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Amith Nagarajan

Things Amith Says on Podcasts

Chairman of Blue Cypress, a group of companies built for the association and nonprofit sector, and an early-stage investor in B2B software. His beat is practical AI adoption inside associations: what leaders are actually shipping, and where the risk sits in a deployed system. He co-hosts Sidecar Sync with Mallory Mejias, a weekly show on AI news and trends for association executives, and has spoken at industry gatherings including the ASAE annual conference.

Where to Find Them

Amith Nagarajan hosts and writes Sidecar Sync .

Recently: “Fundamentals of AI, Part 3 | 155” on Sidecar Sync (October 2026); “Jev Kicks Off the Decision Model Era, OpenAI Pulls GPT-6.1 Astra, & Waymo Outdrives Us | 154” on Sidecar Sync (October 2026); “Jev Kicks Off the Decision Model Era, OpenAI Pulls GPT-6.1 Astra, & Waymo Outdrives Us | 154” on Sidecar Sync (October 2026); “Why Vibe Coding Still Needs Engineers with Han-Shen Yuan | 153” on Sidecar Sync (September 2026); “Why Vibe Coding Still Needs Engineers with Han-Shen Yuan | 153” on Sidecar Sync (September 2026); “Will AI End Us All? | 152” on Sidecar Sync (September 2026).

What They Said

“The safety, in my opinion, comes more from what we call the harness, which is how you hold the model and how you interact with the model than the model itself.” — Amith Nagarajan, Sidecar Sync

Co-host Mallory Mejias asks whether smaller, cheaper models are also safer than frontier ones because they are less capable. Nagarajan says that is the wrong place to look. He points to a cheap open-weights model that could still do real damage if you spun up thousands of instances with unfettered tool access, and to things like how long an agent is allowed to run as the levers that actually matter.

Sidecar Sync · 2026-09-17 Permalink → Listen →
Sidecar Sync Around 39:11 into the episode
Amith Nagarajan

Well, you start off with the idea of keeping the data in an environment that you control. And most associations have challenge with this because the data itself is something they don't really control because it's, you know, it's scattered about in an AMS and an LMS and a SharePoint and all these other places. And they don't have one unified physical location where all their data is under lock and key. So that's, that's a problem that is solvable. And there's a number of technologies that can help you with that. We've mentioned on our pod a number of times the open platform we have called Member Junction, which is totally free to the association community. We knew this problem was going to arise and we built this platform starting five years ago for exactly this purpose to house the business data, both structured and unstructured, that could then basically be used in AI workloads, but in an environment the association had 100% ownership of. So that's the data in the ground as well, in a sense, because it's the execution environment too. There are other ways to do it outside of MJ. This is just the open free solution built for this sector. So we talk about it a lot, but there are other ways to do this as well. There's platforms like Databricks. You can bring data into Microsoft Fabric. There's other places that are environments where you can bring your data in. They all have their pros and cons, obviously.

Mallory Mejias

I want to talk about the idea of controlling the model. So Frontier models are one option, but not necessarily the default. A smaller, faster, cheaper model is often the better fit. And of course, switching should be cheap. Can you help us make the case for the smaller model, Ameth? And I'm also curious, do you think, because we talk about them being smaller, faster, and cheaper, do you also think they're safer because they may not have the overall intelligence level of a frontier model?

Amith Nagarajan

The safety, in my opinion, comes more from what we call the harness, which is how you hold the model and how you interact with the model than the model itself. You can do really bad things with small models if you just let them run amok. You could take, you know, something like GPT OSS 120B, which was a model released in August 2025. It's not a very intelligent model. You can run it very cheaply, though. And so if you wanted to spin up hundreds or thousands of instances of this much smaller model, that model could probably do some damage if you gave it unfettered access to a variety of tools and gave it a bad objective. So it's not that the smaller model is inherently safer. It's how you use the models. I would argue that the smaller models, though, are absolutely what you need to be using for most things. You know, I've talked in the past about sending a paper clip from LA to San Francisco or LA to New York and using a jumbo jet to do that, right? It's the wrong vehicle for that workload. And you don't need the biggest, most powerful model to do a small job. It's inefficient. It's slow. It's expensive. And possibly it could be less safe. But most importantly, it's just much more scalable if you use smaller models. The speed you get out of smaller models is stunning too. If you're used to your AI applications just being really slow, probably you're using a big and an older model. A lot of people, by the way, they'll set up some kind of an agent or an app and they'll be running on like, oh, I don't know, GPT-4.0 or something like that. And they just never bother to update it. And you ask them, well, how come you haven't done it? They're like, well, we just haven't gotten around to it or we haven't tested the newer models. But yet, oh, well, it's been two and a half years since that model was considered current. And sometimes those models get deprecated, right? And those models aren't undergoing new safety testing, new safety evaluations. They're just sitting there as they were. So actually being current and leveraging the right models for the job is an important part of your safety posture.

Mallory Mejias

Another thing you can control is the autonomy of your agents. Recursive self-improvement is the thing driving the fear in a lot of the conversations. That we've had thus far. And it's a dial, not a switch that flips when you start using AI. So, Ameth, in a controlled environment, what are the actual levers on how much a system can modify and improve itself?

Amith Nagarajan

Well, there's a lot of them, actually. And so, these different knobs or levers that exist on this machine that you're building, you have a lot of control over this. So, one of the things is actually just the budget you give to the agent. So, how long can the agent run for? If you give the agent days and days of time to run, which is, by the way, what happened with OpenAI's example, is they essentially had unlimited run time and they're not monitored really, and they're just doing their thing. Yeah, stuff potentially can happen. There's a lot of other ingredients needed to let things happen, but you can also set budgets that are like, well, you can run 30 times or 50 times or for 30 minutes. So, if you have narrower execution windows, that's both a budget constraint, but it's also potentially a safety component for control. Another thing, though, is really the tools or the capabilities that you give to the agent. So, if you imagine the world's smartest human and you put that person in a room and you give them no access to any tools whatsoever, there's very limited things they could do. They'd probably figure something out over time, maybe, if you gave them unlimited time because they're the world's smartest human. But if you gave them limited time and you didn't give them any tools, there's very limited things they could do. You give certain tools that are more general purpose in nature. They can be very powerful. Like, for example, you give Google search to an agent. That's actually a very powerful tool. If it can search the entire internet, it can get all sorts of information. Well, if you want to give it search, maybe you give it search just to one or two particular domains, or you give it narrow search just to internal document repositories that are scoped even more narrowly, right? So, that's that's part of the idea is that you give it kind of the least necessary level of permissions, which is like a very common thing that people teach in cybersecurity is that you grant the permissions that are needed, not like you don't just say, hey, everyone coming into our HubSpot instance, you're all super admins.

Speaker 3

That would

Speaker names from our own diarization · position estimated from where the line sits in the episode
“I'm a technologist at heart. I love the technology. It's fun, but I don't care about it at the end of the day. What matters is whether or not we as associations, like broadly, are advancing our missions or not.” — Amith Nagarajan, Sidecar Sync

Nagarajan was describing what he saw at the ASAE annual conference, where association leaders had moved past experimenting and were actually shipping AI work. He has, in his own words, been beating the drum about AI for years, which makes the disavowal at the end of the answer the surprising part. The measure he offers instead is whether members' lives are better, not whether the technology is impressive.

Sidecar Sync · 2026-08-27 Permalink → Listen →
Sidecar Sync Around 04:13 into the episode
Amith Nagarajan

And we are your hosts. And as usual, there's nothing happening in the world of AI. So I think we're done for the episode, right, Mallory?

Mallory Mejias

Yep, 30-second episode, everybody. Thanks for tuning in. Just kidding. We've got a lot to cover today. Amit, I know you are fresh off some travel to ASAE annual. How was that?

Amith Nagarajan

I loved it. It was so great. ASAE did a wonderful job putting together, they always do this. They're great at putting on events, but annual conference was a fantastic event. There were so many people there that were excited about just what's going on in general. And, you know, from an AI perspective specifically, every event that I go to, there's a progression in terms of kind of the frequency with which I talk to association leaders from large and small associations, from the most senior level positions down to folks that are earlier in their careers. And this progression I'm referring to is essentially really doing things, you know, hands-on doing things with AI. It's more than just experiments. It's gone way past that. And I find that exciting. I mean, we've been out here beating the drum about AI for quite a long time now. It was quite lonely for a while, and now it's not. And it's pretty cool to have a raging party going where everyone's, you know, coming to get excited about AI. But the most important thing is I'm hearing people talk about how it's helping them serve their members. It's not just about internal efficiency, but people are saying, hey, like I'm able to actually do AB and C to make my members' lives better because of AI. So technology is awesome. I'm a technologist at heart. I love the technology. It's fun, but I don't care about it at the end of the day. What matters is whether or not we as associations, like broadly, are advancing our missions or not. And that's what I'm starting to see.

Mallory Mejias

Did you hear about any use cases from association leaders that surprised you? Because I feel like as much as we talk about and you think about this, it would be pretty difficult for you to hear about a use case that you hadn't already thought about. But I'm curious, have you heard anything recently where you said, oh, that's a good idea?

Amith Nagarajan

Mario, have you ever seen the video where there's, you know, there's basically a bunch of distractions going on in this video? I'm trying to remember exactly what it is, but it's essentially you're watching like a landscape and you're watching all sorts of people moving around. And they're saying like, oh, count the number of people that enter and leave the movie's frame or the video's frame. And people are like busy counting the number of people coming in, coming out. And there's like, oh, is it, was it 17 people? Was it 19 people? And see, you play this in a room full of people and the video goes by and people are arguing about 17 versus 19 or 21. And then someone asks after about a minute or two of discussion, hey, did anybody see the eight foot tall gorilla walk through the room and wave at everybody? And the answer is like, what? We didn't see that. It's in the video. And then they play the video again. Instead of focusing on counting all the different individuals coming and going from the video frame, there's this giant gorilla in the background about halfway through that's like waving its arms like this and being silly. And presumably it was a person in a gorilla suit. I never actually checked it out. So, but it's a gorilla-esque creature. And but people didn't notice it is the point. So I guess the reason I bring that up, aside from the fact that it's just kind of fun, is when you are distracted day to day with a lot of tasks that are keeping you underwater, you miss big things. And so what is happening a lot of times in associations is you talk to people, let's say, who are in member services roles, and they are inundated with one email after the next email, after the next email. And these are smart people who care about your mission, who know your members. They know a lot about the domain. And all they do all day long is count people coming in and out of that video frame and they don't have time to think at all. And so they miss the gorilla. They miss the big opportunity. And what's exciting is that if you can save some time, increase efficiency, and then give your people a little bit more breathing room to take a breath and actually look around and say, hey, what's going on with our members? What's happening? They actually realize there's opportunities to serve your members better, right? There's a lot of bottom-up organic idea generation because you're no longer starved of oxygen in that creative process. So that is part of what's happening that I find exciting is people saying, you know what? This thing, this board deck that used to take me 40 hours to prepare once a quarter, it took up a whole week. Now it takes me 40 minutes to prepare it and it's better quality. And I spend that 40 minutes vetting the content. Previously, it was kind of this, you know, horrible like process. And now it's so automated that I can actually think about it. And then I'm able to reclaim that leak, do more actual thinking about what I should be talking to the board about, and then maybe even have some time left over to do other things, right? So that to me is the opportunity is you make some savings happen and then you invest that in improving the experience.

Mallory Mejias

Wow. I love a good analogy, Amith. I have not seen the video you're talking about. I'll have to go find it after we record this, but I'm going to try to carry this through line throughout the episode of finding the gorilla and making sure you're open enough to see it when it walks in the room.

Speaker names from our own diarization · position estimated from where the line sits in the episode