Everything seemed to be going right for Jason Portnoy. While studying engineering at Stanford, his career took a sharp and unexpected turn upward when he met the CEO of a new startup — a company that became PayPal. He was soon offered a job, jumped on the rocketship and didn’t look back. The years that followed led him to success after success, and Jason became a prominent figure in the high-flying worlds of tech and venture capital. The money and opportunities were endless. In the meantime,...