Good News For Startups: Enterprise Is Bad At AI
1. Key Themes
The Enterprise Internal AI Implementation Crisis
Enterprises are overwhelmingly failing at building AI solutions internally, with consultancies and incumbent vendors equally struggling. The root cause isn't AI technology itself—it's organizational capability.
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Jared: "Engineering teams at these orgs are filled with people that themselves don't actually really believe in AI, don't use code gen tools, think it's all super over-hyped, are really excited when an MIT study comes out saying that it's all by hype and retweeted... But the consequence of that for the companies is that they can't build the product. So if your engineers don't believe in this, then how are you going to build a product that actually works?"
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Speaker_00: "Apple, a company with infinite resources and infinite access to the smartest people in the world, cannot make a good calendar app. So if that's true for Apple, how could any normal company let alone an internal IT system, let alone like Deloitte or Ernst & Young... most of the time, the output of something like that is bad."
AI-Native Startups Have Unprecedented Enterprise Access
For the first time, early-stage startups are getting deals with major enterprises because established players literally cannot deliver working AI solutions. The 2/3 of projects that were built internally or with consultants failed at much higher rates than the 1/3 that used external AI-native vendors.
- Jared: "The enterprises would certainly prefer to buy these solutions from established software companies, even established startups, like late-stage startups that have been around for a while and have lots of funding and feel less risky, but they fundamentally can't build the products... Then not going to affect for startups, then as if you can actually build something that works, the enterprises will talk to you because they have no other options. Can't build it internally, can't go to an established company. So the startups are actually getting the shot that they never had before."
The Polymath Founder Advantage: Technical Excellence Meets Domain Understanding
Success in AI enterprise sales requires a rare combination: cutting-edge AI engineering capability combined with deep empathy for business processes and the ability to navigate organizational politics.
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Andy: "It's a very rare breed of skill sets where they have a lot of the extreme up-to-date ladies and graded AI understanding and product taste and at the same time to some extent, a lot of the kind of humanity in a sense to understand all the human processes to then grok those into a product."
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Speaker_00: "There actually just aren't that many people who are polymaths enough to be good at product and good at engineering to make things that actually work. There are lots of people out there who are really, really good engineers, but maybe they're just in the coding cave all day and they can't relate to someone working at a bank because they just don't step outside of their coding cave."
2. Contrarian Perspectives
Authenticity Beats Professionalism in Enterprise Sales
Traditional wisdom says young founders should dress up and act corporate when selling to enterprises. The reality is the opposite—being authentically a startup is actually an advantage.
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Speaker_00: "What's funny is this is a good example of when you meet, especially young founders, often they try to like dress up. Like they'll just dress up in a suit and they like copy Microsoft's homepage or something. And they shouldn't do that. Like they should just try to be a little bit more authentic. Like it's actually fine to be a startup. Like it's important to come off as smart and with it, but you do not need to copy the formalism of, you know, sort of wearing a suit or the equivalent of that in like your interactions with people."
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Jared: "I've heard it's actually sort of a particular archetype of big company employee. Someone that really wants to do a startup or has always sort of had dreams of a startup, but they're not actually ever going to do it. The two risk averse. And so they can kind of live vicariously through an exciting startup with founders that they get along with. And if you find someone like that to be your champion, it's like they want you to succeed because they're going to feel like they're on the startup journey as well."
Engineers Who Dismiss AI Are Creating Startup Opportunities
The widespread skepticism among established company engineers about AI isn't just wrong—it's actively creating a massive competitive moat for believers.
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Jared: "Many of the YC partners feel that a lot of the time it's just because the engineering teams at these orgs are filled with people that themselves don't actually really believe in AI, don't use code gen tools, don't think it's all super overhyped, are really excited when an MIT study comes out saying that it's all like hype and retweeted and really one because it's a narrative they want to believe. But the consequence of that for the companies is that they can't build the products."
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Speaker_00: "It turns 10X engineers into 100X engineers and it turns 1X engineers into 10X engineers. I mean, that's like such a gift but it requires an overcoming of this very real emotion that's inside of people."
The MIT Study Actually Validates AI Opportunity (Not the Opposite)
The viral interpretation of the MIT study—that AI projects fail 95% of the time proving AI is overhyped—completely misses that this creates enormous opportunity for the small percentage who can actually execute.
- Jared: "What really went viral was like tweets about this study. And I think the tweets are actually quite misleading... they had concluded just by reading the tweet version of the study that like, oh, all these AI startups that YC is talking about must not be working because the study says that they all fail. But actually, the more I read the study, the more I realized it was actually confirming a lot of the things we've talked about here on this podcast about what AI agents are really like in the real world and what approaches and categories are working."
AI Creates True Lock-in (The Moat Critics Say Doesn't Exist)
Critics claim AI companies are just "ChatGPT wrappers" with no moat. Direct evidence from enterprise buyers shows the exact opposite.
- Speaker_03 (quoting CIO of $5B financial services firm): "We're currently evaluating five different Gen AI solutions. But once we've invested time in training a system, the switching costs will become prohibitive."
3. Companies Identified
Tactile AI
- Description: Business decision engine for banks that handles KYC, AML, and loan approvals in real-time at scale
- Why Excellent: Built in a fraction of the time and budget compared to internal bank efforts that took 3-5 years and tens of millions
- Jared: "Tactile that's building sort of like a high level, like a business decision engine for banks in particular. So it does things like in real time can help them go through like KYC and AML to figure out someone who's applied for a loan... The banks themselves, like city bank and JP Morgan, have tried to build this kind of software themselves, and it's to in each case, it's taken years, three to five years and tens of millions of dollars to actually get this implemented, whereas Tactile was able to build a rest API that makes decisions in real time."
Greenlight
- Description: AI systems for banks
- Why Excellent: Won deal after Ernst & Young spent a year failing to build the system internally
- Speaker_03: "There is a bank that they were trying to sell to, and the deal fell through, because the bank had an existing relationship with Ernst and Young, who apparently builds all the software for the bank... And they're like, well, you know, we trust or vendor Ernst and Young, we've been working with them for years, they say that they're gonna build this AI system... As Ernst and Young spends a year trying to build this AI system, it doesn't work at all, and the bank comes back to Greenlight, is like, actually, could you guys build this for us? And Greenlight now has their system, like fully deployed at the bank, and it's actually working."
Castle AI
- Description: AI mortgage servicer for banks
- Why Excellent: Beating incumbent vendors in bake-offs by being AI-native rather than AI-slapped-on
- Andy: "There's a lot of vendors around that have been around for like decades with very old system and they're catching on as well. They know that their lunch is gonna get eaten... And it turns out what they learn, the banks still do it because they trust the vendor that been around with them for a long time... And funny thing is a lot of times these products are very subpar. The