Matthew Basile built Naya while billing two thousand hours a year as a senior associate at a large law firm. He licensed the platform back to his own employer, sold it to other firms, became a partner, and eventually ran into the wall that every LegalTech founder eventually hits when selling into a billable hour model: every hour you cut is revenue someone else in the building used to earn.

In this episode Matt covers the full picture: why selling to law firms was the wrong model and what made that clear, how a $40K fee to close a $2M mortgage loan forced him to throw out the model and run it like an ALSP, what happens when you promise a fixed fee and then lose money on a deal, why a 20-person team of well-equipped lawyers should be able to do the revenue of a 150-person firm, and why the AI native law firm conference in New York is exciting precisely because nothing is right or wrong yet.

Matt also talks about building MCP integrations with Claude, why AI agents sound better than they perform in complex deal space, why you still need a really good human in the loop, and what it feels like to ship something in a week that would have been technically impossible a year ago.

If you're building or selling in commercial real estate legal, interested in AI native law firms, or trying to understand what the transition from law firm to legal tech company actually looks like from the inside, this is the most honest version of that story.

Timestamps:
00:01 — What Naya does and who it's for
01:22 — Building Naya while billing 2,000 hours a year as a senior associate
02:04 — The tension between selling efficiency and billing hours
04:51 — Why selling into large law firms is harder than it looks
07:10 — Law firms as archipelagos: you've signed the firm, you've reached one partner
09:01 — The pivot: from law firm software to ALSP for mortgage lenders
11:23 -- $40K to close a $2M loan: why the big firm model didn't work
13:43 — Fixed fee deals, early losses, and what they taught him to automate
16:40 — AI first, tech first, but lawyers aren't going away in complex deal space
22:12 — LinkedIn content: why Matt started posting and what's working
25:50 — The channel mismatch: LegalTech audience vs mortgage lender buyers
28:25 — Why lawyers are scared to post and why that's an opportunity
33:48 — Can a 20-person team do the revenue of a 150-person firm?
35:01 — North Star: competing head to head with AM Law 150 for CRE finance deals
36:48 — Building MCP with Claude and what became possible last week that wasn't possible a year ago

🎙️ Taking LegalTech to Market is hosted by Paul Church, LegalTech recruiter, talent advisor, and one of the most listened-to voices in the space.

Subscribe for new episodes every week.

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Matt was a senior associate at a large law firm billing two thousand hours a year. He was also selling that same firm his own software. Every time it worked, someone in the building lost revenue. That tension doesn't resolve. It compounds.

In this trailer: why signing a 400-lawyer firm isn't the contract you think it is, why $40K to close a $2M loan forced him to throw out the model entirely, why losing money on fixed fee deals is actually R&D, and whether a 20-person team of well-equipped lawyers can do the revenue of a 150-person firm.

Naya's North Star: competing head to head with AM Law 150 firms for commercial real estate finance deals within two years.

Full episode going live on Friday on Taking LegalTech to Market. 🎙️

Jacob Adberstein came from NASA. His brother came from cybersecurity. Neither had a legal background. That turned out to be exactly the right perspective to see a problem the industry had stopped noticing, law firms are losing clients at the intake stage before a lawyer ever picks up the phone.

Reflekt Legal builds AI employees that handle reception and intake across voice, email, and SMS. The product isn't sold on efficiency metrics or cost savings. It's sold on something harder to replicate: the experience it gives to the people who call the firms that use it. Mexican-style service, as Jacob calls it, the kind that makes someone feel taken care of rather than processed.

In this episode Jacob covers the full picture: why almost all of their firms are still with them, why he tells customers not to buy when buying isn't right for them, why he'd rather be last in an evaluation than first, how the undercover boss audit motion became their most effective pipeline channel, and what 70 to 80% demo-to-close looks like when you stop optimizing for volume and start optimizing for trust.

If you're building or selling in LegalTech, hiring for a GTM role, or trying to understand what a referral-led growth engine actually looks like in practice, this is the most practical 30 minutes on all of it.

Timestamps:
00:00 — What Reflekt Legal does and who it's for
00:52 — Why an aerospace engineer and a hacker built a law firm AI
02:51 — Vibe coding vs building the actual tech
04:37 — Why almost all their firms are still with them
05:00 — Word of mouth as the primary growth engine in legal
05:43 — Why lawyers become your biggest advocates once you earn them
05:58 — Why vendors overcharge lawyers and why that makes trust so powerful
07:39 — Telling customers not to buy when buying isn't right for them
08:12 — The Mexican service philosophy: the product north star
13:01 — The undercover boss audit: borrowed from cybersecurity pen testing
16:02 — Why firms that are doing decent have never looked at intake
21:21 — 70-80% demo-to-close: what that conversion rate looks like
22:49 — Conferences as the highest-converting pipeline channel
23:42 — Company policy: every person, every role, works with AI
25:47 — What Jacob looks for when hiring salespeople
27:20 — North star for the next 12 months and what's coming soon

🎙️ Taking LegalTech to Market is hosted by Paul Church, LegalTech recruiter, talent advisor, and one of the most listened-to voices in the space.

Subscribe for new episodes every week.

Lawyers are the hardest buyers in any market. They've been overcharged by every vendor they've ever dealt with, and they remember it. Jacob Adberstein built Reflekt Legal knowing that, and built his entire GTM motion around earning trust rather than closing deals.

In this trailer: why he tells customers not to buy when buying isn't right for them, why he'd rather be last in an evaluation than first, how almost all of their firms are still with them, and why the slow and steady approach is exactly what leads to the hockey stick.

One converted lawyer who becomes an advocate is worth more than any ad budget. This is how you build that.

Full episode dropping soon on Taking LegalTech to Market. 🎙️

Maryam Salehijam walked out of a Stanford Law visiting research position into LegalTech sales, with no legal background, no network, and a PhD in something completely different. That outsider perspective is exactly why she sees things most people in this market miss.

In this episode Maryam breaks down the full picture: why the objection has shifted from "we don't trust AI" to "we're building our own," why she deliberately wants to be last in every evaluation cycle, why she tells buyers exactly where her competitors are better, and why you cannot sell AI to a burning out team.

She also makes the most counterintuitive commercial argument in the episode, she actively recommends smaller subscriptions when a larger one would benefit her, tells customers not to buy when buying isn't right for them, and says the moment you stop doing that is the moment you stop building a referral engine.

Maryam is ex CRO at Junior, an AI patent drafting platform. She ran the entire revenue function, lean, AI-enabled, with processes that run themselves.

If you're selling into legal right now, hiring for a GTM role, or building a CRO function from scratch, this is the most honest account of what that actually looks like in 2026.

Timestamps:
00:00 — PhD to LegalTech CRO: the Stanford Law corridor moment
04:41 — Why lawyers are miserable and why that matters to GTM
05:08 — Junior's ICP: patent prosecutors, in-house IP, trademark teams
06:28 — The best channel to reach your ICP in 2026
06:55 — Why email and cold calling are both dead
08:03 — Organic word of mouth as the primary growth engine
13:13 — The objection shift: from "we don't trust AI" to "we're building our own"
17:24 — Be last in the evaluation cycle, not first
19:07 — Why Maryam tells buyers who her competitors are and where they're better
20:55 — You cannot sell AI to a burning out team
21:47 — Three-year contracts before proving value: that's just selfish
22:53 — What Maryam looks for when hiring for GTM
23:36 — Why immigrants make great startup hires
24:55 — How AI has replaced RevOps, sales ops, EAs, and most BDRs
25:41 — The two automations that changed her sales process
26:42 — What success looks like for Junior in the next 12 months

🎙️ Taking LegalTech to Market is hosted by Paul Church, LegalTech recruiter, talent advisor, and one of the most listened-to voices in the space.

Subscribe for new episodes every week.

Maryam Salehijam is ex CRO at Junior, AI patent drafting. She's selling AI to lawyers. And she's also the person on the other side of your outbound sequence, watching salespeople ask questions that were already answered in the AI-generated email they clearly never read.

In this trailer: why she deliberately wants to be last in every evaluation, why she tells buyers exactly who her competitors are and where they're better, and why the only GTM motion that still works in legal AI is one built entirely on trust.

The objection used to be "we don't trust AI." Now it's "we're building our own." The playbook changed. Most people haven't noticed yet.

Full episode going live on Friday.

Nathan Mutter and Michael Drapkin were top outside counsel at Qualcomm, Micron, and Salesforce. When the ChatGPT moment hit, they didn't wait to see what would happen to their industry. They walked away from the most profitable position in the market and built Landfall IP, an AI native patent law firm, from scratch.

In this episode they break down the full picture: why they built a law firm rather than a software product, how their Discovery Agent removes the biggest barrier between inventors and patent protection, why people want to buy trust and judgment rather than a tool that produces a piece of paper, and what the Malcolm Gladwell risk reframe actually means for any practitioner still sitting on the fence.

MLD also makes the most important market observation in the episode: only 4% of total legal spend goes on technology. It should be 40%. Kirkland and Ellis is spending $500M over five years on building an AI platform. The firms willing to disrupt themselves are already diverging from the ones that aren't.

If you're building for the legal market, selling into it, or considering leaving a traditional firm to join an AI native one, this is the most commercially honest 40 minutes on where the industry is going.

Timestamps:
00:00 — What Landfall IP actually is and who it serves
01:04 — Why they left Qualcomm, Micron and Salesforce as outside counsel
02:11 — The Malcolm Gladwell risk reframe that made the decision make sense
03:32 — Nathan's background: from building missiles to patent law
05:19 — Why they built a law firm rather than a software tool
07:00 — Who they see as competition
08:30 — The AI execution layer and what world class patent drafts look like
10:00 — Pricing and accessibility: meeting clients where they are
14:00 — The Discovery Agent: removing the friction between inventors and patents
19:00 — How the interview process works and what clients experience
23:00 — Why domain credibility beyond surface level is the trust differentiator
28:00 — The quality tipping point: when it goes from nice to have to difference maker
33:09 — The innovators' dilemma: profits per partner go up every year
33:09 — Kirkland and Ellis spending $500M on AI over five years
35:36 — How AI is expanding who gets access to legal counsel
38:20 — Only 4% of legal spend is on technology. It should be 40%.
39:03 — The human element that still closes every deal

🎙️ Taking Legal Tech to Market is hosted by Paul Church — LegalTech recruiter, talent advisor, and one of the most listened-to voices in the space.

Subscribe for new episodes every week.

Profits per partner go up every year. That's exactly why most law firms won't change.

Nathan Mutter and Michael Drapkin were top outside counsel at Qualcomm, Micron, and Salesforce. When they saw what AI was going to do to their industry, they didn't wait. They walked away and built Landfall IP, an AI native law firm from the ground up.

In this trailer: the Malcolm Gladwell risk reframe that made the decision make sense, the innovators' dilemma that's keeping every profitable firm on the wrong side of the change, and the number that explains the entire opportunity, only 4% of total legal spend goes on technology. It should be 40%.

The firms willing to disrupt themselves are already diverging from the ones that aren't.

Full episode live tomorrow on Taking LegalTech to Market. 🎙️

First demo: four years ago. Closed: last week. And that's not the exception, that's what selling into large law firms actually looks like when you're nine years in and still showing up.

Eimear McCann is Commercial Director at TrialView, an AI disputes platform built for the full lifecycle of litigation. She joined in 2021 when the incumbent was so embedded that buyers genuinely thought they had a contract with the courts. What followed was two years of pure education, not selling, just proving that alternatives existed.

In this episode Eimear covers everything that's changed since then: why free pilots with dummy data quietly kill your conversion rate before it starts, how the buyer's questions shifted from "why are you different?" to "what AI models are you using and where is the data hosted," why headline conference sponsorships only make sense if you're Harvey or Legora, and why outbound email had its golden era and it's over.

She also talks about what great looks like for TrialView in H2 2026, the new agentic case intelligence layer on the platform, and why even if AI became more expensive than a human lawyer the fundamental tools and workflows in law have changed now forever.

If you're selling into litigation technology, building for the disputes market, or hiring into LegalTech GTM, this is the most honest account of what that commercial motion actually looks like.

Timestamps:
00:00 — What TrialView does and who signs the contract
01:56 — Stakeholder mapping in large law firm sales
03:33 — Average sales cycle: 30 days to 4 years
03:52 — Joining in 2021 when buyers thought they had one option
06:01 — How the buyer conversation changed with the AI explosion
06:20 — Old questions vs new questions: credibility, data hosting, AI models
07:59 — AI-first vs domain-first: what buyers are really worried about
09:54 — Pilots: why 95% convert and what the other 5% have in common
11:29 — Free pilots with dummy data: two mistakes in one
12:36 — Success criteria: why pilots without them almost never convert
13:05 — What a tight pilot feedback loop actually looks like
14:00 — GTM channels: what's working and what isn't in 2026
17:10 — Outbound email: the golden era is over
18:00 — Events and conferences: ROI reality check
21:21 — Headline sponsorship only works if you're Harvey or Legora
22:50 — Community building and smaller tailored sessions
24:46 — What a great LegalTech salesperson profile looks like
26:37 — Do they need to be an ex-lawyer?
27:49 — What great looks like for TrialView by end of 2026
29:10 — Is it a bubble? What's on the other side?
31:37 — Why the workflows have changed forever regardless of what happens to AI

🎙️ Taking LegalTech to Market is hosted by Paul Church, LegalTech recruiter, talent advisor, and one of the most listened-to voices in the space.

Subscribe for new episodes every week.

The first demo was four years ago. The deal closed last week. That's not a failure, that's what selling into large law firms actually looks like.

Eimear McCann has been selling into litigation technology for nine years. In this trailer she covers the pilot mistakes that kill conversion rates, why free trials are worse than charged ones, why outbound email is over, and why headline sponsorships only make sense if you're Harvey or Legora.

And underneath all of it: even if AI became more expensive than a human lawyer, the fundamental tools and workflows in law have changed now forever.

Full episode live tomorrow on Taking Legal Tech to Market. 🎙️
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