How it Began
Picture yourself sitting in an open-air margarita bar overlooking the Caribbean, people dancing to 80s music below, and a wonderful breeze that takes the sting out of the tropical heat. Now, imagine a Mary Tyler Moore Show type winter in Chicago, Illinois—months of grey overcast, and entirely too many people honking their horns for no good reason. What would make anyone leave the symphony of the former for the cacophony of the latter?
The direct answer is that AI, or its advent anyway, dislodged me from paradise to come to the tech scene in Chicago to start a legal tech company. Reflecting on it now, one could attribute the decision to the fateful choice to go to law school. But for that decision, there would have been no estate planning, no solo practice, and you can’t create a software solution unless you have deep insight into a problem you want to solve.
If you wanted to take a broad view of the thing, it really began with Master Sergeant Klumper. If Master Sergeant Klumper hadn’t taught a particular lesson at Fort Benning, Georgia, at the Infantry Officer Basic Course, I may not have listened to him instill in the young lieutenants of class 9-90 that every battle leader should learn the job of every soldier in his platoon. You wouldn’t be reading this today. I applied this Army leadership technique to my small law firm and dedicated a Saturday morning to learning the job of every paralegal in my firm. At my conference room table, I waded through open and closed files, following the paths we had taken. As I worked through the workflows, I noticed predictable inefficiencies. Then, some redundancies. And then… O… M… G…! Were we really entering the same client data into SEVEN software applications? (Yes, I actually asked that. Out loud.)
The Mission Transformed into a vision
It was on that day that a simple mission evolved into a vision. Practicing law is hard enough without iterating over the same data entry tasks seven times. With so many software applications, it was nearly impossible to build one workflow. No, I daresay, I will not suffer this any longer! On that day, I swore to create one application that did it all. At first, I just wanted to love practicing law more. Over time, this gave way to an envisioned future. A true vision to not only help my clients but inspire them. To generate quality work products so quickly and effortlessly that there was ample time and desire to spend more time talking with my clients. Advising them. Learning what was really going on in their families.
Relentlessly, I worked the problem. I would build an automation, and let a paralegal go. I kept building and building until I reached the point that I had just one part-time assistant left. While it is sad that four paralegals had to find work elsewhere, I eventually reduced my overhead from $50,000 per month to less than $2,000 per month. I enjoyed a new freedom I had never felt and never regretted.
I have never spoken of this. Candidly, I am not that impressed with this accomplishment. My app could generate complex legal documents quickly. I did spend a lot more time with my clients. I am proud that I was able to reduce my fees. However, the leap from efficiency to inspiration eluded me because no technology existed capable of implementing the legal plan, in some cases, decades later, and at the hands of younger family members who rarely knew the plan existed, let alone how to execute it.
I left the Caribbean to build a software application that converts transactional practices into advisory partners with families generationally with technology that can listen for life events and take immediate action according to the legal plan. This will iterate generationally. Imagine a trust agreement, once dumb sheets of paper, as software and Trust Advisor provisions iterating over trust corpus performance monthly because the technological revolution that is upon us, for the first time, is capable of bringing us all to inspiration.
Is it Possible to Inspire?
I entitled this post, “Is this the end of legal software?” I hope so. We have an opportunity to take back legal tech and build it to do important work by partnering with AI. This may surprise you, but I am of the opinion that AI should not draft legal documents. However, AI is a great paralegal, programmer, and marketer. Imagine such a paralegal, an amalgam of the best employees with whom you ever worked but never slept, never took or even asked for time off, and could perform limitless numbers of tasks at the same time. In just one small example, AI can access data with a new type of database called a vector database that does not require complicated queries from bloated databases. Even when an AI agent must access data from a SQL database, AI can easily convert your early morning question to the complicated query dashboards need. That’s right, just like a text-to-speech prompt, AI can use a text-to-SQL query prompt.
Soon, the days of the click, click, click parade to answer a simple question will be replaced by a calm and soothing voice. “Good morning. I drafted the Jones probate petition last night because I scraped public notices and, sadly, Bob Jones died two days ago. I sent the pleadings for your client’s signature. When they return, you can simply authorize me to file the petition with the probate court. We are set up to pay the $40 ex parte fee so the court clerk can walk the file to the commissioner for her signature on the Order Appointing. Also, the Cubs beat the Brewers in overtime last night in a thriller 4-3 sealed by a beautiful home run by Beltran.”
