Thinking Out Loud with Dean Jackson

Latest Episodes:

Creativity Isn't a Gift. It's a Formula. Aug 04, 2026

Show notes

Good morning.

I can't stop thinking about yesterday's page.

We found the genesis of the 8 Profit Activators, sketched around a pool in 1997... and I've been sitting with it ever since.

Because what I actually walked away with that afternoon wasn't a marketing framework.

It was a lens.

Everything I do with a business, thirty years later, still gets run through it. I can look at somebody's business, spot where the big opportunity is, and immediately have thirty years of ideas ready to combine with it.

That's been my magic. My winning formula.

And having your own frame of reference is the whole thing. Not borrowing somebody else's. Having one of your own that everything passes through.

Now here's where my head went next.

Max Martin.

He lives in Sweden. The list of people who've written the most number one songs on the Billboard charts goes Paul McCartney, then Max Martin, then John Lennon.

His first top ten was 1997. Same year as this journal page.

Backstreet Boys. Britney. NSYNC. Pink. Katy Perry.

And if you listen closely, they're all the same song.

Not the melody. The chassis.

The first six seconds is a distinct sound. I call it the ooh, turn it up moment... the thing that makes a teenager lunge for the dial the second it comes on.

Then the first verse. Singsongy, one octave, so easy you're singing along before you know the words.

And inside 35 seconds you're into the chest voice, anthemic chorus.

Every single time.

He didn't write hit after hit because he's a creative person who gets visited by the muse. He worked out a chassis, and then he built on it.

Which is exactly what I'd done with a business.

Take the seven categories where people actually spend money. Their home, their auto, their money, their food, their health, their kids, and them.

That's durable. That's not changing.

Wayfair figured out a chassis too. One hyper-focused ecom brand per thing. All bar stools. Grandfather clocks. Ottomans. Speaker racks.

Same chassis. Different body on top of it.

So... is there a formula for having ideas?

I think there is, and my friend Chad Jenkins has the cleanest version of it. He calls it IC3. Three C's.

Collect. Go read, watch, pay attention, expose yourself to things. Take input in on purpose.

Combine. Run what you collected through the framework you already have. Your lens.

Create. That's the part everybody thinks is the whole thing.

But it's the third step. It's never the first one.

There's no mystery to being creative. It isn't that some people are creative and you're not.

Collect, combine, create. Do the steps and the ideas turn up.

And honestly, that's all I'm doing here. I've got 160 of these journals and we're only on number four. Everything that came after is thirty years of running things through the same filter.

I got a funny email from Rick the other day. Dean, question. Are you saying you can teach me to make fat stacks by hanging out at a pub drinking coffee like you?

And I laughed to myself, because... yes. That's exactly what I do.

Every idea I've ever had, and every dollar I've made in thirty years, went through my brain and my pen and onto a journal page before it ever went out into the real world.

So I'm running the 50-Minute Profit Finder. Free, live on Zoom, and I'll walk you through the exercise myself.

Bring a pen and something to write on. We'll go looking for the lowest hanging fruit in your business, and probably some fruit you didn't know was there.

And here's your nudge for today.

Open a page and write down your chassis. The handful of things you run every new idea through.

If you can't name it yet... that's the most valuable thing you could work out this week.

Show notes: https://deanjackson.com/podcasts/tol/062-creativity-isnt-a-gift-its-a-formula/

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

The Poolside Sketch That Still Runs My Whole Business Aug 03, 2026

Show notes

Good morning. This is a good one today.

I've been going through these journals hoping to find the genesis moments. The pages where something I'm still using thirty years later first showed up.

Today is one of those days.

You know the Beatles documentary? There's a scene where Paul is sitting there strumming, working out Get Back, making up the words as he goes.

That's what this page feels like.

Early 1997. Me, Eben Pagan and Joe Stumpf, sitting around the pool at Joe's place in Encinitas.

And here's what I'm realizing the more I go back through all of this... every idea worth having was at least three things combined.

Here were the three.

One, storyboarding. Laying something out in sequence so you can see the whole journey at once.

Two, a book I was reading called The Loyalty Effect. Its whole frame was that people climb a ladder. Prospects, shoppers, customers, clients, advocates.

Three, the question I kept chewing on. What are we actually doing at each rung to move somebody up?

And then I added one the book didn't have.

What is somebody BEFORE they're a prospect?

They're a suspect.

So I storyboarded it. Seven steps.

Select your target market.

Compel prospects to call you.

Educate and motivate them to meet with you.

Present your unique service offer.

Deliver world class service.

Provide after-sale service.

Nurture lifetime relationships.

Read those back. That's the 8 Profit Activators, near enough word for word, thirty years early.

Number one became select a single target market.

Number five became deliver a world class experience. Not just the result, but the way it feels to get it.

And I added an eighth. Orchestrate referrals.

Which is a different animal than nurturing lifetime relationships. Nurturing is staying in someone's life. Orchestrating is engineering the introduction.

The way I worked it was always the same. Take one step and list everything that sits underneath it.

What do we need to do to fully select a market?

What do we need to do to compel somebody to call?

Because the moment they call, they've moved. They're not a suspect anymore. We know who they are.

Then you educate and motivate, because you can't present your unique service offer until you've got somebody's full attention.

Here's what actually strikes me about the page, though.

None of it was invented that afternoon. It was assembled.

I was reading constantly, taking things in, processing them in my journal. And then two of them bumped into each other on a page.

That's the whole trick. That's all it is.

One mental model, sketched by a pool in 1997, is responsible for basically everything I do with a business now. It's what a Breakthrough Blueprint gets built on.

So here's what I'd have you think about.

Are you paying attention to what you're taking in? Are you running it against the things you're already doing?

Are you writing any of it down somewhere the pieces can find each other?

Because that's how you end up with your own intellectual property instead of somebody else's.

I got a funny email from Rick the other day. Dean, question. Are you saying you can teach me to make fat stacks by hanging out at a pub drinking coffee like you?

And I laughed to myself, because... yes. That's exactly what I do.

Every idea I've ever had, and every dollar I've made in thirty years, went through my brain and my pen and onto a journal page before it ever went out into the real world.

So I'm running the 50-Minute Profit Finder. Free, live on Zoom, and I'll walk you through the exercise myself.

Bring a pen and something to write on. We'll go looking for the lowest hanging fruit in your business, and probably some fruit you didn't know was there.

And here's your nudge for today.

Open a page and put two things on it that have never been in the same room. The book you're reading and the problem you're stuck on.

That's where the next thirty years starts.

Show notes: https://deanjackson.com/podcasts/tol/061-the-poolside-sketch-that-still-runs-my-whole-business/

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

You Can't Want What You Want Until You Know What You Want Aug 02, 2026

Show notes

Good morning.

Yesterday I said it's okay to want what you want.

Today is the harder half. Actually knowing what that is.

Because after I made yesterday's video I sat down for a couple of hours and wrote the whole thing out. Every vision. Crystal clear.

And there's something almost magical about writing it down. Your mind gets to hear you say, I want this.

Dan Sullivan has a book called Wanting What You Want.

Every day for 25 years he opened his journal and wrote the same question. What do I want?

He missed about 12 days in the whole 25 years.

He started because he noticed the situations he'd landed in were the ones where he'd never been crystal clear on what he wanted in the first place.

So that's where I'd start you. Open the page and ask, what do I want?

And don't limit yourself.

Now, going back through my own journals, the same few flavors of that question keep showing up.

First one is my favorite. What do I want my days to look like?

I write them as vignettes. Painting the picture of the day. The environment, the pace, the way things flow.

And you really can't go wrong attaching your variety to the things that are stable.

Because the rhythm of existence is a constant. There's always going to be a morning. There's always going to be sleep.

That structure isn't going anywhere in the next 30 years, so hang everything you want on it.

Second one is your environment.

When somebody buys an apartment complex or a commercial property, they walk the whole thing with a clipboard and write a property improvement plan. Every single thing that could be better.

Do that with your life.

I keep a page in my journal called better ideas. Anything I notice that could be improved goes on it.

That's where the garbage can by the door of my car came from. Tiny thing. But now it's easy to grab it and empty it, and a problem I hadn't even named just stopped existing.

Walk around with that eye. What would make this better? What would solve this?

Third one is pure fun. The wish list.

The Christmas list. The supermarket spree where you fill the cart with anything you want.

You get a little dopamine hit just imagining having them. That's fine. Write them down anyway.

Then there's the quadrant. If you only do one of these, do this one.

Draw a cross on the page.

Personal satisfactions. The things that genuinely make you happy.

Personal dissatisfactions. The things you don't want in your life, and how to spot them while they're happening.

Professional satisfactions. The work you're happiest doing.

Professional dissatisfactions. The work you'd be glad to never do again.

That lines up almost exactly with Dan's idea of your unique ability.

I'm rereading a Tom Peters book right now, and he cites a survey where executives did a version of this.

They listed the activities that light them up. Then the ones they can take or leave. Then the ones that drive them crazy.

I call them the verbs. All the things you actually do with your time.

Here's what the survey found.

20% was high value work that made them feel great.

60% was mundane. Take it or leave it.

20% was driving them crazy.

That list becomes your working document. Now you know exactly what to drive out.

And this is the beautiful part of being an entrepreneur. You have the power to design whatever you want.

It's okay to want what you want. But you can't want what you want until you know what you want.

Which starts with a pen, some paper, some time, and some thoughtful directed thinking.

By the way, while I was sitting here reading this page back, a bird pooped on my journal. So that's how the morning is going.

One more thing.

Every idea I've ever had, and every dollar I've made in 30 years, went through my brain and my pen and onto a journal page before it ever went out into the real world.

So I'm running the 50-Minute Profit Finder for the first time. Free, live on Zoom, and I'll take you through the exercise myself.

Bring a pen and something to write on. We'll go looking for the lowest hanging fruit in your business, and probably some fruit you didn't know was there.

And here's your nudge for today.

Open a page and write, what do I want?

Then keep going until you can see it.

Show notes: https://deanjackson.com/podcasts/tol/060-you-cant-want-what-you-want-until-you-know-what-you-want/

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

It's Ok To Want What You Want [Here's How To Get It] Aug 01, 2026

Show notes

Good morning.

Journal number four, somewhere around February 1997.

Quick note before we get into the page... if you're going to journal, start every entry with where you are, and the date, and the time.

I didn't do that back then. So now I'm sitting here surmising when things happened.

I do it every single day now. Give your future self a frame of reference.

Okay. This page is about a month into moving to Florida, and what strikes me reading it is how little has actually changed in thirty years.

We still move at 60 minutes per hour. There's still a morning and an evening and sleep in between.

The structure of the day hasn't changed, and it's not going to change in the next thirty years either.

So the only real question is what you put inside it.

Thirty-year-old me had already made his list. Read. Study. Play golf. Scheme. Talk on the phone.

Here's the funny part. That's still the list.

Read. Write. Be on small Zoom groups, or one-on-one with somebody. Develop my projects. Make art, really, is what it is.

Do you ever watch DJ Khaled? There's a guy just living his best life.

And his whole frame is two words. Golf and studio.

That's it. That's the day.

So then it comes down to how much of that thing you actually want to do.

And I think the sweet spot is two or three hours a day. You can be world class at anything with two or three focused hours a day.

When I was playing tennis, that's exactly what it was. School in the morning, then all afternoon was tennis and working out and stretching. The core of it was two or three hours on the court.

Stephen King says the same thing in On Writing. Three hours a day.

The clues are everywhere once you start looking for them.

Josh and I watched Jiro Dreams of Sushi the other night. Third or fourth time I've seen it.

An 85-year-old man with ten seats at a counter in a Tokyo subway station. Three Michelin stars. Three hundred dollars to sit down, booked months in advance.

One craft. Making sushi, making better sushi, innovating with sushi. He talks about waking up from dreams about sushi.

What an amazing life.

And that's what I see all over this 1997 page. The seeds were already planted. I really did know who I was.

It just took a while to weed out everything that wasn't those things.

Back then it was only me. No support team. Now everything administrative is handled, everything financial is handled, the house is handled. There's a designer, there are web people, there are people who work with our clients.

It takes a village to raise my ADHD entrepreneur life.

Which means I get to just do the scheming.

So if you're starting to journal, this is the thing I'd spend the time on.

What do I want?

Because you can have anything you can imagine. That's the joy of being an entrepreneur. You're self-directed.

You get to choose what you focus on, what your life looks like, and more importantly how you're going to contribute.

A woman came up to me at an event once and gave me the most sincere hug. She'd been a client for ten years, a realtor, and her daughter had just graduated college with no student loan debt.

That was only possible because she had an engine fueling her real estate business. Excess capital to do the things she wanted in her life.

That's a bigger reward than the money. By a mile.

I got a funny email from Rick the other day. Dean, question. Are you saying you can teach me to make fat stacks by hanging out at a pub drinking coffee like you?

And I laughed, because... yes. That's exactly what I do.

Every idea I've ever had, and every dollar I've made in thirty years, went through my brain, through my pen, onto a page in my journal before it ever went out into the real world.

So I'm going to run the 50-Minute Profit Finder. Free, live on Zoom, and I'll walk you through the exercise myself.

Bring a pen and a notebook. We'll go looking for the lowest hanging fruit in your business... and probably some fruit you didn't know was there.

And here's your nudge for today.

Open a page and write down the day you actually want.

Then start chipping away everything that isn't it.

Show notes: https://deanjackson.com/podcasts/tol/059-its-ok-to-want-what-you-want-heres-how-to-get-it/

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

How to Get Referrals While You're Still Doing the Work Jul 31, 2026

Show notes

Good morning from Honeycomb.

January 1997. Journal number four. And the heading at the top of today's page is: here's how to get referrals from your listings every single week until they sell.

Thirty-year-old me was pretty pleased with that headline.

But this is the page where something bigger started. The beginning of thinking about the people you're already working with as multipliers.

We call it your multiplier index now. Back then it was just a question... how do I turn this one listing into more than one transaction?

Here's the setup.

Every year the National Association of Realtors surveyed home buyers and sellers on where the buyer came from. Signs. Ad calls. There was no internet yet, remember.

And one slice of that pie chart was direct or indirect referral. Someone who knows someone who knows someone.

18%.

Almost a fifth of the market, and most agents were doing nothing about it. Put it in the MLS, stick a sign in the yard, maybe run an ad. Then wait.

So we built the whole thing around that missing 18%.

It starts at the listing appointment. You show the sellers where buyers actually come from, you show them that slice, and then you ask them for one commitment.

Keep your eyes and ears open for anybody buying or selling a home while we've got your house on the market.

Then you explain why that's going to be easier than they think.

The reticular activator. The part of your brain that notices what's relevant to you right now.

It's why pregnant women see pregnant women everywhere. It's why the day you drive home a new red pickup truck, everybody else got a new red pickup truck today, too.

The sign goes up in the yard, and suddenly they're hearing real estate conversations they'd have walked right past a week ago.

You don't have to convince anybody of this. They already know it's true.

Then you equip them.

We gave every seller little business cards with a picture of their house on them and a recorded message number to call. Property flyers to hand out at work. Little flyers for the lunchroom board.

And by the way... all of our other sellers are out doing the same thing for you.

Now here's the core of it.

We called every seller, every single week, at the same time. Which is just good business. They want to know what's happening.

But the call had a structure, and the structure never changed.

We had six showings this week.

Here's what the agents told me their buyers said.

Here's what sold this week.

Because we framed every listing as a horse race. If somebody's in the market for a house like yours, there are 5, 10, 20 viable options. That's your field. We identify it on day one so you know exactly who you're running against.

Here are the new listings. New competitors just entered your race.

Here's what's coming up. Three showings arranged, an ad in Homes and Land, classified ads running, and this many people called the recorded message.

And we got a referral from the Smiths, another one of our sellers, so I sent them information on your house.

Every week. Same order.

Then you ask one question.

How did you do this week?

And then shut up.

The first time, it's awkward. What do you mean, how did I do?

Well... who did you hear about? Any conversations this week?

But I guarantee you the next time you ask it, they're ready. Oh, John from my office, his brother's looking, I gave him one of the cards.

That's it. That's the whole system.

I wonder how many referrals that generated across the thousands of agents who used it. What I wonder more is how many of them ever actually ran it.

Because it only clicks once you see what's really going on in the transactional period.

While you're building somebody's deck, decks are all they talk about. The neighbors notice. The crew out front gets noticed. They're showing the renderings at work.

Somebody buys a new car and for the next 90 days it's the first thing out of their mouth.

Your customers are having those conversations right now. Whether or not you've given them anything to do with them.

So here's your nudge for today.

Open your journal and ask yourself... how could I create a referral opportunity while somebody is still doing business with me?

And if you can make it self-serving for them, even better.

Show notes: https://deanjackson.com/podcasts/tol/058-how-to-get-referrals-while-youre-still-doing-the-work/

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

9 Journal Prompts for Thinking Through Anything Jul 30, 2026

Show notes

Good morning.

1997, journal number four. By now I'm becoming a professional journaler. I'm really getting into this.

And since I started doing these videos, people keep asking me the same question. What do you actually do in your journal?

Turns out thirty-year-old me already answered it. There's a page in here where I made a list of the things to journal about.

So let's tally them up.

One. Snapshots of life, as it's happening.

That first journal is full of places I'd never been. Palm Springs. I read those descriptions now and I'm immediately back there. You're anchored to the moment.

This journal opens with the drive down to Florida. January. My friend Steve and I left in the most horrible snowstorm, a complete whiteout, 20-car pileups the whole way. We only got as far as Windsor the first night.

I'd forgotten all of it. It's right there on the page.

Not in a dear diary way... well, kind of in a dear diary way. Just the observations you make and the feelings you're feeling.

Thirty years from now, you're going to be thankful you took the time.

Two. Snapshots of the future.

Ultimate scenarios. Writing out a vignette of what it's going to look like when it's done.

My friend Cameron Herold calls it a vivid vision.

What's the picture on the cover of the puzzle box you're trying to put together?

Because the clearer you are on that, the more specific your mind gets about how to make it happen.

Three. Conversations with myself.

Most of the bulk pages in these journals are full dialogues. Me working something out on paper.

And it's the gift you get to enjoy twice. Once while you're doing it. Again thirty years later, when you get to see the way you were thinking.

Four. Mind maps, flowcharts, storyboards.

Visual planning.

I don't want to give it away yet, but there's a very special page coming in this journal. The very beginning of the 8 Profit Activators.

That came out of storyboarding. Flowcharting the process, spotting the benchmarks, then putting some creative thinking against them.

Five. Things that drive me crazy.

I love these one-question pages. Ask the question, then list 5 or 10 or more.

Then pay attention to what keeps recurring. And on your buffer days, come back to the list and ask what you could do to get rid of some of it.

Six. What do I want?

A future shopping list.

A Porsche 911 keeps presencing on mine around this time. Spoiler alert.

And you can point that question anywhere. What do I want in this situation? What do I want for my life? What do I want for my days?

Seven. How can I...

Fill in the blank.

Whenever you pose a question to your mind, you're immediately drawn to fill that vacuum with an answer.

You're querying your brain.

This is 1997, remember. We always referred to our brain as a search engine, and we didn't even know what a search engine was yet.

Eight. The idea machine.

Take one specific segment of the storyboard and get deep. Just ideas around that one piece.

Looking at the home buyer timeline, one of the questions I asked was, how could I create an opportunity for somebody to refer us before the end of the transaction?

Well... think about what's actually going on. Somebody moves into a new house, and for the next 30, 60, 90 days it's the first topic of conversation with everybody they know.

We got a new house. You have to come and see it. We're living over there now. We just moved.

Every conversation they're having is about this new vector in their life.

That's a great time for people to refer.

Nine. Things I've learned.

I read a lot. I've always read a lot. And I'm constantly processing it in the journal so I can distill the best parts of it.

Writing it out by hand reinforces it. And it lets me collide what I'm reading with everything else I'm reading.

The one-to-one future, crossed with the seven things people spend money on, crossed with real estate agents. That combination turned into something really valuable.

People also ask when to journal. It doesn't really matter. It just has to be an integrated habit.

I do it almost every morning. I've got a great environment for it. And I feel lost if I don't have my journal to keep writing things in.

I got a funny email from Rick the other day. Dean, question. Are you saying you can teach me to make fat stacks by hanging out at a pub drinking coffee like you?

And I laughed to myself, because... yes. That's exactly what I do.

Here's what I really realized though.

Every idea I've ever had, and every dollar I've made over the last 30 years, went through my brain, through my pen, onto a piece of paper in my journal, before it ever went out into the real world.

So here's your nudge for today.

Pick one of the nine. Put it at the top of a blank page.

And just start.

Show notes: https://deanjackson.com/podcasts/tol/057-9-journal-prompts-for-thinking-through-anything/

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

Think Big. Start Small. Keep Going. Jul 29, 2026

Show notes

Good morning. This is the big day.

January 1997. Winter Haven, Florida. Journal number four, and the page where I move to Florida full time.

And here's something I wish I'd known thirty years ago.

Back then I was a kid in a candy store. So many possible businesses. So many markets. I always loved finding the edges of a thing... where are the boundaries, how big could this get.

I'd already worked out that there are only seven major things people spend money on.

Home. Cars. Food. Kids. Health. Money. Me.

Everything anybody spends money on fits into one of those seven.

So in the journal I gave myself a page per category, and filled it.

Under home alone: buying a home, renting one, the mortgage, the home inspection, furniture and accessories, electronics, painting the house, paint and wallpaper, carpet, carpet cleaning, garage doors...

That's the thing about a constraint. Put one on a brain that generates a lot of ideas, and it goes and finds everything that fills that bucket.

My ADHD brain loved it. Like a puppy in a field of fresh snow. Everywhere you run, it's untouched.

Then overlay all of it with the one-to-one future. Because the centerpiece of all seven of those is one person. One household. One relationship.

Infinite possibilities.

But here's the part I got wrong.

I spent a lot of time thinking about how big something could be... and a lot less time completing one of them.

Because time moves at the speed of reality. 60 minutes per hour.

Every word on that page had to come through my pencil one word at a time. I can't instantly finish anything.

Now think about Wayfair.

Before Wayfair was Wayfair, they didn't build Wayfair.

They built one complete e-commerce brand that sold bar stools. Only bar stools. Site, infrastructure, all of it, up and running.

Then grandfather clocks. Then ottomans. Then speaker racks. Every category with enough in it to be a big thing on its own.

270 individually profitable brands. Then they rolled them all up and... tada. Wayfair, with everything already built out.

That's the advice I'd give thirty-year-old me.

Instead of thinking about the vastness, think about the depth.

Take one. Build it all the way out. Let it run. Then take the next one.

From the base up, not from the top down.

Because I'd been living in the future for so long, imagining the whole finished thing, that working in the present felt slow. Almost like living in the past.

But your brain doesn't really care what it's working on... as long as it's clear on what it's working on. You get to innovate and imagine inside the one thing you're focused on right now.

So picture where I'd be if I'd taken one of them and built it all the way out. Then another one the next quarter. For thirty years.

That's 120 of them. Done.

That's a very different world.

And here's your nudge for today.

Take one of the things you've been imagining in full... and build it all the way to done.

Show notes: https://deanjackson.com/podcasts/tol/056-think-big-start-small-keep-going/

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

3 Things Your Future Self Will Thank You for Starting Today Jul 28, 2026

Show notes

Good morning.

Forty days and forty nights we've been doing these journals.

And the timing on this one is perfect. We're at the end of December 1996, just about to turn into 1997... and I still can't quite believe we've gotten forty episodes out of a single year.

Doing this has felt like time travel.

I'm reading pages I wrote at thirty. I've just turned sixty. And here's the strange part.

I feel exactly the same.

Same reactions. Same core nature. Nothing about who I am has really moved.

There's no internet in these pages yet. I haven't met most of the key people in my life yet.

But the seeds are all in there.

So before we open journal number four, let me pull out the three things I'd tell you to start today.

Number one. Start the journal.

April of 1996, journal number one. Of everything I've done, that decision has been the greatest gift.

I kept pretty good notes, and that's the whole trick. I read a page and I'm immediately transported back to where I was and what was going on.

Your 2056 self will thank you for starting in 2026.

Number two. Have the dialogue with yourself.

Most of what fills these pages is me talking to me. Thinking about my thinking.

We're pretty smart, you know. Our intuition is right more often than we give it credit for. If we just dig into it and explore it on paper, we come to pretty good conclusions.

I can see hunches brewing in these pages that turned into everything.

There's one coming up in 1997 I can't wait to show you. A question written at the top of the page... what am I going to do about the internet?

The pages are also where I try out my life. The architecture of the days. Lifestyle design, before I had a name for it.

I'd just moved to Florida. Wake up, go for a walk, come home, make some breakfast... and then watch Regis and Kathy Lee.

There was one segment where they followed Regis around for a day. He lived right across the street from the studio. Coffee with Joy, got dressed at home in whatever he was wearing that day, walked over.

Music comes on. And he spends the first ten minutes of the show just recounting everything he'd been doing.

Live on television. The rest of it was just being Regis.

That stuck with me. Because at sixty, what I'm completely bought into is just being Dean Jackson.

Look at my Facebook bio. I'm Dean Jackson. Period. Professionally, period. That's the whole thing.

And that gives me room to do whatever it is I want to do.

There's never been a better moment to just be you. Look at the reach you have now. The community. The options sitting there for the taking. We had none of that in 1996.

Number three. Go a mile deep on one thing.

The biggest impact I've ever had came from marketing and real estate. And these journals are filled with me playing the same game over and over, getting better and better at the micro elements of it.

Then I paired it with Michael Gerber's idea. Build the thing as though you're going to duplicate it five thousand times. Extraordinary results with ordinary people. Systems somebody can plug straight into.

Once I got bit by that bug, that was it. Thirty years of continual practice on the same thing.

That's the whole compounding secret and it isn't complicated. One thing. A long time.

Next up is journal number four. 1997. The transition to Florida.

So let's have a simultaneous sip, to toast the first forty days and forty nights.

And here's your nudge for today.

Get a notebook, and put one page in it... a dialogue with yourself about the thing you can't stop thinking about.

Then keep it for thirty years.

Show notes: https://deanjackson.com/podcasts/tol/055-3-things-your-future-self-will-thank-you-for-starting-today/

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

Do Old-School Free Recorded Messages Still Work Today? Jul 27, 2026

Show notes

Good morning.

Do free recorded messages still work today?

I keep landing on this as I go back through my journals. Circa 1996, that's what we had. Hardly anybody had a website. The ones that existed were cumbersome to build, and most people weren't in the habit of going to them anyway.

But we all had phones. And back then, phones were phones. No distraction.

That's the part I've been thinking about. A recorded message is an immersive focusing device.

Whatever we were doing to generate leads... ads, postcards, any of it... the one thing that got the most people to respond was call and listen to a free recorded message.

Because we had caller ID. And if the offer was call and talk to somebody, nobody wanted to do that.

Those three words made it safe. Free recorded message. You could get the information without feeling like you were about to be sold something.

Eban and I used to make ridiculous infomercials using all the anti-language. Call now, trained salespeople are standing by 24 hours and will rush your auto-debit commitment contract.

We were joking. But the fear was real. And it's still real. Nobody wants to talk to anybody now. Even a phone call feels like an intrusion... just text me, right?

So let's go into the tickle trunk. 1996. The Julie Matthews box.

We were getting busy. Lots of leads, one realtor, no help.

And you know the Michael Gerber idea... treat your business like something you're going to duplicate 5,000 times. Systemize the routine.

So we built a recorded message system for finding and hiring an assistant.

A little classified in the help wanted section, because the newspaper was still how you reached people. Winter Haven busy realtor needs part-time assistant, flexible hours. Free recorded message. And a phone number.

Here's how the actual message opened.

Thank you for calling. My name is Julie Matthews and I'm a realtor with Brokers Realty in Winter Haven. This message is about 2 to 3 minutes long and I've recorded it to do three things.

First, to tell you what the ideal candidate for this position would be like. Second, to give you an idea of what you'll be doing if we decide to work together. And third, to tell you what to do next if this sounds like a match for you.

Read that again and picture it as a landing page with a video today. Same message. Same three promises, right out of the gate.

Then we described the person. Organized. Pays attention to detail. Likes to implement systems for routine tasks. Able to work unsupervised. A caring person who can treat clients like royalty.

Reading it back now, there are probably a few HR violations in there...

Then what they'd actually be doing. Setting up appointments with other offices. Picking up keys, because not everything was on a lockbox yet. Preparing the file, returning the keys, updating the file.

And helping build a practice aimed at a wow experience and lifetime relationships, not just transactions.

Then what to do next. Leave your name, your mailing address, your phone number, and your email address if you have one.

As my friend Terry Hunnefeld would say, that's a sifting and sorting tool. Terry founded the Gold Rush system and took recorded messages to a whole other level in the '90s. I learned a lot from him.

Then the package went out. A photo of Julie. A transcript of the message they'd just heard, so they could read it back and check it still sounded like a match. An application form. A resume request. A stamped return envelope.

And a calendar, with instructions to highlight the hours they'd be available to work... and a highlighter in the envelope to do it with.

Now here's what all of that is really doing.

Half of it conveys the information. The other half sorts for the people who can follow directions.

The ones who sent everything back, complete, got invited to a career night. All of them at the same time.

The message can be a video on a landing page now. That part's easy.

What hasn't changed is the immersive, focused attention. One perfect version of the thing you want to say, cloned, with no distractions, and no saying it one at a time to everybody who calls.

So do recorded messages still work?

They sure do.

So here's your nudge for today.

Take the thing you explain over and over to every new person... and record it once, properly.

Then send people to the recording instead of your calendar.

Show notes: https://deanjackson.com/podcasts/tol/054-do-old-school-free-recorded-messages-still-work-today/

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

Good Marketing Never Gets Old (Proof Inside) Jul 26, 2026

Show notes

Good morning.

I brought some props with me today.

I called it my tickle trunk, the way you say something you assume everybody knows... and I was today years old when I found out not everybody grew up with Mr. Dressup. My Canadian friends will know exactly what I mean.

I keep red archival boxes. Dozens of them. Every project I've done over my whole career, sitting in those boxes.

And this morning I've been in journal number three again. We're at the end of 1996, moving into 1997.

I'd talked in an earlier video about recorded messages... those three magic words, free recorded message. And somebody left a comment saying, oh yeah, those were the good old days. They used to send 20,000 postcards a week with nothing but a call to action to hear a 90-second message.

Here's what I thought when I read that.

These are the good old days.

Because looking back at what we had to work with, the thing that made it all so good was the constraint. Constraints force your creativity.

Print or direct mail. That was the entire menu.

I found the original guide to Winter Haven in the box. Same logo as the guide to Halton Hills I'd made a couple of years earlier, the one that became Toronto and Beyond. Eleven by seventeen, folded down to letter size. A little letter inside from a very young Julie Matthews, circa 1996.

We even put a price legend in it so I wouldn't have to reinvent the whole guide every time the market moved. Just shift the categories.

And every bit of it was laid out by hand. Pasted-up photographs. This is right before real desktop publishing. Getting one of those printed and out into the world was an effort.

But every single one of them pointed at the same thing. Call and listen to a free recorded message.

That was the lowest friction way for somebody to get information without feeling like they had to talk to a real person. And it took the burden off you having to be sitting there to answer the phone every time.

Then came the postcards.

Any time Julie got a new listing, that was an opportunity. We'd mail the neighborhood around that home.

And we didn't send a picture of the house. We told the story.

Do you know what your neighbors at 365 East Thelma Street did last night? It may come as a surprise to you, but they've been plotting for a long time.

Then the whole thing unfolds. They've decided to sell. They listed with Julie because they saw how fast she'd been selling homes around there. Three bedrooms, two baths, pool, almost 3,000 square feet, a family room that measures 30 by 30. Sits on a double lot running all the way from Thelma to Echo, deeded separately, you could build another home on it.

If you know anyone thinking of buying in East Lake Alfred, be sure to tell them about this one.

And the PS. If you're going to sell your own home in the next six months, Julie has a special report called How to Sell Your House for Top Dollar Fast. Call 1-800 whatever, 24 hours, for a free recorded message.

Run that card through the seven-step checklist. Single target market? Yes, the neighbors of that listing. Headline that draws you in? You know what it's about from the first line. Conversational language? It reads like news, not like an ad.

The just sold cards worked the same way. Your neighbor Mrs. O'Brien got exactly what she deserved... and it could happen to you next.

Then we tell you what she deserved. A buyer for her beautiful home, less than 90 days after she put it on the market.

Here's the test I'd use on any of it.

Would you hire somebody to stand at that person's doorstep and say out loud what you've put on your postcard?

You'd never. Most realtors are mailing a big photo of the property, the words JUST SOLD, a logo, a name, and call Julie and start packing.

But a story is a very compelling thing to find in your mailbox.

My favorite proof of that. One of the first times we mailed those cards, Julie got a call from the mailman who'd been delivering them. He'd read one, written the number down, and called her because he wanted her to sell his house.

He and his new girlfriend both had homes to sell, and they bought one together. Three transactions. From the guy carrying the mail.

And none of this is nostalgia, that's the part I want you to hear.

These are still the same postcards we use. To this day. The message is still as relevant as it was in 1996.

We did it for the Mosquito Authority. Your neighbors the Valentes got exactly what they deserved... and it could happen to you next. Then the story about the Valentes getting their yard treated and having a mosquito-free backyard. On the back, the offer. Absolutely positively no mosquitoes in your yard, guaranteed. Period.

And people still call the recorded message.

So do recorded messages still work today? Absolutely.

Do postcards still work today? Absolutely.

They're at the core of any message you want to put in front of a very specific group of people.

The only thing that's really changed in 30 years is that now we can put a QR code on the card next to those same words. More ways for somebody to respond. Same message doing the work.

So here's your nudge for today.

Take the last thing you mailed or emailed to your people, and read it out loud at an imaginary doorstep.

If you'd be embarrassed to say it... go and write the story version instead.

Show notes: https://deanjackson.com/podcasts/tol/053-good-marketing-never-gets-old-proof-inside/

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