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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: “Microsoft Pays Anthropic to Fix Copilot, Meta Returns to the Frontier, & Courts Put a Price on Your Content | 156” on Sidecar Sync (October 2026); “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).

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

…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

…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…

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…

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…

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

…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…

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…

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