Thinking Out Loud with Dean Jackson

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**Thinking Out Loud with Dean Jackson**

Dean Jackson thinks out loud about marketing, referrals, positioning, and the small ideas that quietly change how a business grows. Short, unscripted episodes. The raw thinking behind BreakthroughDNA and the 8 Profit Activators.

Latest Episodes:

How to Get 6 Months of Marketing Ideas for Your Business on One Page Jul 15, 2026

Show notes

Page 179 of journal number two. Fall of 1996.

At the top I'd written one question... how could we find buyers for people wanting to move to Winter Haven?

Then I just filled the page underneath it. 26 ideas, one sitting.

That's the whole trick I want to hand you today.

Put a topic at the top of a blank page and task your brain with filling it. You'll be amazed how creative you get the moment you put a constraint on it.

We love to solve problems. We love to play inside boundaries. Give your mind a fence and it starts sprinting.

And here's what turns it into a system. 26 ideas is six months of marketing. Pick one a week, do that one thing, and you never sit staring at an empty calendar again.

Let me give you a few off that page.

A tape tour of Winter Haven... a cassette and a map, numbered tracks, so you could drive through a neighborhood with someone who knows it sitting right beside you. A couple of lines down, that became a video tour.

A welcome letter from the mayor, tucked inside the guide. I'd sold him his house, so I just asked.

The builder model lists. Everybody else was hounding builders the same way... give me listings, give me listings. I flipped it. I offered to write a letter to the people who toured a model home and didn't buy new. Maybe they'd want a resale. Here's a guide to the area.

I was giving instead of taking. And I ended up with a stack of backup listings anyway.

Take-one boxes on the counter. HR directors at the biggest companies in town, the people who know first when somebody's relocating. A brides-to-be list, because people getting married are often about to buy a home.

And line 23 just said niche guides. A lakefront guide. A golf course guide. A condo guide. That one line grew into one of the biggest revenue ideas I ever built.

All of it from a single page and a single question.

So here's your nudge. Sit down and write across the top... what are 26 things I could do to get more customers for my business?

Then fill the page.

I think you're going to surprise yourself.

Show notes: https://deanjackson.com/podcasts/tol/042-how-to-get-6-months-of-marketing-ideas-for-your-business-on-one-page/

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

If My Life Depended on One Letter, Here's Exactly What I'd Send Jul 14, 2026

Show notes

November 1996. I'm reading the Gary Halbert newsletter, and he asks a question I've never stopped thinking about.

What if you could only mail one letter... and you had to get a response, or you'd be beheaded?

Dramatic. But stay with it.

Because the moment your life is on the line, every lazy direct mail habit goes right out the window.

Gary walked it through step by step, and I've been repeating his logic at least once a month ever since. At Breakthrough Blueprint. At the workshops. On podcasts like this one.

First, you'd pick someone actually likely to buy. You don't waste your one shot on a person who never will.

Second, you'd never send it bulk. Bulk mail gets lost if they've moved. First class gets there, or gets forwarded. The letter has to reach their hands.

Third, it has to get opened. Gary's the one who said people sort their mail over the garbage can... an A pile and a B pile. Bills and a birthday card from grandma go in the A pile. Anything that smells like a mass mailing goes in the B pile.

So if your life depended on it, you'd make that envelope look like it was meant for one person. Hand-addressed. A real stamp, maybe two, maybe a little crooked. No logo. No teaser copy. No window. Just a discreet return address.

Fourth, it has to get read. Open it up and it should look like a letter... not a pile of brochures flying out. The headline has one job: get them curious enough to keep going.

Then Gary's favorite move. The grabber.

He popularized the dollar bill letter. A crisp dollar attached to the top. "Dear Josh, I've attached a dollar to this letter. Two reasons..." And in the PS: that dollar's yours to keep. Frame it. Tell people it's the first dollar you ever made from your relationship with Gary Halbert.

That's a master class in treating one mailing with the importance it deserves.

And here's the thing... there's no money in saving money. No money in cutting corners. Not when it's life or death.

I still mail this way. We just sent a one-page letter wrapped in a stack of prop hundred-dollar bills... and now a QR code carries people to the rest of the story.

And you know what that same question handed me years later?

The 9-word email.

Imagine you could only send one email. To one person. And you had to get a reply.

What would you write?

That's the level of thinking. Start there.

Show notes: https://deanjackson.com/podcasts/tol/041-if-my-life-depended-on-one-letter-heres-exactly-what-id-send/

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

The More Routine My Life Gets, The More Freedom I Have Jul 13, 2026

Show notes

Happy Monday. Beautiful morning for July.

Yesterday I was talking about Deming and driving variation out of your marketing. This morning I turned that same lens on myself.

Where in my own day am I being random... when I could be consistent?

My natural setting has always been loose. Free. Do whatever the day feels like. But the older I get, the more I believe the opposite. The freedom is in the constraints.

So I went back through my journals and found five zones where I've quietly been driving the variation out.

Sleep is the first one. I'm chasing double crowns on my Oura ring now, one for readiness and one for sleep. Lights out around 11, up between 7 and 7:30. It's a little like the floor is lava when you were a kid, jumping to the bed at the last second... but somehow it tricks my brain into going.

Then the morning is the same every day. In the car at 8. Same breakfast spot, journal open for the day's insight. Record this video. A pourover from Honduras or Guatemala across the street by 9:30.

Then the focus block, 10 to 12. Phone locked in the safe, so nothing can pull at it.

Everything that involves other people, all the calls and the Zooms, gets boxed into Tuesday, Wednesday and Thursday, 1 to 6.

Meals are their own zone. A carnivore setup, the same handful of things I know work, cubed ribeye or fillet in the air fryer to bookend the day. In the words of Jeff Foxworthy, put a bowl of that on your head and your tongue will beat your brains out trying to get to it. That kind of attention has me down almost 20 pounds in a couple of months.

And here's the part most people miss. There's no procrastinating in your personal time... because you've got no expectations of it. You just do whatever you want. A good Netflix series. A movie. All of it.

The proof of the whole thing is the pile behind me. The only way to be sitting here in 2026 with 160 journals is to have removed the variation and written in one every single day.

So that's your nudge for today.

Look at your own five zones... sleep, mornings, work, meals, personal time... and see where a little less variety buys you a lot more freedom.

Let me know how it works out for you.

Show notes: https://deanjackson.com/podcasts/tol/040-the-more-routine-my-life-gets-the-more-freedom-i-have/

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

How to Turn Your Advertising From a Slot Machine to a Vending Machine Jul 12, 2026

Show notes

This one starts in Nashville in October of 1996, on my first lap around the country. My friend Mike Hardwick, founder of Churchill Mortgage, the only mortgage company Dave Ramsey has recommended for years, took Eben and me out for dinner and a high school football game, then said he was taking us for a treat. We came over a hill and Mike said, boys, the hot light is on. We had no idea what it meant, but it sounded good. It was my first Krispy Kreme, a whole dozen hot off the line with chocolate milk between us, and it's still one of my favorite Nashville memories. A nice reminder of what long-term relationships are worth.

That same fall I got introduced to the work of W. Edwards Deming, the man who went to Japan after the war and helped turn them into the highest-quality manufacturers in the world. His principles of profound knowledge have shaped how I think ever since, and the first one that grabbed me was simple: variation is in everything. Once you see that, the goal becomes obvious. Drive out the variation and make things stable and predictable. That's all we really want from our marketing. I've come to describe it as wanting your advertising to be a vending machine instead of a slot machine.

The worst thing you can do is confuse an unstable system for a verdict. Someone mails one postcard, gets nothing, and decides postcards don't work. Or they mail a different thing to a different list the next month and draw the same conclusion. Improvement only comes from a place of stability. So I started asking what's stable in real estate. Here in Winter Haven there are about 2,100 lakefront homes, and roughly four to five percent of them sell every year, so 90 to 100 of those owners will move in the next twelve months. The stable play is mailing to those same 2,100 people every month, not blasting 2,000 random postcards wherever you're emotionally led that week.

Deming proved this with his red bead experiment. Teams would dip a paddle into a bin of white beads salted with red ones, the red beads standing in for defects, and record each day's count. They chanted no red beads, no red beads, and nothing improved. They rewarded the best worker and docked the worst, and the next round the star came out worst. It was never the person, it was the variation baked into the system. Pair that with Michael Gerber's idea of building something to be duplicated 5,000 times, and you see it: duplicate identically and you get predictable results, start tinkering and you invite the variation back in. That was the beginning of my scientific advertising approach, choosing predictable results over the emotional pull of I like red or that's our branding.

Show notes: https://deanjackson.com/podcasts/tol/039-how-to-turn-your-advertising-from-a-slot-machine-to-a-vending-machine/

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

(Great Lifestyle + Money) × Time to Enjoy It = True Success (to me..) Jul 11, 2026

Show notes

Every morning we're here at Honeycomb getting into a real routine, and it reminded me of Scott Adams, the Dilbert guy, who did a live broadcast at 7:30 every day for years. He'd get everybody watching to grab their coffee at the same moment and take what he called the simultaneous sip. So consider this a nod to him. Grab your coffee and enjoy this moment, because one of the big insights coming out of these journals is simple: right now, today, these are the good old days.

Somewhere between August and November of 1996 there's a page where I asked myself, if I could create the perfect lifestyle, what would that look like? I wasn't being specific, I was thinking about what I'd want perpetually. A cool place to live with great furniture in a great environment. A nice car to drive, which back then I wrote down as a Porsche 911, and there's a spoiler coming on that one. Three-day weekends. Evenings off, which came straight from real estate feeling like a game of Tetris you had to stay responsive to. Five or six trips a year. Golf whenever I want. Great food. Money to do whatever I want socially, nothing crazy, just never being in a spot where I can't.

The one I starred was time to enjoy my life. Time was and is and always will be the important thing to me. Good friends, a healthy lifestyle, money to test new ideas in advertising and business, because my joy comes from cracking the code, figuring out something new that actually works. Then a personal assistant and concierge, a financial manager, and these one-hour businesses Eben and I dreamed about, where we'd create and prove the thing, then pair with operators to run it while we spent an hour a week guiding it. Reading it back, I can't punch a single hole in it. I want all of it today just as much as I wanted it then.

Jerry Ballinger had a formula I love: a great lifestyle plus money, multiplied by the time to enjoy it, equals true success. That's exactly right. This little page of vignettes became the genesis of something that evolved into a much bigger part of the journals down the road. Dan Sullivan wrote what do I want in his journal every day for 25 years. If you can get crystal clear on what you actually want, you'll figure out how to make it happen. And it's okay, because it's what you want. You don't have to want what anybody else wants for you.

Show notes: https://deanjackson.com/podcasts/tol/038-great-lifestyle-money-time-to-enjoy-it-true-success-to-me/

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

Inside My 1996 Content Factory vs Today Jul 10, 2026

Show notes

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/

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

I Know Exactly What To Do... So Why Don't I Do It? Jul 09, 2026

Show notes

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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I Almost Can't Believe I've Gotten Away With This Daily Schedule Over 30 Years Jul 08, 2026

Show notes

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 Predict These 7 Business Categories Will Survive & Thrive In The NEXT 30 Years Jul 07, 2026

Show notes

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/

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

Stop Trying to Convince People. Just Start Telling the Truth & Watch What Happens… Jul 06, 2026

Show notes

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/

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

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