Three of our worst VC stories

111 pointsposted 3 hours ago
by orgonon

51 Comments

cowthulhu

2 hours ago

#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?

cryzinger

an hour ago

I think a lot of people fail to recognize that they're the next target, or convince themselves they're special in some way that makes them immune. It's like when someone knowingly participates in an affair and tells themselves "Sure, they're cheating on their current partner to be with me, but after they break things off I know we'll be together forever!"

CPLX

15 minutes ago

Some people really do thrive on this shit though. They know the rules of the game and want to play it. What they’re really thinking is they’ll be better at the game than their opponents.

I mean can you actually imagine the internal monologue of a guy like Sam Altman?

raverbashing

41 minutes ago

Yup, exactly this

For example, if you go off with the cheating partner, don't expect it to not happen again

wheels

15 minutes ago

I had the same thing happen (though seed round). I don't think it's uncommon. Also never took another meeting with the guy.

toxic

an hour ago

Because if you get involved with most VCs, you will then have to watch your back until the end of time.

None of those "worst experiences" seem all that unusual to me (though nobody will say #1 out loud anymore until after they've invested), and #3 is completely in character for Vinod.

root-parent

a few seconds ago

If one partner is the core of the company, and the others the VC thinks are useless ( I am not saying in this case they were...just that the VC might have that perception) what should the VC do?

After all its just business decisions like Cloudflare recent layoffs no?

https://blog.cloudflare.com/building-for-the-future/

sunjieming

41 minutes ago

Yeah, this is par for the course with VC. You should never believe your VC (even post funding) is your friend. They can be a great business partner and resource but they're never your friend under that dynamic

darth_avocado

an hour ago

Because rich and powerful people also have massive egos to go with their power and money. Some of them will find your rejection a personal attack and try to actively sabotage you. Not all VCs are like that, but there are enough of them that you need to be careful about how you handle the situation.

tehwebguy

an hour ago

omfg that’s the beach access guy

foobarbecue

20 minutes ago

ugh. That douchebag doesn't even surf.

wslh

27 minutes ago

Sadly, I've experienced this myself, and I'm aware of other people who were cut off from opportunities in similar ways. I applaud the tweet because this is important to say out loud: we are often not living in the world we think we are observing. Many people know this, but few talk about it. It's an open secret.

TrackerFF

11 minutes ago

My pet theory is that it is more nurture than nature. These (VC) veterans have seen thousands of startups come and go, and become so desensitized to the ruthlessness.

Of course to people like the author, it seems borderline sociopathic to casually suggest such levels of betrayal. It is like trying to get into the most exclusive nightclubs, and when you're finally in the front, the bouncer will look at the group and say "You can get in, but not those two". It sucks, but to the bouncer it is just business as usual, and you're just another face.

tty456

6 minutes ago

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.

jphil529

4 minutes ago

Really sad that people are still walking around with those beliefs.

satvikpendem

13 minutes ago

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.

stevepotter

2 hours ago

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

mitchellh

an hour ago

As with all things, the horror stories just get the most attention. People love to rage. There are plenty of boring (good, even!) VCs out there. They just work more quietly, professionally.

I'll share a story, but its about a close friend and not me so I won't name any explicit actors and I'm going to round out the numbers. You either trust me or you don't, but this is a very direct relationship I have to both the founder and VC.

The story is this: the founder started their company outside of SV, so the lawyers weren't super familiar with startups and messed up the initial incorporation and stock plan stuff (actually super common: use Stripe Atlas or pay a startup-aware lawyer!). Went under the radar through years. This company ended up being bought for nearly $1B (with a B) after many rounds and a large board.

During the legal work to close the acquisition, they found out this messed up stock plan. Without going into the details, the effect was that instead of taking home $200M, the founder would take home ~$75M. The mistake the lawyer made almost a decade earlier was about to cost him $125M.

Most of the board basically said "too bad so sad, law is law." But one VC (the one I know, the one I'm talking about) basically strong armed and politicked the whole thing and eventually convinced everyone around the table to give up an equal share of their own holdings to make the founder whole.

Letter to the law: they didn't have to.

Spirit of being founder friendly: this VC went to bat hard and got everyone to yield to make things "right."

Also, look, you might argue $75M vs $200M is just "rich vs rich." Who cares? Sure. That's not the point.

You don't hear about stuff like this because honestly its not a big enough deal and feel good stories get way less clicks than pitchfork stories.

ChrisMarshallNY

28 minutes ago

Thanks for that story.

I feel as if basic Personal Integrity is now considered an anachronistic weakness, in the tech industry, and it's heartbreaking. I know that VCs can probably share similar stories [to the OP] about some of the people that pitched them, or their behavior, after getting funded.

Lotta ass, being shown, all around.

At some point in the future, I may consider smaller-scale (local) angel investing, but it seems like such an ugly field, not sure if I'll ever do it. I don't need the money; I would do it to help folks get a leg up.

thadt

39 minutes ago

Right - and if I ever go to raise VC then that's a guy I'll want to talk to. Even if they themselves don't invest, their recommendation would be valuable.

Life's too short to screw people over - reputation is one of the few things that last after we're gone.

wenbin

an hour ago

This is awesome!

Aurornis

an hour ago

The non-horror stories are usually pretty boring: VC heard the pitch, then either passed politely or wanted to be part of the round. If they joined, they wrote a check and wanted updates.

The VC landscape has changed a lot since some of these stories happened. Many years ago, there were few VCs and even good companies had a hard time getting funding. This created weird environments with some VCs raised funds and then liked having companies crawl to them to beg for the money.

There are still some VCs like that, but there has been an explosion of VC funds and money. Most VCs know they need to work hard to earn the trust of founders that they want to invest in. Leaving a bad impression could mean you're left out of the next round if you want it.

This goes against the popular idea of VCs, but most VCs I've worked with are actually pretty boring, normal, nice people.

jwatzman

26 minutes ago

My prospective co-founders and I were pitching to a VC firm that was, on paper, a really good fit for what we were trying to do. The partner we were pitching to was, 15 years ago, briefly my manager's manager -- some work relationship there, she remembered me and I her, but we didn't work super closely together and it had been a very long time. She had moved on at that company to more big-shot things and ultimately become a partner at a respectable VC firm.

About 10 minutes into the pitch, she cut us off, and basically said -- as absolutely kindly as something like this can be directly said -- "I am not going to invest in this, and furthermore I don't think what you're trying to do is investible at all". Then she took a bunch of her time to run us through why, help us understand some very fundamental things about the VC world we didn't quite have right, and generally be brutal but extremely useful in us framing what we were trying to do.

She didn't have to do that. She could have nodded along and then given us a polite "no" like everyone else. She could have cut us off and given us a rude "no". But she didn't -- she made sure to use the time we had to help us as much as she could, even if she very adamantly was not going to invest.

Not a big gesture or anything, but kind and helpful. There's a lot of that. But it doesn't make headlines.

sskates

an hour ago

I believe Eric Vishria is the best Series A board member of this generation. I've learned more from him about it what it means to be a great CEO over the last 10 years than anyone else. I haven't heard of another founder who has spoken as highly as their Series A investor.

I've been meaning to write up my story with him. Now is a great time with all the horror stories on others that have been coming out.

He sticks through his companies for over a decade, which is rare in this business: https://x.com/ericvishria/status/2051459386372149506

margalabargala

2 hours ago

There are tons and tons of mundane VC stories. They all mostly just go "we came, we presented, we were funded"

troyvit

40 minutes ago

Tony Conrad [1] was the VC that guided our related content engine (Sphere: a vector database before vector databases were cool) through a $25 million exit. Chump change these days but he took really good care of us, leading us through a global recession and then two acquisitions.

[1] https://about.me/tonyconrad

maccard

39 minutes ago

I was just an engineer at a vc backed startup but our interactions with the VCs were totally normal - they were no better or worse than when we worked with publishers or other external funding sources.

trumpdong

an hour ago

The best possible case is that you get a cash infusion now in exchange for giving up a huge percentage of your future revenue and control of the company.

joshu

an hour ago

i raised twice from USV. class acts all around. too many stories to count, but they always had my back.

cyberax

27 minutes ago

Sure. They are usually just very boring: you made a pitch, got funded. The VCs used their connections to get you good advisors and/or introduce you to prospective clients.

swyx

2 hours ago

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

fastball

an hour ago

Well he did retweet another tweet that kickstarted the convo, very possible he saw that tweet, said to himself "I have some of these to share!" and then proceeded to... do so.

mitchellh

an hour ago

probably just been long enough that he doesn't give a shit

source: most of the bullshit i surface up nowadays

giancarlostoro

an hour ago

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.

snowwrestler

7 minutes ago

Cloudflare is fantastic at marketing, and pretty good at technology. I evaluated them twice for enterprise contracts and both times picked a competitor. The first time, it was DosArrest for DDOS protection, which was a much better value per dollar (but they sucked at marketing.) The second time, we needed a CDN with particular features and Fastly was a better fit.

My point is that it’s very very hard to know in advance that a startup is going to be awesome at marketing. Their tech was not, on its own, a giant moat or a “must have” standout. So I can see why some VCs shrugged.

jaggederest

an hour ago

And as someone who briefly had to interact with Akamai, the deficiencies in their product are not even close to subtle.

raverbashing

38 minutes ago

Sounds like how WeWork ate Regus's lunch even while being made of crazy

Quarrelsome

an hour ago

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?

boelboel

an hour ago

Getting extreme wealth is more so about luck in various forms than competence/intelligence. If it were just about the latter everyone who's intelligent/competent would be rich. You don't hear about boring wealthy people either.

rwmj

an hour ago

Why do you think people who lucked into vast riches by being in the right place at the right time would be especially smarter than anyone else?

itkovian_

13 minutes ago

In many cases the GPs are not, at least nowhere near as much as you’d think. Obviously there are power laws here as well. Non partners, forget about it.

The other thing is it is maybe the most nepotistic industry out there. Which somewhat makes sense given the actual job is so relationship based.

wahnfrieden

an hour ago

Competence, intelligence, merit have little connection to wealth. Wealth at that level is attained through arguably unfair means, not from reward for hard work. Conversely, poor people are not poor as punishment for lack of intelligence or merit

AndrewKemendo

an hour ago

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.

mi_lk

an hour ago

what is the "meeting scheduled on Monday clue"?

joshu

an hour ago

partner meeting

camel_gopher

an hour ago

Next up, one of our worst CEO stories