The Wisdom Wall

“and, uh, the single most common feature is a broken relationship with their father.”

“I work with many, and when they actively manage, they do not get the right decisions. They push managers to do things they shouldn't do. They push them to go enterprise before they should, push them to do more products, push them to scale faster, take more cash on because they want markups. I think you want passive.”

“the greatest founders that I know are motivated by the internal fire and being in London. I push myself every day to be better. Yeah, everyone around me is relatively mediocre in terms of London, generally speaking, generally group population wise. I didn't need them to feel for failure. I will push myself and the best…”

“I don't think it matters if your product is better anymore. Boom. Whoa, hot take, Harry. Distribution trumps all.”

“There's a reason why I would never hire them or invest in them. Those guys are the ones that break the minute something breaks. They never ever have experienced being bullied, being the fat kid in the corner with no friends.”

“The best actually strategically lent out of their best positions, and so I think we'll see a movement away from the momentum, portfolio management, liquidity management doesn't matter, to actually the best returning managers being incredibly disciplined around core tenants of portfolio management, especially liquidity…”

“I lost money recently because, um, I invested in a company And the founder was world class. Fantastic founder. But in a market that, hell or high water, you could not make money, and then the business was no longer able to exist. And I learned, actually, market wins. Whatever anyone says. It's not, it's not primary…”

“Do you know what I think the biggest, most broken thing about LP worlds today is? It's the incentive structures for LPs. I'm speaking to a lot of them who are investing in the biggest brand names, and we don't need to name them, and they have the most egregious terms. And I'm going, what you need to return in terms of…”

“Which is actually, most often, it is boys, um, and it is boys' relationships with their fathers, and it is a broken relationship with their father where they're trying to prove to them that they can be something, they're worthy, and that is how it most often manifests. Very rare is that anything to do with mother.”

“If you're Lagor or Harvey, dude, you've got to go into Cooley or Clifford Chance or any of the, build relationships with fifty-year-old white male partners who want to play golf and be told that they're great and that You know, life is awesome. And then you got to do deployment to junior lawyers who don't want to…”

“tier ones are worth it. Take a discount. They will help you get a next round unwaveringly.”

“The amount of great operators who you're like, well, they wouldn't be, I'm so, I don't mean this rudely, dumb or naive enough to just join a company because of a VC. Do just join a company because of a VC. They'll go, oh, it's a Sequoia-backed company, oh, it's a Founders Fund-backed company, it must be hot.”

“The truth is true product market fit Is so unwavering. Any question of like, oh, do I have it or not? If you have it, you fucking know.”

“you should aggressively chase making your first million more than anything else, because the hardest to make is your first million by far.”

“my, my business partner always tells me very correctly, life is like a, a cooker in a kitchen. There's four hobs, you know, that you turn on. There's family, there's friends, there's work, and there's fitness, ok? Family, friends, work, and fitness. And the trouble is, you can only keep two on at the same time, and so…”

“there is a world of trade-offs, which is like, I cannot sustain growth, focus on margins and improve them, move into enterprise, or sustain it and make it super happy. Oh, and continue to focus on beautiful product quality all at once.”

“capital concentration limits are the enemy of great venture returns, and that's why they have 33% of their fund in Airbnb.”

“Silicon Valley has dialed up the intensity on company building, and if you want to build a ten billion dollar business today, you simply have to be willing or really to work seven days a week, like it or not.”

“I always start, like, dating someone, I'm like, listen, number one is my company. Always. Always. That is always how it's gonna be. And I think you have to if you're gonna build a ten billion dollar business.”

“I see these deals every day in SF, Rory, and they're 400 K in ARR. That's not product market fit.”

“The only thing that matters about culture is that you have momentum. You're moving forward and that you're successful. I've never met a really successful company with a shit culture.”

“Longer hours leads to more success. The harder you work, you just are, like, more likely to be successful. Some people disagree with that too. Oh, you're more strategic if you have more time off. Bullshit.”

“one of the most clear signs for me of an exceptional entrepreneur is they always start early. They always sold Nokia mobile phones on eBay. A lemonade stand at school, you know, whatever that may be. You never came out of McKinsey or Bain and made your first entrepreneurial project.”

“I have a simple rubric for exciting business. Low competition. I find it hilarious the amount of people who want to go up against the Collison's or Toby at Shopify. Are you kidding me? You want to, you chose the Collison's as your weak competitor? Terrible. So low competition. One, legacy infrastructure of existing…”

“company values, you should, I'm sorry, I'm gonna jump in here. You should be for or against them. You know, we, fairness and honesty. If you're not in for these, then obviously you're an immoral person, respectfully. What are you in for? Unfairness and immorality? Like, I, my values are, this will be the place where…”

“actually, regardless of how well the company's doing, regardless of trajectory, who's joining rounds, if you are in early enough, and the prices get high enough, just take some off the table. And actually be much more active around it. Like, you know, be a real manager of your portfolio. Not a passive investor.”

“For founders listening to this, wondering if the check size that the fund is looking to invest in their company is meaningful to the fund, a very simple heuristical question to ask is, what percent of your fund is this check going into my company? If it's under one or two percent, it really does not matter. If it's…”

“You are not a good enough picker at seed to only have 15 investments. You need a large enough level of diversification, and 30 is generally considered large enough when you run the maths.”

“if it's an early round, and the investor wants to invest in investment tranches, this is where they invest a little bit now, and then if you hit milestones, they'll give you more later. That is an investment tranche. Do not accept this either. This is completely wrong. It's bad for your business.”

“The other truth is I think there's a utility value to board members that resembles a barbell, which is like Fenton, Gurley at the A, um, you know, Alfred Lynn at the A, Roloff Botha at the A, amazing Pat Grady at the A, great, and then your pre-IPO people who are amazing for setting you up for getting on the public…”

“It is not in the interest of the founder for you, the lead seed VC, to sell your position at this time, but It is in your interest because you need to provide DPI to your investors. Very common right now. Core misalignment between founder and VC.”

“it gets to a stage with also fund sizes, Kyle, where it's almost easier to raise two billion than it is two hundred million, and the reason I say that is because there is a pool of LPs, as you know, the pension funds of the world, Who need to move a hundred million, can't get into Sequoia, struggle to move that much…”

“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.”

“If you take in a multi-stage fund at seed, they are not incented to price you up at the A because they're already in and they've got their ownership.”

“actually that was a technology inflection point with the rise of smartphones and the advancement of GPSs that led to some of those incredible companies, not the macroeconomic conditions.”

“I just think we don't think about the velocity of cash enough, and what I mean by that is like, you know, yes, there might be another double, but if I have to wait five years, and then the IPO, and then an 18 month lockup, Jesus, give me 50% of that now, and I'll way rather have the certainty and the DPI now than the…”

“I think richer investors make better investors because you do not worry about downside mitigation, but you focus on upside optimization.”

“You can't play growth with under a billion.”

“10 at four. I would be sitting in your partnership going, well, let's just like outcome scenario plan this. A forty billion dollar company or an eighty billion dollar company. I think you do 80. It's a 20 X with dilution. Traditional says 50%. It's a 10 X. We're going to turn the 10 into a hundred. Wow. Thanks for…”

“I also think very much like venture, you have to be either really big or really small in content. You have to be very natural, kind of teenager, putting their phone up on the side and hitting record, or you You are Logan Paul, or Mr. Beast, or like us of Vantures, studios all over London, it's much bigger. The mid-tier…”

“Fundamentally, there is intense uncertainty around what Anthropic and OpenAI will do and who they will kill at the application layer. And so in a world where we desperately seek certainty, we look for validators, and the validators of someone being a math Olympiad or you name it, whatever that is, that validation, In…”

“Great CEOs are motivated by one of two things I found. Either the fear of losing, or the thrill of winning.”

“I've never, ever not seen a young founder not fall for big logos. Ever.”

“And bluntly, I don't think great people need that much management. Vacation monitoring is not something that great people need.”

“the biggest lesson I have in 10 years of investing is you have to diversify to concentrate, and it, actually, what I mean by, I should have invested in everything, and I should have done, to find The Alan Changs, the Adam Ferogis, the Cliff Weitzmans. You have to be broad to have the luxury to really know.”

“when they push on title, They're bad. When they push on salary, they tend to be good and know their worth.”

“visions are the most actually constraining thing that we force founders to try and articulate.”

“What people don't see is the 10 years of relationship building before that, but the most important lesson from that, actually, is I always want people off email. Get people off email. People want to work with people who they like”

“And it's a great way to pre-sell to have content as your relationship builder at scale.”

“At the end of the day, a partner's statements about someone will very often impact their decision. So whenever I go to a dinner or a drinks party or whatever, the partner of the person that I want to influence will be my best friend, because the power of the car journey home is what dictates what Simon actually does.”

“I do not think you can only have A players if you have a company over 250 people. By definition, A players are extremely rare if you want to keep that high bar. Post two 50, I, I don't think you can.”

“I remember he told me that price is a litmus test for your conviction.”

“when I look back on, like, fun one where there's, like, a meaningful timeline to actually look back on the six years now, the best performers, your linears of the world, were not obvious early, and the early out performers did not signify enterprise value in the long term.”

“I also think that you can tell your best and your worst within the first 60 days. The messy middle, you don't know. There's a TBD, but the ones where you're like, shit, we regret that one. That, you tell pretty quickly, and same with the god, they're on it. That first update, so well-structured.”

“when someone says alignment, take a shot, because I promise you it means that they don't really have the answer. When people know the answer, they're incredibly specific and use data to support their argument, I tend to find. And when they don't, they discuss culture and alignment.”

“Market size misunderstanding, misestimation is the single greatest reason why great investments are not made.”

“if someone is giving help, they need to feel like you're the subordinate, like you are in some ways beneath them. So I would always start with this position of almost vulnerability.”

“I know many billionaires. I know no happy billionaire families. I know many more poor people. Much happier.”

“if you want to invest in the next, uh, Helsing, don't. Just invest in Helsing. I, I spend my life with investors who are like, oh, I'm trying to find the next OpenAI, the next Android. Don't. Just put your money in the winner.”

“The challenge is in today's world, you have to break most rules, and it doesn't mean that you're a cowboy and you're gambling, but it means you're much more elastic than the more concrete investor mind.”

“content is the most effective way to stay relevant without having to put dollars out the door in deals that you maybe don't want to do.”

“The cost of first meeting entry has gone through the roof, and so you cannot get that first meeting unless you've been at the pre-seed or the seed.”

“I say, actually, that the death of religion is the thesis for CPG and consumer brand investors today. And you're like, what? Thesis? Because we've shifted cult-like worshipping from God, Buddha, and these deus figures to High Rocks and CrossFit and Taylor Swift and Lululemon. And they are, ironically, in the minds of…”

“when you look at like outcome based pricing, it is impossible unless it is completely non-human in the loop, because otherwise there's always going to be this continuous debate.”

“you fit, like, all the characteristics of, like, successful founders that I have on the show. It's like, number one, made money early, number two, excelling gaming, uh, both very, very clear, um, archetypes.”

“Like, I think that's a massive problem, which is, like, people create values that no one can disagree with.”

“I think people demonize social in the way that diet can be demonized. If you go on my TikTok, Instagram, you name it, there's protein recipes, there's inspirational talks from Tony Robbins, and Alain de Botton, and great thinkers, uh, there's baby videos, I think baby videos are hilarious. I have curated a feed that's…”

“Well, I'm just like, there's two things that would make this fail. One is funding, and two is distribution, and the hardest is actually not the cash, it's the distribution.”

“Don't be afraid to do brand deals where you do get into brand names with tiny ownerships. The most important thing is that you align yourself with incredible founders and incredible companies in this new era, especially in this new era of AI, just get into some great companies.”

“I think your job as CEO is to kind of manufacture almost fake or small wins and to alleviate them into bigger wins just to carry teams through a bit stagnant times.”

“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 growth at Revolut is a better angel than this random person,…”

“And actually, it takes out the whole segment of young people who are incredibly tenacious, ambitious, hungry hustlers, who of course they're not as good as me. I've been doing this for 10 years.”

“I think values are very, very challenged when you can't take the other side.”

“don't have minimums because some people can be amazingly helpful with five K and so don't rule them out because of that.”

“those provisions exist for a reason, which is because in harder times, being able to get back one X, not 0.2 X actually across several companies, which is often the case makes a big difference. It can make a half turn on a fund.”

“I have a thesis that the best founders always and consistently start entrepreneurial activities very, very young. I never meet them when they're 25 and it's their first thing ever.”

“Two, you either hate school or you love it. People that are okay tend to not be great. Really interesting, the binary is where you get great, and then also, like, ADHD is another, you know, as well as I do, clear sign of, like, the best founders have it.”

“write the same size check every deal. Like, everyone thinks, oh, I get different conviction levels. I'll write a hundred K check, and I'll write a 25. You're not that smart at pre-seed. Just write 50 K checks every time.”

“Why is, why do most companies stall out at, you know, some growth level at fifty million an hour? It's because the founder doesn't have a second act, because they can't operate a new geography, a new product, a new market. They can't get that second layer of the exec team.”

“What matters is being able to say I was a part of a winner and leverage the shit out of it for your personal brand to be able to raise your fund or get a job at one of the best.”

“traditional large sales teams selling three K ACVs and they say, ah, but you know, if we prove it and if we do this and this and this, then it'll expand to 30 K and truth be told, it rarely does.”

“It's unhealthy, but I think it's a necessity. It's like obsession is a necessity and it's very difficult to be obsessed and detached at the same time.”

“you choose your ICP. Start a podcast interviewing the world's biggest and best in that ICP. If I worked for you, this is what I'd do. You'd give me a segment. I'll start a podcast interviewing the biggest, I don't know, CHROs in software companies between 505,000 people. And now I have a reason to twice a week meet the…”

“you will have to do 200 shows, no one will care, you will not make any money, and then you will also have no proof that it works, still.”

“I think the difference between a two billion and a ten billion dollar business is a fucking great exec team and founder.”

“And the ACV is a 10 K and it's like, ah, and they're like, ah, but it'll scale. It'll scale, Sam. It rarely scales. And so we're layering on this enterprise cost base for this very SMB PLG revenue base, which has really been born out of the PLG motion. And I'm seeing a generation of companies have shit economics…”

“So I think visions are one of the most dangerous things that people can have. And that sounds very strange, but visions often underestimate your true ability.”

“It's why whether I'm hiring you or I'm investing in you, I will always go back to your early childhood. No great person who was hugely ambitious fell out of McKinsey and Bain and thought, oh, now I'm going to be really ambitious and courageous.”

“little and often is my secret to retaining great talent. And what I mean by that is you have title and salary, and I increase them separately, but little and often to create that kind of feeling of forward momentum more frequently.”

“if it's like early, early meetings, Don't send it ahead of time, because generally investors look for reasons to say no.”

“The idea that you have more conviction in one versus another at an early stage in particular, totally wrong.”

“one that I see is often the most successful founders moved a lot in early childhood.”

“I hate bouncers, I call them, which is, as you said a couple of times, five, six jobs. I'm like, if you're somewhere for a year and a half, and another for two years, and another for a year and a half, with ramp time and leaving time, You basically did six months of work.”

“Because I find with age, you understand nuance more. And when you're young, everything's black and white.”

“My biggest lesson from the last few years was actually just to sell at some points, you know, we were always told, lean in, lean in the bullshit. You need to lean out strategically over increments over time.”

“what's working often is unsustainable, and it's your sneaks, your figmas, your big IDs, which actually may take a bit longer. But you wouldn't allocate to them if you were doing it on traction.”

“If you resonate, if you have super horizontal product messaging, It's much harder to resonate with people.”

“I also think, like, share a voice is better when it's done remotely. Like, people don't feel as intimidated to speak up in a lot of cases.”

“In AI, access to proprietary data will be the single most important differentiator.”

“billionaire founders of funds, they can put in a lot more money than me. Doesn't mean they're more committed than I am.”

“And I say the opportunity cost of capital is real, which is like, even if you can make money selling software to restaurants, It's so freaking hard that actually there are easier places with higher upside to put that money.”

“my biggest is I've overweighted brand. I've seen that they've come from a big logo, and I've gone, they must be brilliant, and they're not, ah, very often.”

“I constantly feel guilty, because I constantly feel like I'm failing as a son, as a brother, as a boyfriend, as a fund manager, as an entrepreneur. There's so many different fucking hats. That if I'm winning in one, I'm by nature failing in another.”

“the most common I see with young founders is actually an insecurity in themselves of their lack of Experience, which leads to what you said earlier, which was the logo higher. They look for the Salesforce logo because they're aware that they don't have that experience.”

“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.”

“Lesson one, you don't have conviction at the early stage. Just do 25 K, 10 K, 50 K, I don't care, but same check size. Number two, you need 25. This idea that you're a genius picker, you're not. No one is. Five is not enough. You need 25.”

“I think the other one I see also is when they choose founders that need their specific help. So they're a B to B sales leader and they're like, oh, I could really help in that B to B sales engine. Doesn't mean it's a good investment.”

“One of my biggest lessons is when people are really difficult on the title. I want chief of staff, not EA. I want head of engineering, not VP of engineering or whatever that title. It's never a good hire.”

“I think follow on is actually just an inherently hard strategy, because it assumes that you can essentially predict your winners so much sooner than I think you actually can.”

“with young founders, they're much more volatile to swings, good and bad. And I find actually with respectfully older founders, Akin, that you're just much more tempered.”

“the rate of decay on operating experience has never been greater because of two things. One is actually, I think, AI fundamentally changes so much about Enterprise stacks. I think you could say the same for cloud actually in on-prem in some enterprise cases. And then two is COVID. It fundamentally changed how a…”

“I also think it's because it's the product and growth mindset that's inherent within a PLG-led org where it's product first. And it's so difficult to imbue that in an enterprise org. Oh. And actually tacking on enterprise sales into a PLG motion, not as hard as one thinks.”

“number one killer of partnerships is actually partnership breakups.”

“No, they can't. They cannot overcome political regimes. It does not work.”

“actually don't ever send the data room unless you're raising big, large funds, like, you know, Multi-billion dollar funds or your, you know, multi-stage funds, but generally speaking, because actually you have this paradox of choice where suddenly they give them 12 things in there, and they're like, ah, I'll get to it…”

“Now, the single biggest mistake I see fund managers make is they go out to fundraise with too high a target fundraise.”

“This does not prove you are a good seed investor, but it merely shows you have access to series B and series C investments. These are very different things, and actually can only serve to discredit you often, as it shows a little bit of naivety.”

“it's sometimes easier to raise a hundred million dollar fund than it is a thirty million dollar fund. Why? Because you unlock new tiers of LPs when you increase the size of your fund. More institutions are able to invest in a hundred million dollar fund than they are a thirty million dollar fund.”

“The biggest mistake I see early fund managers make is they go out to large institutional investors that they do not have an existing relationship with, and they spend three to four months trying to raise from them. They lose heat and They lose morale and enthusiasm, and the raise goes nowhere.”

“Consistently, the most helpful LPs for me have often been the smallest LP checks.”

“I think a big mistake I see a lot of people make is they get a big name investor in their fund, but that big name is also invested in 200 or 300 other funds, in which case, It doesn't carry much weight that they invest in your fund”

“they go to their priority names first. Do not do this. Your pitch both in delivery, style, and messaging will improve so much with each meeting. Start with a couple of investors where, respectfully, you would not be so sad if they said no.”

“Exit slides have no place in the slide deck. I do not see this so often now, but it really just attracts the wrong type of investor if they're looking for an exit on the day of their investment. It encourages short-term investment thinking.”

“If the chosen partner is slightly lower, just take it. Do not lose the right partner because of a small percentage difference. In price or size of round.”

“a massive mistake I see often, is founders who try to cram down all their angels to their smallest allocation so they can fit in as many as possible. Do not do this. Give less people More allocation. It's really important that the check size that you give them matters to them, so it's proportional. For some it'll be 10…”

“I really like it when they send, not slide decks, because they can just be used as like crutches, but like a doc, and then I say send it in a Word doc, not a Google doc, because if you send it in a Word doc, you write in isolation, because if, you know, you're much more engineering centric than me, if you make a…”

“You know one of the biggest bits of bullshit advice I think there is, which is like, oh, don't worry, no one really knows what they're doing. To me, this is complete crap. People do know what they're doing, which is why they're often where they are, and you should learn from them and seek them out.”

“If you have more than a hundred people, by definition, A-team is like the top one percent in my mind. You can't have only A-team if you're going to build a sizable company. It's impossible.”

“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 fundamentally do not believe you get to where we get to, unless you give up and sacrifice. I'm sorry, you can't have both worlds in my mind.”

“There are people who want to make it happen, and they want to see Kalshi succeed, and then there are others who fucking need to make it happen, and the ones that need to make it happen do the three all-nighters in a row and get it done, and the ones that want to are motivated on Monday and tired on Friday.”

“Do you know what I learned about, do you know what I learned about giving away secrets is that actually, even when you give them away, no one will pick them up.”

“So many people focus on MRR. It's not about fucking MRR. It's about seed expansion. Number of new projects. Like, your MRR is your output. Your inputs are what drives it. Focus on the inputs.”

“you cannot align your fundraise To macro markets, because six months time, it could be worse than it is now. 12 months could be even worse. If you need to raise, just fucking raise.”

“mine was most importantly that actually the market is more important than the founder. And what I mean by that is if you are in an untenable market, Even the best founder will not be able to get out. Like, truly untenable. Social, political unrest. Currency destroyed. One of these situations can absolutely tank a…”

“I believe the pro rata for your middle tier is never actually a great thing anyway. Like the messy middle pro rata, you're not gonna regret not doing it.”

“if you want someone who gets product messaging, Hire people who specialize in memes and gifs, because they know what resonates.”

“we don't want to grow users as much as possible. That's not a sign of product market fit. What is, is number of sessions per day, number of tasks created. I don't care about top line growth of users, but the tasks that they do to signify their product love.”

“I make people comment on Word docs, not on Google docs, because then they send them back to me the night before, and then I can pick on them in the meeting and say, hey, in the Word doc you said this, and their opinion is unencumbered by others, where it would be in a Google doc, and you see the real time.”

“if you increase the enterprise value of your company by one or two percent, you'll make far more than you will from this 5,000,010 million dollar fund.”

“I always actually slightly diminish the importance of kind of analyzing CAC at seed because it's so transient. It changes so much. It's so platform dependent. And really, it's just such an unreliable metric in my eyes, especially at this early stage.”

“You don't have unit economics. The CAC is going to explode, or you don't know where it's going to go. The LTV is going to shrink. We just don't know.”

“I don't think you should deploy capital unless you've raised capital in some way, be it for your own company or for your own fund”

“I always think like, you know, if the person's surprised that when they're let go, then it's the fault of the manager or the leader in that perspective.”

“Pat Grady said to me that never has the rate of decay on operational experience been greater.”

“Kent Goldman at Upside in stating to me that the best way to use pricing to your advantage is to use it as a litmus test. It's a leading indicator almost to determine your desire to do a deal. If you believe this is going to be a truly game-changing, transformative company, then eight or ten million pre really…”

“I remember he stated to me the importance lying in being Socratic, not didactic, knowing when's the right time to interject, and having 15 questions in your head, but having the ability to narrow them down to the two that are fundamental.”

“board meetings, I always feel entrepreneurs view them as a test, but they're really a chance for VCs to Provide their value.”

“Too many times I see people like combine a fundraise with a revenue milestone. Do not do that. Those are two separate PR moments that can be made into two big moments, not one.”

“I find actually, when you look at, like, the Collisons as well, they're real historians and truly great Founders are often historians of their sector.”

“One of the biggest mistakes I think I see with founders is like they're terrified of launching and not having any adoption. And so they make it a more diluted and diluted message for more and more people. It doesn't mean anything to anyone. And then they launch and it's like, it's the most mid product ever because they…”

“The thing I say actually on brand marketing is look for immortal assets, and what I mean by immortal assets is like, if you sponsor a podcast, make sure that the podcast has it in perpetuity.”

“especially when they're multi-stage funds, when there's absolutely no reason for them to ever kill optionality. Like, I want you to think that I'm amazing because in case you do inflate, I want you to come back.”

“if you need to educate an investor on the market, they're not the right investor for you.”

“So my biggest mistake is when I focused on market at all. All of my biggest mistakes in investing have been actually not really like, you know, losing money. It's been turning down great companies, but because I thought that I was smarter than the market.”

“We're expecting everyone to be full stack in every function.”

“I always want my main course to be someone else's dessert because like I'm going to care much more than they do.”

“Also, when you get spidey senses in the interview process, listen. Like, it will only get worse post-hire. What I mean by that is when someone, they just get the feeling that, you know, they really actually want to be an investor, not in finance. Trust me, when they get on the finance team of the investment firm,…”

“I think Sam Altman said it very well when he said, you know, older people use it as a replacement to Google and younger people use it as their operating system for life.”

“And I think actually trying to be a startup today, recruiting and maintaining that team in the Bay is next to impossible unless you have an egregious amount of money.”

“I always say do the same size check every time. Do not do the whole, oh, I think this one's great, I'll put 50. This one, I'm not sure I'll do 10. It's like, no, no, no, just do 25 every time, whatever it is.”

“Elad sent me and he was like, dude, this is amazing. This is amazing. Every time Elad sent me something and said, it's amazing. Just fucking do it. Do not think you're smarter is my takeaway there.”

“When we think about our entry price, do we think that we are able to three X that entry price within the next fundraising round?”

“And so at the end of every single email, I'd put, P.S. I know that Mackellan 75 is your favorite whiskey. I'd love to have one with you when you're next in London. The minute that you add that, you literally treble your chances of getting a response.”

“at the end of every show, I would say to people, hey, who are three people that you think I should have on that would be fantastic? And the minute people commit to three more names, I would say, hey, if I send you an email that you can forward onto them, would you mind making the intro? When people commit to the three…”

“if you have the ability to be miserable for no reason, you also have the ability to be excited and optimistic for no reason.”

“This is a game of who can survive the longest, and the lovely thing about content, Simon, if you fail, it's because no one cares, and if no one cares, no one will know that you failed.”

“very often you can just take something that works and make it 10 or 20% better. Oh, I love that cafe, but I've always wondered why they don't do really Instagrammable cakes, because the coffee is great. And the location is great. Why don't they do more? Making something 10 or 20% better is very often a great successful…”

“I love athletes, and I love investing in athletes, and the reason I do is because you are willing to sacrifice time and yourself for no immediate reward or gratification. It comes in the future, and you have to have this continuing belief that if you do do this, you will see the gains in the future without promise of…”

“I always say I don't care how long you take to get to a million in revenue, but I care desperately about how long it takes for you to go from one to 50.”

“for the first three funds, you know, there's no DPI, there's no DPI, there's no DPI. And then you return a shitload of DPI, and then LPs go, mm, but are they really hungry anymore? Cause they've made a lot of money.”

“If you want your children to give a shit about companies, buy them one single stock, because the minute you have any form of ownership, your interest level will go through the roof.”

“Seed is easy because it's Walt Disney versus Jerry Maguire. Walt Disney is tell me the story. There's lots of people that tell a good story and come from great companies. And then Jerry Maguire is show me the money. And there's actually very few people who are showing the money in a way that's actually true quality,…”

“Often you lose because you get the wrong entry point. You have the right idea, the right solution, but the wrong entry point.”

“never have a minimum check size for amazing angels. There's some who can only do five K, or, I mean, some are one K, and you can do that with angel or syndicates. Like, it's just as valuable, and often they'll give more because it means more to them.”

“I think this is the thing that everyone forgets with content, which is it takes two years often before you even see ROI come back at all.”

“The thing I find astounding with people who want to get into venture is, Actually, it's quite easy if you just give the freemium version of yourself. If I send you three companies every quarter that align to LeadEdge's model and the companies that you like, and I can see that on your website, and I do that for three…”

“I always say look for shutdowns, which is like, if you shut down a whole product division and the sales team are gone, that may not have been that they were shit. It may have been that the product didn't have product market fit.”

“a piece of content has to do one of two things. It has to educate or it has to entertain. Uh, and if it doesn't do that, then it doesn't have any place in any of our things.”

“I've interviewed 800 of the best founders over the last decade, and the single biggest commonality in the most successful founders is a high frequency of moving in childhood. You're forced to assimilate with different environments, different cultures, different people, make new friends, enemies, whatever that is.”

“I think the biggest reason why companies I work with don't find product market fit is founders get really nervous pre-launch. They expand the ICP too much, and then it doesn't resonate with anyone.”

“I find the second tier serial founders have had the multi-stage product before. They've seen that it's not all it's cracked up to be, and they actually go for the person the second time around.”

“The Tokyo test is, can you fly to Tokyo with someone and be engaged fully in conversation throughout the duration of the flight? And if you can, that is either the sign that you should marry them or start a company with them.”

“The biggest mistake that I see as an investor today, you know, with the investing hand, it's like focus on revenue and it's actually like actually seats per contract drives the total revenue size. And so the growth team should be focused on what product changes or growth initiatives can we do to increase the per seat…”

“I think notifications like social posts, which is very simple. Everyone must either educate or inspire.”

“After 2700 shows, I've learned that one of the biggest mistakes people make is they try and copy someone's style that's not, that's not authentically theirs, and think that's the right one. And actually, it's about finding where you are uniquely great in the three pillars of venture. Sourcing, selecting, and servicing,…”

“I actually like it when you find competitive athletes who turn into sports Reps and sales reps or salespeople. They can endure great pain for long periods of time for delayed gratification. It's like a core trait, I think, of sales.”

“I always think a ten billion dollar company needs a second or a third act, and I always say the difference between a billion dollar company and a ten billion dollar company is a founder who's able to transition between chapters.”

“I always say to everyone, hey, put everyone in support for two weeks minimum. Just hear the pain points. Hear what they want. Hear what they don't like. Just hear everything. It's the best way to do it.”

“I think it's because VCs sell cash. And so you have to get, you have to get really fucking good at selling. If it's like one dollar, one dollar. Well, my dollar is prettier than your dollar.”

“So many of the great investments have been missed because people say, ah, but they could build it themselves. And they so rarely do it.”

“I always want to see an entrepreneurial mindset super early because it's the biggest correlation with future success.”

“One of my lessons is when someone really great brings you into a round, don't ask twice.”

“And I think, you know, the best companies in the world will actually be defined by their ability to transition between models.”

“can you imagine like a chef in a restaurant where 90% of the meals they produce can be terrible, the worst. As long as 10% are great, you are, you can be the best in the world.”

“it is the most effective thing that I urge all founders with sales teams to hear the pains of customers. You hear, you speak about training empathy. It's probably the closest way to train empathy, just to listen to the customer support.”

“The real pattern is the best founders say, are you kidding me? Here's 10 things that are challenging me, and I'm terrified about them, and I'm like, okay, let's go through them one by one.”

“I, I think little and often is my biggest lesson. And what do I mean by that? It's like break apart, like title and then salary or finances and then increase one of them little and often. So they continuously have hits. And this is like once every six months, continuously have hits of progression, financial or career.…”

“the biggest problem with content teams is they build no verticalized knowledge in each channel, and so they just work across all of them, and they're like, okay at all of them.”

“the best managers are not going to meet you for a million dollars if you're, if you're not.”

“when it comes to like sales pipeline in particular, share a Google sheet with the companies that you want to speak to, the specific person within the company, hyperlink, hyperlink their LinkedIn. So it's super easy for me to go. Oh shit. Actually, I do know three people with him. And then also say like, hey, put your…”

“being in the industry, there's kind of two functions or two types. One is like the research person who is just incredible depth and analysis, post meeting, benchmarking, landscape analysis, you name it. And the other is outbound sales prospecting. We can't miss anything, be it all the drinks parties, be it all the…”

“People often just don't have product market fit, and they're like, I need a growth advisor. No, you need product market fit.”

“one thing that I will ask is, like, tell me how you first made money. And that always shows, like, true entrepreneurial grit.”

“I find that the best founders that I work with have a hobby that is just very unusual.”

“A truly differentiated model, be it on the servicing side, be it on the sourcing side, you have to have two of the three to be successful in this fundraising market.”

“if a fund today is three, three hundred million, and the manager wants to scale to two billion over the next three to five years, They might not be aligned to your long-term financing interests.”

“If you have super horizontal product messaging, It's much harder to resonate with people.”

“whatever time you spend creating content, you should spend the same time or more distributing.”

“Often it's revenue and revenue for me is an output. It's not an input.”

“a lot of endowment funds get fresh buckets of allocation in the start of any year. And so Q one is actually optimal. Q three is probably the worst and actually end of Q four when they might have like a spare little stipend left. Can actually be the best as well”

“the one thing I think does make a difference is when you have partner churn at multi-stage funds, so if you can be orphaned at multi-stage funds, even if you do well, if there's no real owner, it can be a lot more difficult to have your internal champion to lead the A, I find.”

“I think the other thing that people forget with VCs is we think in increments, people often think they want to see like the twenty billion dollar outcome. And yes, we absolutely do, but we also want to see where the next round comes from.”

“rule number one, uh, never say philanthropy to an investor in a pitch deck or around.”

“If you have not worked together as a team, the LPs that you are raising from will inherently view this as a massive red flag and label it team risk.”

“An LP will never want to be more than 20% of the LP dollars in a fund, and so the size at which an institutional LP would be interested is when you raise twenty-five million dollars plus at the very minimum, and then they can invest at least Five million dollars.”

“LPs invest in lines, not dots. Especially for institutional LPs, it is so rare that an institution will meet you and invest in you without an existing relationship, and without having followed your work before.”

“Place even more weight on their recommendation if the company has not been a success. It is easy to be a VC champion when the company is flying. You often see the true colors when a company is really struggling or fails.”

“if you're doing a Zoom call and it's a first meeting, do not have more than two people on the call from your team. It makes it tough to really get to the core of the discussion, and removes a lot of the relationship building with Too many people on a call too soon.”

“I would have asked for a deck pre the meeting, and I as the VC should have gone through this beforehand. That's really my duty as a VC to have done the work beforehand, and so in the meeting we can really spend the time to double click or try and expand upon more that I didn't understand when I was going through the…”

“For example, if the check size they are investing is less than one percent of their fund, It's not that meaningful. If it's less than .5%, it's really not that meaningful. Now this could be bad, as it means that they are unlikely to be able to provide you with the same time and attention they would larger checks.”

“Rule of thumb, never raise less than 18 months. You also do not... You also do not need to raise more than 36 months. If we plan for a six-month fundraise, and the fact that execution 99% of the time always takes longer than you anticipate, I always choose 24 months as a runway guidance to raise for.”

“It's literally harder to remove an investor than it is to get divorced.”

“14 days is perfect. This is enough time for any VC to do the work they need to do, but also if they cannot do it in that time, without a plausible excuse, it's unlikely they would have done the deal anyway”

“when planning your angel allocations, I always advise founders to assemble their angel cap Table as they would a sports team. Each person has a specific position which they are specialized to and have a world-class skill in. So you have someone for marketing, for hiring, for PR, for partnerships, for entry into…”

“In preparation for the next round, the most important thing is investors invest in lines and not dots, and so I would sit down with your new leads and align in that first meeting on five names that would be ideal leads for the next round, and then also clearly break down the milestones that you will need to hit”

“I think if you don't send the updates, then you're halved in terms of re-commitments for next round.”

“Like, your job as a founder is to fund, hire, and expel the mission.”

“in venture, it is one of the only asset classes, I believe, where the asset chooses the capital. In all others, the capital chooses the asset,”

“When people send cash back, they feel obligated to then return cash back for the next funds. It's very difficult for the LP to be fair on them. To get three X funds returned, and then go, thanks Kyle, not coming back for the new one. It's very hard to do.”

“the speed of execution is one of the clearest signs that I see in companies that I invest in that work well.”

“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 believe that actually you have what it takes. Because they…”

“Content takes six months at a minimum before you really start to see much ramp at all.”

“The biggest mistake I see so many make is they are too broad in the content topic they target. Entrepreneurship is far too wide. Tech news. That is not going to do it. You have to be specific.”

“You will always underestimate how much people appreciate feeling like a part of the content creation process, and how much they will share it when it goes live if you make them feel part of it.”

“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. You should send it to the C-suite of their company. They…”

“Remember, people will not likely share on all of the requested. They will only do the top one or two.”

“For every hour you spend creating, you should spend the same amount of time distributing.”

“when working with other people to create content, when you interview them, when you feature them, the single most important thing is to make them feel safe.”

“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 the biggest thing that managers miss is they say that I need more, I need more LPs. And I say, well, go to your existing LP base and say, can you give me three names that you think would be really well aligned that you will vouch for me to. And people don't leverage the existing that they have to get net new. I…”

“that's why I always advise managers to like put in place deadlines that are not like tomorrow or next week, but like two to three weeks out, because if they're not going to make a three week out deadline, they're not going to do it.”

“No, listen, I'm actually with you, and I also think it's much easier when they bring their team than when you kind of throw a head of sales with an existing team that they maybe didn't craft and create, and there's that friction.”

“brand is a hack to track, and what I mean by that is when you don't have track, you gotta have something, and brand is that shop sign that is a replacement for track in the early days.”

“show the freemium version of yourself. Like, choose five VCs that you want to work with. Like, all of our portfolios are very public. Understand the type of deals they like, and for six months, send them three deals every single month. And after six months, Dina, you would probably hire them.”

“Every single investor has underestimated just how big their winners can be.”

“I also think like focus on a niche in the early days, like find a hundred people who love it and it could be building cohesion between product design teams and customer support teams and just tweet about that, but make them love you.”

“Market timing, I'm not smart enough to predict it. The product is transient. So all I've got in front of me is Scott and Mike and Jay, and do I fundamentally believe that whatever may happen, they might be the ones to guide it to where it could be.”

“Kind of your fund size is your strategy as well, and so that's always very much front and center for me.”

“I think the operating also makes me a lot more skeptical and negative as an investor, which is also an interesting lens to adopt.”

“Uh, they all have kind of data sourcing tools, and so when you have inflections in, in growth charts, in retention rates, in employee count, they all get notified at the same time.”

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

“And then just with the content, fundamental to choose immortal content platforms, so Snapchat for content isn't really great unless you're looking to create connections. It dies and is not searchable. The likes of Jason Lemkin have done incredibly well with Quora because it is immortal. You can search for it seven…”

“and Dustin Doggan at us says, can a capital is a crappy differentiator? And he's right. Um, you know, your money is the same as mine.”

“he taught me, you've never won or lost. You're only ever ahead or behind.”

“Think of someone who you deeply respect and admire and you want their life. For me, it's Pat Grady at Sequoia. Three reasons. Great father, great investor, Great husband. And whenever I'm faced with a tough decision, I ask, what would Pat do in this case? And it generally always leads to me to make the right and…”

“So I'll say, what would Mr. Beast do if he was running our product today? And then what would Johnny Ive do if he was running our product today? And from the same person, you will get multiple different answers with that image of that person in mind.”

“I always ask, like, you know, if we were hiring someone underneath Peter to support him, what skills would they have? And they go, oh, well, that'd be super organized, that'd be very rigorous and analytical. That's right. And you're like, huh, okay, you just told me what we need.”

“A massive reason people stop with content is they commit to a release cadence, they cannot uphold, and then stop quickly.”

“I found the correlation in terms of the best interviews of those where we've had the longest chats before we press record, where they've taken the time to build that rapport and engagement.”