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Today: November 30, 2025
May 6, 2024
1 min read

Knowing when to sell: The art of start-up investing


TLDR:

  • Venture capital firms celebrate capital raises but selling down stakes can be tricky.
  • Missing the exit window can turn a profitable start-up into a failure.

For most founders, the most festive moment in their start-up journey will be the capital raise announcement. Venture capital firms are almost unique in celebrating the buy in, and such investments are often accompanied by gushing praise for the start-up’s founders. This narrative makes selling down a tricky endeavour, open to misinterpretation that risks eroding that VC’s reputation as a true believer. However, missing the exit window has frequently turned a spectacular start-up gain into catastrophic failure, sometimes in very public circumstances.


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