Three of our worst VC stories
twitter.comhttps://xcancel.com/eastdakota/status/2062860530360959273
More of these (via https://news.ycombinator.com/item?id=48418641 below):
https://xcancel.com/gregisenberg/status/2061794787825479818 (<-- the OP)
https://xcancel.com/dunkhippo33/status/2062768969560510486
https://xcancel.com/typesfast/status/2062791307094048937
https://xcancel.com/awxjack/status/2062605286683336757
I started a new company with my cofounder 6 months ago. We focused on what people wanted, built a manual solution then automated it. We have 60% margins and a system ready to scale. We are thinking of avoiding investments. I am not sure if we are in a new moment in time where investments are something people do because of what used to be the best to do. And I am not saying avoid blitzscaling but do it without external capital. The hypothesis is that a small team, Claude Code subscriptions, apis and automation/code are enough to make it work via profit reinvested from sales. And it will be actually a competitive advantage because of removed costs, mostly from coordinating a lot of humans and having outside forces pulling in different directions.
Buy a few GPUs so you can skip the Claude subscription, and never have to worry about rate limits, privacy, or refusals. Will pay for itself with a small team in a few months.
I mostly work on custom from scratch Linux operating systems and packages across dozens of languages.
I do 100% of my AI work today using two AMD r9700 pro GPUs on a 10yo pc I pulled out of an old arcade machine.
AI subscriptions only make sense for people who cannot build a basic home computer.
How long has this been your daily driver? How has this setup worked for you compared to enterprise models? Which models?
Maybe 2 months. I have mostly used the Qwen series, and currently running Qwen3.6 27B for programming and debugging and Qwen3.6 35B for speed and research. Both punch way way above their weight and replaced Qwen3.5 122B for me. Qwen 3.6 27B even is, for my workloads, preferable over Big Pickle (GLM-4.6) which is the only large third party model I have used extensively for reference and comparison as it is free and requires no signup or PII via OpenCode. My go to agent solution though is Charm Crush.
I once had a VC ask to meet my founders and I for his morning breakfast at a run down diner in texas. So we fly out from Florida pitch deck in hand, and meet him at his booth.
We pull out the deck, he says "Do not need that. How many paying customers do you have?"
Given we were at MVP stage and were running a public sentiment analysis driven social media search engine using our published academic AI work (15 years ago) we said "None yet. The capital to build the paid portion of our product, which is popular, is why we are here."
As he eats his eggs he goes "Come back when you have a hundred or more paying customers" and sent us packing .
Not even a 5 minute interaction with people he asked to fly out to pitch him, and were not even allowed to pitch.
I expect rejection by default at an early stage, but that one was particularly mean.
It will forever remain my go to example of a meeting that could have been an email.
One excited investor we did find for another project ended up being the now famous con man "Michael Prozer" who got on who wants to marry a millionaire using forged bank records and proceeded to get actual capital based on this lie until he was arrested for fraud.
My opinion of VCs is still... recovering. The bar is in hell.
At what point does this kind of groveling behavior actually become a negative signal, though?
If you’re willing to fly halfway across the country just to talk to a VC in a diner, it signals a lot of desperation IMO.
I haven’t had a ton of interactions with VCs; however, I have read innumerable books about the VC world, and a recurring theme is that VCs are competitive and don’t like being left out of a deal / losing a deal to another VC.
By willing to fly so far away for nothing, it signals that no other VC is interested.
So, how long did it take you to go 100 customers after this pitch?
In the end my co-founders and investors wanted to sell to a single specific political party exclusively. I chose not to participate as it did not align with my goals, and started a small IT company instead. The original project was dead within a couple months of me leaving given no one else had any idea what ssh was.
#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
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?
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.
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
there is a saying about mixing business with pleasure
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/
If they truly are useless that's one thing, but the ability to "impress" some asshole in a 30 minute pitch has little to do with running a successful tech company.
With what authority are VCs claiming to be capable of being an accurate judge of talent or character in less than an hour?
Sounds like said VC in your example is doing insufficient due diligence and just investing based on vibes.
something pattern something matching something
They have superior taste of course.
>> the ability to "impress" some asshole in a 30 minute pitch has little to do with running a successful tech company.
Judging by the stories being shared here, that is all it takes to get funded...
Sure but the act of actually securing VC funding is a small part of running a company. Those VCs are not going to recoup their investments if they pick people who optimize for funding and not for product vision and good leadership.
I suppose one could argue that VCs develop a taste for it after speaking with so many founders.
But, of course, you often don’t find out what lay down the road not travelled, except for those companies that get funded elsewhere, so it’s not like there’s an obvious objective measure.
I can’t help wondering if it’s a bit like Moneyball though and, if you had good enough data that you could model it well enough, you’d discover a lot of that taste is just shooting bull and doesn’t amount to much. Possibly there’d be a lot of variability across VCs.
omfg that’s the beach access guy
ugh. That douchebag doesn't even surf.
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.
I had the same thing happen (though seed round). I don't think it's uncommon. Also never took another meeting with the guy.
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.
Nah, he was talking about taking their stock. That’s morally theft even if by some convoluted reason it’s not legally theft.
I get the business as usual analogy but the specifics of the interaction are different. You just showing up to your club with your friends is different than having equity in a company you cofounded.
Vinod is insane. You can hear more of his really bad takes on his recent Sam Harris podcast episode: https://www.samharris.org/podcasts/making-sense-episodes/479...
All I ever hear are horror stories. Can someone tell me a good story about VC that isn't Facebook or something?
There are tons and tons of mundane VC stories. They all mostly just go "we came, we presented, we were funded"
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...
+1 to Casey Aylward being a class act. Super useful and seems to have the magic touch for dev tooling investments.
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.
This is awesome!
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.
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.
Great story! What was the stock plan mess up that resulted in that?
Could you ask the VC if you could name them in the story?
It's unfortunate that some VCs I respected turned out to repeatedly have their reputation tarnished by such negative stories. I'm not sure what compels founders and VCs to be polarizing and not diplomatic like the old days.
This is one for https://news.ycombinator.com/highlights!
(I mention this so more people can know the list exists, and hopefully email hn@ycombinator.com when they see comments we should add.)
What's the best highlight you've seen?
I have no memory for that sort of thing. I can't tell you the best movie I've seen or the best record I've heard or anything of that kind. Sorry!
I do think it would be fun to have an "i feel lucky"-style random selection of highlights.
I did want to have a random link of a similar nature, hopefully that is interesting enough for HN! I made something similar via a browser HN link, very enlightening.
I wonder how the LPs in the fund felt when they heard they lost out on this?
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.
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.
I mean the goal is that the money invested increases the value of the company so that the founder's reduced stake is worth considerably more than the founder's full stake of the counterfactual company where he didn't take VC money. VCs can be strongly positive sum.
i raised twice from USV. class acts all around. too many stories to count, but they always had my back.
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.
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.
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.
It’s a very fine line between being helpful and a jerk. Same story to someone else may have ended up as a bad Twitter story.
You might want to listen to the Ron Conway episodes of the https://www.thesocialradars.com/ podcast.
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
That's a remarkably well-called shot, honestly, damn, wish I thought of that!
And yet Akamai is profitable… whereas Cloudflare is not…
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.
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.
Really sad that people are still walking around with those beliefs.
The fact that you hear this often (also not only from the victims of this) should signal that, even without quotes, there is likely some truth to it.
This doesn’t follow logically.
Someone asked him this down the thread. He replied that it was said to him. So it’s a first party account.
It's interesting he provides quotes for the other stories, but not this one. And still doesn't in the thread. Again, i'm not debating the authenticity, but is it possible he's inferring that based on something not-so-explicit being said?
I'd love to see/hear the words that people actually say when I hear stories like "they said they wouldn't [invest/buy/etc] from me because i'm a woman".
I came across this thread on twitter this morning but isn't he the CEO / co-founder and he's clearly a man? I guess I don't get the reference. I know he has a co-founder who's a female, maybe she was lead at the time?
"1. A Sequoia partner passed on Cloudflare because he didn’t think a woman could lead a security infrastructure company. Seriously. "
He's referring to Michelle Zatlyn afaict.
"Young Global Leader '14. Co-founder, President + COO Cloudflare"
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.
VCs are the shotgun cartridge and startups are the shot.
It used to be that VCs wanted founders to pursue a singleton strategy, because they wanted the diversification to occur at the level of their portfolio - on the grounds that at the level of an individual startup, diversification would less likely to succeed. The catchphrase was that they wanted "pure play" investments. So it would be interesting to know why it's now a cause of friction. (The "pure play" thing was actually from before YC took off and gave founders a bit more agency; and before the "pivot" was popularised; I get the impression that VCs back then were not too happy for a founder to change direction and confuse their portfolio)
After reading some of these stories, I don't see how you can't come away thinking that psychopathy is a trait that goes hand in hand with being a successful VC. The story about Vinod Khosla speaks for itself, but after reading #2 I clicked on Marc Andreesen's twitter profile, which currently says this:
> You’re not talking to someone who woke up a loser. That loser attitude, that loser premise makes no sense to me.
These fuckers are grotesque caricatures in human skin.
If you're not aware that's actually a quote from Jensen Huang.
This quote is from a viral interview between Jensen Huang and Dwarkesh Patel, the latter made some points during the interview that were very condescending and betrayed a deep misunderstanding of technology.
theres always a story behind the story. wondering why he chose today to say these
probably just been long enough that he doesn't give a shit
source: most of the bullshit i surface up nowadays
i mean right but even you hold back some stuff because youre a Nice Person yknow? haha
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.
Greg Isenberg's viral tweet about VC that fell asleep during a pitch kicked off a bunch of other tweets about weird VC experiences this week:
https://x.com/gregisenberg/status/2061794787825479818
Some QTs:
https://x.com/dunkhippo33/status/2062768969560510486
https://x.com/typesfast/status/2062791307094048937
https://x.com/awxjack/status/2062605286683336757
https://x.com/travisk/status/2062224472426365045
https://x.com/mark_cummins/status/2062293061426663612
Oh thanks! I'll add these to the toptext.
Can you please fix the URL? HN policy is to link to the canonical site rather than an archive service, which I’m sure you are aware of. Thanks!
Which URL?
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?
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
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?
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.
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.
East Dakota is Western Minnesota. This is MAGA country
He's a very MAGA guy, though.
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.
Tell us one or two, then!
The (fun?) one that stands out the most were the Pittsburgh Angels (2013 probably) and they literally have a long round table that they dine at in a closed off room in this country club. They take like one or two pitches a month and tell you that they generally do 300-500k checks.
I was invited and drove 3 hours. They then put you in a giant dining room with all the country club members eating dinner, with your own table by yourself. They tell you to order whatever you want, and wait there, and when the group is ready you'll be summoned to dance.
Anyway, whenever they are ready which was like an hour and a half, they call you in and you have to be ready.
While they loudly eat dessert you are supposed to walk around this 20' long table pitching them whatever you're doing and then you have to take questions from them, while still walking around a table. No presentation place, no place to sit, no real way to talk with everyone, you're always talking over someone's head.
Then they say thank you and on the way out you get a bill for whatever you ate.
That was one of the "nice" ones. There's tons of bullshit networks like TiE, Keiretsu forum, YoungPresidentsOrganization shit like that are all social clubs for wannabe oligarchs.
I think every Chinese backed firm on sand hill road at the time was a front for Chinese billionaires money laundering, I'm sure I have the giant spreadsheet of funds I talked to from 2016 that later turned out to be almost exactly that like Rothenberg Ventures.
The bad ones are LP's sexually assaulting people and being told to ignore it or that it's no big deal (I didn't ignore it and people got fired). Or when LPs push CEOs to fire more people than they need to, or to raise money through some shady vehicle to get it off the books. Not to mention seeing too many people that later were in the Panama/Epstein files.
Literally horrific
They tell you to order whatever you want, then surprise you with a bill at the end?
I was also baffled
>some of the wild stuff I’ve either been asked to do
Oh man, I'm really sorry you had to go through that :'(.
Yeah same, but eye opening no less
Did the author edit the tweet/post or am I crazy? There are only two stories
For some reason they're not threaded on the twitter link, but you can see them threaded on the xcancel link:
https://xcancel.com/eastdakota/status/2062860530360959273
The third is in a reply. Use the XCancel link to view it without logging in.
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.
>> More and more I see why bootstrapping is the way to go.
That does not match the definition of success here...the trick is to become a billionaire and call yourself an entrepreneur without ever turning a profit.... :-)
Then keep getting acquired, become a VC, do the same on and on.
Clouflare is an example as a loss making company, every single Musk company with the exception of his state subsided Tesla, Epic Games, Snap, DoorDash, WeWork, Rivian, Lucid, Peloton, Roblox, Wayfair, Lyft, Reddit, ...
Being a real business, and turning a profit, is very, very hard, you have Google, Amazon and a infinitesimal few...
Seems people downvoting don't understand your sardonicism lol
This. Here is my bootstrapped niche corner of the internet: https://www.sourcemeta.com
Nice, how's the revenue/profit? Seems hard to monetize.
Link for non x users:
https://xcancel.com/eastdakota/status/2062860530360959273
what is the "meeting scheduled on Monday clue"?
partner meeting
Next up, one of our worst CEO stories
There was once a CEO who built a great company, then decided to fire 20 % of the company and call those people publicly "measurers", so they are basically tainted in the marketplace. Oh wait...that was eastdakota
A CEO got entire 20 man dev team into boardroom and asked everyone to voice any concerns about technical debt, bad development practices, anti patterns as well as project management issues.
The 4 people who spoke up were all fired on the same day 3 or 4 weeks later. 7 more quit shortly after - as soon as they got any decent offer. 6 months later about a quarter of the 20 were still with the company.
HN policy is to link to the site. If someone wants to use an archive service they’ll use it, meanwhile most of us want to be able to reply, follow, read etc.
As bad as these VCs seem to be it's something to see Prince socializing with other bad actors like Maguire while lamenting the bad actors in the space.
What's bad about Maguire?
On one hand, every VC who passed on Cloudflare missed out on what is now an $88 billion company. On the other, if they didn't invest because they didn't like the underlying economics, they were actually correct. 17 years after founding, Cloudflare still has never turned a profit.