I grew up stupid, poor, and chubby.

I grew up stupid, poor, and chubby.

Now I’m chilling in a Starbucks, sipping an iced coffee, when my phone blinks with a Slack notification.

Ka-ching.
New client. $5,000.

That’s the third one today. My sales team is on fire. Honestly, I’m a little numb to it at this point, but I still reply with the best Ric Flair GIF I can find.

I’m not trying to brag—this is more of a realization: my life will never be the same.

I’m in a new chapter of my entrepreneurial journey, and I could literally cry.

I’ve started over 23 businesses. Almost all of them failed. And each one, in its own way, left me mentally, physically, or financially wrecked.

I had no choice but to succeed. No rich parents. No handouts. No assistance. No favors.
Just straight hustle—all day, every day.

I told you I grew up stupid. I was even put in special ed back in school.

So how is it that now I’m managing multiple businesses and giving investment advice to very wealthy people? (Not because I want to—but because they’re calling me.)

Let me be honest.

It came down to 4 things:

I don’t need to explain not giving up. If you’re in a rough spot, don’t quit. Just keep swinging.

The crazy part is the people.
Looking back, every leap I made—every breakthrough—came after meeting someone who could change my life... and then helping them or becoming friends with them.

Maybe I’m just a friendly guy. But truthfully? I’m tactical.
I had a learning disability. Couldn’t write. Never read a full book until 8th grade.
So I learned to talk. To connect. To survive.
Then I turned that survival skill into a superpower.

I devoured books like How to Win Friends and Influence People, Sell or Be Sold, and Fanatical Prospecting.

Naturally, I went into sales.
Not the cushy kind—the “if I don’t sell today, I don’t eat” kind.

I sold “art” for a long time (story for another day), but I was broke.
So I had to find rich people who had money to spend.
I went to events, festivals, golf courses, ski resorts, concerts—wherever they were.

I wasn’t a hard-closer.
I was a chameleon. I’d vibe with you, be your buddy… and then close you.

Profit isn’t a bad word. It’s life.

So there I was, young and broke, hanging out with old rich dudes.
Nothing weird—we just liked the same cool stuff and free liquor.

But I asked good questions. I listened.
And I learned.

Then, a couple years later, one of them called me.
He needed help with his booming business.
Boom—now I’m a millionaire.
All because I mastered the skill of meeting people who could change my life.

Before my latest (successful) company, I started a funding business.
We made $1M in 10 months.

But I hated it.

I hated my business partner.
The clients were nightmares.
The team? B-players at best.

We were making money, but spending it just as fast.
Instead of scaling, we were sputtering.

All of it? My fault.
I thought selling money would be where the money was.

I was wrong.

Money is just a tool.
And most people who need money… are bad with money.
Otherwise, they wouldn’t need it.

The whole thing spiraled—debt, chaos, regret.
I shut it down and walked away.

Moral of the story?
Just because a business makes money doesn’t mean it’s a good business.

Impact matters.
Your team matters.
Your time matters.

That business was too complicated.
The finance industry is a mess.
Most of the people I helped just pissed the money away—they had no clue how to leverage it.

Now, after that dumpster fire, I know the ins and outs of how to get funding and use it properly.
But we’ll save that for another time.

I told you that story to say this:
There are easier—and way more lucrative—ways to make money and succeed in business.

To put it bluntly:
My current business is thriving because the market is in pain—and we’re solving that pain.

It’s not some flashy new marketing tactic.
Not AI.
Not crypto.
Not a radical invention.

It’s simple:
People have a problem. I have a solution. They pay good money for it.

In business, you don’t have to be right.
You just have to be successful.

In my next article, I’ll break down what I see as the biggest money-making opportunities in the coming recession—while everyone else goes broke.

Talk to you then.

Robert Lyon
CEO & Founder, The Lion’s Den
Go. Fight. Win.