THE COMPANY-BUILDING FIELD NOTEBOOKRESEARCH EDITION / SEPTEMBER 2026
Startup
Research.
Search
POST-MORTEM LIBRARY / Mid-size venture-backed failures ($20M–$200M raised)

Shyp

  • Company — Shyp
  • Sector — Logistics / on-demand shipping
  • Founded / Died — 2013 / March 2018
  • Lifespan — ~5 years
  • Capital raised — ~$62M (Kleiner Perkins, Homebrew, Slow Ventures); peak valuation ~$250M
  • Peak scale — Four metros; headcount peaked around 300. Revenue never disclosed.
  • What it built — An app where you photographed an item, a courier collected it within 20 minutes, and Shyp packed and shipped it for a flat $5 fee plus postage.
  • Stated cause of death — CEO Kevin Gibbon's shutdown post and subsequent essays are direct: the company scaled to new cities before the unit economics worked, and "I let the fear of missing out drive our decisions." He has written explicitly that the flat $5 fee did not cover the labour it purchased (Gibbon's essays; Fast Company).
  • Evidenced causeStated and evidenced causes agree closely, which makes this post-mortem unusually valuable. Reporting corroborates: consumer shipping is low-frequency (most people ship a few times a year), so acquisition cost could never be amortised; the 2017 pivot to small-business shipping was correct but came two years and roughly $40M too late.
  • Warning signs visible earlier — Consumer shipping frequency was knowable from public data before launch. The four-city expansion in 2015 preceded any demonstrated positive contribution margin.
  • Money outcome — Investors lost ~$62M. Employees laid off; Gibbon gave interviews taking personal responsibility. He later founded another logistics venture.
  • Post-mortem qualityHigh. Gibbon has spoken and written repeatedly, including under the unflattering framing "from $250 million to 0." Minimal self-service; he names his own FOMO as a cause.
  • Transferable lesson — Purchase frequency is a hard constraint on consumer CAC payback. If the average customer uses you three times a year, your acquisition cost must be recoverable over years, and almost no venture-funded growth plan can wait that long.
  • SourcesFast Company · Airhouse interview, "How I Failed" · Failory

Read the wider evidence

This entry is reproduced from the supplied research, with its inline source links retained. It has not been independently re-reported for this website conversion.

Read the complete chapter, source list, and methodological notes →
← Back to post-mortems