Entrepreneurs here on X are sharing when VCs have treated them badly.
Every time I read one, I feel bad because I know I've treated some entrepeneurs badly too. Even though I've treated thousands well, it is those few I treated badly that weighs heavily in my mind.
Today I try to treat everyone well, but still fail once in a while.
Treating people well leads to much more happiness than treating people badly.
Here's a list of everyone's stories my AI was able to find:
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Here's the full list of entrepreneurs sharing VC rejection stories, starting with the freshest from today and working backward:
Matthew Prince (@eastdakota, CEO Cloudflare)
Two stories: A Sequoia partner passed on Cloudflare because "he didn't think a woman could lead a security infrastructure company." Plus: got intro to Marc Andreessen, the meeting was scheduled for a Monday ("which should have been a clue").
Sarah Drinkwater (@sarahdrinkwater, investor/founder)
LP insisted on meeting at Hurlingham Club (ritzy tennis club, 90 mins outside London). He was late. Asked on video from his car why her dad or husband hadn't done 100% of the seed himself like his dad did. Sent a pass email "so rude I pinned it above my desk as fuel."
Ansh (@anshublog, Scrut)
"One VC got increasingly angry with me as the pitch went on, started shouting and his face got red." Very upset that anyone would think enterprises would trust a startup with sensitive cloud data. "Now we have Walmart & Visa."
Romain Lacombe (@rlacombe, co-founder Plume)
Two stories in one thread: A "Sand Hill legend" stood up in the middle of his pitch, turned to him as he left, and said "you're brave" — probably not a compliment. Plus: a French VC who told him point-blank [it was futile].
Aaron Boodman (@aboodman)
2014 at Khosla Ventures: the partner assigned to them flaked with no notice. They got reassigned to someone with zero context. He "arrived, openly irritated," sneered "well, I guess you've got me," then disappeared into his email for the entire pitch.
Mat Sherman (@MatSherman)
"Thank god YC rejected me 11 times so I would have the fire in my belly long enough to stumble upon our current model."
Liz Wessel (@lizwessel, co-founder WayUp)
2015 Series A: "One partner (famous Midas lister) fell asleep. Another couldn't stop scowling." Got a call 2 hours after the IC: they were sending a term sheet. "And somehow they later acted shocked when we didn't take it."
@panickssery
On Anthropic's Series B: "Their crime? Passing on the Series B, the hardest round Dario ever had to raise (led by Spark). In venture, conviction is all that counts."
@hthieblot
"I flew 4 hours for a Series A pitch. The VC opens the door: 'I've got 20 minutes.' Skims the deck. Says: 'We don't invest in media companies. Don't want to waste your time.' I stayed calm, thanked him, and walked out."
Harry Stebbings (@HarryStebbings, 20VC)
"I introduced Dario [Amodei] to 22 friends up and down Sand Hill Road and we got 21 no's… it was such a brutal time getting this company going." That company today trades at $860B on secondary markets.
Daniel Dhawan (@danieldhawan) — 13 likes
YC rejected him 8+ times from 2019–2024. Then raised from a16z @speedrun in 2025.
Tobi Lutke (@tobi, CEO Shopify) — reshared Startup Archive
VCs on Sand Hill Road passed on Shopify ("market wasn't going to be big enough"). That's among the worst misses in VC history.
