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Chapter 4

The Pass

About 18 minutes to read

The Ostrander office began its diligence at eight o’clock on Monday the second of November, through the speakerphone in the middle of the long table downstairs.

Andy sat with Maggie on his left and Beth Ann on his right. Anika had taken the end of the table with a pencil and her own printed copy of the data room index, and Tom stood by the door with his coffee, because he said he listened better on his feet. Through the window behind the phone the back lot was still in shadow.

Renata Szabo ran the call. She had a level, even voice and spoke in whole paragraphs, and Andy guessed she had written them out beforehand. She had spent the weekend in the room, she said, and she already had questions, which she would send that evening against the index numbers so that nobody had to guess what she meant. She would work from her own office through Wednesday and come to Bee Cave on Thursday. She would speak to the fund auditor, the administrator and the firm’s outside counsel herself, with nobody from the firm on the line, and she would be grateful if someone wrote to each of them that week to say the firm had authorized them to answer her questions. She would want references: a few LPs, a lender, a property manager. She would run the usual background checks on the principals and would need each of them to sign a consent. On Thursday she would like to sit with people one at a time.

“Most of what I do is ask to see things,” she said. “Please don’t take it personally if I ask to see something you’ve just told me.”

“We won’t,” Andy said.

Travis Oyler had been quiet through all of it. At the end he spoke once.

“We appreciate the room,” he said. “I know what it takes to put one together on short notice.”

Andy thanked him. When the call ended Maggie was already writing on her pad, and by the time he reached the top of the stairs she had sent him a draft of the letter to the service providers, with a blank where each firm’s name would go.

Renata’s first list came in at 5:12 that afternoon, and Andy read it at his desk. Every question named a folder and a page. The IC memos were in folder nine, and she wanted the minutes of the meetings at which each memo had been approved. The compliance manual was in folder three, with Anika’s amendments on its first page, and she wanted the version that had been in force before the amendments and the record of each year’s review. The Fund II waterfall was in folder twelve. She wanted the administrator’s calculation of the most recent distribution set beside the controller’s, and the sign-off on each.

He forwarded it to Maggie with one word, owners?, and she sent it back inside the hour, sorted by desk.


On Tuesday Renata spoke to the auditor in the morning and to the administrator after lunch. Andy was on neither call, which was the point of them. At ten to five a short note from her came in for Tom, with Maggie and Andy copied.

Following my call with the administrator: please describe how differences between the administrator’s waterfall calculation and the controller’s workbook are resolved each quarter, who approves the final figure, and how long this process has been in place.

Tom came up the floor with it printed out and stood in Andy’s doorway.

“They told her the truth,” he said.

“Which is?”

“They run theirs and I run mine. When the two don’t match, we go with mine, and they book an adjustment.”

He folded the page once along the middle. “She’s going to ask me how long.”

“What will you tell her?”

“How long,” Tom said, and left.

On Wednesday it was outside counsel’s turn. Afterward the partner who handled the fund documents sent Anika two lines, and Anika forwarded them to Andy without adding anything of her own. Routine call. She asked whether we had reviewed the allocation policy, and when.

At 4:40 that afternoon Renata wrote to the deal team, Wyatt and Nadia, with Andy copied. One of the Fund III properties outside Raleigh had taken co-invest from a few of the fund’s families when it was bought. She asked how many of the fund’s families had co-invested, how the allocation among them had been decided, and what had been distributed to each of them since, by date, with the investors identified by letter.

Wyatt forwarded it to Nadia a few minutes later. Can you take this? I’m buried in the Fund IV close. Fund IV’s first property was due to close on the sixteenth, and Wyatt had been on the phone with the lender’s counsel since noon.

Nadia’s reply went out at 11:40 that night. Andy read it on Thursday at 7:20, standing at his desk with his coat still on. It read well. It listed the investors by letter, explained in two clear sentences how the co-invest had been offered to them, and gave the total distributed to the co-investors since the purchase, with the date of each payment set out underneath. It was courteous and short, and it answered everything Renata had asked. He looked again at the time it had gone out, and took his coat off.


Renata Szabo pulled into the back lot in a rental car at 8:25, parked beside Tom’s, and came in through the back door with a canvas bag over her shoulder. She was in her forties, small and composed, and she shook hands with everyone she passed on the way to the conference room. She declined coffee and asked for water and the wifi password, and she asked whether the door could stay closed between interviews.

She set out a laptop, a bound notebook with numbered pages and her own printed copy of the index, flagged down the side in colored tabs. Most of the notebook was already written in. She opened it to a clean page and wrote the date at the top.

“I’d like to start with how a deal comes in,” she said. “You and Mr. Pruitt, if that suits.”

Wyatt came down with his laptop and put the tracker up on the screen at the end of the room. Renata had him take her through it column by column. She asked where the deals came from and who saw them first, how long one usually sat before somebody decided something about it, and who could move it forward. Wyatt answered well. He had a quick, plain way of describing his own work, and Andy found himself listening as if he had never heard it.

Renata pointed her pen at the status column on the screen. “Before a deal goes to the committee, what does it have to meet?”

“The buy box,” Wyatt said.

“Is it written down?”

Wyatt glanced at Andy. Andy waited for him to open a file, because he had always assumed there was one. Wyatt opened his email.

He searched for a few seconds and brought up a chain from 2023, from before he had joined the firm. Andy knew the subject line before he could read the text under it. He had written it himself, on a Sunday, to the deal team as it was then: which markets, what vintage of property, what size, how far below replacement cost the firm wanted to buy. Scott had replied with a correction about Chattanooga. The analyst at the time had asked whether the size range was firm, and Andy had answered from his phone in one line.

“Scott forwarded it to me my first week,” Wyatt said. “It’s where I started.”

Renata read the whole chain on the screen, top to bottom. Then she scrolled back up and read Andy’s one-line answer again.

“Is there a later version?”

“This is the one I have.”

“Has the firm bought anything that sits outside it?”

Wyatt thought before he answered, and Andy liked him for that. “Depends how you read the size range.”

“Could you send me the chain as it is, with the dates?”

“Sure.”

She thanked him and turned the page. When Andy went back upstairs a little later, Wyatt was at his desk by the front window with the chain still open on his left screen, and it stayed open all morning.

Tom went down at ten and came back up after twelve. From his glass wall Andy watched people go down the stairs and come back up again, and he tried to read the interviews in their faces. Beth Ann went down twice with an armful of side letters and came back with fewer of them each time. She had been at her desk until after one the night before, and she smiled at everyone and spoke more slowly than usual.

At twenty to one Tom stopped at Andy’s door with a sandwich from the kitchen.

“She asked how long,” he said.

“And?”

“I said, ‘Since the administrator moved us onto their new system.’” He unwrapped the sandwich. “She wrote it down. Then she asked who checks my workbook.”

“Who does?”

“The auditor, at year-end.” Tom looked at the sandwich. “Every other quarter, me.”

He took it back to his desk and ate it over the keyboard.


At half past two Renata asked for Anika and Andy together.

Anika came down with nothing in her hands. Renata began with Anika herself: where she had practiced before she came to the firm, when she had taken on compliance beside the legal work, who reported to her.

“The compliance manager, since 2022.”

“And in a normal week, how much of your time goes to compliance, and how much to legal?”

Anika thought about it honestly, the way she thought about everything. “Since September, most of it to compliance. Before that, whatever the legal work left over.”

Then she opened the folder marked Allocation on her laptop and turned the screen a little so that they could both see it.

“Tell me how this works in practice.”

Anika took her through it in the order the policy itself used, from the first section to the log at the end, without once looking at the screen.

“And before the policy?” Renata said. “The Raleigh co-invest in Fund III, for instance. How was that decided?”

“I decided it,” Andy said. “Whoever had asked first.”

“Was the order written down anywhere at the time?”

Andy looked at Anika, and Anika answered.

“It is now,” she said. “We formalized the policy three weeks ago.”

Renata nodded. She moved the cursor to the top of the window and opened the document’s properties, and the small gray box sat on the screen for a moment where Andy could read it from his chair. Created: Monday, October 12, 2026. Renata typed a line into her notes, closed the box and said nothing about it.

“Could I see the log?”

Anika opened it. It was a clean spreadsheet with careful headings across the top: Fund, Deal, Date, Allocated To, Reason, Approved By. Under the headings there was nothing, because the firm had not bought anything since the twelfth of October.

“Thank you,” Renata said. She looked down at her notebook. “One more thing, if Ms. Farooq has a few minutes.”

Nadia came down with her own notebook. Renata asked her to sit beside her where she could see the laptop, and Andy moved his chair around so that he could see it too.

On the left side of the screen Renata had Nadia’s email from the night before. On the right she had the data room, open to the distribution notices for the Raleigh co-invest, one for each payment, each with the administrator’s name across the top. In the margin of her notebook she had added the notices up in pencil.

“I tie out every figure that comes to me in writing,” she said. “This one doesn’t match the notices. Can you show me where it came from?”

Nadia read her own letter. Andy watched her read the paragraph with the distributions in it, and read it again, and then go through the notices on the right side of the screen one at a time, as Renata had.

“I can find out,” Nadia said.

“I’d appreciate that.” Renata’s voice stayed exactly where it had been all day. “Did you write the reply yourself?”

The room was quiet enough that Andy could hear the refrigerator running in the kitchen across the hall.

“An assistant I use drafted it,” Nadia said. “I read it, and I sent it.”

Renata wrote that in her notebook. “Thank you for telling me.”

She worked on alone with the door shut until a quarter to six. Andy walked her to the back door. In the lot she set the canvas bag on the passenger seat and sat for a minute with the dome light on, writing in the notebook against the steering wheel, and then she backed out and drove toward 620.


Nadia’s email came in late that night, to Andy and Tom. She had found it. Back in September a draft summary of the Raleigh deal had gone around the deal team, before Tom had corrected the distribution table, and the draft was still in her mailbox, where the assistant had read it. She attached the draft and Tom’s final side by side. I read the reply before I sent it, and it looked right to me. I didn’t check it against the notices. I’ve disconnected the assistant from my mailbox. It stays off unless Anika says otherwise.

Tom replied at 6:47 the next morning with the correct total and the notices attached. Before eight Nadia sent Renata the correction with the documents, copying Andy and Tom, and one plain sentence on where the first figure had come from.

On his way past Anika’s office Andy put his head in the door.

“Nadia’s service. Where are we?”

“Two letters to their legal address and two form replies,” Anika said, without looking up from what she was reading.

By Friday afternoon most of the LPs on the reference list had rung Beth Ann to tell her that Renata had called. Beth Ann came to Andy’s door at four with a page of notes.

“They were good,” she said. “All of them. She called a few people who weren’t on the list, too. Arturo’s property manager in San Antonio rang him afterward to ask whether he should have talked to her.”

“What did she ask?”

“What you’d expect. Reporting. Whether we’d ever surprised them. How we handled a bad quarter.” She was quiet for a few seconds. “And who else at the firm they talk to.”

“What did they say?”

“Me, now and then.” She looked down at the page. “Mostly you.”

Andy nodded. Beth Ann left the notes on the corner of his desk and was dialing again before she reached her own desk.


Renata’s list came in on Monday morning, the sixth day. It was the longest she had sent, and the first with a heading: Outstanding items.

Andy read it slowly. The minutes of the investment committee meetings for every deal in Funds I through III, which did not exist, because the committee had approved those deals in his office and nobody had written down anything but the memo. The firm’s written investment criteria, with any history of changes. The allocation record for the period before the twelfth of October. The administrator’s reconciliation for every quarter since the change of system, with the approvals. A succession plan for the chief executive. An outside test of the firm’s cybersecurity. Any policy governing the use of AI tools on firm or investor data.

He had seen most of the list before, line by line, in Maggie’s handwriting.

He looked down the floor. Maggie’s door off the landing was shut.

It was 9:04. He went back to the last page of the list and read it again, and when he looked up the door was still shut. At 9:14 Maggie’s door opened.

She came down the length of the floor with the list in her hand and sat. There was a name in the margin beside every line, in her small upright hand.

“I’ve given every one of these to somebody,” she said.

“OK.”

“Two of these are yours, the criteria and the succession plan. They’ll take longest.” She stood up. “I’ll tell Renata who to expect each answer from.”


On Wednesday at four, the eighth day, Travis and Renata called for the closing session. Andy took it in his office with Maggie, the phone on the round table between them.

Renata went through the areas she would write up in the order she had found them, without an adjective in any of it. When she had finished, Travis spoke, in the same unhurried voice that had asked over the elk at Walt’s table who reconciled the waterfall.

“Andy, is there anything Renata’s said that’s wrong on the facts?”

Andy looked at Maggie. She shook her head once.

“No,” he said.

“Then that’s what we’ll write.” There was a short pause on the line. “Your people were open with Renata. Nobody tried to dress anything up, and that doesn’t always happen. Russ will be in touch.”

When the call ended Maggie sat for a moment with her pad on her knee. Then she picked it up and left.


Fund IV closed on its first property on Monday the sixteenth. Andy signed the last of the documents at ten in the conference room with the title company on the speakerphone, and by two o’clock Tom had the first capital call notices out to every investor from the first close, calling the money that would repay the credit line that had funded the closing. Andy had read the notice before it went: a page of plain language, the amount due and the date, the wire instructions. The investors ran down the page in a single column. There was no line for the Ostrander office, and there would not have been one yet in any case.

The week before Thanksgiving, Russ’s assistant moved the call Beth Ann had asked for to the week after. The week after, she moved it again. The replies came a day later than they used to, and then later than that. Andy had passed on enough deals to know how a pass sounded before anybody said it, and he had done it himself, to brokers he liked. Everyone stayed very polite. Beth Ann left another message and heard back from the assistant.


Russ called on Wednesday the ninth of December, at ten past three in the afternoon, on Andy’s cell.

“Andy. Russ Whitlow.”

“Russ.”

“I wanted to call you myself. Walt asked me to, and I’d have done it anyway.” He went straight to it. “Travis’s team recommended we not go forward with the anchor commitment, and I’ve agreed with them. We won’t be coming into Fund IV.”

Andy had his pen in his hand. He set it down across the legal pad.

“OK,” he said.

“I want you to hear the why from me. Your returns are strong. We like the strategy, and we still like the deals. Travis’s report runs long. You’ll have his list of findings by Friday, and it’s a fair list. I’ve read it twice.”

“Was it the reply?”

“The reply was the part I could explain to Walt in one sentence,” Russ said. “The rest of the report took longer.” He was quiet for a second. “Honestly, Andy, we’re just not sure your firm is ready for a check with an extra zero. Not yet.”

Andy looked down the length of the floor through the glass. Nadia was at her desk with both monitors lit, and at the front window Wyatt was on the phone with a broker.

“I understand,” he said. “Thank you for calling me yourself.”

“I’m sorry, Andy.”

“So am I.”

He put the phone down beside the legal pad. Since September he had built every working day around fifty million dollars. He sat for a while. His jacket hung on the back of his chair. He took Lorraine’s page out of the inside pocket, did not unfold it, and put it back. Then he picked up the phone again and typed with his thumb.

they passed. wrong on infrastructure.

The answer came back before he had set the phone down.

I know. Let’s talk tomorrow.

He sat a minute longer. Then he stood, put on the jacket and walked down the floor to Beth Ann’s desk. She was on a call, walking back and forth by the window. She saw his face, told whoever was on the line that she would call them back, and sat down.

From the author

A Note on Chapter Four

Renata’s questions are ordinary ones. Every institutional sponsor I know has answered a list like them.

I have received these requests myself, and I have watched other firms receive them. A comprehensive request arrives, or a single line asking for the data room, and that is where the real questions start. The first one is always the same: how are we going to get all of this ready quickly?

The hardest part for an operating business is going back over the last few deals and rebuilding the answers to questions nobody asked at the time. The information usually exists. It sits in the order the firm did the work: by property, by quarter, in the inbox of whoever worked the deal. The questionnaire wants it in a different order, one question at a time and across every deal at once. Who approved this, on what basis, and where is the record? What went to each investor, and on what date? Somebody has to carry each answer from the firm’s order into the investor’s, against a deadline.

An answer that reaches an investor in writing needs its source beside it. I learned how much that matters at a lunch table.

At a firm I was advising, the asset management team had come to suspect that one of the firm’s joint-venture partners was starting to default, in a pattern that matched a longer history of bad behavior toward other counterparties. They had enough soft signal to feel sure of the pattern and too little hard evidence to act on it. I opened my laptop at the table and put an AI research tool to work while they watched.

The results came back rich, and every part of them agreed with every other part: lawsuits in several jurisdictions, properties at specific addresses with specific histories, conduct that matched in detail what the team was seeing in its own deal. No part of it read as suspect, because it fit a theory everyone at the table already held.

That afternoon, alone at my desk, I went to check the sources. I could not find the first lawsuit in any docket I searched, or the second. The properties did not exist at the addresses the tool had given, and the company had never owned them. It had put together a complete record of conduct that never happened and handed it, with full confidence, to a room of professionals who in any other setting would have trusted a citation.

I walked the asset manager through what had happened. He shrugged. “Well, we didn’t really understand AI anyway.” Nothing went into a memo, and nothing reached an investment committee.

The team put it down to their own inexperience with the tool and left it there. No step in the way that firm worked asked an answer to show where it came from before it reached a room full of people, and an answer that agrees with what the room already believes is the one nobody thinks to trace.

Both problems give way to the same piece of work, and you can do it before anyone sends you a list.

Take the deal you closed most recently and open a blank document. At the top of each page, write one question an investor’s team is sure to ask about that deal: who approved it and on what basis, how any co-invest was offered, what has been distributed and when. Under each question, put the documents that answer it, the signed memo, the notice, the statement, in the order an investor would read them. When you catch yourself typing an answer from memory, stop and go find the document it should have come from, and if nobody can find it, leave that page unfinished. When the last page is done, save the file under the deal’s name in the place where the next person who has to answer for that deal will open it first.

You are reading the working draft of 2 October 2026. Corrections and comments are welcome at chi@chiraghathiramani.com.