The Briefcase Mindset
Why analog structure is a competitive advantage in an AI world
Miles said it like a joke, but it landed like a truth.
“Man, you’re out here doing Rolodex and briefcase stuff.”
He wasn’t wrong.
The more I build with Stresswood, the more I find myself reaching for tools most people abandoned decades ago. Not for nostalgia, but because those tools solved problems we still haven’t solved well. Problems the modern stack actually made worse. Problems about memory, relationships, and navigating complexity when information is scattered across spaces that never talk to each other.
You’d think AI would make all this easier. In reality, it exposed the gap.
Because the farther I go into this industry, the clearer the lesson becomes: memory is strategy. And the people who master what they remember, how they recall it, and when they surface it, win.
That’s why I keep circling back to analog structure.
Not as an aesthetic.
As a system.
What the briefcase actually was
Most folks imagine a leather box with papers. But the best operators treated their briefcases like portable mission control. Inside you’d find:
Active dossiers for every live deal or negotiation
One-page relationship cheat sheets
A-list priority lists
Handwritten notes that carried context algorithms can’t
Term sheets, envelopes, notecards for immediate follow-up
A reading stack curated with intent
Everything inside served one purpose:
Never walk into a conversation unprepared.
A briefcase was the original integrated app. A single place where context, relationships, and decisions lived together. The modern stack scattered those elements into twelve different tools, each with its own logic, tags, and black holes.
We gained speed but lost coherence.
We gained scale but lost structure.
The Rolodex wasn’t a contact list. It was a worldview.
The most powerful operators didn’t use their Rolodex to look people up.
They used it to think.
The Rolodex forced curation.
It forced tagging.
It forced you to choose who mattered.
Flipping through it created peripheral vision you don’t get from a screen. You’d notice patterns. You’d reconnect dots you forgot about. You’d realize someone belonged in the next room with you.
And here’s the deeper insight:
The Rolodex solved Dunbar’s Number not by expanding memory but by structuring it.
It turned scattered social capital into a navigable map.
Modern tools atomized that map.
Everything lives somewhere, but nothing lives together.
So we scroll instead of recall.
We search instead of connect.
We transact instead of deepen.
Analog wasn’t slower. It was richer.
When I say I want to build “the most analog VC firm in the industry,” people think I’m joking. But what I’m actually trying to rebuild is the human OS the industry lost along the way.
Because the best investors aren’t the ones who know the most people.
They’re the ones who remember who matters, why it matters, and when to move.
AI gave us infinite storage but no unified memory.
Infinite contacts but no intuition of who belongs together.
Infinite data but no natural recall.
Analog structure gave operators a rhythm.
A cadence.
A way to pull the entire map of their relationships, opportunities, and commitments into a single place.
That’s the missing piece today.
Bringing it back to life
I’m building Stresswood around that idea. A firm that treats memory, context, and relational intelligence as first-order strategy. A firm that operates not by reactively scrolling, but by proactively remembering.
I’m also looking to partner with organizations and applications that want to recreate this operating system for the modern world. Not copying the old tools, but honoring the physics behind them:
Context lives best when it lives together.
Relationships deepen when they’re curated, not hoarded.
Preparation is a power move.
Recall is leverage.
And the human brain still sets the ceiling on every firm’s performance.
In a noisy market, the firms with the deepest memory win.
Because memory drives trust.
And trust drives deal flow, distribution, and outcomes.
Takeaways
The briefcase and Rolodex weren’t artifacts. They were systems for coherence.
Analog structure made people more prepared, more relational, and more strategic.
Modern tools scattered what great operators kept together.
Rebuilding that unity is the next frontier of venture performance.
Invitation
Look at the tools you use daily. Are they helping you remember, or making you forget?
Are they helping you connect, or scattering your map?
That question might be the most important diligence you can run on your own operating system.
~e