Three of our worst VC stories

#3 is insane, if for no other reason than the VC is signaling that he’s likely going to try and do the same thing to you some day… even if you were totally willing to screw over your team, why would you ever get involved with that VC given you’ll then have to watch your back until the end of time?

I hear story #1 periodically, but almost never see a quote. How is this stuff said specifically? It always seems like hearsay. I'm sure it's authentic, but I'd love to hear the details on how that stuff is actually said in conversation.

More and more I see why bootstrapping is the way to go. And especially in this SaaSpocalypse with AI companies commoditizing entire companies with new feature releases like Claude Design or Codex for legal, it's better to just run your little corner of the Internet and make sustainable money over hyperscaling with millions and billions and being put out of business the next week.

One might say why bootstrappers won't get erased too but they can carve out a specific market too small for AI companies to want to touch, and still remain sustainable rather than needing to make a ton of money; and pivoting as a venture backed company can be much harder as there are more people to please like investors and your employees which you likely have more of than a bootstrapper.

All I ever hear are horror stories. Can someone tell me a good story about VC that isn't Facebook or something?

I doubt VCs have different distribution of personal character from other professional groups.

In my experience, a more interesting friction is that VCs are pursuing a diversification strategy while founders are pursing a singleton strategy.

theres always a story behind the story. wondering why he chose today to say these

Did the author edit the tweet/post or am I crazy? There are only two stories

The first I heard of Cloudflare was a recommendation from someone who used to DDoS websites (and yes they've been arrested for related crimes, long story), and I thought "what the heck is Cloudflare" then over the coming years, I kept seeing other friends using it. It's really interesting that Cloudflare was able to pop into a market that Akamai could have snagged for themselves or outright tried to buy out Cloudflare.

It's a bit crazy in hindsight that companies would have avoided investing, considering this is a space someone like Akamai occupied, and clearly there is value in this space. It's incredible to see how Cloudflare has grown over the years, kind of happy they grew as much as they did, a bit surprised by some of those VC nightmare scenarios.

These VC stories continue to feed my incredulity at how people _that_ incompetent can still be _that_ wealthy.

Is it the money that makes them stupid or smth?

I could write a book with the horror stories I have of VC and LP behavior, and some of the wild stuff I’ve either been asked to do, verified others were asked to do or say it’s just totally unhinged.

I don’t know if Angel investing groups are really still around like they were in there 2010s but the variance in the types of insanity and weirdness for those groups is really unmatched.

what is the "meeting scheduled on Monday clue"?

Next up, one of our worst CEO stories