The Entrepreneurs' Round Table

08/28/2026

Five words I wrote in my own log on August 17, 2009:

"I am 40 and almost broke."

Not dramatically broke. No repo man, no eviction. Worse than that, in a way — I was fine. Employed, respected, competent. Three careers deep, having rebuilt my whole skillset every time the industry moved: COBOL, then PowerBuilder, then Java.

And I had almost nothing to show for any of it.

Here's what took me years to understand. It wasn't a grit problem. I had grit. I had rebuilt myself from scratch three separate times to stay employable. Nobody works their way out of that with more effort.

It was a mechanics problem. Every dollar I'd ever earned was the same kind of dollar — the kind you trade hours for, the kind taxed hardest, the kind that stops the day you stop.

Three things changed it, and the first one was just this: I stopped measuring how much I earned and started measuring what I owned.

That's the conversation we had at the Round Table last Thursday. We'll be building on it September 24.

TERT21 — Thursday, September 24
⏰ 8:30 AM (newcomers 8:15)
📍 Village Inn — Oldsmar
🔒 INVITE ONLY — you must register to get a seat at the table.
⚠️ 20 seats max · 14 remaining
💲 Free to attend — you order and settle your own breakfast tab. Not eating? A cash contribution for the staff is appreciated. Tip is separate.
🎯 Register and I'll send you the room details:
https://lp.constantcontactpages.com/ev/reg/9v8bufg

08/28/2026

this is one of my favorite one hour meditations to listen to by Mei-lan.

For access to all of my music and videos ad free: https://mei-lan.a...

08/28/2026

Take the lesson, get up and keep moving. Buckle down on your faith, stay focused and stay the course.

08/28/2026

I'm on Instagram as . Install the app to follow my photos and videos. https://www.instagram.com/stevejacksonassociatesllc?igsi=bW9zN2xjYjU2bDF1&utm_source=ig_contact_invite

08/27/2026

Practice being KIND rather than being RIGHT.

Being right causes stress, fear and anxiety.

08/26/2026

Three words nobody taught us.

EARNED. PORTFOLIO. PASSIVE.

There are only three ways money arrives in your life, and most of us were never told the difference.

Earned income is what you trade hours for. Taxed the hardest. Stops the day you stop.
Portfolio income comes from assets you own.
Passive income keeps working while you sleep.

Here's the part that stings: you can be highly paid, highly skilled, three reinventions deep into a career - and still be one layoff away from starting over. Because every dollar you earned died the moment you stopped earning it.

Nobody ever taught me which of the three was building something that outlasted me.

So here is the exercise. Take last year's income. Break it into its sources. Put a letter beside each one - E, P, or passive. Then add it up.

If almost all of it is earned, you are where I was for two decades. That is not a failing grade. It is a starting line, and you cannot start from a position you have not named.

"Earn with your mind, not your time." - Steve "Action" Jackson

We work through this every third Thursday in Oldsmar - twenty people, one table. Get on the list and I'll tell you when the next one is:
https://lp.constantcontactpages.com/su/wBhnQRI/RoundTable

Sign Up Here!

08/25/2026

Twenty-nine seconds inside the room. 🎥

No stage. No lanyards. No thirty people waiting their turn to pitch.

One long table, twenty entrepreneurs, and an agreement made before anybody sits down: the point is your problem, not their business card.

That's the whole format. It's been that for twenty meetings.

TERT21 — Thursday, September 24
⏰ 8:30 AM (newcomers 8:15)
📍 Village Inn — Oldsmar
🔒 INVITE ONLY — you must register to get a seat at the table.
⚠️ 20 seats max · 17 remaining
💲 Free to attend — you order and settle your own breakfast tab. Not eating? A cash contribution for the staff is appreciated. Tip is separate.
🎯 Register and I'll send you the room details:
https://lp.constantcontactpages.com/ev/reg/9v8bufg

08/25/2026

TRANSFORMATIONAL NOT TRANSACTIONAL WHEN IT COMES TO DOING BUSINESS

08/23/2026

YOU CAN NOT WORK
ON A PROBLEM OF WHICH
YOU ARE UNAWARE