Late one night last week, or perhaps very early into the morning, Natalie Massenet placed a phone call to her longtime business associate Jens Grede that neither of them could have ever fathomed, but that nevertheless captured the essence of her position in the fashion firmament. Massenet, the serial entrepreneur behind Net-a-Porter and co-founder of the venture capital firm Imaginary Ventures, had built a sprawling business portfolio and social network that had become increasingly intertwined. And now she was telling Grede, himself a serial entrepreneur and the C.E.O. of Skims, Imaginary’s most consequential portfolio company, that she was suing his longtime business partner, Erik Torstensson—himself yet another serial entrepreneur, who also happened to be her business partner and, until May 2025, her life partner as well.