founders

“Two. Business and a tech.”

“There are a lot of companies out there, founders who could build very small, successful businesses but take venture capital because thinking it's the only option, and basically destroy their return.”

“So I think starting with aggressive asks can get people turned off pretty quickly and you can reduce the, you can change the dynamic and take bidders away. Whereas if you get a whole bunch of people bidding at an average valuation You may end up with a very hi…”

“If they don't have a natural, if they don't naturally belong in the market they're operating in, then That's a bigger risk, and probably not one that we'd want to take, because the risk of them getting bored, even, is, you know, is material.”

“Once you have a term sheet from a fund, go ahead and ask to meet three or four of the entrepreneurs that they've invested in. And often I suggest that you specify entrepreneurs who've been through a tough time.”

“When the tough get going, they start looking at the legal docs and how they can screw the company and the founders. That's not cool, and no great investor does that in the long run.”

“There's no way you understand the business as well as the founders. You're very arrogant if you think you do. There are many people that think they do, but of course you don't because they work. 24, seven thinking about one thing only, and you're probably thin…”

“Hiring operators is really difficult in particular, because their networks tilt more senior.”

“If you can raise at decent terms i.e. A good enough valuation without giving away too much equity, it's probably a good idea to raise now, even if it's a little bit more than what you need.”

“So at version one, we know that The first 18 to 24 months after we invest are probably the most important time, so we try to be as involved as possible, and this means we talk to our founders, you know, anywhere from two to three times a month, but of course w…”

“I think the reality is that a VC is testing you. They're testing your thinking. They're testing you know, really is the business model going to work? Really is the market as big as we all think it is? And is that really addressable? And you need to know the an…”

“I would much rather that a founder comes in with 15, 20 minute presentation prepared, which probably takes half an hour because, you know, I'll ask some questions and we'll, we'll have a nice chat around a few things. And then we have lots of time to delve int…”

“I mean, honestly, I think a lot of founders make the mistake of thinking that they need to come up with a really big formal pitch. They need to fill an hour. They produce a big IM you know, and they kind of over prepare on the documentation and the format and …”

“Was the finder able to pull in some high profile domain experts? So again, I started up a medical startup. Was I able to bring in somebody that is insanely smart in that field and get them to take a pay cut for equity? All of those things are sort of signs tha…”

“So I think founders nine times out of 10, just do not do the right work.”

“It's less stressful than being in the trenches as a founder. But it quite appeals to me in that you can kind of take a step back and think more strategically and be more analytical Rather than having to be in kind of animal mode every day.”

“Talk to people who have been in your shoes recently in the last six, 1218 months, and it's fresh in their mind. They have a lot of lessons to learn, and they're more than often happy to share.”

“Versatility and demonstrating kind of demonstrating, you know, Kind of effectively outreaching to people and converting, converting leads with no money really translates as something positive once funding comes around.”

“It's ephemeral. You know, my throwaway line is it belongs in the bedroom. Obsession, you know, obsession is a different thing and not an unhealthy obsession, but an obsession that's palpable.”

“You definitely tell them you know, transparency is the key. I just, you know, and the reality is, is that, especially for these types of companies, you want people to know, it's like Headed into a storm. You want everyone to know what they're facing so they ca…”

“Stop building a startup and just build a product. So instead of worrying about all of the paraphernalia that comes with building a startup, just focus on the product that you want to build and the customers that might want that product. So what that means is, …”

“We're trying really hard to make the founders see that actually the cap is not something that drives the dilution as much as the amount they actually raise.”

“I think the thing that we worry about the most is that the best companies won't want to come through YC, so I think the biggest challenge is that those companies decide they want to go somewhere else or do something on their own without having YC's help.”

“The biggest mistake that we see founders making whilst they're fundraising is Well, actually, it's one of two things. The first thing is not knowing when to stop.”

“And then the three months of YC itself is such a great time for founders to be able to push off everything else, right? It's this great excuse to focus. Anyone who wants to talk to you that isn't a customer who you need to talk to or a user you need to talk to…”

“Ultimately, anyone who puts money in your company, you should look at them as an advisor who's incentivized now, because their money's in it.”

“There was also sort of this need for a founder to come in and reinstate their sort of the reasons why the company was started in the first place and kind of bring things to this original vision.”

“You brainstorm lots of ideas, but then the next step is to go out and, you know, talk to people and interview them and observe them and try to understand more detail in that problem. You know, how are people trying to solve it now? Where are their frustrations…”

“In my opinion, I would have thought that the idea about how much equity you're willing to give up should come a little bit later on.”

“Part of the reason why founders get fired in the process of scaling is, is one of is the reason, the primary reason is a breakdown in trust at the board level.”

“I think overall, we probably know our founders for, you know, upwards of 12 months sometimes before we before we make an investment.”

“And I think in retrospect, it's your job as the founder to really dampen this roller coaster for your team so that they can remain productive and give your team a really set direction that they feel comfortable and confident executing on.”

“In fact, the kind of easy heuristic I use for that is, would I want to, am I tempted to go work for this person? You know, I've got all these things that I'm doing my own, and I control my own day and my own schedule, and that's fantastic, and, you know, I can…”

“A sign of persistence or a sign of that they can be persistent is that they've had hardships in their life and have got, and have gotten through it.”

“I think very people try to, very few companies and founders focus on the two or three things that really matter, have a hypothesis about those things, and then try to, you know, prove or disprove those hypotheses.”

“But to me, the, Qualities of the founders are the most important, the most enduring part of any company, and the only thing you can truly understand as an early stage investor”

“For instance, you know, ah, two years back, we were the first venture firm to officially, you know, vote, always with their founders,”

“If we thought that there was a better alternative than the founder for the business, we'd tell the person that. And then if they said, no, no, no, thanks. That's nice. That's your opinion, but I'm going to keep going. Generally, we would back them to keep goin…”

“I mean, the culture in the end, it's embodied by the founders. I mean the company has the culture of the founders as long as the founders consider the culture important.”

“And that's been something that in the boardroom, you see a lot of venture people show up, you know, spend a half hour looking through the materials and assume that they have all the right answers. Living through the experience I lived through, that just feels …”

“It's rarely about the people. It tends to be about some nuance of the market or some nuance of the strategy that, upon reflection isn't as clear as it was when we were together.”

“The hardest thing is being judged when trying to navigate an extremely uncertain decision process. So everybody has an opinion, but you're the only one who actually knows how much, you know, money and each decision will leave you within the bank and that the v…”

“I think there's always a miscommunication a lot of times when, you know, a VCO asks a type of question, like competition, where you see growth, what does this mean? I think in their mind, they want to hear it An answer in, in a framework that they're going to …”

“Yeah, I think the healthiest thing that founders could do with more capital is drive a longer runway.”

“Actually, the expectations come as a result of a tough negotiation where, Not just VCs, but founders typically want more capital and higher price. And so it's on both sides, the intention of the VC to get more capital in and incentives to do so, and the desire…”

“Anyone who puts a trillion dollars is obviously a buffoon and an idiot and just doesn't understand macroeconomics.”

“There are lots of founders. They know they have to claim billion dollar markets to raise money. They claim it. And frankly, it's our job and why we get paid to figure out which of them are wrong.”

“I think this is a mistake a lot of people make as founders, which is to try to get the biggest names or something that they think is sort of like a brand of a particular board member without really doing a lot of work to make sure that you have the right chemi…”

“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…”

“If we could actually sort of make founders partners in the fund, they would be more supportive of one another.”

“So the undercapitalized seed or series A will be the new big risk for founders. It is easy to get that first seed round because there's so many seed funds around and it's easy to do a rolling close and do, you know, a safe note and get your seven 50 K in. But …”

“There's a guy named Noam Wasserman who has found that whenever founders discuss equity splits at length, even if they end up just dividing it 50 50, okay, the fact that they've had the conversation is a higher indicator of long-term company success based on en…”

“And what I realized is that actually what happens is no matter how problematic or screwed your startup is, Everyone always presents externally that things are going fantastically. And so as a founder, you don't often realize this, that everyone starts up at pr…”

“If you raise around prematurely, if you raise like ten million dollars before you've kind of gone through that pain, now you're under pressure to hire people, and you might not have a clear sense of exactly who you need, because every, you know, you keep using…”

“In general, data will fuel great digital experiences. It is likely to be the primary source of moats, and it should be absolutely top of mind for every founder going into a software business of any kind.”

“The challenge is that founders can't really share that information because it's not in their best interest, and VCs don't Really want to be transparent because it's not in their best interest, right? They sort of hold all the power. And what that means is that…”

“The partner is so much more important to me than the firm because there's such asymmetry of information between founders and VCs that makes it really hard for a founder.”

“If someone is going to be on your board, you should probably consider how you select them in the same way that you would consider a partner. In life. Because they're going to be on your board for a really long time.”

“I always think that founders and the portfolio is the most underutilized asset.”

“I think as a founder, you can always be busy, but the only thing that matters is the hardest thing. And a lot of many founders will tend not to do the hard things first. Right. They want to like, it's because you feel more comfortable doing the easy things fir…”

“And the only thing we're judging is the human being, and the founder, and whether we think they are obsessed, hungry to achieve something.”

“Founders have a tendency to underpay themselves. They're overstressed. They're overstretched.”

“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”

“The best founders make me feel like Number one, I can never control them, and I never want to control them. Number two, that given an opportunity to do the insane, reckless, non-conservative versus the rational, logical, they'll prefer the insane and the reckl…”

“If you're a founder, you want to have phenomenal operational experience on your board, but you don't want to have it in the seat that's controlled by a VC because now you've made a contractual commitment to have someone on your board who for most of his or her…”

“So I don't think you need to be passionate about an idea in the beginning, which is sort of controversial in my opinion, but you actually do see founders grow into something.”

“And why are you doing this? Again, it's five words, but it really is one of the most telling questions you could ever ask people. And I just sit there very quietly and listen to them. And I let founders speak and speak and speak until they have nothing left in…”

“Until you are profitable, until you're lording over the investors because you are profitable and don't need their money, I don't advise wasting your time at events, watching television, Coachella, Summit at Sea, Summit in the Mountains, Web Summit, Summit this…”

“For me, an investor that has an entrepreneur background that has been in my shoes, that's a big advantage to me because I think they're going to be able to understand my side of things better. And contrary to somebody who's been recently in the news, I actuall…”

“The problem with saying, well, we'll just raise a whole bunch more on the first round is that it's human nature. You don't divide that number by 36 and spend accordingly. You tend to just Divide that number again by that 12 or that 18. And so then you're spend…”

“We think that the role of the early stage investor is to fully support and fully embolden those founders to take major, major risk and be bold and daring.”

“With recruiters, what I hear a lot with other founders is that they would spend 40 to 60% of their time just trying to recruit the team, trying to look through the resumes, go on Craigslist, things like that.”

“By the way, I don't believe at a fundamental matter, I'm old fashioned in the way that I believe actually VCs should be invisible, you know, and so I know you ask this question to a lot of people, what would you like most like to change in the world of VC? I'v…”

“It's not the VC's job to grab the wheel at the end of the day. It is your job to have the periphery vision. So if the founder's the driver, it's your job to have the periphery vision and say, hey, there's this thing happening over here. I just want to make sur…”

“I know founders who, for instance, have never hired a CFO before, and before they launch their CFO hiring process, they will make it a point to meet the five best CFOs that they can be introduced to. Not to recruit them, but to just get a sense of the texture …”

“The two biggest lies around startups are founders saying, I don't care about the valuation and investors saying, you know, we don't care about control.”

“Founders are put in this terrible situation of trying to do right by their early investors. And respect all of the contractual rights that they signed up for and new investors demanding minimum ownership thresholds. These founders are forced to either screw ov…”

“I think people try to like index way too much for stage specificity”

“There is just this, I'd say, extreme alertness concern that really good founders have, where they never get too comfortable, even when things are going really well. And they're always aware that they're sort of only as good as their next decision.”

“One thing that I would do before making a larger investment was ask if I could shadow the founder for a day or two. At the end of that, spending 12:14 hours a day just watching everything a founder does, I never had questions. I learned so much more doing that…”

“If you believe that talent is evenly distributed, and you're only looking at the U.S., you're going to miss, like, 95% of the best founders.”

“Most VCs that I've worked with or talked to, they're not really interested in the company. In order to protect the future opportunity, they don't always give the best honest feedback, and that hurts the founder.”

“So if you're the founder and the deal time is really, really tight, and you feel like you need another two hours to spend with the partners at the three funds you're thinking about working with, you have all the leverage. I could see the allure of just rushing…”

“When the founder is successful, the company is successful, and the venture investor is successful. And it happens in that order.”

“Take the decision and own the outcome of the decision. Your board is giving you advice. It probably sometimes feels like because everyone on the board is often more experienced than you or has had more success to date in their career, that what they say is wha…”

“I think that the best VCs, especially in the M&A process, can act both as a balancing and a calming factor for founders. It's an incredibly difficult and challenging task for a founder to sell their company, whether it's big or small. There's just a lot going …”

“Without being on the other side of the table, without shipping product, hiring employees, firing employees, I was not going to be a great board member, a great advisor to these founders.”

“As long as it is from your network, and as long as it's a very minimal amount of time, it ends up being not that distracting at all, so I would disagree with that. I think that there are a lot of top-tier investors that encourage their founders to do this.”

“I would definitely encourage founders to have a weekly or every other week phone call. Ours is 30 minutes. We often use 10 to 20 minutes. Sometimes we use the whole thing. Rarely we skip it, but it does happen, and it's just someone I trust a lot, someone who …”

“I think they should have a board from day one, and I know that's not a popular opinion, especially with founders”

“When you remove the founder from a company, the company almost always does worse.”

“I think that the art of fundraising and the art of pitching and the art of selling are all kind of bound up together. I just don't expect my founders to be experts in understanding the VC landscape.”

“And the other thing that happens in good deals is the founder frequently doesn't want you to do your pro rata because they want to give the new investors as much room as possible. So I found that there's an alignment generally in the good deals that, hey, stic…”

“Entrepreneurs want people who believe in their vision and have conviction around the same belief that they have. And if you To that entrepreneur. And instead of have them convince you go to them and you are already convinced and share that with them and offer …”

“On the financial side, I actually think people tend to undercount the value of exiting early to a breakout company, because if a company is truly breaking out and it still has a five or 10 or 20 X on top of it, then that magnifies the impact of the acquisition…”

“The other thing I would keep in mind is that people who tend to invest late may be good sources of capital later. And if they own a lot of the company early, they're just not going to participate later. So there may be some funds that you want to sort of keep …”

“So I actually have a diversity and inclusion side letter that I sign with my founders, and what it says is for every executive or board position, they'll consider at least one Candidate with a diverse background.”

“I think it's actually the hardest part of the job, because ultimately, as we touched on before, this is a services industry, and when founders come and pitch us, they're sharing their life vision, life dream. They've probably spent countless hours Ridiculous s…”

“Because the average expected return for founders of making a startup is sharply negative.”

“VCs know a lot about businesses in general and sort of have a lot of knowledge across many companies, but it's very broad and not that deep. And they usually know very little about your specific business and industry.”

“And so if you know an investor is actually interested in your company and is talking to you for the right reasons, being asked the question, who else is investing your round? I think it's a totally fair question. And on the investor side, like you really want …”

“You know, ultimately for founders, if you do exactly what you're told to do by your investors and the company fails, you're a failure. If you don't do what they say and it's successful, you're a success. So ultimately the decision is in the hands of the founde…”

“Find a disagreement with the founder before you invest, because your conflict resolution mode is important, and actually the person's reaction to conflict or to pushback is also important.”

“When you replace founders, you lose the magic.”

“But if they're trying to get you to climb up a tree and kind of make their ultimate selection based on a couple of million bucks of pre-money, that to me is usually a signal that you're a short-term optimizer and not somebody who's going to build an amazing bu…”

“If I look at my own 20 18, I think as a founder, I definitely went through kind of three stages of denial in terms of hiring senior folks on the team. And so the first thing I think you say as a founder is, you know, Hey, I don't think we need this role right …”

“There's actually a fair amount at stake for the recruiter themselves, because they have their own folk Rolodexes with high-quality talent, and unless you're doing a good job pitching the recruiter, they might not even want to pitch you.”

“If you don't see the world the same way, you don't see the future of the company the same way, there's no real way to build trust between the board and the founders, and that's a conversation that has to happen before any other, in my opinion.”

“The more you try and pull the wool over the eyes of your board members, not let them like into what's actually happening, that's actually what breeds distrust and pain and creates really difficult board conversations.”

“You can get to a point, at least in this funding environment, where fundraising isn't a problem, and it's just an optimization of who do you want to take money from, at what price, and which players are you getting involved, and you can get there if you build …”

“In today's world, the reality is that your business and your personal lives blend completely into just one person, and so I do think that In your role as investor slash advisor, you are a friend to the founder, and your job is to support the entire person with…”

“Almost 18% of the U.S. Population today suffers from anxiety and depression, but the studies have shown that for founders, this number is about two times higher”

“I think in many instances, yes. I think founders, with good reason, want a very fast process, and they want to get back to work, and are sometimes inclined, really, just to get the best deal as quickly as they can and get back to work. I would personally advis…”

“And I think for founders, they shouldn't always be raising, but they should only typically meet with investors if they're going to actually give them tangible business value, whether that's intros, customer intros, or prospect intros, recruiting.”

“You really can't expect to build a partnership with your Series A board member more or less in an abbreviated process of a week or two. Almost always what you need to do is sort of build relationships over the course of maybe six months or longer.”

“That was actually one of the big secrets of Y Combinator that if a founder frequently comes to their investors and asks, am I failing? That's almost always correlated and found in the founders who succeed because, you know, at that point you're actually asking…”

“Are the founders genuinely asking for the help and the partnership and the change has been initiated by them? Usually that is a very healthy sign that you can add a lot of value and that it's going to be a really positive integration.”

“And then likewise, we encourage founders to let us know in advance of any potential gotchas early in the process. We're likely going to find out about them anyway. It's always better to address them upfront earlier rather than later as surprises.”

“We almost always want the founders to stick around and work for Google after the closing.”

“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…”

“You shouldn't always be raising. It's exhausting, but if you're going to consider adding someone to your board, that person is going to be on your board for years, and if you're going to make that decision on the basis of having met somebody two or three times…”

“I think it is always smart to be spending five percent of your time on the relationship side.”

“Without sort of soft pitching people throughout a series of meetings and You know, you really don't get a chance to build that relationship and your chances of success are just so much lower. Whereas I think you should just always be building fundraising relat…”

“In almost every case, you will know far less about whatever business you're talking about than the founders who's in it every day and fighting the fight every day.”

“Investors first and foremost should do no harm. And I say that and people think it's kind of funny when I say it, but it's actually true. I've seen so many instances where investors are too opinionated and getting in the way, pushing founders to do things that…”

“When I started this business, when we started, we thought these would be incredibly difficult conversations, and there's no doubt sometimes they are, but oftentimes we find actually exactly the opposite, which is sometimes the founders are relieved after those…”

“When you're the founder of a startup, you are forced to learn things. The thing I forgot about that process is that when you're learning is actually mostly a painful process. And what I mean by that is it's mostly involves failing at things until you finally g…”

“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…”

“When you're fundraising, it should never be you convincing VCs or any investor to invest in the business. You want to find that investor that seeks you out and has so much conviction about what you're doing that they spend their time convincing you to take the…”

“So I really tell founders always that talk to me, but don't worry about dilution. Don't worry about cutting the right person in worry about making sure you have the best people around you in the world that can help you fulfill your dream.”

“One key thing though, that after a lot of reflection, a lot of time that I realized is that most people, they just want encouragement. They don't really want advice.”

“If you have to make a hard decision or have a hard conversation with your investor or your investor needs to have a hard conversation with you cannot let the friendship get in the way because this is a business relationship and you need to make sure that you h…”

“No, I do think they can. I know there's colleagues of mine who vehemently disagree with me on that, but I do think you can be friends. I mean, if you unpack what friendship means, it means respect. It means love for another individual. It also means honesty an…”

“Well, I think you can learn a lot about who you might want to work with by seeing if they actually do the work. And so it's a good first test of, you know, is this person going to be in the trenches with me? And are they going to help me?”

“Your power in the negotiation, it's driven by the alternatives that you have. So you want to go into your next fundraising with metrics that are so compelling that you're in control over who you work with and at what terms.”

“I think that there's a lot of incentive for the VCs to put money into a lot of different ideas with the hope that a one or two of them truly become businesses. But for the founder, you don't want to spend your time working on a bad business idea. And so you re…”

“I honestly think it's honesty and that there is no way that any founder who has not done this three or four times before can be a competent CEO scaling from seed to C and D and eventually IPO. And I think step one is just admitting that you need to hire and wo…”

“Founders should find both show horses and work horses.”

“VCs who ask founders to talk to their customers right off the bat, I tell the founder like, whoa, slow that down a minute. Like that's a bad sign about the VC that they want to go for the sanctum sanctum. Before they've even had a chance to build trust.”

“You got to go gradually. I call it the egg toss. Of trust. You know, that game kids play where you stand near each other and you toss an egg and then you stand a little bit further away and you toss the egg a little bit further. That is to me, the model is I w…”

“Our offers never explode, and we encourage founders to go shop our offers.”

“Founders often ask their investors, will you do your pro rata at the next round? It's, I think that's a dumb question because if there's a next round that's led by an outside investor, generally people are clamoring for their pro rata. To me, the better questi…”

“A lot of founders believe mistakenly, in part because VCs lead them on, that company valuation is some kind of a marker of how highly the VC rates your company.”

“We've got Atlassian, which is undisputedly a great company, but most of the stock is still held by the founders.”

“Generally, I would advise against doing so. I think it's great if you have opportunities to do so. And if you have the capital, when you have the deals in front of you, I think it's absolutely worth doing. What I'd advise against is splitting your focus too mu…”

“It's incredibly hard to be public about bad experiences, because as an entrepreneur, as a founder, you at some point will need to go back to market, and if you're viewed in any way as a risk, that just lowers the probability that you're going to get the outcom…”

“If you're simply asking an investor for a set of references, and sometimes you can say, can you introduce me to a founder that hasn't worked and a founder that has, you're still getting a biased pick there.”

“I think very few founders want the radical transparency of why somebody passed, and at the end of the day, a lot of the early passes are around teams.”

“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 …”

“And this is where we recommend to founders, like, look, you should raise somewhere between half a million to million dollars, which we think is the right balance between having enough to really be heads down and execute for, let's say, 12 to 15 months. But at …”

“As a founder, you have to know that all those things are available. It's really your job To extract it. I think folks get into trouble when they think that a lot of these things are these kind of marketing elements of a particular VC or particular firm are goi…”

“Being in the market and talking to a half dozen to a dozen investment firms in a regular cadence, I think actually can be quite helpful.”

“I do think it's better for a lot of founders at the earliest stages to have at least one or two of these micro funds who specialize in this stage or in a particular sector and who truly care that can roll up their sleeves and add value to the teams and be part…”

“And I think the first thing for a founder to have some security in a house, they're economically more efficient. They can pay themselves a lower salary. That's a good justification for doing the secondary.”

“It's okay if you have a fifty million exit or a hundred million exit. And most people around the world would say that is absolutely insane. But for the VC, that's not going to cut it. It's not going to move the needle. The math doesn't work. They need some muc…”

“I think that helps mitigate what is a new facet of the venture market, which is these shotgun processes where a founder tells you about a round that closes, you know, 48 hours after the first news of it.”

“Well, they definitely help with their network introductions and generally just being a cheerleader of what you do on a day to day basis. What maybe people are surprised, or at least my perception of what maybe they're not as helpful with is no one's going to k…”

“What I think is most helpful is when your investors are always looking forward because they're not caught up in the day to day. And many founders get so caught up in the day to day, their context switching, their racing between fires, that they sort of lose tr…”

“And so I think if I'm a founder, if I cannot answer clearly what technology inflections are happening that can be calibrated that I'm taking advantage of, I should either evaluate whether my insights powerful enough in the first place, or if I've just thought …”

“Being a founder is a little bit of a masochistic career path. And so if you're not a masochist, this is a great time to go do a job that like feels a thousand times better on a day-by-day basis.”

“So if I looked at the CEO or founder's time, 99% of their time is spent on operational issues.”

“And actually, if you think that it's a three-month crisis, it's better to think that it's six-month crisis. If you think it's six months, think that it's 12 months.”

“In venture, founders are customers, and the core loop is really similar. Evaluate, compete, and adapt. But when you're a VC, the product you're improving is really yourself and how you work with your firm.”

“You can never be too early or too excited to work with the founder. And at first I was nervous about coming on too strong or being too aggressive, but it's really not possible to oversell.”

“Over the last decade or so, a little bit of that Hollywood auteur mentality, you know, among directors has sort of creeped into the tech world, where founders like Hollywood directors want total creative freedom. They want final cut, and that's as it should be…”

“Founders need to be far more aggressive than what the average person might think. They need to have these traits of being visionary and pushing and being able to run through walls. And so just having a quote unquote sane level of crazy may not be enough, but w…”

“The reality is that founders are the ones who choose their board members more so than the other way around. It's really up to founders to decide who their board members are going to be.”

“Because if founder, regardless of my rights, if the founder asks me not to do something, I'm not going to do it.”

“So I think a lot of founders are a little too hesitant and blasÉ versus what they should be in this environment.”

“I sort of felt like I retreated into a shell, and that was a self-created and self-declared shell of, oh, other people can't understand me outside of me building a company because this is uniquely difficult or challenging. Which also isn't true, as I know now,…”

“You can do a better job as a manager if you're not operating from a place of fear, and if you can take 10% or so off the table and sort of cover your nest egg, if you will, or your ability to live in Silicon Valley, if that's where you're based, for example, a…”

“You want someone who's so deeply tied to their mission that they don't think about sort of the common logic of what's the best financial decision in the moment. And so that's why we look for that personality type in founders, because it correlates to this exac…”

“What I always tell my founders is, you should reply, and then you should get them to do work for you. It's very easy to send an email to an entrepreneur, but when they reply, you And they ask you to do something. I think that's when you can really shine both a…”

“If I look back at all the outbound emails that I sent when I started, and the founders that responded to me, and the way in which they responded to me, the ones that ended up being very successful, they responded honestly, they were transparent with their numb…”

“The incentives just aren't really there for VCs like us to sort of really say, look, you're just not impressive enough. You need to go work at a company, or do this, or do that for a few years before I really am going to be sold on this opportunity.”

“VCS want their same rough allocation, and that roughly means that a founder's gonna get hit with the same dilution if they're raising a million bucks, or five million bucks, or thirty million bucks, frankly, right? Everyone wants their 10, 15, 20, 25%, dependi…”

“Frankly, the number one reason I pass is the founders. I just, I'm not impressed by the founders.”

“I think where founders go wrong is where they might optimize for valuation over who's actually going to roll up their sleeves and work with them and support them.”

“But the reality is most people struggle in one way or another. And most Founders actually do struggle with, whether it's depression, anxiety, ADD, and actually the flip side of that, which is pretty interesting, is sometimes it's part of what allows them to be…”

“I would tell you, I think the way I would articulate the goal for you is you should Seek out to build enough trust from the very beginning with a founder where you are their first call when things are good or when things are bad.”

“COO is one of those roles where there's not like a single COO. It's very much a custom mold to what the CEO is and what the founder is and finding someone whose strengths are the founder's weaknesses and vice versa, more so than it is just Hire a COO off the s…”

“A founder who has zero net worth, and this is something that I've battled with in myself, you can find yourself optimizing for a year from now and not thinking about 10 years from now because you're optimizing for today.”

“So obviously there's the press element and things like that, but to us, it's a red flag when a company's like, hey, can you just like post us on social media?”

“Even if I have a sales guy who is better than me at selling, he'll never have quite the same impact as the founder of the company showing up. So sometimes you've got to show up because the customer wants the big man to show up.”

“I think founders skip steps. They skip steps because they are looking at perhaps headlines or someone else as an example, but they don't dig in to see how that company that they like so much got to where they are. So I think there's an element of research and …”

“And that's one of my key criteria with founders is does this person need to create a big company? Not just want, but need to, which will create a persistence that follows through their entire life almost to build and create companies.”

“And I do believe that parental instability or home instability leads to a situation where the smartest and most interesting founders who are strong enough, I would add, sooner or later learn how to master chaos because they had to survive in it.”

“Most of the great founders that I've met, they will listen to the data and act differently. And they will also listen to you, but they'll take your input into account, but they're not going to necessarily do what you want. And I haven't found them to be partic…”

“You want to go after the founders who just want you out of their way. They don't want help. They don't want coaching. They basically want the money and they just want you out of the way.”

“One of the advantages investors have is this bird's eye view where they can help founders identify, you know, the two or three most crucial elements of the business that need to be addressed.”

“I don't Google search people before I meet them. It's a hard and fast rule for me.”

“The first question I ask every single founder is, tell me their story. Like, not the business. I don't want to hear about the business. I want to hear about how they got to where they are.”

“A lot of the times I make up my mind about the person before ever hearing about the product within that 1:10 minutes of them telling me their story.”

“Is that you should not waste too much effort on it and try to always make them a learning experience or draw some other use from them because otherwise you just spin your wheels a lot.”

“So if you don't feel confident that you can evolve through your team, then definitely consider selling.”

“Leverage is helping a founder or CEO get something done faster than they would have without you. And overhead is making them get it done slower than without you.”

“The conversation usually with them is a, what I would call like a private one-on-one of, take your sales hat off, For a second, take your hype person hat off. Cause as a founder, you know, you're selling every single day, whether it's to recruits or customers …”

“Really interview the person you're working with. These people are going to be with you forever. You should really want to get to know them, and it doesn't mean you get to know them by telling them about your business. Ask them about theirs. Ask them about thei…”

“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…”

“You get a lot of founders who do fantastically early on, and they don't know how to scale past, like, 40 people. They still want to be overlord. They still think their opinions matter more than everyone else.”

“I think it's important to reward and to praise people when they come to you with information about mistakes.”

“Is that when you have more VCs in the ecosystem, you actually do get more innovation, which I know is against what most VCs think, but we're actually seeing it play out in our data that when you have more people writing checks, you actually end up getting more…”

“I think almost every company you look at, they go through this phase shift when the people who started the company kind of detach and either exit or no longer involved. The company becomes a different company. It becomes very good at execution, but it kind of …”

“And so I fully expect in the next five, 10 years, more founders to consider that route because it was not something that I had heard of and not something my board had heard of, but we just looked at it from the ground up and dissected it and ended up feeling r…”

“So angel investing absolutely is a distraction. I think if you as a founder, like run your own like seed fund and raise capital on the side while you are building your own product and business, I think it's a massive distraction.”

“I think anybody who's trying to do something that the world has never seen before or trying to work with people who've never, they better be coachable. Because you're going to be so narrowly focused. You're going to be so heads down. You're going to be on a mi…”

“So many founders spend so much time engaged in the fundraising process. That is a huge mental and time investment that you have to commit to, and so for us, we never had to do any of that. That all Was founder energy poured right back into helping our customer…”

“And I think one of the ways that board members can be valuable is just talking people through, because it's very rarely as bad as you think it is, and also very rarely quite as good. As you think it is, of course, and being sort of a stabilizing force can be e…”

“So if I'm getting as much money as I want at a price that I want from a person that I want, it's a no brainer. You take the money.”

“Once the company is off the ground, the less a founder has to worry about their day-to-day life, the better. And if taking some money off the table enables their life to be easier to balance with their work, so they're not stressed about their living situation…”

“So if I'm going to take a three million dollar check from you know that you're in the bottom quartile of money allocated from that fund. So assuming that you're going to get this magical attention allocation from the fund is a mistake.”

“I think the bigger challenge today, to be honest with you, Harry, is less around price. It's more on how quickly decisions are having to get made, and I think that, I think, might have, you know, negative implications, not just for investors, but also for foun…”

“I think in the earliest days of the company, in the formation of the company, you know, as you're building the product, I think you should be thinking, What are the economies, the extensions of our business that we can invest in that will have transitive prope…”

“I don't think people spend enough time on the vision. They'll say, like, if you ask somebody, what is your vision? 10 to 15 years, where do you want to be? It's rare that somebody will be able to, like, recite a, like, really tight three to five sentences of e…”

“A significant majority of the founders, we've backed our investors in Ribbit, which means a lot to us.”

“Our best founders come through recommendations from our existing founders.”

“I do believe something which a lot of people get angry at me for, and it's that the best founders do not need VCs to help them get talent.”

“So the lesson there was whenever a team is amazing, but there's something that you don't like. So make sure that you follow up and you stay close.”

“Founders like the idea of M&A, but In many cases, what they'll do as they kind of unpack M&A and do due diligence is they'll say, you know what, actually we can build this ourselves. We don't necessarily need to buy it. And so I've just seen this too many time…”

“What a lot of product leaders make a mistake of, as well as growth leaders, is they think it's their show. They get to create the vision. They get to create the strategy. And it's like, not really. You're there to execute on the vision and strategy of the foun…”

“I believe, for example, that it's founders responsibility to come up with original hypothesis for growth model. And then everybody immediately goes into, I need to hire head of growth. Wrong. Because you need to hire a settler. You need to hire a settler that'…”

“No one ever skips around. You spend the money and you're back out in market on the exact same schedule you were if you raised Half as much money.”

“So I think one of the best things you can do as a founder in this environment is raise a lot of money at a very high valuation, but don't use it, or at least don't spend it faster than you would if the money had been much harder to raise.”

“One of the things that's different between now and 20 plus years ago in particular is there's a lot more secondary going on, which means that founders are taking capital off the table in a lot of these rounds.”

“Well, realistically, 90% of startups fail. So the 10% that are successful just In their own right, you know, have achieved something that's unrealistic. And I think too often feedback loops that are given to founders are to be realistic as sort of a criticism …”

“If there was one thing I would change, it's the us versus them attitude between founders and VCs. It's, I touched on this just earlier. I think it's just false. You know, it's an unhealthy, false implication that these are two different species, or that the go…”

“So the founder needs to sell the product before anyone else can. So day one, founder equals head of sales.”

“They wait way too long to hire revenue ops and sales enablement teams to make the team successful. So they invest all this time and money Into hiring a sales leader, maybe some sales reps, and they don't have the support systems to set them up to thrive and sc…”

“I think bringing in a sales team often probably should have happened earlier than founders anticipate.”

“But I think it's hard sometimes to hire your head of sales at that point, because you may not ultimately know who you're going to wind up selling to as you get to more and more scale and different sales leaders spike in different areas. And so a mistake that f…”

“Founders underappreciate the fact that sales is a skill, just like writing code is a skill. And so they often, I think, maybe hang on to that role as the initial salesperson, maybe a little bit too long before thinking about perhaps I want to bring in somebody…”

“So a few mistakes founders make hiring PM. One is assuming they're like a great PM because they've written amazing blogs or tweets or done podcasts, like myself included. It's a lot different to do the job than to be talking about it.”

“And one of the best books I love to have founders read about leadership is not a business book, but a book called How to Talk So Your Kids Will Listen and Listen So Your Kids Will Talk.”

“The founder sets the bar on the type of sales culture you Caring, competitive, cutthroat, combative, whatever culture they want to infuse and instill, they're the ones that set that culture, that set their sales go to market.”

“One of the best books I love to have founders read about leadership is not a business book, but a book called How to Talk So Your Kids Will Listen and Listen So Your Kids Will Talk.”

“Without question, it's better for founders. Much of the collaboration in venture did not benefit founders.”

“Founders don't do any diligence, right? Like, they just decide if they're great.”

“The first thing you've got to evaluate is, is this person that's sitting in front of me Capable of the emotional, physical, and mental stress that it's going to take to build a business. Binary. If they're not that person, regardless of how good their idea is,…”

“There's a limited amount that I can bring anybody, but I can bring an enormous amount of people to you as a founder who have skill sets or relationships or desires to help you.”

“It's a hundred percent about the founders. Not 99, it's a hundred percent. Forget about markets, forget about TAM, forget about even other co-investors. Myopically focus on your relationship with founders in choosing people who are going to build the next gene…”

“That is both your superpower and your greatest weakness, which is like, you can believe you can do anything. You think all your success is because of you. You think you're some unique animal.”

“That, you know, that it's all about being the best alternative for the founders. The founders are the customers, not the LPs. And the customer's always right. And we work for the founders.”

“When you start growing past your, you know, 20 people, There is so much work to do product management, right? You need a person who's at least one person who's the voice of customer watching over all of this because as a founder, CEO, leader, you have so many …”

“I think the most classical mistake is actually not in Making hiring mistakes, but in making the mistake of waiting too long to realize you made a mistake, right? Like that's in my experience, the way harder thing.”

“No founder calls or founder meetings at all. Even pre-investment, even during the decision process.”

“So my advice, and this is going to sound kind of paradoxical, is founders should put off the second product for as long as they can, but not forever.”

“No, the founder shouldn't and it's better that, that they're not. So of course the founder is the most, most often the first seller and most often you know, and they need to link the sales playbook to the vision of the product and the company they want to buil…”

“But I think the relationship with the founders matters a lot because that's what we're in the business of doing is backing them and, you know, backing repeat founders. Company number one didn't work, but company number two might be a blockbuster.”

“And right now it's such a confusing time for these founders, right? We told them cut costs during COVID. It's a recession. Who knows? The demand is gone. Then there was money flowing through the system. Money had never been cheaper. It was all about growth. We…”

“Busts are psychologically impactful far more than they're financially impactful. It takes people a long time to realize you're in a bust, and then even longer time to come out the other side, and that's true of founders.”

“So I completely agree that the highest leverage activities you can do as a founder is hiring the best bench and C-suite and VPs you can. Setting the vision. That's only something you can do, you know, finding the values and the purpose of the company or missio…”

“You do need to give them some time and, you know, also founders, I would say suck at giving feedback. There's many reasons why For some days it's hard to give, you know, constructive feedback to senior leaders, but you do need to give them feedback to talk abo…”

“I think with founders, actually, for me, the best founders have the ability to move from the 5000 foot meta vision to like last Wednesday's Facebook ad spend and how it converted.”

“I think we probably fall more often on the side of continuing to back businesses and sometimes those are the best decisions we ever make, and sometimes they're the worst decisions we ever make but Founders and companies will more often find us leaning on the s…”

“They should actually treat the process of going public as much as an exercise of trying to put off the wrong kind of investors.”

“I'd kind of call bullshit on the founder can't create it. Like, if you raised money, you started a company, and you have the capital to hire anybody, you're in sales. So you've already created that sales pitch.”

“I think a hundred percent, a leader of an organization, a founder is accountable for that V zero of that playbook.”

“I'd kind of call bullshit on the founder can't create it. Like, if you raised money, you started a company, and you have the capital to hire it, you're in sales. So you've already created that sales pitch.”

“Also, by the way, it's really important for that founder to document who you're not trying to solve the problem for, because that's going to be a direction of how you actually focus the sales team that you go and hire.”

“In either case, whether you're competent with it or you don't feel highly competent with it your involvement as a founder is extremely necessary, especially for an early stage product.”

“They overemphasize background, resume, titles, and companies that the executive has worked at and they often ignore their instinct about the executive during the interview process and then unfortunately, end up regretting the choice six months, 12 months down …”

“You're still gonna spend 25% of your time with customers, right? Or prospects. Like that's not gonna change. That's not gonna change for six or nine months.”

“Corporate venture capital has been an utter distaste and a success and founders hate it because, you know, the interest of the company that's investing in the interest of the founders diverge.”

“When you release a podcast with a founder, you should also send it to every investor on their cap table. They are incentivized to share it. They have shares in the company. You should also send it to their board. They have a deep relationship with the founder.…”

“I think this is a downside of a lot of founders. We assume that the whole world is obsessed with whatever they're building, when in reality, like, they have to go through carpool, and pick up kids, and put food on the table, and do all these things”

“And the ones that don't do it well are the ones that really view this as out of the money call options. And if the opportunity presents itself, we're going to try to get sharp elbowed and box out other groups. And I've yet to see that really work. It might wor…”

“That's not their job, I believe, to create the sales playbook, but it is their job to generate the inputs That go into that playbook.”

“You certainly need to make that trade off at some point, but I think most founders do it too early. They think they think like, oh, we have a product that like shows some glimmers of, you know, product market fit. Let's go hire a sales team. And that will be t…”

“Founders tend to be, have one category where they're extremely spiked and a lot of other categories where they're just like really abysmal. And, you know, founders that basically find that, you know, something to build or something to do that, you know, really…”

“The sort of media view of like founders it, it's sort of like, You're either a superhero or a supervillain, and there's only room for those two. It's like you're, you know, and there's such a like, You're either, it's either like saint or super villain and the…”

“Market is the single most important thing. If there are externalities that can kill a company that you can't control, no matter how good the founder is, it's not gonna work.”

“I'm not being a good friend to the founder if I'm blowing smoke up their ass in the boardroom, and then the second they walk out of the boardroom, all the investors have a different conversation. Right? So I think that being willing to tell the truth as I woul…”

“If a good manager meets a bad business, it's the reputation of the business that remains intact. I think the same way about a market. If a really good founder goes and tackles a really crappy market, that market's still going to be crappy.”