In March of 2018, Matthew and I flew to an IT managed services conference in New Orleans. On the surface it made no sense (nothing new for the two of us). We were running an accounting firm not a tech services firm. But we were also trying to imagine what bookkeeping would look like as it evolved.

We kept coming back to the same idea.

Bookkeeping was eventually going to follow the same path as IT.

Not a reactive service.

Not a monthly slog.

Not a person grinding through tasks.

But an always-on system that quietly keeps a business financially healthy in the background, with humans stepping in only for exceptions and interpretation. Just like managed services.

At the time, this felt very compelling to us, but the technology to enable this simply wasn’t ready.

Now it is.

AI-first GLs like Digits and Rillet are building what we were imagining back in 2018. Real continuous accounting. Actual system-level monitoring. Automatic cleanup. Pattern detection. Exception surfacing. The foundations of a financial operations layer that act more like infrastructure than a service.

And CAS firms are starting to take these tools seriously. Not as experiments or side projects, but as legitimate options for their clients. That shift alone signals how fast the model is changing.

We’re entering a world where bookkeeping becomes continuous.

Where categorization and reconciliation happen automatically.

Where humans focus on the story and decisions behind the numbers instead of the mechanics of producing them.

This is the model we saw as highly likely back in 2018. We just couldn’t build it yet.

Now it feels like that time has arrived.

It just took the industry a few AI breakthroughs to get here.

Photo: Special shoutout to our friend, Amanda Aguillard. She tolerated us all of those years ago with our crazy ideas while leading us on an epic New Orleans bar crawl.