

8 Nov 2026 · 1h 5m · 26 chapters
A venture investor (Rajeev Dham, Sapphire Ventures) explains why the current “tech selloff” is likely a duration/ROI timing mismatch rather than a technology failure, how long a correction could last, and what it means for applied AI companies, SaaS margins, go-to-market, and investor diligence.
Rajeev Dham is a Managing Director at Sapphire Ventures (about $10B firm), with 13 years there. He has invested in companies including Harvey, Base10, and Open Evidence, and in pre-AI deals like Clay, Glean, Monday, and LangChain. Hosts: Sam Jacobs, Asad Zaman (Sales Talent Agency), and AJ Bruno (Quotapath).
AI buildout is expensive; Wall Street wants S&P 500 earnings impact sooner than adoption will deliver. He expects a shorter correction (possibly 6–9 months) versus 2000’s multi-year reset. Applied AI companies can grow fast (15–100M then 200–600M) via land grabs and customer intimacy, with margins potentially settling around 30–40% (not 80% SaaS). Best companies will keep pivoting and “agentifying” workflows; PE is constrained early in the cycle.
Anthropic’s S-1 and upcoming IPO; analog to AWS’s early skepticism; Harvey’s lawyer “beachhead” expansion; a passed deal running 90% on open-source models with weak margin path; references to Rogo (sales capacity story) and Salesforce acquisitions.
Written by AI. May contain mistakes.
Hosts share memories and reflections on the impact of Adam Robinson.
“Before we get started this week on Topline, we do want to acknowledge and share our condolences, our thoughts, our love, and our prayers for all of the folks that perished in the plane crash recently in Florida.”
Discussion on the potential for an AI bubble and its parallels with past market corrections.
“Asad, why don't you kick us off as you usually do?”
Rajeev discusses current market conditions affecting investment decisions.
“eight years, maybe even longer for some of the stocks and companies to get back to their previous trading level.”
Insights into how companies are evolving and growing rapidly with AI integration.
“the anthropic wait and see mode amongst other things.”
Explore the rapid growth and adoption of AI platforms in enterprise environments.
“systems of record or selling to large regulated institutions like investment banks are growing at rates that we've never seen before.”
Discuss the importance of unit economics and the evolving market dynamics for AI companies.
“When the capital markets are good, get the money.”
Analyze the future of profit margins in AI and how growth will affect business models.
“And I think that land grab is so important, this level of customer intimacy and holding these customers' hands, whether they're doctors or lawyers or accountants or salespeople or marketers and showing them the future.”
Learn about strategies for companies transitioning to AI and navigating disruption.
“to support the rest of your OPEX structure and throw off cash.”
Understand the challenges private equity firms face in an evolving AI market.
“They're not going to be able to afford the companies that even Salesforce is buying.”
Discusses the challenges and inefficiencies in integrating AI into business operations.
“A private equity firm hiring operating partners to go agentify a business is just not going to work right now.”
Discusses the complexities of making venture investment decisions in a fast-paced environment.
“Okay, so let's go back to like the venture side for a second.”
Examines how perceptions of growth and investment opportunities have shifted in the market.
“Growth rates are a, they're kind of a gating factor, but they're a tertiary factor as it relates to like the excitement of a company because everything is growing fast.”
Explores the difficulties investors face with capital allocation and exit strategies in the current market.
“And see if you can print beginning with a million of EBITDA a year and then get it up to five or six or seven.”
Learn how founders can navigate investor expectations amidst market challenges.
“Like if you had a company like that in there.”
Explore how businesses are adapting to new market realities and AI innovations.
“Where that's happening though, are the 2015 and 17 and 19 businesses to say, okay, do I just give my capital back?”
Understand why founder agility and rigorous diligence are critical in today's investment landscape.
“What are you noticing that people are making their decisions off of?”
Discover the key factors investors consider when evaluating founders in a volatile market.
“And so what we're looking for are people that can just twist and turn at like what speed now?”
Learn how specialized vendors are essential in navigating AI advancements in the legal sector.
“models became so good and they just quickly did that and to continue to capture market share.”
Explore the cultural changes affecting productivity and responsiveness in companies.
“Yes, it's it's you have to do all of that in order to differentiate, especially if it becomes very easy to build a UI with cloud code and serve some tokens.”
Understand the hurdles traditional SaaS companies face as they adapt to the AI landscape.
“I think there's technology, there's capability and there's culture.”
Discuss the skillset transformations required for success in AI-driven companies.
“And you would know this better than me, Asa, because, you know, you're in the search business.”
Learn about the challenges in assessing return on investment for AI initiatives.
“And so when you wonder where's the ROI, people are wondering, well, why isn't all this revenue growth?”
Explore strategies for capital allocation amidst evolving market conditions.
“I heard the Stripe founder with Sam Altman, he's like, I spent 10 % of my budget on on AI internally.”
Explore the dynamics of capital allocation and funding strategies in AI companies.
“Like if you're a capital allocator and you're doing something 20 times better to do a 20 hour fund formation doc, you can do in one hour now with heart.”
Discuss the implications of IPOs in the tech industry and the evolving landscape.
“I think it could impact liquidity for some period of time, three, six, nine months.”
Analyze the current state and future potential of go-to-market technology.
“There are go-to-market AI companies also growing at breathtaking rates at the applied AI layer.”

Get the gist, explore an idea or ask about something said.
On Topline, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00It's 100 % exhausting. I've never worked harder in my career. I've never been also more optimistic in my career. That's Rajeev Dham. He's a managing director at Sapphire Ventures, a$10 billion venture firm.
0:11Sam Jacobs: On our last episode, the legendary Jeffrey Moore told us there's zero chance this AI bubble doesn't pop. So today, Rajeev shares whether you should be bracing for that pop and how long a correction would last. I think there's just a duration mismatch. In 2000, when the market corrected, it took seven, eight years. I think it could be. We also get into whether AI models will ultimately eat any software built on top of them. We debate whether go-to-market AI can ever be anything more than a spam cannon, and how the best AI companies are operating differently than traditional SaaS. A buddy of mine, he just left a SaaS-era darling$16-18 billion valuation company, and he said, Rajiv, I thought we were innovating with AI there.
0:52This is a whole different ballgame.
0:53Sam Jacobs: Tech stocks just took a beating, and Anthropic is about to go public. If your number depends on where this market goes next, this episode is for you. Welcome to Topline. Hey, everybody. Before we get started this week on Topline, we do want to acknowledge and share our condolences, our thoughts, our love, and our prayers for all of the folks that perished in the plane crash recently in Florida. We knew Adam Robinson pretty well. He was a guest on Topline. He was obviously a big presence on LinkedIn. And I think he had a big influence on each of us. So we just wanted to share some thoughts and some memories.
1:40Sam Jacobs: Asit, I know you think and thought really highly of Adam. Any thoughts or reflections? You know, I think back to the SaaS era and of the great entrepreneurs from that era, I think he's one of them, not because of like the scale of company that he built, but because of how he built the company. You know, the things he believed in, how much he believed in them, how he was able to confidently be vocal about those things. He showed people that there was a different sort of company that you could build and what a great life you could create for yourself downstream of that. um don't have to raise venture you can take dividends from a tech company um you don't you know you can run a 20 million dollar business with like less than 10 employees like these are things that he kind of showed the market um and he was just he was a cool guy he was a cool guy who i think inspired many people and so he will be missed i first met adam actually at the ceo summit sam and i had read all about him and at the time linkedin was definitely becoming this channel where entrepreneurs and founders were trying to find their brand and their voice and i viewed at that time um adam is someone that i saw from afar being open and honest with what he was building and how he was building it and i just was skeptical at that moment in time um but i got a chance to sit next to him on a bus ride at that summit, and we talked for 45 minutes, and he was just as open and warm and vulnerable in person as he was online.
3:19And it's extremely rare to find a personality that matches who they are to their online persona. And Adam was that, and he was a great human being. And I had once or twice a year would just reach out to him and catch up with him. And the last time I did was actually last month, just checking in on him. And, you know, he was able to be that the thing we talk about in durable revenue and sustainable, he was able to do that as a bootstrapped entrepreneur. And that's incredible. So he will be missed and deeply saddened about the accident as well.
4:01Sam Jacobs: he uh the thing that i i shared some thoughts on social media but the one i'll emphasize the post that i most remember that i think about a couple times a week is um the calendar post he did a screenshot of his calendar he built these incredible businesses and he would post his financials so we always brought the receipts and you'd see like two million dollars revenue one million dollars of cost one million dollar profit in that one month you're like damn that's pretty freaking good and then he would show his calendar and there was nothing on it and uh you know it was all meetings yeah and then the rest was like blank i mean there was a few things here and there but it did not look anything looked like my calendar that's because he was spending time with his family you know he was with his kids and he was with his wife and i just of all of the different things that he inspired me about that was perhaps the biggest one that you can do all of these things and you can still have boundaries around what is your time and what is the company's time and what is family time.
5:04Sam Jacobs: And yeah, it had a really big impact on me. And of course, my wife, she's always talking about him in our house because we always dream of building companies with a small number of people that are truly passionate and not needing big teams. And he was a huge inspiration to her and her co-founder. So, Adam, you'll be missed. And rest in peace to all of the folks that died in that plane crash. It's truly tragic. And our hearts go out to their families. Well said, Sam.
5:50Sam Jacobs: Hi, everybody. Welcome to Top Line. It's Sam Jacobs. I'm your co-host. I'm joined by my other co-hosts, my good friends, Asad Zaman, the CEO of Sales Talent Agency, and AJ Bruno, the CEO of Quotapath. We've got a very special guest on the show today, Rajiv Dam. He's currently an MD at Sapphire Ventures. If you don't know Sapphire, they're a$10 billion venture firm, and he's been there 13 years. Rajiv has invested in a merger's row of incredible companies, including Harvey, Base 10, Open Evidence. His pre-AI portfolio is also quite special. He invested in Clay, Glean, Monday, Langchain, and also a lot of go-to-market tech.
6:29Sam Jacobs: And he's got a seat at the table on where AI is taking us. He understands the SaaS era really well, so we'll have a lot to talk about, including his point of view on the public market carnage of last week. So Rajiv, welcome to Topline. Thank you for having me. So let's get into it. Asad, why don't you kick us off as you usually do? I think a good place to start is actually last Sweets episode. So Rajiv, we had Jeffrey Moore on. And one of the things he said was that this is very much a bubble and there's a hundred percent probability that this pops. He didn't say that he's not an AI believer. He's like, this is really powerful.
7:04It's going to shape the world for the better. But both of these things can be true. And he compared the situation and why there might be a bubble that burst to 2008, not to 2000. He's like, this is a financial issue. This isn't a technology type of issue the same way. After that, literally the next day, Google announced their earnings. Stock dropped 12%. Over the course of last week, you had Amazon that took a hit. You had Meta that's been down quite a fair bit. Intel was down quite dramatically. And a lot of the concern the market seems to have is with the free cash flow of these organizations.
7:43And so So looking at the last few months, it seems like every couple of months, there's a reason why we have to go back and question our priors. And most of those are technical, right? Like reasoning models and then a fable. Is this, especially in your seat, one of those moments? Has this changed how you're thinking about things in any meaningful way? Yeah, no, I think that's the right question, Asad, to ask, especially at this time. You know, you're spot on. I do think that there are some trepidations in the market, but I think the issue is, as we all know, this AI buildout is just incredibly expensive.
8:23And so it's more of a duration mismatch issue. And when you look through all the impatience, if you will, with the large capital expenditures of the large players, it's more because the central question today in the public and Wall Street and all of our minds is, is there really a return on investment for this technology? And when will it come and how patient will folks be? Obviously, me as a venture investor, we see the return. We see pockets of companies, especially the most sophisticated ones. using agents in incredible ways and driving not just 10, 20 % enhanced productivity, but 10 to 20 times better productivity across lawyers and accountants and salespeople and marketers.
9:10But as you saw from the Anthropic S1, and we can dive into some of those metrics, clearly the diffusion is still early. And so when you see all of this capital outlay, it's not enough just to point to Anthropic's revenue run rate growth anymore. People want to see it impacting the S &P 500 earnings. It's okay if it's maybe one or two years delayed, but no one knows what is that duration mismatch and what is the delay that Wall Street and retail investors will put up with. Amazon 2010, don't quote me on it, but I think it was around that time, went through this sort of similar period if you look back where they were building out AWS.
9:48And there was a lot of questions at the time to say, all of this on CapEx and these facilities and compute and what. And once they started to turn it on, I think it was sort of four or five years later, you obviously saw the rise of AWS and it's just been incredible ever since. So there's some analogs there. I'm a believer. I think there's just a duration mismatch. And so if you're a long-term believer, you're going to end up on the right side. And I agree with Jeffrey. I don't think this is a situation where, you know, in 2000, when the market corrected, it took seven, eight years, maybe even longer for some of the stocks and companies to get back to their previous trading level.
10:24I think it could be a six-month, nine-month period when this mismatch needs to be reconciled, but in the medium to long-term, obviously a bull, and I think it'll end up okay. Rajiv, I was talking to some investors that fund these data center build-outs, and they have really changed the bar for who they're willing to give any money to in the last few months. There's a lot more diligence. The bar is just a lot higher. how is your bar evolved like have you changed how you're thinking about what's attractive what's not attractive which company gets money which company doesn't get money right now yeah yeah it's a good question and and by the way um to your prior question and and somewhat this one just taking a step back remember my job as a venture investor is to be a long-term thinker when we invest in a company it takes three five sometimes ten years before we exit so if we over rotate in the moment based on some market jitters and trepidation around what we invest in it could actually lead to adverse selection our job is just to identify and partner with the best founders of the best enterprise ai companies period um but yes you're right there has been some cracks in the environment both on the public side and the debt providers uh just to fill you guys in even the private markets even before the public markets had a downturn in the last couple of weeks, already some financing rounds were taking longer to fill.
11:53I was already sensing those cracks. And I think that's because - Open AI apparently had to reduce its valuation. It's taken longer - Reduced the valuation. Yeah. And that's filtering down to some of the hottest robotics companies, the hottest neolabs where I'm seeing these rounds stay open for about a month or two. It's due to the anthropic wait and see mode amongst other things. And so it has changed the bar. I think it's a good thing in that when you have a month to due diligence, you could do a lot more of it than when you had a day or a week just two, three months ago. Was it literally like that?
12:25Like, were you having to make decisions about$1 ,500 million investments in like 48 hours? Yeah, I would say a week, sometimes maximum to, yeah, two to seven days. And I mean, that also means you just got to come in really prepared. But when you have a thousand companies all growing incredibly fast. We as investors feel intimidated.
12:46Sam Jacobs: Can we double click on that? So really, I'm really curious, like all of these companies in every category that just have.ai at the bottom of, you know, at the end of the company name are growing that fast? Or there must be categories of companies that are growing super quickly, like, you know, like NeoClouds or inference companies. I mean, or is it really every company in every category? because my perspective is in B2B, there's an upper limit on growth, unless it's like some pure PLG motion. But, you know, unless you're selling multimillion dollar contracts because these large enterprises like need compute and they'll purchase it at any cost, application companies typically can only grow at the rate of enterprise buyers purchasing software.
13:33Sam Jacobs: But are you seeing something different? Am I wrong? I am seeing something different. And you're right. On a relative basis, data companies, companies reselling data or RL environments, and probably neocloud and inference platforms or investment base that are growing the fastest at the moment, right? These are the components powering this build out. Of course, I'm sure some power and other companies are going fast, but at least in terms of what we focus on. But even the application companies and even those application companies that are disrupting systems of record or selling to large regulated institutions like investment banks are growing at rates that we've never seen before.
14:11And so just the growth rate and the bar keeps getting higher month over month. These are the companies that are growing from 15 to 100 million in revenue, not 15 to 45, not 15 to 30.
14:22Sam Jacobs: And these are companies, this is consumption-based pricing where you get a beachhead into an organization and then the lawyers just start doing all of their work on Harvey and all of a sudden it's just game over and you have a lawyer that maybe was buying, I don't know, whatever the equivalent unit would be, like$100 worth of stuff initially, and now he's buying$1 ,000 worth of stuff because he's running all of his production, all of his work through this AI platform. Is that sort of how you're seeing when it works, the adoption? It's actually a hybrid. Believe it or not, at the applied AI layer, the leading companies have been very careful not to go too quickly towards charging by consumption outside of AI coding, which did that brilliantly, and maybe AICX, where you can relate it to a resolve ticket, right?
15:13Most of the other categories are charging platform fees, per seat fees, or hybrid fees. They don't want to overcharge their customers. They want to be able to relate the product usage to some level of value, right? Based on the tokens used. So that transition is still early. So what I'm trying to tell you is even just on new logo growth, not just purely expansion because consumption and PLG is going through the roof. These are companies that are going from, again, 15 to 100, 200 to 600, which is just incredible in terms of the pull and how powerful these products are, even at that layer of the sack.
15:47Rajiv, we heard a lot about like negative 50 % margins for Harvey, of course. And so what you're talking about is, what I'm hearing you say is that that in that creative beachhead at the enterprise is more important now than ever and just create value before you extract value. How much at the board level in these meetings are you looking at the unit economics behind this? And is that a big portion of your conversations of like, okay, well, we're in with these companies, but we have to actually get the scale of it right? And is there a lot of tension? What's that? Does it matter? Does it matter?
16:26From 200 to 600. Fuck it. Like, who cares? Like, eventually you'll figure it out probably. I don't know if that's true. Well, I think the reason that gives you confidence that you'll figure, there's some companies where we don't have that confidence. We passed on one recently that was already running 90 % of their workloads on open source models. And they were working with BaseNet and Fireworks to do so. And so when I talked to the CFO, I'm like, well, what are your leverage? You're already pricing based on consumption and you're running on open source. How are you going to go from 7 % gross margin to 40?
16:57And we can talk about what I think these companies will look like, by the way, at steady state. How quick was their growth at that point? Like, was it astronomical still? For the company in question that I'm referring to right now? Yeah, incredible, incredible growth. Interesting. But for most of them, there is a very strong, well, one, it's economically rational, as we just talked about. When the capital markets are good, get the money. If you can run it at breakeven gross margin, go land grab. And we can talk about why that's important. But two, there's very good reasons why. If you're running on 97 % frontier, as most applied AI companies are, you could sort of shift over and go to open source and open way.
17:33And there's cheaper alternatives, which now they're doing as well, and helping these companies post-train their own models and do all sorts of things. And then you move to consumption-based pricing, and then you have a huge amount of margin uplift. But I'd hardly know his argument to you would be like, I know we are on fireworks and base and it's still looking expensive, gross margin starts. But as we do more compute build outs, compute gets cheaper, maybe the chips get better, the compute gets cheaper, as well as whatever I'm spending on right now, open source, as models get better, that same value I'm providing my customer, I can provide it at a better margin eventually.
18:09and so believe in me, give me money now, like it'll work out. Like, is that the pitch that they have in return? Yes. Yeah. We'll have new, there are still infrastructure optimizations we can make instead of calling an open source model three times, you call it once and therefore the amount that I need to pay fireworks or base 10 is a little bit more. You need less inference from them and we'll provide new products and services, which is a reasonable argument, by the way. These products are just evolving and becoming more and more magical every single month. It's a reasonable argument for us as a capital allocator It's just figuring out if we only have so many dollars, all of us, where do you allocate your dollars?
18:44But I will say something. I do think steady state margins for these applied AI companies will just look fundamentally different. I don't know if we're going to have this 78 % margin business. It could very well be you have a 30 % gross margin business. You might think, oh, my gosh. We talk about that a lot on this show.
19:01Sam Jacobs: Yeah. And that it's sort of a wistful sentimentality about the golden age of SaaS because we might not ever get back to 80%, whether you call it software, whatever the word is for how people will use, you know, AI or code or whatever. Like your point, maybe the steady state is just 30 or 40 % margins, which maybe compared to labor businesses is still way better than having to hire all the equivalent humans that would have done that work. But it's not the 80 % cloud-based gross margins that were so magical for 20 years. But I think you're hitting on it. All that matters is bottom line. And if you could charge 30 to 40 % of$10 ,000 per person per year versus 80 % of$1 ,000, your gross profit dollars are a lot bigger if you have an AI or agent product that's doing the work.
19:55Therefore, you can cover all your sales and marketing and R &D and probably still throw off incredible cash flow because your magic number is great because you have both for your product. So that's how I see it. I think ASPs will grow by 10x.
20:06Sam Jacobs: It does put, well, you tell me, my initial reaction to that is it puts more pressure, first of on operating execution, because you don't have that much margin of error to play with. And then it just, the competitive dynamics can be really, really brutal. It's not that it's going to become grocery stores, but, you know, grocery stores operate on razor thin margins. And ultimately, there's consolidation because it's just too hard to run a standalone store. my point is yes it's a bigger dollar value of gross margin but it still constrains the operating flexibility of the business at least compared to traditional sass but maybe that's just the world that we live in what if they just continue growing at these crazy rates right like a grocery store grows at a really slow rate and has shitty margins that's like that's two problems but if you're growing at like 200 to 600 you know you just you get this different sort of leverage i think that balances it out probably, right?
21:02Yeah. And I think that land grab is so important, this level of customer intimacy and holding these customers' hands, whether they're doctors or lawyers or accountants or salespeople or marketers and showing them the future. I think that's so critical for this layer of company in order to succeed and help working with them in very nuanced ways. And so that is the name of the game and it's proving out to work. You can go so deep with your customers and know their nuanced workflows as a result. There was a story, I think, the Rogo founder told on Invest Like the Best that he presented a plan for how much sales capacity he was going to add on in the following year.
21:37And I think it was Pat Grady on the board who was like, hey, and he thought this was an aggressive plan. And then Pat Grady was like, listen, if we assume that every financial institution is going to make an AI-based bet in the next 12 months, do we now have enough capacity to be in all of those rooms? And I was like, no, we don't. Okay, so then make it more aggressive, do that. So there is a land grab that's happening. When does that end? Like, you know, that can't go on forever. So is there like a view that everybody has that in the next 12, 24 months, 18 months, everyone's made their bets? Then how does the market change at that point?
22:14Like, very curious to understand the other side of that. Because it does feel like that is what's happening right now but then when does it end i think for the best companies it never ends and let me explain what they what they look like is is a tight vertical market maybe selling to investment banking but imagine all the adjacent uh corporate banking wealth management and ria firms and and um these companies you might have all this adoption in one sub segment in the first 12 months but it'll continue on and then of course eventually you're going to start expanding and selling more and consumption and providing more value to your existing customer but i truly feel like the best companies aren't just going to sit here three years from now and say okay i'm all topped out of new logos they're going to go into new and more and new interesting areas it's so interesting i grew up in the sass era we used to tell these founders focus focus focus until 50 even 100 of air are one product product market do it well one geography it's s curves are building at five or ten of era right new products new ICPs, new models, new pricing models.
23:18Everything is just disrupted every month. And that's actually what we look for. We look for harder pivots that founders have made versus otherwise, which is completely opposite than 10 years ago. 30 % to 40 % margins is interesting given the time horizon that you cited, which was still 10 years. So the time horizon that you would have cited 10 years ago still feels like the time horizon that you're citing today. But then the question is like the multiples on these businesses, because it's so early, we have no idea what that's going to look like. And does the rule of 40, like even matter at any point in the future when these companies are at scale?
23:55So fundamentally every business, you know, at the end state trades on cashflow. My only point with the 30, 40 % is that if we do end up there and there's highly likely there's going to be services and all sorts of stuff on top, they can get to 60%. But if we end up there and if you're on a higher ASP or ACV or ARPU per customer, whatever it is, you still have enough cash dollars slushing around to support the rest of your OPEX structure and throw off cash. And if you're doing that and you're going faster because these TAMs are a lot bigger and there's pull for these agent products unlike anything we saw in SaaS, then you should really trade at a healthy multiple, right?
24:33People will probably overlook that. It's all about the bottom line dynamics and of course the growth rate. What are you doing with all of, so those are all the companies that you're investing and there's a lot of excitement now, but what about your pre-AI companies and those companies that are in like now tweeners as they become AI native and trying to figure it out everything's being disrupted at the AI level but now everything is being disrupted on the SaaS level yeah no I mean I think the the guidance to those companies and and I'm fortunate to partner with a lot of great founders there has just been to innovate as fast as you can you know I told one of my founders the other day that hey whether you grow their 300 of ARR, their cashflow break even.
25:14And I think he was drawing up a budget to grow, you know, 24 % next year or, or something like that. And I said, Hey man, like whether you grow 24 % or 18%, it doesn't matter. I'd rather have you focus less on that. What if you grow 10 % on that business? I know it's hard because you've spent 15 years building this incredible business. But do that less and work on your AI products more. Hire a COO, a private equity-like COO, just to run that business and nurture it, do right by your customers for sure, but eventually take learnings there, innovate on AI, and merge the businesses, right? Because it's just not work the incremental time.
25:53And that's been the advice. And I think, listen, I partnered with Eric at Podium. He's done a great job of that. We were investors also at Intercom and Finn, and Owen obviously did a great job. But those guys were willing to kind of burn the boats and spend all of their time focusing on the new things and then merging the businesses in elegant ways. And I think that's really what it takes. It's very hard to do.
26:13Sam Jacobs: Is there an M &A market for the company you're talking about? $300 million, maybe going to grow between 15 % to 20%, cash flow break even? If he has, if he develops an agent product, which he is, that can go zero to 20 under the hood. And now we'll start to benefit from that huge install base and all the other data he's getting from his other customers to continue to fuel a better and more agentic product in this particular market. Yes, you see Salesforce, they're picking up companies left and right that aren't the super gen AI native companies that they can afford. It's just the era before that.
26:52Is there something happening in AI? Without the AI story? So like, is there a PE firm that they're like. Not today though. Not today. Yeah, private equity firms, you can talk to them, but from my understanding and speaking with them, they're still frozen, but this is their exact strategy. They're not going to be able to afford the companies that even Salesforce is buying. So they're going to want to be able to buy this company and agentify it. But what are they waiting for? Because like you see some of these Toma Bravos and Francisco partners, etc. They're not that aggressive right now. Like I would imagine they can go to a bunch of these founders who feel like, you know, look like dears and headlights type of situations where they're like, I don't have it in me to now find an AI story.
27:31Like, give me an exit ramp here. I think there's two things. There's two things. One is they're still underwater with a lot of the large software purchases that they made and LPs questioning, what do these work? Are they even worth the debt that we put onto finances deal? We can all talk about what those names are. But even beyond that, when you're so early in a technology cycle, we just talked about how quickly this technology is moving. Like you need to be young and close to the metal and here in Silicon Valley just to know how to harness these models and figure them out. A private equity firm hiring operating partners to go agentify a business is just not going to work right now.
28:04That happens when your technology is more mature at the end of the wave and we're in the beginning of the wave. That's a really good point because the fundamental business model is still the same, which means you have less operational expenditures. So like you have less to invest in putting AI within the operations of the business as well. like less risk to take, whereas like figuring out how to get AI ROI requires some use. I think in the start, it's highly inefficient when you're trying to take any like workflow in a business. Like I look at like everything we've done with AI. In the first go of it, it's actually inefficient.
28:40You're experimenting, you're trying things that didn't work, that didn't work, tokens get lost, you know, all of that stuff. And then you find it. Then you're like, okay, here's something that works. Now let's make it efficient. This is like a journey. And And some firms don't have the ability to go on that journey right now. I would imagine these PE1 firms are those. To journey, it's about efficiency, but it's also about talent and know-how. And working with these products and technologies is just unlike anything we've seen before, at least being truly native with them and getting the EBITDA lift that they're going to need to get.
29:11But they'll open up and they'll do it and they'll get five or 10 points off the bat. I remember the term reference architecture. Once there's like an agent reference architecture that everyone knows how to plug in, you don't need to be in Silicon Valley, you know exactly what to do. And boom, you're automating a big part of your back office. Private equity firms will have a field day with that and probably pick up a lot of these SaaS companies from 2015.
29:51Sam Jacobs: Thinkific helps customer success and revenue teams build learning programs that lower churn, accelerate product adoption, and scale without adding headcount. Automated onboarding paths, role-based access for complex organizations, AI tools that dramatically cut admin time. Your learning platform should drive growth, not just track it. See what's possible. Book a demo at thinkific.com. That's T-H-I-N-K-I-F-I-C dot com. AJ, will you book a demo at thinkific.com? I always book a demo with our sponsors, Sam. On the point of customer retention, last week I spoke at Rice University and I had five takeaways from my 15 years of entrepreneurship.
30:34The number one takeaway was know your customer relentlessly. So the education part of what Thinkific is doing is 100 % aligned with how companies and startups win. so 100 put that front and foremost there asid what do you think yeah thinkific thinkific canadian company too i think so fantastic yeah fantastic terrific yeah terrific thinkific maybe
31:02Sam Jacobs: it comes from terrific you think so i think it does probably so if i had to pronounce it terrific thinkific thinking is a terrific thing so then they probably like think there we go they should We come out with a product called Think. Thinkific. We have our other sponsors that are computer. Terrific, Thinkific. Thinkific. Thinkific, terrific. Terrific, Thinkific. This episode of Topline is brought to you by Pavilion. I want to tell you about Pavilion Gold. It's so exciting. Pavilion Gold is an invitation-only community for senior go-to-market leaders at many of the world's leading B2B companies, CROs, CMOs, presidents, and executives navigating scale growth and transformation in real time.
31:43Sam Jacobs: Pavilion Gold's about a year and a half old, but our first group of 24 Pavilion Gold members came up for renewal on October 1st. I want to ask Asit, how many of those 24 people renewed their Pavilion Gold membership? Which, by the way, is not insignificant. It is an investment. I think I did my talk right before, and so I would imagine close to 100 % after this only on stage. Your talk. I was also there, Asit. Your talk. It was around. It was around. I would imagine just from the conversations I've actually had with people that are in it, I would imagine this has one of the highest renewal rates you've ever seen in your lives.
32:20100%. It is. 24.
32:21Sam Jacobs: It is 100%. 24 out of 24 people renewed. 100 %? 100%. And then there's a few people that came up for renewal through October and into November. Again, so far, the renewal rate is 100%. That's crazy. And in fact, my favorite. So here's one of the things. Matt Thompson was the president of this cyber company called SoCure. And he got recruited away to be CEO of a new company called Transmit Security. We get an email from him that says, may every day be day one. That's the subject. On his first day as CEO of this new company, we don't normally let CEOs join, but we're not going to kick you out if you were previously an operator and then you get promoted to CEO.
33:06Sam Jacobs: And so the first thing he did, literally, this is not a joke. The first thing he did was re-sign up for Pavilion Gold, and he gave his old membership to his CMO at the departing company. Sam, let's talk about this for a second. Because this is no BS. I think Pavilion Gold is awesome. Legitimately the best conversations I've ever had as a part of a community member of Pavilion have happened at Pavilion Gold events. The dinner in New York was amazing. When are you going to let CEOs in, and why can't we be in? Seriously. I'm honestly frustrated about this. AJ, you are well served, sir. You are well served.
33:43Sam Jacobs: I know. You got Pablo. I know. You got Insight. I know. You got Hubbot Ventures. You're being whined. You're being dying. I'm asking for the world, though. I'm asking for the world. You were an early investor in SpaceX. You're doing just fine. You don't need us. You know who needs us? Operators. Operators need us. So the answer is, we tried a CEO group, and sadly, besides AJ and Asad, who I love, besides those two people, I can't say that it was the top brass of CEOs that we were getting. We were getting a lot of RevOps consulting firms trying to sell into the go-to-market community. And that's because, you know, we're not pavilions for operators.
34:22Sam Jacobs: Yeah, we're a go-to-market community. So I really liked that in the event that I attended, I even felt for myself that we were able to be far more open because you trust it was a smaller room of people that had come in, trusting that we're not going to let this information out. We're going to use it for ourselves, but we're not just going to quote this person on social media. And so it actually allows real conversations. And that's very rare. It's very hard to have real conversations. It's our highest performing program. It's really, really powerful. If you're interested, please reach out to me.
34:57Sam Jacobs: You can email me, sam at joinpavilion.com. You have to report to the CEO and you have to be either super fast growing AI or at 100 million plus. But otherwise, we'd love to talk to you. Thanks, everybody. Okay, so let's go back to like the venture side for a second. So in the last few, like let's say in the last year, 2020 states, you are sitting in a seat where every day you open your inbox and you see a crazy amount of companies growing at crazy, crazy rates. You're having to make decisions on 50,$100 million bets in 24 hours, 48 hours. If you're really lucky, seven days, but then you're thinking maybe this is a shitty company, something's wrong.
35:38Seven days, like what's wrong here? So like, how does that feel? Like after going through that for a year, how does it feel? That must be exhausting. It's 100 % exhausting. I've never worked harder in my career. I've never been also more optimistic in my career. Just from a Sapphire perspective, I'll tell you, we invest in 12 companies a year. We're pretty tight on our pacing. We've all, as an industry, hopefully, maybe not, but learned the lessons from the 2021 period. But certainly at Sapphire, we try to be slow and steady with it. We have top prospect looks. So even when we go meet that company and we get the data, and it might be three days until we have to indicate one way or the other, I've hopefully done three months of work before, right?
36:23Before even maybe sometimes even meeting the CEO or certainly before even getting the data. So we are well, well honed on those spaces, meeting all the competitors before. And if we're not, there are some set of investors that will still take a shot. That's usually not our game. If we have no idea about a company comes out of left field and it's growing super fast, we've never done work on it, never met the founder and we have 24, 48 hours. It's just not our game to play. And I know some others are playing it and that's great. It may work out fine for them. It's just not our game. But it is exhausting and we are inundated and it has, I think that is also led to some of the slowness around the rounds we're seeing.
36:59There's almost this callus that has been built up around growth rates. Like I don't even look at growth rate. Growth rates are a, they're kind of a gating factor, but they're a tertiary factor as it relates to like the excitement of a company because everything is growing fast. well that's interesting now you have like i went from 100 to 600 and you're like
37:19Sam Jacobs: what gets you excited like a vibe or just something electric or you know like it's it's it's difficult i mean some of this is is a uniqueness in the positioning of the company that's slightly counter-positioned to the competitors or doing something that's slightly different a lot of it is the founder looking back just in the last three months how many product announcements were made what is the velocity of the founder um but it's not it's certainly not growth rate alone because that's not going to be you know as differentiated yeah 100 i mean we we saw a data company it was at 900 of run rate up from zero in three months six months i saw a company in the ai video space 900 million yeah yeah uh they they had they were doing They were doing 70 or 80 million of revenue in a month.
38:15Remember, this is big revenue, big contracts that come from the big labs. They had three or four customers that just needed data in a very specific area. That's crazy. And when you saw that, was that like, meh? Yes. Yes. Because the whole data space, because I had 10 companies in the prior two weeks, we also have an investment in that market. So we're like, you know what? we have the exposure in our portfolio to an incredible growth market in data and RL and, and, and tasks. And so, you know, you guys are like, when, when all the VCs are having dinner together, do you guys like after a few drinks be like, Oh, this is crazy.
38:53Like seven, like five years ago, if somebody told you, you would see that company and be like, eh, you would be like, there's no chance. Like if we saw that company come through our doors, if anyone came through our doors and said, I went from zero to 900 in a year, I would give them money blindly. Now it's like, man, you know, isn't it what a world, like how much every day we marvel at these companies and it's challenging. Yeah. I mean, I see companies selling, like we talked about earlier to the top end of the market, you know, growing nine to 38 this year. I'm thinking of one in particular, and it's a very good company.
39:27It's an incredible product, set of agent products for the back office and cpq and finance and this and that and it's and it's just it's just hard for us to get excited relative to what else is out there um and so it is it is uh certainly wild but there have to
39:42Sam Jacobs: be there have to be some i mean i i hear because you're not the first person that said this there there there has to be capital available for that company whether or not it's you know your specific flavor of it there that has to be a fundable company if it's going from nine i'll tell you growth equity businesses that used to target 20 30 growth are now targeting 100 growth vcs are targeting a thousand percent growth um and so yeah i think there are but there's not many firms that are available for those companies today and i'm seeing some of those rounds not happen or stay out there for two three months if you're going nine to thirty eight you're probably i don't know what you're doing hiring wise but you're probably pretty efficient and you i mean if you wanted to you could raise a round debt it seems like like why even take the dilution at that point what's the capital gonna do or raise a small round from insiders it's so interesting yeah you know because it's i hear that and i'm like well then let's just not play that game at all you know like my my reaction to that is then it's sort of what aj was saying it's It's like, well, then find a way to become profitable and do not rely on any kind of institutional capital.
41:00Sam Jacobs: And who cares? And see if you can print beginning with a million of EBITDA a year and then get it up to five or six or seven. And, you know, it just feels like why even get on the treadmill if that business isn't fundable and it's not exciting. You started on the treadmill, right? Yeah, that's the problem. them i mean if you do cut the burden of business like that maybe it'll double uh next year which is 36 to 72 in 2015 i would have thrown money at that blindly but uh but uh it it it then even the the buyers for that business even become become more now that's the issue is that it's capital allocation it's opportunity cost of capital from bcs and it's also this worry that we all backed companies that were doing pretty well in 2018 19 20 21 and then they didn't exit there's no exit path, right?
41:46Like you have to be in the best companies and everyone's dreaming big, looking at trillion dollar markets with Anthropic, then the Databricks and Andrews, and then the next tier, and then the next tier. Then after that tier, how are you going to get your money back from these companies? Salesforce should have fired them all.
42:01Sam Jacobs: Would you be open? Like if you had a company like that in there. Who wouldn't you be open to? I didn't just say, you know, it's like, I know that. Just trying to get the attention. Yeah. Well, it's more like at what cost would you be willing to get out? You know, like your founder comes to you and says you invested you're underwater can i just have the company back you can go focus on your other things like you really need to do we need to go through the process of me you know shucking and jiving and dancing for you for the next five years like we all know there's going to be no return here for you but there is a business here if you're willing to give me the keys to the car back or is that a crazy thing to say because i know that there's investors that would take massive markdowns on their preference.
42:45Sam Jacobs: And, you know, some people put in 30 and would take six. And at that point, it's like, why not just take zero? It's a great question. I think it's too early for those businesses. And I don't want to come across this because I do think those are some solid businesses and the market's a little rotated one way today and it'll come back. And there will be a new product of financing available for those businesses. And I've thought a lot about that too. Like, what would that look like? but it's too early for those businesses. Where that's happening though, are the 2015 and 17 and 19 businesses to say, okay, do I just give my capital back?
43:19Is there some hybrid secondary primary that I help the investors get some money back? Do I give it all back and just do something else as a founder? I mean, how many of those founders have moved on from those businesses and started some sort of new product and the CFO is now doing the CEO? And I get that, right? I mean, your time is precious and so I understand that too. So it's happening more with that cohort. I mean, if you're still around from 2017, 2018, you've built a business that's probably sustainable because you haven't raised since 21, 22 would be my guess. So you're probably have this whole bunch of 30 to call it$100 million businesses that are growing 20 to 40 % that are just kind of waiting for the rotation to come back.
43:58Like, I mean, I'm sitting here listening to you and being like, whoa, we definitely have the like far end of the spectrum of like, where is where is all that money coming from? Well, it's coming from the frontier models. It sounds like of just like they have so much capital that they have to spend. But is it coming from just enterprise? Is it coming from those tier models? Like if you're a mid market SaaS company, it feels like you're you're kind of screwed overall. all and it's never coming back five to ten years unless you do what you said which is innovate and completely burn the boats for your business you have to have you have to have an ai product that is magical and driving some value at the application layer and at the infrastructure layer the name of the game is fueling the ai that the trillions of dollars and ai capex and compute sort of build out right next gen chip company or data or power uh whatever the ingredients are is is getting in getting in there uh there's just no budget for anything that doesn't have that level of magical feeling impact and roi even though the roi map might be a little fuzzy sometimes it's actually pretty hard and clear and you need to be able to show that and show that pretty quickly to customer suit there's no patience around hey like take three months and now show me a product that works the time to value is also shrinking even amongst the highest of enterprises going back to the moment we're in, as an investor, you've got, you know, we were just chatting about all these companies that are coming at you, these fast, compressed timelines.
45:29What are you noticing that people are making their decisions off of? Because it feels like if growth itself is almost not a signal the same way that one would think it is, is it that you're trying to look at founder ability to keep evolving? Because there's this whole question of durability and maybe the core of it is that we're too early in the cycle for any of this revenue to be considered durable long-term revenue. We're getting in the doors with customers, but the reality is these businesses are going to evolve a great deal. And they might be well positioned because they have the law firm, they have the bank, they have the customer, but the way that they're going to serve that customer is going to evolve a lot as the underlying technology evolves a lot.
46:17And so what we're looking for are people that can just twist and turn at like what speed now? Is that the game? Yes, yes. And I want to, I'm going to answer that directly, but I do also want to say, uh, I, I founders shouldn't feel discouraged necessarily from how many companies are going fast and the extended times. Remember diligence. I really feel like more diligence benefits disproportionately the very thoughtful and airtight and put together founders that have built an incredible business. So you want a founder to be able to do that and not indiscriminately give money to all of your competitors.
46:48So I think it'll actually help the best companies, this kind of market where hopefully things are taking a little bit more time. People are raising the bar and doing more diligence. To your question, I believe that it's interesting as growth stage investors, we always looked at the CEO and the founder, of course. And that was, I don't know, a 30 % weight or maybe a 50 % weight. Now it's an 80, 90 % weight, even at sometimes a billion of run rate. Yes, you look at the unit economics and the margins, but as we just talked about, that's going to evolve so much. Even the products are going to evolve so much.
47:21So we look at the founder. What has the founder done in the last three months? What has the founder done in the last year? I've backed a couple of founders who have had to rebuild their whole harness. And sometimes we architect their whole product after the Opus 4-5 moment in December, because the models became so good and they just quickly did that and to continue to capture market share. I love that. I love that level of agility that they showed, right, in order to do that. And that's almost like I said, a good thing, that level of pivot and first principles thinking and ability to make hard decisions to continue to grow.
47:53Is there like an age thing here where that sort of debt starity, a younger founder has more of it, you know, like 20s, early 30s, that sort of thing. You know, this whole idea of like, is the founder the one who has the advantage or is the kid the one who has an advantage? Listen, I think founders can be great at all ages. I mean, I think if you probably look at the statistics, I have not, but just thinking about the companies, the star companies of today, they do tend to be younger because they probably have less responsibilities. They grew up more with this new and novel technology than someone like me.
48:34And so they can innovate a little bit faster. But yes, that agility is today the name of the game. I mean, just going back to Applied AI, the very thought of an app, it's not really an application software company. I mean, look at what Harvey's doing. Harvey's a part McKinsey, part Deployco and part SaaS agent platform, and even a part AI infrastructure, AI lab as a service business working with these This is interesting because we think of this as application layer, but like you are thinking of this as like way more than application is a piece of what they're doing. This is interesting. Yes, it's it's you have to do all of that in order to differentiate, especially if it becomes very easy to build a UI with cloud code and serve some tokens.
49:21You got to be close to the customers and serve them where they are and really work with them in a differentiated way. And therefore, you need all of those components. is that where the durability comes that if if Enthopic and OpenAI are releasing legal tools the reason Harvey will do fine in the long term is all of these things are happening whereas those guys are just competing at the application layer equivalent so I take a different I feel like a lot of the industry worries that as the models become so great they're going to eat the harness right and then you're going to have one quick and voila all your work is done for you as a lawyer I I look at it differently in that I believe as agents and intelligence get undoubtedly more powerful, you need these specialized vendors even more.
50:06Think about the legal industry. How are they going to figure out their pricing model? How are they going to figure out how to differentiate from one another or what the kinds of products that they, new products that they can deliver to their customers with AI at their back or what should their organizational design look like? These are almost McKinsey-like questions. How are they going to figure out how to train their own models and run evals to figure out what agents are doing and where they're following and what models are good at what? Anthropic, I don't think it's going to help them with that, right?
50:34And so you need a specialized editor to take all of that amazing intelligence, keep up with it, and help plug it together for them, hold their hand into the future. Sam, our friends who've built growth stage SaaS companies in the previous era. Yeah. That game was just so different to this game that like it feels like those are just two separate. Like, you know, for us to think about them adjusting to this, like this is a whole different sport. Like that was football and this is cricket. Like it just feels right different. So different that it makes it feel unlikely that many of them are going to figure this out.
51:08You know, what do you think, Sam?
51:11Sam Jacobs: I think there's technology, there's capability and there's culture. And I think, I mean, Rajiv would know better than us because he saw Owen do it with Finn at Intercom. And you have to have this burn the boats mentality. But I just, I think there's so many people in the workforce right now, they are still getting them to think that a problem can be solved without adding headcount versus employing agents or doing it from an AI first perspective is really, really, really difficult. And then you have all of these product people and all of these engineering talent that have been trained pre-AI that are told to think in two-week sprints.
51:50Sam Jacobs: And they're told that every response to a user asking for a feature is, we'll put it in the sandbox and we hope to get to it in three sprints. The entire operating cadence of some of these businesses, I think, needs reworking. The culture, the belief system, how long should things take? How long does it take to build a new feature? What's okay for, when should I get back to somebody? How much should I work? You know, when should I respond to an incoming message? All of these things, I believe culture is such a real thing because you're not gonna change somebody's mind, especially as a CEO. I mean, maybe you will, maybe you will.
52:25Sam Jacobs: You know, maybe you say, listen, everybody, this is the new world and we're moving in this direction and you're either with me or you're against me. But there are entrenched, it's not even that people, they're not lazy, they're just, there's an entrenched set of beliefs that became codified, particularly, in my opinion, coming out of COVID. And you would know this better than me, Asa, because, you know, you're in the search business. But what work is to a certain group of people is not what it used to be. You know, it's not the same level of hours input. It's not the same level of productivity.
52:57Sam Jacobs: It's not the same level of responsiveness that it was when we were all in the office. And that's why in San Francisco and in New York, where people are in the office, they're moving at a totally different pace. So is it possible to sort of re-architect a company like Outreach? Maybe, you know, maybe. I think that's spot on and great examples. Just reminded of, I have a buddy of mine, he's around my age, and he just left a sass era darling um 16 18 billion dollar valuation company 850 of arr growing 50 60 this is a great company right this is not a company that slowed down to 8 but it is from the sass era it's a name of company you guys all know and he just joined an ai native business in agent search space as their you know as their cfo and he said rajiv i thought we were innovating with ai there and everyone's using cluck this is a whole different ballgame everyone here the vendors we work with are all ai companies the way we communicate uh is very different the whole ecosystem the head count ratios are all completely different and i'm having a ton of friendship at these companies like because i think i'm fairly good with ai as well and then like sometimes you look at a particular person let's i imagine that when you sit down with the best most cracked developers on earth you know even if you think you are advanced you sit with them that's crazy i think it'd be so cool like as as investors if you took like your old school founders and gave them like an internship like for a day spend the day at this come this is the way it's done like i really it'd be really cool this is what the next class of yc should be doing they should just be going from like going to real it going to all these ai native companies and just like spending a day spend a day listen look no further than this this the delta i thought was fascinating the anthropic filing you know anthropic spends more on agents than they do on the rest of their expenses yeah yeah i think they're on sales loft or outreach which is hilarious yeah i know The average Fortune 500 enterprise spends 0.1 % of their total expenses on, I think it's Empropic or AI.
55:16I mean, right? And so when you wonder where's the ROI, people are wondering, well, why isn't all this revenue growth? It's VCs funding it. Where's the ROI? Where's the S &P 500 earnings lift? That's why. It's going to take time to diffuse. And that's also why you need these specializations. I heard the Stripe founder with Sam Altman, he's like, I spent 10 % of my budget on on AI internally. And Sam Maltin was like, that's not enough. He's like, I know. And you're like, if the Krolesons haven't figured it out, what the hell am I going to figure out? You know, they're one of the greatest of all time.
55:48I think the other thing that's kind of interesting is people always like to talk about how agents are going to take a percentage of the labor, labor, really the services, TAM,$10 trillion TAM that we estimated, I think Sequoia just published that too from their AI. I actually think it could be more. Like if you're a capital allocator and you're doing something 20 times better to do a 20 hour fund formation doc, you can do in one hour now with heart. Like, wouldn't you just allocate more dollars towards agents if the ROI is there?
56:17Sam Jacobs: But that's, that's, you know, that, that, that is exactly why, you know, when we, when I was in business school, you learn that if it, because again, like you go in, we were, I was doing financial consulting and you go in and you say, this is your cost of capital. Any project that clears your cost of capital, you should fund, assuming that you have the balance sheet to fund it. But your point is like, well, this 9 to 38 company, I'm not going to fund those. Isn't there a play to just fund all of the good companies that are clearing their cost of capital? But they're limited by their balance sheet too, right?
56:49We're limited. We have opportunity cost of capital. So do we do 9 to 100? I'm saying no to the 0 to 900 million. What am I going to do with this guy?
57:00Sam Jacobs: Yeah. Yeah. Shouldn't that be an opportunity to deploy that? Maybe you can raise a much bigger fund saying all of these good companies are going unfunded. We're going to have agents run the due diligence and we're just going to fund instead of doing 12 checks a year, we're going to write 4 ,000 checks a year. Yeah. Yeah. I mean, it's certainly not our strategy. Are you with me? Are you, are we doing this together, Gene? It's certainly not our strategy today, but it's, So it is. How are you going to LP this? Like the problem is like, who's going to give the funds to play this game? Because it's like, it's a low return, high risk strategy.
57:34You know what I mean? Like that company is never going to provide the biggest return on earth. And like the risk that it doesn't work out, it's pretty high. Whereas over here, there's high risk, but at least like the upside potential seems crazy, which is like probably a place we should spend some time. The Anthropic S1s come out. It's been covered a lot. But one of the things I've been thinking about a lot is this bar for going public. You've got all these companies that are raising all of this money. At some point, a bunch of these have to start going public, right? Like you've got all these inference companies at$50,$60 billion.
58:10Like how many more private rounds are left for them? Not that many. And so when Anthropic goes public, trillion and a half, maybe$2 trillion, raises about$100 billion. We just had space ads. We're going to have OpenAI do it in the next couple of months as well. Does this open the floodgates for more IPOs or have the three of them basically sucked up all the public liquidity and actually the bar for growing public becomes much higher, much harder? Like what actually happens for the rest of these companies? I think it's a net positive. I think it could impact liquidity for some period of time, three, six, nine months.
58:45But no, I don't think folks will shy away from the likes, meaning retail investors and mutual funds from Databricks, from Stripe, from Revolut, from Andruil and others, just because Anthropik's profile was that much more incredible. At some point, there becomes a scarcity feeling. I do think there's going to be just like how there was, what, 30, 40, 50 SaaS companies from Salesforce to CrowdStrike to Datadog to Zoom and Figma. you know, you're going to see probably double that number and hopefully all it, as we just talked about 10 times the market caps or five to 10 times the market caps given these market sizes.
59:16And they're all going to go public in the next five to seven years. And there should be a demand for this new AI industrial economy, agent economy, if you will, of leaders across every single sector and functional area and up and down the stack. And so give it five years. I think we'll see that. I do think the bar will come down. I don't know if it'll be internet era,$50 million in revenue or even no revenue and just eyeballs. But I don't think it also has to be$100 billion in run rate growing 10x year on year, which is just a part that can never almost be matched. Rajiv, let's kind of bring it back down because we're talking about the companies that we all know and are dear to us, but go-to-market tech.
59:56And obviously, Clay, you've been involved with Clay and there's a handful of other companies, But go-to-market tech seems like it's a challenging industry to be in right now. I'm assuming all the companies that you're talking about on the AI that are growing massively, they're not in GTM tech. What's your personal outlook on GTM tech and how do you see GTM evolving, whether it's with AI or without AI, with pre-SaaS tooling, becoming AI native companies, services? What do you see in the future for go-to-market tech? I like to ground people when people talk about the rough exit environment in go-to-market tech.
1:00:38Certainly, there's been some rough exits because there's just, by the way, a lot of companies in this space, too. But one of the biggest companies in all of SaaS is go-to-market technology in Salesforce. Right? And so that's by definition. Yeah, but we always say that's the only one. That's the only one. You know, there's HubSpot. There's HubSpot there. HubSpot's less than HubSpot. No, no. We talked a lot about HubSpot. hot button topic over here okay um but but in terms of the ai native no i think sales is a great use case i mean how many hours do sdr spend searching and building lists and figuring out who to prospect and then now trying to figure out who to email i think the next step is the magical next best action right figuring out what's going to work on what channel with what messaging clay's working on that i and already has some good stuff cooking and clay's growing incredibly fast and so I actually disagree.
1:01:30There are go-to-market AI companies also growing at breathtaking rates at the applied AI layer. You have Sam Blonde from Monaco coming. They're doing really well. Yeah, I love Sam. Is there ever going to be anything cool that's beyond just more emails though? Everything now and when it comes to go-to-market tech seems to be ways to send a lot of emails that are slightly better than the last way to send a lot of emails. When you guys are studying AI and go to market, that intersection, you know, when you think of like different ways that this might move the needle, other use cases come to mind or is it just going to be like a new version of a CRM and new like spam cannon?
1:02:17Yeah, I mean, I think, you know, what Clay's viewpoint would be, what I agree is that every year or two, there could be sort of a new and novel way to grow your business. And that could be experimenting with different channels, like we talked about, or getting more specific in terms of the content and the messaging. I do think there will be an AI native CRM. I don't know how critical a CRM will be when you have agents doing all the work, but someone needs some system to store data and just see how things track over time. And I love what Monaco is doing around that. I think dialing obviously is interesting and it's just doing a great job on parallel and power dialing and now they have a full ai platform and suite around that and so this pursuit remember sales and marketing is the largest budget line item for most companies not just technology companies everyone's got to constantly figure out how to allocate those dollars more efficiently whether it's marketing doing ads or sales people reaching out to customers or going to events and what's the r line it's just new and novel ways constantly to optimize just a massive set of spend.
1:03:21And, and that's why I think it's, it's a little bit written off. I know it's crowded, but I think there's a, there's just a huge AI opportunity for it.
1:03:28Sam Jacobs: Awesome. Rajiv, thank you so much for being our guest on Topline. It was incredible to have you. Yeah. We appreciate it. We're, we're, we're, we're excited to have you. Would you, would you consider being our guest on the show again at some point in the future? happy to happy to folks want to connect with you Rajiv where can they find your best way to connect or talk to Sapphire what's the best way to consume more Rajiv content just Rajiv at sapphireventures.com you can shoot me a note and always happy to chat awesome thanks so much it was great to have you on the show thanks everyone take care
1:04:14Sam Jacobs: If you are looking for more Topline, check out the Topline newsletter at toplinemedia.substack.com. That's toplinemedia.substack.com. Or if you're a video person, check us out on YouTube. Topline-media is what you want there. Have a delightful day, everybody.
1:04:44Thank you.
Before today's conversation, Sam, AJ and Asad share a few words in memory of Adam Robinson.
Rajeev Dham, Managing Director at Sapphire Ventures (a $10 billion venture firm), joins Sam Jacobs, AJ Bruno, and Asad Zaman to make sense of the recent tech selloff and what it means for AI investing. Topics include why Rajeev sees a "duration mismatch" as a core challenge, how the funding bar has changed after months of $50 to $100 million decisions made in days, and why AI application companies are growing from $15 to $100 million in revenue even as steady-state gross margins may settle closer to 30%. Plus, advice for pre-AI SaaS companies, why private equity is still frozen, a data company that went from zero to a $900 million run rate, whether the models will eat the harness, what the Anthropic IPO means for everyone else, and whether go-to-market AI can ever be more than a spam cannon.
Key Takeaways:
- The selloff is about timing, not the technology. The AI buildout is expensive, and Wall Street now wants to see it in S&P 500 earnings, not just in Anthropic's run rate. "I'm a believer. I think there's just a duration mismatch," said Rajeev, who compares it to Amazon's AWS buildout rather than the dot-com crash: "I think it could be a 6-month, 9-month period… when this mismatch needs to be reconciled."
- AI margins may never look like SaaS, and that can be fine. "I don't know if we're going to have the 78% margin businesses. It could very well be you have a 30% gross margin business," said Rajeev. What matters is gross profit dollars: "if you could charge 30 to 40% of $10,000 per person per year versus $1,000 versus 80% of $1,000, your gross profit dollars are a lot bigger." His bet: "I think ASPs will grow by 10x."
- When everything grows fast, growth stops being the signal. "I don't even look at growth rates," said Rajeev. The founder used to be maybe a 30 to 50% weight in a growth-stage decision; "Now it's an 80, 90% weight, even at sometimes a billion of run rate." He looks for founders who rebuilt their product "after the Opus 4.5 moment in December" to keep winning share.
- For pre-AI SaaS companies, the advice is to burn the boats. Rajeev told one founder running a cash flow breakeven $300 million business that "whether you grow 24% or 18%, it doesn't matter," and to "hire a COO, a private equity-like COO just to run that business" while the founder builds the AI products and eventually merges the two.
Connect with the Hosts & Guests:
Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/
Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/
Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/
Guest: Rajeev Dham, Managing Director at Sapphire Ventures - https://www.linkedin.com/in/rajeev-dham-79332812/
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Chapters:
00:00 Introducing Rajeev Dham
01:04 In memory of Adam Robinson
05:51 The Great Tech Selloff
10:35 How the Funding Bar Has Changed
12:46 Why AI Apps Grow So Fast
15:47 The 30% Gross Margin Future
21:28 When Does the AI Land Grab End?
24:38 Advice for Pre-AI SaaS Companies
26:53 Why Private Equity Is Still Frozen
35:11 What Gets a VC Excited Now
39:12 The Unfundable $9M to $38M Company
45:17 Founders Who Pivot at Warp Speed
49:43 Will the Models Eat the Harness?
57:50 Anthropic and the New IPO Bar
59:44 Is Go-to-Market AI a Spam Cannon?
Sources & Attribution:
Clip: https://youtu.be/TNq79c8QNlg
Clip: https://youtu.be/lgMTA5GU7TE
Article: https://www.axios.com/2026/10/26/anthropic-ipo





