Breaking Free: A Law Firm Owner's Journey from Traditional Practice to Tech Revolution
Estate planning has always been about ensuring that clients’ wishes stand the test of time. But as family structures become more complex and assets increasingly digital, the old ways are not enough.
BONUS AUDIO: How I am creating a voice agent who knows what I know about estate planning to answer my firm’s phones, make outbound calls, and answer questions on the BoomX Show: Laws of Money
Five years ago to the day, I was there. Again. At 7:42 AM. I vividly remember sitting at my desk staring at a wall covered in sticky notes mapping out inheritance flows across three generations of a complex family trust. Twelve hours later, I was still there. After twenty-five years of this, I had a startling, life altering realization: this sucks.
The Birth of an Idea
Its one thing to realize that something has gotta change but quite another to do anything about it. I, like most lawyers, was glued to the concept of stare decisis, the creed of lawyers for centuries, i.e, “upon bad decisions made in the past, we stand!” I badly knew I had to have another epiphany. Dear Lord, give me another ah-hah moment similar to the “this sucks moment” you sent yesterday!
The epiphany came later...during a particularly challenging case involving a blended family - lopsided net worth, noticeable age difference between spouses and one has been diagnosed with dementia. Seventy percent of Americans do not have so much as a simple will let alone a legitimate asset protection trust. A diagnosis of dementia usually does not change that statistic unless someone ... anyone ... did the math. Yes, legal planning is far more number-based than most realize. In every advanced care case, it is a simple equation that answer a horrible question. It goes like this: monthly income minus expenses where net worth is greater than zero expressed as assets/expenses - income = how long until dad goes broke.
Over and over, I iterated on that problem within the limitations that centuries of estate and trust law had imposed. If not difficult enough, the task was worsened by the available tools with which I had to work, stone and chisel technology in the form of static documents, i.e., “scenario” driven templates. The former, legal tradition, was linked to the latter, tech aversion.
Lawyers have paid a high price for its resistance to technology. The price is so high that estate planning lawyers have struggled to pay it, explaining the long hours and high stress. This is embarrassing especially due to the fact that our younger brother, Charles Schwab, has rocked it. Chuck is not hampered by arcane rules of professional conduct, frustration that the “word processor” ever replaced the typewriter, and a mistaken belief that it is not a competitive landscape. This explains why Chuck plays gold on Friday, is always tan from the cruises he and his third wife takes, partially expensed, and has another Audi in his garage.
I love Chuck and wish him well, but even he gets it. The last time I chatted about this with him during the Holidays, he agreed that, in part, fear of technology had caused a tragic gap. No, it is not just a “gap”, it is a crisis, and one that is easily demonstrated. If you have ever considered legal planning in the context of the most litigious culture in history, a societal mindset that pumps out new laws annually by the millions, then you likely have gone to Mr. Google for legal advice. Recently, I experimented with search and input “what is a spousal lifetime access trust?” I was appalled. There it was. Blatant and shameful. The number one, page one organic hit, the site Google considers to be the most reliable expert to answer my question, was a bank that has paid the largest fine in American history for fraud - Wells Fargo. The usual suspects were stacked up behind it: Investopedia, Nerd Wallet, and the Big Three: Schwab, Fidelity, and Vanguard. Navigate to any of those sites and you will see the public facing high country of forward facing tech, the Nirvana that comes to those who keep up with the market.
America is Wealthy; Americans are not
The category of this substack is Technology. The secondary category is finance. Law is not listed for reasons that are likely clear by now. It is my contention that any sector that ignores the technological revolution that is upon us will do so at its peril. Further, some sectors are too heavily weighted to fail without exacting a societal harm. This is already playing out. Seventy percent of Americans don’t have a stinking will. There are 50,000 planning attorneys in the United States. Financial professionals are unleashing a digital storm and it will get worse. At the same time, Americans are going broke on high unreimbursed care costs, unnecessary taxation, and financial mismanagement. This is proven by a hard, cold statistic. If you have a net worth of just $1.7 million, you are in the top 5% of wealth owners in America today.
In this environment, lawyers have involuntarily abdicated the conversation. The result? Couples across America think a revocable living trust protects their assets while Medicaid, judgment holders, and the IRS correctly disregard its existence.
This is where my journey as a legal tech founder began, at the intersection of centuries-old estate law, market conditions, and cutting-edge artificial intelligence.
The Algorithm: Where Traditional Law Meets Modern Technology
I am happy to report, I solved this problem for my law firm. I did what no lawyer has done before, at least none that I know personally. I began to invest into technology. There was none to buy, so I built it. The rewards came quickly. For the last three years, I have practiced with no support staff. None. My clients complete an easy-to-use online form and, upon submit, a proprietary legal algorithm, identifies the planning profile, one of nine, that best describes the client, her family, and money model. Best of all, within moments the legal plan is drafted. Revisions are just as easy. IN fact, the protal I bulding now will allow you to call an AI agent who will pick the phone and make non-substnative revisions right there and then. Nonsubstantive refers to the only mistakes that exist in my work product, misspelled names that the client entered back in step one of the process. Oh! Sometimes the mistake is the date of marriage, but that happens only when it is the husband who completed the form.See how that worked? Hire me and you will experience it. You do the data entry, you instantly receive your documents, and I sit on a beach in the Caribbean. All of that is true with one clarification. Technology helped me. Saved me. I went from a monthly overhead of $50,000 per month to one of about $750 per month now. This allowed me to live about 250 yards from the Caribbean in Puerto Rico. Two years ago, I decided to bring this to other estate planning attorneys. I am now freezing my law books off in Chicago to launch my legal tech startup.
Next Step: Convert Legal Documents to Software
While technology that helps all lawyers, not just the big law firms, is pretty cool. The us versus them aspect of this benefit aside, reducing the time and expense of creating legal plans benefits all of us. Lawyers need to spend more time with their clients.
That is not the exciting part. The exciting part is the next phase. I am working on converting trust agreements, powers of attorney, and even a last will and testament into software to become the command center for your family wealth bunker. More on that next time.
About the Author: This post is written by a practicing estate planning attorney and legal tech founder, bridging the gap between traditional law practice and cutting-edge technology. Follow for weekly insights on the intersection of AI, law, and legacy planning.