venture capitalist

“We do get jaded, and we do get experienced and influenced by our failures. And if there's something in the past that I have done, I had invested in, did not work out, that's going to leave a bias on it. It doesn't, you know, no matter what I say, it does impac…”

“We ask ourselves, how much of the company are we gonna be able to buy, ah, for the investment that they need? And the investment they need is 12, is 18 to 24 months of runway. So, you do the financial model, you say, we need a million dollars to take this 18 m…”

“I think it's a dangerous zone. It's a higher beta scenario. It's either going to make you worse off or far better off. If you've got high emotional IQ, integrity and pretty good social skills, you're almost always going to be better off.”

“In first meetings, As a venture capitalist, you're trying to dream the dream. Like you, the red flags are everywhere. You could, you can find hundreds of reasons not to make an investment. You have what you're looking for. Yeah. What you're looking for is that…”

“If you just look at valuations, and you look at round sizes, and you look at the sheer dollar amount of money raised by venture capitalists and deployed by venture capitalists in 2014, it's approaching the levels we saw in 2000.”

“It's really, really difficult to scale venture capitalists. The companies we invest in, they have to scale, but we personally, we're not very good at it. So VC really, you know, struggles to scale in its current model, at least”

“We've done a study now, we did it back Right after the bubble, and we've revisited it once or twice with Dow Jones, looking to see what this, what a typical workload, a board level workload is of a venture capitalist, and the number comes back six, and it was …”

“But it's really all about getting getting other people to sort of lobby for you.”

“So, so I always find venture capitalists Who are smarter than me, who have more successful track records than me, and if they're going into a deal where I know also they're gonna be in the next round, and the next round, I'm happy to invest alongside of them. …”

“Venture capitalists, when you really get down to it, invest primarily on the basis of pattern recognition. They see things working, and they see similar opportunities, and that helps them de-risk their investment.”

“When you have too much time on your hands and maybe a little bit too much proximity in some cases to your investments as a venture capitalist, you have a tendency to feel like you're doing a lot of good by, you know, swinging by for a day, for example, or hold…”

“I feel like you're at a great advantage if you've been an entrepreneur, because so much about being a good coach, being a good mentor, is really understanding the journey that the entrepreneur is going through psychologically, physically, emotionally, and what…”

“When we look at those opportunities through the lens of a Venture capitalists that needs to make a certain return for their fund and hence kind of has a requirement in, in, in, in, to invest in companies that can scale to, you know, a hundred million dollars i…”

“There's nothing fundamentally difficult intellectually about being a venture capitalist. Like, it's not like you need to be a rocket scientist to do it. In fact, people sometimes who are too smart can be terrible investors.”

“The difference between being an asshole and being someone who does their job well is you tell them early enough.”

“Some people are become very good venture capitalists just coming straight. I think if you want to be an entrepreneur, you should just go be an entrepreneur. If you want to be a venture capitalist, you should just go be a venture capitalist.”

“I think there are not enough venture capitalists who help really help with the tactical stuff as opposed to the very large strategic stuff.”

“As long as you're dealing with venture capitalists, they're going to be solving for trying to back the winner. And they would rather back the winner at a much higher price than put something into a company that's maybe doing okay, but not great at a much lower…”

“If you're going to be a seed stage investor, there's nothing like having founded a company, right? Walked a million miles in their shoes. Or if you're maybe even going later stage, I would say just operate and operate well and take those learnings to becoming …”

“I don't think anyone's market ready from the get go. I think it's a flawed assumption with VCs where they try to imagine that, that these first time founders or any founders are going to just figure it all out.”

“I don't think there's any way a venture capitalist can know what they're going to invest in until You know, they meet the battlefield, right?”

“And one of the parts of venture capital I think there's sort of two types of venture capitalists. There's one that just has all their deal flow and they get to pick and choose their deals. And there's others that have to be more hypothesis driven.”

“90% of the value added of a venture capitalist is finding and choosing the right investments.”

“The VC is trying to do seed. You know, you see so much failure there, right? You see, it's just a different game.”

“What it net results in is that venture capitalists can dole out the money and mitigate the risk over time, and so if I put in 500,000 dollars into a firm, live with it for a year, and then I have another investment decision to make, That's going to be a better…”

“Most investors look for something on the order of a three X money on money return, in a fund and a 15 to 20% IRR net to them, net of fees, net of carry, net of any compensation to the venture capitalist return to the investor. And if you can't achieve those me…”

“They're not really strong thesis around, you know, hardware being transformed. And it's, you know, it's now this software enabled experience and the economics of manufacturing are significantly different than they were 20 years ago. There's very few VCs that a…”

“I think some people become VCs because they like the opportunity for fantastic returns, and some people become VCs because they read too much science fiction.”

“Every VC can add a lot of value in terms of team building and recruiting, and most don't because it requires work.”

“It is amazing that for a group of people that fund disruption to be so oblivious to disruption happening to their own business, it is It has been fascinating to me to see people who fund disruption, not understand that an iceberg hit this business over the las…”

“Yeah, I mean, just to speak to that response for a second, that drives me insane, right? Like, let me say you don't have enough traction, right? You're either not able to articulate something actionable, or you're just trying to be nice, and you really don't l…”

“One of the things I have found a little bit disturbing is this rise of kind of the celebrity investors or all of this need to do personal branding, particularly for venture capitalists early on in their career, because I think what really demonstrates if we're…”

“What VCs generally do is they rely on their systemic ability to sort of perceive these things in meetings or reference checks. One of the things they don't do is systematically evaluate and try to dig into what are the relationships between co-founders look an…”

“Venture capitalists in general are lemmings, and when the times are bad, they get out of the market.”

“Most people choose to stay uninvolved, or they use juristics, like if two founders are fighting, you know, the obvious venture answer is like, kick this person out.”

“I'd love to see venture capitalists provide an SLA, a service level agreement, put their principles and values directly online, concretely, talk about control versus not control, what valuations that they offer, et cetera. I'd like them to sell and price their…”

“It's kind of like a test audience where you can give the pitch, you can talk about the vision, and you can either have crickets on the other end, or you can have someone that's very enthusiastic, and that's often a very good signal I've found.”

“I actually happen to find the venture capitalists that find me to be the most helpful because they already have a thesis that they're working from.”

“People that go out and read a handful of blogs and then decide that they're going to be investing in these categories are likely to experience a lot of pain.”

“My alarm to every founder is the more a venture capitalist says, I'm going to be helpful after we invest, there's usually less likelihood that they will be helpful, right?”

“There's a number of deals that we've invested in, That I'm a hundred percent confident there's not another venture capitalist in the world that knows about it because we were there from day one and we know that the founders never talked to another venture capi…”

“Venture capitalists run in certain circles, and entrepreneurs run in different circles, and They do overlap at time, the cocktail parties and things like that, but for the most part, they're pretty distinct”

“When you're a venture capitalist and you are also an active founder, it gives you a certain kind of cache and a certain credibility that I think that really resonates with founders”

“And I think that flies in the face of a goal as a venture capitalist, which is to build big game changing businesses that matter to lots of people. Part of the thing inherent in that goal is making it accessible and opening up it to a broad audience.”

“When it comes to this idea of whether you should be price sensitive or not, there's a lot of different opinions, and none of them really seem to be backed up by data, so it'd be interesting if a venture capitalist came on the show and said, look, we analyzed o…”

“So the venture capitalists have been investing in mostly business model innovations as a distinction from technology innovations, and those are things like, when you think about it, Uber isn't really a tech company, right? They build a, an app, so they use tec…”

“The number one thing you have to do is get good at losing because it's going to happen way more number of times if you're doing this right than winning.”

“And we started to talk to some other people and really found out that, you know, no one was interested in funding hardware startups. And so we asked around, we said, well, why? And they said, well, it takes too long and it's too expensive.”

“Venture capitalists have become a little bit too obsessed with the technology itself versus the way the technology accomplishes creating a highly compelling business.”

“You, as a venture capitalist, get to see the entire industry and all of the companies that surround your portfolio companies. You're probably better, or should be better, at understanding competitive dynamics and how the shape of the market is developing overa…”

“You can either be a very thesis-driven venture capitalist like Fred, or you can be a very founder-driven venture capitalist like Bijan, and I think, you know, what fits better for my personality and the way I see things is being a founder-driven venture capita…”

“Quite frankly, I have a huge amount of VCs say, like, there's no way I'm ever doing that again. I don't want anyone to misconstrue it.”

“There are a lot of other venture capitalists that don't necessarily want to have a vision. They want to view every market opportunity and every business opportunity as something they can read from day one on a spreadsheet. And that's just a very, very differen…”

“And so I think the marriage of both of those two is what makes a venture capitalist great.”

“Preemptive rounds are best suited for venture capitalists who have large funds, because I think it's much harder as an individual to manage capital relative to guessing whether something will work or not.”

“Everything you say to an entrepreneur you work with has to have intent. You can't let your stress, what's in your head, or your mood impact them.”

“There's a really great Fred Wilson quote where he talks about VCs making their money on their big winners, but the reputations on the companies that struggle. And I think building that good reputation is what gives you a chance to work with the next generation…”

“So rather than being kind of a generalist, the only way I can have any edge in terms of competing with other venture capitalists is if I really go deep on one or two topics.”

“Yeah, I think what it does is it forces venture capitalists to make decisions that aren't entirely informed. So if you actually read a white paper it's basically 30 pages of really technical information that requires diligence, which you couldn't possibly do i…”

“I mean, I would say that this is the biggest difference between a venture capitalist and an operator. You have to figure out how to spend the most amount of time with the companies that need you least, and the least amount of time with companies that need you …”

“Yeah, well, look, I mean, I think first thing is understanding the limits of what you know, and so I think there are really kind of two core value adds that venture capitalists can have for When, as they give advice, you know, one is sort of, Hey, here's a dif…”

“Experienced venture capitalists and some of the most well-known venture capitalists, Bill Gurley, Doug Leone, Jim Getz, the further along they've got in their career, the more risk they take.”

“The same diligence they're doing on you should do on them. I think you shouldn't be afraid to ask, to talk to companies that haven't worked out and to reference founders that You know, maybe it hasn't gone so well with, and if they're not willing to give those…”

“No one cares about cap table mathematics. Like that's not a dimension on which people choose their venture capitalists.”

“If you're a reasonably intelligent, reasonably quantitative person who has some domain expertise, and I would probably put, like, most aspiring venture capitalists into this category, it's not hard to tell bad from good. That's actually a pretty easy filter.”

“Entrepreneurs who choose to work with you will choose to work with you because you're the best at something, not because you're not terrible at something else.”

“I think, you know, you can put a 10% weight, that's important, but 90% should be, okay, now how confident I am that the person can execute on this brand vision, because it's super easy to say, this is how big my company could be, and this is insanely hard to m…”

“I think that what that means is the onus is really on us as venture capitalists to get to know entrepreneurs way earlier in the cycle. And so I think the biggest thing that we've got to do to kind of try and address that problem is we need to be talking to ent…”

“Any time a venture capitalist opens their mouth, they're probably sending a message to the founder they haven't met yet, and saying that it's going to be 30 years of wonderful glory, all roses, and no thorns, is certainly a better message than screaming, the s…”

“I mean, if you distill everything down to the essence, we're sales reps as venture capitalists.”

“When things change, you have to be pragmatic. If you're reactionary and fearful, and, you know, all of a sudden, everybody says, oh, my God, the world is ending. You know, you must do these things. As a VC, that's not that helpful. It's more helpful to have a …”

“I think market risk is the most dangerous risk to underwrite. Even if with the greatest teams, teams can't fight market. Market always wins.”

“I generally think that, and your podcast is probably helping this in many ways, in a good and bad way, there's too much focus on the venture capitalists. There's too much focus on the investors. At the end of the day, why companies are successful is because a …”

“If you had asked every single venture capitalist at the If dating was an interesting space, nobody would have raised their hand.”

“That what you signed up for is to be supportive and demanding. Because you want them to fulfill their potential and frankly do things they're not even maybe sure that they can do, but you want to see them succeed. That is at the heart of what you signed up to …”

“Usually, you know, 10 minutes into the pitch that they're probably going to say no. You can just tell from their demeanor and how they're asking questions and stuff. But I'm like, you know, I just need to sit here for another 40 minutes, right? So I'm just goi…”

“I think that a huge mistake is not bringing in operators and independents soon enough. What happens is you have the normal progression where there are more and more rounds getting raised, and yet another VC Nothing against us, but yet another VC joins the boar…”

“In fact, that's, I think, one of the least imaginative questions a VC can ask is, like, well, 10 people have tried this, and it hasn't happened, so I don't think it's going to happen.”

“I'm trying to do my marginal best, and the company's doing extremely well, and I like to think I'm helping somewhat, but I'm not the be-all, end-all. I'm not the difference maker.”

“And that, by having had that conversation at the beginning, and having made that when you were discussing what your partnership would be like, what the alliance would be like, in terms of what you're doing, then people go, look, I wish I had more time, but I f…”

“I think, you know, it is true that when companies are not doing well, they'll sort of ask for more help, ask for more advice or whatever else. But I think in the end, it doesn't actually make that much of a difference. You may sort of spend more time with the …”

“A venture capitalist never knows whether there's one new deal, good new deal ahead of him.”

“And this is a teachable moment for me because next time, if the risk is that I only make two or three X, quickly, not after five years, then I should have done it. And I'll tell you why, because I totally forgot that I could recycle the money. So in the unfort…”

“I think it's a bad idea for venture capitalists typically for a variety of reasons. One is skill set. Second thing is most LPs do not in fact want that. They're hiring Venture as an alternative asset class.”

“The reason that investors aren't as directors, they should be most often in terms of the feedback is because they want to retain the optionality. If you're a multi-stage fund, You don't want to say, Mike, I'm turning you down at the seed because I really don't…”

“A positive sign would be them walking you through their entire portfolio, and especially how they serve the founders when things were not going so well. A negative sign would be Them taking credit for the founders work, and there's nothing more sinister than t…”

“Right now, many founders will tell you that if a VC is not harmful to the company, that's already a success. And I say the expectations should be higher from founders because while a VC cannot play the chess game for you and move the pieces. They have seen a l…”

“And you should work in the evenings, and you should work on weekends. And if you don't, like, I, like, I just don't think you deserve to be investing in these companies. You just don't.”

“I think the biggest one is VCs have a portfolio and the founders have N of one. And so, yeah, I try to be very explicit on that. You know, the founder says, okay, I have a fork in the road. You know, what, which, what's your point of view on where I should go?…”

“I think your average venture capitalist does not spend a lot of time in computer science research”

“They sometimes act almost as CEO or, like, operators for companies. Which in, in my opinion is, is not really their job. And worse than that, I feel like sometimes entrepreneurs are building companies for investors and investors are behaving like entrepreneurs…”

“I actually tend to find that always, in the same vein as like a founder's fund, the best founders never need me, and they just operate in isolation, and I might be there, but they don't need me.”

“And if pricing doesn't correct at the earliest stage you're going to have a lot of no bids, you know, at the Series A because they wouldn't have gone far enough, fast enough for a Series A investor to come in and say they've earned their way into a significant…”

“Founders and investors, both we've kind of slipped away from financial acumen as investors, where it just became really focused on revenue multiples.”

“I think you can, you shouldn't be too involved with portfolio companies. It's you have a portfolio. I shouldn't be an advisor.”

“I think this is why shows with venture capitalists are very difficult, because, you know, the venture capitalists don't even know who they are, so it's difficult for them to say it on a show.”

“The analogy that I use is that we're not like you know, the entrepreneur is the captain of the ship, but we're not next door, you know, shouting which way to go. We're like the lighthouse. We just tell them where the rocks are so they don't crash, but we actua…”

“Tech shifted from a vertical to a horizontal. So the places, the types of businesses that venture and early stage tech venture capitalists were funding fundamentally expanded at a huge level too.”

“Yes. And you know, and you can get away with it sometimes, just like I got away with it, with that early deal. If you can find, you know, other people's money on advantageous terms to sort of fund you through you know, the valley of death there you know, like,…”

“In the time, 2000, you know, mid 2000, if you tried to raise money, essentially the product that venture capitalists offer was a ten million dollar series. A was sort of the smallest check.”

“I'm not looking for a customer call To turn a frown upside down. I'm not looking at to take a marginal investment. This is, I think what VCs used to do in the old days is they'd hope, right? I'm looking only for confirmation with customers.”

“There's this really interesting research that shows that venture capitalists Are not swayed at all by the quality of the speaker. Their ability to be a good speaker or not is absolutely irrelevant. Amateur and angel investors are swayed by that.”

“The best founders don't want to meet with VCs. That's the reality of it. You have to convince them.”

“Especially on structuring rounds, people will bring in people who are maybe not the best fit for the company, But they owe them for a deal that was done before, or they want to curry favors with people. I see this a lot where I'm like, hey, hey, the head of gr…”

“My gut reaction is to say the opposite, which is that, you know, The wealth level correlates with a lack of hustle and therefore, but it's, that's actually not in practice what I'seen. I think there is a correlation less about the money and more about the peop…”

“What I don't like is, is overly benchmarking or following like playbooks from other companies. I feel that's, it's almost like it's templating the business. Like you are Not really thinking about our unique challenges. You are applying this template from somew…”

“Yeah, I'm kind of in the same camp. There's no upside from, like, arguing with people. I mean, argue with your founders who are, like, in your, like, they're in your family, right? You're an investor, you're a long, but, like, there's the outside world.”

“Bing is actually great. You know, Bing is, is, is a rare type of investor because he is very product minded. You know, he uses the product and he gives us a lot of feedback on the product. He's obsessed with product. Most investors are more, you know, they're …”

“Venture guys make really good thematic bets about the next 10 years and are pretty horrible at assessing how the market's going to react to the next quarter's data. Hedge fund guys are the exact opposite.”

“The public markets are now pricing risk very differently than they have over the three, the last three years. You look at circle, you look at, you know, Nebius, you look at core weave, you look at Palantir, you look at cloud flare. Like these are all businesse…”

“I'll bet you nickels to dollars that doesn't happen because founders are just signing up. I don't know what Brian you see at Sequoia, but founders are signing up for crazy stuff these days. They're signing up for massive stuff. And I don't think a lot of grouc…”

“Also, you know, I think we have a, there is a tendency where the, sometimes, you talk about, you know, asymmetry of information, but it goes both ways, where sometimes you're so close to a business, you really see how the sausage gets made, and you can end up …”

“You can't leave a founder in a deal Where he didn't want to sell, where he wanted to sell, and you stuck him in the deal, and now he's bitter. And if the thing goes wrong, you have no idea how toxic that will be.”

“When there are situations of chaos and folks don't know what's going on, the safest thing is to go look at other social signals to make decisions instead of using your own gut. And so I think that that's happening a lot in AI, and hopefully, you know, as the m…”

“Here's what I think. I think we tend to consistently underestimate how big the markets are and consistently overestimate how easy it is to go from zero to one, right?”

“That's going to be the deciding factor for venture capitalists. And startups. We're going to be on the same level playing field. How well do we use autonomous agents in our job?”

“And I think that's right because realistically, in the journey of what's going on, the only significant things we've done, I've said this before in the podcast, we put in the money and we put in more money when they need it. We decide to hire or not hire and f…”

“I just see too many VCs running a pre AI enabler playbook. Where, where, where when folks do fall behind a tick or two, the, you see kumbaya activity instead of code red activity.”

“Context feedback loops where you are, you have unique and differentiated access is where progress will be most legible to you. And if there are other teams who don't have access to that context, it'll also be where you have a superior business model.”

“So what I've learned to do, which is really hard, is literally listen to the idealism Don't say, do I agree or not? Say to myself, will it motivate people enough to do something where there is economic advantage to be obtained?”

“Well, the VCs always win. If they do a price round, some of them are sharks. They say we want a 15% option pool at the seed.”

“So I think this raising the next fund nonsense really does impact decision making and actually directly hurts founders with some of these things.”

“99% of them are not. They're, I mean. Because they've never been operators. So like, they're just regurgitating, you know, something they heard in another board meeting that they think might be.”

“And where there's innovation, you can find early teams that are doing science experiments before anyone else is thinking about them. ... I think those are the best places to bet as a venture capitalist, because in the earliest days, they're actually not that c…”

“Anyone in my seat who says, I knew, is just full of shit.”