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Reflecting on My Failure to Build a Billion-Dollar Company (sahillavingia.com)
3 points by karagenit on July 16, 2022 | hide | past | favorite | 2 comments



(2019) Gumroad bought shares back from their VCs for $1!

Meta: I suspect this article would have had comments from HN founder-types in the past, back when HN had more focus on startups. Perhaps HN is no longer so focused on startups any more?

Amazing section from article:

  I got this email from KPCB, our lead investor: “KP would like to sell our ownership back to Gumroad for $1.”

  Mike had left KPCB to start a new company, and KPCB didn’t want the operational headache of appointing a new board member. Plus, it helped their taxes. In one fell swoop, our liquidation preferences (how much we would have to sell for before dollars started going to employees) went from about $16.5M to $2.5M. All of a sudden, there was a light at the end of the tunnel.


I found this to be much more interesting read than I originally expected from the tone of the title.

Spoiler alert: Especially interesting is the eventual realisation that they were limited by market growth that wasn’t compatible with VC investment expectations, but that when no longer burdened by that (see robocat’s comment) the company was able to continue growing at a more realistic pace.




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