One unintended consequence of entrepreneurial success may be that the entrepreneur becomes intertwined with the business. This phenomenon is called entrapment and we draw on Becker’s Side-Bet Theory to develop a series of hypotheses based on entrepreneurial success and individual difference variables. We surveyed 122 active entrepreneurs and found several significant relationships. To better understand these relationships, we conducted a second study using qualitative interviews with six entrepreneurs. Interview data suggested that entrepreneurs do indeed make side-bet type commitments, but increased financial success allows for the honoring of those commitments. The ability to honor commitments appears to leave the entrepreneur with a greater sense of alternatives and thereby reduces feelings of entrapment.