DISPATCH NO. 5 The Cut

There’s a position in my portfolio I think about more than most of the ones that are actually working. Not because it’s thriving — because it isn’t, and I still haven’t done anything about it.

Last dispatch was about editing the calendar: what earns a yes, what quietly drains you, what your attention is for. This one runs on the same logic in a different currency. The edit doesn’t stop at your time. The harder version — the one most people avoid for years — is the cut you make with your money.

Every portfolio has one. An investment that made sense when you wrote the check, that you’ve been quietly carrying ever since — not because the thesis still holds, but because walking away feels like a verdict you’re not ready to deliver.

This is where most investors bleed quietly. Not on the bad deals they never did. On the ones they stayed in too long.

Why We Hold On (And Why That’s the Real Problem)

Here’s what no one in investing talks about cleanly: the reason you can’t let go usually has nothing to do with the company.

It’s the sunk cost. The time you spent on due diligence. The relationship you built with the founder. The version of the story you told people when you got in — at a dinner, in a pitch room, on a panel where you said this one is different. Exiting means revising that story, and revision feels like loss.

But sunk cost bias doesn’t just live in portfolios. It’s the same mechanism that keeps people in jobs they’ve outgrown, partnerships that stopped working, commitments made by an earlier version of themselves who had different information. The brain codes the exit as failure because it can’t separate what was spent from what’s still possible.

The reframe that actually works: an exit isn’t a loss. It’s capital reallocation. You are not abandoning the bet — you are redirecting the resource toward something with a better probability of return. That’s not ruthlessness. That’s the job.

The Audit

1. Is it earning — actually earning? Revenue, traction, a round closing, a contract signed. Evidence that the machine is moving. Hope is not a data room, and a founder’s enthusiasm is not a substitute for a number.

2. Is it teaching you something with lasting value? Some positions earn in intelligence even when they underperform financially. An early bet in a category you’re still mapping, a founder who’s changing how you see a market — that has merit. But be honest about whether you’re learning or just staying because leaving feels worse.

3. Would you write the check today if you were seeing it for the first time? Strip out the history. Strip out the relationship. Look at what’s actually in front of you — not the version of the story you told yourself when you got in. If the answer is no, you already have your answer.

4. Are you holding on out of conviction, or out of guilt? This one matters especially if you invest in underrepresented founders. There’s a particular pull to stay — you don’t want to be another door that closes on someone who needed you to believe in them. But staying in a position out of loyalty to a narrative isn’t generosity. It’s avoidance. The most useful thing you can offer a struggling founder isn’t capital you’ve already mentally written off. It’s honesty.

What Thriving Actually Looks Like

The edit is easier to make when you know what you’re protecting capacity for.

There are positions in any serious portfolio that do exactly what they said they would. The founder executes quietly, the numbers move in the right direction, the product gets sharper with each conversation. They don’t ask for much. They send updates that make you feel like your bet was well placed. They grow into the thesis instead of away from it.

That’s what good looks like. Not perfect. Not without setbacks. But directional — always moving toward something real, with a team honest enough to tell you when it isn’t.

When you have positions like that in your portfolio, you feel the contrast immediately when you look at the ones that aren’t. The energy is different. The updates feel managed rather than transparent. The story keeps shifting to explain why the last milestone didn’t land. You find yourself doing more work to believe in it than the company is doing to earn that belief.

The ones that are working don’t need you to carry them. The ones that aren’t — no amount of carrying will change the fundamental trajectory. Knowing the difference is the skill. Acting on it is the discipline.

For Your Portfolio

Visible.vc A portfolio monitoring platform that lets founders send structured updates on a cadence you set. Standardized metrics, side-by-side comparison across companies, and a clear signal when a founder has gone quiet. Silence is data.

Notion or Airtable Portfolio Tracker Build a simple table: company, check-in date, last revenue figure, thesis status (on track / watch / exit). Review it monthly. The act of updating it forces you to confront what you’ve been avoiding looking at.

AngelList or Carta For cap table management and staying current on ownership positions. Useful not just for administration but for understanding your actual exposure across a portfolio at a glance.

A Quarterly Gut Check — In Writing No app replaces this one. Once a quarter, write a paragraph about each active investment. No bullet points, no dashboards — just prose. The act of writing forces clarity that spreadsheets don’t. If you find yourself writing around something, that’s the thing you need to look at.

Attention and capital are the same resource in different forms.

Both are finite. Both compound when directed well and erode when spread too thin. Both feel abundant in the moment of allocation and scarce the moment you realize how much has quietly drained away. And both require the same uncomfortable act: the edit.

The calendar audit and the portfolio audit are not two separate exercises. They are one decision, made in two registers. What gets your time and what gets your money should answer to the same criteria — aligned with your why, earning in some form, teaching you something worth knowing, and chosen deliberately rather than defaulted into.

The people who build well — not just wealth, but lives that actually hold together — are not the ones who said yes to the most. They’re the ones who got precise about what deserved a yes and protected that standard even when it was uncomfortable.

The edit is not a moment. It’s a practice. And like any practice, it gets cleaner the more honest you’re willing to be with yourself about what’s actually working.

Let go cleanly. — E