#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 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!"
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.
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.
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
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Casey Aylward from Accel has been mentioned in all void0 company posts. So she must have been very useful for the founder. (I don't have any insider information about void0, I've met her a few times and she is amazing)
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.
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.
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.
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.
https://en.wikipedia.org/wiki/Affinity_fraud among other factors - being someone who talks right and plays metaphorical ball with the correct people matters more than any amount of intelligence or competence.
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
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.
#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 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!"
Yup, exactly this
For example, if you go off with the cheating partner, don't expect it to not happen again
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.
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.
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
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.
omfg that’s the beach access guy
All I ever hear are horror stories. Can someone tell me a good story about VC that isn't Facebook or something?
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.
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.
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.
This is awesome!
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.
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.
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
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
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.
There are tons and tons of mundane VC stories. They all mostly just go "we came, we presented, we were funded"
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.
Casey Aylward from Accel has been mentioned in all void0 company posts. So she must have been very useful for the founder. (I don't have any insider information about void0, I've met her a few times and she is amazing)
https://voidzero.dev/posts/voidzero-cloudflare#acknowledgeme...
i raised twice from USV. class acts all around. too many stories to count, but they always had my back.
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.
theres always a story behind the story. wondering why he chose today to say these
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.
probably just been long enough that he doesn't give a shit
source: most of the bullshit i surface up nowadays
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.
And as someone who briefly had to interact with Akamai, the deficiencies in their product are not even close to subtle.
Sounds like how WeWork ate Regus's lunch even while being made of crazy
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?
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.
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?
https://en.wikipedia.org/wiki/Affinity_fraud among other factors - being someone who talks right and plays metaphorical ball with the correct people matters more than any amount of intelligence or competence.
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
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"?
partner meeting
Next up, one of our worst CEO stories