Got a message from a user who said he was a huge skeptic before trying Caseway… then told me it “completely changed” his business. Also asked for a personal template folder feature, which is actually a solid idea. Wild what forty-nine bucks a month can do...

Last week I was a panelist at Victoria Tech Week, and being back in that environment reminded me how much the city has changed since I left a decade ago. Victoria used to feel like a place where ambitious tech founders eventually had to leave.

OpenAI’s new policy means ChatGPT can no longer provide legal, financial, or medical advice. That’s not just news; it’s a major shift in the industry. For legal tech companies that are basically ChatGPT wrappers, this is a serious problem. For Caseway, it’s validation.

Libraries matter. Access matters. After years of legal battles, the Internet Archive is still here—and still fighting for a world where everyone can read, learn, and remember. @arstechnica.com tells the story: arstechnica.com/tech-policy/...

Might start showing up on CBC every week soon as their resident AI guy 😏

Had a great time on Friday night and Saturday morning at The Justice Hack 2025, B.C.’s largest access-to-justice hackathon, hosted at McCarthy Tétrault in Vancouver. #AccessToJustice #LegalTech #Caseway #JusticeHack #VancouverTech #Innovation #LegalInnovation

It’s been a great week at Austin Startup Week. I came down as part of the Canadian delegation, where nine CEOs were selected to represent Canadian innovation and build new partnerships with Texas companies.

Everyone’s obsessed with the Caseway LED backpack.

New Zoom background unlocked: glowing Caseway sign. Now every meeting looks like it’s either: 1. A serious AI strategy session 2. Or the afterparty for one Either way, I’m keeping it lit.

This past week was one for the books. On Friday, I had the chance to pitch at The Syndicate in front of around 100 people. I shared my journey, from my time in the military, to building an e-commerce company.

✨ What an incredible evening! ✨ Team Caseway had the privilege of attending A Night to Inspire, a beautiful gala in support of InspireHealth Supportive Cancer Care. The event raised an amazing $765,000 for programs and services that help patients and families facing cancer.

Apparently Deloitte had to put up a sign reminding people not to drink the toilet water. To be fair, it’s not just any toilet water, it’s “LEED Platinum-certified rainwater reuse” toilet water. Sustainability: ✅. Hydration: ❌.

Really enjoying the Venture Founder program so far. Yesterday I had the chance to pitch in front of about 100 people, a great experience and a good test of the 30 second elevator pitch I’ve been refining. It's easy to explain what you do in 5 minutes, but very hard in 30 seconds.

Yesterday’s Keiretsu Forum Vancouver event at SFU Venture Labs was a great one. Heard some strong Series A pitches, connected with angels, and wrapped up with good conversations at Rogue Gastown. Always energizing to see this community in action. #VancouverTech #KeiretsuForum #AngelInvesting

🚨 7-Month Performance Review 🚨 Product: A Baby 👶 Delivery: 9 months + random rollout delays. Logistics were… rough. Launch: exceeded all KPIs. Lightweight at first, growth metrics now insane. Features: addictive “new baby” smell (limited edition), game-changing smile update.

An unforgettable evening with the Canadian Cancer Society, fashion, purpose, and breathtaking opera. ✨ A night that celebrated resilience, creativity, and community in support of cancer survivors. 💜 #CanadianCancerSociety #VancouverBC #EnBlanc

For the professionals and entrepreneurs laboring on Labor Day. Respect. 💪 #LaborDayWeekend #Startups

AI is out of control. And why do I look so beat up? lol

We’re in. Caseway has been accepted into the competitive Innovation UBC’s Venture Founder Fall 2025 cohort! Why this matters: tough intake, hands-on mentors, and a stage-gated build process that pushes teams to real traction.

Weekend = 2 events + 1 Grouse Grind. 🏔️ We’re building a Vancouver circle of action-doers (no scrubs). If you’re pushing, building, creating — DM me. 🚀

Our $1M USD raise at a $25M valuation closes September 15th and is already oversubscribed. If you or someone in your network wants to take a look before it closes, reach out to me directly for details. #AI #LegalTech #VancouverTech #Caseway

Caseway’s investor roadshow hit Langley! 🤠🐎 Horses, BBQ, cowboy hats, and great investor convos. Excited for the new partners joining us on this ride! 🚀

This is also a problem for Vancouver’s tech community. The city is full of high-net-worth individuals who made their money in real estate, yet many can’t (or won’t) put even $50,000 into a promising startup.

Next stop on the Caseway investor roadshow: Kelowna! 🍇☀️ Met with 15+ incredible investors, swapped big ideas over bigger coffees, and left with some exciting new future investors in the making. The Okanagan isn’t just good for wine, it’s for the future of AI too. 🚀 Accelerate Okanagan #kelowna

3 events. 1 night. Caseway fundraising mode: ON. Turning over rocks, chasing leads, and making deals. The round? 🔥 Absolutely crushing it.

Lawyers used to track every six minutes like it was sacred. Now, AI can do in seconds what used to take hours. Clients know it. Lawyers know it. The only people pretending otherwise? Firms clinging to outdated pricing models. alistairvigier.com/f/ai-is-kill...

Lyra's first message to me 😂

It’s always good to shake things up. Stepping outside your usual routine, even briefly, can reset your brain, spark new ideas, and remind you there’s more than one way to live a day. Whether it’s a new place, a new habit, or just a different route home, change forces awareness.

Beautiful day at the Caseway office!

🚨 Caseway is now powering legal AI in the U.S. We’ve teamed up with AffiniPay (parent of MyCase) to bring our court form + workflow tools to thousands of law firms. A major step for Canadian legal tech. 🔗 www.biv.com/biv-rss-news... #LegalTech #AI #Caseway #MyCase #JusticeTech

We are still in the trending spot after 2 days!

I posted a photo of my car after getting it wrapped, and a surprising number of people assumed it was AI-generated. That says a lot about where we’re at online. We’re now defaulting to disbelief. The line between real and fake is so blurred.

AI made this advertisement for Caseway. What do you think?

"AffiniPay, the parent company of MyCase, LawPay and other law practice management products, has entered into a partnership with Canadian AI company Caseway that will bring automated court form filling capabilities to MyCase practice management software users." www.lawnext.com/2025/07/affi...

💼🌀 When dealing with the law is more twisted than Saul... Better use Caseway. 📄 Automate court forms 📚 Power through legal research 🛡️ Keep your data yours 👉 Everyone needs smarter tools. www.caseway.ai #LegalTech #Caseway #BetterUseCaseway

Read about my thoughts on Tech Radar: "When Cloudflare announced its new Pay-Per-Crawl marketplace, some people saw a breakthrough. The idea is that if AI companies want to crawl your website to train their models." www.techradar.com/pro/cloudfla...

Some massive news. Caseway going into thousands of US based law firms: "Caseway Becomes First Canadian AI Firm Embedded in U.S. Legaltech Platform" www.fintech.ca/2025/07/16/c...

"Hey there Legal Rebels! 👋 I'm excited to share with you the 27th episode of the 2025 season of the LawDroid Manifesto podcast, where I will be continuing to interview key legal innovators..." www.lawdroidmanifesto.com/p/the-casewa... #legaltech #law

A fun kickoff to the The International Conference on Machine Learning! #ICML2025

Check it out!

“The definition of insanity is doing the same thing over and over and expecting different results.” alistairvigier.com/f/ai-is-kill...

What it feels like being in AI: lawsuits flying, billion-dollar valuations landing.

AI generated ad. What do you think?

MAJOR ANNOUNCEMENT: Caseway Launches Voice AI! 🎙️ The legal AI revolution just found its voice. We’re thrilled to announce the newest upgrade to Caseway’s platform: Voice AI is here, and it’s going to change the way you interact with legal data forever.

🚀 Using Caseway is like having a lawyer in your pocket, a nod to Steve Jobs' "1,000 songs in your pocket." #LegalTech #AI #Caseway #Innovation #DigitalLawyer #LegalAutomation