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Lenny's Podcast / episode intelligence

Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon

11 Jan 2026 23 published claims 3 attributable people

Speakers in the public record

Claim mix

belief 7evaluation 6recommendation 3prediction 2observation 2preference 2commitment 1

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The useful parts, with receipts.

23 published records

02 / evaluation

I mean, if you think of it's also the most beautiful part of AI, which is, I mean, we are all much more comfortable talking than following a bunch of buttons and all of that. So the bar to using AI products is much lower because you can be as natural as you would be with humans, but that's also the problem, which is there are tons of ways we communicate and you want to make sure that that intent is rightly communicated and the right actions are taken because most of your systems are deterministic and you want to achieve a deterministic outcome, but with non-deterministic technology and that's where it gets a little messy.

“I mean, if you think of it's also the most beautiful part of AI, which is, I mean, we are all much more comfortable talking than following a bunch of buttons and all of that. So the bar to using AI products is much lower because you can be as natural as you would be with humans, but that's also the problem, which is there are tons of ways we communicate and you want to make sure that that intent is rightly communicated and the right actions are taken because most of your systems are deterministic and you want to achieve a deterministic outcome, but with non-deterministic technology and that's where it gets a little messy.”
Publisher
Lenny's Podcast

03 / evaluation

And there's so many other benefits to limiting autonomy because there's just danger also of the thing doing too much for you and just messing up your, I don't know, your database, sending out all these emails you never expected.

“And there's so many other benefits to limiting autonomy because there's just danger also of the thing doing too much for you and just messing up your, I don't know, your database, sending out all these emails you never expected.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

04 / evaluation

For instance, MRIs and block tests, because as soon as you know patient's information, it's easier to approve that and AI could do that versus something like an invasive surgery, et cetera, is more high risk.

“For instance, MRIs and block tests, because as soon as you know patient's information, it's easier to approve that and AI could do that versus something like an invasive surgery, et cetera, is more high risk.”
Publisher
Lenny's Podcast

05 / belief

I just saw Demis from DeepMind, AI, Google, whatever they call the whole org, talking about this where he thinks that's going to be a big part of where they're going, combining the image model work, the LLM, and also their world model stuff, Genie, I think is what it's called.

“I just saw Demis from DeepMind, AI, Google, whatever they call the whole org, talking about this where he thinks that's going to be a big part of where they're going, combining the image model work, the LLM, and also their world model stuff, Genie, I think is what it's called.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

07 / belief

I'm not saying they're not important, but I think just this, I'm going to keep jumping across tools and going to pick up and learn if new tool is overrated.

“I'm not saying they're not important, but I think just this, I'm going to keep jumping across tools and going to pick up and learn if new tool is overrated.”
Publisher
Lenny's Podcast

09 / commitment

In terms of what is going on in the community, I feel there's just this false dichotomy of this either evals is going to solve everything or online monitoring or production monitoring is going to solve everything. And I find no reason to trust one of the extremes in the sense that I will entirely bank my application on this or like that to solve the thing.

“In terms of what is going on in the community, I feel there's just this false dichotomy of this either evals is going to solve everything or online monitoring or production monitoring is going to solve everything. And I find no reason to trust one of the extremes in the sense that I will entirely bank my application on this or like that to solve the thing.”
Speaker
Kiriti Badam
Publisher
Lenny's Podcast

12 / belief

I think be foolish enough to believe that you can do anything if you put your heart to it, especially now because you have so much data at your hand that could be pointing towards the fact that you probably will be unsuccessful.

“I think be foolish enough to believe that you can do anything if you put your heart to it, especially now because you have so much data at your hand that could be pointing towards the fact that you probably will be unsuccessful.”
Publisher
Lenny's Podcast

13 / evaluation

Successful companies right now building in any new area, they are going through the pain of learning this, implementing this and understanding what works and what doesn't work.

“Successful companies right now building in any new area, they are going through the pain of learning this, implementing this and understanding what works and what doesn't work.”
Speaker
Kiriti Badam
Publisher
Lenny's Podcast

14 / prediction

The product has kind of been built so that your intention can be converted into a particular action and you kind of are clicking through a bunch of buttons, options, forms, and all of that, and you finally achieve your intention. But now that layer in AI products has completely been replaced by a very fluid interface, which is mostly natural language, which means the user can literally come up with a ton of ways of saying or communicating their intentions.

“The product has kind of been built so that your intention can be converted into a particular action and you kind of are clicking through a bunch of buttons, options, forms, and all of that, and you finally achieve your intention. But now that layer in AI products has completely been replaced by a very fluid interface, which is mostly natural language, which means the user can literally come up with a ton of ways of saying or communicating their intentions.”
Publisher
Lenny's Podcast

15 / prediction

Imagine you are a company who has a lot of customer support tickets and why even imagine OpenAI is the exact same thing when we were launching products and there was a huge spike of support volume as we launched successful products like Image or GPT-5 and things like that.

“Imagine you are a company who has a lot of customer support tickets and why even imagine OpenAI is the exact same thing when we were launching products and there was a huge spike of support volume as we launched successful products like Image or GPT-5 and things like that.”
Speaker
Kiriti Badam
Publisher
Lenny's Podcast

16 / observation

I want to take two steps back and kind of talk about how much weight the term evals has had to take in the second half of 2025 because you go meet a data labeling company and they tell you our experts are writing evals and then you have all of these folks saying that PMs should be writing evals, they're the new PRDs.

“I want to take two steps back and kind of talk about how much weight the term evals has had to take in the second half of 2025 because you go meet a data labeling company and they tell you our experts are writing evals and then you have all of these folks saying that PMs should be writing evals, they're the new PRDs.”
Publisher
Lenny's Podcast

17 / evaluation

We're still so busy building AI products that we're not worried about security, but it will be such a huge problem to kind of, especially with this non-deterministic API again. So you're kind of stuck because there are tons of instructions that you could inject within your prompt and then it's going really bad.

“We're still so busy building AI products that we're not worried about security, but it will be such a huge problem to kind of, especially with this non-deterministic API again. So you're kind of stuck because there are tons of instructions that you could inject within your prompt and then it's going really bad.”
Publisher
Lenny's Podcast

18 / recommendation

What that means is constrain the number of decisions your AI systems can make and make sure that they're humans in the loop and then increase that over time because you're kind of building a flywheel of behavior and you're understanding what kind of use cases are coming in or how your users are using the system.

“What that means is constrain the number of decisions your AI systems can make and make sure that they're humans in the loop and then increase that over time because you're kind of building a flywheel of behavior and you're understanding what kind of use cases are coming in or how your users are using the system.”
Publisher
Lenny's Podcast

19 / observation

Recently, I think Air Canada had this thing where one of their agents predicted or hallucinated a policy for a refund, which was not part of their original playbook, and they had to go by it because legal stuff.

“Recently, I think Air Canada had this thing where one of their agents predicted or hallucinated a policy for a refund, which was not part of their original playbook, and they had to go by it because legal stuff.”
Publisher
Lenny's Podcast

20 / recommendation

I think we did cover a bunch of best practices for AI products, which is start small, try to get your iteration going well and build a flywheel and all of that.

“I think we did cover a bunch of best practices for AI products, which is start small, try to get your iteration going well and build a flywheel and all of that.”
Publisher
Lenny's Podcast

22 / evaluation

The second one is the culture itself. And again, I work with enterprises where AI is not their main thing and they need to bring in AI into their processes just because a competitor is doing it.

“The second one is the culture itself. And again, I work with enterprises where AI is not their main thing and they need to bring in AI into their processes just because a competitor is doing it.”
Publisher
Lenny's Podcast

23 / preference

I think to add on to that, I feel like persistence is also something that is extremely valuable, especially given that anybody who wants to build something, the information is at your fingertips even more than the past decade.

“I think to add on to that, I feel like persistence is also something that is extremely valuable, especially given that anybody who wants to build something, the information is at your fingertips even more than the past decade.”
Speaker
Kiriti Badam
Publisher
Lenny's Podcast
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