The work of winding down a portfolio didn't arrive as one dramatic moment. It arrived as a list: restructure a deal, let people go, sell a business. I had built a portfolio company and lost $10M+ doing it.
That loss was financial. It was also a long look at the kind of growth I had been chasing, and the fear sitting underneath it. Later, a mentor asked me to tell the whole unaltered story. I let go of 23 businesses I owned equity in.
What did the collapse look like from the inside?
There's a version of business loss that makes for a clean story. A market turns. A partner disappears. A single decision breaks the whole thing.
This was messier. The portfolio didn't work. I was trying to acquire and invest across multiple businesses after a strong run of profit. There was speed. There was momentum. There was enough evidence to believe I could keep expanding the surface area of my life.
Then the surface area began to own me.
By the time the wind-down was underway, the work was repetitive and heavy. Restructure a deal. Let someone go. Sell a business. A decision that had once sounded like expansion became a series of responsibilities that had to be faced one at a time.
I don't call it a $10M+ loss for effect. That's the canonized frame for what I lost while building the portfolio company. The number names the scale. It doesn't explain the experience.
The experience was watching a story I had told myself lose its power. Bigger had started to feel safer. More businesses had started to feel like more control. Most of the time, those beliefs don't announce themselves as fear. They sound like ambition. They can even look sensible on a spreadsheet.
A business can have strong revenue, smart people, and a convincing deck. The inner reason for building still follows you into every meeting. I had spent years teaching systems across marketing, sales, delivery, operations and team, finances, and mindset. In this season, I was living the cost of treating those areas as separate.
That's why the Six Pillars framework matters to me now. A business isn't a machine with a founder attached. It usually reflects the founder's pace, appetite, avoidance, and need for certainty.
How did expansion become accumulation?
I wanted to build something bigger. That part was easy to say.
What I had not examined enough was what “bigger” was doing for me. A portfolio can become a way to avoid sitting with the uncertainty of one clear business. Each new company gives you another place to put hope. Each new opportunity gives you another reason to delay the harder conversation.
Usually, accumulation feels good at first. You have more rooms to walk through. More people to call. More reasons to tell yourself the next quarter will make sense of the last one.
That's part of what makes it dangerous. The problems don't stay contained. A weak decision gets more places to hide. A hard conversation gets passed to another calendar. A founder can stay busy for months while the basic question goes unanswered: why am I building this?
For me, the answer had drifted. I had built the portfolio from a wound connected to being a new dad and being afraid. That was the diagnosis I had to face... no market analysis, no lesson I could hand to a team and move on from.
It was mine.
In a later written reflection, I called the loss chasing the wrong mountain. That phrase still lands because a wrong mountain can have a beautiful view on the way up. It can reward you with admiration. It can keep offering new milestones. You can move fast and still be moving farther from the work that fits you.
I don't mean that building a portfolio is wrong. Plenty of people should build one. The question is more personal than that. Are you building the thing because it belongs to your work, or because you hope it will settle something inside you?
The answer can change. In my experience, it has to be checked again when the business starts moving faster than your ability to stay present with it.
What happened when I stopped editing the story?
A mentor spent a one-on-one day with me and asked for the whole unaltered story. He wanted to know everything I had fucked up.
That question changes the room.
It leaves very little space for a polished explanation. You can't lead with the part where you had good intentions. You can't skip to the lesson. You have to sit with the decisions, the things you saw too late, the things you kept alive because letting go would have made the loss feel more real.
The first version of a failure is often edited for self-protection. We keep the pieces that make us look thoughtful. We call a bad call a timing issue. We describe a choice as complex when the hard part was our unwillingness to stop.
I knew that instinct well. I had been responsible for a lot. I had also been wrong in ways I didn't want to name.
So I went through the story without softening it. The losses. The decisions. The distance between what I was building and what I was capable of leading with care.
There was no prize for doing that. No relief appeared on command. There was only less room to pretend.
...
That matters because a founder can live for a long time inside a story that keeps every option open. It can feel generous, even strategic. It can also make it hard to see what your attention is costing.
The mentor remained important because he didn't let me turn the session into a performance. He didn't give me a fresh way to describe the portfolio. He asked for the version that would make the rest of the day uncomfortable.
Why did I let go of 23 businesses?
After that conversation, I let go of 23 businesses I owned equity in.
It was a year of subtraction. The number is easy to repeat. The decisions weren't.
Each business is more than a line in a portfolio. It holds people, promises, history, and the version of yourself that said yes. Letting go means admitting that a future you pictured won't be the future you live.
Sometimes that's where the grief sits. The money, sure. And also the identity of being someone with many things in motion. I had confused a full calendar with forward movement. I had confused more ownership with more freedom.
The subtraction filter was not a clever operating model. It began with a harder standard: could I tell the unaltered story of why this was still in my life?
If I could not, I had work to do.
I cannot give you a neat inventory of the 23 businesses or claim that every decision followed one perfect rule. The recorded story doesn't offer that, and I won't add it after the fact. What it does show is the turn: I stopped protecting the portfolio as an identity.
That is different from quitting on responsibility. I was still dealing with what I had created. I was still paying back investors and living with the wounds of the past. Subtraction didn't erase the consequences. It gave me fewer places to hide from them.
When you've spent years adding, removal can look passive from the outside. It's not. Often, it asks for more nerve than the original yes.
It requires you to look at a good opportunity and decide it doesn't belong in your life anymore. It asks you to stop making the future prove the past was right. It asks you to choose what you can carry.
For some people, that work becomes a portfolio. For others, it becomes one business with more depth. I had to find my way back toward the work where I could be present, useful, and responsible for the experience I was creating.
What stayed after the subtraction?
I am careful with this part because I don't want to write a tidy ending over a period that had real costs. The loss did not become good because I found language for it. The 23 exits did not turn into a clean before-and-after photo.
What stayed was a different relationship with attention.
I became less interested in building something just because it could be built. I started asking whether the work had room for my actual life, whether I could see the consequences of a decision, and whether I could remain connected to the people affected by it.
Those questions aren't dramatic. They don't create a new announcement. They have helped me notice when an opportunity is asking me to become someone I do not want to be.
The work that fits may still be hard. It may ask you to make decisions that disappoint people. It may ask you to change your mind after you've said yes in public. None of that's a sign that you chose poorly. It is part of holding responsibility with your eyes open.
I wrote more about the patterns behind this kind of choice in The Pattern. The book is for the moments when a strategy looks sound, yet the person carrying it knows something is off.
What did the $10M+ loss buy me?
A loss of this size makes people want a return on the pain. They want a sentence that converts it into a fair trade.
I do not have one.
It changed what I pay attention to. I stopped treating intensity as evidence I was on the right path. I became more suspicious of any ambition that needed me to ignore the people, the decisions, or the fear underneath it.
The money was real. The investor responsibility was real. The businesses were real. So was the part of me that wanted to build a larger story than I could carry.
...
There are still times when I feel the pull toward more. Most founders do. More reach. More ownership. More proof. The old reflex does not disappear because you see it once.
Now I try to meet it with a different question: what would I've to stop seeing in order to say yes to this?
That question has slowed me down in useful ways. It has made some decisions less exciting. It has given other work a chance to become deeper instead of wider.
If you want a place to keep working through those questions, the Momentum newsletter is where I share the decisions, patterns, and changes I am working through in real time.
Where the story ends for now
I lost $10M+ trying to build a portfolio company. Later, I let go of 23 businesses I owned equity in.
I still remember the work of the wind-down. The deals that had to be restructured. The people who had to be let go. The businesses that had to be sold.
No clean line runs between that portfolio and the work I do now. In the middle sits a year of subtraction... and a question from a mentor that I still hear when an opportunity starts to look like an identity.
Tell the whole unaltered story.