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Before Day 101

There’s something magical about the first 100:

• The first 100 users of your product.

• The first 100 rejections you face.

• The first 100 followers you get.

• The first 100 dollars you make.

• The first 100 hours you spend.

The first 100 days set the tone for your cofoundership.

Shoutout to Luke Haythorpe, one of our community leaders, for coining this.

It’s also where most people go wrong.

Here’s how to avoid the avoidable — and what happens when you do.

Agreement ≠ Alignment

You both say you want to “build fast.” Sounds aligned.

But one of you means scrappy prototypes to test ideas fast.
The other means scaling infrastructure early to avoid tech debt.

You’re both being “relentlessly resourceful.” In opposite directions.

Day 27, one of you is trying to duct tape an MVP.
The other is deep in AWS configs.

Now you’re out of sync, frustrated, and burning time.

Early on, alignment > agreement. Talk through what your words actually mean.

Build the Bond like the Business

YC says “do things that don’t scale.”

In product, that means hand-onboarding your first 10 users.

In cofoundership it means:

• Weekly 1:1s even when “there’s nothing urgent”

• Debriefs after tense meetings (“How did that feel to you?”)

• Sharing what’s not working before it festers

Example:

You just spent 60 hours together grinding out a launch.

But you’re quietly resenting how they handled a bug fix or spoke to the designer.

You don’t bring it up because “it’s not a big deal.”

Wrong.

Early silence scales into resentment.

Talk now, when it’s small. That’s how you build a relationship that does scale.

Decide Fast, Not Last

You’ll be shocked by how emotional things get (especially if you’re a 1st time founder).

You’ll feel it in the first 100 days when:

• A close friend applies for a role but you know they’re not a fit

• One of you wants to hire fast and the other wants to wait until post-funding

• You disagree on how to handle your first refund request or churned user

Example:

Day 42. Your cofounder says, “Let’s just keep them on the team. We’ll figure it out.”

You know it’s a delay tactic.

You also know avoiding the conversation now means a much messier one in 3 weeks.

Make the hard call.

It’s not ruthless, it’s rigorous. There’s a difference.

The Magic of Getting It Right

There’s something undeniably transformative about the first 100 days of cofoundership.

Yes, you’re figuring out how to build a product or service together, but also figuring out how to think together.

You’re sharing a to-do list a tempo.

You catch each other’s thoughts mid-sentence.

You start speaking in shorthand.

The late nights feel lighter. Not because the work got easier, but because you’re carrying it together.

It’s the difference between being “stuck together” and being “in it together.”

The startup is only as strong as the relationship that underpins it.

Great companies start with great company.

That’s all for now,

BTW — Grab yourself some dumbfound coffee. Our grind fuels yours.

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