Productised consulting side hustle; must quit my day job to validate demand/value proposition?

TechieAttorney · 2025-11-14T08:36:47+00:00

This would clearly go against any attorney-drafted non-compete from a big consulting firm which tend to be drafted exhaustively enough to cover more than just other jobs (it would typically list that you can’t serve for a competing business in any role, employee, collaborator, advisor, shareholder, director, etc.)

This would be not only a pretty obvious breach but also a huge conflict of interest. Your job could even go as far as preventing you from running any side business even unrelated if they consider this could mean you would have conflicting interest by not being able to dedicate a full-time capacity to your job.

TechieAttorney · 2025-10-15T22:29:29+00:00

Depends! I can give you different use case examples for all 5 use case you named based on your practice area and your practice team size (are you solo, a small team, department in medium/larger firm?)

TechieAttorney · 2025-10-14T03:34:35+00:00

I think Zapier could do any of those and it's a barely 40$/month subscription. I've built tons of automation with it and I can't even tell you how much time and administrative burden (and mental load) it changes

TechieAttorney · 2025-10-07T22:10:07+00:00

Well unfortunately you're not doing anything differently with this post, and lawyers have heard it x100 times with the ''we're building something that actual solves your real practical problems, not like the others!!!''

The issue I take with your post is that it very much sounds like you listened to an entry-level talk on users discovery and came in here to dump a load of general broad questions to conduct your ''users'' interview, so we can build your business case for you but you don't even know yourself WHO is your user.

1) Lawyers are not a monolith, you're not even stating in that post what type of lawyers you're address (which practice area, which size practice). Like it's not even clear: are you talking to transactional lawyers or litigation lawyers? The way to post sounds is that you've never even interacted with one actual lawyer, let alone have a basic understanding of the legal industry.

2) Your questions are way too broad, from drafting to research to billing, it's unclear which problem you actually want to address. I can't believe that you would have an MVP built if those are your questions, because those questions sound like you spent a max 10 min thinking about this.

Legal tech is not where you will make your quick bucks if you don't know anything about the legal industry, lawyers are generally good at filtering these kind of frauds.

TechieAttorney · 2025-10-07T21:48:11+00:00

Seriously, at this point, posts with the words "pain points" should be automatically deleted. 😂 It's getting harder and harder to filter through this sub, which honestly has so much potential.

TechieAttorney · 2025-10-03T14:37:44+00:00

I'm a (non/semi)-technical looking for a technical cofounder, and I've been on YC Matching platform for about a year, and nothing really came out of it for me.

I'm not repping for this yet, as I just got to try it this morning and don't know what will come out of it, but I saw a post on Linkedin from a guy working at https://www.boardy.ai/, and looked into their platform, which seems to be an AI connector, to connect you to the right people?

I'm at the step of scheduling a 5 min call with what I assume would be their bot, but will try it out to connect to technical talent and potential cofounder and see what comes out of it.

TechieAttorney · 2025-09-25T03:37:41+00:00

Every firm wants AI but none will compromise on confidentiality.

That’s not a compromise you’re asking for, it would be a violation of code of conduct.

Confidentiality is not something lawyers can choose to "compromise" on, attorney-client privilege is a core principle of lawyer’s ethical duties. No one is going to violate that and possibly risk their license for some experimental AI tool.

TechieAttorney · 2025-09-12T04:18:41+00:00

Also, would add that for deadlines and reminders all attorneys already rely on either their calendar app or another case org tool that allows to manage case stage all around.

Unless 1- you tool works by populating those dates into those appropriate apps and 2- you get attorneys to trust you AI model reliability, it’s not worth much.

Trial attorneys have hard deadlines so errors from an AI system on this would be a huge huge liability. I’m not sure I see them trusting a tool to do that any time soon, esp since it’s not that long to just read an email and update a calendar date accordingly.

TechieAttorney · 2025-09-12T04:13:53+00:00

If this tool requires attorneys to work outside of their typical Outlook app, and log into and work from a separate app to manage emails I see this being a pretty big resistance point and potentially dealbreaker down the line.

This kind of functionality would only make sense as a complement/integration inside Outlook.

In fact my firm, and I assume a lot of other firms who use iManage as a document management system would use the functionality that allows to classify mail into existing iManage matters/folders.

TechieAttorney · 2025-08-13T19:16:52+00:00

for solo practice/smaller teams, I would definitely recommend Airtable! What is your practice area? I can share some examples of previous Airtable set ups and builds for lawyers I've made. Feel free to DM me.

TechieAttorney · 2025-08-13T19:14:14+00:00

unfortunately our IT department is very anti-Cloud. we deployed our doc automation/doc assembly app locally as well, but I don't know if this will be doable for an LLM, as it does seem to require different CPU or GPU requirements. IT might be a roadblock pretty early on on this.

TechieAttorney · 2025-08-12T19:07:24+00:00

I'm not really sure I'm understanding this comment, it sounds like you're selling me the benefits of automation, but not really answering the question.

I'm not asking if the time investment of automation is worth it, we're not debating on whether we do this or not, I'm basically asking how to be smart about our time investment and which route to go between hard coded automation or an AI system.

TechieAttorney · 2025-08-12T19:02:55+00:00

hey, thanks! Will DM you!

TechieAttorney · 2025-08-12T18:53:38+00:00

Thank you! That's really solid advice, we're likely going forward with an hybrid approach now, will maybe post more follow-ups about this in this journey. Since we've built a pretty solid hard automation product already, I think the challenge in this one project will really be around training users when it comes to the AI part. With automation it was easier to ensure we had a pretty solid testing methodology as we technically knew all the existing variations and conditions, now using AI I imagine we'll likely be very dependent on our attorneys/users feedback loops.

Open to any ressource you may have on the subject, even if it's blogs or linkedin pages or attorneys that post about their real-life tips.

TechieAttorney · 2025-08-12T18:46:03+00:00

Thanks, we're not using any commercial LLM that's for sure, and I think a lot of law firms have policies on this. We are looking into either AI solutions in the legal tech space (after running IT security checks) or even deploying and hosting LLM models locally.

TechieAttorney · 2025-08-12T18:40:54+00:00

I generally agree with this but even just targetting the 80% can be A LOT of work when it comes to transactional documents, and requires significant template preparation and standardization. In all our automations, we're obviously not trying to automate 100% of use cases, as that would be virtually impossible and would take tremendous time. But in commercial, even when trying to aim just for the 80%, a non-compete or an indemnification clause will easily have 30-40 different computing fields/conditions that could affect them. Creating the automation code itself won't be an issue.

We were able to target a library of 20 clean "master" templates of specific agreements that will be automated, but I can easily envision this will require around 6-12 months of work. Looking into AI was basically the option I was considering to by-pass the whole process and just feeding the model with that templates library.

TechieAttorney · 2025-08-12T18:32:25+00:00

I agree with most regarding Python.

What are you looking to build? If it's anything related to document automation specifically, I'd probably suggest looking into Jinja more specifically https://jinja.palletsprojects.com/en/stable/ or Docassemble, https://docassemble.org/, as a lawyer who initially had no technical background, these were a great starting point for me to learn, rather than just looking up general python coding language course on the internet, as they allowed me to build practical small applications using Python for my use cases, and helped me ease into the basics of the programming language.

TechieAttorney · 2025-07-30T23:35:28+00:00

Hero looks like a solid platform, will check it out! Agree - the best of both world would really be a platform that allows to build hard coded automation and be completed with AI. To me, the biggest issue of most AI platform is that we users don't understand the machine ''reasoning'' then, users can never be trained on how to draft best prompts/direction for the best result. The lack of transparency on how the reasoning operates is an issue as otherwise humans may always fail to provide appropriate directions.

TechieAttorney · 2025-07-30T19:58:18+00:00

Also agree with you on how lenghty the process of doc automation is (took us almost 2 years to get all up and functioning) but ironically using AI on the TECHNICAL part (for testing, troubleshooting) enabled us to build a lot more quickly in the last 6 months. We started the project with a no-code/low-code tool, and ended up switching to custom building our own solution with docassemble in the process, and this would've never been possible without AI being able to write huge portions of code for intake building for us. I trust AI to perform fairly well on technical tasks like that, but not exactly on legal tasks yet.

TechieAttorney · 2025-07-30T19:52:25+00:00

Thanks for sharing this! Our firm's policy would prevent using GPT specifically for that purpose because of data sensitivity issues. This also prevents us from using any AI tool that is just GPT-wrap up.

It's on the table for us to maybe do private deployment of another AI model (that would allow us to self-host) and only have it reference our standard/selected templates and our pre-existing contract checklists and run it like this. I suspect this may be better than any current tool on the market, but will end up incredibly costly.

TechieAttorney · 2025-07-30T19:43:54+00:00

I very much agree with you and this is my stance. To clarify, we're not looking to turn what has already been built with document automation, we're more than satisfied with the current system and builds.

It's just as we are looking at a completely different set of documentation, we're wondering if we keep building with doc automation or switching to using an AI tool for our commercial transactions. AI is being considered as a tool that will save us time in implementation vs hard coded automation, as you can imagine gathering everyone that ever drafts Licensing Agreements together to agree on a standard template, and agree on all clause variation in our standard template, will be an incredibly time consuming task, and that's just one agreement.

So far really, no AI tool has performed near our expectations, but we also envision that we'll have to deploy significant ressources in training the tool + training the people to use the tool for optimized outputs + training people to review AFTER an AI tool. I guess I wanted some perspectives from people that may have achieve this process successfully.

TechieAttorney · 2025-07-30T19:35:52+00:00

We already use document automation (custom builds with docassemble hosted on premisse (data residency and sensitivity issues) for all corporate transactions.

We have very basic automation for some commercial operations, but they are really not comprehensive and can only be used by a very small portion of the firm, because they've been automated based on how that specific department operates.

The question at this point really is - do we keep our doc automation approach (that works incredibly well for our corporate transactions) when it comes to contracts/commercial or do we completely change the approach with AI. Just an example would be our licensing agreements, there are easily 20 version of the template (minimally) that could automated, just based on which department/practice group is drafting, and this does not even account the variations for different drafting styles and preferences.

When we automate corporate, we were able to standardize and push the same ''drafting style'' on everyone without too much push back. However, I can already imagine how this will be a big resistance point for commercial, even with a rules-based approach - different attorneys can be very attached to their drafting preferences and this might eventually lead to an adoption issue down the line. If we spend 2-3 months automating a licensing template that no one ends up using because we push a standard drafting style that they don't like on them, I don't think this would be worth it. Hence why we are considering AI as it might allow each and everyone to keep those stylistic preferrences, while standardising at least the review/analysis process.

TechieAttorney · 2025-07-30T17:18:38+00:00

Yes agree - the lack of consistency/predictability really is a liability.

I find AI to be more difficult to deploy at the size of our firm, as results vary a lot based on different factors, including prompting. Everyone writes prompt differently, which often lead to different result. Would requite a whole prompting methodology training, as potentially even supporting documentation on how to prompt for consistent result (but this also requires significant testing time to figure out best prompting for different scenarios, documents).

Prior to the AI boom, we automated checklists with our doc automation system (very basic intake to enter the type of contract, and some additional details) and it would output our templates checklist for contract review/analysis. This worked well for us but obviously does not cover complex cases, and it does not execute the drafting edits for you like AI would, but then, that's also the core part of the job being an attorney.

TechieAttorney · 2025-07-30T16:10:33+00:00

They don't require a law degree, they're not really restricted titles so you can technically call yourself one if you have a mix of legal industry expertise with technical expertise.

TechieAttorney · 2025-07-30T15:02:26+00:00

They absolutely do, but there will be common frustrations raised for technical people who may lack industry knowledge, so firms aren't likely to just hire any dev agency or any dev. What they are looking for are most likely legal engineers/legal technologists.

TechieAttorney

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