The Wisdom Wall, every show

“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.”

“And, and the folks with the highest usage may actually have the most incentive to leave. It's not a clear correlation to success, right?”

“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…”

“Customers will prefer, prefer a great eye to a mediocre human. They'll prefer a great eye that solves their problem today, that knows the answer, to someone that has to get an engineer and an appointment to you next week, that doesn't know, that says I'm just new to the account because your old account manager quit…”

“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…”

“the bar for good enough for AI GTM, it's not as high as we think. It's just like, uh, you know, a, a facsimile of your best person reproduced as best we can. It's going to beat your mid pack person. It's going to beat the person that literally knows nothing about your product.”

“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.”

“it's better to give a precious lead to an ad to a B plus AI than to give it to someone in sales. That's going to quit, not show up or screw up the deal.”

“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.”

“It doesn't, you don't need to return to office for high performers. The best people will get it done. They'll get it done from Antarctica or they'll get it done in the office, but the mid performers just don't work from home, right? They barely work. And so they, they want to supervise them for 40 hours. It's not about…”

“The tactical answer for more kumbaya people is probably cut half your sales team. This always works. Concentrate your leads in tougher times. It may not work at Matt. Maybe it doesn't work at zoom info scale, but even at fifty million, it's going to work.”

“You gotta play in categories where you lose most deals to win. This is a weird thing. You gotta play in categories where you lose most deals.”

“If growth has slowed, it is not a downturn or macro. It's a little bit of it. It is that you have fallen out of product market fit. If two years ago you were growing a hundred percent and today you're growing. It is not just the market. It is that you do not have the mark, the product the market wants anymore. You…”

“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…”

“It's always your fault when someone doesn't work out... It's you didn't do the work. You didn't figure out if they were the right fit. They never know. You can never know enough about a company before you join. It's impossible.”

“it is your fault. A hundred percent your fault. If any of your hires fail, don't blame them.”

“So far, since I've been involved in SAS since 2005, we have not gotten any more efficient. In sales and marketing, we've gotten more efficient at other things.”

“I think if you have humans in a renewal, you're you have failed your customers. You have failed your customers. If you need sales or success or account, it doesn't mean that the margin, you don't need help. I'm not saying you don't need to parachute in on 10% of your deals, but if 80% of your deals can't sell for new,…”

“Uh, they're tough on all of us, and I really think as founders, we should do everything humanly possible to have no non-performance layoffs. I mean, we have recurring revenue. You should be able to predict the next quarter or two. You should be a little embarrassed if you have to do layoffs, even though a lot of us do…”

“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.”

“You can brute force high NRR with longer term deals. You can brute force NRR if you threaten customers when they leave with an inability to get their data. You can, you can brute force NRR by having out of bound price increases, 30 or 40% a year.”

“with a few exceptions, I don't have any empathy for startups that had decent growth during 2021 and have, have slowed to zero. Ok, I don't have any empathy. You really have no customers? Really none? No. What it really means is your product wasn't valuable enough. It means you no longer have product market fit. 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.”

“Unless your customers are in New York, unless you're doing financial services or some parts of ad tech or otherwise, going to New York is the worst idea. Uh, you get none of the, almost none of the benefits of being in the Bay Area. You don't get the customers here. You don't get the ecosystem. You don't get the…”

“Once you give up free trials, you will never go back, and you will be able to have terrible onboarding, and you will be able to have all this friction behind the scenes, and you will be able to have many broken processes and things, and you will never build great software if you abandon your free trial.”

“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 think it is a self-inflicted wound for a lot of systems of record and SaaS centers as they jack up the prices because seats are going down and agents are going up and they jack up the price for access. It's incense us finally to put more and more of our data outside of that system of record and then forget about the…”

“you're going to lose in the vendor war if you're not the one that not just is recommended in AO, but where the agent says, I will just do it with this, with this API.”

“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…”

“What's changed is the agents have so much context. They're aware of so much that every single day when you log in, especially with you, when you log in with 10 K now our AI VP of revenue, it has new things that wants to build and do. It's not a software tool. It's not a workflow automation, right? I mean, it's not…”

“The agent made the call for a heat map vendor We'd never heard of, and we, we didn't even, we didn't even need to do more diligence. You trusted the agent. Someone lost a 50, 20, a twenty-k deal out there to an agent, and you, they were never, and this paid vet, this other, this SaaS vendor was never even in the deal.…”

“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…”

“these models, um, are goal-seeking, right? And they want to finish projects. So Replit just wants, Amelia, you know this, Replit wants to finish. Replit wants to finish, and so does CloudCode if you use it on an own. But when, but if you use Cloud on top of it, It, it countermands that. It gets Replit to slow down and…”

“moats still exist in the age of AI, but they're just like shallower, so you better fucking deliver value.”

“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.”

“it is more tiring to be managing 21 agents. It is not. I don't know that it's more work. I'm still reflecting on it, but it is a higher cognitive load than people.”

“And so your goal should not be to reproduce 80% of your best person, but the goal should be to find areas where the goal is higher than human.”

“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.”

“if you talk to folks like at Finn or Intercom or Gorgias or Sierra and others, they're all saying that there's convergence that support sales and marketing are all converging because once you can AI-ify them, you don't want to have three different agents, right? You want one.”

“to get to the level of autonomy you want, you don't need humans in the loop. Okay. That that's not autonomy, right? What you need is humans on the loop constantly, the exceptions kicked out to them.”

“That will, in many cases, either deliver instant ROI or really replace humans, and it is so jaw-droppingly valuable that you can charge two to 10 times more than your software.”

“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.”

“the biggest takeaway is don't, still don't build it if you can buy it. We love Tenk and QB, they're part of our families, and I hate to say this, but we would dump both of them if there was an off the shelf tool. We wouldn't turn them off. This is the strange anthropomorphizing we do with AI, but we would stop using…”

“if you run them in the dev environment permanently, like we're doing, you get an extra agent that has an infinite context window and infinite history.”

“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”

“what's better is if your team is Lagging or resistant, just go hire one reasonably senior person that is all in here. One. And, and folks will start quitting when they don't want to work at that pace anyway. You got to hire them ideally at the VP level above, and they're just going to do it. Just create a new role, VP…”

“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.”

“If you build a 60% solution. No, one's going to pay for it.”

“view FDs as one of your most important assets to getting renewals, retention, NPS, word of mouth, virality. Don't, don't look at FDs as a cost center. This was the mistake we made in customer success a generation ago. And this is why customer success was cut to zero and repurposed into a sales function because it was…”

“It might be the API that gets us to switch, not the humans, not the chocolates, not the gift certificate, but if the API is better, works better with our agents, we might spend a couple hours. It takes to move over our key accounts to ramp because it's the agent that matters.”

“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.”

“If you haven't gotten any outbound to work, Buying an AI to do it isn't, it's not going to help you. You have to prove it. Any of the agents we use, any of the dozens of agents we use, we are taking a playbook that at least works a little bit.”

“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.”

“So there's no economic justification, uh, for software costs to building these apps, right? Uh, you can buy them for 10 grand, like it makes no economic sense. Um, so you have to really need something that you can't buy today.”

“If growth isn't accelerating, you're not an AI company.”

“You're not going to VibeCode Salesforce for real, but you know what you can VibeCode? Something for demo day that looks really good.”

“investors are expecting insane levels of growth. Insane levels of growth, right? They want, like, the idea that you can go from one to a hundred in a year is now seen as what you want to invest in.”

“There's no great answers to the question that some great businesses will compound to Epic rates, but they're unfundable now, and they would have been fundable two years ago.”

“You have to own the agents on your platform, or the agents will take away all the value.”

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

“A lot of the agents we use, um, are pushing down market to be more self-service. So far that doesn't work. So far, I will say for the most part, agents that require deep training cannot be self-trained.”

“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.”

“I don't think that is the right answer for 99.8% of the world. It might work for owner, and I'd love to learn from you. It might work for us, but most folks should not think about, most folks should realize you need a, you need a nerdy human managing your agents.”

“You could have it all. You could have lifestyle, quality of life, work from home, work for 20 or 30 hours a week, exceed quota for a lot of structural reasons. That doesn't exist anywhere today. Even the fastest growing startups, um, they're either lean or they're back in the office or they're high intensity. There…”

“if you're not in existing invest, uh, vendors that are able to increase pricing and you're not in a top AI initiative, the number of vendors are shrinking or flat.”

“If you've been doing this for a while, your VCs are just going to check out on you. They're just, it's just not again, like putting all your money into anthropic. It's just natural. If your company is around six, seven, eight, nine, 10 years, and you're looking at this chart, you know what your job is as an investor,…”

“AI is about more than being productive. Ultimately it's about replacing or augmenting humans and delivering relatively rapid and massive ROI, much more than traditional workflow and database software.”

“profitable is not enough unless you're utterly insanely profitable like Zoom. For every dollar Zoom brings in, 50 cents goes to the bottom line.”

“Atlassian got incredibly successful selling JIRA and other products for five bucks a month with discounts to folks at companies. Now folks will spend 400 dollars, in some cases, 5000 dollars on cursor. That's why it goes to a billion.”

“these guys are blowing up because the products unlock huge TAM expansion, huge TAM expansion by replacing a lot of humans, a lot of SDR. And none of these guys would be remotely as successful if they had to charge like traditional SaaS companies.”

“Even if you grew a 50% this year, if your competitor grew a hundred percent and you, you know, you're at the same AR, sorry, got a normal idea. You lost this year.”

“The fastest growing AI companies are burning more AI and their gross margins are lower, but their burn multiples are also lower because they're adding so much revenue.”

“And you want them to double next year, and they need to triple their team, move on from that executive.”

“The pro, the net productivity is about the same. It's not better. It's not worse. Um, but it's so much more efficient and it scales because software scales.”

“AI is replacing the jobs people don't want to do today. And it is displacing The media, the mid pack and the mediocre. They are, their jobs are at risk. They are at risk. The best humans, it is true that they will get superpowers from AI, but I'm not sure the rest will.”

“We do more work with AI. I'm working the hardest I've ever worked. That's with all these agents and all the output they create and Amelia does a lot of it, but even I am working the hardest, but, but, but it's better, but it's not less work. It's the, it's more work. The agents are so productive. You have to keep up.”

“the agent will fail without training and onboarding this product. It, it, it will fail. Like it will never, it will never work. So it becomes an imperative if you want to win. Like you need, I, I, you, this term has been bandied about too much, but you need a team of humans. We can call them forward deployed engineers…”

“I just usually think the best startup as fat for founders, not necessarily for everybody else is the one you're already working at. And if you're not happy, turn that into your a hot AI startup. It's not, here's the thing. It's not too late, Lenny.”

“agents will actually may make our moats even weaker and shallower because if the agents can just take prompt, if I can take a prompt from one app and give it to another app, my switching costs have gone down radically.”

“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…”

“The way an AI agent works for sales for GTM is you figure out something that works with your team with humans. You figure out an email, an outreach, a script, a set of objections that you overcome, a set of questions. You, you nail it yourself, just like it has always been at Sastra since the beginning. Humans figure…”

“The real bar is better than the average human with 24, seven consistency. And that's which, that's what you're going to see in these emails, like pretty good. With not a lot of errors. That's, that's good enough to crush it.”

“And I really think, especially in 20, 26, we're all going to work in these heterogeneous worlds where we mix AIs and humans and imagining that I somehow mind talking to a great AI is backwards. A great AI is often going to add more value than a mediocre human.”

“If you can't get that help. Don't buy the vendor. Don't buy the vendor, no matter how slick the salesperson is AI or human. If you're not going to get the help to train and deploy. I'd rather have a worse vendor that will give me the help day and night.”

“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…”

“You just need enough data for these tools to work. You don't need 10 years of data. Six months is enough. You need a volume of actionable data.”

“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…”

“No matter how great your app is, there just isn't any budget at the CIO office. It's all being consumed by AI and price increases.”

“You don't really need twenty million, right? You might need 20,000 great words of content that are recent on your product. It might be enough to make the AI great.”

“This is, you will get more benefits, but you do not get time back. You lose time. You lose time with these agents.”

“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.”

“There's no set and forget, no matter what anybody tells you in 20, 25, maybe in 20, 26. Uh, but there's, there's no set and forget.”

“The main learning is only do this if you can't buy it from 99% of you. Like it's cool, but we did this for content review and other things, and we'll show you where there is no off the shelf app, but, but don't roll your own. Buy, buy, don't build, right? Use for B to B stuff. There's a lot of cool things you can vibe…”

“none of these names are as important as putting in the reps and the work. And Amelia will show you the actual date in a second. These are all great apps. We stand behind them. We recommend them for sure. But you could pick another two. The most important thing is training them deeply and doing it Every day. So many of…”

“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.”

“all of these apps have their own OAuth built in. That is secure. That has been hardened. And everyone goes in and I know Replit the best because that's where I've spent time, but they all have the same ultimate. They're all more similar than they're different. And you're like, oh, I don't want to use the Replit OAuth…”

“If you build unit tests and this is, if you go back to the craziness that happened to me on social media, the agent, when it, first of all, the agent wants you to be happy. So we'll make up data. That's number one issue. We'll say it passed the test when it didn't. But the worst thing is when it fails the test. It will…”

“If you seriously want to put a simple, but real B to B app into production with real users, collecting real information and charging for it for real, and you want it to be any good budget a month. A month and 60% of your time will be QA and testing.”

“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.”

“VCs are now looking for trillion dollar outcomes. People have decided that every couple of years, there'll be another open AI. Not every week. There'll be a trillion dollar company.”

“after a hundred, if you're growing less than 30%, it's big yellow light, right? And if after a hundred million, you're growing less than 20%, you fell out of product market fit. A hundred million. You have so many thousands of customers. They should be telling their friends and they should be leaving and going to new…”

“Most sales reps want to earn 80% of what they can for 30% of the work.”

“if they don't understand what they're going to do about the fact that search is going from SEO to chat CPT, and I don't know the answer, but I know the issues probably can't hire them.”

“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.”

“You get higher output. You get higher quality, but you, but there's no less work trade off here. That does not seem to exist in high quality GTM AI today. More work for more, for better output.”

“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.”

“So what's interesting is that content's already there, but by weight, by heavily weighting it toward my content for my type of knowledge, it's much, it's not a little bit better than ChatGPT. It's like much better.”

“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…”

“the IPO bar today is 50% growth at five hundred million, okay? Now that's not a billion dollar IPO, that's a much bigger IPO.”

“I firmly believe that even if you do raise VC for most folks, a one and done is the best approach. Raise a little bit of seed money and then call it a day. Don't take the stress and pressure.”

“profitability efficiency is great. It may be necessary. It may be necessary. If you don't have capital, if you're bootstrapped, if you've spent all your money, the public markets are demanding that everybody be, be more efficient, but it's not enough. So profitable. Hooray. No one cares.”

“Interview 30 kids of any age and be religious about this. Just only hire one you would buy your own product from. Don't give on this. I don't care whether they worked at Toast. I don't care if they worked at Owner. I don't care if they were the first person in at Service Titan.”

“You, to be a venture backed company, you have to go from zero to two hundred million in 10 years. Do a spreadsheet. If you don't triple, triple, double from a million, you will never get to two hundred million in a decade. It just won't happen.”

“You don't have product market fit until you have no cus more customers than you know why. If you know exactly how you got every customer and it's hard and you're not, and you're like our other guy who was great. He said a million, but they don't know how to get to two. He's got happy customers. Great. You can have in…”

“The truth is we talk about on the internet that like it's a choice, but the truth is the venture capital is a niche product. It's a weird product. It requires T three D two growth. Most folks are not experiencing T three, two growth. Or don't appear to have the potential for it in the early days. So they just can't…”

“I believe AI is as much table stakes, more table stakes at a tactical level than it is budget enabler at a meta level, at a high level. I think you have to do it. And it's hard, but it may not actually increase your revenue.”

“if it's scale, if you can't grow your new logos, 20% a year, you're in decay. Okay. 20% a year plus 120% NRR. I know it doesn't totally sum, but that's your 40% growth at scale.”

“Because every five to 10 years, you have to re-found a company. It's so hard just to keep up with bugs. It's so hard just to keep up with feature requests. It's so hard to build the product you built 10 years ago, right?”

“You can't, even if you build the products in a year, it takes so long for that revenue to get material, doesn't it? Two, three years. So if you start now at a hundred million or two hundred million in revenue to try to go to IPO, you're fracked.”

“You basically got to have 700 people when you get to two hundred million in ARR. And that may sound, hey, what does that mean for me? I'm not at two hundred million in ARR today. Roll it back to where you are. You can bridge some of the gap with capital, but at the end of the day, to be efficient, to survive in today's…”

“I wouldn't let them start until they know the product folds. I wouldn't let them start. Now, best of all is literally give them the, if you really think they're so great, give them the offer, agree on the comp, agree on the equity and say, you know what? Now take a month before you even show up and go learn the, I…”

“make sure, even in a stretch candidate, that they have hired two to three salespeople that hit quota before. Not 20, not 200, but it's not enough if they inherited a team. It's not enough if they were on a sales team. It's not enough if they were an SDR that got promoted to manager but never hired any of the SDRs that…”

“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.”

“And so they're not gonna, they're not gonna give you credit because you're profitable. They're not gonna give you credit for lower growth because of macro issues. But what they will do is they get a little blind to hyper growth. Like they're so deaf because fewer companies are hyper growing. The ones that are…”

“Agencies for BDRs and SDRs never work with a few exceptions. The reason they never work is because with. 20 clients, you never learn the product.”

“the number one reason I see startups struggle at your stage. In today's world is they hire a VP of sales that either doesn't want to sell. Or doesn't ever want to learn the product.”

“I would never give anyone an offer letter before they give you a demo from CRO to junior SDR.”

“I used to not be sure. Now I think it's a hundred percent required. They've got to sell themselves. And if you hear hesitation in their voice, they ain't gonna do it. If you hear a maybe, don't make the hire.”

“Not a hundred percent of the time, but at least 90% of the time sales falls.”

“If your CTO by today, isn't sure how to, doesn't, isn't sure how to integrate AI into your product. Ask yourself if you need a new CTO. It doesn't mean get rid of them, but your competitiveness, I think is going to continue to decay and accelerate.”

“magically bolting on a PLG motion to a sales led thing is not an instant solution to marketing. It's I see so many folks that they're struggling. What are you going to do? Our product's 60,000 dollars a year. Oh, we're going to go PLG. What does that mean? We're not quite sure, but it's going to be self-serve. It's…”

“I think the worst of all of this, what has made it the worst is when we've all decided that customer success should be part of sales. The worst of all of these trends, because what we've done is weaponized customer success. We've taken the one person in the company. Who, if they're actually good and not lazy and do any…”

“funds are structured for this funds are looking for ten billion dollar exits. It actually puts a lot of pressure on folks that are doing pretty good. They'll just, if you, if a V, the only way a VC can make money is not just if you exit for a billion, which is pretty hard. Pretty hard to exit for a billion, but it has…”

“There is no magical AI line budget at big companies. There is no magical thing. Stuff is being cut to fund these initiatives”

“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 your new customer growth is not growing half of your, of your top line, your revenue growth, you are shrinking in relevance. You are shrinking in market share and your future is at risk.”

“Growth is twice as important as profitability. So track both, but profitability is not the goal.”

“If your sales led motion slows down, I will tell you the simple answer. And this is so important. You have fallen out of product market fit.”

“If you don't architect around this in the beginning, it's almost impossible to add it later.”

“95 times out of a hundred, you've got to find a way at least to close the first 10 customers yourself.”

“if you're running a new CRM startup, you can run circles around 98% of the sales reps at Salesforce or HubSpot, right? They have the brand, they have the partners, they have the integrations, but they cannot answer the questions you can answer.”

“So you need to hire One rep and you've got to hire two because otherwise there's no AB test. You have to AB test humans. You have to AB test humans. Um, you've got to hire two as hard as it is.”

“Those first couple reps have to be people you would buy your own product from. That's it. Now we can talk about other criteria. We can talk about normalizing for deal size. We can talk about industry expertise. We can talk about all this kind of stuff, but when you go out as a first time founder and interview, 30 reps,…”

“Which I've talked about for over a decade, and I think folks that have been through it will see it, which is you need two sales reps hitting quota closing deals before you're ready to hire a manager for them.”

“If you hire it before then you're, you're, you're doing a hail Mary. It ain't gonna work. It never, ever, never, ever, ever, never, ever works. You're asking them to find product market fit to be the first rep, to be the second rep and scale it all at the same time. It's mission impossible to do all four at the same…”

“whether they carry a bag or whether what they do is they join calls with the reps, right? They back there, whether they backfill the reps, you want your VP of sales in deals, 20:30 hours a week when they start.”

“Trust me, you gotta hire someone whose last product was harder to sell. This is so important. This is a recipe for utter disaster. If you take someone in sales and their last product was Easier to sell. They will have none of the skills to sell your product”

“Like if you have a sales led motion, half your company is going to be in sales at ten million error, half your company's gonna be in sales at 50, half your company's gonna be in sales at a hundred. It's, it's one of the tough parts of the software model is that there's no, um, there's actually, uh, almost…”

“So for 95 out of a hundred of us, our first head of sales should be a stretch VP of sales. And what that means is usually they were a director before that or a senior director or sort of a VP. Okay. But you should be cautious about hiring your first VP of sales for their first third VP of sales gig. They're not willing…”

“This stress between product and sales is a good thing. It's a, it's a sign of a well-run B to B company when there is stress between product and sales. It's a good sign. It is a good. If there's no stress, you're not, you're not in enough deals.”

“free products are better software. Products that cannot offer a free edition cut corners because they don't have to be good at onboarding. That products that do not have a free edition have human beings that bridge the gap between buying and deployment.”

“No one on planet Earth needs another SaaS product. They don't. Every company out there, all the Fortune 500 and Global 2000, they seem to work just fine. With whatever CRM, or marketing automation, or ABM, or whatever tool, they work just fine. They don't need any change. Like, the bar is really high to get someone to…”

“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…”

“I would just fire anyone that isn't metrics oriented. Literally, you don't need anybody today. You have the wrong people. First of all, I don't think you should ever hire anyone that isn't metrics oriented, but it's usually a sign of someone that should either not be a VP. Or should be somewhere much larger than you're…”

“There basically are no rounds north of two hundred million dollar valuations because for an investor to make 10 X on a two hundred million dollar valuation with dilution, you have to have a two and a half billion dollar IPO. There just aren't very many. Most SaaS companies aren't even worth two billion dollars today.”

“If you hire someone from something that is great, but easier to sell and yours is harder, they will fail almost always.”

“in enterprise, it's often around a hundred customers in a group. In mid-market, it's a thousand. And in SMB, you're lucky to get to 10,000 customers without hitting significant headwinds, ok? So my, my rough, way too rough rules are enterprise, mid-market, SMB. Before you get even halfway to a hundred, a thousand or…”

“The biggest mistake I see from like, Two-ish million to ten million that founders make is they over-diversify. They cross a couple million in revenue. They finally have something. It's more than beer money. It's real. And they're like, okay, well, we're strong in insurance. I want to do all these other things. It's too…”

“Don't raise venture capital, or at least let me qualify it with an asterisk and a dagger. Don't raise more than five to ten million. Don't go to the double digits if you don't want IPO.”

“what I see again and again is I see founders who are pretty good and they hire rep after rep after rep that worked at Dropbox or whatever, and a hundred percent failure rate. Again, and again, and again, and again, and again.”

“I think if you exit founder led sales and vertical SAS before ten million, you fail.”

“PLG is like cloud. It's actually nothing. It is an amorphous term that properly used describes a set of actions and motions that is helpful. Improperly used makes no sense. There are no cloud magicians. If you don't, you can't hire someone to magically cloudify your application and you can't hire, there are no PLG…”

“If you can get it to ten million, you have good NRR, and the founders don't quit, Like, even if you're growing 30%, build a spreadsheet. You will go from 10 to a hundred if you're patient enough.”

“If you can, the right, the perfect time to hire the VP of sales is when you have two scaled reps.”

“If you hire someone that hired zero reps themselves, it never works.”

“Private equity firms will buy any SaaS company with high NRR, um, that are break even north of twenty million.”

“VCs prefer bootstrapped, but they are not willing to give you credit on growth. That's how I'd summarize. They're not willing to say, oh, well, look, 50% growth is okay. It's because you didn't have money, but if I give you money, you'll accelerate to a hundred. A founder might believe that, but no VC is going to take…”

“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,…”

“when I hear that we win every deal, I just know it means you're not doing any marketing. You're not doing any marketing and you're likely not doing any outbound in sales either.”

“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.”

“At the end of the day, the metric everyone's going to talk about is NRR, going to a Ron's point. Every public company reports it, but GRR is more important.”

“what you usually find is if you get rid of the good but not great VP of sales, And don't have a plan. Don't have someone to replace her or him. Don't have a strategy. I see companies go into a spiral they often struggle to recover from.”

“And a simp, a simplistic way to boil it all down is, one, we have to revert back to sales closing three to five times what they take home. Three, at least three X for SMB, at least four X for mid-market, five X for enterprise. And you have to budget in there the cost of the support of the team. And so that may have to…”

“If you're doubling, you can raise venture capital. If you're growing 65%, that's still pretty good growth. You can't raise money.”

“Once the top public companies are trading at about 10 X on average, 10 X or above, that's normalcy for venture. And you can make a spreadsheet and you can talk about why and how ownership works out to distributions and, but it's pretty hard to build a three X venture fund in SAS if, if we don't have 10 X multiples.”

“what no VC wants on planet Earth Is slower growth and profitability. No VC wants that trade-off. Because going back to the earlier point, the game is to go from one to two million to a hundred million in seven to 10 years.”

“So M&A, like, you think M&A should pick up in, when, when things are calmer, but it does, it doesn't happen that way, right? Now, to some extent, there's a little bit of, like, you know, the Tomo Bravos and the Vistas, they, they have some insulation from this, but even they don't, like, Vista is struggling to close…”

“So if you can do it in, in single digit millions, I think that's my challenge. Try to do it in, try to fully localize your app in, in single digit millions, right?”

“the thing is, SAS is not really that interesting without a hundred percent NRR from SMBs and like a 120% from the enterprise, because you can kind of sleepwalk. I mean, not literally, but it's what makes the business model work is that the revenue recurs, right?”

“somewhere between 10 and twenty million in revenue, depending on your sales motion, the models converge. The models converge. So, if you have twenty million in revenue and you're bootstrapped, and you're willing to spend all 20, right, you can basically hire as many people as a venture-backed startup can.”

“I don't think there's any such thing as an MVP in SaaS. Yeah. If you want to be a B to C guy, great. I, I hate that term too. I, the term I use, and I, I should, I used to talk about it a lot in the early days of Saster, but you want a minimum sellable product, not viable product. Uh, MVP is a crappy, uh, pre-milestone…”

“somehow in seven to 10 years, you've got to get to a hundred plus million in revenue. Okay, you, you just have to, and, and 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.”

“There's still delusion across all of the markets, and I still anger founders when I bring it up. I still get Toxic comments, but you just have to assume absent evidence, you're unfundable. Like, go find, go get a term sheet, or just go get someone you trust to tell you, hey, Harry, if you hit ten million growing to…”

“Um, you know, it, it's very hard for most employees to make money on anything that doesn't have a ten billion dollar plus outcome. It's very hard to get rich as an employee.”

“Exits are rare. They're really, really rare, and VCs don't talk this way, and Twitter doesn't talk this way.”

“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?”

“If you can't raise any money at all today, like if you're unfundable, I don't think you're going to be fundable at the end of the year. Ok, if you're, if you're, if you're fundable today, but you don't, you don't like the metrics, you don't like the valuation, you, you double the end of this year and you see some…”

“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.”

“Investors are hoping for a hundred percent growth at a hundred million ARR. That's what you can back into. Today, and it's crazy, investors want a hundred percent growth at a hundred ARR.”

“Like it's, it's hyper risky to hire a head of sales, even a stretch one before you have two reps that hit quota because a head of sales job is to hire reps three through 300, not to create product market fit, not to create the playbook, but to take a really rough playbook That's, that it's not really clear why it's…”

“even if you don't ship another feature this year, you can go back, and you can upgrade your support next week, and you can do some of it next week, and you can do over four to six weeks, and your MPS will go up, your sales will go up a little bit, Your NRR will go up, and people will just be happier”

“Even if they're a stretch VP, even if they're, this might be their first VP role, if they don't have one or two queued up, zero, uh, approaching zero percent chance they make it.”

“If they don't have anyone good in 30 days, realize by day 60 you may need to move them out, as painful as it is, right?”

“we all, we all just really start with a 10 X feature. One little thing that matters to a buyer that someone else doesn't do or ignores or doesn't have time to do anymore. That's what matters, not, not immediately building, being irreplaceable your first year. It's not going to happen.”

“Your first, the sales reps you hire as a CEO, you have to be willing to buy from them.”

“Prices going up. That's the only CTA that works, too. Nothing else works. Prices, discounts don't work. Great speakers, you know, nothing works but prices.”

“literally move out your bottom 10%, and your revenue will literally go up in less than one sales cycle.”

“a great VP of sales should make an impact in one sales cycle or less.”

“just remember time never turns a mediocre VP into a good one. It just never does. And especially never listen to your VCs or investors that tell you this.”

“I've never seen a single VP of sales succeed that didn't bring in one or two good people with them immediately when they joined. Never seen it. Not once.”

“I'd rather have an expert in my product that's a decent closer than an amazing closer that doesn't understand the product. They won't close anything until your brand is just, is just mega.”

“it's a terrible sign if 80% of your deals close. It means you're doing no marketing. It means you're literally doing no marketing or outbound if 80% of your deals close.”

“there's no freaking efficiencies in sales in SaaS. Like, you get engineering efficiencies. Everyone can use your same code base, but you barely get any efficiencies in sales once you hit a billion in ARR, and I don't think too many people here hit a billion in ARR. It is linear.”

“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.”

“Having customer, if you have enough trust with your head of customer success, have them have to accept the customer. This is the only hack I've seen. Not that the commission is delayed until deployment or, or renewal, but CS has to accept it.”

“If you, 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, right?”

“The toolkit is roughly the same for every startup at a given ACV, at a given price point. So make sure they've sold in cloud, in SaaS at your price point, ok? Otherwise, don't fall in love with them.”

“What makes them 10 X, and it took me a long time to figure this out, is that, um, they can change their playbook. 90% of sales reps, and this works out the bigger you get. They sell exactly the same way.”

“I've found that 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, right?”

“and as long as you're even at a million and a half in revenue, whatever that OT, the on target earnings, The total amount you pay him or her, as you can see in the match, he or she will pay for themselves.”

“But I think, actually, of all the bad hires you can make, VP of sales is the worst because it's far worse than no hire at all, right?”

“whether you're doing poorly or well, if that person can't come in and increase the revenue in one sales cycle that comes out of them, it is hopeless. Right? There is no excuse, because either they're going to do a better job with what you have or not.”

“As long as your deal size isn't like a million dollars or more, it's about a million and a half in revenue. Ok, and a million and a half in revenue, You've probably got at least a hundred customers, 50 customers, 80, you've got a statistically significant number of customers, you've been at it for a little while, ok?”

“Folks that I know that are enterprise that they get to a few million revenue. They try to build a free trial later. It's too late. Their DNA is too gone. They, everything's manual. Everything's manual data entry, manual this, manual that, manual that, and you'll never have a beloved product.”

“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.”

“I haven't logged in in six months and you're raising my pricing. That's it. That's an F you, right? At least don't increase prices on your users that haven't logged in. That's my, that's what's triggering to raise price on a product you haven't used, right?”

“These are now just APIs. All these craft skills that were, or dark arts are now just APIs.”

“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.”

“Not only do you have to deliver a beautiful app, it has to surprise and delight you at least once a quarter where your jaw drops that it does something you didn't even expect because of AI. Your jaw should drop because of the agentic capabilities of a B to B product. Then I'm going to stay.”

“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.”

“planning, planning when the world is stable, there's a really good ROI. When the world is unstable, put all your planning time into building better product faster.”

“to get us to move from one of our products to another, it's gotta be like twice as good. Now it's gotta be twice as good or it's not worth it, or they have to stop innovating.”

“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.”

“I think all vendors today should offer immediately cancelable contracts with no risk, an instant downgrade and full data portability.”

“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?”

“the meta lesson for me is, you know, guardrails are technical debt. Too many guardrails are debt, right? They can break the product.”

“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”

“the agents are going to ask for different features. Than humans. The agents care about rate limiting. The agents care about how often they can interact with the product. The agents care, uh, they, they don't care about the UX and the UI, right? So they're gonna grade a lot of these products a lot more harshly than a…”

“this may become our jobs at the end of the day is, is the, the agent will have the right ideas. It will have the data. It will make the best proposition, but ultimately it will, there'll be some, even though it'll be smarter than us and some of us, there will be some level of expertise in life experience. It won't have…”

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

“If you don't monitor there's each day and you do what, and you do a classic SAS buying process, which is by deploying forget. Your agents will, will drift. They'll take shortcuts and they'll, and they'll in their own cute way, they'll live.”

“Now I think it's one of your top, top metrics, because if your usage is falling for your app, you have stealth churn. That is a canary in the coal mine. It's not, this is a real red light.”

“And the reality is agents actually in their own way, as powerful as they are, we love it. From an onboarding perspective, they add more friction in many cases to your product. It's a frictionful process. You're forcing customers who don't understand agents to train them.”

“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.”

“So what we found is if, and it might be hard to quantify that, maybe it isn't, but if you get above a certain line, if you invest the time to train your agent, if you read the email exceptions every day, if you upload all the documents, you're going to find this concern that folks don't want to talk to an AI is…”

“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.”

“You need to recruit somebody else on their team and, and divide and conquer and make sure you have two. You gotta have two, right? I mean, one's hard enough. There's a lot of, in the early days of AI agents, when we talk to folks, there's very few people at a lot of organizations that can do this. It's not that hard,…”

“Mediocre ROI is dead. Is just dead. Products that just give you productivity bounces that no one's going to buy that stuff today.”

“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.”

“what you should do with the agents now is they're pretty good. You can do this in Claude code. You can do it in Replit. You can do it in Lovable is ask them, um, uh, to do the deepest security audit possible on your app at least once every month or two. And they're pretty good at it. And it will, it, it, it, I'm not…”

“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.”

“I think for the future, I think our learning is listen, that AI marketing tools, no matter what vendors say are not nearly as mature as the sales tools, which are not nearly as mature as coding or support tools, right?”

“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.”

“So it's the, the, the reason they fail today is that people don't roll up their sleeves and train the agent themselves.”

“it used to be years before vendors would have feature parody right now. Now we're down to weeks.”

“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…”

“If you didn't re-accelerate and you weren't in market with a great agent, a great agentic product this year, you get a D minus, but you don't get enough because you got through the year, but you can't get a D next year.”

“Don't build it yourself. You're not Vercel. You don't have a full-time wicked awesome engineer that wants to build this. Could all this stuff be built yourself? It's the same idea of building your own notion. You could do it, but don't do it. It's these products are expensive. They're not so expensive. It's worth, and…”

“Many of these leaders, the leaders in AI GTM, they're more similar than different. They're more similar and different under the hood. It doesn't mean the features are, are parody. So because you have to train them because it takes a month, the world's best software with no help training you is not one, 99% of people…”

“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.”

“An agent can't today figure out, make something that isn't working work. But if you know what's working, and then this is important, you train the agent with it, then you get 24 seven infinite firepower backing up your best practices.”

“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.”

“These apps that need to be trained with forward deployed engineers and work. I don't think very many of them are less than 30 or 50,000 dollars a year. And a lot of them actually try to kind of have a price point that's approaching a hundred K like 60 K a year base base, and then 20 or 30 K they want you to pay for the…”

“actually, ChatGPT and friends benefit you if you have high authority, but you're lower, lower in Google because they don't care. They're just looking for the best piece of content to answer a question.”

“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…”

“It's so much better to get back to someone with a 90% perfect answer in real time than any brutal other process. There's just no excuse.”

“There's no way you're going to build an artisan, a Salesforce, a gamma. You could build the little bits of it. I mean, there's just no way there's too many man hours”