Responsive, affordable space transportation, using reusable launch vehicles (RL Vs) to place payloads into orbit at a fraction of today's exorbitant costs, will become a reality within the next few decades. As the railroads unlocked the American West, and as the modern airplane shrank our planet, reusable launch vehicles will open space with vast scientific, commercial, humanistic, and military payoffs. The large amount of financing required for commercial RLV development coupled with significant market risk, the employment of a myriad of high-risk technologies, the lack of Federal assistance beyond early stage RLV technology development, and numerous other barriers to entry have greatly undermined successful RLV system development. Historically, the U.S. government has stepped into the fray of past transportation technology and infrastructure development with investments and funding incentives. Over the past two decades, however, the U.S. government's record in RLV development has been dismal, characterized by repeated attempts to leapfrog critical technologies rather than applying a pragmatic, stepping stone, "build a little, fly a little" approach that was so successfully utilized in experimental aircraft development a few decades before. Despite a number of failed launch vehicle development endeavors since the development of the Space Shuttle, a wave of private entrepreneurial firms are currently attempting to develop innovative reusable launch vehicle concepts independently of the U.S. government. Originally bolstered by a late 1990s bullish low Earth orbit (LEO) market, the success of these endeavors may be destined to echo that of an analogous wave of failed entrepreneurial expendable launch vehicle development efforts from a few years before, especially now that the LEO market has declined so drastically. This thesis addresses several aspects of the development of reusable launch vehicles. Demand for space launch is examined, with attention on commercial satellite trends and emerging markets. Space launch supply is assessed, with discussion of the current situation of launch vehicle over-capacity and high global competition. Several reusable and expendable launch vehicle development programs are examined, including the efforts of both small entrepreneurial ventures and large national programs. An introduction to barriers to entrepreneurial RLV development is also presented, focusing on legitimacy issues and the problems of financing such high-risk ventures. Finally, technology and market entry competitive strategies for entrepreneurial RLV ventures are discussed and recommendations offered.