2025 Annual Letter
2025 was not a year of outcomes.
It was a year of identity.
From the outside, it probably looked like more of the same: businesses, deals, models, plans, spreadsheets, ambition. But internally, this year felt like a slow, uncomfortable shedding - of certainty, of labels, of old motivations that once worked perfectly and suddenly didn’t.
I entered 2025 as a business operator who invested.
I’m leaving it as an investor who understands business deeply - and that distinction matters more than I expected.
The Early-Year Tension: Success That Didn’t Feel Settled
At the start of the year, I was objectively “winning.”
I had cash flow.
I had leverage.
I had access to deals, people, rooms.
I had proof - real proof - that I could build, buy, and scale businesses.
And yet, there was a persistent hum beneath everything: Is this the game I actually want to play for the next 20 years?
That question kept showing up in different disguises.
Should I double down on Fortress and scale it aggressively?
Should I build a buying group into a massive, durable machine?
Should I roll up HVAC, uniforms, waste, construction supply - pick one and go all-in?
Should I keep operating at all, or am I just delaying the inevitable transition into capital allocation?
None of these paths were wrong. That was the problem.
The Addiction to Optionality
If I’m honest, the first half of 2025 was marked by intellectual restlessness disguised as strategy.
I explored:
Embroidery and uniform roll-ups
Buying groups
Private equity–style SMB acquisitions
Public market value investing
Credit
Hybrid holdco models
Brad Jacobs–style roll-ups
Buffett/Pabrai/Sleep frameworks
“Permanent equity” narratives
Even moonshots and billion-dollar clones
Each one had logic.
Each one could work.
Each one let me stay uncommitted.
I told myself I was being thoughtful.
In reality, I was protecting optionality because committing meant closing doors, and closing doors meant confronting something deeper:
Who am I when I’m no longer building businesses to prove I’m dangerous?
The Inner vs. Outer Scorecard Became Real
I’ve known the concept of inner vs. outer scorecard for years.
In 2025, I finally felt it.
The outer scorecard said:
More revenue
Bigger platforms
Louder wins
Faster scale
More visible success
The inner scorecard asked quieter, more uncomfortable questions:
Do I enjoy my days?
Am I calm when nothing urgent is happening?
Would I still do this if no one ever applauded it?
If I already had “enough,” would this still be the game?
Business, I realized, had become a high-functioning identity.
It fed my competitiveness, my intensity, my need to win.
It also quietly demanded constant attention, people management, and emotional energy I no longer wanted to give indefinitely.
Investing, by contrast, felt different:
Solitary
Quiet
Unforgiving
Clean
There’s no charisma in a balance sheet.
No dopamine hit from reading.
Just truth.
That scared me - and attracted me.
The Middle of the Year: Friction, Fatigue, and Self-Honesty
Mid-2025 was hard.
Not externally. Internally.
I felt:
Mentally crowded
Slightly unmotivated
Less impressed by “big” opportunities
Increasingly allergic to obligation for obligation’s sake
I also noticed something telling:
When I had free time, I didn’t fantasize about building bigger companies.
I read.
I modeled.
I studied businesses I didn’t own.
I thought about capital allocation, not operations.
That was data.
At the same time, I had to confront an uncomfortable truth:
I didn’t yet deserve to fully call myself an investor.
I had conviction, frameworks, taste - but not a long, clean track record.
So the year became about alignment before acceleration.
Not “What makes the most money fastest?”
But:
What path can I walk for 20–30 years without burning out, lying to myself, or needing applause?
Letting Go of the Fantasy Versions
One of the most important (and quiet) wins of 2025 was letting go of fantasy identities:
The guy who builds a $1B operating company just to prove he can
The roll-up emperor
The perpetual dealmaker
The “I could if I wanted to” version of myself
I realized that capability is not obligation.
Just because I can build businesses doesn’t mean I’m required to spend my best decades doing so.
That reframing created space.
Where I Ended the Year
I didn’t end 2025 with a single dramatic decision.
I ended it with clarity.
I want freedom more than domination
I value calm more than speed
I enjoy being right quietly more than winning loudly
I want a life where capital compounds without constant supervision
I want my work to feel like thinking, not managing
Business remains a tool.
Cash flow remains useful.
But investing is becoming the center of gravity, not the side project.
The goal is no longer to prove anything.
The goal is to build a life where:
My time is clean
My attention is focused
My incentives are aligned
My days feel intentional
My capital works harder than I do
The Real Shift
If I had to summarize 2025 in one sentence:
I stopped trying to win every game and started choosing which games were worthy of a lifetime.
That shift doesn’t show up on a P&L.
But it changes everything.
I’ve entered 2026 lighter, calmer, and more deliberate.
Less noise.
More truth.
Fewer bets.
Deeper conviction.
That’s the work.
- Matt
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