Every operator I know is wired to chase. There’s always a new deal, a new asset class, a new opportunity across the desk. It feels like ambition. A lot of the time it’s just noise.
This week I did the opposite. I spent a morning not chasing anything.
I sat down with Claude and built one view of my entire financial picture. Operating businesses, every property, every loan, the investments, the cash. All of it in one place. Then I asked one question: am I being intentional, or am I just reacting to whatever showed up this year?
Most of us are great at offense. Build the business, find the next deal, make it happen. We have almost no defense. No plan for everything the business throws off once it’s working.
How I actually did it
I pointed Claude at the raw facts. Bank statements. General ledger exports from each property. Investment statements. Then I had it rebuild my numbers from scratch instead of trusting the summaries I already had.
That’s the part that matters. Not a spreadsheet I typed my own estimates into. A source of truth built from the actual transactions, reconciled back to the P&Ls. When you build the picture off your bank statements, you can’t sugarcoat it. You have to confront the brutal facts of where you actually are.
A few things I made it measure honestly:
Real estate on return on equity, not “what’s it worth.” The question most balance-sheet investors skip. Don’t ask what the property is worth. Ask what your equity is actually earning sitting in it. A property can be a great asset and a lazy use of your equity at the same time. Over a long hold with amortizing debt, more and more equity gets locked up while the return on it quietly drifts down.
Cash flow with CapEx honestly counted. This is where operators fool ourselves. CapEx lives below the NOI line, so we don’t talk about it. I pulled the last 18 months of actual CapEx spend plus what’s planned for next year and fed it right into the real numbers. Cash flow before CapEx is a fantasy.
A real reserve floor. Six to twelve months of all debt service and operating expenses, held in something liquid. Not “some cash over here.” A hard line, defined as months of obligations. As a business owner you’re already all-in. Sitting on cash feels lazy, so we deplete reserves into the next good idea. The floor is the discipline that keeps you out of forced-seller territory when the wind blows.
The whole thing was iterative, and that’s the unlock. I kept remembering things. Oh yeah, the retirement account. Oh yeah, that upcoming expense. I just told it, and the model updated as fast as I could think of the next detail. It’s not a static spreadsheet you punch formulas into. It’s a living model you think out loud at.
The two things that surprised me
First, liquidity. When I laid everything out in one place, I was in a better position than it felt day to day. The cash was there. I’d just locked it across different operating accounts where it never read as reserves. You can’t manage what you can’t see. The scattered picture had me feeling tighter than I was, which is exactly what pushes you to chase yield you don’t need.
Second, taxes. The model forecasted my liability for the year, and it surfaced that I was paying real taxes that were never in my cash flow budget. Not that I wasn’t paying them. I was. They just weren’t in the plan, so they hit my liquidity sideways every year. The most predictable bill I have, treated like a surprise. Once it’s in the budget, it stops running my liquidity around.
What I actually did about it
Intentionality is subtraction. Two decisions came out of that morning.
I’m listing three properties that are lazy on return on equity. I had a hunch, but I wasn’t keyed in until the numbers were in front of me. That equity works harder somewhere else.
And I’m holding cash I’d normally have already deployed, to rebuild the reserve floor.
Here’s the reframe for any operator: the skill isn’t finding opportunities. There are opportunities everywhere if you’re looking. I have too many on my plate right now. The skill is the discipline to say no to the good ones, so the great ones, and your own safety, still have room.
How to start
If you want to run this yourself, it’s simpler than it sounds. Download your statements and GL exports into one folder. Point Claude at it. Tell it to interview you on your goals and your read on the economy, then build the dashboard from your actual numbers, not your estimates.
That workflow, and the rest of the ones I run across NPI and LeisureQuip, is in the playbook I wrote. Free at neelypi.com/playbook.
Build it once. Think out loud at it forever.
— Brent