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Pre-Purgatory

Shoutout to Ani, who’s facing this exact problem, for inspiring this edition*

Let’s talk about the hardest part of starting a startup:
Starting.

Not the pitch deck.
Not fundraising.
Not product-market fit.

Just getting sooomething going in the first place.

In martial arts, we say the hardest belt to get is the white belt.

Before you ever build, you’re stuck in a mental loop that sounds like this:

• I want to start something... but I have a full-time job.

• I could quit... but that’s scary and I need to eat.

• I’ve got a bunch of cool ideas... but not enough time to explore them all.

• I want to work with other people... but I don’t know who’s serious.

• And even if I had an idea and a team... I wouldn’t have time to learn the things I don’t know.

This is not laziness.
This is not self-sabotage.
This is not procrastination.

This is your brain buying time.
Time to make sense of the stakes.
Time to believe you’re allowed to try.

If anything, feeling this internalized, self-induced pressure (anxiety?) is a sign that you’ll be a good founder.

Let’s unpack this.

Chicken or Egg (or Existential Spiral)

Great question. The answer is both. But in sequence.

Start by exploring ideas deliberately, not randomly. Give yourself 1–2 weeks per idea. Treat it like speed dating.

Ask:

• Can I prototype this without quitting my job?

• Would I be excited to work on this for 3 years even if it fails?

• Who else might genuinely care about this?

Then commit to one for a 30-day sprint.
Not forever. Just enough to test if it has legs.

The mistake most people make is they dabble in five ideas at once for five months and none of them get any momentum. (I’m guilty of this).

Cracked ≠ Cofounder

It’s cool that your friends are smart. You probably want to work with them.

But intelligence ≠ commitment.

If they say “I’m down” and then ghost, they’re not cofounder material. They’re party guests, aka they want the energy but not the commitment.

Look for people who show up consistently, even when it’s boring. People who give thoughtful feedback. People who’re there through the highs and the lows.

If you don’t have those people yet, that’s okay.

Most people don’t meet their cofounders through a pitch. They meet them through momentum.

Start building publicly, not performatively. Share your progress. Write about what’s hard. Talk through your tradeoffs.

The part most people miss: Cofounders aren’t discovered.
They’re revealed by what they choose to show up for.

No Time. No Expertise. No Excuses.

You’re busy. I get it.

Welcome to being a founder.

You don’t need to know everything. You just need to:

• Know what you don’t know

• Ask for help publicly

• Prioritize like hell (time is your real cofounder right now)

Momentum compounds. Indecision doesn’t.

No one feels ready when they start. That’s why they start.

*I wouldn’t have written this without Ani. If you reply with a note of encouragement, I’ll send them all to him. Let’s give him the push he needs.

That’s all for now,

BTW — The Cherrytree cofounder community is now open. Join here →

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