6:23 PM SAME DAY
“Luke, a minute please?”
I turned. Brian was smiling, but the smile didn’t match his tone. Something else underneath. Concern, maybe. Or calculation.
“You’ve spent a lot of time on this new model,” he said, eyes on the files spread across his desk. “This is a whole new ballgame compared to what we’ve done before.”
He let the sentence sit there.
“But if you’re comfortable running this live… well, we’ll see what happens.” The smile again. It didn’t reach his eyes.
If it goes wrong, it’s on you.
I wanted to push back. The words didn’t come. I nodded, swallowed the tightness in my throat. This wasn’t just about Project Granite anymore. This was my future, and I felt the air leaving the room.
I thanked him for his trust. Asked if he had follow-up questions from the IC lunch.
“IC is very excited about this. Don’t overthink it. They want to bid strong and close out Fund 9. I share their opinion. Make it happen. Win it.” He snapped his briefcase shut.
“Prelim pricing’s already in a good range. It’s a layup. Enjoy it.”
I sat there.
“I’m heading home. Tomorrow, get the Memo in shape for Thursday’s IC meeting. Work Jeff hard enough to get the portfolio signed by end of week.”
He was already moving toward the door. I forced myself up, walked back to my workstation. More confused. More afraid.
IC was comfortable taking on an unknown portfolio with risks we hadn’t quantified. Brian was comfortable too, and he knew more than they did. IC only saw what we filtered and dressed up for them. Brian usually pushed back. Brian was cautious.
Not on this.
Project Granite sat heavier now. Radioactive.
The Mikes had helped, but they’d hit the same wall we’d been staring at since Friday. The portfolio was large. Most of it looked fine. But the assets with missing data, impossible data, gaps where numbers should be. Data is oxygen in this business.
Was I the only one short of breath?
But the message was clear - outrace the competition. Lock it up. Box them out. Run the skinny process.
We’d done skinny processes before. Not often, and none recently. When a deal looked clean and the unknowns seemed acceptably defined, moving fast had positive expected value. I understood the math. A normal bell curve, same one in everyone else’s head.
But I had never felt this level of unease before.
When was the last time I felt at ease? I tried to remember. The memory was fog, the kind that settles before dawn and burns off before you can name it. Was this just how I’d always felt? Was this good, and I was too selfish to recognize it?
Get a grip. You’re wasting time.
Twenty-four hours to finish the Memo. Dozens of slides to fill out.
I stood. The chair rolled silent on carpet. I wanted the screech of metal on tile. The office had gone quiet, the daytime noise narrowed to a murmur, and the thoughts in my head grew louder to fill the space. Screen. Window. Exit. Too much.
I walked to the kitchenette. The hum of stainless steel appliances only added to the static in my skull. I ran a hand through my hair, checked the clock. 6:45 PM. Jessica was probably eating dinner alone, waiting for another night to end without me.
I went back to my desk.
I called Jeff. Third time today.
Brokers slip up when their minds start to wander. Dinner plans, kids, the wife, the Jets game. I’d learned to call late.
I asked about the equity stakes and sub-debt relationships teased in the files. Would that be verifiable later?
“I can’t tell you about that.”
Clipped. Quick. Like he couldn’t get off the line fast enough.
Can’t or won’t?
A beat. Then: “Can’t.”
A non-answer. An answer in itself.
Not a good one. But something.
The next few hours blurred into screens. Data room files. Bloomberg searches. Old trades for comparison.
I kept returning to the same columns in the tape. Mezzanine debt. Second lien loans. Preferred equity. Hybrid structures. The flags were there, but the disclosures stopped at the flag itself. Just over a third of the assets carried one.
That wasn’t unusual. Complex capital stacks existed in plenty of pools. These arrangements were riskier for the sponsors and owners than for us. We mostly bought senior cashflows. If something went wrong, the junior positions took the hit first.
What was unusual: the silence behind the flags.
Normally I’d see more. Names. Counterparties. Executed agreements. Over years of looking at files like these, patterns emerged. You could request the docs, cross-reference the players, build a map of who held what below your position. It was check-the-box diligence, mostly. The value in that exercise came later, when a credit event hit and you needed a phone number for whoever had taken over the asset.
Those new owners rarely stayed long. They’d gotten in cheap, weren’t staffed for operations, and wanted out. Hire a management company, prep for sale, flip it back to market. Reliable profits. Second homes. Kids through college.
I knew these games. The 21st floor didn’t play all of them, but I knew the players in the sub-debt universe.
So why did Granite feel wrong?
The 21st floor was quiet now. The overhead lights hummed louder in the silence, the way they do when everyone else has gone. Twelve hours since I’d walked in. The fluorescent drone made it feel like the day had never ended.
The Mikes had done good work. Anticipated what I needed before I asked. Mike C was the last to leave; I’d had to prod him three times. He hovered at his desk, pretending to be busy, waiting to be useful. Good kid. I wanted him gone. I wanted the quiet.
I wanted to think.
Granite looked neatly disorderly. Sparse and juicy at the same time.
Jeff had whispered the asking price on my first call, once he knew I’d run scenarios. That was normal. I was a good buyer. I closed.
The price was too low.
Not the kind of too-low that means you’ve missed something obvious. This was just a good deal. Base case exceeded our return targets. Even some downside cases cleared the bar. It would be a layup for IC. A case study for Investor Relations to show our LPs.
Any other deal, I’d have chalked it up to counterparty mispricing or some edge we had in process or financing. It happened.
This one felt like sand in my teeth.
Was I inventing reasons to stay late? Was I afraid to go home to Jessica, to arrive before she was asleep, so I couldn’t avoid whatever we’d become? Was that the stage of the marriage now?
I sighed into the empty room. The ceiling lights had dimmed to half-power; only desk lamps and screensavers lit the floor. At the far end, a cleaning crew worked their way toward me, vacuum hum distant and rhythmic.
Outside, the city was haze. Cold drizzle refracted the tower lights, smearing them across the glass. For a moment I felt caged. Manhattan’s own anxious animal, pacing an enclosure of steel and glass. Something to be watched, or ignored, at the city’s leisure.
Lightning flickered in the distant clouds. I watched it, and waited, and didn’t know what I was waiting for.