Gary Beasley went with his gut to leave his first job after few months, despite the general rule of thumb his mentors suggested of staying at a company for few years. This was only one of the many successful calculated risks he took to become the CEO and Co-Founder of Roofstock, a technology-enabled marketplace that provides tools to investors for evaluating, buying, and selling single-family rental homes. Beasley shares his experience of how to take charge in one's non-linear career track and how to manage transitions between varying levels of roles at one's company. You'll also hear tips on how to be a valuable CEO at a thriving organization and how to scratch the entrepreneurial itch.