My unique solo practice

TLDR - I split time practicing and coding and have been building a client-facing app that my clients use to build case files and apply for representation. It’s super tricky and uses AI to do cool stuff. I’m gearing up to scale it up.

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I want to share a bit about my somewhat unconventional career path and the solo law practice I’ve been developing for the past ten years—one that I hope to change dramatically in the next five years. To give you a sense how unconventional: Friday I had a nearly day-long settlement conference with a federal magistrate judge and Saturday I was coding furiously, trying to finish and push out a new feature in my custom case management system/website. Let me explain.

I opened my employee-side solo practice in 2014 with just enough clients to stay afloat. Over the years, I’ve balanced contingent-fee and hourly-fee cases that have kept me in court/arbitrations/agency matters regularly, led to consistent settlements, and provided a steady stream of hourly work. Meanwhile, I’ve pursued my long-term goal of building an AI-based law firm. Currently, I have one non-attorney staff member who’s been with me since 2016.

Discovering the Power of Coding

My stepfather taught me how to code in elementary school, and I’ve been the “tech person” in social and professional circles ever since. I've spoken at national and regional conferences on using technology in discovery and trial. When I started my practice, I began coding tools for it. Early on, I decided: if I’m going to do a task more than once, I should automate it. An the focus of my automation was to allow folks who thought they had employment claims build case files that allowed me to understand their cases better, before I accepted the case.

Building an Automated System

By 2018, after a rare and exciting week-long jury trial, I found myself juggling various tools—Zapier, Mailchimp, Google Sheets, Formstack, plus more and more custom code. I used Zapier to tie this system together, and it funneled all new prospects toward a contract, then helped them build a fairly comprehensive case file including a timeline, documents, witnesses, and damages. Although it worked, it was clunky. Clients got a lot (hundreds) of Mailchimp emails linking to forms; once they submitted those forms, automation triggered updates in Google Drive and generated and updated a custom timeline. Despite all the moving parts, it managed to get the job done. But it was my particular client-base--mostly broke folks who had lost their job an believed themselves wronged, looking for contingent-fee representation--that allowed me to put them through this and find some good cases.

Realizing the Potential for an AI-Based Practice

After setting up this system, I saw that the possibilities were bigger than I’d imagined. I realized I could move legal decision-making from human-only tasks to an iterative, software-based model—doing things like calculating statutes of limitations, generating complaints, and more. Then, when GPT-3 was announced, I applied for and received beta access and began experimenting with using the data my clients were building into case files to generate automated prompts to better use my data. Early on, I filed documents in court that AI helped me draft—always with human review and supervision (It never occurred to me to file a pleading without double-checking it and I noticed that LLMs made up cases very early on). Still, the promise was clear.

The Birth of Cloud Counsel

By the end of 2018, it was obvious I needed much more professional, clean tool to find and build cases. My patchwork system was groundbreaking for me, but also prone to constant failures and unwieldy. I did research on how to build an actual web app, joined Fireship.io to improve my coding skills, and started building an Angular + Firebase application to house my ideas in a single, polished app. My goal: give clients an attractive, user-friendly platform to build their case files, automate legal tasks, and improve over time by iterating and learning from user feedback.

Building in the Dark While Patching the Old System and Practicing

For years, I would draft pleadings, take depositions, and argue motions in the day and stay up late at night coding, coding, coding my app. It went from a blank white page to being a simple portal I could sign in and out of, to having multiple user classes and modules, to being a full-fledged app with all the bells an whistles we have come to expect of web apps that deliver services. By January of 2024, I was ready to replace my website.

Trials, Tribulations, and Growth

In January of last year, I switched my main website from an old WordPress site to my new app at jmadisonplc.com. I shut down all my old email marketing, which no longer accurately described my services. And I started trying to make it work with the new app. New business dried up, and I discovered bugs I didn’t know existed. I’d been itching to launch because I was tired of patching the old system, and I felt ready to deal with the disruption in my practice. Then, by April, an intake process (nowhere as developed as the one it replaced) was operational again, but I had to juggle active cases, so development slowed. I also considered hiring a development studio to take over, but opted to keep going on my own for the time being. Little by little, I’ve dramatically improved the app’s features, usability, and polish. I am about to release a major update that, in addition to allowing the users to build a timeline of their case with documents and witnesses, the app will allow us to track and manage claims, defenses, and proceedings. I am so very excited about the direction of the app.

Scaling Up and Looking Ahead

From the start, I’ve built Cloud Counsel to scale. I chose the architecture I did because of the ease it will offer me in scaling. It can accommodate 10, 100, 1,000, 10,000, or more users. But, of course, I cannot handle that many users. When it makes sense, and in the amounts and pacing that make sense, I plan to once again begin paid online marketing. I believe I can sell a unique service. Ideally, as the AI and automation features I build expand, human representation may be needed less often to resolve my clients' and prospective clients' concerns. But when a client needs a lawyer, they’ll already have a robust case file, and we’ll have identified their claims.

The most exciting prospect is mining contingent-fee cases from a much larger pool of applications. I have, for a long time, contracted with my prospective clients so we treat the case file they build in our system as an application for representation. They apply for representation by signing the agreement and then building, for however long it takes them, their case file, which we review looking for good claims. And as the app automates more of the case-building process, I expect it to help settle far more cases and streamline litigation.

If I’d built a similar web app for a corporation, I probably could have secured backing from a venture firm by now. Since getting into this space I've met a few founders and had a couple peaks behind hoods. I'm persuaded that what I've built is unique, innovative, and probably has some architectural advantages over other tools that may try to get to the same place I'm going. And I've come to firmly believe that law firms must deliver their services through apps they build and maintain themselves—not through third-party vendors alone. It’s clearer to me than ever that law firms will need to be tech companies in a future dominated by technology. Our core services will be made and delivered by tech platforms like mine, I am persuaded, and that means that we, the lawyers, need to build and maintain them, not non-attorneys or firms that are not operating as law firms.

I still use vendors: Clio is great for my trust accounting and I'm not even building, yet, a replacement for that. But eventually I want my firm to own and continually iterate on the entire tech stack.

Future Plans: Staffing and Marketing

In 2025, I plan to bring on more talent. I am thinking that, at some point soon, I should hire a 4th or 5th-year attorney to start taking some of the cases that Cloud Counsel generates. I have very little experience in hiring and employing folks and a lot of experience in capitalizing on employers' employment failures, so this isn't a business move I feel especially confident with, on my own. In an ideal world someone else does the hiring, lol, but I guess I'd have to hire them. I’m also looking at adding a developer to focus solely on the app and paralegal staff to support the legal team. I imagine the firm growing to have enough attorneys to market and accept clients from all states. We should also have and maintain a development team to fully take advantage of the opportunity to advance our tools quickly. I am looking forward to Cloud Counsel one day housing tens of thousands of current applicants for contingent-fee representation, all of whom getting AI-based assistance within the app, with many lawyers or paralegals scouring the db to find the next case and help resolve it.

I stopped marketing around 2020, when my intake got too busy for me to handle. But I’ve run successful AdWords campaigns in the past, and I’m prepared to restart them once my intake funnel is back where it was. For now, I’m still spending $0 on marketing and getting a trickle of conflict checks through my web presence and referrals. I want to be sure the new system can handle high volume before opening the floodgates. I also have yet to replace the blog I lost when I switched from Wordpress, and blogging is part of my organic search strategy too. Eventually, I’d also like someone other than me to manage communications across all channels.

Sharing My Vision with Other Attorneys

I have considered offering my app to colleagues in the employee-side bar through a “Co-Counsel Module.” Prospective clients seeking contingent-fee representation can agree to share their case file with outside firms who might be interested in representing them. Co-counsel users could see a table of anonymized cases, request permission for a conflict check, then get full access if approved by the client. If the case is a good fit, they can extend representation terms, work the matter using our tools, and share fees with us in the end. But work on that module, which I initially built but haven't fleshed out, is on the back burner while other features get my attention.

This has been my dream for over a decade, though it’s evolved along the way. Thank you for letting me share it. I’d love any feedback. I know this path isn’t for everyone, but I’ve found immense satisfaction in it and am more excited about the future than ever.