“Nothing’s ever free.”
That was one of the first comments after I announced our next free business seminar.
Honestly…
I didn’t get defensive.
I understood it.
We’ve all seen the free webinar that ends with a $2,000 course.
The “free” consultation that’s really a sales appointment.
The ebook that’s only there to collect your email.
After enough experiences like that, “everyone’s got an angle” starts feeling less like cynicism and more like common sense.
The comment didn’t make me think about seminars.
It made me think about a question I’ve been wrestling with for almost twenty years.
What’s the right way to help people?
Nobody Helped Me
When I started my first company, nobody handed me a roadmap.
There wasn’t a mentor I could call when payroll was due.
No one explained taxes.
Pricing.
Marketing.
Hiring.
Operations.
Every lesson came after making the mistake first.
I remember thinking,
There has to be a better way than this.
That feeling never really left me.
The Moment Business Stopped Feeling Like Enough
While running that company, my days were unusual.
During the day I worked on cars worth $400,000 to over a million dollars.
At night I was reading When Helping Hurts and watching documentaries like Poverty, Inc.
I couldn’t shake a question.
Why do so many well-intentioned efforts fail to actually help people?
One moment still sticks with me.
A customer’s vehicle was delayed by a day because one of our machines was down.
I’d personally driven him home.
We’d treated him well.
He broke down crying.
Over time I began noticing something that bothered me.
People often attached extraordinary emotion to things that ultimately weren’t the things that mattered most.
It left me wondering if business was really where I belonged.
I remember telling a friend I was thinking about walking away.
He looked at me and said something I’ll never forget.
“You can’t change the world sitting on a street corner with a sign. But you might be able to by pulling up to the boardroom in a Ferrari.”
Whether you agree with that sentence or not…
It changed me.
Maybe business wasn’t the obstacle.
Maybe it was the vehicle.
Learning How to Help
After I sold that company, I spent years doing pro bono consulting.
No invoices.
No contracts.
No expectation that anyone would ever become a client.
I simply wanted to become the person I wished I’d had.
I taught seminars on accounting.
Marketing.
Operations.
Technology.
I’d walk into struggling businesses and often recognize problems because I’d spent a year solving them in my own company years earlier.
People constantly told me,
“You make that sound so simple.”
It wasn’t simple when I lived it.
It became simple because experience has a way of removing unnecessary complexity.
Helping Isn’t as Simple as I Thought
I also learned something uncomfortable.
Helping people is hard.
Some entrepreneurs completely transformed their businesses.
Others never took the first step.
Some competitors attended seminars, copied the systems I shared, and sold them for thousands of dollars.
At first that frustrated me.
Eventually I realized something.
Giving information isn’t the same as helping.
Helping well is a skill.
One I’m still trying to learn.
Twenty-One Steps
As I worked with more entrepreneurs, I noticed another pattern.
Most people weren’t afraid of hard work.
They were afraid of the unknown.
Starting a business felt surrounded by imaginary red tape.
So I created a framework called 21 steps to opening a business link below
Everything You Need To Know For Starting A Small Business
It was simply the roadmap I wished someone had handed me.
I reached out to cities.
Universities.
Business organizations.
I offered to teach it for free.
Every one of them turned me down.
Looking back…
I’m grateful.
If someone else had opened the door, Glaive might never have existed.
Instead of waiting for permission, we built the place ourselves.
Today people walk into Glaive every week with questions about LLCs, taxes, technology, marketing, operations—or simply because they don’t know where to start.
Sometimes all people really need is someone willing to answer the first question.
“When’s the Sales Pitch?”
One seminar has stayed with me ever since.
Before I even started, a man in the back asked,
“So… when’s the sales pitch?”
“There isn’t one.”
About halfway through he came back.
“No seriously… when are you going to sell us something?”
“There isn’t one.”
By the end he was the last person waiting.
He threw his hands in the air.
Almost frustrated.
“I don’t understand! Why would you do this?”
I stood there for a second.
I didn’t have a clever answer.
I just remembered what it felt like to build my first business with no one to call.
That conversation has stayed with me.
Not because I convinced him.
Because it reminded me how much trust we’ve lost.
The Question I’m Still Wrestling With
If I’m being honest…
There’s another question I think about a lot.
I’ve set out to build Glaive into a billion-dollar company.
Sometimes I wonder if I’m doing it wrong.
I could charge for every seminar.
Every office hour.
Every conversation.
We’d almost certainly make more money.
Maybe we’d grow faster.
I honestly don’t know.
But if our mission is to level the playing field for entrepreneurs…
Then not every decision can be measured by this quarter’s revenue.
Maybe one day we’ll charge for things we currently don’t.
If that day comes, we’ll be honest about it.
No bait and switch.
No pretending something is free when it isn’t.
Because I don’t think the problem is charging.
I think the problem is pretending you’re not.
What I Believe Today
The older I get, the less convinced I am that the hardest part is building a business.
I think the harder challenge is learning how to help people the right way.
I’m still learning.
Maybe this philosophy costs us money.
Maybe it slows us down.
I honestly don’t know.
But I’m willing to bet my career on one idea.
The world still wants to support businesses that genuinely try to make it better.
Maybe that’s naïve.
Maybe it isn’t.
I guess time will tell.
