4 Hats Every Founder Should Learn to Wear
Welcome to Peaceful Growth, where you will find actionable tips to grow your agency to $5M (without working overtime).
It’s been a busy few weeks.
The start of a new year and quarter always brings a lots of planning and focus time.
Lately, I’ve been spending a big chunk of my time setting quarterly priorities with my teams—Sales, Marketing, Account Management, etc. (Translation: juggling a hundred things while trying not to drop the ball!)
But next week, I’m hitting pause.
I’m heading to Atlanta for my first “Growth Trip” of this year.
A week of reading.
A week of thinking.
A week of reflecting on the big decisions that shape my business and life.
(If you don't know about my Growth Trips, check this out)
This issue is probably the shortest.
But it’s one of the most powerful lessons I’ve learned as a founder from the book — The Road Less Stupid.
(If you can/want to read only one business book this year, I would make it to this one).
In the early days of your business, you wear all the hats.
The Artist—fueling ideas and creativity.
The Operator—handling the daily grind.
The Owner—planning for growth.
The Board—assessing risks and investments.
It’s exhausting. It’s overwhelming.
Success isn’t luck—it’s learning to wear the right hat at the right time.
Take Steve Jobs for example.
He was a visionary Artist—one of the best.
But Apple only became Apple because he learned to wear the Operator, Owner, and Board hats too.
His real genius wasn’t just creating—it was building a team that balanced each role.
(Imagine if Jobs only focused on design and ignored cash flow… Apple might have stayed a dream!)
If McDonald’s were run by an Artist, the management team would spend all their time obsessing over creating a healthier, better-tasting cheeseburger.
Clearly, the McDonald’s Artist hat was abandoned years ago! Instead, they wear the Operator and Owner hats, optimizing systems and scaling profits globally.
Many founders get stuck here.
They cling to their favorite hat.
The Artist avoids numbers.
The Operator avoids strategy.
And that’s exactly where businesses fail.
Wearing the wrong hat at the wrong time leads to chaos.
Trying to create while ignoring risks? Disaster.
Making decisions without understanding cash flow? Nightmare.
Here’s the good news:
Each hat represents a mindset.
And mindsets can be learned.
You can be an Artist and learn to read a balance sheet.
You can be an Operator and delegate effectively.
You can master them all.
Here’s the bottom line:
Growth and control work inversely. The more growth you desire, the less control you can have (and vice versa).
[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]
How a simple email made millions for this small business (real story)
When CD Baby, a small online music store, sent its now-famous welcome email, something magical happened.
It wasn’t just a boring “thanks for your order” message. It was fun, quirky, and personal:
“Your CD has been gently taken from our CD Baby shelves with sterilized, gloves, placed on a satin pillow, and is now being carried to our private jet…”
Customers loved it.
They shared it.
It went viral.
That playful email helped transform a small indie store into a company that sold over $100 million in music (Google it).
Why? Because great writing sticks.
It creates experiences, builds trust, and drives sales.
Not just CD Baby—companies like Groupon and Basecamp have built their success on great copywriting. It’s a 24/7 sales rep that never sleeps.
As founders, we write every day—pitches, emails, job posts, tweets. But if our words don’t connect, we lose deals, customers, and time.
Here’s a good news: WRITING IS A SKILL. You don’t “have it”, you learn it.
If you can learn only one new skill in 2025, make it writing.
I’ve spent over $10,000 on writing courses, and out of all of them, I highly recommend CopyThat—an email-based copywriting course you can complete in just 30 minutes a day for 10 days.
Check it out here: CopyThat
That’s all for now—see you in the next issue!
— Anil Gupta
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In Case You Missed It
By the way, in my last issue, I shared “Lessons from $15M Domain Deal, The Money Ladder, Startup 101, and Why Founders Need Newsletters”
In this issue, you'll learn:
- Story: Why the founder of HubSpot bought Chat.com for $15M (and sold it to OpenAI)
- LinkedIn Post: The Money Ladder – $100K → $1B
- Video: Startup 101: build (and scale) a multi-million dollar business
- Podcast: Why every founder should have an email newsletter
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