Thinking Out Loud with Dean Jackson

Latest Episodes:

30 years later people still spend their money on these core things. Jul 05, 2026

Show notes

Filing this one under we are living in the future. As I close out journal number one, a couple of books from 1996 planted ideas that have stuck with me for 30 years. The Discipline of Market Leaders says businesses win as product leaders, operationally excellent companies, or customer intimate companies, and I realized real estate is really all three across the before, during, and after units.

The One to One Future by Don Peppers and Martha Rogers predicted the privacy issue and imagined a future where we'd each have an advocate, someone we share everything with who acts as our intermediary with the marketplace. I coupled that with the customer intimate idea and saw the opening.

Then I mapped the cradle-to-grave list of where people spend money, from babies and toddlers through weddings, homes, cars, and retirement. Every one of those is a contextual certainty, something lots of people are moving through, and almost nobody steps up to organize the category and be their advocate.

The biggest prize is the first-party relationship with a homeowner, which is why companies like Rocket are combining mortgage, insurance, and brokerage. Whatever your business is, start asking who else serves the same person. That closes journal number one, 17 episodes in, with about 150 journals still to go.

Show notes: https://deanjackson.com/podcasts/tol/032-30-years-later-people-still-spend-their-money-on-these-core-things/

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How I talk my ADHD brain into doing the thing I'm procrastinating now Jul 04, 2026

Show notes

Do you ever wonder who you're talking to when you talk to yourself? Some of my best conversations have happened in my own head, and going through my journals I found the first of many written-out dialogues where I play both parts to talk my ADHD brain into doing what I'm avoiding.

An ADHD brain only really has two time frames, now and not now. If something isn't due right now, it's a future Dean problem. And when you're procrastinating, you're usually procrastinating the noun of the task, the big thing like finish expired package that you can't take action on.

So the dialogue narrows me down. What would you actually have to do to finish it? I list the real steps, estimate how long each takes, figure out which part I'd enjoy most and which I could delegate, then nail down a specific time and place to do it.

The next morning I wrote that I was amazed how well it worked and was looking forward to doing it again. It stuck. This exercise on its own can help you take something you're stuck on right now and actually get it done.

Show notes: https://deanjackson.com/podcasts/tol/031-how-i-talk-my-adhd-brain-into-doing-the-thing-im-procrastinating-now/

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A 7-Step Checklist That Instantly Improves Any Ad, Postcard, or Mailer Jul 03, 2026

Show notes

Back in July 1996, Eben and I were touring the country doing real estate seminars, and I'd run an ad clinic where people submitted their ads and postcards. I came across the seven-step checklist I used, and it's just as durable today as it was pre-internet.

It starts with the target: have you selected a single market, so the right person instantly knows this is for them? Then does your headline tell the complete story on its own? Once you've got the right person and a headline that pulls them in, most of the job is done.

The rest of the checklist covers making it look like news instead of an ad, using conversational language, having a compelling offer, being crystal clear about the one action you want, and using words that let people get something instantly without talking to a salesperson.

I explain Broca's area, the part of the brain that filters out ads so you can ignore billboards and skip commercials, and why packaging your message as content sneaks past that filter. There's also the test I always come back to: if this postcard were you delivering the message in person at someone's door, would you actually pay to have it said that way?

Show notes: https://deanjackson.com/podcasts/tol/030-a-7-step-checklist-that-instantly-improves-any-ad-postcard-or-mailer/

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You Don't Actually Want More Money Jul 02, 2026

Show notes

Going back through my journals, I found the seed of what I've wanted for 30 years. In Los Angeles in June 1996, talking with Eben, I realized what I really want isn't a sum of money. It's a feeling. What everybody wants is peace and power, and I've come to understand that power as agency, being able to live your life however you choose.

I'd started watching other entrepreneurs get totally absorbed by their businesses, waking up every day to put out fires and chase a self-induced urgency. I didn't want to trade anything for that life.

That trip introduced me to La Jolla, and it crystallized the hub-and-spoke way I still love to live. Later I named the three lifestyle elements I'm after: daily joy, abundant time, and financial peace. The temptation when you're young is to keep stacking on things that cost you time and create stress.

Hustle culture treats a lifestyle business as somehow lesser, but ask whether the 10x actually adds any daily joy or abundant time. My friend Taki Moore calls the answer a lifestyle empire, an eight-figure business built only around what you love. It works because of marketing, the lever that funds the life you really want.

Show notes: https://deanjackson.com/podcasts/tol/029-you-dont-actually-want-more-money/

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Why the Best Marketers Make Ads That Don't Look Like Ads Jul 01, 2026

Show notes

This wraps up my little series on the four cornerstones of being an enduring marketer. We've covered behavioral psychology, your own frameworks, and copywriting. The fourth is what I put under the umbrella of design, meaning how you package and present your message so people actually consume it.

One of the most durable things I picked up early is making something look like news instead of an ad. When your message looks like content, people read it through a different lens than they use to filter advertising. I'm not talking about flashy or artistic, just practical presentation that draws the eye.

Spending a day with Jerry Ballinger, I saw how much attention he paid to layout, and I decided to learn to do it myself in PageMaker so there was zero friction between my ideas and getting them into the world.

I use two filmmakers to make the point. Robert Rodriguez says learn the technical skills and become dangerous. Terry Gilliam told Tarantino your job isn't to get your vision on the screen yourself, it's to describe it clearly and hire the best people. With AI and today's tools, that second approach matters more than ever. The four cornerstones haven't changed, only the ways we create and distribute them.

Show notes: https://deanjackson.com/podcasts/tol/028-why-the-best-marketers-make-ads-that-dont-look-like-ads/

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90% of Copywriting Comes Down to 4 Words Jun 30, 2026

Show notes

I learned four words from Jeffrey Lant that carry about 90% of what you need to write copy that works: you get benefit now. If any word you write doesn't sit under one of those pillars, you're on the wrong path.

The mistake almost everyone makes is thinking their prospect cares as much as they do about them and their product. Nobody cares that you're the leader or that you've spent your life at this. They care about what they get. I share the Stop Your Divorce letter that opens completely on the prospect's wants and has sold over $5 million from one sales letter I wrote in 1998.

I'll walk you through the exercise I run on any piece of copy: strip the adjectives and adverbs, look at the nouns and verbs, and ask if you're actually saying anything real. Then read it as your prospect and ask whether that's how they'd want to be introduced to your message.

I also give you the people worth studying: Jeffrey Lant's Cash Copy to start, plus Dan Kennedy, Jay Abraham, Gary Halbert, John Carlton, and Brian Keith Voiles. Nearly every dollar I've made in 30 years came from something I wrote or said.

Show notes: https://deanjackson.com/podcasts/tol/027-90-of-copywriting-comes-down-to-4-words/

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The Psychology Behind Why People Buy Jun 29, 2026

Show notes

If you want one place to start with behavioral psychology, go down the path of social psychology. The most cited name in it is Robert Cialdini, and I read his book Influence back in 1996. There's a direct through line from that moment to everything I do today.

Cialdini calls them the six weapons of influence, things hardwired into us that shape our decisions without us knowing. Reciprocity is the first. Do something nice for someone and they feel they owe you one back.

That's why I lean so hard on giving away free books. It starts a relationship, and it stacks with commitment and consistency, where once you've raised your hand for something you feel pulled to keep moving in that direction.

Technical skills go obsolete. Everything I learned about building sites in Microsoft FrontPage is useless now. These psychology principles are durable, so I'd start with Influence and Pre-Suasion, then Predictably Irrational by Dan Ariely.

Show notes: https://deanjackson.com/podcasts/tol/025-the-psychology-behind-why-people-buy/

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Turning Buyer Psychology Into A Marketing Model Jun 29, 2026

Show notes

The second cornerstone is creating mental models, frameworks you can overlay on a situation to give yourself a shortcut. Michael Gerber's franchise prototype was the first one I was ever exposed to.

My model was simple. Create a guide, run ads to get people to raise their hand, then treat them like someone who's going to buy and give them valuable information. I've since learned that's roughly a 50% chance over the next two years.

I'm not trying to convince anyone up front. I'm identifying the invisible prospects who are already thinking about buying, then letting reciprocity, liking, and commitment and consistency do their work. Those eight profit activators grew out of this exact thinking.

There's a line I love: a man with an experience is never at the mercy of a man with an idea. Take whatever you do, build your own model, document it, and you'll trust that anything you run through it has a better shot.

Show notes: https://deanjackson.com/podcasts/tol/026-turning-buyer-psychology-into-a-marketing-model/

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Master These 4 Marketing Skills First... Jun 27, 2026

Show notes

A man named Jerry Ballinger shaped a lot of my thinking when Eban and I were in our late twenties. Looking back, everything I've done traces to four cornerstones I picked up around him.

First is behavioral psychology, understanding why people do what they do so nothing baffles you. Second is building mental models and frameworks, like knowing music theory so your ideas fit together instead of being random.

Third is copywriting, which I really mean as communication in every form, speaking and writing your ideas so people accept them and change. Fourth is design, framing your message so there's zero friction between your idea and the world.

AI can help with all of it now, but the thing that hasn't changed is behavioral psychology. People still do what's in their own self-interest, and if you frame your ideas around that, you win.

Show notes: https://deanjackson.com/podcasts/tol/024-master-these-4-marketing-skills-first/

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The Less I Do, the Richer I Get. Jun 26, 2026

Show notes

San Francisco, 1996, sitting across the bay from the city with Eban Pagan. This is where I first felt income showing up that didn't come from my own effort.

Eban and I mapped out a system where every piece, the ads, the voicemail, the follow-up calls, the newsletters, could be done by other people. The less I did myself, the more I could actually make.

What most people really want isn't to do the work. They just want someone ready to buy or sell. So the goal grew from replacing me to replacing the client too, doing everything for them.

Back then it was outsourcing to other humans. Now it's AI, which I couldn't have imagined in 1996. Same core model though: build something that runs without you, then duplicate it.

Show notes: https://deanjackson.com/podcasts/tol/023-the-less-i-do-the-richer-i-get/

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