“I built Ollie because every question about my own business came with an invoice.”

I run a handful of small businesses — Choquer Agency, Futur Labs, Webflow Jobs, Motorsport Illustrated, Pennycart, and for years, Pedigree Painting. None of them has an accountant on staff. Like most small businesses, we work with an outside accounting firm and a hired-out bookkeeper.

Which meant every real question about the business came with a bill. Not just the answer — the conversation. Before I could even sit down to talk something through, the bookkeeper had to go prepare documents first. For data that already lived in QuickBooks. Then I’d wait days for the answer to a question I’d asked on a Tuesday.

The strategy questions were worse. Ask one and you’d get averages back — “businesses your size typically see…” I didn’t want typical. I wanted an answer from my books. My actual numbers, my actual customers, my actual QuickBooks file.

Then AI got good enough that there was no reason not to ask the books directly. That’s the part that changed everything: the AI does the research 100% of the time, with zero bias. It doesn’t glance at the numbers and guess. When I built the first version of Ollie, it connected issues it found in the system to how the business actually felt to run — did the digging, and came back with specific, cited answers.

Now? I finally have a pulse on the business. I’m curious by nature — questions come up constantly — and there’s finally a tool with no dumb questions and no waiting days for a report. It saves me a minimum of about $300 a month in bookkeeper time, and my businesses still work with our accounting firm for the things that genuinely need a professional. Ollie didn’t replace the people. It replaced the wait.