Thinking Out Loud with Dean Jackson

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**Thinking Out Loud with Dean Jackson**

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

Latest Episodes:

How to have a business that works without you Oct 23, 2026

Show notes

Good morning.

We've got a lovely double spread today in journal number eight. From 1997.

And I think way back in video number one or two, I mentioned the book that was the turning point for me.

Michael Gerber's The E-Myth.

That's where I learned the concept of working ON your business, not IN it.

The subtitle is something like... why most small businesses don't work and what to do about it.

When I first read it, back in '89, I was an individual realtor in Georgetown, just outside Toronto.

Making a hundred cold calls a day. Doing all of the work myself.

And I was already bumping into the ceiling.

Because I couldn't be two places at once.

I couldn't do the cold calling to drum up the business AND be available to actually do the business.

Gerber calls it the ceiling of complexity.

So the mindset he installed in me was this... separate your business from yourself.

And it sounds odd the first time you hear it.

But here's the thing. There are 32 million businesses in the US, and the overwhelming majority are one person doing all the work.

Which is very limiting.

Now, AI is a great advancement here. It can take a lot off your plate. That may be the first place you start.

But I still remember reading that book. Sitting by the fireplace at the Delta Hotel in Mississauga.

One of those moments where something lands on a deep level.

I started thinking about my business as its own thing.

Instead of a hamster wheel.

Because the cold calling worked while I was doing it. Step away, and nothing's working anymore.

So I asked... what could work WITHOUT me?

I'd just discovered direct response at the same time.

And I saw it. If I took the time to create a postcard that got people to call me, instead of me making the cold calls... that was leverage.

How could I use some of my money to work for me?

That led to the Guide to Halton Hills, which is still the foundation of everything today. The Home Buyer Workshop. The Six Steps to Home Ownership book.

IP assets. Intellectual property assets. I didn't know to call them that yet.

All of them from one goal. Setting up things that can work without me.

So here in journal number eight I've got a little summary of what I learned from Michael.

Most small businesses don't work. The people who own them do.

That was exactly where I was in 1990.

And your problems in your business are not the people. Unless you're the only one. Then it IS you.

Your business is a perfect reflection of you.

Because if the things that make it run depend on you doing them, you'll reach a point where you're not as energetic or reliable as you'd like to be.

An entrepreneur is a visionary.

And that's the biggest key. Create the vision of what you want.

What does it look like?

I loved the idea of assets. Ads, postcards, recorded messages.

I had phone lines down in the basement. And I'd hear them clicking and whirring in the background while we watched a movie we rented from Blockbuster.

No on demand back then.

So I'm sitting there, and I can hear my system working. People calling, listening, leaving messages for me.

The first time you see your business working without you... that's a core memory.

So two words Michael gave me. Intention and attention.

Your job as the visionary is to set your intention. See what you want.

It starts with an image. How could this work without me?

Operate on the FUNCTIONS of the business. Not the tasks you have to fulfill in it.

And there are three key processes.

First, innovation. What you do. The core thing. You run ads, send postcards, use recorded messages, VSLs.

Second, quantification. How it works. Measuring, so you know predictably what to expect.

I've mentioned Deming before. Without that measuring, you don't know whether something's actually working.

Third, orchestration. Setting up the systems. The elimination of choice at the operating level.

This is how we do it here. This is how we recruit and train to do it here. This is how we manage it, and how we change it here.

You're constantly working on the business. Not in it.

So people always ask... how do you set up a business that runs without you?

This is the beginning. It's simple.

And it's a life pursuit. I'm still working on this same model 35 years later.

It's the first place I look when I work with entrepreneurs now.

So here's my wish for you.

That you get that first time where something wonderful happens in a way that happened without you.

Magic.

Show notes: https://deanjackson.com/podcasts/tol/142-how-to-have-a-business-that-works-without-you/

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

My business-getting checklist that works right away Oct 22, 2026

Show notes

Good morning.

We're back in journal number eight. Fall of 1997.

And this page stopped me, because I was working out something I now call the optimal build order.

The order you do things in when you want to grow. Fast.

Say you set a big goal. 10x.

Most people want to rush straight into the growth.

All the new things. All at once.

But here's what I wrote first.

Streamline and optimize your systems.

Be ruthless. Cut the counterproductive stuff. Eliminate your personal involvement in any step that doesn't actually need you.

Because time moves at the speed of reality.

And the reality is you still only get 16 waking hours in a day. No matter how big the aspiration.

That's the only allocation you have.

So making time an investable asset... that's a competitive advantage right there.

That's job one.

Next. Pick one target market. The most profitable one.

I do a lot of work with realtors, and they always feel like they have to work their way up to the luxury homes.

And I tell them... why not just start there?

Oceanfront. Lakefront. Whatever the highest yield is.

Do the one thing you do better than anybody, and point it at the most valuable people you can help.

One at a time. Rules and boundaries around it.

Then. Situational marketing.

What we now call multipliers.

Get more business from the business you're already doing.

You're already working with people right now. So look around. Neighbors, friends, referrals, more for the people already in front of you.

Turn one piece of business into several. It's fast acting because the relationships already exist.

Then. Reclaim your past clients.

People do business with someone and then... it's over.

And that's one of the biggest opportunities you've got.

Think of your After Unit as equity. The people who already know you, like you and trust you.

We're not pouring new people into a leaky bucket. We shore it up first.

So start an after sales service program. Nurture lifetime relationships before you get too busy chasing new.

Then. Automated technology to sift and sort your prospects.

This part is funny to read in 1997.

Back then it was recorded messages. A CRM. Email. State of the art.

Now it's CRMs, automated emails, video, texting, AI.

Same idea. Much bigger lever.

And last. Direct response advertising for new prospects.

Now you point it at the new audience you picked.

Find them. Get in front of them. Compel them to raise a hand. Educate and motivate them. Make an offer where there's no better option than you.

That was the whole order.

And here's what got me. It's all equally true today.

Streamline first. Grow last.

You can't go wrong with that checklist.

Show notes: https://deanjackson.com/podcasts/tol/141-my-business-getting-checklist-that-works-right-away/

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

The 5 most valuable letters you can write Oct 21, 2026

Show notes

Good morning. We're being driven to Celebration in the Tesla to finish day three of the Breakthrough Blueprint. So we've got some time to talk.

Let me ask you something.

When was the last time you got a letter?

A real letter. In the mail. Meant for you.

It's probably been a long time.

I keep getting pointed back toward this. Direct mail. The stuff we did before there was an internet.

And then yesterday at the event, one of our stories came to life.

A gentleman I've been working with has a very high end client. The kind he can save fifty, seventy, a hundred thousand a month.

He'd been chasing one company for five years. Emails. Cold calls. Outreach.

Five years.

So a couple months ago we sent a letter. Written a very specific way.

And they called him.

Here's the part I love. He didn't even put his contact info in the letter. So they looked him up. Filled out the contact form on his website. To chase him.

That's how compelling it was. They saw it, they wanted it, they came looking.

I've done the same thing with estate attorneys. With estate planning.

Getting through to almost anyone with a physical thing they can hold in their hands is a differentiator. Especially if everyone else is only doing digital.

So I tell you all that because it's been on my mind.

And then this morning I flip to a page in the journal.

The heading reads... the most important letters you can write.

I was talking about realtors. But these transfer to any business.

The first one. Reconnect with your client base.

Just a nice note. I've been thinking about you.

Joe Polish and I have been talking about this on I Love Marketing. Handwritten notes.

There's something different about getting something you can hold.

Even if it's just... this reminded me of you.

For a realtor... I drove by your old house the other day. Remembered how much fun we had working together.

Human to human. Because so much of what we do is just the relationships.

The second one. Evidence of success.

You tell a story about someone you helped. A unique situation. A problem they overcame.

Say a business owner who couldn't get a conventional mortgage, because of how their income is set up. And you found a lender who does bank statement loans.

Or a couple with a third child on the way. You sold their townhouse and got them into a bigger home before the baby came.

You presence the types of people you help. And then you offer to help anyone they know in that same spot.

That's what the world's most interesting postcard does every month. A note on the back that presences who you work with.

The third one. A letter to new sellers.

Because after someone lists with you, there's this quiet stretch. Things happening behind the scenes.

So you write... everything's all set. Here are three ways you can help me sell your house for top dollar.

We've set up your instant open house. Here are flyers for work. Lead gen cards with a picture of your house.

And remember when we talked about listing? That once you list, suddenly everyone's talking about moving.

The reticular activator. In case you hear it, here are the cards.

We do these digital now. A little info flyer people can text to anybody they catch in a conversation.

Get them involved in the process.

The fourth one. Buyer testimonial letters into an apartment complex.

This was one of my favorites.

When somebody moves from an apartment into their first home, that's momentous.

Most people have no idea they could own a home for about what they're paying in rent.

So you write a letter back into the complex. In the buyer's voice.

We used to live in the River Lake apartments. It was fine when the twins were small. But we wanted them to have a yard.

We thought it was too expensive. Then our realtor told us about a program where we bought with zero down.

That'd be the USDA program here in Winter Haven. A great way to buy with nothing down.

And you include a picture. The boys playing in the yard.

As inspiration. And you offer a book on getting a lovely home for zero down.

Think about where that person came from. Would they go back and pull others out of the same spot?

Now, some of these take a little work. It's not a blanket postcard into an area.

But you can work from a template.

So here's my encouragement.

Think about the most important letters you could send.

And ask how you could put something physical back into how you talk to people.

It can be as simple as a note card.

Try one. And let me know what you come up with. I'd love to see.

Show notes: https://deanjackson.com/podcasts/tol/140-the-5-most-valuable-letters-you-can-write/

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

Why do you make your life complicated? Oct 20, 2026

Show notes

Good morning. Much, much sunnier today here in Celebration, Florida.

I've got the journal with me again. We're in November of 1997.

And I love that in this phase, I was using questions as journal prompts.

Yesterday's was... how can I set up my life to be prolific?

Today's is a different one.

Why do you make your life complicated?

And reading that now, 30 years later, from my view here in 2026... it hits different.

Because even back then, I already had this pull toward ideas that were multi step.

I could see how things fit together. I could see them at scale.

But I was starting to notice I didn't have the capability to carry them all the way to their potential.

And I had this real hunger for new. I loved to see how something could be.

For years I treated that like a shortcoming.

Why can't I be more focused on execution? Why can't I see things through?

Here's what I eventually saw.

Once I solved the puzzle, the thing lost its novelty for me.

And novelty is the word. I know now that's the ADHD. That's what drives me.

So instead of fighting it, I've come to treat it as a superpower.

Think about a construction project.

I'm the architect. I love the vision. I love the conceptual drawings, all the way to the renderings of what this could look like finished.

But the line item blueprints? Wielding the hammer? Seeing it built?

That's a different skill set. And it's not mine.

We all have our own skill set.

Mine, I've learned, is figuring out what I call the scale ready algorithm.

I crack the code. I see how it could all work out. I prove the thing works.

And then somebody else does the scaling.

Because there's a very different skill between making something scale ready... and actually scaling it.

Society rewards the rolled up sleeves. The discipline. The seeing something all the way through.

And I applaud that. I admire it.

It's just not me.

And here's the elegant parallel, sitting right there in fall 1997.

A hit song is a scale ready algorithm.

There's a gentleman named Max Martin. One of my heroes.

If you rank the people who've written the most number one songs in Billboard history, the list goes Paul McCartney, Max Martin, John Lennon.

And his first big modern hit? Backstreet Boys, Quit Playing Games. Fall of 1997. Same pages I'm reading.

Here's what Max does. He has a knack for writing songs that are going to be hits.

He goes in the studio with Britney, with Katy Perry, with Taylor Swift. He makes the songs.

And then those artists spend the next two years scaling them. Touring. Playing them every night. Doing all the work it takes to break a record.

Meanwhile Max is already back in the studio with the next person. Making the next songs.

Taylor's last album? He did all 12 songs with her.

And for the first time in Billboard history, an album launched and took the top 12 spots at once.

That's the whole picture.

So my answer to the question... why do I complicate my life?

Just simplify. Focus on the one thing only I can do. Build a support system around everything I find complicated.

So here's your turn.

If it feels like you're complicating things, go through it and ask why.

Why does this feel complicated?

And you might find that your gift, the thing that would simplify everything, is finally letting yourself do only the thing that only you can do.

Give yourself permission. Do just that little part.

And find the right people to pair up with for all the rest.

Show notes: https://deanjackson.com/podcasts/tol/139-why-do-you-make-your-life-complicated/

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

How to be prolific Oct 19, 2026

Show notes

Good morning. Coming to you live from Celebration, Florida.

Look at that sun. Breaking through an otherwise overcast day.

I'm here to start one of my three day Breakthrough Blueprints. So I've got a little time to talk.

And I've got my journal with me.

Page 82, journal number eight. We're in November 1997.

And I laughed, because the question I wrote on that page was... how can I set up my life to be prolific?

It made me smile. Because that's really the game.

If you're a creative. If you're an entrepreneur. If you're playing anything that asks you to turn ideas into reality.

Part of it is just getting yourself to do the things that take something from an idea in your head out into the real world.

For me that path runs through my journal, and then out into the world.

And the currency you trade to turn ideas into reality is units of time.

That's it. That's what it is.

Here's what struck me, flipping through these pages.

This is the SAME issue you're going to have 30 years from now.

So much of what I was writing back then was about optimizing my days. Managing my energy. Guarding the creative flow.

Putting myself in a position to be productive.

And the more productive you are, that's what leads to being prolific.

That word choice got me. If you're going to be productive, you might as well be prolific.

It's the kind of thing that lets you make a daily video for 122 days in a row.

Because here's the simple, profound part.

You can't spend more than today's allocation of time... today.

Time moves at what I call the speed of reality. There's no way around it.

Back in November 1997, time moved at 60 minutes per hour.

And here we are, nearly 30 years later. Guess what.

Still 60 minutes per hour.

We can only do one thing at a time.

And part of being productive is that there's an output for the time you spent. Some artifact. Some thing you actually got done.

So here's what I've learned over the whole 30 years.

Find the zone approach that works for YOU.

Mine? In bed at 11. Up at 7. Mornings uninterrupted and guarded for the creative work. That's my most creative stretch.

Afternoons for people. Delegation, meetings, Zooms.

Evenings for rejuvenation. Fun. Movies.

I was at dinner last night with a gentleman here at the event. He's up at 5am every morning. That's his zone, and he's done it for years.

But the trade off? He's in bed at 9.

And here's the thing. There's no nobility in waking up early.

You don't have to wake up at 5 to be a more worthy, productive person.

Robin Sharma wrote The 5am Club. I had breakfast with him once.

And I told him I think most people would do better aiming for the Nine Hour Club.

A nine hour envelope dedicated to sleep and recovery. The on ramp into perfect sleep, and the off ramp of starting your day.

Allocate those nine hours, whenever they fall, and you're better off.

So the zone is still the primary decider of how prolific you're going to be.

Now here's what I still struggle with.

Deciding what to do inside those blocks.

I've got perfect attendance at the gates now. Lights out at 11, ninety nine percent of the time. Out the door at 8. Mornings cleared, all the way to noon.

Clear for takeoff.

But I arrive at that power block, pen in hand, notebook in hand, in what I call the evil scheming position... and sometimes I'm undecided.

Multiple things converging, all carrying equal weight.

Being the dispatcher of my own time is still a work in progress.

And part of getting better is doing only the things that only I can do.

I can design things. I learned PageMaker in 1997. But lots of people can do that.

So instead I draw what I want. A postcard. A book cover. Where everything goes.

Takes me minutes. And Glenn turns it into something amazing in hours.

That's the whole game.

Set up the zones. Decide what you're going to be prolific in. And strip out the friction by doing only the things that only you can do.

Stick with that. And one day you'll look back at a prolific life track history.

Show notes: https://deanjackson.com/podcasts/tol/138-how-to-be-prolific/

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

Where to look first for the extra profits hiding in your business Oct 18, 2026

Show notes

Good morning from the car... I'm on my way to a movie.

But first, I want to share something with you.

For the last 60 days or so, I've been running a 50 Minute Profit Finder workshop on Fridays at 1pm.

The whole idea is to find the money that's hiding in your business right now.

So today I'm sharing one segment from it.

Big idea number two... how high is high?

See, most people set goals for their business around constant and never ending improvement.

Improve things 20%. Slow and steady wins the race.

But back in 2006, I read an article that I still think about to this day.

It was in Business 2.0 magazine, and it featured a gentleman named Gamal Aziz.

Gamal had just moved over from the Bellagio to run the MGM Grand.

And the first thing he did was look at every line item. Every profit contributor to the hotel.

Restaurants. Gaming. Rooms. Entertainment. Conventions.

Each one contributing on its own to the total.

Same thing for you. You've probably got several different buy buttons that people pay you for.

And for each one, Gamal asked the same question... how high is high? What's possible here?

Night after night, he'd stand in the lobby greeting guests as they headed out to their limos and taxis.

"Where are you going tonight?"

Spago. Nobu. Cirque du Soleil.

Destinations, every one of them.

Meanwhile, nobody was complaining about the restaurants at the MGM Grand.

They had a perfectly serviceable flagship doing $4 million a year. Profitable. Nobody saw a problem.

The reasonable question would have been, how do we improve that by 20%?

But Gamal knew that with a celebrity chef and a destination restaurant, that same space could be doing $8 million.

So he took it to the board. They agreed.

They ripped out the restaurant, partnered with Michael Mina, and opened Nob Hill in the same footprint.

The first year, they did $11 million.

But here's the distinction that stuck with me.

When Gamal saw they could be doing $8 million instead of 4... he booked the difference as a LOSS.

In his mind, they were losing $4 million a year by not having a destination restaurant.

That's the thinking I want you to bring to your business.

And by the way, you don't have to scale beyond what you want. You're in control. It's your dream.

But look at the framework you're running right now and ask yourself... how high is high?

I think you'll find some pretty big opportunities hiding in there.

Show notes: https://deanjackson.com/podcasts/tol/137-where-to-look-first-for-the-extra-profits-hiding-in-your-business/

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

What to say in emails to get more clicks and replies Oct 17, 2026

Show notes

A little overcast here in Winter Haven today... but we're going to talk about something bright and sunny.

How to get more clicks and replies to the emails you send.

I've been rereading the Gary Halbert Swipe Files, Volume 1, the one that arrived the other day.

And I keep thinking about how pivotal it was, back in the mid-90s, learning from Gary how to write as if I was talking to one person.

That carried right through when we made the move to email.

Email was barely getting started in the late 90s. And I took that one person idea VERY seriously.

Remember Gary's provocation? "What would you do if you could only mail one letter, and you had to get an order or be beheaded?"

I wrote every communication as if it was the only one.

But here's the thing about email.

You get immediate feedback. And you don't have to get the whole story into one message.

I remember reading My Life in Advertising and the Robert Collier Letter Book, about the guys in the early 1900s sending letters for a penny.

And I thought, if I could send letters for a penny, I'd be rich.

Little did I know we'd get to a point where we could send thousands of emails at once... people could reply... and it doesn't cost a thing.

So I started measuring every step in the journey.

The subject line has one job. Get the email opened.

Then what?

Begin with the end in mind.

The most valuable things you can get somebody to do with an email are click a link, or reply.

That's it. Those are the two.

It's almost like a choose your own adventure... you reveal only what needs to be revealed next.

Here's how I figured that out.

In the late 90s we were filling free half-day real estate workshops in hotel ballrooms. Hundreds of people at a time.

Think of it as a live theater VSL.

The goal was a $1,000 ticket to our three-day main event, where we could introduce people to our coaching program.

The vehicle for the main event was the workshop. And one of the vehicles for the workshop was email, to a list of 50,000 realtors.

The winningest subject line we ever had? "Orlando Real Estate Marketing Workshop."

Once they opened it, the only thing I wanted was for them to go to the page where they could register.

Now I could have told the whole story in the email and tried to convince them.

But then I'd never know who was considering it.

So I asked, what's the least amount of words that gets that click?

And this is funny, because you'll see it right here in my journal... I'd imagine I was a wizard.

If I had the power to command people to do anything, what would I say?

The subject line would say, "Open this email."

The email would say, "Click here."

So what's the least I can add to that command to make somebody click?

Curiosity is a big piece of it.

"Joe Stumpf and Dean Jackson are doing a real estate marketing workshop in Orlando next month. Can you make it to this?"

The link was "Can you make it to this?"

And the details were on the other side of the click.

30 years later, that's still how I fill my events.

"Hey, I'm doing a three-day Breakthrough Blueprint in Orlando. We're going to spend three days in the boardroom applying the 8 Profit Activators to your business. Would you like to join us?"

That's it.

It gets the people who are interested or curious, but not committed, to identify themselves.

And with intelligent links, you can see exactly who clicks... so you know whether the message is working.

On the other side of that click was one of the best sales letters I've ever written.

"Would you trade three and a half hours for three extra transactions in the next 60 days?"

It was a rocket ship for us.

Because it was all engineered around one question... what do I want people to do, and what are the least words that will get them to do it?

I'm not trying to convince anybody. I'm not asking for the final decision.

I'm just advancing people one step closer.

That's the key to getting the most responses.

So try it out. Watch your inbox, because I'll be sending you emails just like that.

And it would be super if you replied.

Show notes: https://deanjackson.com/podcasts/tol/136-what-to-say-in-emails-to-get-more-clicks-and-replies/

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

How to write a subject line that gets your email read Oct 16, 2026

Show notes

Had another great breakfast this morning, reading my copy of the Gary Halbert Swipe Files, Volume 1.

So many of the things I use today, I learned from Gary.

And one of the most important ones wasn't even about email. Back in 1997, email was just getting started. Letters were the thing.

Gary was famous for this idea... people sort their mail standing over the garbage can.

Into the A pile and the B pile.

The A pile is personal. It looks important. It's just for them, and they want to read it.

The B pile is junk mail. It's headed for the trash.

Your only goal is to get into the A pile.

So Gary asked himself, "What if I could only mail one letter, and it had to get an order or I'd be beheaded?"

He threw out all the standard direct mail wisdom. Bulk mail to save money. Indicia because it's easier. Teaser copy on the envelope. Window envelopes.

He wouldn't stake his life on any of it.

Because to place an order, somebody has to read your letter. And to read it, they have to open it.

So he'd send it first class. Real stamps, maybe two or three, put on a little bit crooked so it feels like it came from one person.

No logo. No teaser copy. Just a return address in the corner and the address typed or written by hand.

That letter gets delivered... and it survives the sort.

Now fast forward to email.

We don't get a lot of mail anymore. But we get a TON of email.

And here's the thing. Even with three or four accounts, even with a burner for newsletters and lead magnets, everybody reads it all in one feed. For me that's my iPhone.

So here's the secret to getting your email opened.

That's the ONLY job of the subject line. It's the envelope for your direct mail.

Think about the emails you're most likely to open. They come from your friends. From people you know.

Your mom has a 100% open rate.

Try this. Scroll through your inbox and find the last email that was just for you, one of one, from somebody you know.

You'll see it reads completely differently from the marketing emails above and below it, the ones trying to trick or cajole or excite you into opening.

Picture your mom with a label maker, typing out the label for the file folder where you'd keep that email.

That's what I call a label maker subject line.

Overtly clear. Nothing vague, nothing tricky.

By 1998 we were using email to fill our real estate marketing events. The best subject line I ever wrote simply said, "Real Estate Marketing Workshop."

Going to Orlando? "Orlando Real Estate Marketing Workshop."

It drew in exactly the people we wanted.

My friend Ross, a great copywriter and a big Gary Halbert fan, shared a perfect example.

His aunt emailed her neighbor. The subject line said "Irish stew." The email said Ross had agreed to make an authentic Irish stew for dinner on Thursday night, and would Nancy and Bob like to join them?

It was almost as if she'd had marketing training.

Innocently perfect.

So here's your assignment.

Look at the last four or six emails that were addressed just to you, and notice the patterns.

Give people a clear, neutral frame for what your email is about, and watch what it does to your open rates.

Because if you're going to do email marketing, you've got to get the emails opened.

That's the first job.

Tomorrow... how to get them replied to.

Show notes: https://deanjackson.com/podcasts/tol/135-how-to-write-a-subject-line-that-gets-your-email-read/

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

How to write a letter that can make you rich Oct 15, 2026

Show notes

Good morning.

It's a big, big day today.

Something arrived in my mail yesterday... The Gary Halbert Swipe Files, Volume 1.

And this one is about how to write a letter that can make you rich.

As we go through 30 years of these journals, I keep seeing the same thing.

The biggest successes, the things with the biggest financial impact, all came from being able to put words together in a way that helps people.

In the late 90s, when I was writing these journals, that meant getting a message to people who were about to sell their home or buy a home.

So this is the perfect time to introduce Gary.

There's a through line that goes all the way back to Claude Hopkins, who we talked about with My Life in Advertising and Scientific Advertising.

Almost every great marketer you know branched from the Claude Hopkins school. When I started learning marketing in the early 90s, Jay Abraham, Dan Kennedy and Gary Halbert were the big three.

Whether people are doing video sales letters, email, social media or AI stuff now... it's all rooted in the ability to put words on paper.

In the 90s we had postcards, print ads and sales letters. Now there are so many more ways to reach people.

But every one of them is just a delivery device for the words.

The thing I learned from Gary that has carried through all these years is writing to one person at a time.

Gary may still have the single most mailed sales letter in the history of direct mail... for a coat of arms.

And when you read anything Gary wrote, it feels like he's only talking to you.

All the great copywriters, Gary Bencivenga, Parris Lampropoulos, John Carlton, point back to that same ability.

Gary's process was, "If I could only mail one letter..."

It forces you to write so that one person feels like you're making direct eye contact with them. You start with what they know, and you lead them, conversationally, to where they could go.

That's why we always say start where people are.

When I wrote, "If you're going to sell your house in the next six to 12 months, what you do right now can make a difference of thousands of dollars," that was the whole message.

It got the attention of exactly the person I wanted to have that conversation with.

Then you show them, and prove it. All I wanted them to do was get the book on how to sell your house for top dollar fast.

In upcoming journals you'll see things I haven't even touched on yet that have been the biggest things I've ever done.

But they're all rooted in that same idea.

Gary used to call copywriting the greatest job in the world. All he needed was a pen and a piece of paper, and he could do it from a beach... or even the moon.

Joe Polish and I always joke about it, but Gary would say any problem in the world can be solved with a good sales letter.

I think that's true. It's the skill that will make the biggest difference for you.

So where do you start?

Get familiar with the canon. My Life in Advertising and Scientific Advertising, David Ogilvy, Breakthrough Advertising. Any modern master copywriter has basically the same 10 books on their base curriculum.

Then layer on the psychology. Robert Cialdini's Influence, Gerry Spence's How to Argue and Win Every Time, Dan Ariely's Predictably Irrational.

All of it gives you a deeper understanding of the way people think... and how to present words in a way that moves them to action.

That's why I always start with a letter.

And don't get caught up thinking that means a direct mail letter.

A letter is a communication to one person.

If you can imagine one person, and write exactly to them, you lead them to the conclusion that the very best thing they could do is whatever you say to do next.

That's the magic of how to write a letter that can make you rich.

Stay tuned... we'll keep digging it up.

Show notes: https://deanjackson.com/podcasts/tol/134-how-to-write-a-letter-that-can-make-you-rich/

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How to get in the MarketMaker position Oct 14, 2026

Show notes

Good morning.

We're winging our way through journal number eight. It's 1997.

And today I saw a page about an expansion for something we were doing called unixcontracts.com.

Now I have a name for what we were doing. I call it putting yourself in the market maker position.

And it's a very advantageous place to be.

It goes all the way back to the late 80s, when I was running a painting company with my friend.

We were college kids, and we hired college kids to go door knocking in the evenings and on weekends... looking for people who wanted painting done that summer.

At the Chamber of Commerce, other entrepreneurs would hear what we were doing and say, "Man, I wish I had someone who could do that."

So I had a brainstorm.

We've already got people out knocking on doors. What if we looked for anyone doing a home improvement project this summer?

So they went out with a clipboard and a checklist. Painting, of course. But also a new roof, windows, siding, a deck, a pool, a fence, landscaping, the driveway.

And we set up relationships with the other businesses, who paid us a referral fee.

Our lead generation turned into a very nice profit center.

That has stuck with me. It's valuable to be the person who identifies people who are going to do something... and directs that business to someone else.

That's the essence of being a market maker.

I did the same thing in real estate with a guide called Toronto and Beyond... the 40 great places to live within an hour of Toronto.

I licensed my system to a realtor in each of those communities, ran ads for the big guide, and referred the leads out.

Then the Unix contracts.

We were working with a company that placed contract programmers with big companies like Nortel.

The programmers could make a lot more money contracting. But they worried there was no job security, so they were reluctant.

So we ran an ad in the tech journals... "Unix contractors commanding $55 per hour."

Now we had a pool of programmers interested in contracting before anyone was hiring.

You've heard the phrase "dig your well before you're thirsty." We stocked our pond.

Same thing with a party rental company.

Tents and tables aren't the sexiest thing a bride is anxious to decide on.

But the most valuable thing in that whole market is knowing someone is planning an outdoor wedding.

So we put together a directory of the 101 great places to have an outdoor wedding in Toronto.

Asking for it says, "I'm going to have an outdoor wedding."

And the florists, limo companies, bridal shops, caterers, DJs and bands all wanted to be in that directory too.

So here's the pattern.

If your business is a middling part of somebody's journey, go all the way up to the front.

Find the people entering the process, where it's inevitable they're going to need you along the way.

How do you catch a parade of elephants? You see where they're going, run up ahead, and dig a big hole.

Everybody else along that line is myopically focused on their own piece of the puzzle.

If you stick your head up and see the whole journey, you identify people first. You get to build the relationship, be the trusted advisor, be their advocate.

We call that being the mayor of a category.

My friend Taki Moore said something very insightful about that yesterday.

Being the mayor isn't a position of prestige. It's a position of service.

The mayor of a category is the person who is the most useful to that category.

So what's the most useful thing you could put together for someone just entering your market?

Then appoint yourself. There are no votes. Nothing's stopping you.

Be the mayor... and the byproduct is you become the market maker.

Show notes: https://deanjackson.com/podcasts/tol/133-how-to-get-in-the-marketmaker-position/

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