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The First Wave of AI Is Over - What's Next for Enterprise AI? | Clint Chao

Liftoff with Keith · 2026-07-07 · 40 min

0:00--:--

Key moments - from our scoring

Substance score

56 / 100

Five dimensions, 20 points each

Insight Density12 / 20
Originality11 / 20
Guest Caliber14 / 20
Specificity & Evidence10 / 20
Conversational Craft9 / 20

Clint Chao identifies a critical gap between AI's revolutionary promise and its evolutionary reality in enterprise adoption. While consumers and early adopters celebrate productivity gains from tools like ChatGPT and Claude, large organizations struggle with fundamental readiness issues: legacy infrastructure incompatible with AI workloads, data governance and integrity concerns, and organizational structures stuck in "single-player mode" rather than cross-functional, multi-stream collaboration. This gap creates a distinct investment thesis for Moment Ventures, who focuses on companies solving the "enterprise readiness stack" - infrastructure modernization, data preparation, people enablement, and governance frameworks. Chao emphasizes that winning in enterprise AI isn't about having the best technology; it's about becoming a trusted, embedded supplier that creates switching costs through deep integration with customer data and workflows. He draws parallels to Uber's success in creating alternate-universe infrastructure rather than licensing to incumbents, suggesting that transformative AI companies will need domain expertise, patient capital, and strategic partnerships with platforms like AWS, Databricks, and Nvidia rather than traditional reseller relationships.

Key takeaways

  • →Enterprise AI adoption is stuck between revolutionary value propositions and evolutionary revenue models - most companies are still in POCs and experimentation rather than production deployment.
  • →Winning in enterprise AI requires becoming an embedded, trusted supplier that integrates deeply with customer data and workflows, not just selling best-in-class technology.
  • →The "enterprise readiness stack" includes four dimensions: infrastructure readiness, data readiness, people/organizational readiness, and governance readiness - each creating investment opportunities for startups.
  • →Domain expertise and industry experience remain as critical for AI startups as they were 15 years ago, though some young founders without prior experience are succeeding through conviction and fresh perspective.
  • →Partnership strategy with established platform companies (AWS, Databricks, Nvidia) is more effective than exclusive reseller relationships, which require startups to depend on channel partners' incentives rather than driving direct customer adoption.

Guests

Clint Chao

Topics in this episode

ClaudeOpenAIAnthropicEnterprise AI adoptionData governanceNvidiaDatabricksAWSMoment VenturesAI infrastructure modernization

Questions this episode answers

Has the first wave of AI adoption ended?

Yes, in the consumer and early-adoption sense - everyone now knows about AI and is experimenting with it. But enterprise adoption is still in tire-kicking and POC mode; companies haven't fully embraced AI as a core operating capability due to infrastructure, data, governance, and organizational readiness challenges.

What's the biggest challenge preventing enterprises from deploying AI in production?

Enterprises are stuck in "single-player mode" where individual users get productivity gains, but haven't moved to "multiplayer mode" involving multiple teams, data streams, and cross-functional collaboration. They also face unresolved issues with data integrity, infrastructure modernization, governance, and organizational capability.

How should AI startups approach customer lock-in and switching costs?

Rather than using traditional reseller relationships, startups should embed themselves as trusted suppliers by working deeply with customer data - training custom models, organizing enterprise data, or modernizing legacy infrastructure so the cost of switching becomes prohibitive.

What's different about evaluating AI startups versus traditional software startups?

Domain expertise remains critical (founders should understand target industries deeply), but the barrier to entry is lower because AI tools make it easier for non-technical founders to build compelling solutions. Success depends on revenue, customer traction, go-to-market efficiency, and ability to drive industry-wide AI adoption, not just technology differentiation.

What is the "enterprise readiness stack" that Moment Ventures is investing in?

It's a framework covering four dimensions: infrastructure readiness (modernizing legacy systems), data readiness (organizing and preparing data for AI), people readiness (building organizational capability), and governance readiness (establishing controls, permissions, and compliance for AI agents).

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

12 / 20

The episode contains a mix of useful observations about enterprise AI adoption and startup fundamentals, but is diluted by extended personal anecdotes, softball questions, and repetitive points. While Clint articulates some genuine insights - the 'single player vs multiplayer' AI framing, the 'account control' thesis, the enterprise readiness stack - these are interspersed with filler and conversational meandering that reduces substantive density per minute.

I think AI for most people has kind of been like single player mode where I use AI and make myself more productive in writing or analysis or in what have you. But it's not like we're really interacting together with multiple streams of data from multiple groups within, inside a company
revolutionary value proposition and evolutionary revenue ability

Originality

11 / 20

Clint rehashes familiar VC framings - domain expertise matters, founders need 'conviction', the importance of go-to-market, product-market fit gatekeeping spending - without sharp contrarian takes. His 'enterprise readiness stack' is a useful organizing principle but relatively incremental. The comparison to Uber's infrastructure play is illustrative but well-worn. Limited truly fresh thinking for an operator audience.

experience uh, in a domain really matters
the barrier to entry is lowered I think, uh, you know, because uh, AI is making it easier to create technology

Guest Caliber

14 / 20

Clint is a legitimate operator and investor with early-stage exits (Cube, Skystream) and a now-institutionalized $500M+ fund focused on B2B infrastructure. His perspective is grounded in actual deal-making and portfolio observation rather than punditry. However, he's a GP managing other people's capital rather than a founder/operator who personally scaled a major business, which limits his caliber somewhat for direct execution advice.

co founder and general partner at Moment Ventures, a Palo Alto based early stage B2B tech VC
early executive folks like Cube and skystream before pivoting to vc

Specificity & Evidence

10 / 20

The episode lacks concrete data, metrics, and named examples. Clint mentions Clario (a data cleanup startup) only in passing without detail, references Uber in historical context, and drops generic references (Mag 7, Anthropic, OpenAI, AWS, Databricks, Salesforce) without specific cases or numbers. The 'terabytes of Bollywood movies' is an anecdote, not evidence. Most claims remain abstract - 'enterprises are tire-kicking', 'governance readiness' matters - without supporting numbers or concrete examples from portfolio companies.

one company that they did an uh, audit of, they found like terabytes of Bollywood movies on their corporate network
90 plus percent of startups exit, you know, successfully exit through M M A

Conversational Craft

9 / 20

Keith asks surface-level questions that rarely challenge Clint's framing. Few genuine follow-ups or pushback. The host accepts platitudes like 'some things never change, some things are new' without pressing for specifics. Lengthy personal tangents (Clint's daughters, Cal football) derail substantive flow. Keith does attempt to probe on SaaS lock-in and data center concerns but doesn't dig deep; Clint's answers remain abstract and unchallenged.

My favorite investments, my two kids, I have uh, two daughters, 24 and 20 now
Did you say though that the first wave is over? Did I read that correctly?

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A77%
  • Speaker B23%

Most-used words

data26industry15interesting14today13founder12first12ready12create12sales12market12infrastructure11early10enterprise10help9inside9value9

Episode notes

The AI boom isn't over but the first wave is. In this episode of Liftoff with Keith, Keith sits down with Clint Chao, Co-Founder & General Partner at Moment Ventures, to discuss where AI is really headed, why enterprise software is entering a new phase, and what founders should focus on as the hype settles. They explore venture capital, AI adoption, enterprise transformation, startup execution, and what separates companies that create lasting value from those simply following the latest trend. Whether you're a founder, investor, operator, or simply curious about the future of AI, this conversation is packed with practical insights. Key Topics Why the first wave of AI is ending What comes next for Enterprise AI Building companies during technology shifts Venture capital perspectives on AI startups Enterprise software trends What investors are looking for today Long-term opportunities in AI If you enjoy conversations with world-class founders, investors and operators,

Full transcript

40 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Foreign.

Speaker B: The sponsor of Liftoff with Keith is the one and Only Compass Strategic Advisors.com an experienced partner to help you navigate everything from cap tables to stock option and compensation plans and all types of backroom and marketing services. There is no better friend to the startup CEO than Compass. Check them out at Compass Strategic Advisors. Clint Chow is the latest to join the Liftoff. He's the co founder and general partner at Moment Ventures, a Palo Alto based early stage B2B tech VC for me founded in 2015 moment back startups transforming the operation of large industry verticals Logistics, food, healthcare, creator, economy, travel. Under the thesis of what they call the future of industries. The fund is institutionally backed and is actively deployed at Seed in pre series A. They've got a pretty deep portfolio of a whole bunch of successful deals. Clint's a long time Silicon Valley operator turned investor, an early executive folks like Cube and skystream before pivoting to vc. He's a proud Berkeley Cal alum, a clear direct writer and thinker whose recent posts on enterprise AI adoption and sharp and timely thoughts. Also if you leave him alone behind the three point line and he gets his feet set, forget it. It's night night time. Game over. But this game's just starting as we are going to welcome Clint to the lift off.

Speaker A: Clint.

Speaker B: So tell me, how are your two favorite investments doing?

Speaker A: My favorite investments, my two kids, I have uh, two daughters, 24 and 20 now.

Speaker B: Wow.

Speaker A: Uh, so one, uh, uh, my older one is out of college and is uh, living in Utah and uh, my younger one is just finished her second year in college and is interestingly enough, you know I was a double E coming out of school, my wife's finance and both my kids are, are arts kids. So uh, my younger one's pursuing a career in film and TV production and my older one is pursuing a career in contemporary dance. And uh, that so awesome. Um, what does that, does that tell

Speaker B: you that these kinds of traits that we acquire are not really hereditary or do they just see what you would do it decided to steer away from all of that.

Speaker A: Well so first of all I'm super proud of both of them. I think it's really cool what they're doing. It's. They're probably pursuing two of the things that I won't really, you know, disrupt. Um, so I love that. And secondly is I think just growing up they probably just found stuff that dad was working on not, not that interesting and the real world out there far more interesting. So uh, it's excited about what they're pursuing.

Speaker B: Good. And how's everything going with the fund and your portfolio?

Speaker A: Great. Yeah, it's a, it's an interesting time. I think everybody knows that, uh, in the last couple of years with AI coming into the foray, it's been super interesting with so many things going on and it's really interesting. I, I don't know if you think this, but it's like the general public is kind of the audience for us in real time. Right. I mean, anything that you hear about some company, you know, uh, we're referring to the CEOs of these companies by first name as if we know them. We're like getting, we're getting a chance to witness a lot of the building sort of in real time, which is, I find that super interesting, not just as an investor, but also as a consumer, uh, of AI. You just jump on X and you'll see all sorts of interesting things from people.

Speaker B: Did you say though that the first wave is over? Did I read that correctly?

Speaker A: Well, it's interesting. I think the first wave when we're talking about AI is that, uh, I think everybody knows about AI. Uh, everybody's kicking the tires of AI and everybody's finding all sorts of great productivity gains from it. But I think if you dig deeper, we're still really early in the fact that, uh, you know, I don't know if enterprises have fully jumped in yet and ready to actually embrace AI. There's uh, all sorts of issues that they still got to figure out. Whether it's uh, integrity of systems using their data, there's governance, there's the fact that their infrastructure might not even be ready for a lot of this. And, and the way I like to say it for consumers is like, I think AI for most people has kind of been like single player mode where I use AI and make myself more productive in writing or analysis or in what have you. But it's not like we're really interacting together with multiple streams of data from multiple groups within, inside a company and actually benefiting from the scale of that. And I think that's coming, but I think that's opening the door for startups to innovate in those areas. So we've been spending a lot of time on that, which is really cool.

Speaker B: So we're still sort of stuck between, as you called it, revolution and reality.

Speaker A: Revolutionary I call it. Uh, uh, we always get stuck between revolutionary value proposition and evolutionary revenue ability. That's not really a word, but I made it up. It's that in enterprises you do have to Sell something to them. Right. And I think as a, as a startup company, you have to remember that that's first and foremost to create a product and wrap it into something that, that uh, customers can actually buy and then you can build a sustainable, long term, you know, value from that. Uh, the one thing about AI that's interesting right now is things are changing so fast that uh, you know, you design something today, you're probably competing against a company that's going to be coming out in a year that doesn't even exist yet.

Speaker B: It is really fast. The pace of evolution, the pace of change. We uh, you know, could refer to LLM models and how fast they evolve compared to what happened with the old oss we used to play around with. But I also just look at customer adoption. So let me ask you, what does winning look like in this whole world of AI? And I'm trying to win the game, I'm trying to score, I'm trying to close a deal. Has that changed a lot in terms of the companies you're working with and what you're seeing out there?

Speaker A: Well, I think, you know, there, there are obviously some very fine exceptions to this because, you know, the, the frontier models that have blasted out of the gate and we refer to their people, uh, by first name essentially. You know, they basically suck the air out of the room in these early chapters. Right? Because we're all, we're all engrossed with using their platforms, whether it's Anthropic or OpenAI or X or what have you. And every one of them, they just, they're game changers for all of us. But as far as being successful within enterprises, I think at the end of the day, I think, uh, I'd like to say that the new mode is really account control. It's not really a technical thing anymore. It's that you have to be able to create a solution that actually, you know, uh, captivates the customer in a way that they want to stick with you over the long term. Right. Because right now enterprises all over the planet, you know, I think generally we're still in tire kicking mode. I think a lot of people are doing, uh, experimentation. I think they're doing POCs, they're testing things out. Uh, a lot of companies have people who have been anointed the AI person, you know, make AI work inside the company and so they're trying out as many things as they possibly can. But if you're a startup and you're responsible for, at the end of the day, driving revenue and Creating revenue for your company. Um, you spend a whole bunch of resources to get in with an enterprise and you do a POC and what have you. But if, if they can easily just turn you off, uh, that's really hard to build a sustainable value proposition. Right? On the other hand, if you're a startup that for example does a bunch of work with companies where you're ingesting a lot of their data and you're helping them train and uh, create models of their own that they can use for their own productivity needs, uh, or perhaps you're mining data in a specific domain like healthcare or another industry where really hard to collect data and uh, and use it. Once a company goes through that effort, I think there's a tendency to not want to have to go through that multiple times with multiple vendors. So again it's, I'm sort of an old school sales and marketing guy. I always think that uh, the best technology doesn't necessarily guarantee that you win, but uh, if you have the most customers, at the end of the day you're guaranteed to win.

Speaker B: What's the lock in feature? You have to find that lock in and not let them go. I mean I have to balance that out with what we, you and I have talked before about the SAS apse and you know what's going to happen with the salesforces and servicenows and Adobes of the world. Are they under like existential threat time or do they have enough locked in value that data you referred to that they're safe and that let AI go work on some other things? How do I balance that?

Speaker A: Well, let's just look at us as consumers today. I mean, I think uh, maybe two years ago, two, three years ago, we might all have our favorite frontier model, our favorite LLM to use. We were either an OpenAI user or a CLAUDE user or what have you and maybe you even subscribe to one specifically because that became your go to platform. Uh, but I think today because the capabilities are changing so dramatically, uh, we're sort of playing all the different platforms interchangeably. I think people use, you know, um, AI platforms for very specific uses. You might switch from one to the other. So I think that's going to be the same case for enterprise sales.

Speaker B: Right?

Speaker A: I mean I think you really have to figure out a way to get customers to really embrace what you have. They got to dive in with you. I always like to think as a, as a lasting vendor to an enterprise, you have to find a way to be, get on the inside looking out. So you have to find a way to become part of their company in a way where you become a trusted supplier. For some discipline in AI, a lot of it is in, is in uh, uh, mining their data, organizing their data in a way that can then be trained and used. Uh, in AI it could be um, maybe uh, building uh, out or modernizing their infrastructure so that uh, even you know, the, the dated infrastructure that they have can benefit from the uh, efficiencies brought forth by AI, all sorts of things. But those typically require a good bit of work, not just from the, the customer but from you as a supplier. So working hand in hand with them I think helps create, I don't want to call it lock in. You always have to continue to earn your keep, but at least buys you that relationship where you're on the inside looking out, if that makes sense.

Speaker B: Yeah, you have a unique perspective in the seat you sit in, um, the size of the fund you work on plus your background in this business for so long. How do you look at the contrast between those companies that you decide to invest in and, and those you take meetings from and are evaluating how uh, what, what are you looking at when you're taking these meetings? You've qualified them to some degree. So what's that idea that gets you excited and then when they come in and really share the details of their story, um, their technology, their moat, their go to market, their team, what is it that you're seeing out there that might be different from what we first looked at 10 or 15 years ago?

Speaker A: Well, it's interesting Keith. Some things, some things never change and some things uh, are sort of brand new in this new environment. But some of the things that never change is that you know, experience uh, in a domain really matters. You know, a lot of uh, our, a lot of the kind of companies we look at are building next generation infrastructure for other established industries. So they'll build it, they'll build technology infrastructure for logistics, the logistics space or the food industry or the healthcare industry. And a lot of times uh, value propositions may sound really uh, awesome. Right? It's like it's so easy to go ahead and say we're going to transform healthcare for this, but as you know nothing happens uh, that easily. Uh, uh. And I think entrepreneurs that know what we all don't know about what needs to get done in an industry I think gives them an advantage um, in succeeding in that space. Uh, the one thing we have learned as companies have gone off to create logistics solutions or food solutions or healthcare solutions is that the industry, you know, that you're targeting, sometimes they're like a hundred years old, right? They're, they're used to doing things a certain way. And it takes relationship, uh, building. It takes a narrative that makes sense. It takes getting to the right influencer in, in the right kind of company to help to move the market. And, but once you can, then you can sort of break the log jam and, and uh, and create something of lasting value best exemplified. For example, if you think about someone like Uber, right? Uber's what they got. They got going in 2009. So maybe a little over 15 years ago they, you know, came forth and you know, they could have actually just used their technology to, you know, license to the existing transportation companies, like cab companies for example, and use, uh, their software to track cabs on iPhones. Would have been a totally valuable, um, resource. But if they did that m, they'd probably be a lot smaller than they are today. As you know, they created an alternate universe infrastructure. And what it did was it changed everything about how we as consumers view transportation and also how people who make a living in transportation view their profession. Now they can do so many things that you couldn't have done 15 years ago. And so hundreds of billions of market cap later that they created, there's like no going back, right? So they created something of lasting permanence, but they had to climb that. They had to scale that wall and that was definitely not easy. So I think today when we run into companies, we try to look for that, like if, okay, this is a groundbreaking idea. It might require some behavior change in your target customer. But if you're right, is there a chance you can potentially run the table on the behavior in the future, uh, and capture all of that value as a result? I think it's tricky. I think, uh, it takes a lot of conviction, a lot of experience, good timing. It takes uh, a good team that can actually figure out. Sometimes it takes a little bit longer than they originally planned. Uh, uh, and we get to see it firsthand as investors.

Speaker B: Yeah, um, one of the things I think I'm picking up on too is the, is the value in working with partnerships as you go out and go to market as opposed to, you know, that enterprise sales force that took on the world. Now you're like, okay, I'm going to go ride the coattails of AWS or Nvidia maybe. It depends on the industry, of course.

Speaker A: Right.

Speaker B: Flake and data bricks, folks like that in the enterprise space, do you see that as more an ecosystem Driven go to market plan where you've got to have some of those relationships in place or it's going to be even a steeper climb.

Speaker A: I think it's yes. I mean I think there's definitely um, there are definitely uh, entities out there where you have aligned interests where I, you can succeed together. And in fact you, in most successful companies, you, you know, successful startups, that is, they've actually benefited from a uh, a relationship with some big established player that also benefited from whatever initiative you were pushing. And so I think for founders that are starting off in a particular industry, it's really incumbent on them to figure out those relationships early, the ones that are tricky. And this is probably a deeper subject of conversation but is like I sometimes startups try to establish like a reseller or partner reseller relationship with a company that's already established in the space. And in that, in those examples I actually issue caution quite a bit. I think it's a lot harder than it sounds to actually get, be uh, successful in an industry. And if you sign a deal that gives uh, an exclusive for example to a big established player with a big sales force, that might seem like an easy path. I uh, would, I would make sure that it makes the most sense to do that because at the end of the day uh, I've seen it before because I used to be a sales guy. Uh, as a startup it's up to you. You've got to be the one that actually makes it happen with your customers. Even though you're, you might have a big channel partner that uh, can, can bring you into meetings and what have you. But at the end of the day it's your job to convince the customers.

Speaker B: Yeah, you have to drive the initial demand probably and close the deal. Maybe you get a little bit of help, you know, uh, support or service or installation, I don't know, something in the middle layer.

Speaker A: Well, and you have to, you know it takes a lot of resource to train a sales organization that is already selling something else. Right. And so you know, they have their own thing to worry about. They have a customer that they're selling millions and millions of dollars worth of their own products. So you show up. If you help enable the uh, the acceleration of sales of other products that they have, that's great. Then now you have a complimentary relationship. But at the end of the day you've got to take care of your own needs and make sure that ultimately you can be successful in selling those products. It's up to you as the founder.

Speaker B: Okay, let's turn uh, slightly towards your business and how you're managing a venture firm today. It seems like it's awfully crazy, maybe it always is, right? In terms of, of deal flow and managing portfolio companies and you know, evaluating next rounds and need for additional financing. What's happening out there today, Clint? Give me a little look behind the curtain here in terms of the companies uh, that are looking for ah, funding at your stage and how you're evaluating things today. Um, I mean to me, um, and I don't mean to tease you, it's just gotten to be much more of a early stage, find the right companies and get in and don't worry about valuation or take out later stage funding opportunities and, and beat them before they go public. But there's this big void of companies that aren't getting funded because they don't fit that, that perfect story. And then uh, maybe they don't fit the perfect category. Um, but there's uh, a huge void in the market for some hot stories.

Speaker A: Yeah, I think the one, one thing that's maybe different today than in the past is that uh, you know, you know one can invest in the public market today with companies. I mean if you pay attention to the mag 7 or the other high flying public companies out there, they've captivated a lot of the investing public in general. Right. I mean, and we've seen people who have invested in companies and uh, you know, got a nice multiple on their investment on a public company. So as, as a private investor at the earliest of stages, you know, I think it's important for us to be looking for something that can actually deliver way more than that. Right. I mean, I think uh, the reason why venture is a category is because there is the opportunity to get uh, involved in a company that can have profound returns on not just your fund but for, for all the, all of the company's shareholders, uh, and what have you. And we're seeing that with some of the companies out there today. Um, what's interesting now is that uh, you know, the barrier to entry is lowered I think, uh, you know, because uh, AI is making it easier to create technology. Um, even non technical founders can create pretty compelling solutions. Um, I think it's really important for founders to be, you know, really, really specific about what they're building. I think it's important that they create a really, you know, um, a really good narrative on, you know, why, why is your company actually formed and, and what problem, you know, are you trying to solve? And um, and, and you have to Help actually the adoption of what's going on in your industry in general. With AI. I think we're all, as you know, there's, there's uh, there are proponents of AI and then there are critics of AI and I think uh, if you can actually be the catalyst to cause your target industry to fully embrace the value propositions, uh, and efficiencies that AI can bring, that's a really good sign. Again that comes with founders, uh, that either have the domain experience who've been there before, who understand the industry, or the complete flip side of that is that uh, what we're seeing today is a lot of really young founders coming right out of school, in some cases dropping out of school and sort of sucking the air out of the room with you know, excitement and uh, conviction in a way that um, you know, older entrepreneurs, uh, don't have. So I think um, both can win. There's really no, there's no one way of succeeding. But we have to look at all of that. When you boil it all down, at least for me, since I focus more on enterprises, at the end of the day, revenue speaks volumes and customer traction speaks volumes. And I spend most of my time just trying to understand, go to market, sales efficiency, you know, how do the customers react to this kind of capability, uh, and what have you. But um, it's pretty exciting times right now I'd say good and bad because I think uh, for the audience a lot out there.

Speaker B: Yeah, you've shared with me a little bit of what you're looking at and it's, it's very exciting. It's very broad too. I forget though, are there any specific signals or sectors you're, you're watching that maybe other people haven't caught on to yet?

Speaker A: Uh, I highly doubt that uh, anybody is focused on a space that other people aren't thinking about. I think the good news about AI is it's opening the doors for every single market to benefit from. But I would say one area that we are actually um, spending a good bit of time on is actually based uh, on the stuff we already talked about. But I sort of think of it as uh, enterprise readiness.

Speaker B: Mhm.

Speaker A: And that's just a, you know, fancy words to describe that. Most enterprises today, while they're enthralled with AI, they just aren't ready for it yet. They're not exactly sure how to actually embrace AI such that they're, you know, their company data is preserved and that uh, that they have the right kinds of governance in place and, and uh, and all the rules are in place so that you can actually go first, head first into uh, into embracing it. And so a lot of the companies that we see right now I can sort of put into different, what I'm calling the, the readiness, uh, stack, if you will. So, you know, is your enterprise ready for AI? Well, in what dimension? Uh, you know, is your infrastructure ready for AI? There's all sorts of things you need to do to modernize your infrastructure so that it can be ready. Um, uh, is your, uh, is your data, uh, A.I. ready? Can you actually, you know, organize your data such that actually can be, can be used effectively? Um, are your people ready for AI? Uh, a lot of people are playing around with it, but you know, is, can you really build something meaningful? Uh, and are people ready to do that? Are we ready to go from single player mode to multiplayer mode again, uh, if you will. And then the last one would be governance readiness. Just because you put, you know, uh, you release agents inside your infrastructure, inside your infrastructure are the right people being given permission to access the right types of agents? And uh, and are you able to sort of arbitrate who gets access to what? Because there's a high price to screwing that up, right? I mean if, if the wrong, uh, if the wrong person, uh, gets a hold of something, you know, that's going to set you back. It's a little bit like, you know, in the EV space when you hear about a crash that the first thing you hear about is that it was this maker's EV that crashed. And then they have to, they have to overcome this public, you know, um, uh, naysaying of all that, of all the dangers of this. And it's the same thing with enterprises. I think they're really paranoid. They don't want to. Right. They don't want to expose their data,

Speaker B: uh, on that level. What concerns you the most about the AI tidal wave? I mean what one thought is, of course, security of data sure reaches and, and you know, these things have a threat level that can, can go to 10 rather quickly. Yeah. And then I know you have a kid in Utah, they're talking about, you know, Mr. Wonderful building his data center out there. Um, and lots of uh, debate about whether that should be permitted and to go through. Um, where do you stand on some of these? Do you have a strong view on, on how data centers are being viewed or how uh, security and legislation are coming together or not coming together or uh, some thoughts around those things?

Speaker A: Well, I think, you know, I think if, if we as a as, as, as an enterprise community, stay disciplined. I mean, in a way, you know, having companies pause for a second and wonder, um, is my enterprise really ready for this, uh, this uh, phenomenon? I think that's a good thing, right? Because, you know, unlike past technology trends where people can just, you know, go ahead for, let's create a mobile app and just throw it out there and see what happens and, or let's just put up an Internet store and see what happens. You know, there are ramifications to things going not going uh, the way you want now, right? Because now you're really dealing with super valuable data or uh, infrastructure that could be exposed. So I think it's important to be thoughtful about how you do that. And that's why you have people in organizations like the, the CIO or the C, uh, the CISO or the cto, and it's their job to make sure and police how companies, how their own companies actually use this technology. And so, um, so I think it's really important. I think it's going to play out in a really meaningful way. I'm super excited about how that's going to play out because I think we're seeing companies come out that are helping solve those problems. Right. Um, we, we have, we had a company that just launched last week that is basically working with companies to clean all of the, what they call rot data, the bad data that sits inside your company. It's like, if you're going to use AI to train on your data, why would you have them train on the mounds and mounds and mounds of garbage data that sits inside your corporate networks? Whether it's former employees that no longer work there, whether it's old file formats that aren't even supported anymore, or it's uh, you know, people putting their entire music library on their corporate network. In fact, they were joking that uh, one company that they did an uh, audit of, they found like terabytes of Bollywood movies on their corporate network. Anyway, there's all sorts of garbage data sitting inside networks, so that's like a good investment though. So, so why, why would you, why would you uh, train on all of that data? That's unnecess. So this company, Clario, what they do is they actually help figure out what kind of data you actually have in your network so you can clean that up. It's sort of the Maria Kondo of, uh, data. Right? So how do you clean all that up so that you're only training on the things that are most relevant, uh, and also significantly reduce your token Spend. Because why spend money training on data that's not valuable.

Speaker B: Oh, excellent points. Okay, Clint, we're gonna now pivot to what I call a little quick, uh, fire round and sure hit you with a few fun questions. Um, I won't ask you about, uh, Cal's football, uh, record, though.

Speaker A: Hey, in a year, we might be having a different conversation. But that, that's the whole beauty of Cal, is that, uh, the off season is the time where you're most optimistic.

Speaker B: You. Do you count Mendoza as a Heisman Trophy winner of yours? Since he went to the school and, and got all the best education and training and even got his degree and then left to go.

Speaker A: Well, I know what graduation he went to, so I know.

Speaker B: Okay, let me ask you. What's a, What's a perfect pitch deck? If I'm coming in to pitch you, what's a perfect pitch deck look like?

Speaker A: Um, what I really like to understand when I see a pitch deck is at the highest level first, like, why are you doing this? Why is your company doing what it's doing? What's the implication of that? Because I think a lot of times decks go straight into their company, uh, features and benefits and what have you. And so one of the questions I always ask is, if your company ceased to exist tomorrow, what would customers do in the meantime? Right. I mean, number one is there's probably another solution out there that does that, or maybe not. You know, a lot of times, uh, you know, we have so many companies that are still targeting, you know, problems where people are still using spreadsheets or clipboards and what have you. Very old school stuff. Yeah, I think, I think technology has advanced to a point now where there are alternatives. So it's got to be. There's got to be a higher cause there. And what is it that you're actually enabling if you're right? And that has to speak out from the deck?

Speaker B: Yeah, I like that. Along those lines, the founders coming in to pitch you, what's their ideal background?

Speaker A: Um, it's always super interesting when the founder actually comes from the space that they're trying to solve the problem of. Um, because as I mentioned before, it's like, what is it that we all don't know about what's really going on in that space? And I think those are, uh, those are key characteristics. But one thing I like to do is I always like looking at the background of a founder and I sort of draw it out linearly. And I ask myself, is this founder doing this startup? Is this. Does it make Sense like is this the logical conclusion of this great career that they've built up to this point? And can I draw and can I connect those dots so logically that's like, oh my gosh, of course this person's gonna kill it here in this space because they, it's like they've spent their entire career getting to this point. And um, that's super interesting. Um, if you see a founder that has sort of whipsawed back and forth between different industries, um, there's nothing wrong with that per se, but sometimes I wonder if, if they're sort of, they're still trying to find the right wave to surf on as opposed to someone who already spent surfing on this one beach for years and years and years and knows exactly when the tide's coming. Yeah.

Speaker B: A company that comes to you in early stage.

Speaker A: Yep.

Speaker B: And has, comes to the end of the, of the deck and they don't have an exit strategy mentioned like what their plan is, you know, is that a good thing or a bad thing?

Speaker A: Uh, so first of all the companies were we're meeting are literally at their very earliest days. So I think it's fair to not necessarily know how it's going to play out. Um, fact of the matter is the numbers talk. I mean like 90 plus percent of startups exit, you know, successfully exit through M M A. It's great that there are public market options and what have you and I think everybody would love that as an option. But um, yeah, I think, I think it's okay to not necessarily know. But I also think it's important for entrepreneurs to know what they're building is actually really big and they're not interested in a short term or shorter term, you know, outcome, uh, if you will. Because that's obviously not great for venture investors. There's nothing wrong with having a short term perspective, but it doesn't necessarily mesh well with the venture model. So you might, there are other ways to fundraise for your company.

Speaker B: Eve of mine, I don't think you should have an exit strategy that early stage anyway. Um, okay. Five positions and you know, CTO slash VP of engineering, um, uh, product marketing, um, CMO type, CRO, head of sales type, um, and a finance type.

Speaker A: Okay.

Speaker B: They put them in order when you want to have them hired and on board.

Speaker A: Oh, okay. Uh, well I, I think the, the, the technology folks need to be there from the beginning. I think they're the ones who are actually going to architect.

Speaker B: So the CEO of the product smarts for which one?

Speaker A: Well, I think I think the founder typically has some pro, at least the initial product idea. So they have to have that, but then they also have to have the ability to get the product built. Um, interestingly enough, a lot of companies that we run into that are trying to solve a problem in another industry, they're actually started by non technical founders because they're the ones who like grew up in the bowels of some industry and said, you know, there's got to be a better reason, there's got to be a reason why, you know, there's uh, got to be another way to do this. Right.

Speaker B: And so vibe, code something or they can. Yeah, yeah.

Speaker A: Or a lot of times what will happen is they'll say, look, I'm gonna, I'm gonna create a startup to disrupt this industry. And in many cases they'll like team up with like their college roommate who works at Google or something. And, and so they, they team up with somebody technical and get the product built. But I think those that tandem, um, needs, that ingredient needs to be there. Having said that, they also have to be good at selling because you don't want to necessarily spend on expensive sales resources until you really have good product market fit and are ready to scale the business. But when you do have that, that's uh, a good time to start contemplating bringing on an additional resource. I don't know if there is a one size fits all for companies, but somebody said a few years ago, uh, something I like is that uh, as a founder what you want to do is figure out what you're spending the most time on, uh, and then fire yourself and bring somebody in so you can focus on some of the other things. I think a founder has to sort of be disciplined in all corporate disciplines, if you will.

Speaker B: That's an interesting point because a lot of times at that stage of company development, they're really encouraged to be founder led, sales driven.

Speaker A: Right, sure.

Speaker B: But my experience would say that that's fine to help open the doors and create the relationships and spell out the product, but you probably still want to have an experienced salesperson drive the overall process from opening the opportunity to closing it.

Speaker A: Yes. With the exception that I don't necessarily think you need to bring in an executive person responsible for sales or revenue right out of the gates. I think it's perfectly fine to incrementally bring in some resources to help offset your efforts as a founder because at uh, the end of the day, for a uh, good bit of time, you as the founder are going to be the one that closes opportunities but if you need additional support to help fill the top of the funnel up with opportunities to go and close, I think that's super helpful. But it doesn't have to be high level.

Speaker B: So we're going, we're going a little bit longer than usual, so I'll have to just extend my tab next time we, uh, go out.

Speaker A: Okay. Drinks on me.

Speaker B: Yeah. But what about the most common mistake then you see from companies at this stage that you meet with? Is it hiring too early, too late spending on marketing too early, too late buying ads or hiring the overpaying for engineering talent? I don't know. Tell me.

Speaker A: So, actually, the common thing that you just said on all those is spending money before you really know what you're going to get out of it. And I think that that's really important. Right. If you're spending money on ads and you don't really have product market fit yet, then you're just bringing in the wrong kinds of customers. If you're hiring a salesperson when you don't really need one, you're spending money going, you know, unnecessarily. Uh, uh, and Mark, you know, so all those disciplines, I think just, you just have to be really disciplined with how you spend.

Speaker B: Right. On Clint, my partner moment. Little sleepy Palo Alto firm

Speaker A: and, and

Speaker B: retired basketball players, hoop star. Um, this has been really fun. Thanks for, thanks for chatting. Any final thoughts you want to share?

Speaker A: No, I think, uh, it's a great chat and, and uh, I'm excited for the time. I'm excited for founders going out there doing their thing and, uh, excited to meet with them.

Speaker B: That's awesome. Thanks so much.

Speaker A: All right, Keith, thank you.

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