The cursor is blinking at 11:01 PM, and I am staring at a spreadsheet cell that demands to know the churn rate of customers who signed up on a rainy Tuesday in 2021. It is the 11th week of what the associate at the venture fund calls “preliminary digging.” My eyes are burning, a sensation I actually googled at 1:01 AM last night when I convinced myself I was developing a rare form of digital retinal fatigue. The search results for “blurry vision after 11 hours of Excel” were predictably grim, suggesting everything from mild dehydration to immediate lifestyle overhauls. I chose the dehydration theory and drank a glass of water, then went back to Row 121 to calculate the LTV of a cohort that likely no longer exists.

This is not due diligence. This is a theatrical performance. In the 11th hour of the 11th day of the month, I realized that the analyst on the other side of the screen isn’t looking for a reason to say yes. They are building a fortress of data to protect themselves from the fallout of saying no. It is a slow-motion ghosting, a bureaucratic dance where the music stopped 21 days ago, but everyone is still swaying because they are afraid of the silence that follows a rejection. We have provided 81 different cuts of the same 11 datasets, and yet, the request for “one more thing” arrives with the rhythmic inevitability of a tide that only goes out.

The Bargaining Phase of Grief

Casey R., a grief counselor I spoke with recently about the emotional toll of founder burnout, has a very specific way of looking at this. She sits in an office filled with 31 different types of succulents and always wears mismatched wool socks, a detail she once told me keeps her grounded when people are falling apart in front of her.

“Bargaining is the most deceptive stage of grief because it feels like productivity.”

In the world of venture capital, the endless request for more data is the bargaining phase. The investor knows the deal doesn’t quite fit their current mandate, or they’re spooked by the macro environment, but they don’t want to close the door. So, they bargain. They ask for the astrological signs of the founding team-not literally, but close enough-to keep the process alive without ever having to pull the trigger on a $1000001 check.

The Cost of Attrition

I hate these requests. I spent 41 hours last week building a sensitivity analysis for a market pivot we aren’t even planning to make, just because the junior analyst mentioned it on a casual 11-minute call. I do it because there is a sliver of hope that the 101st data point will be the magic key that unlocks the vault. But it never is. The data isn’t being used to find the truth; it’s being used to exhaust the founders until they stop asking for a decision. It’s a war of attrition where the weapon of choice is a VLOOKUP.

When a firm is actually excited, the diligence feels like a partnership. It moves fast. They look at the 11 core metrics that actually matter and they make a call. When they aren’t excited, they look at 151 metrics to find one that is slightly off, so they can point to it as a justification for their hesitation. It is a psychological shield. If the startup fails later, the investor can say they were thorough. If the startup succeeds and they passed, they can say the data was inconclusive. In both scenarios, the process protects the person, not the capital.

I remember one specific deal from 2021 where we were asked to provide a breakdown of shipping costs by zip code for a software-as-a-service company. We don’t ship anything. We are purely digital. I spent 31 minutes explaining this to a 21-year-old associate who just kept nodding and saying it was part of their standard checklist. That was the moment I realized the checklist had become the master, and the human brain had been relegated to an administrative assistant for a set of arbitrary rules. We weren’t talking about business anymore; we were talking about the performance of being a serious person who asks serious questions.

The Need for Clarity

This is why founders need an advocate who can see through the smoke. It is easy to get lost in the weeds when you are the one doing the weeding. You need a team that understands when a question is a genuine inquiry and when it is a polite way of saying “I’m too scared to commit.”

I’ve seen founders go through 51 rounds of revisions on a pitch deck only to be told that the “timing isn’t right.” The timing was never right. The timing was decided in the first 11 minutes of the first meeting, but the ego of the institution required a 1-month-long autopsy of a living company. It is a cruel way to handle people who are pouring their lives into their work. Casey R. would call it a lack of emotional intelligence, but in the Valley, we just call it “thoroughness.”

Stop Rewarding the Theater

We need to stop rewarding the theater. We need to start demanding clarity. If the answer is no, say it in the 1st week, not the 11th. Don’t make me spend 91 hours on a deck that will sit in a Dropbox folder until it’s deleted to make space for the next victim of the “Slow No.” There is a cost to this delay. It’s not just the money; it’s the momentum. Every hour spent on a useless spreadsheet is an hour taken away from building the product or talking to actual customers who might actually pay for the service.

I have 11 tabs open on my browser right now. One is the spreadsheet. One is a job posting for a librarian because it sounds quiet. Three are research papers on the psychology of decision paralysis. The rest are just noise. I think about Row 121 again. If I change the growth rate from 21% to 31%, does the analyst feel better? No. They just ask why it isn’t 41%. The goalpost isn’t just moving; it’s on wheels, and there’s a jet engine attached to the back of it.

Reclaiming the Resource: Time

There is a certain irony in writing this while I wait for a 1:01 PM call with a new lead. I’ll put on the smile, I’ll have the 11-slide deck ready, and I’ll answer the first 31 questions with precision. But the moment they ask for something that feels like theater-something that feels like a shield-I’m going to remember Casey R. and her jade plant. I’m going to remember that my time is the only non-renewable resource I have. I might even tell them no before they can tell me their version of it. It’s a terrifying thought, but so is the idea of spending another 41 hours calculating the LTV of a rainy Tuesday.

Walking Out of the Play

In the end, we all want the same thing: a decision. Whether it’s a yes that launches a thousand ships or a no that lets us move on to the next harbor, the truth is always better than the theater. We just have to be brave enough to stop playing the part. The 111th metric isn’t going to save the deal, and it’s certainly not going to save your sanity. The only thing that saves you is realizing that the process is the problem, not the data.