Thinking Out Loud with Dean Jackson

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If You're in Business & Have ADHD -- Watch This... Jun 25, 2026

Show notes

The foundational thing behind everything I've built is a duplicatable model. Michael Gerber taught me to treat the business as the product, something separate from me, not something I identify with.

My guide to Halton Hills was one core unit I could copy again and again. Toronto and Beyond was just that same thing duplicated, the way Ray Kroc built Hamburger University to prototype every McDonald's.

I'm great at getting something scale-ready, cracking the code the first time. I'm not the guy who wants to sing the same song every night on tour, and that's the first place I can see my ADHD wiring, looking back.

Most businesses live in a five-mile bubble. If you can make something work in one market, you've got the key to duplicate it. So look at your own business and ask what parts you could copy.

Show notes: https://deanjackson.com/podcasts/tol/022-if-youre-in-business-have-adhd-watch-this/

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These 3 Principles Built A $2 Trillion Company Jun 24, 2026

Show notes

I'm 30 years into journaling every day, and I've been reading back through journal number one from 1996. Some patterns in me haven't changed, and neither has human nature.

Back then, the realtors I was coaching expected to run an ad today and sell a house this weekend. I had to learn something harder, that investing time to build a system with a future payoff beats chasing the immediate result.

What struck me is that sellers wanted the exact same thing in 1996 as they do now. Sell fast, get the most money, least hassle. It's the same bet Jeff Bezos made building Amazon around what people would always want.

If you keep people focused on the result they really want, and you handle whatever it takes to get them there, that hasn't changed in 30 years and I don't think it'll change in the next 30.

Show notes: https://deanjackson.com/podcasts/tol/021-these-3-principles-built-a-2-trillion-company/

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Cold Calling Worked. That’s Why I Stopped Doing It. Jun 23, 2026

Show notes

I'm a creature of habit, and going through 150 journals made me see how much of life is a kind of Groundhog Day. What kept jumping out at me was the growing wake of intellectual property I've built up over the years.

Cold calls work. That's not the problem. The problem is there's no residual value, so the second you stop, the results stop. Michael Gerber's E-Myth taught me to put things into a format I could use again and again, which is how I built the Halton Hills guide and licensed it to 40 agents.

One project in this journal was the Home Buyer College, a set of education pieces we mailed to people who'd buy a home in the next year or two. It started as physical mail and became the email follow-up sequences we still use today. Eben Pagan and I would mine Cosmo covers for headline formulas to make it all land.

The lesson I keep seeing is how valuable it is to package and document what you know. Every piece builds on the last, and 30 years later they're still creating value in the world.

Show notes: https://deanjackson.com/podcasts/tol/020-cold-calling-worked-thats-why-i-stopped-doing-it/

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If I Ran Your Marketing, Here’s Exactly What I’d Do... Jun 19, 2026

Show notes

This one's a full walkthrough. I take you through exactly what I'd do if I walked into your business tomorrow and took over the marketing, starting with the before unit, the part that finds people who want what you do.

I'd begin with fresh eyes and one hard question. What could you do if you only got paid when the client got the result? That's where the real money is, and it's how the Koch brothers grew their company by investing in the outcome alongside their partners.

From there it's selecting a single target market at the highest level, then figuring out whether your prospects are visible or invisible. The best way I know to get invisible prospects to raise their hand is to offer a book, so I walk through my five title formulas and the word palette I use to build them.

Once someone raises their hand, I show how I think about them as an asset, why about half will act within 100 weeks, and how to greet them and make an offer so easy they can't help but take the cookie. It's the whole profit activator model in one sitting.

Show notes: https://deanjackson.com/podcasts/tol/019-if-i-ran-your-marketing-heres-exactly-what-id-do/

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How I tricked my ADHD brain into building my business & life Jun 14, 2026

Show notes

I've kept a journal every day for more than 30 years, and it's without question the most important habit in my life. As an introvert, writing is how I think out loud and have a conversation with myself.

Journal number one is where I first met the Myers-Briggs types and found out I'm an INTP. Knowing how you're wired is an advantage. Over the years I added the Kolbe and Working Genius, and the lesson hasn't changed. Don't fight your natural tendencies, change your environment to support them.

So instead of forcing myself to be tidy, I ask my mind a guiding question. I write down the question, paint a picture of exactly what the ideal looks like, then list every idea I can think of to get there. Your mind loves to solve problems if you give it the question and a pencil.

I've been using that guiding-question format for 30 years, and it evolves into something even better a few journals from now. More to come.

Show notes: https://deanjackson.com/podcasts/tol/018-how-i-tricked-my-adhd-brain-into-building-my-business-life/

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The 1996 Marketing Idea That Changed My Life Jun 12, 2026

Show notes

Up until 1996 I was a practitioner. I used marketing to build my own real estate business, but I wasn't teaching it to anyone yet. Going through journal number one, I can see the moment that started to change.

One of the first times I applied what I knew outside real estate was helping a friend in Ottawa who placed contract programmers. Instead of chasing companies for job openings, we ran an ad that gathered the programmers first, then walked into the telephony companies with the people already in hand.

That's the first principle I keep coming back to. If you help enough other people get what they want, you can get anything you want. It's why finding buyers first makes you valuable to any realtor who needs listings.

This same journal also holds the day I first walked into the Strategic Coach office and picked up Dan Sullivan's How the Best Get Better, before I'd ever met him. It's funny to see where these things start.

Show notes: https://deanjackson.com/podcasts/tol/017-the-1996-marketing-idea-that-changed-my-life/

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I haven't made a cold call in 35 years… here's how Jun 05, 2026

Show notes

When I got started in real estate, all I did was make cold calls. People actually answered the phone back then, but I realized fast that it was a hamster wheel. Take me out of it and there was no business left.

Michael Gerber's The E-Myth flipped that for me. I learned to work on the business instead of in it, so I built a lead-getting system. I made a guide to Halton Hills real estate prices that let people learn about the area without driving out to see it, and an old agent's box of floor plans gave me the idea.

That guide, plus a Market Watch newsletter I mailed every two weeks, brought in leads while I did nothing. I licensed the whole system to 40 agents across Toronto and beyond, and that's what led me to Joe Stump and to meeting Eben Pagan.

This is where my life with direct response really began, and it's why I haven't made a cold call since.

Show notes: https://deanjackson.com/podcasts/tol/016-i-havent-made-a-cold-call-in-35-years-heres-how/

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I journaled everyday for 30 years & here's what I know so far... May 29, 2026

Show notes

I just turned 60, and to mark it I went back to the Eagle Ridge Mall in Lake Wales where I sat with my very first journal in 1996. I've written in a journal every single day since then, and there are now hundreds of them.

Back in 1996 there was no Google, no YouTube, no Facebook, and Apple was failing. Looking back, I can see my whole life as a series of vector-changing moments, the handful of times something happened and I ended up pointed in a completely new direction.

The biggest one took me off the tennis court. I trained at Rick Macci's academy alongside future champions, but at 22 I realized I didn't want to still be grinding on tour at 30. A story a former player told me on a boat in Vero Beach made me pivot to business, and that's how I ended up back in Florida starting this journaling adventure.

This is the start of a series. I'm opening journal number one and working through all of them, pulling out the insights that still hold true and the opportunities I saw but didn't act on. Hope you'll come along.

Show notes: https://deanjackson.com/podcasts/tol/015-i-journaled-everyday-for-30-years-heres-what-i-know-so-far/

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Establishing a BRAND Mar 04, 2021

Show notes

What does it actually mean to establish a brand? As a direct response guy focused on results, I've always felt the tension with the branding camp. Then a Ray Dalio video on the economic engine clicked something for me. A market is just the sum of individual microtransactions, one person trading money with another. A brand works the same way.

So here's my definition: a brand is a buying reflex affecting now decisions. The only time anyone can buy is now. Buying intention and buying history feed into it, but you can't bank those today. Coca-Cola and Budweiser have simply built that reflex in billions of individual minds over time.

That's actually hopeful. The microbrewery in Punxsutawney owns the reflex in its own town, often just through proximity, recency, and a clear message. Figure out the exact moment someone chooses, then make your reflex the one they lean toward.

Show notes: https://deanjackson.com/podcasts/tol/014-establishing-a-brand/

Join me live on the next free 50-Minute Profit Finder call: 50minuteprofitfinder.com/podcast

who not how zoom Oct 30, 2020

Show notes

In less than 90 minutes, Joe Polish and I are going live on Zoom with Dan Sullivan and Ben Hardy for their new book Who Not How, so join us at ilovemarketingzoom.com at 1pm Eastern on Friday, October 30th.

Show notes: https://deanjackson.com/podcasts/tol/013-who-not-how-zoom/

Join me live on the next free 50-Minute Profit Finder call: 50minuteprofitfinder.com/podcast

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