Estimated Time Reading: 3 minutes

🌟 Editor’s Note:

Welcome back to Behind the Books! A 3-minute read with stories, tools, and lessons from real companies—what worked, what didn’t, and what founders can learn.

🥣 The Story:

Everything was falling apart.

It was 2008. The economy was tanking. Brian Chesky and Joe Gebbia had bills to pay and zero revenue coming in.

Their "air mattress rental" startup? Nobody cared. Fifteen investors said no. Half didn't even reply.

Credit card debt was piling up. $30,000 and counting.

Then came the presidential election.

Instead of another investor pitch, they got creative. Obama O's cereal. Cap'n McCain's. Hand-designed boxes, real cereal inside, $40 each.

Sounds crazy? It worked.

They sold over 1,000 boxes. Made $30,000. Enough to keep the lights on.

But here's the twist: Y Combinator's Paul Graham wasn't impressed by their startup pitch. He was impressed by the cereal.

"If you can convince people to pay $40 for $4 boxes of cereal, maybe, just maybe, you can convince strangers to live with each other."

Airbnb got into Y Combinator.

Today? $75 billion company.

The Lesson:

The cereal wasn't the business. It was proof they wouldn't quit.

In 2025, early-stage investment hit $24 billion — the lowest level in at least five quarters. Meanwhile, AI companies grabbed $100 billion, up 80% from last year.

Translation: If you're not building AI, good luck getting funded.

But here's what hasn't changed since 2008: Investors want to know your business will survive long-term. They're backing founders who prove they'll outlast the "no's."

The Airbnb founders didn't wait for perfect market conditions. They found revenue in the weirdest place possible.

Your version of $40 cereal? That's your competitive advantage right now.

From Behind the Books:

Investors are more selective than ever, committing capital to startups with experienced leadership and compelling, customer-centric solutions.

But resourcefulness still beats a perfect pitch deck.

The market rewards founders who prove they won't give up when everyone else does.

This Week’s Prompt:

What's your cereal box moment?

Not your side hustle. Your proof that you'll find a way when there isn't one.

Maybe it's:

Pre-selling before you build

Manually doing what software will automate

Finding revenue where no one's looking

Execute it this week. Because in tough markets, scrappy beats strategic.

See you next Friday,

– Yan

P.S. Know a founder grinding through this funding winter? Forward this.

Remind them: The best companies aren't built when money flows. They're built when it doesn't.