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 Know What To Do When Something Goes Wrong With a Customer Jul 25, 2026

Show notes

Good morning.

If you're growing your business, you're going to involve other people.

And once other people are involved... things are going to go wrong sometimes.

The real question is whether everybody already knows what to do when they do.

I was looking through journal number three this morning and found a page from Steve Kross.

Steve was a Century 21 broker in New Jersey. Ran a very successful office. He'd come and speak at the big seminars I was doing around the country with Joe Stumpf.

A gentleman in every way. And full of wisdom about how to handle the business.

He used to tell a story about a Kentucky Fried Chicken.

An older gentleman had been coming in every week for a long time. Same order every time.

Then one day the counter is busy, the cashier is brand new, and what this man always got was a little outside the way things are normally done.

So the new employee goes by the book. Says no.

And has no idea he just made a $5,000 mistake. Because alienating your best customer is never a small thing... it just never shows up on the receipt.

That's why Steve had three questions. If everybody in the organization is aligned around them, everybody knows what matters in the moment.

Question one. From the customer's point of view, am I treating this customer with the utmost respect?

Not taking a hard line. Not flexing authority. Not because I said so, or that's not how we do it here.

Question two. Am I exceeding the customer's expectation?

When somebody comes to you with a complaint, they're already carrying an expectation of how this is going to go. Usually not a good one.

And if you lean into it, you're feeding exactly the thing they were braced for. The divide grows... in front of them, and in front of everybody else who's watching.

Question three. Is what I'm doing in the best long-term interest of the customer?

Sometimes that means making a concession you didn't have to make.

And sometimes it means letting a customer go. That can be the long-term interest too.

They say people might not remember what you said, but they remember how you made them feel.

I've passed this page a few times now in journal three. And every time, I remember how it felt to come at things that way. Resolving instead of defending.

The other use for the three questions is afterward.

Somebody on your team has been through a conflict. Sit down together and walk the checklist. Did we treat them with the utmost respect? Did we exceed what they expected? Was it in their long-term best interest?

That's how a team ends up with one unified way of handling things, instead of three people handling it three different ways.

So here's your nudge for today.

Take the last time something went wrong with one of your customers... and run it back through the three questions.

You'll know pretty quickly whether you handled it, or just survived it.

Show notes: https://deanjackson.com/podcasts/tol/052-how-to-know-what-to-do-when-something-goes-wrong-with-a-customer/

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

"WOW" Experiences Don't Happen By Accident Jul 24, 2026

Show notes

Good morning.

Journal number three. And it keeps happening... I'm reading pages from 30 years ago and finding the exact things I still do today.

One pattern shows up more than any other. Storyboards.

I've mentioned them before. But what I'm seeing now is what they really are. A focusing tool.

Here's the whole trick. Put a pen in your hand. Put a piece of paper in front of you. Write one instruction across the top.

And your mind has no choice. The pen forces you to think about only that thing. It gives your thoughts somewhere to go... out of your head and onto the page.

Page 111. The thing I was working out was a storyboard I called the seven-phase buyer wow cycle.

The magic is in breaking the journey into its segments. Where does somebody actually start? Where do they cross into the next stage?

Think about this cafe I'm sitting in. Lay out the whole experience through the eyes of a first-timer. The parking lot. The door. Walking in. Where do their eyes go? What are they looking for?

How do you make it so nobody feels out of place or confused? Because being a regular somewhere is a completely different feeling than your first time.

And that's the hard part. We're too close to our own thing. We know what it's supposed to be, so we can't see it fresh anymore.

Getting into the eyes of a brand-new person takes some creativity. Identifying the segments is what unlocks it.

So phase one of the buyer wow cycle... find someone looking for a home, and be so helpful they want to meet with you. That's the whole Before Unit, really. The eight profit activators are just this same storyboard, laid out as a timeline.

Then the appointment. What has to happen for them to feel secure with you? Then you go out and look at homes. Every one of these phases is full of little places to create a wow.

Take phase four. The conditional period. They found the home, the offer's accepted, and now you're removing conditions. For someone who's never done it, that stretch is nerve-wracking. Precarious.

So how do you create a wow right there? A daily check-in call. Getting the inspection booked. Pushing the mortgage approval along. Once you can see what the moments are, you can turn each one into a process.

That's the thing I keep coming back to. Look at the experience someone goes through with you. Find the benchmarks. Think of them like the locks in a waterway... each one lifts you to the next level.

What triggers the entry into a phase? How do you create a wow while they're in it? What's the exit into the next one?

Every page in the journal is a chance to walk it through. Tell the story to yourself. Imagine the ultimate version. Describe it from the buyer's side. Then isolate the pieces that need to be built or systemized to make it real.

That's a lot of what journal number three was for me. Laying these experiences out, one page at a time.

Because here's the truth underneath all of it. Every idea I've had, every dollar I've made in 30 years, went through my brain, down my pen, onto a page in my journal... before it ever went out into the world.

So here's your nudge for today.

Pick one experience somebody has with you. Walk it, box by box, through the eyes of a first-timer.

And find the one place you could turn into a wow.

Show notes: https://deanjackson.com/podcasts/tol/051-wow-experiences-dont-happen-by-accident/

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

9 Reasons “Time Management” Fails Your Entrepreneurial ADHD Brain Jul 23, 2026

Show notes

Good morning.

We're almost halfway through journal number three.

And I keep noticing the same thing on these pages... my undiagnosed ADHD, rearing its head, trying to work out why I can't seem to be a normal boy.

The question sitting underneath all of it. Why doesn't time management ever actually work?

I found nine reasons. So here they are.

One. We don't know what we want. My decider is broken. Every option feels equally possible, all at once, and I freeze on choosing one. So I run elimination tournaments... eight things in a bracket like the NCAA, played off against each other until one is left standing. Then I can finally focus.

Two. We don't put first things first. I drift to whatever's newest and most interesting, not the thing I already know matters. Nothing moves for me until it becomes a deadline. I love them and hate them at the same time.

Three. We focus on the wrong time frame. Time moves at the speed of reality... 60 minutes an hour, no matter how fast my head insists it's already done. The only actionable time frame is today. A thousand waking minutes. And really, the next 100. I run the day in ten-minute blocks, and you'd be amazed what fits in one of them.

Four. We don't leverage our time. Jay Conrad Levinson's 90-minute hour. If something takes 30 minutes and you can do something else alongside it, you've stretched the hour. Go for the walk and listen to the podcast. Stack it, batch it, multiply it.

Five. We don't allow ourselves to be supported. Michael Gerber's point. As we grow we cling to the things we think only we can do. The real move is to look at your pile and ask... is there anything here somebody else could do for me?

Six. We don't have systems for the routine. If you keep hitting the same snag again and again, that's time debt piling up. So I put a garbage can right outside the car door in the garage, and the junk on the passenger seat never makes it into the house. A bowl by the front door for the keys I always lost. Little systems, made easy.

Seven. We are in time debt. All the things you've been putting off weigh on you exactly like financial debt. So make the list. What do I owe, and to whom? Then run a time-debt snowball, Dave Ramsey style... knock off the fastest one first, feel the progress, keep going.

Eight. We don't have the energy. Procrastinating is exhausting. A block on the calendar is worthless if you're too drained to use it. That's why I've become what Brian Johnson calls a professional sleeper.

Nine. We are afraid. Afraid to set the big goal. Afraid of what taking action might mean. Afraid of failing. So we quietly shrink the whole thing down.

Here's a side note that surprised me. Almost everything I feel real pressure about involves somebody else. Someone's waiting, someone's expecting it. I never seem to feel that pressure just from myself.

And that's the fun of a journal. Nine reasons, sitting on one page of book number three, still explaining my whole week 30 years later.

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

I laughed. Because... yes. That's exactly what I do.

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

So here's your nudge for today.

Take the thing you keep putting off... and just ask what happens if you don't touch it in the next 100 minutes.

That one question tells you what actually matters.

Show notes: https://deanjackson.com/podcasts/tol/050-9-reasons-time-management-fails-your-entrepreneurial-adhd-brain/

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

The Most Underrated Day in Your Week Jul 22, 2026

Show notes

Good morning.

The last week of November, 1996. My very first Strategic Coach workshop in Toronto.

That's the day Dan Sullivan started me on a 30-year habit he calls thinking about your thinking.

I'm looking back at the notes I took in that first room. An industrial part of the city, beautiful old brick buildings, lofty loft spaces. Everything about it was built to make you think bigger.

And on day one, Dan laid out something I still run my whole life by. He calls it the entrepreneurial time system.

The idea is that an entrepreneur's time works like an athlete's or an entertainer's. You've got game days, practice days and off days.

Dan renames them. Focus days, free days and buffer days.

Focus days are easy to picture. They're the days you do the money-getting thing. Workshops, clients, coaching, whatever you actually get paid for.

Free days are the ones most people get wrong. Dan means a full 24 hours completely disconnected from work. Not slipping out at lunch for a movie and feeling like you got away with something. The day off is the whole point of the day.

Mine evolved into what I call super happy fun days. You orchestrate the whole thing, start to finish, filled with the stuff you love. Breakfast at your favorite place. A round of golf with a good friend. Lunch at the club. A movie. Dinner. A spa. All in one day.

But a day like that doesn't happen by accident. And that's where the underrated one comes in.

The buffer day.

I used to treat buffer days as the junk drawer of the week. The in-between. Catch up, do whatever's left over, whatever needs doing.

I had it backwards. The buffer day is the power move.

A buffer day is where you proactively plan and set up your focus days and your free days so they actually land. It's where the thinking about your thinking happens.

That's why I spend so much time in my journals. I'm sitting on a buffer day, drawing out the things I'll do on my focus days and lining up the things I want on my free days.

One thing I love to do is make a list of 26 things that bring me joy. There's no magic to 26. It's just the number of lines on a page in my journal.

Put a constraint on it and your brain gets to work. It does what you ask it to do.

Now that list is a menu. On a buffer day you pick from it, put it on the calendar, and enroll the people you want there with you. That gives everybody something to look forward to.

If you want an on-ramp to all this, don't try to build your perfect week this week.

Treat your calendar like the weather forecast.

You're a storm of activity moving through the days. You know exactly what today and tomorrow hold, same as a meteorologist knows the next couple of days cold.

But go out 14 days and it opens up. Pick three Tuesdays from now and it's easy to drop a beacon in there. A super happy fun day. A real buffer day. Once it's on the calendar, everything else works around it.

My friend Taki Moore calls it spanxing your calendar. Squeeze all your focus days into Tuesday, Wednesday and Thursday, and let the rest breathe.

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

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

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

So here's your nudge for today.

Stop treating the buffer day like a throwaway.

Give it a job. Use it to plan the days that actually matter... and watch how much better the rest of your week gets.

Show notes: https://deanjackson.com/podcasts/tol/049-the-most-underrated-day-in-your-week/

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

Some Ideas Are Worth Having Even If They Never Happen. Jul 21, 2026

Show notes

Good morning. Day 33 out here.

I opened the journal this morning to a page titled “Eben’s brilliant idea number 1009.”

That number tells you everything. We weren’t precious about these. We were just riffing.

This was 1996. Eben Pagan and I were flying all over the country doing real estate seminars, and in between we were flexing our creative wings. Book ideas. Business ideas. Just to see what we could come up with.

Almost none of them came into the world. And that was never the point.

The point was the exercise. Letting yourself think about something with no constraint... without censoring the idea before it’s even finished.

Because every so often, one of those throwaway riffs turns out to be a seed.

Here’s one. Popular psychology says you can’t change other people, only yourself. So we took the opposite side. How to Change the One You Love.

I can see now that was the seed of Stop Your Divorce. And a book I did with a hypnotist called Hypnotize Your Husband. Same thread running underneath... we all quietly want to change somebody else’s behavior.

We even mapped out how the book could write itself. Ask a hundred women the one thing they’d change about their husband. Then hand the answers to a panel of professional change agents... a dog trainer, a lawyer, a drill sergeant, a priest, a hypnotist. In your professional opinion, how would you change this behavior?

A cartoon for each one. Graphic, a little satirical. The kind of book people buy as a gift.

Because that’s the real lesson sitting underneath it. It’s not always the best book that wins. Sometimes it’s the most provocative one.

Look at Mark Manson’s The Subtle Art of Not Giving a F***. Almost all of that success is the title. There are twenty books with more useful information inside... presented in a way nobody picks up.

Then there was the Tube of Joy.

We were sitting in an airport and sketched out a kiosk of nice tubes you could give as a gift. A golf tube with balls, tees and a towel. A tennis tube with grips and a magazine. A wedding tube, a baby tube, a birthday tube.

Impulse gifts, right there the moment you need one.

None of it happened. But the engineering drawings are still right here in the journal, and the fun of it was the whole reward.

It’s like a band jamming. You’re not trying to write the hit. You’re just playing... and now and then, out of the noise, comes the seed of something real.

So that’s your nudge for today.

Let your mind go. Ask “what if” with no constraints on yourself.

Some ideas are worth having even if they never happen. And once in a while... one of them turns into something.

Show notes: https://deanjackson.com/podcasts/tol/048-some-ideas-are-worth-having-even-if-they-never-happen/

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

Your Relationships Are Worth More Than Your Marketing Jul 20, 2026

Show notes

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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How I Get Ideas From My Head, to My Journal, to the World Jul 19, 2026

Show notes

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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This Idea Cut Ad Spend By 87%... And Tripled The Response Jul 18, 2026

Show notes

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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What Happens When You Treat Every Lead Like You're Responsible for Helping Them Jul 17, 2026

Show notes

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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The More Helpful You Become, The Less You Have to Sell Jul 16, 2026

Show notes

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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