The Entrepreneurs' Round Table

10/08/2026

Most people buy real estate on emotion — and find out the truth one repair bill at a time.

On Thursday, Oct 22, at The Entrepreneurs' Round Table, I'm teaching the 4-step napkin test I've used across 350+ houses: Income, Expense, Cash Flow, Cash on Cash.

Four numbers, one page — the deal proves itself or it doesn't.

This is NOT networking — it's a working mastermind.

TERT22 — Thursday, October 22
⏰ 8:30 AM (newcomers 8:15)
📍 Village Inn — Oldsmar, FL
🔒 INVITE ONLY — you must register to get a seat at the table.
🎯 Register and I'll send you the room details:
https://stevejacksonassociates.com/tert/register

10/05/2026

Good brain food!

Dr Joe Dispenza is an international lecturer, researcher, corporate...

10/04/2026

Nobody who designed this is around to walk you through why it still stands. It doesn't matter. It still stands, and people still study how.

That's the highest compliment a system can earn — not "it worked," but "it kept working after the person who built it was gone."

Most of us build businesses that don't pass that test. Take the owner out for two weeks and watch what happens to the calendar, the follow-ups, the quality control. That's not a business yet. That's a very sophisticated to-do list with the owner as the only person who can read it.

Sunday night is a good time to ask the uncomfortable version of the question: if you disappeared for a month starting tomorrow, what in your business would still be standing when you got back?

"It never gets easier. You handle harder better."
— Steve "Action" Jackson

October 22 is the next Round Table — Village Inn, Oldsmar, same table. Topic and registration land as soon as they're locked. Join the list here: https://lp.constantcontactpages.com/su/wBhnQRI/RoundTable — you'll be first to know.

10/03/2026

A member who's been coming to the table for a while told me what actually stuck from one of my stories — and it wasn't the deal. It was the moment right before it.

"The story about you sitting in your truck crunching the numbers and writing out the contract, and then another investor went in and bought the house. It really showed the importance of taking action and not waiting too long because opportunities can pass you by."
— Amanda Durso

I tell that story on myself, not as a brag. I was sitting in a truck, doing the math right, being careful — and somebody else walked in while I was still checking my work and wrote the offer. The lesson isn't "move recklessly." It's that there's a difference between being thorough and being slow, and most of us don't notice we've crossed from one into the other until the house is gone.

Same lesson runs through every business, not just real estate. The proposal you're still "polishing." The hire you're still "thinking about." The price increase you've been meaning to send for three months. Somewhere, someone less careful than you is moving on the exact thing you're still perfecting.

"On the other side of fear lies opportunity."
— Steve "Action" Jackson

What's the thing you've been crunching the numbers on a little too long?

Not on the TERT list yet? Join here — it takes 30 seconds: https://lp.constantcontactpages.com/su/wBhnQRI/RoundTable

Sign Up Here!

10/02/2026

At a recent workshop I ran an exercise that looks like a party trick and teaches a real lesson.

Round 1 — no system. Everyone gets a page of 48 numbers scattered randomly. On "go," circle them in order — 1, 2, 3 — as fast as you can, for 60 seconds. Write down the highest number you reached.

The system. Fold the same page in half, then in half again. Unfold it — now there are four quadrants. The numbers run clockwise through them: 1 in the top-left, 2 top-right, 3 bottom-right, 4 bottom-left, then back to the top-left for 5. The next number you need is always in the next quadrant. You only ever search a quarter of the page.

Round 2 — same page, same 60 seconds, with the system. Every single time, without exception, the second number is dramatically higher. Not 10% higher. Often double.

Nothing about the page changed. Nothing about the person changed. The only thing that changed was that chaos became a system.

That's the whole argument for building systems in a business, condensed into two minutes with a pen. And it's also the argument for delegation: you can't hand off chaos. You can only hand off a system. If you want to give a task to someone else, the system has to exist before the person does.

"Discipline — the ability to give myself a command and follow it!"
— Steve "Action" Jackson

What's one task in your business that's still Round 1 — still chaos, still search-the-whole-page? What would the fold-in-half version of it look like?

Not on the TERT list yet? Join here — it takes 30 seconds: https://lp.constantcontactpages.com/su/wBhnQRI/RoundTable

Sign Up Here!

10/01/2026

The most common reason someone tells me they haven't come to a Round Table is: "I'm not really in real estate, so I probably don't belong there."

Here's a member who was never in real estate at all — his words, not mine:

"Steve is truly a genuine person and mentor. Even though I never personally invested in Real Estate, Steve became someone I greatly admired as an entrepreneur and self-made man. He has inspired me to look beyond the traditional world of investing and take time to learn and study the 'Macro' world of investing and how everything is connected. Steve is confident in his abilities and is a man of his word."
— Brendon Roark

He didn't come for a deal. He came for the room, and stayed for what the room taught him about how markets, money, and decisions actually connect to each other — a lesson that has nothing to do with whether you personally own a rental property.

That's on purpose. TERT was never built as an investor-only club. It's mindset, business skill, leadership, and real estate training — four pillars, not one. A Realtor, a contractor, a coach and a landlord get the same room and the same four questions.

"Unselfish — do you for one what you wish you could do for anyone and everyone."
— Steve "Action" Jackson

October's Round Table date is locked: Thursday, October 22. Topic and registration aren't live yet — join the list here: https://lp.constantcontactpages.com/su/wBhnQRI/RoundTable — you'll be first to know.

Sign Up Here!

09/30/2026

A 19th-century mountain railway. A 2,000-year-old forum. Neither one got easier to build or run over time — the mountain is still steep, the stone is still heavy. What changed is that someone designed a system precise enough that it kept working long after the person who built it stopped showing up.

That's the whole point of building a business instead of just running one. A business that only works because you're grinding in it every day isn't a system — it's a very well-paid job with your name on the door. A business that keeps running on the days you're tired, or sick, or on the other side of the world, is the version that's actually built.

"If you are tired then do it tired!"
— Steve "Action" Jackson

What in your business only runs because you personally show up every single day?

Not on the TERT list yet? Join here — it takes 30 seconds: https://lp.constantcontactpages.com/su/wBhnQRI/RoundTable

09/30/2026

If your team's morning update is a message that says "all good, working on stuff" — you don't have visibility. You have a vibe.

Here's the four-question form every person on my team fills out and sends me by 9 AM. Ten to fifteen minutes, tops:

1. Top 3 priorities. Their three most important focuses for the day. Not a to-do list — the three things that actually matter.

2. Outcomes / results. What they'll actually produce for each one. A priority without a stated outcome is just an intention.

3. Problems / challenges. What's in the way, surfaced early — before it becomes Thursday's fire instead of Tuesday's heads-up.

4. Questions for me. What they need from their leader to move. This is the line that turns a status report into a tool that actually unblocks people.

That's it. Four boxes, one email, every morning, by 9. Not a meeting. Not a check-in call. A rhythm.

The owners who complain they "have to micromanage everything" are almost always missing this — not because their team can't be trusted, but because nobody ever gave them a structured, low-friction way to ask for help before the problem got expensive.

"Without self-discipline success is impossible."
— Steve "Action" Jackson

If you ran this with your team starting tomorrow, what's the first "problem/challenge" line you'd expect to see?

Not on the TERT list yet? Join here — it takes 30 seconds: https://lp.constantcontactpages.com/su/wBhnQRI/RoundTable

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09/30/2026

https://youtu.be/eYxD10PI6u0?si=36RVfNHDp8vzEB84

📚 GRAB YOUR COPY of John C. Maxwell's, Failing Forward ⬇https://st...