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- From 80 Rejections to $350M: Spellbook’s Next Growth Move
From 80 Rejections to $350M: Spellbook’s Next Growth Move
Inside Spellbook's US$40M move, what's happening on the West Coast, and everything coming up in the community.

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4,000 customers. 80 countries. $100M ARR in sight.
If you haven't heard of Spellbook yet, here's a quick overview: they've built the first generative AI copilot for lawyers. Lawyers use it to draft, review, and edit legal agreements directly within Microsoft Word. Founded in 2018, backed by N49P and Khosla Ventures, and valued at US$350M after their Series B last year.
This week, they added a US$40M debt line from RBCx - and they're putting it to work.
"It's a good strategy for us to bolster our team and get to a larger level of maturity quickly so that we can execute on the opportunities in front of us."
The numbers behind the move:
‣ 3x revenue growth in 2025
‣ US$100M ARR on track by year-end
‣ 4,000+ customers across 80 countries - including Nestlé, Dropbox, eBay, AtkinsRéalis and Franklin Templeton
‣ 40,000 lawyers, judges, notaries & law students via exclusive Canadian Bar Association deal
‣ 100 new hires planned by the end of 2026, on top of a current team of 150
The plan: five acquisitions, up to US$60M in cash and stock, within two years. The goal isn't just growth - it's building the definitive platform for legal AI.
The market has matured quickly, and Spellbook is stepping up to bring the best of it together under one roof.
Last December, Scott Stevenson (CEO & Co-Founder, Spellbook) joined Alex Norman and Alexandra Reilly on our Founder Journey podcast - 57 minutes on seven years in the sludge, 80 investor rejections, and how Spellbook built a data moat spanning millions of contracts across 80 countries.
"We were always on the leading edge because we were always willing to drop the axe and pick up the chainsaw."
🏆Best Of 2024 → Best Of 2026
Two years ago, Scott stood on our Best Of stage and said, "Lean perseverance works."
At the time: 1,700 law firms. A $27M raise. A dual HQ between St. John's and Toronto.
Today: 4,000+ customers across 80 countries. A $50M Series B led by Khosla Ventures. A $350M valuation. And now a US$40M fund to fuel what comes next.
The next founder writing that story is taking our stage on April 13. You just don't know who it is yet. That's why you should be there.
📅 Monday, April 13 | 6:00 PM - 8:30 PM |📍 Toronto City Hall · 100 Queen St W, Toronto

If you're building in Canada in 2026 - whether you're trying to raise, trying to sell into enterprise, or trying to figure out if you even need capital - the West Coast is doing something worth watching. These three Together Vancouver talks will save you months of hard lessons.
Sina Afrooze: Fundraising Like a Sales Process (Apera AI → BC Growth Company of the Year)
Sina built Apera AI - a robot vision platform for manufacturing - to 85 people and a top-10 Deloitte Fast 50 ranking by treating fundraising exactly like a sales pipeline: prospect, qualify, and disqualify fast. He hired a professional speechwriter (the kind who works for politicians) to turn his pitch into a conversation, and cracked the manufacturing sector by landing one plant at a time before climbing to corporate.
Why watch in 2026: His VC qualification framework is underused by early founders - ask if the partner is actually on the call. If not, walk. His manufacturing GTM motion (bottom-up, plant-by-plant → top-down, corporate) applies to any B2B hardware or industrial AI company. Plus: the subtle Zoom trick of saying your investor's name mid-sentence to pull them back into the room.
Scott Elliott: Bending the Odds (Slate → Flipping "No" to "Yes" in a Week)
Scott is a trained actuary who spent a decade as the risk professional before co-founding Slate, an embedded financing platform for vertical SaaS and fintech companies. Building offence as a naturally defensive thinker has been his sharpest skill and greatest challenge. He turned a VC rejection into a term sheet within a week - not by changing the pitch, but by moving fast enough that the investor could see the odds shift in real time.
Why watch in 2026: He explains exactly what changed his mind: weekly updates, radical transparency, and a faster pace of iteration than he's seen in Canadian fintech. Scott also discusses why embedded finance through trusted platforms is the key to unlocking growth in Canada - US borrowers trust fintechs, Canadian borrowers only trust banks, and banks often don't serve SMBs. Speed as proof of conviction remains the main framework.
Simon Wong: Bootstrapped for 10 years (Pixieset → 1M+ Users, Zero Marketing Budget)
Simon and his wife Phoebe bootstrapped Pixieset - a vertical SaaS for professional photographers - for nearly a decade, ignoring every investor email for 10 years. Two people. First paying customer in July 2013. By 2021, they had 25 employees, were cash-flow positive, and finally opened their inbox to raise a Series A. They grew to 200 people, acquired a design agency in Moldova, and closed the deal one week before the war in Ukraine started.
Why watch in 2026: Simon's story offers a counter to the raise-first culture. His PLG approach was built in from the start - every photo gallery shared included a Pixieset URL, turning each client delivery into a distribution channel. He monitored one metric for eight years: "Is the bank account growing?" For anyone building a quiet, compounding SaaS business without a marketing team, this one's for you.

U of T Entrepreneurship Week is back, running March 2-6 across three campuses. Today's highlight is one for anyone serious about Canada's AI future.
TODAY: Canada's Next AI Movement - Ambition the World Can Trust
📅 March 5 | 4:00-5:30 p.m.
🖥️ Watch the livestream
Alán Aspuru-Guzik, Christine Allen, and Milica Radisic - three of U of T's most renowned minds - are gathering for a candid conversation on where AI is headed and what it takes to lead responsibly.
Also today: U of T's largest pitch competition - founders competing for the Desjardins Startup Prize, with $100,000+ in rewards.
Growth Table: CIX Summit: Tuesday, March 24 @ 6:00pm - REQUEST TO JOIN
CIX Summit Afterparty: Wednesday, March 25 @ 5:30pm - GET YOUR TICKETS
TechTO community exclusive: Get 20% off CIX passes with code CIXTECHTO20
Best Of: Monday, April 13 @ 6:00pm - EARLY BIRD TICKETS
Commerce Toronto: Tuesday, April 21 @ 5:30pm - EARLY BIRD TICKETS
Don’t forget to lock in your year of TechTO! Subscribe to our full events calendar

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