I Eavesdropped on a Millionaire For You. Here’s What I Learned.

It wasn’t my fault, okay?

I was tucked away in a dark corner of a cozy Starbucks with a hot Americano. My goal was to disappear into the wall and finish work.

Two men came all the way across the room and plopped down at the very next table. One had short curly hair with a white button-up and jeans, the other a shaved head with glasses and a thoughtful expression.

After only a few minutes, I heard Mr. Curly over the music in my headphones:

“We’ll sell 5 million leotards this year.”

So yeah, I spied on them. Clearly their talk was going to be far more interesting than my current task.

Normally, I would start a conversation with them, but instead I sat quietly and listened to Mr. Curly mentor Mr. Glasses.

Little did he know he’d picked up a new student: Mr. Creepy-Internet-Writer-in-the-Corner.

Curly or Glasses, if you’re reading this — thanks for the insight


1. Curly — “We’ll sell 5 million leotards this year.”

Yes, leotards. The spandex garment that covers gymnasts everywhere.

Mr. Curly had a young niece or cousin or daughter who participated in the sport. He noticed a need. He started a company.

Though he gave the distinct impression he started and sold at least one company before, now those leotards are selling 5 million units, paying his bills, and earning him enough success to meet with strangers at 10:07 on a Wednesday morning.

I learned: The best ideas often don’t come from the Internet. They come from your surroundings.

2. Glasses — “I am so dumb that I am not afraid to navigate a complex talk.”

There was a reason Mr. Glasses was spending an hour on a weekday in a small coffee shop.

He had questions. He was dumb enough to think Mr. Curly might have answers.

I like Mr. Glasses a lot.

How do you navigate a complex talk? How do you deal when you aren’t the smartest person in the room?

You ask questions until you understand.

I learned: Pride will make you afraid. Ask the questions anyway. Mr. Glasses reminded me every time I try to seem smart, I learn nothing. Every time I embrace my stupidity, I learn a lot. Every time I ask “what’s that?” my knowledge bank increases.

3. Glasses — “I don’t understand why people here kind of guard their contacts.”

Me neither, Mr. Glasses. Me neither.

4. Curly — “People don’t realize sometimes the deal doesn’t need to be made.”

In 2016, I said yes to everything.

Start a freelance Snapchat filter business? YES!

Ghost write your book? YES!

Speak at your random event? YES!

Drive across town for coffee at your convenience? YES!

I don’t know why Mr. Curly is sought out by eager learners and I am sucking down a lukewarm coffee taking notes on his conversations, but I imagine one of the biggest reasons is because he has a more definite criteria for what he says “yes” to.

I learned: Saying no isn’t just for bad things. It’s also useful when good opportunities are not the best ones.

5. Glasses — “Do you think that is a good model?”

A good model.

Not “is that a good product?” Not “do you think I can get the right people?” No.

Mr. Curly didn’t ask about products or services or marketing or a logo or a website. He wanted to know about the system. Does it work for the first 100 customers? What about the first 1,000? Can you get paid? Will this business last?

I never figured out exactly what type of business Mr. Glasses was attempting.

Apparently it doesn’t matter.

I learned: Systems beat sweat.

(P.S. I hate that. I hate it because I’m much better at working than I am at thinking. The Internet raised me to be a productivity machine, but blind hustle is only okay if you don’t mind which direction you go.)


My new guru left, leaving me with jumbled thoughts and a quarter cup of cold caffeine.

Two tables over, a woman named Sarah is worried her boss is not happy with her work.

Sarah has at least one child, is in graduate school, and also works full time.

Her friend (whose name I didn’t catch) said this:

“You can’t kill yourself trying to please everyone.”

Thank you, Sarah’s friend.


If you liked this post, you’ll probably also like:

Or, if you’re looking to move from a traditional career to something like Mr. Curly has:

— TB