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 One Idea Turned a $4M/yr Restaurant Into $11M/yr Aug 14, 2026

Show notes

Good morning.

Most of us set the same kind of goal. Constant and never ending improvement.

Twenty percent better. Slow and steady wins the race.

There's another way to think about it, and I've been carrying it around since 2006.

I read a piece about a gentleman named Gamal Aziz, in a magazine I don't think even exists anymore.

He'd just come over from the Bellagio to run the MGM Grand.

And the first thing he did was pull apart every line item in the hotel. Restaurants. Gaming. Rooms. Entertainment. Conventions.

Every category of revenue, looked at on its own.

Then he asked one question of each one.

How high is high?

Not how do we improve this. What's actually possible here?

Take the restaurants.

They had a flagship restaurant that was perfectly serviceable. Profitable. Nobody was complaining about it.

Four million dollars a year.

And the reasonable question, the one almost everybody asks, is what could we do to lift this by twenty percent.

Gamal asked the other one. And he already knew the answer.

With a celebrity chef and a real destination restaurant, that same footprint could do eight million.

Here's the part I want you to sit with.

He booked the difference as a loss.

Not as an opportunity. Not as something to get to one day. In his mind, the hotel was losing four million dollars a year by not having that restaurant.

He took it to the board. They agreed. They ripped it out.

They partnered with Michael Mina and opened NobHill in exactly the same footprint.

First year... eleven million.

He'd been aiming at eight.

Now let's do it with yours.

You've got different buy buttons. Different things people pay you money for.

Look at each one on its own, the way he looked at each line item.

And ask how high is high.

Not what's realistic. What's possible, with the same framework you're already running?

And by the way, none of this means scaling past what you actually want. You're in control here.

It's your dream. You get to create exactly the business you want.

But carry this question through every line of what you do, and I think we're going to turn up some pretty big opportunities.

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 this Friday at 1pm. 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.

Take your biggest line item. Write down what it's doing now, and what it could be doing.

Then look at the gap between them... and call it what Gamal called it.

Show notes: https://deanjackson.com/podcasts/tol/072-how-one-idea-turned-a-4m-yr-restaurant-into-11m-yr/

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

How to Get New Customers in Any Market in 45 Days Aug 13, 2026

Show notes

Good morning.

I was looking back through 1997 this morning, and there it is. The first time I ever met Dan Kennedy.

And if you've ever had the pleasure of meeting Dan Kennedy, you'll know what a lovable, approachable, huggable kind of guy he is.

I'm kidding, of course.

I was 30. He was maybe 41 or 42, and already a grumpy old man. In the best possible way. That's his thing.

It was a weekend retreat Terry Hunterfeld put on for his Gold Rush members, up in Grand Rapids, Michigan. Dan was the keynote.

Same weekend I met Joe Polish for the first time, as it happens.

A lot of history rooted in one room.

This is one of those seed moments.

I'd been studying Dan for years by then. Subscriber to the No BS newsletter, reading everything he put out.

Because in the early to mid 90s, he was what John Carlton would call action central for this new thing called the information publishing business.

There was no internet yet. Barely the start of one.

So the model was this. Pick a market. Write a full page ad. Run it in a magazine those people already read.

Get them to respond for a free report... then mail them a sequence of three things... then sell them a $697 or $897 marketing kit.

That's how Joe Polish started. Ads in a carpet cleaning magazine.

Terry was doing it. A lot of people were doing it.

And it's not far off what the Guide to Halton Hills was for me. Have people respond, then keep on educating them.

Here's what Dan gave us from the stage that weekend. Three things.

They're foundational, and they've held up for thirty years.

Number one. The right message.

That's where it starts, and it's the most important of the three.

He called it the USP. The unique selling proposition. You don't hear the term as much now.

It's the answer to one question. Why should I choose to do business with you over every and any other option that I have?

Get that right, get it so you can clearly say what you're going to do for somebody, and you've got your message.

Number two. The right market.

We don't want to broadcast your message out to everybody.

If you can carefully select the right people to receive it, that's 50% of the job. Right there.

That's exactly why the information publishing model worked so well. The ad ran in the carpet cleaner magazine. The realtor magazine. The homes magazine.

The people you can help were already gathered in one place.

And if you've got what we call visible prospects, you can simply get a list of them.

You can select them geographically. Geodemographically. Psychographically.

Fancy sounding words for something very simple. You can pick people by where they are, or by what kind of people they are.

If somebody rents, they're living in an apartment complex or a rental home in a particular part of town. That's selectable.

The clearer you can get on it, the better.

Number three. The right media.

Once you know what the offer is, and you know who's the best person to make it to, now you can choose the best way to get in front of them.

In 1997 that meant the right magazine, the right newspaper, the right classified section, or direct mail straight to the exact people you wanted.

There was a whole industry around list brokering and list selection. You could find precisely who you were looking for.

Message. Market. Media.

Then he amplified all of it with something I went away and implemented immediately.

He called it plant the seed farm.

Once you've picked the group of people you're trying to reach, here's how you get dominant market presence in 45 days. A three step letter campaign.

The way he first worked it out was something he called the Giorgio letters.

Picture a restaurant. You pick the people you'd most want to come and eat there.

And you make an offer that's specifically appealing to them. In this case, a romantic dinner for two. Wine, roses, the whole thing.

The letter arrives from Giorgio, the director of romance at Giorgio's Italian restaurant.

He invites you in, and he takes care of everything. You can prepay for all of it.

You arrive and there's the bottle of wine, the roses, the candlelit table, a beautiful meal, dessert. All handled.

And you get to be the hero.

If they don't book, letter two makes the same offer a different way.

And letter three is the one titled can this marriage be saved? Without the romance, none of the rest of it happens.

Three steps instead of one. That intensification was the whole win.

I took that idea and built a postcard campaign out of it.

Getting in front of people who were going to sell their home in a particular market area... right ahead of the time when most of the activity happens.

So instead of mailing every month for 12 months, we mailed for the 8 weeks leading into the peak.

Into the fall, when people list. And into the spring, when people list.

Same people. A fraction of the mailings. All of it landing in the weeks that decide the year.

It's fun to look back and see the seeds of everything sitting right there on the page.

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 this Friday at 1pm. 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.

Message, market, media... in that order.

Write down who you'd most want to reach, and where they're already gathered.

Show notes: https://deanjackson.com/podcasts/tol/071-how-to-get-new-customers-in-any-market-in-45-days/

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

How To Use Constraints as a Multiplier Aug 12, 2026

Show notes

Good morning.

Rules sound like a limiter.

Constraints on how you do business, on who you'll take on, on how long you'll work at something... they feel like they can only cost you.

They're the opposite.

They're one of the greatest multipliers you've got, because they quietly remove the opportunities that were never going to work out anyway.

Let me show you what I mean.

There's a page in my 1997 journal titled Rules for Good Listings.

I'd been practicing this in my own business and overlaying it on everything I was learning at the time.

Deming, on the stability of a system and taking the friction out of it.

And my own experience, which was simpler than that. When a listing didn't work out and I went back and looked at why, there was usually a pattern.

Here's the uncomfortable part.

In the back of my mind, I usually knew. Right at the start, I knew that one wasn't set up to work.

Now, before the rules, the thing that makes any of this possible.

When you've got a system that generates all the leads you need, you stop operating out of scarcity.

You've got abundance instead. And abundance means you get to be selective.

You can't set standards for who you work with until you've got more people than you need.

That's really what the lead generation is for.

So here they are. And read them as clients or customers rather than listings, because that's the whole exercise.

Number one. Geographic area limits.

In my final years selling real estate, the tighter I drew my area, the more money I made.

We could theoretically have covered Caledon and Hillsburgh and Erin and every outlying town.

Choosing to focus on Georgetown and Halton Hills was a freeing decision. I didn't have to stay on top of the inventory anywhere else.

Number two. At least neutral in condition, or willing to get there.

Some of the listings I took early on were dumps, or so packed with stuff you couldn't see the house.

When you're starting out you take them anyway, because it's a foot in the door.

Neutral just means clean and clutter free. I'm not talking about renovating. I'm talking about nobody walking in and being repelled by the work ahead of them.

Number three. Motivated to move, and in agreement.

The best situation is somebody with a job transfer who has to be in Calgary by a certain date.

Motivated, and both of them excited about going.

If one of them is driving the move and the other one really doesn't want it, the one who doesn't want it can quietly make sure it doesn't happen.

Number four. Priced within 3% of the selling price. No more.

I wanted to work with people who wanted to sell, and I wanted the house sold quickly.

The homes that sell faster and for more money are the ones priced closest to what they're actually worth.

Number five. Able to afford the move.

People have a dream of the bigger house or the place out in the country, and sometimes the math just isn't there.

If the whole thing depends on their house hitting a number, everything can fall apart very quickly.

Number six. Willing to participate.

Willing to do the things that give the house its best chance. When I showed them how to tap into the 18% of homes that sell by direct or indirect referral, they were on board.

Number seven. Listed for 90 days only.

This was a big one, and the constraint was on me as much as it was on them.

My home selling system was a system that got homes on the market and sold in under 90 days.

The temptation is to take an overpriced listing on a six month or a one year term. We'll test it at your price, and if it doesn't sell we can revisit it.

That's permission to be lazy. For both of you.

And saying you'll only take it for 90 days does something else. It tells them you mean the price you just recommended.

You've seen more homes than they have. You know what the market is doing right now, especially if you're concentrated in one area.

So when they want to test it high, being unwilling to sign for six months is the most reassuring thing you can do.

Number eight. Easy to show. Lockbox, no restrictions.

No we can't show it when we're not home. No we have to be there. No only on these days.

It needs to be available when buyers want to see it.

Number nine. A winning story.

I've told you about Jerry Spence, and the way we'd tell the story of a listing so a buyer had a reason this was the house for them.

The losing stories are the ones you hear all the time. We're not giving it away. We don't have to sell. If they want it they can pay our price. We've put a lot of money into this house.

All resistance. No power.

The winning stories sound like this. We got our dream job in Calgary and we have to be there by the end of next month. We found our dream home in the country and we need to sell this one to get it.

You'll win more if you let them feel like they're winning.

Tim and Darlene's townhouse sold for more than the asking price that way. We told people the situation, the dilemma, and what the house was worth.

Number ten. No roadblocks.

Nothing standing between where you are and getting this thing sold.

Now translate all of that into your business.

Is there a geographic constraint that would help you?

Is there a minimum standard somebody has to meet before you'll work with them?

Do all the partners or decision makers have to be on board?

Is there a budget somebody needs to have?

Is there a time frame you'd hold yourself to, out loud, in front of them?

Here's the exercise.

Take a page in your journal and write the rules that have to be true for your very best clients. The ones you get the very best outcome for.

Then use them two ways. As selection criteria... and as the thing that keeps you grounded when you're tempted.

It sounds paradoxical, winning by having constraints.

But the constraints are exactly what free you up to go as fast as you can.

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 this Friday at 1pm. 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.

One page in your journal. Rules for good clients.

Start with the last one that didn't work out... and write down the rule that would have kept you out of it.

Show notes: https://deanjackson.com/podcasts/tol/070-how-to-use-constraints-as-a-multiplier/

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

How to Write Headlines That Attract Your Very Best Prospects [Samples Inside] Aug 11, 2026

Show notes

Good morning.

Have you ever seen one of those bus benches that says bus bench advertising works?

You can't deny it. They've got you.

You're sitting there looking at a bus bench, reading a message on a bus bench, wondering whether bus benches work.

Well. There's your answer.

I was driving just outside of town not long ago and there was a billboard half hidden behind some trees.

It said billboards work.

And underneath, even behind trees.

That was the exact thought I was having, and it answered it before I'd finished having it.

That's a headline doing its job.

Yesterday we talked about saying what you do in three or four words.

Think of the headline as the amplifier sitting on top of that.

The three or four words tell somebody what this is. The headline makes them feel like it's for them.

Stop Your Divorce. You know instantly what that is.

But the headline we actually wrote for the book was longer.

How to stop your divorce or lover's rejection, even when your situation seems hopeless and you're the only one who wants to stop it.

Look at what that little bundle of words does.

It gives clarity. It gives hope. And it gives somebody the sense that this was written for me.

That's the whole job.

I've been writing headlines in my journals for as long as I've kept journals. Pages and pages and pages of them.

Thousands, for sure.

Because 80% of the work is in the headline.

I was looking at a page from 1997 this week and some of them I still use to this day. The ones that made the cut have little check marks beside them.

Why buyers love model homes, and how to make your house show like one.

How to find out what your house is worth, for free, over the phone.

How to avoid the six most expensive mistakes smart people make when they buy or sell a home.

How a 25 cent upgrade could net you an extra $500 to $1,000 more when you sell your house.

That last one started out as a little known designer secret that could net you an extra $500 to $1,000.

The secret was a brighter, warmer light bulb. I'd seen a study showing brighter homes sell for more money.

Which is really what all of this is. Stacking the evidence. Building the case for why somebody should work with you.

Now here's the useful part.

You can take any headline that works on you and deconstruct it. Look at the pattern underneath the words.

There's a good chance it starts with how to.

How to is a great way in, because it forces a transformation into the sentence.

Then there's when to.

When to put your house on the market to get the best possible exposure.

When to book your summer cottage rental to get the best possible price. When to book a resort. When to book an airline ticket.

Same shape. Different business.

Then there's why.

Why buyers love model homes. Why most real estate advertising will never sell your house, and what to do about it.

Why kids love this, and how to get them to do that.

Anytime you can get on your prospect's side of the table, helping them do the thing they already want to do, you've got a real advantage.

And then there's the one that reaches in and takes the objection away.

How to sell your house for nothing down and still get all cash at closing.

People hear nothing down and think that means there's no money in it for me.

So the headline removes the hesitation before they've said it out loud.

Same move as the billboard behind the trees.

Headlines are everywhere, by the way.

Eban and I used to play a game with the magazines. We were probably two of the only men with a subscription to Cosmo. Cosmo, Women's Day, Homemaker...

When a new one arrived we'd each independently write every headline we could imagine off the covers. Then compare. Then look for the patterns and ways to fill them in.

The covers were the prompt. The patterns were the point.

Here's the thing to hold onto.

The headline is the minimum requirement. If you can't capture somebody's attention there, nothing else you say is going to matter.

So if I could gift you with the energy and the curiosity and the discipline to go and do this exercise, I would.

What would it take to write 25 headlines for your business? Two sheets of paper.

Not 25 good ones. 25.

The good ones only turn up after you've written down the obvious ones and got them out of the way.

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 this Friday at 1pm. 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.

Two sheets of paper. 25 headlines.

Start them with how to, when to and why... and don't judge a single one of them until all 25 are on the page.

Show notes: https://deanjackson.com/podcasts/tol/069-how-to-write-headlines-that-attract-your-very-best-prospects-samples-inside/

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

How To Say What You Do So Clearly It Sells Itself Aug 10, 2026

Show notes

Good morning.

If you only had three or four words to describe exactly what you do... what would they be?

Not a tagline. Not a mission statement.

Three or four words that make exactly the right person stop.

I was looking back through a journal from April 1997 and that's the question I was chewing on.

I'd been studying copy hard that year, and Jeffrey Lant's four most important words had gotten into me. You. Get. Benefit. Now.

Once you've got that filter you start running everything through it.

And I grew up in Toronto, where a man built an entire empire on four words.

I buy your gold.

If you're from Toronto you already know I'm talking about Russell Oliver.

He blanketed the city with radio and television. Over a million dollars a year in advertising at the time.

Booming voice, South African accent, holding up cash. I'm Russell Oliver, and I buy your gold.

Your old broken gold. Your gold chains. Your gold teeth. Fourteen karat, twelve, ten. I don't care what it is. Bring it in.

He was one of the most famous people in the city. Everybody knew where to go if you had gold to sell.

Four words did that.

I called him up in 1997 because I wanted to interview him for our By Referral Only magazine.

Quick aside, because it's worth more than it looks. Having a media property is a wonderful gateway to people.

A podcast. A magazine. A recording. Anything.

That's how I met Robert Cialdini. That's how I met Don Peppers and Martha Rogers, who wrote The One to One Future.

I just called them up. Most people say yes.

Anyway. I started thinking about all the places I've used a few words like that since.

Stop Your Divorce. You know exactly what that book is the second you hear it.

Convert More Leads. Get More Leads. Money-making websites. Money-making marketing.

I had a friend, a designer on our team, who did beautiful pencil portraits. We made him little business cards with one image and one line.

Original pencil portraits. Ninety-nine dollars.

He handed those out everywhere and people called him to commission portraits. I don't know what the cards cost... whatever it was, the return on them was ridiculous.

So here's the exercise.

What's the best way to say what you do in three or four words?

Look for nouns and verbs and benefit. That's where the power is. It runs all the way through Cash Copy.

And if it takes six or seven or ten words to get there, fine. The point is the condensing, not the counting.

Now here's why it matters more than it looks.

Get those words right and people are drawn to you immediately, because they see themselves in them.

Get them wrong and it doesn't matter what you say next. Nobody's paying attention.

This is the part I'd sit with.

They don't just roll off the tongue.

It's not the first three words that come to mind when you think about your business.

It's pages and pages of work. Getting inside your prospect's head the way we did yesterday, then condensing all of it down to a laser point.

What do they really want? How few words can I say it in?

Stop your divorce. Three words, worth millions, because they speak to exactly one person.

All that thinking, and what you've got to show for it is three or four words.

That sounds like a disproportionate amount of effort.

It's completely worth it.

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 this Friday at 1pm. 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.

Write down the three or four words you'd use for what you do right now. Whatever's already in your head.

Then spend twenty minutes trying to beat them.

Nouns. Verbs. Benefit... and the one person who'd stop dead when they read it.

Show notes: https://deanjackson.com/podcasts/tol/068-how-to-say-what-you-do-so-clearly-it-sells-itself/

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

How to Figure Out Why People Actually Buy Your Stuff Aug 09, 2026

Show notes

Good morning.

What if you prepared your marketing the way an attorney prepares a case?

Not sat down to write an ad. Prepared a case.

That's where my head was in March of 1997. Journal number five.

I was reading How to Argue and Win Every Time, and it put me into a completely different way of thinking about the people I was trying to reach.

Page ten of that journal, there's one question written at the top.

What is the secret for getting listings?

Every waking thought I had was pointed at real estate agents back then. But the question works for anything.

What's the secret for getting new deck builds. New lawn customers. New clients.

Underneath it, six questions I worked through with my pen. Here they are.

First one. What reasons would somebody have to do this at all?

For me that was, what reasons would people have to sell their homes?

Moving up to a bigger house. Building a better one. Finally buying in the neighborhood they've always wanted. The lakefront house.

Or the other direction. Downsizing. Retiring into assisted living.

Then the ones nobody puts on a brochure. Money problems. Divorce. A job transfer. Somebody dies. Health changes.

I listed all of them.

Because every one of those is a different conversation.

You don't talk to somebody chasing their dream house the same way you talk to somebody who has to sell one.

Those aren't one market. They're different target markets wearing the same label.

Second. What are they going to consider first?

I thought about it and realized nobody wakes up motivated to sell a house.

They're moving toward the new one. The lakefront place, the house in the country.

Selling the one they've got is only the mechanism that gets them there.

Worth knowing which end of that you're talking to.

Third. What methods could I use to reach these people?

Direct mail. Postcards. Telephone. Newspaper ads. The real estate publications.

That's 1997, so look at what's not on the list. No Instagram, no Facebook, no YouTube, no Google. No email. Not even the internet.

Those were the megaphones. Every one we had.

Whatever your version of that list is today, write it out... because the message and the megaphone get built together.

Fourth. What are the best methods being used right now?

The collected wisdom of your industry. What everybody already does.

Realtors chased expired listings. Called for sale by owners. Cold calls, farming an area, door knocking, evaluation certificates.

Financial advisors run the dinner seminar. Invitations go out, everybody comes down to the steakhouse, there's a presentation, a few of them book a meeting.

That's the baseline. You have to know it before you can step off it.

Fifth, and this is the fun one. What new ideas could work here?

I wrote down: what about the houses right around a home that just sold?

That became a whole program called The Listing Next Door. The twenty homes surrounding a sold sign.

Another one. Geographically complementary areas. Not asking a neighborhood if they want to sell... but marketing it to the people already dreaming about moving into it. Townhomes to detached. Condos and apartments to starter homes.

And the one that actually started my career. A telephone research survey.

Not calling to get listings. Calling to status people.

Mr. McQuade, it's Dean Jackson calling from Royal LePage. We're conducting an area market survey, I wonder if you'd have just a minute to be included.

They'd usually say no.

And I'd say, it's only five questions, one minute, I promise.

Then they'd say yes.

That's rejection and retreat, straight out of Cialdini. They turn down the bigger thing, so you retreat to the smaller one.

Five questions. Have you lived in Georgetown more than five years. How many years in your current home. Where did you live before. How did you happen to choose Georgetown. And if you were to move, would you stay in Georgetown or leave... and when would that be.

That was the whole call.

Every hundred people I called gave me the ones looking to sell right now.

But it also gave me a record of everybody friendly who'd told me roughly when they were going to move. Two years out. Three years out.

That's the long game, and hardly anybody plays it.

Sixth. What's already rolling around in their head?

Somebody thinking about selling wants to know what their house is worth. That's the number that tells them whether the move is even possible.

What do buyers look for now. How do I get the house ready. What's it really going to cost me to move up.

Somebody thinking about a deck wants to know what decks cost. What the options are. Wood, or the fiber stuff they've been hearing about.

Answer the questions already going on in their mind and you've cleared the path for them to do business with you.

That's it. Six questions, a pen, and a page.

You come out the other side with the raw material to write anything.

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 this Friday at 1pm. 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.

Write question one at the top of a page. What reasons would somebody have to want what I sell at all?

Don't stop at three. Get to ten...

Then look at how many different people you've been talking to as if they were one.

Show notes: https://deanjackson.com/podcasts/tol/067-how-to-figure-out-why-people-actually-buy-your-stuff/

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

The Easiest Way to Sell a "Horse" [Details Inside] Aug 08, 2026

Show notes

Good morning.

Sometimes the easiest way to sell a horse is with a sign that says horse for sale.

That was the peak thinking in my journal in 1997... and I still use it every week.

Here's where it came from.

When I first moved to Florida I drove past the same house every day on the way to the golf course.

The woman who lived there had a little sign stuck in her front lawn. Tupperware sold here.

That's it. That's the whole ad.

If you're looking for Tupperware... there it is.

It stuck with me because it's crystal clear. Nothing to work out.

Now jump forward to San Francisco.

Eben Pagan and I were speaking at an event about direct response ads, and how different they are from clever image ads.

Afterwards a sales rep came up to us. He was selling loft condos for a developer and he was frustrated.

He showed us what the developer was running. A full page in the San Francisco Chronicle real estate section. Twenty thousand dollars a week.

The ad was an overhead drawing of a turtle shell.

One arrow pointing at the turtle's head. This is you.

Another arrow pointing at the shell. This is your new loft.

Little logo at the bottom. That was the entire ad.

You can picture the meeting where that got presented. The developer's son ran the marketing, his designer friend came up with it, everybody in the room said isn't this clever.

And the lofts sat empty every weekend. Nobody came.

So we wrote him a classified ad instead.

SOMA. Really cool loft. Details on voicemail. And the phone number.

That's all of it.

Two things in there were deliberate.

We wanted it to read like one person selling one thing, not a developer with a marketing budget.

And we said details on voicemail rather than free recorded message or 24-hour hotline. Same mechanism. Completely different feeling.

Here's the part I'd underline.

The job of the ad isn't to sell somebody the thing.

The job of the ad is to sell the next step.

All I wanted was for somebody to call and listen to the message. That's the only thing it had to do.

And then the message only had one job too. Get them to come and see the loft, or leave their name.

One insertion. Under two hundred dollars.

Twenty-eight people came to the lofts that weekend.

The twenty thousand dollar ad brought nobody.

I see this everywhere now that I know to look for it.

I was in Toronto and there was a little sandwich board out on the sidewalk. Delicious coffee this way. An arrow pointing down an alley.

That's the whole thing.

We've got it easier than we did in 1997, too. Back then the next step was call and listen to a recorded message. Now it's click here.

So here's the question.

What's the plainest way you could say what you actually sell... and then say click here?

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 this Friday at 1pm. 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.

Take the ad, or the page, or the email you're currently using to get people to take the next step.

Write the horse for sale version of it. One line saying plainly what it is... one line saying exactly what to do next.

Then see which one you'd actually respond to.

Show notes: https://deanjackson.com/podcasts/tol/066-the-easiest-way-to-sell-a-horse-details-inside/

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

How To Stop Your Best Ideas From Dying in Your Notebooks Aug 07, 2026

Show notes

Good morning.

Quick question before anything else.

How many of the things running your business today started as an idea you had years ago?

I bet it's more than you think.

Now the other side of it.

How many ideas are still rolling around in your head that never made it out into the world?

That one's probably more than you think too.

This is my 50th daily video. Journal number four, 1997.

Going back through these has taught me a few things. I want to give you four of them today.

First one. Focus.

What made that stretch of my life so prolific is that I was specializing in one thing.

Real estate agents. Every waking thought pointed at that one market.

I started by applying everything I was learning to my own business... then packaging it so other people could use it too.

I've been genuinely shocked at how much of what I still use today had its genesis thirty years ago.

Second. Compounding.

It started with a guide to Halton Hills for my own business.

That turned into licensing the system to 40 agents in 40 different areas around Toronto.

That led to Joe Stumpf, and the two of us taking the whole thing to North America.

None of that was luck. It compounded because I was building it with the end in mind.

That's Michael Gerber's idea from the E-Myth. Think about your business as a machine you're going to duplicate 5,000 times.

Build it that way from the start and everything you make stacks on top of everything you already made.

Third. Time moves at the speed of reality.

Your mind can see the whole finished thing in an instant. There are no rails on it.

But the building of it still happens in real time, one day at a time.

That gap is where most ideas quietly die.

Fourth, and this is the one I'd underline.

Nothing is happening in your journal.

No idea comes to life sitting on the page. It has to make it out into the real world.

Woody Allen made a movie a year for 45 years.

He writes his ideas on a yellow pad and puts them in a drawer. An actual drawer.

When it's time to make one, he opens it up, spreads them all out, picks one, and puts the rest away.

Tarantino set out to make 10 movies. He's made nine. He's 100% immersed in one until it's finished.

And Dan Sullivan. When he was 70 we were walking around London, talking about writing a short book in a short space of time.

We shook hands on it. Two weeks later we both turned up at Strategic Coach with a finished book.

I built the whole 90-Minute Book process around that.

Dan's written one book a quarter ever since. Twelve years of it. He's somewhere around book 48 now.

One idea. Write it. On to the next.

That's the law of compounding with a face on it.

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 this Friday at 1pm. 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 your journal and find one idea that's been sitting there waiting. Just one.

Pick the smallest piece of it you could put into the real world this week... and go do that piece.

Show notes: https://deanjackson.com/podcasts/tol/065-how-to-stop-your-best-ideas-from-dying-in-your-notebooks/

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

Structure Doesn't Slow You Down. It Lets You Fly. Aug 06, 2026

Show notes

Good morning.

This one's a doozy.

A double spread in the journal, early 1997, Rancho Santa Fe.

The late Jerry Ballinger was walking a room through something he called the Ferrari Mind Tuneup.

And looking at it now, thirty years on, I can see what it actually is.

It isn't about going fast.

It's about laying a foundation so you can go fast in exactly the direction you want to go.

Big difference.

I turned 60 in May, and this whole year has been me going back through these journals... and finding out I've quietly been running Jerry's process on myself the entire time without calling it that.

Quick side note before the steps.

I was doing a lot of mind mapping back then. Mind maps are out, for me.

Too convoluted for the way I think. I think logically and sequentially, one thing leading to the next.

I suspect there are two kinds of people. Mind map people, and process people.

I'm a process person. So here's the process.

First step is fuel.

Not gas in the tank. What you're taking in.

What you know. What you're reading, who you're listening to, what you're naturally curious about and can't help chasing.

Those are all clues. They point at the direction that's actually right for you.

This is the collect part of collect, combine, create. The raw material for your thinking.

Nothing good comes out if nothing good goes in.

Second step Jerry called the 24-hour franchise prototype.

Getting your day right.

And here's the part that got me. I read what I'd written in 1997 and it's still my favorite version of a day.

Bed at 11. Up at 7. Out the door at 8. Here with you at 9. Ten to twelve in my journal hatching evil schemes. Afternoons working and sharing with people. Evenings doing whatever I want.

Thirty years later. Same day.

Whatever you end up doing with your time... what's the shape of it going to be?

Third step. Stabilize, systemize, standardize, optimize.

In that order. And the first one is the one everybody skips.

Deming said you can only observe and make predictable change in a stable system.

So if your days are random and fractal, and you couldn't describe one if somebody asked... there's nothing to improve. There's no baseline to improve from.

That's honestly been my whole year. Stabilizing.

Now here's where it gets fun.

Ned Hallowell, the most-cited psychiatrist on ADHD, talks about the Ferrari mind too.

He said to me one time that the ideal is to think of your day like a bobsled run. You get in at the top, you slide through, and the rails keep you on course.

The opposite of that, the natural tendency, he calls going through your day like a toddler at a picnic.

You can picture that one. Wandering about. Oh look, a butterfly.

I've reached a compromise between the two.

I treat my days like a slalom race.

Total freedom to go wherever you want in between... but you've got to hit the gates.

10:00, phone in the lock box. 11:00, lights out. 8:00, out the door. 10:00, pencils up in the journal. 12:30, lunch and the video goes up. 1:00, appointments start. 6:30, what we've come to call Meat 30, dinner right on time.

That's the great slalom run of the day.

And the more runs you do, the better you get at going fast between the gates.

The gates don't slow you down. They're the reason you can go that fast.

Fourth step. Your unique ability.

That's Dan's framing. Look at everything you do in a week and sort it into layers.

Unique ability is the top one. The things that energize you, that you're best at, that you have unending attention for.

Below that, things you're excellent at. Then competent. Then incompetent.

Tom Peters got at the same idea with his joy scale.

What can you take off the list? What do you want more of?

Fifth step. What service do you want to render?

Everything up to here has been about you. This one's about the outlet.

Given all of it... what result do you help somebody get faster, better, or less expensively by working with you?

For me it simplified right down. We help people build prospect vending machines. Get leads, convert leads.

Thirty years ago that was valuable. It'll be valuable thirty years from now.

People are always going to need new ways to get new clients.

That's a good direction to point a tuned-up mind.

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 this Friday at 1pm. 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.

Pick one gate. Just one. The one that would make tomorrow work better than today did.

Put it in the calendar and go hit it.

Show notes: https://deanjackson.com/podcasts/tol/064-structure-doesnt-slow-you-down-it-lets-you-fly/

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

How to Write Copy That Leads People to "Yes" Aug 05, 2026

Show notes

Good morning.

Another reading from the good book today. Cash Copy, by Jeffrey Lant.

We started a Lead Conversion workshop yesterday, and somebody on it said something that sent me straight back to journal number four.

Almost everything you need to know about marketing and writing great copy fits into four words.

You get benefit now.

That's the test. That's the whole thing.

Eben and I used to call each other up just to quote Jeffrey at each other.

And the one I keep coming back to is his egregious error number twelve.

You don't know what you want the prospect to do, and you're not prepared for the prospect when he takes action.

Read that again, because underneath it that's a statement about leadership.

Your job is to lead people into action. In the direction you already know is the best thing for them.

Not to convince anybody. Not to get somebody to do something against their will.

Just to say, clearly, I understand exactly what your problem is... maybe better than you've said it yourself... and here's the next best step for you right now.

Now here's a page I wish I could put a number on.

Page 172 of journal number four, 1997. The first time these words were ever written down anywhere.

We'd made a little information booklet called How to Sell Your House for Top Dollar Fast. You get benefit now, right there in the title.

And the copy offering it went like this.

If you're going to sell your house in the next 6 to 12 months, what you do right now could make a difference of thousands of dollars. Especially if you're buying another home.

I have no idea how many millions of dollars have been made from that one paragraph.

But look at who it's talking to.

Every other agent's ad was talking to the people who are in the market today. Now's the time to sell. List your house with me. Call Dean and start packing.

Mine was talking to somebody 6 to 12 months out. Which, by the way, includes a good chunk of the people who are about to move right now anyway.

Here's the part that made me laugh this week.

Arash in Toronto has been running this as a Facebook ad. It's his primary thing at the moment.

He followed up with a woman who'd downloaded the book, recorded the call, and sent it to me.

Hi, it's Arash. I sent you the How to Sell Your House for Top Dollar Fast book. I was just curious... what was it about the ad that caught your attention?

She paused for about a second.

Well, I'm going to sell my house in the next year. And I saw that there were some things I should be doing now, and I wondered what they were.

That's the ad. She just said the ad back to him.

And it turned out her daughter was moving to town, they were selling, and the two of them were both going to buy in the same area.

None of that happens with flashy language. Or manipulative language.

It happens with leadership language. Real language.

Taking somebody by the hand and letting them know you know exactly where they're going, and you can get them there.

Jeffrey puts it better than I can.

The aim of this book is to teach you how to write masterful copy, to select the right words and to use them properly, so that your prospects spend more of their money on what you are selling than they do on what other people are selling.

But you will only achieve this desirable result if you act like a leader, not an obsequious cringer.

An obsequious cringer. Thirty years on, that still gets me.

And if you want the full picture of this, it isn't one book. It's three.

Cash Copy, for the words.

Jerry Spence, How to Argue and Win Every Time.

And Cialdini's six weapons of influence, for what's actually moving somebody underneath the decision.

Put those three together and you understand how people move through a decision... and how to guide them to one that includes you.

Being able to write words that get somebody to take action, remotely, on your behalf. That is a skill worth having.

Thousands of real estate agents have used this exact system to get listings in their own market.

And notice where it starts. Not with we're ready to sell right now.

Some of the best business you'll ever get comes from reaching people early, while they're still preparing to do the thing.

What you read about you think about. And what you think about comes about.

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 this Friday at 1pm. 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 what your best prospect is thinking about 6 to 12 months before they ever need you.

Then write the sentence that meets them there.

Show notes: https://deanjackson.com/podcasts/tol/063-how-to-write-copy-that-leads-people-to-yes/

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