Unreconciled: The Business of Accounting

Most firms land somewhere near $250,000 of client revenue per accountant. Pilot targets a million, and Waseem Daher’s position is that the gap is as much about pricing as it is about AI.

He co-founded Pilot, which runs as two things at once: an accounting firm with about four thousand clients, and Meridian, the software other firms use to run their own closes. He still does the books for a couple hundred clients himself. It’s how he finds out what’s broken at eleven at night.

What has to be true before any of this works is less exciting than the demo. You need inputs you can actually get. You need a process someone has written down. And you need incentives that aren’t quietly pulling against the thing you’re trying to do.

Jeff Seibert wrote software for thirty years. Last December he realized the agents had gotten better at it than he was, and by the first week of January his whole team had stopped writing code by hand. Digits is up 80% on engineering output since, without losing anyone. The work didn’t disappear, it moved to review.

He thinks accounting is a year behind on the same road, with one difference that matters. Software is text in, text out. Accounting is structured data in and the same answer out every month, and language models are bad at that by design. Digits uses predictive models instead, and eats the token cost rather than passing it to firms.

He’s also skeptical that those costs keep falling. His view is they go up once the subsidy runs out, and he points at what happened to Uber.

There’s one thing agents still can’t do, and it’s the thing everyone assumes is solved. Matt gets him to name it near the end.

Most firm owners will tell you AI can't close a set of books. Ben Stein says it can, and has been able to for a month or two now.

What changed isn't accounting. Models have handled categorization and reconciliation for ages. They just couldn't log into the bank and pull the statement. And if a person still has to do that bit by hand, automating the rest barely helps. They're already sitting there.

Ben runs Double and closes his own books this way. August was almost entirely agentic.

Matt pushes him on the bit these conversations skip. If you already run a team in the Philippines or India, agents cost you more right now. Ben agrees, then explains why he doesn't think that lasts.

The rest is structure. Which layer of a firm thins out, which one never goes away, and why nobody has the documentation to hand an agent the close and walk off.

Decimal went from a handful of clients to 125 in two years, bought a company from KPMG, and broke most of what it had built getting there.

Then rebuilt it, sold the firm, and became a franchise business.

Matt Tait, Jacob Cloran, and Michael O'Connor go back through the whole arc: the growth, the damage, the fix, and the decision that turned it into what they're doing now.

Episode includes:

• Why onboarding breaks before delivery does, and why hiring your way out stops working

• What a hundred acquisition targets taught them about buying accounting firms
• Why a $1.6M firm that pays its owner $100K is the problem franchising is meant to solve

Unreconciled is hosted by Matt Tait, CEO of Decimal.