How Many Cookies Does It Take To Pay The Rent?

I’ve got this habit.
I’ve been doing it since I was about eight years old.
Anytime I walk down a street, past a café, dry cleaner, cookie shop, I don’t just glance at the sign and keep on moving.

I start running numbers in my head.

Alright, how many cookies can they sell a day?
What do they charge? What’s the margin after ingredients? After labor, rent, electric, insurance?
What are they paying themselves?
And if they are… are they happy?

Let’s say they move 200 cookies a day at $3 a pop. That’s $600 in sales.
If each cookie costs $1 in ingredients, and after rent, labor, and insurance, they’re left with a $1 profit per cookie, that’s $200 a day.
Six days a week, that’s $1,200 a week. $5,000 a month. $65K, maybe $70K a year.

So the next question is… is that enough?

Not for me. But maybe for them.
If they love baking, if they light up every time someone bites into their grandmother’s recipe, and if that $70K funds the life they want?
That’s the American Dream.

Not the Silicon Valley dream.
Not the money-changers' dream.
Not the crypto-to-the-moon dream.
But the real one, the kind where your soul and your spreadsheets are both in the green.

Now let’s contrast that with a business I just spent 24 hours inside of:

The MGM Casino in Springfield, Massachusetts.

Massive building. Fancy lights. Slot machines are humming.
And somehow… a total customer disaster. It literally just stunk of desperation.

If I were the Chief Operating Officer of that place?
I’d have fired myself before check-in.

Let’s start with the room.

It smelled.
Not like a bit of mildew.
It smelled like someone had died in there, and the crime scene got half-covered in Febreze.

The ceiling was raw concrete. Like they gave up halfway through construction and said,
“You know what? Let’s roll with the parking garage aesthetic. That’s edgy.”

Luckily, my boy Timmy, who runs the hotel at UMass, got us moved.
A little less crime scene. Still heavy on the Febreze and depression.

But that was just the beginning.
Because here’s the truth: the whole place stunk of mismanagement and desperation.

This business is designed to take your money. That’s the model.
Create an experience compelling enough that you voluntarily empty your pockets for a chance at a jackpot.

Except these geniuses… filled the whole place with friction.

Security guards couldn’t answer basic questions.
Every entrance was locked after midnight.
I went out for a smoke at 1 AM. Tried to get back in, door locked, not just that door but every single one of the 60 glass doors that line the entire place, the Main Entrance in the front, all locked!?!? The only way in to the joint was through the fucking parking garage, and not a single sign on any of the more obvious doors telling that to the desperate souls trying to get in and drop a mortgage payment. .

It took me almost a full mile, according to my Apple Health app, to find the one door in the parking garage still open.

If I wasn’t staying there, I would’ve assumed the place was closed and left with my wallet fully intact.

So think about this:
Your business is literally designed to siphon money from people; that's your whole business model, and you’re making it hard to enter? Fire that COO…

Now it’s time for dinner.
I’m on a carnivore diet. I need 4,000 calories of meat a day.
So we go looking for the steakhouse.

Guess what?
Closed.

Not just on Sundays, closed Sunday through Wednesday.
Apparently, the cows take a four-day Sabbath in Springfield.

So we wander downtown and finally hit up the spot everyone recommended: Max’s Tavern.

And let me tell you, night and day.
The Bartender was friendly. Sharp. The food was awesome.
And within 10 minutes, Timmy and I had the whole bar talking loudly with each other like long-lost classmates at the 25th reunion.

Red Sox World Series, Patriots Super Bowls,. UMass Final Four memories.
For shits and giggles throw in a drunk truck driver from Texas easily blowing a 2.3 giving us his unique and well crafted philosophy on his preference for dating women during menopause. You’ll have to use your imagination, as it is even a little over the edge for me to repeat, and that right there is saying a hell of a lot!

But here’s the kicker…
Max’s Tavern is actually in the BasketBall Hall of Fame??!!

I guess the Basketball Hall of Fame is struggling so badly that they had to renovate and lease out half the building to form a strip mall.

As a kid, I remember walking up to the Hall and thinking, “This is the mecca.”
Now it looks like Route 9 in Framingham.

You want to learn about Bill Russell and each of his 11 rings? Tough luck.
Want to see film clips of the 86 Celtics or the 90’s Bulls?
Sorry, we had to supplement our revenue so that section’s now a Cold Stone Creamery.

This is the NBA Hall of Fame.
The second most popular sport in America.
And they couldn’t figure out how to market and sell it enough to keep the doors open, fucking sad but true.

Bad operations? Bad marketing? No customer experience?
You end up leasing out Larry Bird’s legacy for a burger joint.

We walk back to the MGM.
Still locked doors.
Still dead energy.

So I turn to Timmy and say, “Let’s hit the poker room.”
He doesn’t even play, but I tell him, “I know it’s the only place we’ll have fun in this rathole, I guarantee it”.

And just like always, the room with the felt never disappoints.

Four or five tables. Midnight. All grinders.
Guys who’ve been waiting all day for someone like us to sit down, or so they thought.

But poker? Half the joy of a poker table is the characters and the storytelling.
And this room delivered.

We start trading stories, UMass basketball, Marcus Camby, and the Final Four run.
Some guy from another table stands up and rants about losing a bet on Derek Kellogg missing a free throw in the ‘90s.
Still bitter. Still hilarious.

That’s the curse of betting on your own team:
Sometimes they win, and you still lose.

So what’s the real takeaway here?

If you’re building or running a business, any business, ask yourself three things:

1. Is it making the money you need?
Not theoretical money. Not investor pitch deck money.
Not private equity shoot-to-the-moon money.
Real, food-on-the-table, feed your family, pay-your-bills money.

2. Is your customer experience aligned?
Are your people, your systems, your signage, shit even your doors helping people do business with you?
Or are they throwing up friction at every turn?

3. And most importantly, does it feed your soul?
Because if it doesn’t, what the hell are we doing here?

If your business pays your bills but steals your joy? That’s a slow, painful jail sentence.
If it feeds your passion but can’t cover rent? That’s just a hobby with overhead.

The sweet spot is rare.
But when you find it, money, experience, and meaning. that’s the Holy Fucking Trinity right there!

If this hits home, reply and tell me about your own “cookie store” dreams or moments.
Or send it to someone who needs to hear it.

We’re all doing the math in our heads.
But sometimes, it’s not about how many cookies you sell.
It’s about the kind of life those cookies fund, and whether that life actually tastes delicious.