Wednesday, June 25, 2025

AI networking in the Boston area

A lot's happening in Boston - where should I find out more?

There's a lot of AI work going on in the Boston area covering the whole spectrum, from foundational model development, to new AI applications, to corporates developing new AI-powered apps, to entrepreneurs creating new businesses, to students building prototypes in 12 hours. Pretty much every night of the week you can go to a group where you can find out more; there are a ton of different groups out there. But not all of them are created equal. I've been to a lot of groups and here are my recommendations for the best ones that meet on a regular basis. The list is alphabetical.

(Google Gemini)

AI Tinkerers

What it is

Monthly meeting where participants show the AI projects they've been working on. Mostly, but not exclusively, presentations from the Sundai Club (Harvard and MIT weekly hackathons). Attendance is over 150.

Commentary

This is where I go to when I want to see what's possible and find out more about the cutting edge. It's where I found out what tools like Cursor could really do. There are a number of VCs in attendance watching for anything interesting.

How often it meets

Once a month at Microsoft NERD.

Positives

You get to see what the cutting edge is really like.

Negatives

I found networking at this event less useful than some of the other events.

How to join

https://boston.aitinkerers.org/

AI Woodstock

What it is 

A networking event for people interested in AI. It attracts practitioners,  some VCs, recruiters, academics, and entrepreneurs. Attendee numbers vary, but typically over 100.

Commentary

This is networking only, there are no presentations or speakers of any kind. You turn up to the venue and introduce yourself to other people, and get talking. I've met people who are starting companies, people who are working on side gigs, and people who are working in AI for large companies. 

The quality is high; I've learned a lot about what's going on and what companies in the Boston area are doing. 

The venue is both good and bad. It's held in a corner of the Time Out Market near Fenway Park. This is a large space with lots of food and drink vendors, it attracts the bright young things of the Boston area who go there to eat and drink after work. AI Woodstock doesn't take over the whole space or rope off a portion of it and AI Woodstock attendees are only identified by name badges. This means you're chatting away to someone about their AI enabled app while someone is walking by with their drink and app to meet their friends. The background noise level can be really high at times.

How often it meets 

Once a month at the Time Out Market near Fenway Park.

Positives

  • Networking. This is one of the best places to meet people who are active in AI in Boston.
  • Venue. It's nice to meet somewhere that's not Cambridge and the food and drink offerings are great.

Negatives

  • Venue. The noise level can get high and it can get quite crowded. The mix of bright young things out to have a good time and AI people is a bit odd.

How to join

https://www.meetup.com/ai-woodstock/ - choose Boston

Boston Generative AI Meetup

What it is

This is a combination of networking and panel session. During the networking, I've met VCs, solo entrepreneurs, AI staff at large companies, academics, and more. Attendance varies, but typically over 200.

Commentary

This is held in Microsoft NERD in Cambridge and it's the only event in the space. This means it starts a bit later and has to finish on time. 

Quality is very high and I've met a lot of interesting people. I met someone who showed me an app they'd developed and told me how they'd done it, which was impressive and informative.

The panel sessions have been a mixed bag; it's interesting to see people speak, and I found out a lot of useful information, but the panel topics were just so-so for me. Frankly, what the panelists said was useful but the overall topic was not.

How often it meets

About once a month.

Positives

  • Networking. 
  • Venue.
  • Information. The panels have mentioned things I found really useful.

Negatives

  • Panel session topics were a bit blah.

How to join

https://www.meetup.com/boston-generative-ai-meetup/

PyData Boston

What it is

Presentations plus networking. This is almost all machine learning/data science/AI practitioners in the Boston area (no VCs, no business people, instead there are academics and engineers). The presentations are mostly on technical topics, e.g. JAX. Attendance varies, but usually 50-100.

Commentary

I've learned more technical content from this group than any other. The presentations are in-depth and not for people who don't have a goodish background in Python or data science.

How often it meets

Once a month, usually at the Moderna building in Cambridge.

Positives

  • Best technical event. In-depth presentations have helped educate me and point out areas where I need to learn more. Conversations have been (technically) informative.
  • Probably the friendliest group of all of them.

Negatives

  • No entrepreneurs, no VCs, no executive management.

How to join

https://www.meetup.com/pydata-boston-cambridge/

Common problems

There's a refrain I've heard from almost all event organizers and that's the problem of no-shows. The no-show rate is typically 40% or so, which is hugely frustrating as there's often a a waiting list of attendees. Some of these events have instituted a sign-in policy, if you don't turn up and sign in, you can't attend future events, and I can see more events doing it in future. If you sign up, go.

One-off events

As well as these monthly events, there are also one-off events that happen sporadically. Obviously, I can't review them here, but I will say this, the quality is mostly very high but it is variable.

What's missing

I'm surprised by what I'm not hearing at these events. I'm not hearing implementation stories from existing ("mature") companies. Through private channels, I'm hearing that the failure rate for AI projects can be quite high, but by contrast I've been told that insurance companies are embracing AI for customer facing work and getting great results. I've met developers working on AI enabled apps for insurance companies and they tell me their projects have management buy-in and are being rolled out.

I'd love to hear someone from one of these large companies get up and speak about what they did to encourage success and the roadblocks on the way. In other words, I'd like to see something like "Strategies and tactics for successful AI projects" run by people who've done it.

Your thoughts

I've surely missed off groups from this list. If you know of a good group, please let me know either through LinkedIn or commenting on this post.

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