23 Years Ago I Made a Bet
A market bet. An architecture bet. A platform bet. A core foundational bet. It was risky. On paper, it looked like a mistake. Now that we’re here, it feels prescient.
But you probably don’t care about my bet. Not yet. So let’s talk about yours. You look up billing software and the first thing it does is ask you to “book a demo.” The price is higher than the last time you checked, and if you’re already pulled in, your renewal went up, the interface and features you relied on changed, and nobody asked you first. Support is a ticket number now, answered by a stranger juggling forty other firms who couldn’t name one feature of the thing you pay for every single month. Somewhere in fine print you never read, you handed your clients’ data to people you will never meet. Don’t dare stop paying. Or all your data is locked. Just like that. And you feel it. That tight pressure of being squeezed. But it wasn’t always like this.
My bet probably seemed strange from the outside. Betting on Apple? On lawyers using Macs? Apple wasn’t for business. Windows was where you got “serious” work done. But I ignored all the other companies (Timeslips, et al) abandoning the Mac. This was, after all, before iPad. Before iPhone. Hell, the iPod and iTunes were brand new. Steve was still selling people on the digital hub. Burning home DVDs was novel (and iDVD was, famously, dead simple. Despite multiple engineers entering the design briefing with folders filled with UI sketches and design mockups, Steve walked up to the whiteboard, drew a rectangle with the word “Burn” inside, and said, “This. This is the whole UI.” And the engineers weren’t even mad. They all immediately knew he was right).
As we all know, things changed. The iPod was a smash hit. And then came the iPhone. And the world changed. I still remember watching the keynote. 3 things. A breakthrough internet communicator, an iPod, and a phone. But not 3 things. “Are you getting it?” Masterclass.
Meanwhile, the web grew up. We got The Cloud. And not long behind, the SaaS business model. Soon every app wanted to charge you a monthly fee.
23 years ago, subscription pricing for something you used on your computer seemed absurd. And then came the justification. “Server costs.” Sure, made sense. But now, prices have skyrocketed while server costs are literal fractions of a penny per request.
Pull up your last bill from a service you subscribe to. Go ahead, I’ll wait. Now sit with this: serving you for a month costs them pennies on the dollar. If that. That gap, between what you pay and what it actually costs them, isn’t “server costs.” It’s the markup. It’s your money, flowing straight up to the firm that bought the company you used to trust. Is it going to developer costs? Sure. Support costs? Yeah, okay. But guess what? The split of that money dramatically changed when that company was bought. The real driver of price hikes isn’t “we made the product better,” or “we hired more support staff.” It’s we cut costs, outsourced the support, and our investors need a bigger yacht. So keep paying, and don’t ask questions.
The Mainframe
50 years ago, Apple was in a similar situation. They had an idea. A computer you owned. At the time, only people who rented time on a mainframe had access. IBM was king. And it was expensive to hang out with the king. But Apple thought different. They birthed the home computer revolution. And yet, here we are. We’ve come full circle. From the revolution of the home computer, to the explosion of the internet, to the shrinking of computers that now fit into your pocket. We’re back to renting time on a mainframe.
What the hell happened?
Private equity swooped in. Venture capitalists killed value to squeeze profit. Because a business model where the customer pays every month? For access, not ownership? That’s the ultimate capitalist dream. And I watched it happen, like a car crash, in slow motion. And I steered clear of it.
And the costs just keep climbing. Cost of doing business, cost of living, exorbitant price hikes from corporations run by bean counters with no product vision. It’s all taken its toll. And the irony is real. Things don’t just get more expensive. They get shittier. Outsource the customer support. Use cheaper materials. Build faster. Eliminate costs. Make the product worse and charge the customer more.
Well, I don’t know about you, but I’m utterly sick of it. And that’s why TimeNet Law still exists. It’s why I do what I do. Because here’s something different. Something refreshing. Something that has been fundamentally unchanged and quietly built up since a time when the internet was novel, and software was fun.
Against the Tide
Just as I believed in the vision of the Apple II then (owning your own home computer, buying and owning your tools), I still believe in it now. And the other side of the coin is even more insidious. It’s not just renting instead of owning. It’s being given the privilege to share all of your data with third parties, be surveilled, give up all of your usage statistics via telemetry, and increasingly, train AI models that you’ll never use or see.
10 years ago, not moving to Cloud was ludicrous. I resisted. 5 years ago, not requiring a subscription for professional business software was insane. Again, I stood firm. Because I believe in the vision. Privacy and security. Ownership. Quality tools that don’t get ripped from your hands, or silently changed, or spy on you, without your knowledge or consent.
Every one of those decisions, a hard no, a difficult choice, a line in the sand against a tide pushing the other direction. And now, finally, in 2026, it pays off. Because people care about privacy. Lawyers care about privilege. People are concerned about surveillance. The simple concept that if the product is free or cheap, then YOU are the product finally resonates. And the you-will-own-nothing-and-be-happy corporations continue to push the envelope on what the market will accept. Subscription fatigue is real.
The AI Revolution
If subscription fatigue is real, don’t even get me started on AI fatigue. I know, believe me. It dominates the tech news cycle. It’s all I write about in The Sunday Brief. And you probably fall into one of two camps. You love AI, already use it, and fully believe it is the way of the future. Or, you hate it. Resist it. And want nothing to do with it. Well, let me tell you. Both sides are right.
More than ever, the rise of AI is cranking the volume on the privacy and surveillance discussion. It’s siphoning entry-level jobs from college graduates. Data centers are causing untold damage and misery to residents unlucky enough to live near them. And it’s accelerating at an exponential rate.
AI is dangerous. And not just because it’s changing the world, at speeds and in ways that are difficult to comprehend. But also because of its failure modes. And for attorneys, in particular, those failure modes are landmines. But I’m here to tell you, it’s not going away. And the people who don’t use it will fall behind. So, let’s talk about it.
AI is an existential threat for attorneys on three levels. First, it will hallucinate. Given a large body of context and a poorly scoped prompt, it invents what it thinks you want. If you aren’t extremely careful, you will get the same confidently wrong answers that have fooled many attorneys. For a profession whose primary job is due diligence, this is the killer.
Second, it will continue to take work away from junior associates and clerks. This isn’t so much a problem today, but it creates a serious issue for the future: where will new senior attorneys come from, if juniors aren’t getting the experience and training they need to progress? On top of that, AI is (wrongly) teaching the general public that they don’t even need an attorney. ChatGPT can help them win the case on their own. And guess what perpetuates that myth? Every lawyer using AI irresponsibly, and getting sanctioned for trusting inaccurate AI. The public doesn’t understand the nuance. They just see “Attorney busted using AI in court” and think to themselves, “If the lawyers are using AI, why can’t I just do it myself?” This goes far beyond a sanctions or license problem. It threatens the entire legal profession as a whole.
And third, and this is the one that can really bite you in the ass: the privacy problem. Because unless you’re BigLaw paying big prices for truly locked down AI systems, every word you type into an AI chat can and will be used to train the model. Your client’s privileged information, your proprietary body of legal work, your case strategies and questions, all feeding a model, likely through or eventually to a data broker, and even fed to your opposing counsel’s direct discovery process. This isn’t hypothetical. A federal judge has already ruled exactly that (United States v. Heppner, Judge Rakoff, SDNY, ruled February 10, 2026).
And we haven’t even gotten to the cost. AI is subsidized. It’s a giant bubble, and it will burst. You’ll pay hundreds of dollars a month for a “legal AI service”, and potentially be charged for going over on tokens on top of that, and the price is going to explode. It’s not if, but when. You’ll build your entire workflow around a $200/month subscription, and then one day they’ll raise the price on you 10x for the same (or even less) usage. I know, because it happened to me.
Not All Doom and Gloom
AI is also incredibly useful. It can solve complex problems, make you more productive, help you manage difficult situations, and on a larger scale, it has the potential to solve many of the biggest problems facing humanity.
And let’s be real. You need to start using it.
So how do you get started? How do you mitigate all of these failure modes? By owning your own premium, custom-built, private, offline local AI system. The computer on your desk is its own mini data center. You already own it. Use it.
So, how hard is that to build? Very. Fighting hallucinations is endless. Tokenizing massive context blobs into manageable chunks of data is like taming a lion. Comparing models, keeping track of the latest releases, knowing which ones are more prone to the exact issues you, as an attorney, cannot afford to risk. And engineering the perfect prompt is more an exercise in voodoo and luck than a science. How do I know? Because I built one. And it’s good. Damn good.
Oasis. An Ocean Between You and Them.
I call it Oasis. Offline AI. Private. Fast. Powerful. And you need it. Because it solves all of these failure modes. And on day one, it will tell you things about your law practice that you don’t know. That you need to know. And it will help you stay competitive with all the other firms who are implementing (recklessly or not) their own AI workflows.
How will you navigate the next ten years, when the billable hour dies, the pool of available junior associates dries up, and AI is helping firms get work done 2, 3, 4, 5x as fast (and it does)? By implementing your own moat. Private. Offline. Anchored in truth by your own data. That never leaves your Mac. A trusted group of advisors watching over your firm, helping you survive the rough transition ahead.
You need to be briefed on things as they happen. You need to productize your law firm. And for that, you must know your effective billable rate, your repeatable work patterns, and the market value of the work you’re performing. Because when you can offer a client a $10,000 package for exactly what they want, that ends up paying you an effective rate double what you usually charge, and still saves that client money? They’ll never leave your side. And if you don’t, another lawyer is about to.
You need automation to manage daily mundane tasks. Building a new matter from a long, rambling email. Chasing down collections on overdue clients. Not just running reports to see the numbers, but understanding the numbers. Knowing when important metrics are improving or declining before the net effect causes an all-hands-on-deck meeting.
Because my vision is the same as it always was. Own your tools, protect your privacy, and be ready to hold the line in the David vs. Goliath fight that is unfolding right now. BigLaw, private equity, AI-driven workforces, and a fundamental misunderstanding of what AI is, how it works, what it can, and most importantly, what it can’t do are all conspiring against solo and small firms. But here’s the secret: you’re the backbone of the legal profession. And more and more, clients want a real relationship with a real person who really cares. Because, well we already talked about the nameless, faceless corporation squeezing you. How it feels to be a cog in their machine. You don’t want that, and neither do your clients.
I spent a long time resisting AI, and then thinking about how AI could be used responsibly in TimeNet Law. I wrestled with the simple fact that AI is here, it’s growing, and it’s the future. But what would an AI in TimeNet Law even look like? Document summaries? Sure. Analysis? Yes. Drafting documents? Of course. But then I thought bigger.
Something Different
TimeNet Law has routinely been at the head of the game when it comes to features and design. I innovate, they copy. I have receipts, but that’s not important right now. What is important is that you need AI. And if you don’t get it from me, you’ll get it somewhere else. And my standard of excellence, TimeNet Law’s promise of a simple, powerful, reliable, premium experience, demands an AI system to match.
So I built you one. And yes, it can do the things other legal AI systems do. But, it can do a lot more. Most attorneys wouldn’t dare send their entire IOLTA ledger to a cloud-based AI. But TimeNet Law already knows it. Most attorneys wouldn’t approve of a third party AI system continuously leaving fingerprints all over their entire database. Your case history, legal knowledge base, accounts, invoices, documents, relationships, on and on. But TimeNet Law already knows all of it. And that’s the secret sauce. What makes Oasis different.
It can summarize documents, analyze patterns, answer general knowledge questions and, yes, will eventually get better at researching case law and precedent without confidently hallucinating. But right now, what it’s so good at are the things no other legal AI system can do. Act on your firm’s corpus of rich history, deep context, and actual financials. Infer patterns based on your real numbers, and warn you of risks, call out your wins and help you increase them, and so much more.
Oasis is your escape. Your glass of ice water in hell. No subscription. No watching tokens rack up. No cloud middle-man. No worrying about who’s reading your data. You don’t have to hope it’s right when it answers. It’s built from your actual data, off of your real numbers. Your real context. And when it answers, it won’t be a general model thinking on a general level designed for millions of attorneys. You don’t need a jack of all trades, master of none. Dumbing things down. Glossing over. Making up responses that look good on paper but land you in hot water with the judge, or make no sense to a partner. You need a trusted advisor. A panel of experts. Actionable steps and automation that gets things handled.
It lives in your firm, learns from your firm, and will work even when the WiFi goes out. It does what you need when you need it, and you don’t have to babysit it. That’s what AI should be. And that’s what a legal AI system must be.
It’s not just a moat. It’s an ocean between you and the others. Protection from the SaaS industrial complex, isolation from the data slurping profiteers, and a genuine asset that will take your firm to the next level. I built it because I care about the vision. I care about you. I want you to succeed. And I also want to succeed. And success, for me, isn’t about a quick exit, a fat paycheck, or an easy road.
My bet was the opposite. I rode the rocky path. Fought the current. Kept TimeNet Law independent. Said no to cloud. No to forced subscriptions. And no to selling out to private equity. And now, 23 years later, TimeNet Law has become something that cannot be copied. Once you see what life is like with your own private Oasis, with intelligence, privacy, and integrity built into the DNA of the entire product, you’ll never look back.
I’m extremely proud of Oasis. It’s so much more than a chatbot bolted onto a legal billing system. It will become the lifeblood of your law firm for the next 23 years, and beyond. TimeNet Law is stronger than ever, and I cannot wait for you to experience it.
TimeNet Law 6.1 with Oasis. New version. Same vision.