Travis Kalanick, Mark Pincus, and other founders share their horror stories of pitching to VCs; Cloudflare CEO Matthew Prince publicly calls out Vinod Khosla
Asking venture capitalists for investment is a rite of passage for tech founders. This has led to another universal experience: the VC pitching horror story.
TechCrunch Julie Bort
Context & Ripple Effects
The related coverage records earlier strain in the founder–investor relationship: during the SVB crisis, founders and investors described smaller firms and solo investors as more responsive than many large VC firms. Earlier funding-squeeze coverage also showed investors seeking more protective financing terms.
The latest public accounts extend that pattern from transaction terms and crisis support to the pitching process itself. Matthew Prince’s decision to name Vinod Khosla makes the criticism unusually visible because it comes from an established operating executive rather than an anonymous founder.
First-order effects
- The founders and investors named in the accounts face an immediate reputational contest: founders can validate one another’s experiences publicly, while the targeted VC and the broader investor class face pressure to explain or rebut their conduct.
- Pitching founders gain more public reference points for evaluating investor behavior, beyond valuation and check size.
Second-order effects
- VC firms may put greater weight on partner-level reputation and founder references, since poor pitch-process behavior can become a recruiting and deal-sourcing liability.
- Smaller funds and solo investors that were portrayed as more helpful during the SVB episode can use responsiveness and founder treatment as differentiation against larger, more established firms.
Third-order effects
- If prominent founders continue to air these experiences, access to high-quality startup deal flow may depend more visibly on an investor’s operating reputation, not just brand, capital, or portfolio.
- The pattern points to a less opaque venture market in which founders increasingly assess investors as long-term counterparties; whether that meaningfully changes financing power will depend on how scarce capital remains.
The trend: This is one data point in a broader shift toward founders publicly scrutinizing VC behavior, from financing terms and crisis support to the interpersonal mechanics of raising capital.
Related: Cloudflare · Vinod Khosla · Around 20 investors and founders detail how some solo investors and sm · Inside VC funding squeeze: DraftKings raises $100M through convertible
Related Coverage
- Viral X Thread Reveal Founders' Frustrations With VCs citybiz
- Silicon Valley founders are publicly roasting VCs online. Here are their wildest stories. Business Insider · Lakshmi Varanasi
- ‘Out Cold for 30+ Minutes’: Founders Reveal Their Most Bizarre VC Pitch Meetings Inc.com · Kevin Haynes
- Silicon Valley Founders Are Publicly Naming the VCs Who Burned Them Implicator.ai · Marcus Schuler
- Cloudflare CEO says Vinod Khosla urged him to oust his cofounders during funding talks The Economic Times
- Friday Media Lunch Series With Inc. and PAN Meredith & The Media · Meredith Klein
Discussion
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@eastdakota
Matthew Prince
on x
Two of our worst VC stories: 1. A Sequoia partner passed on Cloudflare because he didn't think a woman could lead a security infrastructure company. Seriously. 🙄 2. I got introduced to @pmarca. Meeting got scheduled for a Monday, which should have been a clue. I thought it was
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@markpinc
Mark Pincus
on x
In 2007 i pitched an enterprise vc firm on Zynga (bc no firm wanted to back us) and the partner fell asleep. I looked at my friend who set up the meeting and asked if i should keep presenting and she said yes. It was ‘weekend at bernies’ meets Silicon Valley.
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@travisk
Travis Kalanick
on x
In 2001 I intercepted a partner at a VC who was trying to escape his office before our meeting was supposed to start. I ended up pitching him in his parked Lexus from the passenger seat. At one point he grabbed my laptop placed on his large belly which was pressed against the
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@gregisenberg
Greg Isenberg
on x
I was once pitching in a board room at a top 3 VC firm for a $15M Series A. 12 people in the meeting. One of the GPs fully fell asleep. Out cold for 30+ minutes. Nobody acknowledged it. Everyone just kept going. I kept presenting my Series A slides to an unconscious man in a
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@zoink
Dylan Field
on x
We pitched for Figma's seed round in 2013. Most folks didn't get it but everyone I met was super nice to me. (It helps to go through warm intros and only meet people that are known to be founder friendly.)
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@pronounced_kyle
Christian Keil
on x
I really dislike this meme. When I started a company 10 years ago, my idea was bad and I was a nobody, but VCs in Silicon Valley still made time to meet with me. A few stories stand out: • @kimmaicutler was the best. Even though she passed, she clearly took me seriously. •
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@mark_cummins
Mark Cummins
on x
Our second round was rough. I think I pitched every VC on the planet. Some of the weirder ones: - I arrive at a Chinese VC firm on Sand Hill Road. The building is locked, lights off, nobody inside. I wait 10 minutes after meeting time. A car pulls up. The partner emerges, she
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@rick_zullo
Rick Zullo
on x
If it makes you feel better, a LP we pitched in Fund 1 asked to meet at Monday 7am when my daughter was born 2 days before They showed up 45 minutes late and ate a breakfast burrito during the pitch before telling me that they weren't looking to add anything new to their book
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@eastdakota
Matthew Prince
on x
One more I forgot until just reminded: 3. Khosla Ventures wanted to invest in our Series C. Vinod took me, Michelle, and Lee out to dinner after he'd given us a term sheet. Near the end, Michelle and Lee got up to use the restroom. Vinod leaned over and said: “I'm impressed with
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@eastdakota
Matthew Prince
on x
@HassanRIsmail He's extremely smart/clever. Has been an incredible investor — can't argue with his track record. Just not the personality I'd choose to work with.
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@mattmireles
Matt Mireles
on x
I had 45 days of cash, a broken cap table, a new viral product, and a co-founder with cancer. The cancer was a secret. We needed to keep the company alive to fund the surgery (with health insurance). @Alfred_Lin got on a call with me from a taxi in Paris @albertwenger made
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@gregisenberg
Greg Isenberg
on x
Bad news: 99% of VCs don't like me after this tweet Good news: 99% of founders have a similar story to mine (billionaires to early stage) so im not alone The important thing is know what game you're signing up to. Until now these stories have been secrets Do your own research
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@pmarca
Marc Andreessen
on x
On the other hand, we enter every founder conversation hoping desperately they will knock our socks off.
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@awxjack
Jack Zhang
on x
I once flew 30+ hours from Melbourne to London to pitch during the peak of the SoftBank Vision Fund era. I had a 39°C fever. The investor was 90 minutes late. When he finally walked into the room, he was barefoot. No shoes. No socks. Just completely barefoot. I started
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@shaunmmaguire
Shaun Maguire
on x
@eastdakota @pmarca The first story is extremely fucked up I'm sorry to hear this If you can share their name with me that would be helpful
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@mattmickiewicz
Matt Mickiewicz
on x
Felicis Ventures offered to lead our seed round for https://hired.com/ which was doing $200k/mo. Weeks went by without a term sheet or wire transfer. Dec 24th I get a voicemail. They are moving forward but changing valuation from $12m pre to $10m pre. I walked away.
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@matansf
Matan Grinberg
on x
GP at a VC once asked for a customer reference. Customer called me after. GP didn't show up. Junior partner was incredibly rude. Camera off, no introduction, no thank you. We did not take their money. Customer refs can be as much a test of the VC as of the company.
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@mattroberts
Matt Roberts
on x
@gregisenberg I thought you were better then a nap... Here is you pitching my team virtually in 2012. Also you pitching some ladies at a bar in MTL after I dared you to explain the concept to some strangers... [image]
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@bscholl
Blake Scholl
on x
I used to bring airplane desktop models to our investor pitches. A seed investor tipped the airplane back, held it vertically, and asked me why it didn't take off that way. Then he took a call to yell at his wife's dentist during the pitch.
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@fishmanaf
Adam Fishman
on x
Lyft Series C we had the whole @a16z team come to our tiny office in SoMa with one conference room. Middle of the meeting @pmarca stands up during the pitch and walks over to the wall with all the post-it notes stuck on it from a brainstorm. Exceptional power move; not paying any
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@ankurnagpal
Ankur Nagpal
on x
I had an investor commit $5M at the start of the round The day we were supposed to close, he asked to be “downsized” to $100K
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@levelsio
@levelsio
on x
I always keep retelling this story But @travisk was famously kicked out of Uber, the company he founded, by his own VCs You have to be very careful when raising funding money who you're raising from and get a great lawyer that protects yoi Because when you raise money, you
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@aboodman
Aaron Boodman
on x
2014 I pitched at @khoslaventures. The partner that was supposed to see us flaked without notice. We got reassigned to someone with no context. He arrived, openly irritated, and sneers “well, I guess you've got me” then disappears into his email, ignoring the entire pitch. My
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@lizwessel
Liz Wessel
on x
It seems like a large # of the tweets going out about horror VC stories are about the same one investor and yet that investor continues to be wildly successful so I'm really not sure what the lesson to takeaway is here 🤣
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@gkamstra
Greg
on x
There are good stories about Vinod Khosla too, right? [image]
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@alexfmac
Alex Macdonald
on x
Worst VC behaviour I've seen in a portfolio company: A euro VC limited founder salaries to a very low level (<$100k). Founders then received a 9 figure acquisition offer. VC tried to block the deal as was only a 4-5x for them. I and other angels told them in no uncertain
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@dhravyashah
Dhravya Shah
on x
A partner from a tier 1 VC reached out to me on X and we scheduled a meeting. Throughout the first 30 minutes despite all my attempts he kept talking about RAM (hardware memory) I told him i do memory for AI and he still thought its hardware. He kept saying “as you know RAM
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@markpinc
Mark Pincus
on x
Another top growth investor held up the palm pre (which he had backed) and said this is the future and if youre games arent on this we wont be investing. I just stared down at my shoe wondering how such mis guided people are allowed to manage so much money.
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@gergelyorosz
Gergely Orosz
on x
These stories are almost never shared in public, and even when they do, investor names are also almost always never shared. Matthew is torching Sequoia, a16z and Kholsa Ventures here 🔥 - plus a reminder that being passed on doesn't mean it won't work out!
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@pmarca
Marc Andreessen
on x
There are no casual meetings with VC's.
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@shaunmmaguire
Shaun Maguire
on x
There is extreme alpha in backing founders that other VCs underestimate
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@fintech03
Parimal
on x
Khosla is 1 of the very few VCs who will openly look a room full of peers in the eye & insult them. He famously stated during a tech conference: “Maybe some % that is substantially larger than 95% of VCs add zero value. I would bet that 70-80% add negative value to a startup in
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@gm_mertd
Mert Deveci
on x
This is what “f you money” looks like. You can just call out the most famous 3 VCs out there and tell the horror stories publicly instead of just going “anon VC” did me this and that
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@alexrkonrad
Alex Konrad
on x
oh my god
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@thdxr
Dax
on x
my worst VC story: [unnamed] partner stopped me mid pitch. this was pre-covid so these were all in person he walked up to me and whispered in my ear “damn ur a hot piece of ass” he smacked my butt and said he wanted my whole seed round i was offended and left his bedroom
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@vkhosla
Vinod Khosla
on x
Apologies, I may sometimes be wrong, but I will always give entrepreneurs my best and honest opinion, popular or not.
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@antoniogm
Antonio García Martínez
on x
My contribution to VC discourse is that their power is severely overrated, most are just a thin wrapper layer to the real power in the world (the LPs). It is up to you, the founder, to conjure the alchemy that turns labor and capital into value. (You might only realize this
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@eastdakota
Matthew Prince
on x
@heyitsgeorg @pmarca Michelle had tagged along because we both thought getting to meet Marc would be cool. We were running a few minutes late. I was driving so she called the receptionist to let them know. She hung up and looked over to me as we drove down 280: “That was strange,…
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@jarredsumner
Jarred Sumner
on x
I last raised money in 2023 & have no stories of VCs saying unethical things or being rude Personally, I blame @ycombinator
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@vcbrags
@vcbrags
on x
He really went there [image]
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@thogge
Tyler Hogge
on x
At divvy we pitched Rajeev Misra in the SoftBank Redwood City HQ, and then Masa in Tokyo soon after. It was absolute cinema -popping zyns / smoking vape -loud coughing to throw us off -assistants whispering in Rajeev ear -some of the most asinine questions ever asked -in
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@yanabana
Yana Welinder
on x
Let's be real: fundraising is the worst part of being a founder. But you forget most of the bad convos afterward. It's like childbirth. If you remembered, you'd never do it again. For my last startup, I raised 3 rounds and spoke with hundreds of investors. Most of the convos
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@aphysicist
Aaron Slodov
on x
i once heard an investor tell me they thought manufacturing was too capital intensive and not a good venture business lol, lmao
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@typesfast
Ryan Petersen
on x
During a pitch a prominent VC once told us the market size for global logistics was only $6B. My CFO's response: “So you're saying it's smaller than the market for USB cables?”
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@antoine_moyroud
Antoine Moyroud
on x
I'll always remember a pitch meeting years ago. A partner looked at a founder with a McKinsey background, no obvious operator pedigree on paper, who was building in warehouse logistics, and said: “I just don't see you being able to manage a team of operators.” Without missing
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@bradenkeith
Braden Keith
on x
One time I was pitching a VC and halfway through the meeting he started rambling about cicadas, sesame seeds, and Burger King. Then he made his assistant go buy every item on the menu. I sat around for a while trying to get an answer out of him but he wouldn't break focus on
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@samelliottsam
Sam Elliott
on x
Once pitched a reasonably well-known seed VC at The Battery. They loved the idea and invited me sailing a few days later out of St. Francis Yacht Club. Day of: no reply. I texted, called, texted again, then went down to the marina anyway. Standing on the dock, I watched them
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@edwardbenson
Ted Benson
on x
First startup, flew out to Redmond. Half way through meeting, the VP stopped me and said: “Why am I talking to you? Who did you know that got this meeting on my calendar?” And followed up with “This won't go anywhere but you have me for 15 more minutes. Do you want to just
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@philipjohnston
Philip Johnston
on x
I once pitched on zoom and the partner spent the whole pitch throwing peanuts into the air and catching them in his mouth and crunching them. It was weird 😅
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@markpinc
Mark Pincus
on x
A junior partner at a top vc told me he was worried i wasnt coachable. I said, i dont see what you can teach me given youve never founded or run a successful company.
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@drewhahn
Drew Hahn
on x
my VC pitch horror story: i took a meeting with a billionaire who wanted to lead our round. he pulled up in a car worth more than the entire raise and told me he made his fortune putting “radio on the internet” then asked what our ROI was. i started to answer. he meant
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@camp4
Kevin Dahlstrom
on x
VCs are notorious for bad behavior, but I have a story where the tables got turned: The founder of the first startup I joined was a crusty Texan in his 60s with a DGAF attitude. He would say things like, “If you're gonna eat shit, you might as well gobble it.” We were a hot
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@tjack
Todd Jackson
on x
In 2013 my cofounder and I pitched a mid-tier (but well-known, high AUM) firm. Will never forget it. Plush office in Palo Alto, lots of fancy decorations. Expensive gadgets around the office, all forgotten and out of batteries. Framed logos of great companies they had bought into
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@nexuist
Andi
on x
I once pitched a European VC who wanted 15% and a board seat for $50k
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@bcantrill
Bryan Cantrill
on x
There are a few VC firms that we have refused to engage with at all. First among them is a firm that many entrepreneurs AND VCs warned us about — one that actively harmed companies. So I have heard many horror stories about Khosla Ventures; we can add this one to that list!
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@vishalmisra
Vishal Misra
on x
1/ I once had a VC visit me in my office at Columbia when he knew I had a term sheet from another tier-1 VC. We had a great conversation, went for lunch and came back. He then said “you should come for this founder dinner our firm has in Boston today, you will love it”.
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@0xdirichlet
@0xdirichlet
on x
Last year, we were at a dinner, where a UHNW individual worth >$10B and the lead for a large fund was dining with us. An existing investor had introduced us, and told me to pitch him at dinner. “His English isn't great, but pitch him.” I spent the next 30-45 minutes
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@gergelyorosz
Gergely Orosz
on x
@levelsio @travisk Rumor had it at the time that Benchmark wanted to kick him out (and succeeded doing so) because he would not take Uber public, but the fund wanted a return (and a CEO who would take Uber public) Ofc not sure we'll know the “why.” But yes, his investors removed …
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@rkbench
@rkbench
on x
Maybe the best VC call I've ever had was early on with @lessin. Within the first 3 minutes he told me he was out. And spent the next 30 minutes of his time walking through his framing of our thesis, why he thought it was the wrong way to look at things, and how he'd improve it.
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@paulg
Paul Graham
on x
The same investor will react differently to the same idea based on how hot a deal you are and how much they like your personality. If you're not a hot deal and they don't like you, they'll look for reasons to hate the idea.
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@ashleymayer
Ashley Mayer
on x
On the other side of the table, I have a few insane/offensive founder pitch stories but I've filed them all under “accidental diligence” and consider myself lucky. More data! 😇