15 years in bookkeeping.
Every client loved me for the first 6 months. By year two? At each other's throats.


I ran a fractional bookkeeping business. In the beginning? I was great. New clients, 
new systems, new problems. But once the novelty wore off—same reconciliations, 
same reports, same emails asking for the same missing documents.
I thought the problem was the clients. The work. Me.
Then I got diagnosed with ADHD.
Turns out my brain runs on uniqueness. I need to feel like what I'm doing is special, 
different, mine. Repetition kills that. So I stopped fighting my wiring and started 
building around it.
Now I build AI tools that solve real problems for real businesses—starting with the 
industry I know cold.
First up: OnboardLy. It kills the document chaos that happens before bookkeepers 
can even start their real work. Because the worst part of a bookkeeper's job isn't the 
bookkeeping—it's hunting down missing bank statements at 11pm.
I work in 10-week sprints. Build, market, launch, rotate. It's the only way my brain lets 
me finish anything.
My white whale? The search tool Ezra Klein said newspapers need. Ask a question, 
get a syllabus—not a list of links, but a structured path through the archives with every 
source at your fingertips. I'm the one building it.
I'm documenting the whole journey here. Wins, failures, everything in between.
Fractional bookkeeper drowning in client onboarding? Let's talk.
Building software for an industry you've never worked in? I have thoughts.

Tim O'Rourke

I am a ND, Black woman in America raising 3 Black boys. My passion is,

Humanity.
Writing.
My Community.

I fight 366 for ✊🏾, 

Justice
Equity.
Inclusion.

I amplify 📢, 

The Culture.
Black Women.

I protect 🛡️ ,

Black people, at all costs.

taplio

The Battle

Tim O'Rourke

AJ Jefferson

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