Thinking Out Loud with Dean Jackson

Good morning.

Here's a question that stopped me this morning.

How much money would you have right now... if you still had a relationship with every client who's ever paid you?

All of them still active. Still collaborating. Still getting value from you.

That's a whole different way to look at a business.

I found the page where this started for me. November 1996. Eben Pagan and I interviewing Don Peppers and Martha Rogers, the authors of The One to One Future.

You know how we got that interview? I called them up and asked. That was it.

Most people are more accessible than you'd think... when you come at it with what's in it for them.

I'd been living inside that book for six months, and it quietly rewired how I see a business. It's where the Before Unit, During Unit and After Unit really came from... especially the After Unit, where you nurture lifetime relationships and orchestrate referrals.

Eight ideas from that book stuck with me. Here they are, 30 years later.

Shift from market share to share of customer. Stop asking how many new people you can chase, and start asking how much of one person's lifetime you get to serve.

Collaborate with your customers. This is how we put realtors, mortgage brokers and home inspectors on the same team, all serving the same client.

Differentiate your customers. A first-time buyer is not the person looking for a horse farm. The closer people feel you were custom-designed for them, the better it goes for you.

Economies of scope, not scale. Deeper relationships with fewer people beats shallow contact with more... because you're not forever refreshing what you already have.

Manage your customers like an asset. This is your relationship portfolio. Take your top 150 relationships and manage them for a 20% annual yield. That's 30 transactions.

And 20% isn't hard when you really look at it. It just means one person, one time in five years, does one more deal with you or sends you one referral. That's it. That changes everything.

Engage your customers in dialogue, not broadcast. In 1996 that meant mail, and money. Today, with email and social, we've never had it better.

Take products to customers, not customers to products. Once you have the relationship, the only question left is... what else do they need? That's why I bring people GoGo, books, postcards. The relationship is the valuable part.

And make money protecting your customers' privacy. When you hold the relationships, people don't have to go hunt around for who to trust. You bring the right things to them.

Eight ideas. One thread running through all of them.

Your relationships are the asset. The marketing just fills the portfolio.

Read The One to One Future if you never have. I'm still drawing from it 30 years later.

Show notes: https://deanjackson.com/podcasts/tol/047-your-relationships-are-worth-more-than-your-marketing/

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Good morning. We're in journal number three now.

And a question keeps coming up... once you start journaling, how do you get all these ideas out of your internal world and into the real one?

Flipping back through, I can see the organizing model I've been using all along. Two tools, and your brain is really good at both.

The first is to tell the story of what's going to happen... narratively.

We used to do this at the big real estate main events. We called them ultimate scenarios. Relaxing music on, a few minutes to fill a page, writing from the perspective of your ideal customer who's just gone through the experience of working with you.

"I'm John Jones, and I just finished selling my house with Dean Jackson. From the moment we called him, the entire experience was amazing."

Get into real detail. Let yourself write it in the most glowing, wow-experience way you can imagine. People would rave about this exercise... because when we write words like that, we can't help but visualize.

The second tool is to take that scenario and lay it out as a timeline.

That's why my journals are full of these blocks moving across the page. Each box is a benchmark, something that needs to happen. Get a lead. Set up the 800 number voicemail. Take the leads off.

And here's the trick... right underneath each box is the perfect place for your mind to ask, well, what needs to happen to make THAT happen? You start thinking in checklists. Call sheets. A lead intake form. A letter for the people who didn't leave a phone number.

That's exactly how we built the Guide to Halton Hills.

And it's the beginning of what became the client experience timeline. Everything above the line is what your clients see and experience. Everything below the line is the systems, checklists and responsibilities that support it... what Dan Sullivan would call front of stage and backstage.

Thirty years later this is just instinct now. See the idea as a timeline, break it into component parts... which, for my ADHD brain especially, beats staring at the whole thing every time.

Try it out. I think it'll help you get your ideas from your journal into the world.

Show notes: https://deanjackson.com/podcasts/tol/046-how-i-get-ideas-from-my-head-to-my-journal-to-the-world/

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Thirty episodes in. We're already on journal number three.

Page 8. One of my favorite ads I've ever written.

File this one under... I'm not just the Hair Club president, I'm also a member. That seven-step checklist I shared a few episodes back? This is me running it live, on a real ad.

I had a friend of a friend. A very successful dentist. Two offices. Running a big full-page ad in the Yellow Pages. (For the kids: the Yellow Pages was a book that had all the businesses in it.)

And he wasn't happy. Didn't feel like he was getting his money's worth.

So I looked at his environment. And here's the thing about dental Yellow Pages ads... they're all the same. Clinic name big at the top. Years in practice. A laundry list of everything they do. Accepting new patients. Phone number.

You could swap the logos and nobody's response would change.

So we ran it through the checklist.

Single target market? The person flipping to the dentist page isn't browsing. They just chipped a tooth. They've got a toothache. They need a dentist right now.

A headline that tells the whole story? Need a dentist right now. That was it.

Does it look like news or an ad? We took a little white rectangle, business-card size, black bold type, and dropped it into a sea of yellow and color and dentist photos. It looked like a public service announcement. It slipped right past Broca's area... the part of your brain that filters out the ad messages.

A compelling offer. Conversational language. A crystal-clear call to action. If you're in pain and you need to see a dentist right away, call this free recorded message.

Then the recorded message did the rest. We can see you today. Leave your name and we'll call you right back.

Here's the punchline.

We went from a full-page ad to an eighth of a page. And we tripled the response.

The cost per new client fell through the floor.

Because we stopped trying to reach everybody... and spoke only to the people most likely to raise their hand.

That's the whole game. You sacrifice everyone else to be the obvious choice for the one person you actually want.

I love this stuff because you can keep score. You can see if you're winning.

Go look at one ad you're running... and ask who it's really for.

Show notes: https://deanjackson.com/podcasts/tol/045-this-idea-cut-ad-spend-by-87-and-tripled-the-response/

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Wrapping up journal number two, heading into number three, and one throughline keeps surfacing.

Being outwardly focused on exactly what your best prospects want... and then marching them to the benefit.

Not the features. Not the information. Not the thing you're offering. The benefit they actually came for.

Because the point of running ads was never to get leads. It's to get introduced to people who could become clients.

Here's the example that made it click.

Back in the early 90s I ran ads for the Guide to Halton Hills. Call a free recorded message, leave your name and address, and we'd mail it out.

The messages came back flat. "It's John Jones, here's my address, here's my phone number." Or, "I don't have an email address, thank you, goodbye."

Then I changed one thing. At the end of the message I said... tell me a little about the kinds of houses you're most interested in, and I'll send you the most recent listings.

The very next caller left all the usual stuff, then said, "We're in Mississauga now, moving out to Georgetown, we need a four-bedroom, and we'd love a pool."

One line. That's all it took.

And the reason it works is that you're assuming the best.

Assume the people asking for your guide, your book, your catalog... assume they genuinely want the benefit at the end of that path.

Take a hundred people who ask and you get a whole spectrum. Some are thrilled you offered to help. A few will actually get mad at you for assuming they wanted something, even though they asked. And everybody else sits somewhere in the middle.

Jeffrey Lant says it in Cash Copy... talk about the benefit your prospect desires, not the information you're sending.

Do nice things for people, even things they didn't ask for, and it gets reciprocated. That's Cialdini.

And Jordan Peterson has a rule I love... treat yourself like you're someone you're responsible for helping.

So flip that onto your leads.

What if you treated every one of them like you were responsible for helping them?

Remember Gary Halbert's provocation... what would you do if you had to get a response, or you'd be beheaded?

Same energy here. What would you do if you were responsible for helping the person who asked for your ebike catalog actually find the perfect bike for their family?

That's the place to come from.

Don't sit on the island waiting for people to swim ashore and beg you to help them.

Go out. Usher them across the river. Bring them onto the island where you can help them make all their wildest dreams come true.

It all starts with that one outward, service-oriented shift.

Show notes: https://deanjackson.com/podcasts/tol/044-what-happens-when-you-treat-every-lead-like-youre-responsible-for-helping-them/

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Page 170 of journal number two. November of 1996.

I'd been deep in The One to One Future, and something clicked about the realtors.

They spend all their time and money hunting the tiny slice of people who'll actually buy or sell a house this year. Call it a 5% turnover. Mail a thousand postcards and only 50 of those people are even in the market over the next twelve months.

So 95% of the money is adding no value to the homeowner... and none to the realtor either.

But here's the thing. A homeowner does a hundred things that have nothing to do with buying or selling.

What if you elevated yourself, and became their advocate for all of it?

That was the first version. I called it Household Helpers. A little mailing that made you the person a homeowner knows and likes and trusts, long before they ever think about selling.

And the beautiful part is nobody appoints you to that job. It's self-appointment only. Nobody's standing in your way.

Nobody's going to stop you from being the advocate for homeowners... or lakefront owners... or drivers in your county.

So I made a household emergencies handbook. A little folded card with a directory of everything that can go wrong in a house. Broken window. Leaking roof. Clogged drain. Locked out. Bugs. A garage door that won't open.

Then an auto emergencies handbook for the glove box. Flat tire, dead battery, keys locked inside, who to call.

All the businesses that fix those things are mailing everybody too, just hoping to catch the one person who needs a garage door today. Just as wasteful.

Put yourself at the center of the category instead, and you're the one adding the value.

Do it today and it's even easier. A QR code in the glove box. The moment somebody's in an accident, they scan it and there you are, walking them through exactly what to do.

I've got a friend here who's a personal injury attorney. Most people spend their whole life hoping they never have to meet him.

So imagine building a coalition around lowering accidents, or distracted driving... a common cause everybody rallies to. Your name is on the good thing long before the bad thing ever happens.

You see these 9 by 12 postcards now, selling 16 spots willy-nilly to whoever wants one. The elegant version is a category card, where everything on it lines up around a single topic.

Because the moment you categorize something, it becomes more valuable.

This is one of those ideas that's stuck with me for 30 years and keeps evolving. And I've never had anyone really take it and run.

Maybe it's you.

Show notes: https://deanjackson.com/podcasts/tol/043-the-more-helpful-you-become-the-less-you-have-to-sell/

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Page 179 of journal number two. Fall of 1996.

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

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

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

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

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

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

Let me give you a few off that page.

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

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

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

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

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

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

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

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

Then fill the page.

I think you're going to surprise yourself.

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

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

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

Dramatic. But stay with it.

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

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

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

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

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

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

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

Then Gary's favorite move. The grabber.

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

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

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

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

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

The 9-word email.

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

What would you write?

That's the level of thinking. Start there.

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

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Happy Monday. Beautiful morning for July.

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

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

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

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

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

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

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

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

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

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

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

So that's your nudge for today.

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

Let me know how it works out for you.

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

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

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

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

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

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

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

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

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

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

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

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