This Week in HeyCounsel (May 22, 2026)

Are specialized legal AI tools still worth it?; ethics counsel for the AI notetaker era; plus NY Tech Week is bringing the community out IRL...

HeyCounsel Newsletter
HeyCounsel

Weekly Community Digest

May 22, 2026

35

Client
Opps

41

Questions
Answered

6

Upcoming
Events

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⚡ This Week in 30 Seconds

17 new client opportunities this week. Defense tech co-counsel, biotech patent litigation, CIPA privacy defense, entity formation, and more. See all  Members
Are specialized legal AI tools still worth it? A benchmark post sparked a 39-reply debate. Real practitioners, honest disagreements, useful signal. See this week's Community Spotlight. Read the thread  Members
NY Tech Week is pulling the community together. NYC and Boston-area members are organizing co-working and meetups the week of May 25-30. Jump into #nyc if you're around.  Members
Next event: Perfect Form Demo and Q&A -- this Wednesday, May 27. A lawyer-founded entity management platform. Free to attend. RSVP here
 

🔥 Community Spotlight

Are Specialized Legal AI Tools Still Worth It?

A member shared a benchmark published by a legal AI platform this week comparing their performance against raw foundation models. The result that got people talking: the gap between the specialized tool and raw ChatGPT was narrower than most expected.

The thread ran to 39 replies. It covered real ground -- whether improvements from 75% to 80% pass rates materially reduce how much manual review you're doing, whether the real cost of raw LLMs is build and maintenance time rather than the subscription price, and how fast foundation models are closing in on domain-specific tools. One angle that came up more than once: MCP integrations may shift this comparison significantly. Once legal-specific tools build them, the context-switching friction that makes raw models less attractive starts to go away.

Read the thread →  Members

 

💬 Threads of the Week

How Members Build Their Contract Playbooks →

A member asked how everyone went about putting their contract playbooks together. The thread covers the practical side -- how to scope them, what to include, and the tradeoff between building something comprehensive and something lean enough you'll actually use. Useful read if you're trying to systematize contract review and don't want to start from a blank page.  Members

Claude Teams for Your Firm: Data Privacy and the Seat Question →

Several members are evaluating an upgrade to Claude's Teams plan -- mostly for the DPA and no-training guarantees. The thread got practical: what does the "primary account owner can export all chats" caveat mean for client confidentiality, and how are members thinking about extra seats? A creative workaround came up that a few members are already using. Worth reading if you're weighing the upgrade.  Members

Ethics Counsel for the AI Era →

A member asked for recommendations on external ethics counsel who can handle the issues coming up right now -- AI notetaker disclaimers in engagement letters, internal AI acceptable use policies, conflict check frameworks. Members offered referrals and stepped up to help directly. If you're trying to get ahead of this before bar guidance catches up, the thread has a useful shortlist.  Members

Workers' Comp for Solo Practices →

A member setting up payroll for a new solo PC asked whether workers' comp is required when you're the only owner and employee. The thread covered when you can elect to decline, what your payroll provider will want to see, and how the rules shift across states. Practical if you're spinning up payroll or about to make your first hire.  Members

All threads above are members only.

 

🏆 Community Win

Members in and around New York are organizing in-person meetups around NY Tech Week (May 25-30). Co-working sessions, evening events, and more have been taking shape in the #nyc channel -- with members traveling in from Boston to join.

This kind of organic, member-driven coordination is what this community is built for. If you're in the NYC or Boston area, check #nyc and see who's coming.

Apply to join HeyCounsel →

 

🚀 New Client Opportunities

A small sample of this week's opportunities -- members get access to the full list, plus the ability to submit proposals.

1. California Lease Agreement Review -- Flat Fee Engagement
2. NY Entity Formation + DBA for Event Planning Company
3. Defense Tech Co-Counsel Needed: ITAR/EAR Expertise
4. Co-Counsel for Biometric AI Startup -- On-prem OEM Deployments ($325/hr)
5. Biotech Patent Litigator -- Emerging Cancer-Detection Company
6. CIPA Pen Register Defense Counsel -- Series B HealthTech SaaS
7. Employment IP Agreement Review + Excluded Inventions Carveout

See all opportunities →  Members

Want access? Apply to join
 

📅 Upcoming Events

MAY
27

Demo and Q&A with Perfect Form

Perfect Form is a lawyer-founded corporate services company providing entity formation, registered agent, foreign qualification, and entity compliance services across all 50 states.

Register →
JUN
9

AI Notetakers and Your Law Practice

What should lawyers consider when using AI notetakers in their practice? Practical guidance on privilege, client consent, engagement letter language, and tool selection.

Register →
JUN
17

Build Your Firm Website with Claude Code

A hands-on session walking through how to build and launch a professional firm website using Claude Code -- no prior coding experience required.

Register →
JUN
18

Biz Dev Q&A with Megan Senese and K. Adam Bloom

A focused Q&A on business development strategies for independent practitioners -- what's working, what's changed, and how to build a sustainable client pipeline.

Register →
JUN
29

Contract Attorneys, Co-Counsel, and Of-Counsel Arrangements

A practical session on structuring co-counsel, contract attorney, and of-counsel relationships -- fee arrangements, ethics considerations, and how HC members are making it work.

Register →

Full calendar →

 

⚖️ Why Join HeyCounsel?

HeyCounsel is a vetted private community for solo and small firm lawyers. The idea is straightforward: independent practitioners deserve the same resources, relationships, and opportunities that large firms take for granted. Here's what membership includes:

✔️  New client opportunities and member referrals
✔️  Best practices for building AI-native firms
✔️  Relationships in a private Slack community of vetted peers
✔️  Exclusive discounts on tech & services, including Spellbook, GC AI, and more
✔️  Hundreds of member-contributed templates
✔️  Free CLEs, educational programming, and mastermind groups
✔️  Private demos, hackathons, and in-person events
Apply to Join HeyCounsel →
 

Have a great week,
Brian

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