Follow the Money

I ended my last letter with a question. If it's this obvious that your technology should fit your practice — and that you should own the thing your business runs on — why hasn't the industry built it for you already?

I promised you an honest answer. Here it is. It isn't a conspiracy. It's simpler than that, and harder to fix. It's incentives.

The math of your software

Start with how these companies actually make their money.

Almost all of it is priced the same way: per user, per month. Add a person, pay more. Add a capability, that's another module. The planning piece, the reporting piece, the document piece — each one tends to be its own subscription, its own login, its own line on the invoice. And the new AI features everyone is advertising this year? Those usually aren't included. They're an add-on, billed on top.

Across the category, a single seat runs anywhere from twenty to a few hundred dollars a month before the add-ons. Multiply that by your team, by the number of tools, by twelve months, by every year you stay.

Now notice what that model rewards and what it doesn't. Nobody in it gets paid when your stack gets smaller, simpler, or more connected. They get paid when it gets bigger. That's not a character flaw. It's just where the money points — and money is honest about what it wants.

Why they can't just fix it

So picture one of them deciding to do the right thing: throw out the dozen disconnected tools and build you a single foundation that just works, that you can shape, that you can own.

Three things stop them, and all three run back to that same money.

The first is pricing. If one foundation replaced the dozen products, a dozen bills go with it. No established company volunteers to shrink its own revenue, and its investors wouldn't let it if it tried.

The second is that they'd have to start over. You can't bolt a modern, thinking foundation onto software that was designed years ago to file and store — any more than you can turn a filing cabinet into an assistant by taping a phone to it. Building it right means going back to the ground and pouring it again. I made that exact call once, as I told you last time, and it's painful when it's a single system. Now imagine it's your whole company, and every customer you have is locked into the old one.

The third reason is the one that matters most to you. So I want to slow down on it.

The part about AI nobody says out loud

Right now the fashionable move in this business is to add AI to the system that already exists. A chatbot on the old client system. A copilot on the planning tool. It demos beautifully. It photographs well in a keynote.

Here's what doesn't get said from the stage. AI is only as good as the data it can actually reach and understand. And the data sitting under most of these systems was built to file and display information for a person to read — not to be reasoned over by a machine. It's scattered across tools that don't talk; in one 2026 industry survey, roughly three in four advisors said their tools still aren't fully integrated. A lot of it is locked behind gates the vendor controls, or stored as codes that mean nothing without a translator.

Point AI at data like that and it doesn't stop and tell you it's confused. It does the opposite. It hands you a clean, confident, plausible-sounding answer — one that can be quietly wrong, with nothing to flag it. For anyone personally on the hook for the advice they give a client, a confident wrong answer is more dangerous than an obvious blank.

You can see this in the numbers. A Schwab study early this year found that while most advisors are now touching AI in some form, only about one in ten who use it have actually built it into how their firm runs. Almost everyone else is using it for notetaking and drafting emails — the safe edges — as individual experiments, not as part of the system. That's not because advisors are slow. It's because you can't build deep, trustworthy AI on a shallow foundation. The tool is fine. The ground underneath it isn't.

And admitting that out loud would mean admitting the foundation has to be rebuilt — which lands right back on reasons one and two.

The honest answer

So that's the whole answer to the question I left you with.

It isn't that nobody ever thought to build you something better. It's that the companies best positioned to build it are the ones with the most to lose by building it. The pricing, the rebuild, the honesty about AI — every road back to the right thing runs straight through their own business model.

I don't say that to make anyone a villain. I told you in my first letter that most of the people in this industry are smart and well-meaning, and I meant it. But once you can see where the money points, a lot of your frustration stops feeling like a mystery and starts looking like exactly what you'd predict.

Which leaves the obvious next thought — the one a lot of you have already had. *If they won't build it, and I've got these new AI tools sitting right in front of me, maybe I'll just build it myself.*

I've spent the last two years doing exactly that. It's the most honest story I have, and it's the next letter.

Talk soon,

Ryan Borer

Founder & CEO, AdvisorCRM