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 CFA charterholder transitioning from corporate treasury into capital markets and investment management, bringing a unique blend of analytical rigor and operational execution to portfolio and capital allocation decisions.

My background bridges investment analysis, debt capital markets, and balance sheet strategy. I have owned end-to-end decisions on FX exposure management, debt portfolio optimization, liquidity planning, and fixed income execution. This work translated market signals into frameworks that improved forecast precision by 25% while strengthening how currency and balance sheet risks were evaluated at the enterprise level.

What differentiates my approach is decision ownership, not just analysis. I frame the problem, evaluate scenarios using derivatives and fixed income instruments, assess counterparty and liquidity risk, recommend the action, and implement the solution. Then I communicate implications clearly to CFOs and senior leadership. I work where judgment determines outcomes, not just process.

I am pursuing roles in capital markets, investment management, and portfolio management where my treasury foundation becomes an advantage: understanding how funding costs, balance sheet constraints, and liquidity dynamics influence investment decisions. This includes portfolio manager, investment manager, and capital markets roles at asset managers, insurance companies, corporate treasuries, and financial institutions.

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Tim O'Rourke

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