venture capital

“There was not a single VC or angel out there that wanted to touch anything tech in 2001, 2002.”

“Venture tends to push a kind of short term thinking. You know, oftentimes there's a conflict. In the business between doing what the right thing for the business would be if you were to run it for the next 20 years versus doing the thing that's going to allow …”

“I think, like, if you had invested in Fluidware, you would have told us you're not allowed to do that. Like, let's do the math here. So, 25,000 times 25, what is that? Like, you know, 625,000? Like, that's your whole market? Like, you're doing all of this for …”

“I think the expectations of the market of a new startup, whether it's VCs or actually your buyers today, are much higher than they were eight, nine years ago.”

“The fundraising for the first couple of years was extremely hard. Because a lot of the VCs, they go to very top schools like Harvard, Sanford, Yale, Columbia, and those schools, UPenn, and the fact that someone's like, sell their home and belongings in India t…”

“Actually like the rejection for me was a little like even harder to, you know, emotionally harder than that, like rejection from the disease because, you know, this person can make that decision versus, eh, I can't confirm that my firm doesn't want to do that,…”

“Normal series A negotiations, I've seen many of them now, they're not really that exciting. I mean, for the most part, evaluation gets said by some lead VC, and almost always the founder accepts it. Maybe they negotiate a little bit. You know, if they have mul…”

“And then if you're raising from VCs, I don't know any VC that isn't happy doing a pref round, like a price round. Almost most, most VCs are happy to just do a price round. By the way, like most times we don't do a price round because the founder is the one tha…”

“And I've seen so many companies, especially in the last few years that raised more money than they're worth. And so now the founders find themselves in a position where they sold their company, which has revenue, which has growth, which has a real product that…”

“Go in, have a deck ready, present the deck, walk the person through it, control the conversation. This is a pitch. This is the, oh, let's just have a conversation is like, yeah, that I terrible. Never do that.”

“For sure, the FOMO is gone, like, it's way worse, and I think everything's just going to, like, the rounds are smaller the rounds take longer, there's just, like, less appetite for risk”

“That's not going to like, if I'm not interested in the company or whatever, like that's not going to make me just invest. But if I'm already interested, that can definitely get me to drop other things, put this one at the top of the pile and figure out whether…”

“The, probably the most proven way of building a great company is sustainable, consistent growth. You look at Nike, you look at Microsoft, you look at Shopify. These were businesses that what they actually did was they doubled and they doubled and they doubled …”

“The longer startups can stay experiments without these external stakeholders and their only stakeholders are the people on the team. And then the customer, the better you can run experiments and the better you can actually find value.”

“The founder intro is one of the most powerful intros you can get to an investor. In my experience, like they trust their own portfolio companies. Or at least they know if they can or not. And if they say it's a good fit or like, you'll get the back door entran…”

“This is like the warm intro or like the external validation for someone they trust. And it's like an extremely, it like ticks, checks a really big box and gets you in this fast track lane with an investor and because they, they're looking for proof signals. Ri…”

“When you raise, you kind of, you're taking on a certain path, right? You're limiting some of the options or trajectories or directions your business can take.”

“You often pick a few that you have good relationships or you can get intros that aren't necessarily high value. And these will be your test subjects in a way that you're going to be, you're going to bounce, test the story on, see the reaction, get the feedback…”

“Their incentive structure is such that you're going to by your very nature, right? By your, even your existence harm a lot of, Small and startup companies in exchange for a very small number of winners.”

“Even a hundred million-dollar startup should feel ridiculous to most people, because the odds of that happening are so vanishingly slim, and it's weird to me that we all talk about this thing that's less likely than most lottery wins, so, you know, I don't tot…”

“I can see the metrics on my docs and the average investor spends like between one and two minutes max in my deck.”

“And so after 10 to 15 meetings, though, you probably heard everything people are going to ask you.”

“You have to get into the mindset when you're in fundraising that investors are trying to sell you an investor. Cause like they, they're selling the most commoditized product in the world, the us dollar.”

“What you're talking about doing all that pre-qualification happens maybe like five percent of the time, right?”

“And there are a lot of good ideas that never get funded, not because there's something wrong with the idea, just because the founders never figured out how to tell the story appropriately.”

“It's like a lot harder than raising for a startup. But dude, I'm pretty sure that your average VC raising a fund will have this mental limits and they'll think that, I don't know, BlackRock would never invest in them or that the Saudis would never invest in th…”

“Getting a single strategic investor is, is a risk. Hey, if they don't like you anymore, what does it say about what you're doing, having to maybe not solve it, but we have dozens. So basically if you can convince the whole industry, the whole very smart invest…”

“I also think, I mean, more this year than any year that I've been focused on startups, there's just a ton of founders who are not as enamored with venture capital overall as a pathway. They're just like, yeah, maybe down the road if I need it, but pretty much …”

“Just kind of right at that 20 to twenty two billion dollars a quarter mark. And that, if you look historically in the beginning of 2020, it was pretty much, it was, it's a little bit higher than the beginning of 2020.”

“The big takeaway that I have from the location data is that it's easier to raise venture capital now across many, many different places in the U S than it ever has been. Like there are actually growing ecosystems in places that, you know, five, 10 years ago ha…”

“The frustrating part is the companies where they had some growth, but then it stalled. But because of the amount of money they raised and spent, there's just nowhere to go. And it's like, you look at the business on a spreadsheet and you're like, This is an ok…”

“What I would say is different about the process, though, is the conversation becomes less about what could be and, you know, pitching the vision in 10 years. And it becomes more about the kind of like ground truth of what can the product do today? Who is on th…”

“It's actually a very conservative strategy because you'll take this money that you don't need, so you're preventing a risk that you don't know is necessary. But you do two things. First, as a founder and funding team, you spend a lot of time raising money and …”

“Your best, best intro is someone that's made the money. Maybe second best is, is someone they've done deals with in the past, you know trade deals. Maybe it's an angel that's fed some deals to the, a VC or vice versa or whatever. Third best is I would say some…”

“Like if our firm says prices are really high today, sure, we could sit and do a little bit less, but we can't just exit the market for two years until things come back to normal. It's just not our business model.”

“At least from the perspective of VC, it'll get a zero multiple. It literally will get roll count towards where you're at, right? Like, so no, you say I have two million revenue. Million and a half is implementation revenue. As far as I'm concerned, you're at h…”

“Venture, I think, is going through this moment of, it is not this tiny, kind of scrappy asset class anymore. It is professionalized. We probably need to start talking about it the way we do with private equity, where there's like low, middle, high. There's dif…”

“Saw about, oh, about 20%, 18 to 20% more cash raised by companies on Carta in 24 than 23. So that's obviously a boost, but the actual number of rounds was down about five percent.”

“Over 15 years, he pioneered a lot of the concepts in BC, like general partnership, limited partners, carried interest. He accumulated over that time assets that today would be equivalent to like thirty eight billion dollars in, you know, adjusted GDP terms.”

“One thing I've realized is VCs are kind of like art critics, where they know what greatness looks like. They can distinguish between okay art and great art. But in many cases, it's been some time since they've, you know, picked up a paintbrush, or in some case…”

“After the angel round, we had a very hard time raising any VC then to top up because no one wanted to touch SME back then. So SME was kind of a dirty word, right? The SME businesses really did not make money. SaaS for SMBs was just not there yet, especially th…”

“Product market fit is the thing that's going to give you the venture type growth, right? The truly exponential, hard to control growth that puts you on a path to like a hundred million plus in revenue. If you want to build like a five to ten million dollar bus…”

“If a VC doesn't allow you to take out secondaries in your company, run for the hills. That's a predatory VC.”

“Look at their portfolio of the VC. They will have, you know, 50 to a hundred startups on their website. Find a founder who can help you and hustle your way to get that into a warm introduction. That's the highest quality introduction you can get.”

“I believe that pretty much every successful VC is a solo GP, whether they're part of a large firm or not, or on their own.”

“We cannot only choose to work with people who we've known for many years. That's a very myopic view of how to be a successful venture capital investor. We have to. We are forced to get out and go make new friends.”

“The thing that I think people don't realize is the more money you raise, the less people actually look at your business.”

“The best thing you can say to a VC is no. Yes. Like that's when they want you. I like to refer to them as like high school girls. It's like they, no one wants you until, like, somebody does, and then everybody wants you, and then, but, and then if you say no, …”

“We picked, like, 30 VCs, and, you know, they all said no and so we had no money, I had some savings, I had, like, maybe 20,000 dollars of savings”

“Everyone sort of feels like I have to raise money to build a company. And it's, that's not true. The difference between like, oh, I want to build a million dollar company or a ten million dollar company or a hundred million or a billion dollar company. Like th…”

“If there are the millions of businesses that we are claiming, then other people see this opportunity as well. They're going to go hard. They're going to go raise millions of dollars to capture it. And they will steamroll us unless We're like going at as hard a…”

“It's not that seed strapping is a bad way to build a business. It's actually a fantastic way to build a business. It's a bad way to get venture returns. And that is the fundamental mismatch between the investor expectations and the founder expectations that I …”

“When things get hard, you need one decision maker. I believe this really strongly. So I still believe the fifty-fifty rules that a lot of VCs try to push is not the best because I really do think that no matter what the decision is, there has to be somebody de…”

“It's like you're raising in seed. You have no idea what you are going to go and where you're going to go. So just wait to spend the money. I know there's this idea that VCs want you to raise again in 18 months, but, you know, make yourself arrive to those 18 m…”

“I think for the most part, raising a lot of money early is it, it's, it makes the company worse rather than better for the most part.”

“There's another story about, I guess I would call it behavior change and venture capital, which I think only can be facilitated by a policy intervention.”

“When I went out to do my fundraise, like it took, literally took like 24 hours. I think there was a lot of interest for VCs.”

“VCs don't give a shit if you have product market fit. What they really care for is, you have churn, but your upsells make up for the churn plus more.”

“Which in hindsight was probably the best possible raise that we could have done because by getting a big name early on to take an early bit of signal and no one's heard of it, then it's just the hottest.”

“However nervous and anxiety ridden you are about this market, just know that your VCs are equally anxiety ridden unless they work at Andreessen or Sequoia because their fundraising process is super hard right now.”

“So you might bridge a company. For the express reason of having better marks to go and show your LPs when you go and fundraise. And so that might be the primary reason you did it. Even if you're like, I know this founders and probably don't get there.”

“There are a hundred AI powered CRMs now. So pouring money into the eighth best new AI native CRM is a waste of money. And it will be over time.”

“Cause I think if we were venture business from day one, we would not survive that long haul.”

“VCs will give money to what is a hot commodity, so then something can give them, someone will give them up round, and you can go to your LPs and say, hey, I'm up 90% on my portfolio.”

“I think that is another trap is that as second time founders, there is no shortage of capital that is chasing you. And if you're not discerning, the capital won't be.”

“And like, I think that probably a second time founder is kind of the sweet spot. Like if I were a VC, I would often be looking for like second time founder where the first thing they'd gotten some traction, it wasn't like a total dud, but it wasn't like a runa…”

“My job is to understand this industry, like the market, the future of the market, where it's going, like see around corners, do all those different things. Like that's my job. And my job is to be the best in the world at that. Their job Is to be the best in th…”

“It's very easy for them to invest in a next gen something or invest in a new category. But if you're telling them, Hey, this problem has been around for a long time and nobody solved it, that scares them.”

“Having that kind of initial touch points, the speed of response, it's the only window you have into that new relationship. And so from the founder's perspective, whether it's selling to an enterprise or pitching to a VC, whatever, you might imagine that like, …”

“You want a corporate lawyer who sees a lot of activity and ideally a corporate lawyer who never works with VCs, but only ever works with founders.”

“I raised 30 rounds of venture capital.”

“You're going to start seeing this across the venture capital and private equity ecosystem, whereby you're taking technology companies, best in class technology, best in class, artificial intelligence, and you're pairing it with best in class operations or rela…”

“When you look at the data quarter over quarter in terms of venture capital rounds and whatever, you know, there's been like a steady increase the last, call it, year or so. Rounds are going up, although capital is moving much faster than that.”

“And I don't buy into this idea that as long as you get 20%, it just doesn't matter what you pay. Like you just intrinsically doesn't make sense to me. You know, you're going to affect your ultimate return. And if you do it all the time, you know, it's going to…”

“You know, they want some level of greed to be clicked on. It's like, oh, If they do this, I can see why they would make a lot of money and make me a lot of money. And you have to then, once you do that, reduce risk, right? Basically show a through line between…”

“If you're not a tier one or tier two VC, like a lot of those are just like trying to take advantage of people. They want your time. They're essentially like vampires in my opinion.”

“The way that this VCs would open up to Amanda AI versus open up to me. They would be much more transparent. I could tell right away from a few turns of interactions whether they're going to invest or whether they'd be interested.”

“And I think that comfort doesn't make them less motivated. I actually think it just makes it easier to like, okay, more things are taken care of. I can take care of my family and now I can put more energy towards the company. And if you have somebody who has a…”

“Some VCs play this game and they shouldn't, but they do, which is you might get a meeting and think you're having a genuine conversation with a VC that knows and gets your Only to later find out that that same VC invested in another company that's a competitor…”

“Do not set fake deadlines. A lot of people misinterpret this and say, okay, if I want to drive FOMO, I need momentum. I need timelines. So I'm going to go in and I'm going to meet VCs and I'm going to tell them, oh, I'm closing the round by end of March. It is…”

“If I, as a VC, make an intro to another VC, the first question they're going to ask me is, are you investing? And if I say no, I've just deflated that balloon completely. So the last person that you want to intro you to other VCs Is a VC.”

“The elite option is actually to say to them, we have a data room, but we're only letting investors in on this date. For example, if you're running these intro meetings over two weeks, then maybe at some point, During that second week is the time that you let i…”

“So if you want three term sheets, you're going to need to get 10 firms to that final stage where all partners review the opportunity. So that 30% of those actually get you a term sheet. Now, if you want 10 partner meetings, that means you're gonna have to have…”

“Whatever you give me is the absolute best case. That's how I have to take it. So if you're being conservative, you're Just lowering that ceiling because I can't take what you say and then go back to my partners and say, you know, this founder thinks they're go…”

“If you give a number, All you're doing is transferring power to the VC because if your number is way too high, the VC is going to maybe just pass because what you want is not market or just doesn't make any sense. And now where you would have gotten an offer, …”

“The best intro source is another founder. When I have another founder that I think is a solid founder, reach out to me and tell me that I need to meet a third founder that they know I'm already coming into that call with high expectations.”

“The difference between going out and saying, I'm going to raise two million dollars, and then you get a hundred K or 200 K, you're only five or 10% subscribed, no momentum, no FOMO versus if you're raising two 50 K and you get a hundred K or 200 K, you're 50 8…”

“I think historically, even though we said they were winner take all, we never actually believed it. Like you can do pretty well as number two. Now I think that is an open question, especially at the scale that you need to go back again to the Decacorn plus kin…”

“If you come out for the A and if anyone is listening, if you come out for the A and you say like low teens or like not even below a 10, it doesn't seem like you're ambitious and it just doesn't make sense to like VC math.”

“We're paradigm shifting system engineers. We're trying to bridge that gap between basic science and something that's like venture investable, but that's like often a five or six year gap that gets filled very badly.”

“If you cannot crystallize it for your investors, You won't be able to crystallize it for customers, and VCs are not necessarily forward indicators of the market, but there's some derivative of what your customers are seeing, because if everyone wants to buy yo…”

“Every time I go on a call with the VC, that VC probably wants me to be the best founder that they've ever met. I mean, that's their job. They want to invest.”

“And at the end of the day, a VC that invests in you and the seed round, all they need to really think about is will there be an investor that leads the A round, right? And the A round for B and the B for C.”