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

Blackstone Hotel & Mercat a la Planxa

Assistant Director of Rooms

Director of Housekeeping

Hospitality, M.D.

Records and produces podcast in audio and video form
Leads analytics of YouTube, Anchor and Instagram activity for brand
Executive Producer for all video content
Accounting duties
Plans industry events

Managing Partner

Hilton Chicago/Oak Lawn

Director Of Rooms

theWit Hotel Chicago - A DoubleTree By Hilton

Front Office Manager

Assistant Front Office Manager

Chicago Hilton Indian Lakes Resort

Washio

Manage the distribution center by organizing supplies and orders
Support our drivers daily by preparing and dispatching driver orders
Inputting customer orders into the backend
Organize and itemize orders for our cleaning partners
Occasionally make customer deliveries

Jr. Ops Associate

Hilton Chicago O'Hare Airport

Experienced Rooms Executive with a demonstrated history of successfully working in the hospitality industry. Skilled in Hospitality Industry, Property Management Systems, Training, OnQ, and Customer Satisfaction.

Launched and produces a successful Hospitality podcast meeting with leaders from around the globe. Recorded and produced the award winning documentary "Follow Me and I Will Be Behind You"

Greg Fregoso

taplio

The Battle

Tim O'Rourke

Greg Fregoso

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