Thinking Out Loud with Dean Jackson

I went digging through one of my big 1996 projects, the Home Buyer College. It was a correspondence course of newsletter reports we mailed as follow-up to everyone inquiring about buying a home, updated every two weeks when the new MLS catalog came out. It's hard to get back into the mindset that in 1996 your only ways to reach people were direct mail, print, the phone, or meeting in person. Radio and TV were cost-prohibitive for a small business. The Home Buyer College was the first real collection of IP I ever built, and we still use pieces of it to this day.

What struck me looking back was that I had a complete system for producing those five-to-eight page reports, and it's the exact same model I follow now. Step one, and 80% of the whole game, is the headline. Eben Pagan and I were headline hunters at all times, pulling cues from Cosmo, the home magazines, the National Enquirer, trading made-up headlines like improv theater for marketing nerds. Step two, list eight to ten subheads, the major points in short form. Step three, drop three to five talking points under each subhead. Step four, expand each one like act one, two, three. Step five, write the lead and the closing paragraph. Done right, the report is a work of art you can grasp just by reading the subheads.

Here's the part that gets me. Back then, creating that content meant interviewing an expert for twenty minutes, mailing the tape off to be transcribed at a dollar a minute, then paying a writer a hundred bucks to turn it into a finished report. Call it a $2,400 investment for twenty-four newsletters. That same work could be done by lunchtime today with Claude or ChatGPT. We don't realize what a gift that is.

But I'd separate the content into two kinds. A book report just compiles what's already known about a topic, and AI is perfect for that. A field report is your own unique approach, the thing that differentiates you from what already populates the large language models. That's where you need to focus. The tools and the distribution have completely changed between 1996 and 2026, but our desire for information, paired with your ability to create your own perspective on it, is the durable advantage that lasts.

Show notes: https://deanjackson.com/podcasts/tol/037-inside-my-1996-content-factory-vs-today/

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This picks up right where yesterday left off. The zone structure works. Zone one is sleep, and I've become what Brian Johnson calls a professional sleeper, so my biorhythm is firing on all cylinders. Zone two is my cleared morning, nothing allowed to stop the creative work. Zone three is my Tuesday-through-Thursday afternoons, all synchronous, all scheduled, and I'm 100% reliable and present for every one of them. The thing I still can't crack after 30 years is getting myself to choose and do the most valuable thing when there's no consequence, no deadline, and nobody waiting on me.

My friend Taki Moore has the same kind of ADHD I do, and he says everything he gets done is because he's got a date with a dude. He works out because someone meets him for it. He shoots his videos because someone shows up to record them. I've got a date with a dude every morning too. Josh flips the camera on at 8:59, and that's the only reason these episodes exist. It reminds me of the FSO contracts studios sign for the services of a Jim Carrey or an Adam Sandler, where the deal is really just that the person shows up and does the work. Here's the paradox. I crave the freedom to not have to do anything, I've built my whole schedule around protecting it, but the things that actually get done in my life all come from constriction and other people's expectations. I half-joke that I need a conservatorship, some new management I don't mind.

Our mutual friend Lior Weinstein said something around a campfire that stuck with me. He doesn't know how to prepare his kids for a future none of us can see. Everything we do is really the culmination of what we did yesterday. Dan Sullivan has been running with this for 200-something days straight, waking up and asking how to make today a better yesterday, tomorrow. I've been playing the same word game. Instead of what would I like to do today, it's what would I like to did today. We only get about 1,000 minutes a day to spend, and the only ones that count are the ones that make it onto the permanent record. I could have done anything with these last 10 minutes, but the only reason tomorrow is a better yesterday is that I actually recorded them.

The picture I keep coming back to is Supermarket Sweep. The shelves are lined with every idea I could work on, and I catch myself standing on the sidelines just looking, thinking maybe I'll go grab some of that. But the only things you get to keep are the ones you put in your basket, and putting them in the basket means spending the time to actually do them. That's the 30-year work in progress, and maybe awareness builds its own momentum. If you struggle with the same thing, or you've found something that works, leave a comment. I'd genuinely like to know.

Show notes: https://deanjackson.com/podcasts/tol/036-i-know-exactly-what-to-do-so-why-dont-i-do-it/

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This one starts on page 31 of journal number two. Back then I'd just picked up Dan Sullivan's How the Best Get Better and gotten hooked on two ideas. Unique ability, the thing at the core of what you do that energizes you and needs no amping up. And the entrepreneurial time system, three kinds of days: focus days spent in your unique ability, free days with nothing to do with work, and buffer days to prepare for both. I overlaid that lens onto a weekly schedule, and I kind of laugh now, because the schedule I sketched in 1996 is almost identical to the one I run today.

Here's the thing I keep coming back to. Time hasn't changed in 30 years. Same 24 hours, life still moves at 60 minutes an hour, and the only time we ever get to do anything is now. So I stopped trying to reinvent the rhythm and leaned into it. Bed at 11, up by 7:30, in the car by 8. My ADHD brain loves that deadline, it's almost magical how I never miss it. Same breakfast spot every morning, journal open, whatever pops out becomes the day's insight. Then straight across the street to the coffee shop, 9:30 to noon, no phone, no appointments, no interruptions. That's my unique ability time, writing, solving marketing puzzles, hatching evil schemes.

Early in real estate I played the game like Tetris. Time's moving, the blocks keep falling, and you're shifting and reacting and hoping it all fits. Now I treat it more like Guitar Hero. The notes still come at you, but they've been pre-arranged, so if you just play the right ones in the right slots, the day sounds ordered and purposeful. Appointments only land Tuesday, Wednesday, Thursday afternoons. Friday through Monday, nothing scheduled. Wrap by six, and the evening is just for living.

I'll be honest about where I still struggle. That 10-to-noon block is the hardest part for an ADHD brain. I've got the time, but choosing the one thing to work on out of everything I could do is the real fight. Ned Hallowell calls it VAST, too many open loops pulling at you. So it's still a work in progress after 30 years. I've got a new paradigm I've been chewing on from some conversations with Dan Sullivan, and I'll get into that tomorrow.

Show notes: https://deanjackson.com/podcasts/tol/035-i-almost-cant-believe-ive-gotten-away-with-this-daily-schedule-over-30-years/

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I found a little time capsule, page 20 of journal number two from 1996. Back then I was chewing on the idea of advocacy from The One to One Future and applying it to real estate. The realtor business is transactional. You sell someone a home and move on, even though 84% say they'd use that agent again and fewer than 25% actually do. The number one reason is they lost touch. That's a valuable relationship left on the table.

Looking back 30 years, I realized I was onto something with the things that don't change. I predict these seven categories survive the next 30 years. The context stays the same even if the content shifts. Home is the biggest line item, everything to do with the house. Food, because we're still 100% human and haven't merged with the robots yet. Cars and transportation. Kids, a whole economy on its own. Money, including debt, investing, and business owners spending to bring money in. Health, as the boomers and Gen X age into longevity. And me, the discretionary pleasure spending on travel, hobbies, and entertainment.

Everyone frames AI as disrupting things. I think the better question is how AI can enhance these seven. Pair it with the categories people already spend on and you're building on durable ground. Over 85% of the average household budget is spent within five or ten miles of home, which is why HVAC and home service companies keep thriving. That need isn't going anywhere.

Overlay advocacy on top of any of these and you've got a position. Instead of thinking about the one narrow spoke you provide, elevate out and become the person's advocate for the whole category. With realtors, that looks like being a home advocate for anything to do with their house. Take the one to one future and apply it to whatever category you're in, and you've set yourself up for the next 30 years.

Show notes: https://deanjackson.com/podcasts/tol/034-i-predict-these-7-business-categories-will-survive-thrive-in-the-next-30-years/

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This one goes back to the summer of 1996, when I read Jerry Spence's How to Argue and Win Every Time and realized the real tool isn't the pitch, it's the story. Stack that on Cash Copy and Robert Cialdini's Influence and you stop collecting separate lessons and start owning a durable model you can use again and again.

The first time I used it, I had a developer client north of Toronto with six unsold cottage lots in Muskoka, and it was already past Labor Day. His ads looked like ads, 33% off, blowout sale, all of it trying to convince people. So I asked the only question that matters. What's the truth here? The truth was he had a balloon payment coming due on another property and needed these lots sold to make it.

We had the lots appraised so the discount carried real authority, then I wrote the ad as a newspaper article in his own voice. I need to sell these six Muskoka home sites in the next 30 days, 33% below their appraised value, and here's my dilemma. When you put your sword down like that, people stop resisting and get curious. He sold all six lots in two weekends and blew out his fax machine.

That became a permanent hammer in my toolkit. A townhouse that sold over asking in a single weekend. A giant postcard for Joe Polish's house at the top of Camelback Mountain, an open letter to anyone who ever wondered what it'd be like to live up there. The move is always the same, tell a story that lets the other person feel like they're winning. Thirty years later I'm still running this exact playbook.

Show notes: https://deanjackson.com/podcasts/tol/033-stop-trying-to-convince-people-just-start-telling-the-truth-watch-what-happens/

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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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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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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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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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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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