The Wisdom Wall

“If you haven't gotten a boost this year from AI, fire half your team right before the holidays, give them a turkey and three months of severance, but they failed. You have a, your team is not good enough. They had 18 months to ship a product that mattered in this world.”

“The only advice I gave to this particular CEO is, um, immediate, like he was hybrid. So I said to force a hundred percent of people returned to office in 30 days and let everyone go, except your S tier engineers, letting them all go. Because you don't need them.”

“Nine billion doesn't clear the bar for seed investing in 2026.”

“If no, if you're not into your 20, 27 roadmap deep into it by August of 20, 26 in the agentic world, your team is not good enough to survive today.”

“If the agent can run 24 seven autonomously, take all your data and build all the analytics, build all the dashboards, run autonomously out of it, um, then your data can flow between apps and you won't even care where it lives and all the fears about headless become true because Claude is your head and you don't need,…”

“It's a moat destroyer when LLMs will lift you from one vendor to the other, and, um, I, you know, I don't even, like, I literally was doing a pitch this week, and the founder was going on and on about their moats, and I, I immediately didn't want to invest. Like, I just, enough, I don't, you don't, your moat can be LLM…”

“And I just think this going back to seed is for suckers. Like you want to invest the hour it blows up. The minute it blows up, you want to get the DM and just wire the money in AI. That's the play.”

“So I'll have to see, but we won't do, we'll never do, uh, Unless I'm forced to, I mean, if, you know, I do it for Sam Altman, but otherwise I'm not gonna do, there's, the firesides are dead and speakers are dead. There's just no point when podcasts are better.”

“Yeah, and every time you cut a corner, every time you invest in a founder that's really nice and really hardworking and really good guy, you never make any, any real money.”

“A CMO today should be able to run their own campaigns, and this is why. I'm not saying you have to spin up, uh, Marketo or HubSpot. I'm saying you should be able to tell your agent, and our agent, our AIVP marketing started running its own campaigns the last two weeks, and it's better, and so, You don't even need to…”

“If he can't get Box to 20 to 30% growth I'm, I'm giving up on, on the rest of the world.”

“Like every agent will leak data if it's allowed to, like every single agent will. That's how goal seeking works.”

“I'd actually don't think any of the agent vendors are safe from disruption because we will, even us, like everyone's promiscuous with agents. We will switch it. Like, this is so much better than what we had two weeks ago. We'll switch to the next one.”

“I just think we have to give up on TAM. We just have to let the revenue show us the path to TAM.”

“I think there are only two types of companies for private companies. They're growing at insane rates or they're unfundable.”

“You can identify a point, a top, oh, .1% founder Without talking to them. I don't think you can do it without any interactions, but without talk, I do, I a hundred percent believe it's possible.”

“Reskill is a delusion. Reskill is something we say to, to make everybody feel better. Reskilling is like when you get, when you, they do layoffs and they bring you in the room and they give you a packet of jobs potentially. It's just to make people feel better. No one's ever reskilled anyone ever, and it's harder in…”

“this is why I tell founders to take their exits and then say no, because they can go bigger, but, but by default, take it.”

“The most folks from the last decade or 15 years are not the right people for the next decade.”

“I think if you're going to own double digits, my view ethically is you got to be there till the end. Otherwise, you're dead weight on the cap table.”

“Hold is your best time to trade on, to legally trade on inside information, though. If you're on the board or close to it, it's your best time to trade on that illegal by not trading. Yeah, you can hold legally with inside information. It's a privileged position. You can sit on that board and know what's coming next…”

“You don't need half your company, and Palantir and Shopify are proving it. You don't need half your company. You literally don't need half the people working at your company. You don't need them today.”

“My rule is if you haven't grown because of AI, you've failed.”

“I call it the AI slow roll, and I think it's the number one thing killing B to B companies is the AI slow roll.”

“All the non-technical CEOs that I've seen, especially take over my investments as outside CEOs, they never understand the product.”

“If you have a hot hand in venture and you're not running the place, I would leave the next day.”

“Since 2021. Every founder with a decent exit, I tell them to take it now. A hundred percent. I tell them to take it for this reason.”

“no, I do think you should take your LP's money less seriously than I do. I genuinely think it's a bad thing.”

“If the churn is anything more than three or four percent a month, it's not even software anymore.”

“my advice to everyone out there that, like, emails me, hey, can I invest in Sastra Fund? Don't put money into any of them, is my advice to individuals. To individuals because I don't even think everyone's full of shit. I think even making three, if you do a seed X, a seed funding, you make three X net after 16 years as…”

“Maybe it's, maybe it's not even until after five or ten million where if you don't have capital, you can't all be Atlassian or Qualtrics. Or, and they fall behind competitively. And I think that's the trap of the fallacy of the lifestyle-esque business, right? Where media businesses are different. The information can…”

“if you get, if you're able to invest in a million and the founders are great, you'll never lose money. If the founders are graded a million in revenue”

“My advice to all of them is they should offer to give the money back, a hundred percent. Offer. And I said offer. I didn't say give it. I said offer. A hundred percent should offer to give the money back.”

“And why it's because the diligence is always confirmatory. VCs decide they want to do the deal and they don't want to hear reasons to not do it.”

“when you raise massive amounts of money early, how are you going to sell for 10 X what you raise? Who's going to buy you for five hundred million dollars? You're dead.”

“You get like, you age out of a lot of things in venture. You really do. And if you're not honest about it, I think you're used to end up in a fee milking vehicle.”

“So VCs are legal partnerships, but I think once they're beyond two, They become dysfunctional almost. They have to be dysfunctional. You start to lose or at a minimum, you're only there because of the fun size, because it, you lose all the benefits of a partner.”

“when I see both as an A plus and any traction at all, like any traction at all, I feel like I literally cannot lose money on that combination.”

“if you have too many rules, they, they always conflict. It's almost unsolvable. There's some number, I don't know, there's some, some number of Dunbar, there's a Dunbar number for rules where you get out to 40, 50, 60, 70 gates on a process. Poor instinct and GrokBot can't decide. Don't spend it. Do spend it. Um, front…”

“the learning and here's the meta learning guardrails aren't enough. You have to have a lock and key. Guard, it doesn't matter whether you build 80 gates, a hundred gates, 200 gates, like, they're not enough, and they get, and then, you know, what's even worse, you get past a certain number of gates, and again, get a…”

“I don't think system of record is, I think it's a moat, but I don't think it's a ticket to growth. This is, I think, super important. And it's something that everyone on X gets wrong. It's great to have a system of record, which Workday has. It means churn even with AI and ALMs help. It's very hard to churn or you just…”

“Now we're seeing three bands of compensation. We're seeing the regular human beings, then we're seeing the AI guys, and then we're seeing the one, the one to five superstars that we're talking about, right? That I have to, uh, that I have to find a seven figure package for as an early stage startup because they're…”

“I think for a founder, when you start to get into nosebleed offers in absolute terms, it has to be 10 X to go for it. It's not worth it for three X. It is not.”

“And the perfect outcome is to sell the moment it becomes commoditized, but before everyone fully realizes it, that's when they'll give you the money, but that's before the value decrease rather than it creates in it.”

“I think the real pressure is, it means anything below that growth stage, you better be a damn good picker. Because it used to be, it used to be when Rory and I met, Series B, even into Series A, you actually didn't have to be a good picker. You just had to be good at math and good at assessing the team. Um, the picking…”

“for public companies, the only thing that really matters to me is, are they growing, um, net new logos, 15% or more a year?”

“If you see an S tier team, and it's in the right space, and you want to hit your number, your 20% ownership, and your fund is in billions, the math just makes sense. It's a bet. It's just a bet.”

“certainly don't do debt instead of an equity round. That's the sucker bet, right? It's just, you better be the hottest thing on planet earth or it's gonna, it's gonna kill you.”

“It's a clean look of what's eight percent, six percent growth with deteriorating market share at seventy million ARR, where you're not reigning cash worth, it's worth one X.”

“As a seed investor, I used to think my real entry price was twice what it looked because of dilution. Right now I'm thinking it's four times.”

“when wealthy folks, especially VCs want to be a CEO, but they're not working at The insane rate of a traditional founder CEO. I just find those run out of energy.”

“Everyone selling seats for the most part is getting crushed. Everyone selling variably one way or the other is winning.”

“My general experience in agentic tools like this is that when they ask for money before they deliver any value, it's not that good. Like the, the, the marketing exceeds the value of the tool.”

“To be a two-pronged AI beneficiary, you have to be able to monetize your AI, and you have to attract new customers. There's two prongs, and the ones that have done it so far are close to infra, right? Um, Cloudflare, Twilio, Mongo, Datadog, uh, and even DigitalOcean”

“when a top fund doesn't go all in, On an investment, it's such a bad signal. Not only is it bad if the tier, if the, if Andreessen does your seed and doesn't lead your array, that's the classic discussion we could have done on 20 VC in 2015. Right. Um, but the subtle one is when you do the growth round, when you do the…”

“Is your Maos, Wows, and Dows growing faster than revenue? If so, things are probably working for you in the AI age. If they're, if they're declining, just like net new customer count, right? If it's declining, you're hiding.”

“You checking the box does not work with agents. The check the box feature cannot be monetized in the AI era.”

“If you have an executive that's truly arguing with the CO in public, in the media, right? And or like Dario back in the day at OpenAI going directly to the board with craziness, they gotta go. Like, it doesn't matter. They gotta go. They, you cannot be out in the media arguing with the CO and you cannot be Dario, no…”

“And whatever, if any VPs get this far on the pod, whatever you do, do not reach out to your VCs to say there's problems with their CEO. You will, you're losing your job. And not only are you losing your job, it doesn't matter if you're right. You're your, at some level, you're probably right. If you, if you're a…”

“The reality is you have to go truly multi-product earlier in this type of situation. Not, not just a little feature, right? Not just a little enhancement. Um, but you literally probably have to build five distinct products to get to that billion and not, um, you know, not all founders are actually up for that.”

“Agents, agents are goal-seeking and agents are going to make, not only going to make the same mistake as humans, they're going to work a thousand times faster. So even if they make the mistakes, 10% as often, Rory, help me with the math. If they do a thousand times more productive, they're still going to make a hundred…”

“there are so many applications like the ones I described that were not that sensitive to token costs. If you use 204 102,000 dollars, 10,000 dollars of tokens for a month for these, it just doesn't matter. And so there's the open router world where costs are super sensitive. But there are plenty of applications that…”

“Is your ARPU 50% or higher than it was pre-AI? It's a really simple test. Can you drive ARPU up 50% or more? It's very different at Salesforce or ServiceNow. It appears that Notion has done that, in which case they, they passed the test, right? But I want to see 50% or more ARPU growth due to AI, or it's just a…”

“The answer in 2026 is what commercial AI tool have you brought into your organization this month? That's the test. Anyone that is on the bleeding edge that you would want to hire. Now there are so many great products in the market. Okay. There is no excuse in any role to have not brought one tool a month into your…”

“The job today is not to screw around on ChatGPT and to be a prompt engineer. The job today is to bring the best AI and agent, agentic products into your organization and leverage all the hard work that the engineers have done building those products. That's your job. You don't have to screw around. You don't have to be…”

“Owen said there's not going to be any difference between support and sales in a lot of what we do. All these agents are converting to a meta, a meta agent that does more, replaces a lot of humans and is worth a lot.”

“App is, this is becoming necessary core CRM functionality to record and manage every keystroke, every interaction, everything you type, everything you do, because otherwise you can't automate a CRM. Like, the next generation CRM just does not work if you have any privacy in the workplace at all.”

“They're not long-term services businesses, but if you need humans to train it, if you need humans to manage it, if you need humans to iterate it, you're, you are, you have the same constraints that services businesses have.”

“You're not going to win today if you're doing quarterly release, best effort releases. And I would say most public software companies are also, and many struggling unicorns, I would say almost all struggling unicorns are doing best efforts, quarterly releases. That's death today.”

“I believe every platform that is open is at risk that an agent is better than the native platform. And every platform that is closed is, is at risk of, of, of being At least slightly bypassed.”

“For simplistic folks, for founders, I say inference is the new sales and marketing.”

“The other advantage that the new entrants have is that if you have the best agent and you have the kind of market demand we see, right, then you're, you're, um, for you, your inference costs are a marketing cost. The established players don't have that luxury. They're already spending massive amounts on traditional…”

“tweaking pricing models doesn't change how much folks want to spend for a product, right? That's a fallacy. That's, that's what consultants do. They're pricing consultants. It's great, but if no one wants to pay more than 20 grand a year for your product, you can't force them to with a clever pricing model.”

“It's like the best researchers in AI, the best, the ones you need to win, they only want to work what they want to work on. And they will leave a lot of money behind.”

“And at my entire life in B to B as a founder or investor, every time we try to be too negative on TAM, it bites us.”

“If this growth is durable, ok, if we're seeing signs that it's durable, if it has, if it really has a 170% NRR and 98% logo retention, And it's accelerating at one 50. This is just the bet you do. You don't, you don't, you don't pull your hair out or have to have lengthy dinners about supplanting labor with AI and, and…”

“So you literally can't brute force a hundred million in 10 months with humans. It's just maybe, maybe, maybe Larry Ellison or Mark Benioff could, but I don't think anyone else, there's just not enough calls and like, you can't go from one to a hundred in 10 months without massive inbound demand and a lot of AI.”

“I do not think you can push your team too hard. I think you should push them as hard as the business needs to go, and if they leave, it's great.”

“Because if you're growing 15% or so, or, or in the, in the teens, probably the majority is from price increases in today. That's, you know, it's fake growth. It is price increases or stuff jammed down the channel, and maybe it's a couple percent from new logos, but if you're increasing effective pricing eight to nine…”

“The optimal way to run it is for everyone already to want to invest for real without games before you open your data room. And the super optimal way doesn't even require a data room because they already, you don't even need a data room because they already want to invest. They need diligence, but you don't, the best…”

“You're either getting money from compute, right? This massive spend, or you're getting money because you're using AI to replace humans. Otherwise, you're not gonna grow.”

“Even 10 is not really worth it for a founder. It is worth it for the VCs.”

“if you get an M&A offer as a founder or an investor, and the founders make the decisions, the VCs don't make the decisions. If your TAM isn't really accelerating, take it.”

“we used to catch up around 10 or twenty million ARR. And actually in some cases in SAS, you would lose your, your, your capital advantage around twenty million ARR because you would catch up, right? Like, like in the last year in our Qualtrics. I'm not sure that's true in the age of AI. I'm not sure that you lose The…”

“Look, if nothing else, if you're not number one, don't spend like you're number one. Even if you're growing pretty quickly, like Harry said, if your number, if you're the clear number two or number three and 80% of VCs are going to drive by, if you burn a hundred K a month, like you actually may have the best exit,…”

“the frothiest sign is now LinkedIn LPs are bragging about their returns on LinkedIn LPs. When LPs are start bragging about their returns to me, uh, that that's the, that's the most, 20, 21 moment I've seen when LPs are LPs who are usually hide behind the, the, uh, wizard of Oz curtain are bragging about their returns.”

“being number two, just as founders, it's a cheat code. Like just, just don't raise too much. Be acquirable. If you're number two, be kind. Right? And you'll be shocked in frothy times the offers you'll get.”

“At the end of the day, unless you're a total douche, if the founder wants to sell, you sell. It's not your decision. It's not your decision. That's the height of hubris in my experience.”

“any public company quoting billions of AI-influenced ARR does not believe they will have billions of real ARR.”

“Our job is to make money at Salesforce Ventures, but it's more important we don't lose money. Because if we lose money, we have, we may have to take an EPS hit or an impairment charge. But as long as our investment doesn't go down, it's pretty much okay.”

“These are ones we used to shy away from in venture. These are one of the many risks we're ignoring today because the growth is epic. We're ignore, we're ignoring so many risks and platform attaches all over AI B to B. There's so much platform risk and we've given up worrying about it.”

“He's ruthless, Zuck's ruthless, Karp's ruthless, and if you think you're gonna win in B to B, if you're not ruthless, you're gonna lose.”

“normal times you want to optimize your fund size to achieve the maximum carry you can in a given time, right? And then just go raise another, right? In an ideal world, you might even raise the fund a year, right? So you can get into carry mode as quickly as possible.”

“That's why so many struggling unicorns are in an existential death spiral because they can't attract anyone great. Not a single great person is going to join an ex, you know, unless the founders are great.”

“I still feel like for startups, we're giving Revenue valuations that don't have an adjustment for different ways their comps trade in the private markets. And if ramp is in a space that's two to four X revenue at, at when it's public, uh, or whatever that you could look at the comps three to four, like it, see, that's…”

“My view, Stuart is a generational founder, right? Did it multiple times. Did the kind of CEO we'd all love to work for, right? But I think deep down in his heart, he didn't want to do multi-product or they would have been multi-product. Like it had an existential ticking time bomb because it could only be so big as a…”

“There's no analyst coverage. There's the institutional buyers are not there in the single digit billions, right? And it's just, you better be wherever there is any liquidity.”

“for seed investing to really make sense, the next round should be three X to justify the risk. And for A or B, it's gotta be two X, or you should just wait.”

“when I was looking at this on a spreadsheet, my new role is at two billion, sell unless you're a hundred percent sure you shouldn't as a seed manager at two billion.”

“I think 99% of folks should only be in liquid investments, including people in tech. You should be as liquid as possible. It's just too stressful for the, like VTI is the perfect product for 99% of people. It's the perfect product. You cannot beat it.”

“What I worry is, is just that when there's so much competition, I think everyone's going to be less durable. It's not your ten-year-old SaaS company that is seeing less durability. I think everyone, I think this, this is new, this less durable revenue”

“if you're a founder and you like big teams and you like scaling, but you don't want to do the IPO, leaving 12 months before the IPO is the right time, right? The market's not going to be shocked, and you like scaling, you like people, you just don't want to deal with Wall Street. That's the perfect time to leave, like…”

“PE is the big problem. They're really the same thing. I mean, venture is a subset of PE, right? And the PE is so much bigger. And the fact that these deals are, did not go public in two to three years is the bigger stressor. Venture, venture, they don't love it, but they're, They're modeling 20 year illiquidity with…”

“Venture's a rounding error in most of most endowments, right? It's a subset, just like seed is a subset of venture. Venture's a subset of PE. It's not that important. It's just juice, right? It's just a way to juice your returns. P.E. is where you put, deploy more capital, and if it's been five years and your cash flow…”

“I tell every founder to stop at a hundred million valuation. If you're not sure you're gonna IPO, now you may get it wrong, right? But if your gut says, I don't, IPO, man, 50% of five hundred million, that's not me, don't raise that north of a hundred.”

“It used to take you five years to follow the product market fit. Now it can be five weeks.”

“But in some ways, these crazy AI deals, once they take off are, are the cheapest from a revenue multiple perspective compared to like seed and a deals.”

“What, and there's, and this is an age in AI where there's no moats. So if there's no moat, you better run faster.”

“a lot of that is driven by taxes in the US. It's not really driven by liquidity for investors. It's driven by this brutal tax situation of RSUs expiring. They're expiring on employees and they're, and they're becoming taxable events before the IPO.”

“I'm not seeing the type of just tire kicking that I saw a year ago. I'm not seeing it. I'm not. Maybe other people with broader portfolios will tell you different. That's what worries me. I don't know. We're waiting for P to bail us out. Right. Forget about the multiples and the, and the waterfall. I'm not sure they…”

“I absolutely think you can IPO in today's world at two hundred million, but you probably have to be growing north of 50 to 60%, and there's just not enough of those Candidates.”

“17 years for liquidity. How long is the nominal fund life? 10 years. It doesn't match up. Doesn't match up. Yeah, you get two one year extensions.”

“If you, if you resist this, you are going to get steamrolled because the customers expect it. They're looking for it. How they pay for it is a different question, but I see too many founders still hiding or running from AI or mocking it or making fun of it. And I think it's a path to destruction.”

“I think for the math to pencil out in venture, we do need a rebound. The math. And this is, forget about the unicorn rounds and the crazy. We just, we do need some, we do need a 30 to 40% multiple reflation, or we just can't make any money on any round north of a hundred million.”

“Well, it's what, it's what, I mean, Adobe, the majority of Adobe's revenue is still from designers designing assets in creative cloud. And that is exactly what Canva does. It's not prototyping products, which is what Figma is great at.”

“this is why I tell almost every individual do not invest in venture funds. It's dumb for individuals.”

“I think that there's no point in even as a seed investor selling before a billion. It's not enough money.”

“One good thing we learned in SAS is until the Salesforce decline, we learned that generally high NRR lasts forever. It lasts to a 1,000,000,02 1,000,000,010 billion, but we also learned the CAC never comes down. And actually the public SaaS companies have the highest tax of all.”

“when you've acquiesced to having a mediocre management team, it's, it's over. How are you ever going to regrow if you're with a mediocre management team? So when you start covering for a mediocre management team, I'm not saying fire them. That's a more nuanced topic, but if behind the closed doors of a board meeting,…”

“The best investments go one to ten million in five quarters or less, the very best ones.”

“if I'm invested in someone with 10 employees or less, I don't care anymore what the management is, but I do care what the CTO is the one I care about.”

“when I see these signs that the software isn't good at a million, it rarely gets better at 10. It gets worse. The load goes up. The workflows go up.”

“I believe the best opportunities find you at the end of the day. It's not that you don't find them. Okay. But they also find you by the same token. And if you're gonna pass on an amazing binary set of founders, an amazing CEO, CTO, just because they're in a competitive space. You're, you're gonna lose, you're gonna…”

“If you have the best engineering product team in the industry, uh, having a lot of competitors is a positive because they help grow a large market and you keep each quarter you pull away each quarter you pull away, right? Each quarter you pull away and it becomes a net positive that everyone's investing so much money…”

“If the founders say to sell, sell.”

“there's zero diligence for these checks. None for these follow on checks, right? As long as the top line looks good, no one ever checks anything below the top line. There's no, there's no diligence, no customer calls, no nothing, right?”

“The IPO markets don't care. They actually don't care whether you raise nothing right in primary like Atlassian or whether you raised a crap load like rubric. Or whether you raised almost nothing like Klaviyo and then a bunch and then all, and then burn nothing. The IPO markets don't care. They care if you're efficient,…”

“I find if you take the last four months of growth and average it, that's going to be your growth the next eight to nine months.”

“You can't put enterprise or mid-market people into these S&P models. Just the toolkit, the type of people they hire, the way they spend in marketing, the customer lifetime, none of their metric, it just doesn't work.”

“If you're putting the rest first, I think taking out more than ten million is a bad sign, even in the hottest round.”

“If you don't know in 20 minutes that this is one of the best founders you've ever met with, don't do the investment.”

“And I think founders should take inside, like, good inside rounds very seriously now because of the reason you said. This is different than a bridge, but if one of your investors really wants to step up at a higher price, Right? Just, just eight, six times out of 10, just, it's a good, it's, it's a good thing in this…”

“You can't have, whether the venture outcome is three hundred million or a billion or ten billion, you can't avoid triple, triple, double, double, at least in B to B. You can't avoid it. You can have a year gap. You literally can take a year off, but you can go triple, triple nuts, double, double, double, double, like,…”

“They think it's for the fees. It's not for the fees. It's because that's what it takes to sustain a team.”

“really today it probably has to be closer to two hundred million because that's when you can really IPO, right? Approaching two hundred million. So you've got a decade to get to two hundred million”

“If you're not growing, I think it makes sense to mark it down. If it's growing at a decent rate, I think, um, if you're not Fidelity or a late stage investor, I think it's a waste of your time to mark up or mark down because, um, I asked all my LPs this question. They said, if it's growing, they don't care.”

“You have to invest in CEOs that were better than you. If you know the problem, if I, if I know, if, if I'm, if I'm a podcaster and I know Riverside or whatever the other versions are, and I, and I look, Riverside's great. We're on it today. And you meet the CEO who I don't know, and he's not better than you, Harry, you…”

“what I have learned is that, you know, hypergrowth in the early days can decay for a variety of reasons, right? But it does prove you have a large TAM. It always proves to me that if you grow quickly in the early days, you have a large TAM, even if it looks small”

“even of this Ivy League of venture-backed founders, I would say only maybe 15% really can take the feedback. And, uh, 25% will tolerate it, and then 60% will hate you for it. They hate you for it.”

“one of the VCisms I hate is conviction. Right. Because conviction can, can justify so much sloppy thinking, but it doesn't mean it's wrong.”

“I don't think, I don't, I think that, uh, only way a B to B startup dies is when the founders kill it.”

“When you meet a winner, you buy all the shares. Now, if you can buy a quarter of the company, you buy a quarter of the company. If you can buy two percent of the company, you buy two percent of the company. But you either buy all of them or none.”

“If you don't have those two AEs and you hire a VP of sales, 80% of the time it doesn't work because there's nothing for them to work with.”

“in true enterprise, like real enterprise, the founder is often the VP of sales until ten million.”

“basically a hundred X ARR startup has to at least quintuple next year with high quality revenue, at least quintuple.”

“if you take money from a big fund as an early stage founder, there's actually less pressure. This is so changed. The funds are so big and they're raising funds every 12 months. We have different portfolios and my portfolios, when the multi-billion dollar funds have come in and led the A or the seed, they're barely…”

“that's why I beg founders not to use notion and board meetings. I begged them to force everyone to make slides to spend the time because we all love notion and Coda. We just put our stuff in our Google docs. It's so efficient, isn't it? But not only did I think board meetings were stupid when I started investing, you…”

“I actually think the compression, what I've seen, I think it's harder on the late stage investors who no longer can do diligence.”

“The learning is when you're on your own in a solo GP fund, you're actually, you're more conservative. I say no to deals that I would have done in another firm, and I'm not remotely convinced that's the right decision.”

“in an ideal world, a ten billion dollar fund leading your 700,000 dollar round is suboptimal because that's nickels and dimes. It's pocket change. No one putting in a tiny amount of money is going to remotely care if they write off the investment.”

“Someone that puts in one, two, three percent of their fund into the investment is going to do whatever it takes to To help the company and to help you raise the next round.”

“because if I would work for the CEO, then I know we can recruit an amazing team under him, and he's already built the bones of a great team, and whatever happens, I'm with the company until the end of time, and at my gut, I feel like we can't lose.”

“Once you hit what I call initial scale, when the business, it's usually around a million a month in recurring revenue, or maybe ten million a year, 800 K a month in recurring revenue. Once you hit that, you can't be killed in SaaS. You cannot die. You cannot be stopped.”

“while operationally that may be a good time to sell, that's when I sold it, basically a million a month in revenue, it's the worst time to sell. So never sell at that point unless it's twice the maximum amount of money you would ever want.”

“I define a market by its, its, its current growth rate. I believe that if you can, I believe that if you can hit a million in revenue, and I invest before that, but if you can hit a million in revenue growing 15% month over month, you're inherently at a nine feet. You can inherently build a company with hundreds of…”

“To make any money as a VC, even just as a partner in a hundred eighty million dollar fund, which is not huge, If you're not at least going for a unicorn, no matter what ends up happening, I can't make any money, so I'm out.”

“AI is expensive and it's not getting cheaper. It's not, it's getting more and more expensive as we burn more and more tokens. We have longer and longer runs. And so the pressure to use cheaper models is going to go up.”

“You can consume any top tier developer can assume an order of magnitude more tokens than they are now. The ideas are limitless.”

“The most in my career today, there are the most reasons to not announce, if you can get away with it, to not announce a hot round. Right. If you've already got enough, if you've already got enough going on to attract talent, right, for recruiting, um, especially if you're not selling directly to tech buyers, right, to…”

“I do think you don't make the most money if you wait three years to deploy your fund. You make the most money if you can, uh, thoughtfully deploy it in 18 months, right?”

“I think in the age of AI, um, massive dilution has been sort of institutionalized.”

“Why is a, why would you join anything that you don't have high certainty, not just they're going to be a unicorn because it's not good enough, that they're going to have tender offers, right, in the next 24 months.”

“When you leave oligopolical stages, there's massive price erosion because you're no longer competing on features, you're competing on price, and that's exactly what we're seeing.”

“I think any public company in decline today that gets an offer, a premium of even 15%, they have a fiduciary duty to take that very seriously... management with their earn out, they're going to take that deal in a heartbeat.”

“for the SPV work, it needs to be one, one, one WhatsApp message, and I get the, I get the two hundred million to invest. Then I'm all, then it's the best model venture there is, right?”

“There's a different issue coming, which is coming for more of us in tech, which is that our humans just can't process all the output.”

“That's an instant pass on a founder and a pitch telling you when they got into Bitcoin. That, that's my flip side of too much feedback after zero. Like, if all they tell you, if in the 1:20 seconds they tell you about when they got into Bitcoin, tell them to stay in Bitcoin.”

“this is the job of early stage investing is what foundation did. This is not using Mark Andreessen's brand to muscle into the B.”

“when wall street lets you spend, it doesn't punish your stock. You should spend every dollar on the balance sheet. They'll let you because you'll build it back up, but it's trapped when growth slows”

“Churn that is churn that is deferred still exists, and it is, it is where the rent to CEO and the mediocre hide.”

“If your agents are only 60% as good, you're in a slow death spiral.”

“In my experience, I don't know what you guys think. In my experience, that has about a 30% chance of success. Just, just roughly. That bringing in the big, the perfect LinkedIn, giving them a massive portfolio and either attaching them to, and attaching to this something in tumult.”

“If in the last three to five years, you have successfully deployed a piece of enterprise software of any sort, you yourself, not some agency you hired, but if you have deployed it, you can deploy any agentic tool, any, and you can become the hero in your company and you can become the hero in your functional area.”

“it only has to be, the risk only has to be ambiguous in a B to B deal for you to lose and go with another leader. It just has to be, it's a little bit less secure or they went down for two days or the, the database was left open.”

“FDs forward deployed engineers for the moment are a limiting factor. And let me explain what I mean. What it means is no one has enough fully trained FDs that, that can get a customer up and running fast enough. No one has enough of these resources.”

“These, these are carries many funds now vest over 10 years. Some even backload carry, right? Because they want to penalize the folks that leave.”

“The 2023, 20 22 toolkit works perfectly well at the hottest AI companies. It really does. It really does.”

“the super interesting thing about support is it becomes a Trojan horse to do everything else. Because when that's the main agent, if that is the main agent you're working with, you'll start using it for sales help or for research or for marketing or for other things. And, these become more horizontal agents.”

“the idea that you can use. Uh, cheap models and cut back on your inference and still be competitive? That's the thing. Still be competitive with the hot Andreessen-funded company? Like, no chance you can be competitive without that inference.”

“the classic take in ventures, it's not really an asset class. It's a weird niche of PE. Yes, the top Your quartile, certainly the top decile perform, but the rest is a disaster. So it's not an asset class. If the bottom 75% isn't even worth getting out of bed for.”

“You only need two or three leaders, a company of any scale. The best ones will find two or three.”

“There's no excuse. We all use the same LLMs. There is no excuse for you to not have an agent as good as the new kids.”

“Like, I think if you want to make money in venture, you gotta, you gotta search out Spite. This is driving the greatest AI companies of our generation is Spite.”

“I believe, and don't get me wrong, this particular deal may work, but in my life experience, You're just flushing your money down the toilet. When a great seat founder reaches out to you, I've got this one I want to do. And then you dig a little deeper. I'm the non-executive chairman. I'm putting my, some money in and…”

“the angst is gone around mispriced rounds, overpriced rounds, and good or bad, I think that advice has no audience.”

“And if you've been, for folks, if you've gone through M&A, you really want to have two, two real offers. Back up, you want to have one real and one fake offer, like one, at least one fake offer. You can tell CorpDev you have another offer.”

“But it is, it does work in my limited experience because even if you do three rounds at the same day at 306 109 hundred or whatever it is, when you're oversubscribed, it's just a message to the new investors. The price is 900. It might be, the price might even go to one, two. Like I've seen it too. It's just a step…”

“across every professional experience I've had from startup to scale up to VP at a fortune, 500 tech company, nothing happens when you're not in hyper aggressive mode.”

“You just can't take that early first month explosion as seriously as you used to. It's not as defensible.”

“One of the reasons just partnerships are dysfunctional, and maybe it does, maybe we could move on, is that it's almost impossible for performance to tie to economics.”

“I think there is so much fear among VCs of getting out of step with the most successful founders. There's so much fear and you guys are going to disagree with me, but I see it all across my portfolio. The better the company is doing, the more everyone's a grin fracker. There's just, just never a critical word said.”

“I just don't know that there's this massive DPI pressure. If you have a hot, if you have a hot hand.”

“when you're up enough personally, it makes sense to hold your, all your winners in the public markets for taxes and other reasons. There's just no reason if you're personally up enough, uh, to, to sell any winner, right?”

“Founder friendly is writing the check when no one else does. That's founder friendly. That founder friendly is when no one else is there at the board meeting anymore and you're there and you still have a W on the other side of it. That's founder friendly. Founder friendly is when you actually recruit the executive for…”

“When big, when big companies with a lot of cash make corporate investments, it's weird because if you're generating, at least in the US, if you're generating massive amounts of cash, it's orphaned on your balance sheet. You can't just go hire a thousand engineers. It hurts your EPS, right? But if you can swap it, one…”

“If you're, if you're at less than a hundred million in revenue and someone wants to buy your team for twenty billion today, I say take it.”

“But we forget about the employees don't care about, they don't even know what dilution is. All they care about is what happens with their stock.”

“if you are going to leave a fund, and you can, you have a hot hand, better to do it early. Like staying longer doesn't help. Like it might seem like it helps the fund. It doesn't help you. You're probably not going to leave with much carry, right? You're going to have to start over.”

“Is it because oligopolies maximize innovation? They don't maximize discounts, but they pour all the money back into R&D because they're competing on features, not price, right? If you believe in technology, you might almost want oligopolies, right?”

“It is almost impossible for most public companies to actually spend the cash there they're generating. So Zuck's got a triple down here because he's getting also a hall pass. The market's saying it's okay to spend everything, right?”

“My life experience where you have more is that four X is always like three X. Like, whatever, like, there's always a reason when, when you actually see the distributions, like, whatever that math is, it's never as good as it looks, right? However good it is, it's never as good as it looks.”

“the only value I think you can add in venture in the world really is if you discover talent that would otherwise not get funded.”

“I think re-skilling doesn't work, and I think Canva's basically saying, shit or get off the can, guys.”

“when you have limited reserves from a Cedar smaller fund, you put it all in your fastest growing companies. Like, a hundred fucking percent. There's only one criterion. Triple digits growth, you know, double digits per month, that's it.”

“I tell all founders to sell now, by the way. I just, I, only as a challenge. I'm not saying you shouldn't take this fake offer, but this is my, this is what I, my life lesson. I tell you to take it. And then if you come back the next day and say what you just said, which is F no, it's the right answer, right? But I…”

“In my limited experience, like 10 X actually isn't enough because those are soft commitments and people put in over allocations to make sure they can get it, and you really want to be like, 30 X oversubscribed to pop hard, which I don't know if that's your, what you've seen on your public companies, but that's tough to…”

“Three times as much money for the same dilution de-risks your life as a founder, right?”

“I think you've got to assume now over two thirds dilution from seed if you don't do pro rata to IPO two thirds.”

“that's the special part of the, of being an SF. You feel like you're failing every day compared to everybody around.”

“Like to all founders out there, settle everything. Especially when you're not in the wrong, when you're not in the wrong, settle it, right? When you're, when it's the, what, cause it's so hard if you're not in the wrong to settle it, right? It's so wrong. That's the, that's the number one reason to settle it when…”

“PLG is just freemium with better analytics.”

“the real goal of PE is if you use debt correctly, even when you lose, you win. Because you have, you've taken so much out, right? Or you've put so little equity, and if you could put in 10, 20% equity and leverage it up, like you win, even if you lose, you win. As long as you have an exit, you win, right?”

“But I worried too much as a founder. I remember about losing single digit millions for my VCs. I shouldn't have worried about it. It was bad for them and it was bad for me. I should, I stressed it too much. Like they can survive. You know, a four hundred million dollar fund can survive emergence, whatever too, which is…”

“Overall, I would say, 80% of the time, the CEO is better than the CTO, especially at the seed or early seed stage”

“Really in today's world, you're going to suffer 50% dilution on the way to IPO. That core seed fund that you struggled to get 12% of, you know, it could be six by the IPO.”

“Five co-founders is too many is one learning. Now you can have 12, but I think five making decisions is too many.”

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

“those are the investments where I just don't think you can lose, and, and when I've, my losses, to tie this all into the theme, my losses are when the founders weren't that way.”

“I really think it, to go long in this business, you, you, you've just gotta to bleed money. You've got to want to put the zeros and ones in your bank account, or what's the point?”

“Now, if you're too rich in venture, you just have to raise billions and billions and billions. That's the only way.”

“The best investors are nudges.”

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

“That's the superpower that everyone on this, uh, on, on this podcast has, which is everyone knows who's better than them, right? That is one superpower that successful founders have that, that money investors, when I say they had, they don't even know what it means.”

“I started off completely full stack, right? I started off working at a third party VC firm all on my own loan guy, no help, right? Doing everything. And I've done that. And now I've seen after 10 years, it's not optimal, right?”

“if you want to see ever those one or two, I actually think it helps to see 10 times more startups than it did five or six years ago. 10 times.”

“It's not today. There's no way it is today that that that absolute comp is the biggest driver of retention.”

“I think a great founder will take a 20%, will take a 20% lower or delta term sheet to work with a high, someone they really want to work with. Beyond 20, I think it may be mythical.”

“First, I basically decided that anything north of 15 X ARR had a suspect valuation in the current world. Okay. That's what the top and this most startups are not going to be the very top. They're most aren't going to be data dog or snowflakes on the other hand there earlier. So I said anything over 15 X ARR is suspect.”

“in B to B, you got to sell, man. No one needs another SAS product. We already have 11 payroll companies and 88 CRMs and 96 mark. We don't need one. So if you can't force your way into a market and Selling stock is sales.”

“I think here's what I think the most common reason is they have good, but not great growth. This is the risk for seed investors, especially late seed investors. And I didn't used to want to think this was true. When I started investing, I did a whiteboard and I looked at, I said, okay, when I was at 10 millionaire, I…”

“The earlier you get a winner and a winner really being like the person on the board, the first investor, like an iconic winner where the founders will back you. The earlier you get in your career, you could probably raise three funds on the back of that, even if they, all the rest of your investments are dogs, right?”

“And so, so that means you need a three billion of exits, right? Gross. So that means you need thirty billion of market cap to make that fund work. If you have 10% real ownership, thirty billion of market cap.”

“Doing a seed investment at five and exiting at five hundred million sounds great, but if you own 10% and you have a fifty million dollar fund, it's still only one X. One X doesn't, doesn't pay the rent for anybody.”

“In the old days, the rough rule is we could raise, including A, B, C, D, E, F, G H I and J rounds. You could raise a hundred total, right? Then that kind of grew to like three or four hundred million as the IPOs got bigger at the peak. And now we're probably back to a hundred million, which is everyone has to be…”

“layoffs don't really solve anything. They're just little, they're little snacks, right? They make little incremental changes, but layoffs don't create growth on their own, right?”

“If you do a brief strategic retreat as a startup, it's fine. Take a quarter, get your house in order, right? Get rid of that terrible VP, cut your burn rate. But if you stay in strategic retreat for a year, you never pull out of it, right?”

“founders have this investing superpower that money managers don't have, which is they know who's better than them.”

“the best founders are great communicators one way or the other. Right. And so if you can write an incredible cold email, like an incredible inbound email, um, you, you can, you can judge a human being and a company just from that email.”

“Invest in like five companies your first year that are your top problems, where you have this special insight, and you'll know who the best founders are in that space too, because they can't bullshit you.”

“don't listen to the advice to slow it down, right? If you join a larger fund, their incentives are different than yours, right? You're new, the ball is set. They're just hoping, a large fund is hoping in the next two years you find one, one notion, that's all they care about, and that you don't create a lot of drama or…”

“there's probably no better signal than when you compete with a free open source platform and your product is exploding, even at an early day, because it's, it's gotta be magical.”

“most of those two by two matrices are throwaway slides. Don't have a throwaway slide. Don't have, it's a, it not only is it a waste of everyone's time, but it, it makes you, it makes you look less than great if you have a throwaway slide.”

“subscale brand building on VC is a waste of time.”

“if you have a top brand, you're going to get into one or two good deals a year by hook or by crook. If you play the game and it's enough, that's the beauty in venture.”

“my rule is, and I've made this mistake since, don't invest. No matter how much you love, you can love them as humans. They can be doing very well. But if you don't have this crazy 20 year commitment to building something huge, it's hard to make money in venture.”

“What does a mediocre VP of sales do if there's sixty million in the bank? They spend it all. A hundred percent of them spend it all.”

“First, make sure they've sold at your price point. A sales, if you're a five K ACV startup, do not hire someone from a million dollar a year group, no matter how much you love them. It's the wrong toolkit.”

“But being the only active investor, it might be five if you take it seriously.”

“what I quickly learned is meeting with founders that weren't Part of the Sastra community, even back in a few years ago, was a complete waste of my time. I was completely undifferentiated as an investor. They didn't know who I was. Why not just go to Sequoia or Andreessen? And so any meeting I took that wasn't a…”

“So if you kind of back into that math with a little dilution, that means every single time that we invest, I have to believe the company will be worth at least seven hundred million dollars.”

“the earlier you go, the more you have to squint to see market pull. Once you hit four or five million in ARR, it becomes a numbers game.”

“If you have one, I'll bet that you can get 10 and then a hundred. As a founder, this is a bet that I'll make that other VCs won't. I will bet that one is not an outlier, that one is the future. But if it's zero, I'm not sure I'll take the bet.”

“That's how number two and number three get bought. Not because there's a panic for land grab, but because I didn't get what I wanted, right? That, that, that's when you got to be really thoughtful as number two, um, uh, because, uh, that that's when you get bought as number two and number three. I really, when just…”

“In my limited experience with my portfolio, these mini, these mini Elon packages, they're basically all focused on 10 X what the last guy paid. That's what all the late stage investors do. Whatever I paid, 20 dollars, 20 dollars, and I just want 200 dollars for you to get it. I don't care whether there's a little,…”

“If you don't have another offer, it could take three, four, five months to close an M&A deal, right? If you have an offer, it turns out any big company can move in a week. Not to close, but to sign term sheet. Any big company, you're shocked how fast they can move when they're in deal mode and there's a back-end…”

“What I've learned from my portfolio and I think you guys will agree is it creates an out an unexpectedly large amount of alignment. You get, you sell five percent of your company to a hundred billion dollar partner. It don't matter to Rory's point. It just don't matter if they own five percent of your startup. It…”

“founders hold grudges in a way that VCs actually, I think don't because VCs, you miss the deal. You got to find another bus, right?”

“downside protection is real. We just overstate it. Right. And, uh, the number of potential acquirers is real. We actually overstate that too.”

“what I've learned as a founder is you don't get, it doesn't hit you until around year four to five. This is just the way humans are. Okay. And, and, and he's young, but Look at founders you've invested or met with. Around year four to five, the weight's there, ok?”

“if I can put 5,000,008, ten million into an emerging GP, okay, and they don't expand into a multi-billion dollar fund, it's, it's, it is irrelevant to a large endowment, unless you've got a little chunk of guys that are just doing emerging managers, and they'll put in the work, or they'll put in the time, or you're a…”

“Because the odds that VP that wants to do the deal is there in 12 months and that their priorities have not changed, you know, approaches single digits.”

“No one loses their job in Adobe over the small chip deal. Otherwise it would never happen. No one would take any risk in buying an emerging company, right? They just wouldn't do it.”

“IPOs are very binary, right? Either folks get super greedy. And they're genuinely massively oversubscribed or they barely get done at all. So I, I just think that is overstated by the media that there's existential IPO. Until, until it shows up in the numbers, I don't think, I don't think fear overcomes greed.”

“When you're treated terribly as a CEO was like Jeff is, if people come back with humble pie and you care, you get over it. You, you, you got to pay the price. Like they might have to have to have given them a half million billion dollar package, but if, if there's a little humble pie, you get like you, you, you know,…”

“When you come in hot to buy a company and take it off the table, three X is a traditional way to remove objections. And close the deal instantly.”

“Maybe at some point, even if you're Revolut, if you really want to do deals for real, it's, there are limits to private stock in cash, and if Databricks goes public, and it's worth two to three times Snowflake, it can buy, it may be able to buy the parts of its journey, and it's already been very successful in…”

“And so on the one hand, it seems like a dumb idea, like you're creating mercenaries and perhaps you are, but in the age and you're asking someone that's 18 months into somebody else to leave and wait 12 months to make a dollar. Um, that can be a tough sell in, in, in an age of plenty, right?”

“There's like only a couple of deals that matter to VCs. So when you, you'll see a VC stay on a board for 20 years and you'll see them always hanging out with this one CEO and Thrive has a lot of winners, right? But this is a big winner, right? And so anything you can do to go deeper with those founders on your one or…”

“one thing that hasn't changed is in the age of AI is big companies only have so many priorities. They can introduce a lot of little, little tests, but at the end of the day, it takes a lot of energy in a big company to Keep a big initiative going because there's so much else to support.”

“databases are a hard problem. Like you can only lose so much data. You can only have so many issues. You have to figure this out. And five years of investing in a database that everybody uses, it's, it ain't so easy to turn and leave your database.”

“You'd rather not create an anthropic when your team leaves too, let alone thinking machines and all that. You don't want to force two of your best people out and they build your top competitor.”

“generally, once you descend into low growth, uh, and that's different for public companies and private companies, you're worth, I mean, if you're worth anything, you might be worth nothing as a startup, you're worth in the three to five X ARR range”

“you don't really care as a late stage investor. You don't care whether it's one one or one Oh six or nine 84, because you're, you're making the exact same amount.”

“So all I know over these cycles is you buy a house before the next massive IPO wage.”

“if you have a public company trading at a crazy high, high multiple, right? 20 X revenues, um, that has existential losses. You got to use your stock as your currency ASAP. You gotta buy everything you can that can address the bottom line or other challenges you have, right?”

“And then the, the, the life lesson for founders, it's tough is look, Scott's gone now. Right. It's always a weird thing, um, when you do M&A and it's not with the CEO because there's a good chance you outlast them.”

“everything Sam says that seems off the cuff or like on the side or a little futuristic, he's very clearly telling you what's going, he's very direct. And when he says, when you hear that they're thinking about it, He's done it.”

“I think the venture lesson, be visionary, but relentlessly honest about TAM. Because it's a TAM story at the end of the day. If you have a number one or number two player in the space and you see a TAM explosion happening, that's where you get a big lift, right?”

“If you're in the zone and I think it's harder than ever, I think, but if you're in it, there is just unlimited F and capital, right? But you got to be in that box.”

“Any deal where you have a hundred percent conviction to Vivex, you should do it.”

“there's not as much innovation in the true enterprise. Not B to B, not mid-market, but gnarly big problems. It's just not what all the kids in SF know, right? And so there's always going to be less investment with A and S tier teams solving gnarly enterprise problems, especially outside of security. There's just going…”

“one to 10 and five quarters or less is S tier. One to 10 and five quarters or less. And so that's, that's, I, I think I, I copied that with attribution. I, I used that as my investing, uh, yardstick for years, right?”

“It's going to hurt you for new customers. Because it's a weapon for the sales team to use against you. I say two percent, like even just churn, you know how much work it is to change payroll providers? It ain't worth it.”

“Look, in the old days of SaaS, we all kind of grew at the same rate, so we used AR multiples, ok? But now you have to use forward AR multiples, forward revenue multiples.”

“You gotta let your vendors screw up once every five years.”

“The legal and fines, you take a reserve, and the truth is it doesn't really matter because it's, it's not a forward impact. It doesn't really tell you where CrowdStrike's gonna be in five years, so the markets usually shrug it off, even though Again, it's, it's a lot of drama.”

“All the best salespeople ask that question. On a first discovery call, Harry, when I'm meeting an enterprise customer, so tell me, is, is this purchase budgeted for this year?”

“Well, I actually find it happens by a couple million in revenue. You often will get half of your deals from not just inbound deals, but folks that heard about you. Folks that in your little niche, in your, in your little niche that have not, not in the grand scheme of things, no one's heard of you. But other folks,…”

“I think that the tough thing is we've learned that, uh, we've learned you've got to sequence these next acts. Like HubSpot did. And if you don't, uh, it's just, it's so hard to do it later. It's so, it's not impossible, but it is, it is so hard.”

“Two good ones, really good ones a week, and if you're lucky if you get an insane one a month.”

“Basically you need to get above 20 to make money. And then, or Coachella, but once you're above 20, it, it becomes, I'm way oversimplifying. Then, then you get, start to get very high margins, but it's very high. So when you look at the public companies in the space, they do have like 30 to 40% operating margins, but…”

“you should never do anyone where you can't see the future through the founders.”

“As you approach 10% market share in your core ICP, your core market, you gotta expand.”

“What I have seen in my, especially the last 24 months, but across my whole career of investing for 11 years, is there's usually only one investor that will stand up for you.”

“if you had the one, if you had, if you were the lead in Datadog or Stripe or whatever, if you had one true epic outcome, it was just true when I started to say that carries you, because then people, they believe you can do it again, right? That you have the secret sauce.”

“you gotta judge your growth, not on an app, just on an absolute basis, but compared to your competitors.”

“The last thing, and they'll, they'll cut corners, and they'll invest in someone that didn't finish high school, and they'll invest in the 10,000th, whatever, but if they're, if they perceive an edge, they'll take the risk at the, rather than the person that slugs to the office seven days, you know, VCs four and a half…”

“I haven't found I can see it early enough to take action. You can see who the winners are. There's time to see who the winners are, right? No question. But that, that edge of the, the curve, right? The inflection, the exponential growth It's, it's beyond, it's too late it to, to either write a check or do anything.”

“As a founder, your job is not to run out of money. If you got eight million instead of two million, it's not to spend it all.”

“Most funds, I mean, when you're big, it's different, but most funds that aren't huge have a few core anchors, right? They really do. And typically those relationships are trust driven, right? They, they are trust driven. That's why they're anchors. The rest, it is transactional”

“It's an easy job and that it's very, very slow, but it's very hard to get good at it, right? It's very, it's, it's, it's, it's, it's another order of magnitude slower feedback loop than venture, which is, which is pretty slow.”

“The more crowded a category, the later I would invest.”

“Each round was probably an order of magnitude harder to raise than the last. It's supposed to be a winnowing.”

“Like it takes 10 years to get a billion dollar exit, like M&A. I don't, IPO can vary. It's 10 years for, so the market's going to change a lot in ten billion, right?”

“If your fund size isn't huge to win in venture, like you need a real unicorn a year with large ownership and the math is magical.”

“as folks that have gone from CEO to VC, you got about two years before you'll understand the problem, right? You'll understand the problem, but not necessarily what's next generation, right?”

“you lose a year with every bad VP. You hire two bad VPs, you might lose a year and a half.”

“When you build a relationship, it goes better, doesn't it? It goes better in the tough times. There's more honesty. There's less baloney. And so when we skip that step, We just never have that relationship”

“What makes them Tenex, and it took me a long time to figure this out, they can change their playbook. 90% of sales reps, and this works out the bigger you get, they sell exactly the same way.”

“And then at scale, we end up at these three X, four X, five X numbers, right? Which is quotas are an SMB. Usually three X, you're fully burdened comp. You're on target earnings, you're OT up to five X in the enterprise. That's the way it works.”

“North of 20, thirty million in revenue, you're lining up so many deals at the same time that long sales cycles don't matter because if you have a hundred deals in flight, it actually starts to happen very predictably, right?”

“you do need to reinvent yourself every four to five years. And the only way you can do that is if you kind of reinvent the team and your mission, not your mission, but your strategy every four to five years.”

“you're lucky if half your VPs not only do their job well, right, but do more than their job. Like, carry some of that load, and if you can even have half of your management team do it, that's like magic, and I realize he's right”

“I think you can really only be so upset with them once or twice a year. Otherwise it's demoralizing and people quit. But if every six weeks your VP of sales, that's a little bit behind has to report, Harry, my plan for Q one was ten million. I'm at 8.4. Here's how that forcing function for you not to have to do it…”

“especially if you're a small fund, if you can't package your investments up for the next round, you have huge risk because you have to carry these companies.”

“the lead has to carry the company. And the non-leads don't. No one's expecting a non-lead to write another check into the company, but everyone's expecting the lead to write another check.”

“asking the CTO what they, what, what frustrates them and their product is very telling. The great CTOs will answer in 60 seconds.”