HeyCounsel Newsletter
HeyCounsel

Weekly Community Digest

June 24, 2026

25

Client
Opps

29

Questions
Answered

3

Upcoming
Events

Join the Pack

This Thursday · June 25 · 10am PT

Demo and Q&A with Parachute

"The complete legal operating system," Parachute is a legal AI platform built for small firms and solos. Members have been hearing (and experiencing) good things and we're excited to check it out ourselves. Show up with questions.

Register →

⚡ This Week in 30 Seconds

25 new client opportunities posted this week. Trademark enforcement for a CPG manufacturer, DCC enforcement defense for a California cannabis microbusiness, employment discrimination defense for an executive, and more. Members see the full list and can submit proposals directly. See all  Members
18 members weighed in on which AI tools are actually worth using for law firm work. The Perplexity vs. Claude vs. Gemini thread ran 18 replies and covered data privacy settings, Office integrations, and when search-first AI beats document-first -- or doesn't. See the Community Spotlight for the full breakdown. Read the thread  Members
NBI is recruiting HeyCounsel members to speak at a November virtual CLE. "The Business of Law: 10 Pillars of a Thriving Legal Career" -- November 5, 2026. Looking for 4-6 speakers, deadline July 17. Interested members should respond directly to Nicole Vandermoss at NBI. See the post  Members
Two new members introduced themselves this week. A former CFPB and FHFA regulator now running her own compliance and AI governance practice in DC, and a BigLaw/Alphabet veteran now at a boutique focused on VC and emerging companies. Say hello  Members
 

🔥 Community Spotlight

The AI Tool Comparison the Community Actually Needed

The question was simple: Is anyone using Perplexity for law firm work, and is it worth it? The 18-reply thread in #08-vendors-and-tech is one of the most honest AI tool conversations the community has had in a while. Members laid out exactly how they use Perplexity, Claude, Gemini, and Grok -- and where each one actually fits into a real workflow. The data privacy question came up early (which tools train on your data, how to turn it off, who defaults to no-training on paid plans). One member noted that Perplexity's strength is search-aggregation but Claude's document interaction is meaningfully different for legal work. Another flagged that Perplexity now has Office integrations that are genuinely useful for firms running on Word and Excel.

The thread didn't reach a consensus, which is probably the right answer -- different tools for different workflows. Worth reading if you're still figuring out your AI stack.

Read the thread →  Members

 

💬 Threads of the Week

Are You Buying a Separate Cyber Policy? →

A member asked whether solos and small firms are picking up a standalone cyber policy on top of malpractice -- and if so, through which carrier. Seven replies, three different carriers mentioned: Chubb, Cowbell, and ALPS. The ALPS portion of the thread got specific: members shared actual account manager names and contact details for people who answer the phone. If you've been putting this off, the thread has enough to get you started.  Members

Finding a Specialist Broker for Hard-to-Insure Clients →

A member needed a broker comfortable with early-stage, pre-revenue companies deploying industrial equipment -- the standard platforms didn't fit. Five replies and multiple broker recommendations with direct contact info came back. A useful resource if you're fractional GC for a startup and the default options keep returning declines or coverage gaps.  Members

How Are You Billing for Travel? →

A member asked the community what the actual practice is for billing when you travel out of state for a client transaction. Four replies, all landing on the same answer: bill full costs for flights and hotel, bill half-time for travel, and only bill for time actually spent working on-site. Simple, but it's the kind of question people don't want to ask.  Members

All threads above are members only.

 

📢 Member Programs & Perks

Virtual Coffee Chats

Want to meet someone new this month? Join the #virtual-coffee-chats channel to get matched 1-on-1 with another member. Expand your referral network, meet someone new. If you connect in person, HeyCounsel covers the coffee.  Members

Weekly Meditation & Mindfulness

A member facilitates a 30-minute guided community sit every Thursday at 9am Pacific / 12pm Eastern. Beginner friendly, no minimum commitment -- drop in whenever. Join the #meditation_mindfulness channel to be added to the recurring invite.  Members

 

👋 Welcome to the Pack

Two members who introduced themselves this week. Say hello in #02-introductions.  Members

Ashlie Tarpley · Washington, DC

Regulatory attorney and founder of her own practice, focused on helping businesses in regulated industries build the legal and compliance infrastructure to scale responsibly. Her background includes federal regulatory work at the CFPB and FHFA, plus a stint as the inaugural Data Privacy Officer at Pentagon Federal Credit Union -- over a decade in financial services total. Her practice covers regulatory compliance, AI governance, privacy, contracts, and entity formation. She's also building a fraud risk tool for the payments ecosystem, so she knows what it looks like from the founder side too.

Olivier Sinoncelli

Corporate attorney focused on VC and emerging companies, recently joined a former Goodwin colleague at a boutique. He started in BigLaw (Orrick, Goodwin, Cooley), moved in-house to 500 Startups and then Alphabet, and landed here. If you work with early-stage or growth-stage companies, worth connecting.

 

🚀 New Client Opportunities

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

1. Trademark Infringement Assessment and Cease-and-Desist for a Consumer Goods Manufacturer →
2. NY Employment Dispute -- Contractor Unemployment Claim Defense for a Startup →
3. California DCC Enforcement Defense →
4. Employment Defense Counsel for Executive Age and Race Discrimination Claim →
5. Florida Startup Counsel -- AI Security Tech Company (Partnerships, Seed Funding, Developer Agreements) →
6. UK Corporate Counsel -- SSHA and AoI Alignment with Term Sheet, Commercial T&C Update for Early-Stage Financial Services Company →
7. California Litigation Counsel for Federal Antitrust Subpoena Document Production →

See all opportunities →  Members

Want access? Apply to join
 

📅 Upcoming Events

JUN
25

Demo and Q&A with Parachute

A legal AI platform built for small firms and solos. Brian's seeing it for the first time Thursday at 10am PT -- members have been hearing good things. Show up with questions.

Register →
JUN
29

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

How to use these arrangements to scale your practice without hiring -- structure, economics, malpractice considerations, and how to build relationships that actually work.

Register →
WKL
THU

Weekly Meditation & Mindfulness -- 9am PT / 12pm ET

A member facilitates a 30-minute guided sit every Thursday. Beginner friendly, drop in whenever. Join #meditation_mindfulness to be added to the recurring session.

 

👥 Join HeyCounsel

HeyCounsel is a private community for independent attorneys and small law firm owners. If you're building or running a practice on your own terms, here's what you get as a member:

• New client opportunities and member referrals -- like the 25 posted just this week
• Best practices for building AI-native firms -- from lawyers who are actually doing it
• A private Slack community with practitioners across every area of law
• Exclusive discounts on legal AI tools and services, including Spellbook, GC AI, and more
• Hundreds of member-contributed templates across every practice area
• Free CLEs, educational programming, and mastermind groups
• Private demos, hackathons, and in-person events when the pack gets together

If you're an independent attorney or running a small firm, this is the room you've been looking for.

Apply to Join   Learn More
 

Have a good week,
Brian
Founder, HeyCounsel

Share this issue → Apply to join →

© 2026 HeyCounsel · heycounsel.com · Unsubscribe

Recommended for you