What Grief Can Teach You About Building Again

C.S. Lewis is best known for Narnia.

For wonder. Whimsy. Imagination.

A writer who gave us fauns, wardrobes, and magic-laced allegories.

But A Grief Observed?

That book is something else entirely.

It’s not light.

It’s not metaphor.

It’s the raw, unedited journal of a man undone by loss.

When Lewis’s wife Joy died, he didn’t write a memoir.

He documented the disintegration of belief.

The death not just of a loved one—but of a version of himself.

And when I read it—

I didn’t just think about grief.

I thought about founders.

Specifically, second-time founders like you.

Because what he wrote in the wake of personal loss…

echoes what I hear in the voices of those who have lost companies, teams, movements, dreams.

Grief, it turns out, is the real first round of funding.

You’ve built before.

You’ve pitched, shipped, scaled—or tried to.

You’ve rallied teams, raised capital, run out of time.

And when it ended—whatever “ending” looked like—

you didn’t just walk away with lessons.

You walked away with loss.

• Loss of identity.

• Loss of faith in your instincts.

• Loss of the belief that the next build would be easier.

But here you are again.

Building.

Not from scratch—

from scar.

What Grief Teaches Us About Category Creation

Grief doesn’t just strip you down.

It demands redefinition.

Of meaning. Of purpose. Of what’s worth fighting for.

And that’s what category creation really is:

• It’s not just differentiating.

• It’s not just positioning.

• It’s reorienting the world around a deeper truth.

You can’t fake that.

And grief? Grief is the ultimate bullshit killer.

You can’t walk through loss and come out pitching like before.

You stop selling problems.

You start standing for people.

You realize:

Movement marketing isn’t strategy. It’s surrender.

Here’s What Grief Gives Founders Like You:

1. Conviction without pretense

You’ve already failed publicly. You survived.

You don’t need to prove anything—you’re here to build what matters.

2. Clarity that cuts through the noise

Grief sharpens your voice.

You stop trying to impress. You start trying to serve.

3. The courage to create a new category—not chase a crowded one

You’ve seen what happens when you play someone else’s game.

Now you get to name your own.

So if you’re here, second-timer—

Building again.

But not for headlines.

For healing.

For truth.

For the people who need what only you can now create—

I want you to know:

You’re not behind.

You’re not broken.

You’re becoming.

What felt like the end of the road?

Was the start of your category.

Your grief was a gateway.

Your build is the movement.

And this time, it’s not hype.

It’s holy.

And you’re not alone.

Just look at them:

Ben Horowitz

Failed with his first venture-backed startup, Loudcloud. But through the fire, he didn’t just pivot—he co-founded Andreessen Horowitz and reshaped the VC game. His book, The Hard Thing About Hard Things, is a grief journal in disguise. A war story for builders who’ve bled.

Brian Chesky

Airbnb was rejected by dozens of investors. During the 2008 recession, they sold cereal boxes to survive. What looked like a joke? Became a movement around belonging. That’s not just hospitality—it’s category design through lived suffering.

Whitney Wolfe Herd

Left Tinder after a very public breakup and legal battle. She didn’t just launch another dating app—she created the category of female-first social networking with Bumble. Her grief turned into a reframe: what if women made the first move?

Amanda Goetz

Went through divorce, grief, burnout. Then built House of Wise—a movement, not just a wellness brand. Her entire GTM was truth as strategy. She built trust because she didn’t hide the pain. She named it.

This is what second-time founders have that first-timers don’t:

• Scar tissue

• Soul compass

• A story with weight

Your grief?

It’s not a liability.

It’s your moat.

And the movement you’re about to build?

Won’t be “category-defining.”

It’ll be category-redeeming.

Because this time,

you’re not chasing hype.

You’re honoring truth.

So here’s our message to fellow second-timers:

Your first company didn’t fail you—it forged you.

Your grief? That was sacred R&D.

And this time,

you don’t have to build fast.

You just have to build true.

If that feels like your story,

this newsletter’s for you.

Not to teach you anything.

But to remind you—

You already know.