What Jeff Bezos Taught Me About Staying Hungry: The Day 1 Mindset

Welcome to Peaceful Growth, where you will find actionable tips to grow your agency to $10M (without working overtime).

We just celebrated the 16th anniversary of my agency.

There’s been a lot to be grateful for — some big wins, a few tough moments, and plenty of learning in between.

But lately, I’ve been feeling something different.

Comfort.

When you run a business for this long, things start to feel steady. Predictable. Settled.

And while that sounds like a good thing, it also comes with a hidden danger: you start losing your edge.

That itch to build. That fire to figure things out.
It cools down slowly… quietly.

Then one morning, I’m out on a run listening to a podcast — Lex Fridman interviewing Jeff Bezos.

Jeff drops a line that stops me in my tracks:

“It’s always Day 1.”

He explains that at Amazon, they operate with a Day 1 mindset — because Day 2 is where companies go to die.

Day 2 means getting comfortable.
Following processes blindly.
Slowing down.
Losing touch.

At first, I brushed it off.

I thought, Well, sure. That’s easy to say when you’re running Amazon.
They’ve got billions in the bank, an army of engineers, and rockets in space.

What does any of that have to do with running a small web agency?

But then I went and read his full 2016 shareholder letter.
Slowly. Twice.
(Highly recommend that you read the letter.)

And I realized — some of the most powerful ideas in there weren’t about scale.
They were about mindset.

Because whether you’re a 5-person startup or a 500,000-person giant,
the hardest thing to protect as you grow…
is your hunger.

Startups move fast.
They solve problems in scrappy, clever, creative ways.
They don’t wait. They build.

But as the team grows and the systems mature, something shifts.
Speed turns to process.
Curiosity turns to checklists.
And magic gets replaced by meetings.

That’s the slide into Day 2.
And Jeff’s letter?
It’s a map to stop that from happening.

So here are 13 timeless lessons I pulled from it — rewritten for founders like us.
The ones building web agencies.
The ones who want to stay dangerous.

1. Stay Day 1

Always act like it’s your first year in business.
Eyes wide. Ears open. Heart on fire.

Once you feel like you “made it,”
you’re in trouble.

2. Obsess Over Clients

Don’t just serve your clients — study them.
Anticipate their needs before they speak them.

Your edge isn’t in watching what other agencies are doing.
It’s in deeply understanding what your client really wants next.

3. Play the Long Game

Experiment often.
Most things will fail. A few things will spark.

Protect the sparks. Nurture them.
That’s where real growth happens.

4. Don’t Worship Process

Processes are tools, not commandments.

If a checklist helps — great.
But the moment it slows you down or leads to bad results, toss it.

You run the process. The process doesn’t run you.

5. Feel the Client

Surveys are fine. But they don’t tell the whole story.

Talk to your clients. Meet them in person.
Feel their frustration. See what excites them.

That’s how you build things that actually work.

6. Use Two-Way Doors

Most decisions aren’t final.
They’re two-way doors. You can walk back through.

So move fast. Test. Adjust.
Indecision costs more than mistakes.

7. 70% Info Is Enough

You’ll never have all the info.
If you wait for 100%, you’re late.

Make decisions with 70% confidence.
Course correct if you need to.

8. Disagree and Commit

Your team won’t always agree with you — and that’s okay.

If they believe in something, let them try it.
Even if you’re unsure.

That kind of trust builds speed and ownership.

9. Fast = Fun

Momentum is underrated.

Teams that move fast smile more.
Work gets fun when things ship quickly.

Slow is heavy.
Speed feels like progress.

10. Escalate Fast

If two people aren’t aligned, don’t waste weeks.
Get in a room. Solve it.

Don’t let “who’s more tired” make your decisions.

11. Trust Your Gut

Data is useful — but as a founder, your gut matters more than you think.

You’ve seen things your team hasn’t.
Trust that instinct. It’s earned.

12. Never Get Too Comfortable

Even when clients are happy, they still want more.
They just don’t know it yet.

So keep building.
Keep surprising them.

13. Lead With Heart

At the end of the day, the best work doesn’t come from spreadsheets.

It comes from care. Taste. Curiosity.
Build things you’re proud of.

That’s the real edge.

Final Thought

It’s been 16 years since I started this agency.
But I want year 17 to feel like year 1.

Day 1.

Because Day 1 means you're still in the game.
Still dangerous. Still alive.

And that’s where I want to be.

You too?

Let’s stay Day 1 — together.

[On a totally different note, here’s something I’m excited to share to help you sharpen your copywriting skill as a founder in 2025]

One Skill Every Founder Should Sharpen in 2025

When CD Baby sent a quirky order confirmation email (“...placed on a satin pillow and carried to our private jet…”), customers loved it.
They shared it. It went viral.
That one email helped the small store sell over $100M in music.

Great copy builds trust, creates experiences, and drives sales.
And it’s not just CD Baby—companies like Groupon and Basecamp used writing as their secret weapon.

As founders, we write every day. If our words don’t connect, we lose opportunities.

The good news? Writing is a skill—you can learn it.
If you learn just one skill this year, make it copywriting.

I recommend CopyThat—a 10-day email course that takes just 30 mins a day. It’s worth it.

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One More Thing...

A lot of you have asked about the tools I use to stay productive and grow my agency.

So, I put them all in one place—organized by category:

• Writing Tools ✍️
• Productivity Apps ⏳
• Skills and Courses for Founders 🎓

And more.

You can check them out here.

Hope it helps! 🚀