The failure of a business can often be anticipated over varying periods of time. But how does this anticipation influence the likelihood and timing of an entrepreneur’s reentry? From an anticipatory grief perspective, we propose that the number of years a firm experiences financial distress—an indicator of the entrepreneur’s anticipatory grief due to the increased likelihood of bankruptcy—has an inverted U-shaped relationship with the likelihood of the entrepreneur reentering entrepreneurship after failure. Additionally, for those entrepreneurs who do reenter after failure, we propose that the relationship between the number of years of pre-failure financial distress and the time to entrepreneurial reentry is U-shaped. Finally, we consider whether the business owned by the failed entrepreneur was a family business and theorize about the corresponding moderation effects. Testing our hypotheses on a sample of over 10 thousand failed entrepreneurs from Sweden generally supports our theorizing, offering valuable contributions to the literature on entrepreneurs’ reentry, entrepreneurial careers, and anticipatory grieving.
