Linda Jenkinson, Chairman and CEO of luxury personal services company, LesConcierges (LC), hung up the phone after checking her voicemail in July 2007. She had just received a message from Randy Haykin, an angel investor and board member who had participated in the Series C round that Jenkinson recently raised. After an initial “honeymoon period,” she and Haykin had started disagreeing on internal matters, most recently about whether to hire an interim CFO while the company took time to source a permanent candidate. Jenkinson began to wonder whether Haykin had been the best choice for the board and if there was anything she could do to work with him more effectively. Unbeknownst to Jenkinson, Haykin was simultaneously considering whether his investment in LesConcierges would turn out to be the “home run” that he had originally anticipated. He also questioned how he could help solve the challenges facing the company’s CEO without damaging their relationship in the process.