Everything Ben Alarie said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Alarie: Horizontal LLMs generate flawed tax answers from stale web sources
“More commonly, there will be some of the materials that those systems find even on the open web are at a date anachronistic. The law has changed. There's been some statutory amendment or there's some new case law or, you know, some law firm wrote some guidance…”
Alarie: Blue J raised a $122M Series D in July 2025
“We raised a Series D round, and that closed in July of 2025. And it was a hundred and twenty two million USD.”
Alarie: Tax partners won't build startups due to high opportunity cost
“It might be a tax law partner in a big firm, but that's so extraordinarily unlikely because they already have clients that they're servicing. They're part of a partnership. They're kind of bought in. They kind of have dedicated their lives to that path. It cou…”
Alarie: Pure AI engineers won't solve tax research without deep domain mastery
“Might it be somebody who's more kind of pure tech, like an AI or machine learning background? And again, I thought, well, probably not because they would need to know a lot more tax law than they do. It'd take them a decade to catch up to where I was in my und…”
Alarie: Blue J's early ML models predicted court rulings with over 90% accuracy
“So we built a bunch of these different predictive models, which performed extremely well, like better than we thought they could perform. And so we're predicting with better than 90% accuracy, how courts would resolve these kinds of cases.”
Alarie: Reliable legal research synthesis was impossible before LLMs
“The big move was retrieval augmented generation, where you kind of run a search. So you have a master corpus of all of the relevant tax research materials. You run an intelligent search, and you've got, like, really good vector embeddings, and you're chunking …”
Alarie: RAG shifts legal AI effort from retraining models to data curation
“The brilliant thing about leveraging retrieval augmented generation is we can just curate the data. And if we're confident about the currency of the tax database and the content in the database, and we're confident about our retrieval algorithms, our Prompt en…”
Alarie: Blue J approaches 3,400 firm subscribers, adding 10 daily
“We've gone from fewer than a hundred firms subscribing at the end of 20, 23 to like 1200 ish at the end of 20, 24. Now we're closing in on 3400 firms who are signed up to Bluejay and every day it's like we're adding about another 10 Firms, new logos every sing…”
Alarie: Blue J reaches mid-$20M in ARR
“Well, yeah, now we're in the mid twenties millions of ARR.”
Alarie: Instant time-to-value reduces the social risk of word-of-mouth recommendations
“If I am confident that I make this recommendation to you and you can at very low cost go and like validate that for yourself right away, it makes it socially far less risky for me to suggest this to you because you can validate it for yourself extremely quickl…”
Alarie: Blue J reached over $5M ARR with initial product
“So yeah, we got it up to over five million dollars in ARR over several years.”
Alarie: Blue J grew from $2M to almost $9M ARR in 2024
“And we grew from like roughly two million in ARR to just shy of nine million dollars in ARR by the end of 20, 24.”
Alarie: Blue J was operating cashflow positive in 2024
“We were cashflow positive from operations in 20, 24, which is pretty cool as a startup.”
Alarie: Live, unscripted audience problem demos are essential for proving software capability
“In those demos, the audience always has like some reservations is like, oh, like maybe, maybe this is a cooked up example. And maybe this is like being presented to really over promise what this product can actually do, which is why I think it's always so powe…”
Alarie: Blue J's Net Promoter Score is in the mid-80s
“Like now I'm still, you know, our NPS is in the mid eighties and it's like, okay, well, let's keep going.”