending their popular consumer product to the enterprise segment; opening up a platform upon which to allow third-party developers to add services and applications in order to build scale; augmenting the consumer side through distribution partnerships; and finally, finding a way to transition itself from a web-based company to one that could service cross-platform mobile devices. The team also realized that they would need a robust balance sheet to compete with well-established industry leaders such as Google, Apple, Amazon, and Microsoft. They would also need to focus on strategic hiring initiatives and key acquisitions in order to carry out these goals. This case describes Dropbox's path from inception up to its Series B round of financing. Specifically, it focuses on the team's strategic decisions as well as questions surrounding the execution of each initiative. Additional considerations include how much financing to raise, at what valuation, which terms were most important, and with whom to partner.

This note describes the tasks that fill the working day of a venture capitalist. Those functions involved in investing (deal sourcing, due diligence, and related tasks) often receive the most attention from students. However, interviews with experienced venture capitalists found that as much or more time is spent working with existing portfolio companies. This note provides insight into each aspect of a venture capitalist's job: making investments, working with portfolio companies, and managing the venture capital firm as a business. The note is written heavily based on quotes, allowing experienced venture capitalists to describe their activities in their own words.

When entrepreneurs are successful in convincing venture capital firms that they are an attractive potential investment, they are presented with offers detailing many terms of the investment agreement. These are described in term sheets. Sorting through the myriad terms can be a daunting proposition for an entrepreneur. Yet, it is important for entrepreneurs to understand the terms of a proposed financing. These determine the payout the entrepreneurs will receive when the company is liquidated or sold (either to another company or to the public through and IPO), the dilution the entrepreneurs will suffer in the event of a future down round of financing, control of the board of directors, and other important matters. The Series A terms will also set a precedent for the terms of future financing rounds. This case presents a situation in which entrepreneurs receive term sheets from two venture capital firms. The two term sheets differ in many ways, and students are asked to evaluate them from the perspective of the entrepreneur.

Most venture capital profits come from a small percentage of investments, despite high expectations for each investment made. As a result, a small improvement in selecting portfolio companies can make a substantial improvement in fund results. This case describes the venture capital deal sourcing and screening process. It does not describe the due diligence process in detail, but focuses on initial screening-identifying those companies that the venture capitalist will evaluate in more detail. After describing the sourcing and screening process, the case describes a fictional venture capital firm, and provides a number of incoming investment opportunities to be evaluated. Students are asked to play the role of an associate at the firm, and tasked with reviewing these opportunities and determine how each should be handled-should they be rejected, should they contact the entrepreneur for more information, or should they refer the opportunity to one of the firm's partners.