Thinking Out Loud with Dean Jackson

Latest Episodes:

Is this the BEST or WORST time ever to be alive? Nov 03, 2026

Show notes

Okay, I'm back. Still in Phoenix.

I was driving to the Henry this morning, and a question has been sitting with me.

It comes from the journals. I've been reading back through 1996, 97. I think 96 was the first time I ever came to Phoenix, and it was a wonderland for me.

And here's the question. Is this the best time ever to be alive, or the worst?

Best of times or worst of times.

I imagine every era asked that. But today I felt it in a very practical way.

Look at what I take for granted.

I have a Tesla with full self driving. I charge it at my house. I get in, I say navigate, I push a button.

The garage opens. It backs out. It drives through the neighborhood, out the gate, makes every turn all the way to the airport. And parks itself.

I take it for granted. Until this week.

I'm staying with a friend, and today I borrowed an extra car. A gas car.

It has a key. I had to put the key in. Push the button. Actually drive it. Pull up Apple Maps on my phone for directions.

And I thought all the way back. In 1996 we'd have used a paper map. Trying to find your way around all these Phoenix freeways. With a folded piece of paper.

So in that real, usable way... life is the best it has ever been.

I live in Winter Haven. And this week there's news that Florida is going to be the first in the country to put up passenger drones.

Along the I4 corridor. St. Petersburg all the way to Daytona. You get in a drone, fly over the traffic, get met by a self driving taxi on the other end.

Transportation has never been better.

Same with communication.

I record a video like this. I copy a link, drop it into a bot my guy Stuart runs for me, type the title, push a button.

And within 30 minutes it's up. Viewable by anybody on YouTube, anywhere on earth.

Next door or in Botswana. Doesn't matter.

That is the best of times.

But here's the other column.

Today is election day in the US. The last few weeks have been, let's say, eventful.

And I've had this conversation with Dan Sullivan.

In every practical, usable way, this is the best life has to offer. Conveniences, opportunities, connectedness, all of it.

But the worst of times is the battle for our minds.

The battle for your internal dialogue.

This little box. This phone. It's sending you news and conspiracies and darkness and emergencies and fear from every corner of the earth.

And our brains are not equipped for that.

We're not supposed to know every bad thing happening everywhere. We can't tell the difference between a real threat and a constructed one.

Your brain was built to scan the mile or two around you. And worry about the 150 people in your tribe.

That's it. That's what it's for.

It was never built to carry all the anxiety in all the world.

So that one goes in the column of... be vigilant.

Guard your mind. Guard what gets in, and how it gets processed.

My friend Jamie Smart wrote a book called Clarity. There's a little book of Clarity too.

Those ideas have helped me more than almost anything with this. How to manage all the input without letting it drive you to anxiety or fear.

And here's what makes it so vivid for me right now.

I'm reading what life was like in 1996. I'm living 2026. And I'm trying to imagine 2056.

I can't even picture it.

For 25 years we've watched everything that could be digitized become available to us.

Every song ever recorded. On any device. Whenever you want. For nine dollars a month. Free if you'll take the ads.

So where does AI go from here?

We're just at the start of the generative stuff. Things we speak into existence. AIs paired with robots.

Follow that line forward and our lives get supported in ways we can't imagine yet.

So that's the thought. Straddling 1996 and 2026.

Tell me in the comments. Best of times or worst of times. And why.

Show notes: https://deanjackson.com/podcasts/tol/152-is-this-the-best-or-worst-time-ever-to-be-alive/

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Experience Maxxing: how to design experiences your people can’t resist Nov 02, 2026

Show notes

Here we are. Scottsdale this week, for Joe Polish's Genius Network.

And the timing is perfect. Because we're still in maxxing week, and today we're on experience maxxing.

I'm at the Henry, just outside Paradise Valley. Every time I come to Phoenix, this is my first stop. My unofficial cafe headquarters.

Here's something you might not know about me. I like to grant a place a monopoly.

When I love somewhere, I just keep going back. I don't shop around.

So I sat here today, reading in journal number eight, and I found the word service.

I've since evolved that word to experience. Because that's really what this is. All of it.

And I asked myself the question. What is it about the Henry that makes me want to grant it the monopoly?

Start with the obvious one.

The outcome has to be the primary thing.

The coffee is amazing. The food is amazing. You have to get the thing you came for.

But here's the thing. That alone is not enough. The outcome by itself doesn't make you want to come back.

It's the intangibles.

The environment. The vibe. The music. Everything you touch and sense above the line.

The design, the coloring, the aesthetic. The curation of the whole place.

And look. It doesn't take a rocket scientist. We like beautiful things.

Everybody has character. But it's style that we appreciate. And style requires someone to have the eye. A vision for all of it.

So think about everything that's going to touch somebody.

If a person went through your process on visuals alone, what would it look like?

What does an experience with you sound like? What does it smell like?

We did a book once called Smells That Sell. The commercial scent market is around four billion a year.

One company here in the US does over two hundred million just on diffusers and custom scents.

Walk into a luxury hotel. There's a vibe you're appreciating without naming it. The look, the sound, the smell, the design.

And then the people.

They're trained. Outwardly focused. Making sure you're having a great experience.

And competent at the mechanical part. The outcome actually gets done.

It's the integration of all of that. That's what creates experiences people crave.

So here's the tool.

Build a client experience timeline.

How does somebody interact with you from end to end? From the very beginning to the very end.

Even if all you sell is a product.

The unboxing. The arrival. The moment they first experience the thing.

How is that experience architected to translate your vision for what they really want?

It's not enough to have an efficient process that gets the result.

And there's a little secret in all of this.

There are a few small things in design that, if you pay attention, make you look like you know what you're doing.

Little hinges that swing big doors. Typography. Alignment. The small stuff.

Every time I come here I get more inspired to pay attention to these details.

So it felt fitting to do an episode on experience maxxing while sitting inside one of my favorite benchmark experiences.

If you're ever in Scottsdale, the Henry. It's topnotch.

Go find the place you'd grant a monopoly to. Then figure out why.

Show notes: https://deanjackson.com/podcasts/tol/151-experience-maxxing-how-to-design-experiences-your-people-cant-resist/

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Mailbox blunders that would make Gary Halbert cringe Nov 01, 2026

Show notes

Good morning. A little overcast out here.

Sunday I was at breakfast reading through my Gary Halbert swipe file, volume one.

Bond, Gary's son, is putting together an event where those of us who knew Gary and were mentored by him share some stories.

And the timing was perfect. Because this week my mailbox handed me a couple of things that, if Gary were alive, would have broken his heart.

So many things he figured out, people now try to smuggle into their direct mail. And they do it badly.

Here's what Gary knew.

You speak to one person.

There's a thought exercise. If you could only mail one letter, and you had to get a response, what would you do?

That question is what led Gary to make his mailings look like a one of one. A letter for that person and nobody else.

Handwritten address on the envelope. A real stamp. Nothing on the return except the address itself.

Because the whole game is getting it delivered and getting it opened. That's the most important piece.

So let me show you what landed on my doorstep.

The first one is trying to do exactly this. And it's addressed to current resident, 115 Woden Way.

And you can tell instantly it's a handwritten font. Not even handwriting. A font pretending to be handwriting.

Honestly? You'd be better off in plain courier. Or just a discrete printed label.

We did a big nine by twelve mailing this spring, law firm to law firm. Some envelopes we hand addressed. Others we just slapped a clean printed label with the firm's logo and return address.

And I learned something. In that case, looking like it's just for them beat smuggling in fake handwriting that wasn't even needed.

Back to this one. PO box return address. A pre-sorted stamp.

Every one of those little signals screams this was not written just for you.

So what's the message? Dear neighbor. I hope this letter finds you well.

My reason for writing is to share a scripture. Then a little tract. Please visit the website.

Jw.org. So. Jehovah's Witnesses. Be well, Judy. No last name. Just Judy, my neighbor, mailed from St. Petersburg.

They wanted me to believe it was the only one mailed that day. They failed.

Here's the second one.

Came in a birthday card size. I love that size, by the way. Something very personal about it.

But again. Nobody alive believes that handwritten font.

Not a single person. If you're going to do the handwriting, do the handwriting. Actually do it.

Pre-sorted bulk stamp again. Nobody's buying it.

Inside, it's made to look like a torn-off legal pad. Like someone just scribbled you a note.

And the font itself isn't bad. But here's the thing.

Remember Jerry Spence, from How to Argue and Win Every Time? He says our brains come equipped with psychic tentacles.

We're always reaching out, testing things for realness. And we can detect what he calls the thin clank of the counterfeit.

You catch it here. The ink is a little faded. You can tell it wasn't pressed straight onto the page.

Hello neighbor. Nothing says personal like hello neighbor.

Now's the time to update your windows and doors. Our team is in your area. Buy one, get one 40% off.

And they double-printed over the text to fake a bold handwritten stroke.

The offer ends October 31st. It ended yesterday. I picked this up today. It's already too late.

Thanks, Clyde. There's his number. Expired.

So here's the most valuable thing you can take from all of this.

The reason direct mail works, and the reason I love it, is for visible prospects.

When you know exactly who you're trying to reach. Make it like it's just for them.

And here's the amazing thing Gary pulled off.

In the 70s, there were basically no computers. Personalizing anything was next to impossible.

But he figured out the coat of arms.

He could mail what looked like a personal letter to every McDonald in an area, and have it feel like it was written to one.

It was from his wife Nancy at the time. Dear Mr. McDonald, did you know your family name was recorded with a coat of arms in ancient heraldic archives more than seven centuries ago?

My husband and I discovered this while doing research for friends with your same last name.

We've had an artist recreate it. Printed it into an attractive one page report.

If you'd like one, send back the envelope with two dollars, and we'll mail it to you.

That letter may still be the single most mailed letter in the history of direct mail.

So many lessons sitting in that swipe file.

Think about what direct mail actually is. You're hiring a uniformed government employee to carry your message right to any doorstep in the world.

For less than a dollar. A forever stamp is what, 78 cents now.

It's worth it to figure this out.

Figure out what you'd say to one person if you could mail one letter.

Then work out how to do that at scale.

Show notes: https://deanjackson.com/podcasts/tol/150-mailbox-blunders-that-would-make-gary-halbert-cringe/

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Offer Maxxing: More certainty = More money. Period. Oct 31, 2026

Show notes

Back outside. Happy Saturday.

We're still in maxxing week, and now we're on the most exciting part of all of it.

Offer maxxing.

Because here's the thing. The best way to improve the whole machine... lead generating, lead converting, all of it... is to have a better offer.

The better your offer, the better the outcomes.

To get people to take action, you have to transfer certainty. Certainty that they'll get the result you're promising.

And the best way to guarantee certainty of outcome is to guarantee certainty of outcome.

So here's the thought exercise I give people.

What would I do if I only got paid when they got the result?

You don't have to commit to it. Just think the thought.

Because thinking it changes how you look at everything you offer.

Begin with the end in mind. What would it take to get somebody the ultimate outcome?

Let me tell you about the diabetes guys.

Health and fitness guys. They had a protocol for reversing type 2 diabetes, caught early.

And they were trying to figure out how to sell more $27 ebooks on it.

I was fascinated. You can actually reverse it. Six months, apparently, if you do the things.

But the ebook just lists the protocol. And the problem is people don't do what they could do.

Compliance. That's the whole game.

So I said, let's play. What if I gave you ten people with diabetes and six months.

And if any of them still have diabetes at the end... you get beheaded.

Now what would you do?

They need to change their diet. But humans have free will and taste buds and an addiction to sugar.

So you don't hand them a list. You prepare the meals and deliver them. No thinking required.

They need to move. So a personal trainer shows up and walks them through it.

The testing, the supplementing, all of it. Everything you'd do if your life depended on the outcome.

That's the starting point.

See what happens here.

So many times we meter out a fire hydrant of value through a garden hose.

We choke the result because we're worried about the price.

Flip it. Start with the outcome. Figure out the ultimate way to guarantee it.

Then work out what it costs to deliver.

And now you've got certainty yourself. You know you can do it.

You start spotting why people fail, so you filter those out up front.

You turn the tables. Now you're the buyer. You select who you take on.

And almost always, this is the path to raising your prices.

Not for ego. Not just because you want more money.

Because you're actually delivering the result people want. It's a well earned increase.

The $27 ebook sells a protocol.

But the right person, facing a lifetime of insulin and a shortened life, might pay $27,000 for a certain reversal.

Same thing, different space. There's a watchmaker called Richard Mille.

Their watches average $185,000.

And they started with one premise. Build the very best watch possible. Then look at what it needs to cost.

When you think at the highest end of certainty, the price follows.

They found themselves alone at that number.

Plenty of luxury watches at thirty, fifty, seventy thousand. And museum pieces at a million.

But this was a practical watch. And the market for it was much bigger than they expected.

If you've got a $20 million yacht, of course you'll wear an $185,000 watch on it.

If you've got a garage full of supercars, of course you'll wear one on your wrist.

Start with the best thing you're capable of. Then price your offers from there.

Because here's the line to sit with.

There's a bigger audience for outcomes than there is for paths to outcomes.

Show notes: https://deanjackson.com/podcasts/tol/149-offer-maxxing-more-certainty-more-money-period/

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Conversion Maxxing: Find NOW buyers. Oct 30, 2026

Show notes

Welcome back. Let's keep going on lead conversion maxxing.

I was sitting with this today, flipping through what I wrote back in 1997, and I noticed something.

On page 168 of journal number eight, there's a seed of an idea I'm still running on today.

It's this. People take different amounts of time. And that's okay.

Here's what I've come to see since.

There are really only two timeframes in lead conversion.

Now. Or not now.

And the only time we can ever actually help somebody is now.

Sit with that for a second. Everything we're doing is just trying to find out if it's now.

Yesterday we talked about the 3%. The five star prospects who are ready right now.

Here's the part people get backwards.

We are not turning anybody into a five star prospect.

We're not convincing them. We're not creating them.

We are discovering them.

Nothing you do makes someone ready. Everything you do just reveals who already is.

So if they're not ready now, fine. We keep educating and motivating. We stay in the picture.

But the real question is... what's the next step for them?

I call it the lead domino. Think like a chess master.

What's the one small move that leads to the next thing?

Take real estate. Someone's going to sell in the next 6 to 24 months.

Don't ask them to sell. Ask what they'd naturally want next.

And people selling a house usually want one of three things.

Some just want the price. What's it worth. Because every other number depends on that one.

Some are frozen on the work. The repairs, the carpets, the junk. They can't picture putting it on the market yet.

And some would move fast if the right offer showed up, even though they're not listed.

None of that came from guessing. It came from sitting in thought and playing out what the prospect wants next.

Now here's the move.

Instead of if there's anything we can do, just call us... which nobody reacts to...

we bake cookies.

We wrap each of those three desires in something that feels made just for them, where we're not imposing.

And we use magic words. Whenever you're ready.

I'm not putting my timeline on them. Neither should you.

So. Whenever you're ready, here are three ways we can help.

There's a pinpoint price analysis. Exactly what your home would sell for against everything on the market.

Name it, by the way. When you name something, it sounds like it already exists.

There's a room by room review, with a checklist from the curb to the closet, showing what's worth doing and what isn't.

And there's the silent market. We may be able to sell your house in 24 hours without ever listing it.

Three cookies. Each one helps them without them having to impose on me.

But here's the engineering underneath it.

As an agent, what I really want is to be in what I call the listing position.

In the kitchen, with someone thinking about selling.

All three cookies are designed to get me exactly there.

Pinpoint price? Let me pop by, I'll bring the comps.

Room by room? Let me pop by, show me through, I'll bring the checklist.

Silent market? Let me pop by, we may have the perfect buyer.

Every path lands me in the listing position. But that's never what I led with.

I didn't say invite me over. I said would you like a cookie.

Same thing with the outdoor lighting company.

We ran a catalog. People respond. Then the next cookie... want to see your house lit up?

We take a daytime photo, run the software, show them the glow.

Then we offer to put the lights up as a demo. No cost. No obligation.

And when they see their own house lit up at night... that's all it takes.

So here's your work.

What's the natural next step for someone in your world?

Not buy my stuff. Not sign this.

Just the move that gets you into position for the next thing to happen.

Figure out what your listing position is.

Then bake the cookie that walks them to the door.

Show notes: https://deanjackson.com/podcasts/tol/148-conversion-maxxing-find-now-buyers/

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Lead Conversion Maxxing: Start here. Oct 29, 2026

Show notes

Okay, let's keep going with maxxing week.

I've been traveling and I kind of lost track. I think it's Thursday night.

Today it's lead conversion maxxing.

And before we touch any tactics, we have to fix the thing that runs underneath all of it.

What you believe about your leads.

Because if you did the lead maxxing right, you got them early. You got them exclusively.

You steered them off to your own tributary and now you're the single voice educating them.

So here's the first mistake I see everywhere.

People think the only good leads are the ones ready to buy right now.

And they miss almost everything.

Someone who raises their hand is about five times more likely to do something more than 90 days out than inside the first 90.

Now I'm not saying sacrifice the first 90 days. Or the first nine.

If somebody wants to go right now, wonderful. That's the whole point.

But whatever you do in that first hundred days, you'll do three to five times more over the next hundred weeks.

That sounds like blasphemy to a CMO who only looks at ROAS in the first 30 days.

What's the earnings per click. Did we convert before the credit card bill came due.

That's an expense mindset.

Take a capital investment approach instead.

The best thing you can do is find all the leads sooner than anyone else, get them in relationship with you, and get them exclusively.

So when it's time, you're the first thought they have.

Here's a number that settles it.

Just over 50% of the people who inquire about anything will do that thing within the next hundred weeks.

So objectively, the people inquiring are going to do something.

It's not about the quality of the lead.

It's whether they do it with you.

Which brings me to the whole language around lead conversion.

Are they scrubbed. Are they qualified. Run them through the gauntlet.

As if the leads are dirty and guilty until proven innocent.

Flip it.

Treat every single one like a five star prospect until they prove they aren't.

Not the other way around.

A five star prospect is willing to engage, friendly and cooperative, knows what they want, knows when they want it, and would like your help.

All five have to be true.

Not everyone is willing to engage right now. That doesn't make them a bad prospect.

So in the first hundred hours, you're hunting for the ones ready to go.

And if they're not ready, that's fine.

They move into follow up, where you keep adding value and educating until they are.

But here's the other big mistake.

Sitting back and hoping they call.

Even the language gives it away. If there's anything I can do, feel free to reach out.

That's passive. That's handing your leadership role back to them.

You're saying, you request something first, so I can react without risking rejection.

Let me give you the kitchen analogy.

Say I bring you into my house and sit you in the living room.

And I say, help yourself, there's lots in the fridge.

You're not going to go rummage through my fridge. Not a chance.

But if I walk out of the kitchen with a plate of fresh cookies and say, would you like one...

It's harder to say no than to just take one.

You take the cookie.

Because I anticipated what you'd want and brought it to you. Now you're not imposing.

Think about how we work.

If I ask, would you like a cup of tea, you might say, only if you're having one, don't boil the kettle for me.

We don't want people going out of their way.

You'd never say, you know what, bake me some cookies. It's not going to happen.

But we love when things are offered.

It's hospitality.

So figure out what the cookies are for your five star prospects.

What can you anticipate they want, and how do you wrap it so it feels like a gift, not an imposition.

There's so much here we're going to need two parts. We're only in the first hundred hours.

So for tonight, just change the one belief.

Five star until proven otherwise.

Show notes: https://deanjackson.com/podcasts/tol/147-lead-conversion-maxxing-start-here/

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Gamifying consistency: My best advice from Jerry Seinfeld Oct 28, 2026

Show notes

Good evening.

Not good morning.

Listen, if you want to see confused looks on people's faces, pull up to a gas station at 10:30 at night in your Tesla and park right at the pump.

Because there's light here. And I need light to record this for you.

Here's what I want to talk about. It's going to be short.

Today marks 130 days in a row of posting a video.

And there's a piece of advice from Jerry Seinfeld that was particularly on my mind today.

He's been doing his thing for 50 years.

And once he realized that comedy was really about writing. About crafting his thoughts into words he could perform.

He committed to writing every day.

And here's the advice.

Set aside the time. Do it every day. And every day that you do it, mark an X on the calendar.

Don't break the chain.

That's exactly the mindset I've been running for 130 days straight.

And here's the funny part.

Nobody's going to fine me if I skip a day.

It's not going to cost me anything. Nobody's going to miss it.

There's no boss. No deadline. No penalty.

But I feel compelled to do it anyway.

Because I want to play the game.

Can I do this a thousand days in a row?

We're going to find out.

See, that's what happens when you gamify consistency.

When you turn the thing you're trying to do into a chain you don't want to break.

The X on the calendar becomes its own reason.

You're not doing it for the reward anymore. You're doing it to keep the streak alive.

Think about anything you've been trying to be consistent at.

Exercise. Writing. Calling your people. Whatever it is.

Most of us treat it as a decision we make fresh every single day.

And deciding fresh every day is exhausting. You lose.

But make a commitment to do it every day.

Put the X on the calendar.

And then the chain does the work.

So here we are. 10:30 at night, after a long day at an event, then a flight in from Charlotte.

And I couldn't wait to get in the car and do this.

Tomorrow morning we're back to maxxing week.

We'll talk about conversion maxxing.

But tonight, we didn't break the chain.

130 days and going.

Don't break yours.

Show notes: https://deanjackson.com/podcasts/tol/146-gamifying-consistency-my-best-advice-from-jerry-seinfeld/

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Leads Maxxing: More leads. Sooner. For Less. Oct 27, 2026

Show notes

Welcome back to maxxing week.

So far we picked the target market with the best ROI.

Today it's leads maxxing.

How to win at getting leads. Which is the most valuable part of the whole equation.

Solve this part and you've got a smooth path through everything else.

Here's where most people go astray.

They put 100% of their attention on in market leads.

The 3% who are ready to buy something right now.

And when you only chase those people, you pay a premium.

Because everybody else is competing for exactly the same 3%.

So you pay the most money and you've got the most competition. Everyone screaming the same message.

Picture the market as a river.

A meandering river making its way down to the mouth of the ocean.

The mouth is in market. That's where people are ready. New roof, new kitchen, buying a house.

And that's the most crowded part of the whole river.

All your competitors are standing there at the base, shouting over each other.

There's a much better approach.

Go upstream.

Up where people first get in the stream. There's far less competition up there.

Imagine you built your own little side tributary.

And you put an arrow and a sign that says if you're thinking about a new kitchen, go this way.

And people just... drift off down your private tributary.

Meandering down to a quiet cove where nobody else is paying attention.

Let me give you a couple of examples.

The party rental company. We talked about them before.

The highest ROI audience wasn't just anybody. It was outdoor weddings.

So we don't wait at the base of the river for someone to search party rental company near me.

That's where you pay the highest price and fight everyone.

We went upstream. We found people at the very beginning of planning an outdoor wedding.

We put together a directory. A hundred great places to have an outdoor wedding in Toronto.

And now we're in contact with someone who's going to need a party rental company in the next 12 to 18 months.

See what we did there.

We set our own needs aside.

We're not even talking about party rentals. We're talking about what they're looking for.

And what they're looking for is the venue. Where is this wedding going to be.

That has to come before they ever choose a rental company.

Same thing with anything that's a considered purchase.

We've been building a directory for assisted living facilities.

People looking for an aging parent or partner. That's not an impulse.

They're starting to recognize the signs that this is coming eventually.

So you offer them the most helpful information as they begin that journey.

And you're in conversation with them before anybody else.

Now here's the dynamic.

Most people don't want to hear about a lead that takes 6 or 12 or 18 months to mature.

They want bottom of funnel. In market. Right now.

Rory Sutherland told a story about bees that stuck with me.

Bees do the waggle dance. It tells all the other bees where the pollen is.

But about 15% of them don't follow the dance.

They're explorer bees. Their job is to go find new sources of pollen.

And without them, the hive implodes. It would exhaust the known pollen and never find the next batch.

They play an essential role.

So think about your budget the same way.

Maybe you've already optimized for in market leads. The SEO, the AdWords, the Google business stuff. Get a quote, book a strategy session, come on the webinar.

All bottom of funnel. And good at it.

Now what if you allocated 10 or 15 or 20% of your budget to what I call lead futures.

Identify people early in the process. And nurture that.

Stay best in class at the bottom of funnel. Don't switch your whole focus.

But put a slice toward finding the top of funnel, the early ones.

And over time I think the value of those early leads eclipses the now leads.

Because you were the only one they ever talked to.

That's why giving people a way to do research wins.

A catalog. A book. A directory. Something that educates them about the process.

Somewhere they'd go to gather information at the genesis thought. The very first moment they become a future prospect.

Get there first and you're often the only voice in the room.

So here's my nudge for you.

Think about the timeline. Where in the process is this person.

More leads. Sooner. For less.

And stop judging a lead by how fast they're ready to buy.

Show notes: https://deanjackson.com/podcasts/tol/145-leads-maxxing-more-leads-sooner-for-less/

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

Money Maxxing week! Oct 26, 2026

Show notes

Good morning.

Except it's not morning. It's nighttime.

I've been in the airport all day.

My whole plan was simple. Get to the airport, get to Charlotte, shoot a nice video in the afternoon, get it to you on time.

Best laid plans.

Many, many hours later, here I am. Arrived in Charlotte. At my friend's house.

And this is the start of a series.

I'm going to call it money maxxing.

Here's where it came from.

Two days ago I did a video on selecting the target market with the highest ROI.

And I'm at a stage in this journal where I came across a multi page spread where I was doing what would now be called maxxing.

Maybe you've heard that word. Maybe your kids have.

And when I landed in Charlotte, I saw a sign.

An article saying Dictionary.com named maxxing the word of the year.

And you know what it means? Putting in an amazing effort to optimize something.

That's exactly what I see I was doing in each of these pages.

See, I was going through what are now the 8 Profit Activators.

And I was really spending time. Thinking about how to optimize each one of them.

So over the next several days I'm going to do a whole video on each one.

And we'll count the one we already did, selecting a target market, as the first.

We'll call that target maxxing.

Then this series goes through lead maxxing. Conversion maxxing. Offer maxxing.

All the way through to referral maxxing.

And here's what struck me reading these pages.

What I was really doing was spending deep thinking time. Looking at each element from many different angles.

Every attribute. Every piece of what I now call the 8 Profit Activators.

It's amazing to see the seed of them 30 years ago.

And to see how I've used them now in almost everything I do.

It's just become ingrained here.

Think about that for a second.

Most people never go back and optimize the thing they already have.

They build it once, roughly, and leave it running rough forever.

But the money is in the maxxing.

Taking each piece, one at a time, and asking... how good could this be?

Not building new. Optimizing what's already there.

That's the whole game.

So that's the message for today.

Just wanted to get in here. I've got to keep this streak alive.

Today makes a hundred and twenty eight days in a row of posting a video for you.

Right here on YouTube and Facebook.

We did it. I got in under the wire.

Tomorrow we start the series properly.

We'll do lead maxxing.

So tune in.

Show notes: https://deanjackson.com/podcasts/tol/144-money-maxxing-week/

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

How to choose a market with the biggest ROI Oct 24, 2026

Show notes

Good morning.

Just had breakfast, read through journal number eight. November of 1997.

And I was working out some thoughts on target market selection.

Here's the frame I had back then, and I still love it.

Nothing is as valuable as finding the super premium, highest value, highest probability audience that can most benefit from a collaboration with you.

Not who can we sell to. A collaboration.

How can you create an outcome for people?

Because the price you can charge depends on the outcome you can create. And the confidence people have that you can create it.

Now, most of the time when I take someone into a new target audience, I have to get them to close their eyes to who they've always served.

And look instead at their best capabilities. Who is the very best person for them to serve?

Sometimes it's a completely different person than the one they've got in front of them today.

And since we're in the Before Unit here, talking about people who don't know you yet... we may as well pick the ones that are the most profitable. The ones you can help the most.

So I'll take a whole session just to go through this.

And it starts with everyone.

Let's begin with the broadest possible audience of people you could help.

Then we narrow.

Geography first. If you're a local business, put a bubble around the town. Winter Haven, Florida. A 15 mile radius.

If you're a gym or a boot camp, maybe a 5 mile radius is all you need.

Blinders on everything else.

Because it starts with eliminating people.

This is an elimination and a sorting process. We're not committing to anything yet.

We're just finding the possibilities so we can evaluate them.

And here's a thing worth sitting with. Even if you've got national potential, artificially constraining yourself to one market lets you crack the code.

Figure it out in a test market. Then roll it out.

We learned that from Claude Hopkins.

So once we've got a geographic bubble, I ask people to exhaustively list every segment they could serve.

All the different types of people you could help.

Then... which one is the most profitable?

Which person, if you helped them, gives you the best outcome?

In real estate I always look for the highest, most desirable thing.

In Winter Haven that's lakefront homes. Somewhere else it's oceanfront, or golf course homes, or horse farms.

All valid. All valuable.

And then you compare them. On the numbers.

I always want an estimated total yield for the market.

Say Winter Haven has just over 2,000 lakefront homes. A 5% turnover rate. That's roughly 100 transactions a year.

At an average commission of 15 or 18 thousand dollars each.

That's a much higher total yield than a pile of condos turning over fast at a 7 thousand dollar commission.

High turnover isn't the same as high yield. Do the math.

Then the next question. How are we going to reach them?

Are there lists? Are these visible prospects, where you can get a list and point right at them?

Or are they invisible prospects, walking around where you can't tell who's who?

And often it's both at once.

If you're targeting chiropractors, those are visible. You can buy that list.

But if you ARE a chiropractor, your prospects are invisible. You can't see who twisted their back in the shower this morning.

So you ask... what do they read? What organizations do they belong to? Where do they hang out?

Are they actively looking for what you do?

And what would the first step be?

That's the whole evaluation. And it ends at one question. What do we do to compel these people to raise their hand?

Here's what I'd argue for you.

There's an ideal market you can help. The one where you make the biggest impact.

Narrow your focus to that one.

And everything downstream gets more profitable.

Show notes: https://deanjackson.com/podcasts/tol/143-how-to-choose-a-market-with-the-biggest-roi/

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

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