Thinking Out Loud with Dean Jackson

I Almost Can't Believe I've Gotten Away With This Daily Schedule Over 30 Years

dean@deanjackson.com (Dean Jackson) — Wed, 08 Jul 2026 00:00:00 GMT

This one starts on page 31 of journal number two. Back then I'd just picked up Dan Sullivan's How the Best Get Better and gotten hooked on two ideas. Unique ability, the thing at the core of what you do that energizes you and needs no amping up. And the entrepreneurial time system, three kinds of days: focus days spent in your unique ability, free days with nothing to do with work, and buffer days to prepare for both. I overlaid that lens onto a weekly schedule, and I kind of laugh now, because the schedule I sketched in 1996 is almost identical to the one I run today.

Here's the thing I keep coming back to. Time hasn't changed in 30 years. Same 24 hours, life still moves at 60 minutes an hour, and the only time we ever get to do anything is now. So I stopped trying to reinvent the rhythm and leaned into it. Bed at 11, up by 7:30, in the car by 8. My ADHD brain loves that deadline, it's almost magical how I never miss it. Same breakfast spot every morning, journal open, whatever pops out becomes the day's insight. Then straight across the street to the coffee shop, 9:30 to noon, no phone, no appointments, no interruptions. That's my unique ability time, writing, solving marketing puzzles, hatching evil schemes.

Early in real estate I played the game like Tetris. Time's moving, the blocks keep falling, and you're shifting and reacting and hoping it all fits. Now I treat it more like Guitar Hero. The notes still come at you, but they've been pre-arranged, so if you just play the right ones in the right slots, the day sounds ordered and purposeful. Appointments only land Tuesday, Wednesday, Thursday afternoons. Friday through Monday, nothing scheduled. Wrap by six, and the evening is just for living.

I'll be honest about where I still struggle. That 10-to-noon block is the hardest part for an ADHD brain. I've got the time, but choosing the one thing to work on out of everything I could do is the real fight. Ned Hallowell calls it VAST, too many open loops pulling at you. So it's still a work in progress after 30 years. I've got a new paradigm I've been chewing on from some conversations with Dan Sullivan, and I'll get into that tomorrow.

Show notes: https://deanjackson.com/podcasts/tol/035-i-almost-cant-believe-ive-gotten-away-with-this-daily-schedule-over-30-years/

I Predict These 7 Business Categories Will Survive & Thrive In The NEXT 30 Years

dean@deanjackson.com (Dean Jackson) — Tue, 07 Jul 2026 00:00:00 GMT

I found a little time capsule, page 20 of journal number two from 1996. Back then I was chewing on the idea of advocacy from The One to One Future and applying it to real estate. The realtor business is transactional. You sell someone a home and move on, even though 84% say they'd use that agent again and fewer than 25% actually do. The number one reason is they lost touch. That's a valuable relationship left on the table.

Looking back 30 years, I realized I was onto something with the things that don't change. I predict these seven categories survive the next 30 years. The context stays the same even if the content shifts. Home is the biggest line item, everything to do with the house. Food, because we're still 100% human and haven't merged with the robots yet. Cars and transportation. Kids, a whole economy on its own. Money, including debt, investing, and business owners spending to bring money in. Health, as the boomers and Gen X age into longevity. And me, the discretionary pleasure spending on travel, hobbies, and entertainment.

Everyone frames AI as disrupting things. I think the better question is how AI can enhance these seven. Pair it with the categories people already spend on and you're building on durable ground. Over 85% of the average household budget is spent within five or ten miles of home, which is why HVAC and home service companies keep thriving. That need isn't going anywhere.

Overlay advocacy on top of any of these and you've got a position. Instead of thinking about the one narrow spoke you provide, elevate out and become the person's advocate for the whole category. With realtors, that looks like being a home advocate for anything to do with their house. Take the one to one future and apply it to whatever category you're in, and you've set yourself up for the next 30 years.

Show notes: https://deanjackson.com/podcasts/tol/034-i-predict-these-7-business-categories-will-survive-thrive-in-the-next-30-years/

Stop Trying to Convince People. Just Start Telling the Truth & Watch What Happens…

dean@deanjackson.com (Dean Jackson) — Mon, 06 Jul 2026 00:00:00 GMT

This one goes back to the summer of 1996, when I read Jerry Spence's How to Argue and Win Every Time and realized the real tool isn't the pitch, it's the story. Stack that on Cash Copy and Robert Cialdini's Influence and you stop collecting separate lessons and start owning a durable model you can use again and again.

The first time I used it, I had a developer client north of Toronto with six unsold cottage lots in Muskoka, and it was already past Labor Day. His ads looked like ads, 33% off, blowout sale, all of it trying to convince people. So I asked the only question that matters. What's the truth here? The truth was he had a balloon payment coming due on another property and needed these lots sold to make it.

We had the lots appraised so the discount carried real authority, then I wrote the ad as a newspaper article in his own voice. I need to sell these six Muskoka home sites in the next 30 days, 33% below their appraised value, and here's my dilemma. When you put your sword down like that, people stop resisting and get curious. He sold all six lots in two weekends and blew out his fax machine.

That became a permanent hammer in my toolkit. A townhouse that sold over asking in a single weekend. A giant postcard for Joe Polish's house at the top of Camelback Mountain, an open letter to anyone who ever wondered what it'd be like to live up there. The move is always the same, tell a story that lets the other person feel like they're winning. Thirty years later I'm still running this exact playbook.

Show notes: https://deanjackson.com/podcasts/tol/033-stop-trying-to-convince-people-just-start-telling-the-truth-watch-what-happens/

30 years later people still spend their money on these core things.

dean@deanjackson.com (Dean Jackson) — Sun, 05 Jul 2026 00:00:00 GMT

Filing this one under we are living in the future. As I close out journal number one, a couple of books from 1996 planted ideas that have stuck with me for 30 years. The Discipline of Market Leaders says businesses win as product leaders, operationally excellent companies, or customer intimate companies, and I realized real estate is really all three across the before, during, and after units.

The One to One Future by Don Peppers and Martha Rogers predicted the privacy issue and imagined a future where we'd each have an advocate, someone we share everything with who acts as our intermediary with the marketplace. I coupled that with the customer intimate idea and saw the opening.

Then I mapped the cradle-to-grave list of where people spend money, from babies and toddlers through weddings, homes, cars, and retirement. Every one of those is a contextual certainty, something lots of people are moving through, and almost nobody steps up to organize the category and be their advocate.

The biggest prize is the first-party relationship with a homeowner, which is why companies like Rocket are combining mortgage, insurance, and brokerage. Whatever your business is, start asking who else serves the same person. That closes journal number one, 17 episodes in, with about 150 journals still to go.

Show notes: https://deanjackson.com/podcasts/tol/032-30-years-later-people-still-spend-their-money-on-these-core-things/

How I talk my ADHD brain into doing the thing I'm procrastinating now

dean@deanjackson.com (Dean Jackson) — Sat, 04 Jul 2026 00:00:00 GMT

Do you ever wonder who you're talking to when you talk to yourself? Some of my best conversations have happened in my own head, and going through my journals I found the first of many written-out dialogues where I play both parts to talk my ADHD brain into doing what I'm avoiding.

An ADHD brain only really has two time frames, now and not now. If something isn't due right now, it's a future Dean problem. And when you're procrastinating, you're usually procrastinating the noun of the task, the big thing like finish expired package that you can't take action on.

So the dialogue narrows me down. What would you actually have to do to finish it? I list the real steps, estimate how long each takes, figure out which part I'd enjoy most and which I could delegate, then nail down a specific time and place to do it.

The next morning I wrote that I was amazed how well it worked and was looking forward to doing it again. It stuck. This exercise on its own can help you take something you're stuck on right now and actually get it done.

Show notes: https://deanjackson.com/podcasts/tol/031-how-i-talk-my-adhd-brain-into-doing-the-thing-im-procrastinating-now/

A 7-Step Checklist That Instantly Improves Any Ad, Postcard, or Mailer

dean@deanjackson.com (Dean Jackson) — Fri, 03 Jul 2026 00:00:00 GMT

Back in July 1996, Eben and I were touring the country doing real estate seminars, and I'd run an ad clinic where people submitted their ads and postcards. I came across the seven-step checklist I used, and it's just as durable today as it was pre-internet.

It starts with the target: have you selected a single market, so the right person instantly knows this is for them? Then does your headline tell the complete story on its own? Once you've got the right person and a headline that pulls them in, most of the job is done.

The rest of the checklist covers making it look like news instead of an ad, using conversational language, having a compelling offer, being crystal clear about the one action you want, and using words that let people get something instantly without talking to a salesperson.

I explain Broca's area, the part of the brain that filters out ads so you can ignore billboards and skip commercials, and why packaging your message as content sneaks past that filter. There's also the test I always come back to: if this postcard were you delivering the message in person at someone's door, would you actually pay to have it said that way?

Show notes: https://deanjackson.com/podcasts/tol/030-a-7-step-checklist-that-instantly-improves-any-ad-postcard-or-mailer/

You Don't Actually Want More Money

dean@deanjackson.com (Dean Jackson) — Thu, 02 Jul 2026 00:00:00 GMT

Going back through my journals, I found the seed of what I've wanted for 30 years. In Los Angeles in June 1996, talking with Eben, I realized what I really want isn't a sum of money. It's a feeling. What everybody wants is peace and power, and I've come to understand that power as agency, being able to live your life however you choose.

I'd started watching other entrepreneurs get totally absorbed by their businesses, waking up every day to put out fires and chase a self-induced urgency. I didn't want to trade anything for that life.

That trip introduced me to La Jolla, and it crystallized the hub-and-spoke way I still love to live. Later I named the three lifestyle elements I'm after: daily joy, abundant time, and financial peace. The temptation when you're young is to keep stacking on things that cost you time and create stress.

Hustle culture treats a lifestyle business as somehow lesser, but ask whether the 10x actually adds any daily joy or abundant time. My friend Taki Moore calls the answer a lifestyle empire, an eight-figure business built only around what you love. It works because of marketing, the lever that funds the life you really want.

Show notes: https://deanjackson.com/podcasts/tol/029-you-dont-actually-want-more-money/

Why the Best Marketers Make Ads That Don't Look Like Ads

dean@deanjackson.com (Dean Jackson) — Wed, 01 Jul 2026 00:00:00 GMT

This wraps up my little series on the four cornerstones of being an enduring marketer. We've covered behavioral psychology, your own frameworks, and copywriting. The fourth is what I put under the umbrella of design, meaning how you package and present your message so people actually consume it.

One of the most durable things I picked up early is making something look like news instead of an ad. When your message looks like content, people read it through a different lens than they use to filter advertising. I'm not talking about flashy or artistic, just practical presentation that draws the eye.

Spending a day with Jerry Ballinger, I saw how much attention he paid to layout, and I decided to learn to do it myself in PageMaker so there was zero friction between my ideas and getting them into the world.

I use two filmmakers to make the point. Robert Rodriguez says learn the technical skills and become dangerous. Terry Gilliam told Tarantino your job isn't to get your vision on the screen yourself, it's to describe it clearly and hire the best people. With AI and today's tools, that second approach matters more than ever. The four cornerstones haven't changed, only the ways we create and distribute them.

Show notes: https://deanjackson.com/podcasts/tol/028-why-the-best-marketers-make-ads-that-dont-look-like-ads/

90% of Copywriting Comes Down to 4 Words

dean@deanjackson.com (Dean Jackson) — Tue, 30 Jun 2026 00:00:00 GMT

I learned four words from Jeffrey Lant that carry about 90% of what you need to write copy that works: you get benefit now. If any word you write doesn't sit under one of those pillars, you're on the wrong path.

The mistake almost everyone makes is thinking their prospect cares as much as they do about them and their product. Nobody cares that you're the leader or that you've spent your life at this. They care about what they get. I share the Stop Your Divorce letter that opens completely on the prospect's wants and has sold over $5 million from one sales letter I wrote in 1998.

I'll walk you through the exercise I run on any piece of copy: strip the adjectives and adverbs, look at the nouns and verbs, and ask if you're actually saying anything real. Then read it as your prospect and ask whether that's how they'd want to be introduced to your message.

I also give you the people worth studying: Jeffrey Lant's Cash Copy to start, plus Dan Kennedy, Jay Abraham, Gary Halbert, John Carlton, and Brian Keith Voiles. Nearly every dollar I've made in 30 years came from something I wrote or said.

Show notes: https://deanjackson.com/podcasts/tol/027-90-of-copywriting-comes-down-to-4-words/

The Psychology Behind Why People Buy

dean@deanjackson.com (Dean Jackson) — Mon, 29 Jun 2026 00:00:00 GMT

If you want one place to start with behavioral psychology, go down the path of social psychology. The most cited name in it is Robert Cialdini, and I read his book Influence back in 1996. There's a direct through line from that moment to everything I do today.

Cialdini calls them the six weapons of influence, things hardwired into us that shape our decisions without us knowing. Reciprocity is the first. Do something nice for someone and they feel they owe you one back.

That's why I lean so hard on giving away free books. It starts a relationship, and it stacks with commitment and consistency, where once you've raised your hand for something you feel pulled to keep moving in that direction.

Technical skills go obsolete. Everything I learned about building sites in Microsoft FrontPage is useless now. These psychology principles are durable, so I'd start with Influence and Pre-Suasion, then Predictably Irrational by Dan Ariely.

Show notes: https://deanjackson.com/podcasts/tol/025-the-psychology-behind-why-people-buy/

Turning Buyer Psychology Into A Marketing Model

dean@deanjackson.com (Dean Jackson) — Mon, 29 Jun 2026 00:00:00 GMT

The second cornerstone is creating mental models, frameworks you can overlay on a situation to give yourself a shortcut. Michael Gerber's franchise prototype was the first one I was ever exposed to.

My model was simple. Create a guide, run ads to get people to raise their hand, then treat them like someone who's going to buy and give them valuable information. I've since learned that's roughly a 50% chance over the next two years.

I'm not trying to convince anyone up front. I'm identifying the invisible prospects who are already thinking about buying, then letting reciprocity, liking, and commitment and consistency do their work. Those eight profit activators grew out of this exact thinking.

There's a line I love: a man with an experience is never at the mercy of a man with an idea. Take whatever you do, build your own model, document it, and you'll trust that anything you run through it has a better shot.

Show notes: https://deanjackson.com/podcasts/tol/026-turning-buyer-psychology-into-a-marketing-model/

Master These 4 Marketing Skills First...

dean@deanjackson.com (Dean Jackson) — Sat, 27 Jun 2026 00:00:00 GMT

A man named Jerry Ballinger shaped a lot of my thinking when Eban and I were in our late twenties. Looking back, everything I've done traces to four cornerstones I picked up around him.

First is behavioral psychology, understanding why people do what they do so nothing baffles you. Second is building mental models and frameworks, like knowing music theory so your ideas fit together instead of being random.

Third is copywriting, which I really mean as communication in every form, speaking and writing your ideas so people accept them and change. Fourth is design, framing your message so there's zero friction between your idea and the world.

AI can help with all of it now, but the thing that hasn't changed is behavioral psychology. People still do what's in their own self-interest, and if you frame your ideas around that, you win.

Show notes: https://deanjackson.com/podcasts/tol/024-master-these-4-marketing-skills-first/

The Less I Do, the Richer I Get.

dean@deanjackson.com (Dean Jackson) — Fri, 26 Jun 2026 00:00:00 GMT

San Francisco, 1996, sitting across the bay from the city with Eban Pagan. This is where I first felt income showing up that didn't come from my own effort.

Eban and I mapped out a system where every piece, the ads, the voicemail, the follow-up calls, the newsletters, could be done by other people. The less I did myself, the more I could actually make.

What most people really want isn't to do the work. They just want someone ready to buy or sell. So the goal grew from replacing me to replacing the client too, doing everything for them.

Back then it was outsourcing to other humans. Now it's AI, which I couldn't have imagined in 1996. Same core model though: build something that runs without you, then duplicate it.

Show notes: https://deanjackson.com/podcasts/tol/023-the-less-i-do-the-richer-i-get/

If You're in Business & Have ADHD -- Watch This...

dean@deanjackson.com (Dean Jackson) — Thu, 25 Jun 2026 00:00:00 GMT

The foundational thing behind everything I've built is a duplicatable model. Michael Gerber taught me to treat the business as the product, something separate from me, not something I identify with.

My guide to Halton Hills was one core unit I could copy again and again. Toronto and Beyond was just that same thing duplicated, the way Ray Kroc built Hamburger University to prototype every McDonald's.

I'm great at getting something scale-ready, cracking the code the first time. I'm not the guy who wants to sing the same song every night on tour, and that's the first place I can see my ADHD wiring, looking back.

Most businesses live in a five-mile bubble. If you can make something work in one market, you've got the key to duplicate it. So look at your own business and ask what parts you could copy.

Show notes: https://deanjackson.com/podcasts/tol/022-if-youre-in-business-have-adhd-watch-this/

These 3 Principles Built A $2 Trillion Company

dean@deanjackson.com (Dean Jackson) — Wed, 24 Jun 2026 00:00:00 GMT

I'm 30 years into journaling every day, and I've been reading back through journal number one from 1996. Some patterns in me haven't changed, and neither has human nature.

Back then, the realtors I was coaching expected to run an ad today and sell a house this weekend. I had to learn something harder, that investing time to build a system with a future payoff beats chasing the immediate result.

What struck me is that sellers wanted the exact same thing in 1996 as they do now. Sell fast, get the most money, least hassle. It's the same bet Jeff Bezos made building Amazon around what people would always want.

If you keep people focused on the result they really want, and you handle whatever it takes to get them there, that hasn't changed in 30 years and I don't think it'll change in the next 30.

Show notes: https://deanjackson.com/podcasts/tol/021-these-3-principles-built-a-2-trillion-company/

Cold Calling Worked. That’s Why I Stopped Doing It.

dean@deanjackson.com (Dean Jackson) — Tue, 23 Jun 2026 00:00:00 GMT

I'm a creature of habit, and going through 150 journals made me see how much of life is a kind of Groundhog Day. What kept jumping out at me was the growing wake of intellectual property I've built up over the years.

Cold calls work. That's not the problem. The problem is there's no residual value, so the second you stop, the results stop. Michael Gerber's E-Myth taught me to put things into a format I could use again and again, which is how I built the Halton Hills guide and licensed it to 40 agents.

One project in this journal was the Home Buyer College, a set of education pieces we mailed to people who'd buy a home in the next year or two. It started as physical mail and became the email follow-up sequences we still use today. Eben Pagan and I would mine Cosmo covers for headline formulas to make it all land.

The lesson I keep seeing is how valuable it is to package and document what you know. Every piece builds on the last, and 30 years later they're still creating value in the world.

Show notes: https://deanjackson.com/podcasts/tol/020-cold-calling-worked-thats-why-i-stopped-doing-it/

If I Ran Your Marketing, Here’s Exactly What I’d Do...

dean@deanjackson.com (Dean Jackson) — Fri, 19 Jun 2026 00:00:00 GMT

This one's a full walkthrough. I take you through exactly what I'd do if I walked into your business tomorrow and took over the marketing, starting with the before unit, the part that finds people who want what you do.

I'd begin with fresh eyes and one hard question. What could you do if you only got paid when the client got the result? That's where the real money is, and it's how the Koch brothers grew their company by investing in the outcome alongside their partners.

From there it's selecting a single target market at the highest level, then figuring out whether your prospects are visible or invisible. The best way I know to get invisible prospects to raise their hand is to offer a book, so I walk through my five title formulas and the word palette I use to build them.

Once someone raises their hand, I show how I think about them as an asset, why about half will act within 100 weeks, and how to greet them and make an offer so easy they can't help but take the cookie. It's the whole profit activator model in one sitting.

Show notes: https://deanjackson.com/podcasts/tol/019-if-i-ran-your-marketing-heres-exactly-what-id-do/

How I tricked my ADHD brain into building my business & life

dean@deanjackson.com (Dean Jackson) — Sun, 14 Jun 2026 00:00:00 GMT

I've kept a journal every day for more than 30 years, and it's without question the most important habit in my life. As an introvert, writing is how I think out loud and have a conversation with myself.

Journal number one is where I first met the Myers-Briggs types and found out I'm an INTP. Knowing how you're wired is an advantage. Over the years I added the Kolbe and Working Genius, and the lesson hasn't changed. Don't fight your natural tendencies, change your environment to support them.

So instead of forcing myself to be tidy, I ask my mind a guiding question. I write down the question, paint a picture of exactly what the ideal looks like, then list every idea I can think of to get there. Your mind loves to solve problems if you give it the question and a pencil.

I've been using that guiding-question format for 30 years, and it evolves into something even better a few journals from now. More to come.

Show notes: https://deanjackson.com/podcasts/tol/018-how-i-tricked-my-adhd-brain-into-building-my-business-life/

The 1996 Marketing Idea That Changed My Life

dean@deanjackson.com (Dean Jackson) — Fri, 12 Jun 2026 00:00:00 GMT

Up until 1996 I was a practitioner. I used marketing to build my own real estate business, but I wasn't teaching it to anyone yet. Going through journal number one, I can see the moment that started to change.

One of the first times I applied what I knew outside real estate was helping a friend in Ottawa who placed contract programmers. Instead of chasing companies for job openings, we ran an ad that gathered the programmers first, then walked into the telephony companies with the people already in hand.

That's the first principle I keep coming back to. If you help enough other people get what they want, you can get anything you want. It's why finding buyers first makes you valuable to any realtor who needs listings.

This same journal also holds the day I first walked into the Strategic Coach office and picked up Dan Sullivan's How the Best Get Better, before I'd ever met him. It's funny to see where these things start.

Show notes: https://deanjackson.com/podcasts/tol/017-the-1996-marketing-idea-that-changed-my-life/

I haven't made a cold call in 35 years… here's how

dean@deanjackson.com (Dean Jackson) — Fri, 05 Jun 2026 00:00:00 GMT

When I got started in real estate, all I did was make cold calls. People actually answered the phone back then, but I realized fast that it was a hamster wheel. Take me out of it and there was no business left.

Michael Gerber's The E-Myth flipped that for me. I learned to work on the business instead of in it, so I built a lead-getting system. I made a guide to Halton Hills real estate prices that let people learn about the area without driving out to see it, and an old agent's box of floor plans gave me the idea.

That guide, plus a Market Watch newsletter I mailed every two weeks, brought in leads while I did nothing. I licensed the whole system to 40 agents across Toronto and beyond, and that's what led me to Joe Stump and to meeting Eben Pagan.

This is where my life with direct response really began, and it's why I haven't made a cold call since.

Show notes: https://deanjackson.com/podcasts/tol/016-i-havent-made-a-cold-call-in-35-years-heres-how/

I journaled everyday for 30 years & here's what I know so far...

dean@deanjackson.com (Dean Jackson) — Fri, 29 May 2026 00:00:00 GMT

I just turned 60, and to mark it I went back to the Eagle Ridge Mall in Lake Wales where I sat with my very first journal in 1996. I've written in a journal every single day since then, and there are now hundreds of them.

Back in 1996 there was no Google, no YouTube, no Facebook, and Apple was failing. Looking back, I can see my whole life as a series of vector-changing moments, the handful of times something happened and I ended up pointed in a completely new direction.

The biggest one took me off the tennis court. I trained at Rick Macci's academy alongside future champions, but at 22 I realized I didn't want to still be grinding on tour at 30. A story a former player told me on a boat in Vero Beach made me pivot to business, and that's how I ended up back in Florida starting this journaling adventure.

This is the start of a series. I'm opening journal number one and working through all of them, pulling out the insights that still hold true and the opportunities I saw but didn't act on. Hope you'll come along.

Show notes: https://deanjackson.com/podcasts/tol/015-i-journaled-everyday-for-30-years-heres-what-i-know-so-far/

Establishing a BRAND

dean@deanjackson.com (Dean Jackson) — Thu, 04 Mar 2021 00:00:00 GMT

What does it actually mean to establish a brand? As a direct response guy focused on results, I've always felt the tension with the branding camp. Then a Ray Dalio video on the economic engine clicked something for me. A market is just the sum of individual microtransactions, one person trading money with another. A brand works the same way.

So here's my definition: a brand is a buying reflex affecting now decisions. The only time anyone can buy is now. Buying intention and buying history feed into it, but you can't bank those today. Coca-Cola and Budweiser have simply built that reflex in billions of individual minds over time.

That's actually hopeful. The microbrewery in Punxsutawney owns the reflex in its own town, often just through proximity, recency, and a clear message. Figure out the exact moment someone chooses, then make your reflex the one they lean toward.

Show notes: https://deanjackson.com/podcasts/tol/014-establishing-a-brand/

who not how zoom

dean@deanjackson.com (Dean Jackson) — Fri, 30 Oct 2020 00:00:00 GMT

In less than 90 minutes, Joe Polish and I are going live on Zoom with Dan Sullivan and Ben Hardy for their new book Who Not How, so join us at ilovemarketingzoom.com at 1pm Eastern on Friday, October 30th.

Show notes: https://deanjackson.com/podcasts/tol/013-who-not-how-zoom/

Lee Iacocca target market

dean@deanjackson.com (Dean Jackson) — Wed, 03 Jul 2019 00:00:00 GMT

I'm in Amsterdam on our summer world tour, and I just saw Lee Iacocca passed away. It reminded me what a master target marketer he was. He put the Mustang in front of the largest baby boom in history right as the leading edge turned 18 in 1964, exactly the young, sporty, affordable car they wanted. Twenty years later he gave those same people the minivan at 38 and turned Chrysler around.

Demography is an inevitability. If something appeals to a huge group and there are millions more right behind them every year, you've got a hit on your hands.

Look at today. We've got 10,000-plus people turning 60 every day for the next 20 years and a massive transfer of wealth underway, while the youngest millennials are just turning 19. Ask what those groups will inevitably need or want, pick one, and get in front of it.

Show notes: https://deanjackson.com/podcasts/tol/012-lee-iacocca-target-market/

Ideas versus execution

dean@deanjackson.com (Dean Jackson) — Mon, 17 Jun 2019 00:00:00 GMT

I'm in Toronto starting a Breakthrough Blueprint, and over coffee with Ross O'Laughlin we got onto ideas versus execution. I've always defended the value of ideas in a world that fetishizes execution. People say ideas without execution are worthless, which is true, but you can't execute nothing either. They're paired.

Grant that something is being executed flawlessly. The only thing that can improve it is executing a better idea. Ross showed me a campaign humming along at a steady opt-in rate, then he had a brainstorm, executed it with the same precision, and the opt-ins exploded. That's the power of an idea.

As I said in the execution arbitrage episode, execution is becoming the commodity. AI and machines can execute anything. Where we win is coming up with the ideas someone has to program the machine to run. That's our trump card.

Show notes: https://deanjackson.com/podcasts/tol/011-ideas-versus-execution/

Love is pain

dean@deanjackson.com (Dean Jackson) — Mon, 04 Mar 2019 00:00:00 GMT

I'm at dinner in Phoenix with Annie Lala the night before our email workshop, and we got onto how you capture ideas and get them into the world. Annie shared something that stuck with me: to experience love, you have to be willing to experience pain. The heart is a muscle, and the more heartbreak you turn into strength, the more capacity you have to love.

Most people run from that feeling in a relationship, the urge to give up mid-conflict. But those are the last three reps, the ones that hurt most and make the most difference. Stay in, keep talking, and you turn conflict into intimacy.

The conversation itself is the lesson in the other thing we were discussing. We spoke this out loud, recorded it, and in minutes it's a podcast anyone can learn from. Talking is the fastest way to get your best ideas out into the world.

Show notes: https://deanjackson.com/podcasts/tol/010-love-is-pain/

The tyranny of convenience

dean@deanjackson.com (Dean Jackson) — Sun, 24 Feb 2019 00:00:00 GMT

I'm outside a packed Starbucks in Orlando, sitting comfortably in the sun while the line curls around the building, because I ordered and paid from the app. It reminded me of a New York Times piece called The Tyranny of Convenience, which argued convenience is the most powerful and underrated force guiding our decisions.

The easiest way always wins. It's the same reason I record these podcasts by telling Siri to start, then speaking the title and description, and it's on iTunes before my drink is ready.

So look at everything you do and ask how you can make it as convenient as possible for the people you work with. Do that, and watch them come straight to you.

Show notes: https://deanjackson.com/podcasts/tol/009-the-tyranny-of-convenience/

Execution arbitrage

dean@deanjackson.com (Dean Jackson) — Thu, 31 Jan 2019 00:00:00 GMT

I woke up with words for something I've been watching for a while: execution arbitrage. Right now you can get almost anything executed on demand, at scale, which means the idea person who sees how pieces fit together is positioned to win. Kylie Jenner runs a $350 million cosmetics company with seven core people because everyone else, the manufacturing, the e-commerce, the distribution, is outsourced.

You see it everywhere once you look. Airbnb and Uber are just interfaces between people who want an outcome and people with the capacity to deliver it. My own Getting Listings program for real estate agents works the same way, push a button and we handle all the execution.

Execution is becoming the commodity. So look at the outcomes your business is paid for, ask how much of that could be handed to someone else, and get paid for the bundle. That's the arbitrage.

Show notes: https://deanjackson.com/podcasts/tol/008-execution-arbitrage/

Specialized data

dean@deanjackson.com (Dean Jackson) — Mon, 28 Jan 2019 00:00:00 GMT

Over dinner in Miami I got thinking about Richard Viguerie, the father of conservative fundraising and the guy largely credited with getting Reagan elected. In 1962 a new law made large political donors part of the public record, so he took six ladies into the records office and hand-wrote 12,000-plus names and addresses onto index cards.

That list was an asset nobody else had. He rented it out, kept gathering every donor from every campaign, and built an empire on being first in and the only one with that information. What struck me was the willingness to do the hard, unglamorous work almost no one else will do.

We've done our own version of this, hand-correlating the 2,100 lakefront homes in Winter Haven, the homes with mountain views in Paradise Valley, oceanfront condos in other markets. In a world where everyone's using the same algorithmic data, that qualitative information you have to work to gather is a real advantage. Don't be afraid to put in the effort.

Show notes: https://deanjackson.com/podcasts/tol/007-specialized-data/

When is a diet pill worth $153

dean@deanjackson.com (Dean Jackson) — Sun, 20 Jan 2019 00:00:00 GMT

I still think about the Leptoprin infomercial that opened with when is a diet pill worth $153 a bottle. Everyone who'd already tried the $19 and $29 pills and given up perked right up, because finally here was one expensive enough to have the good stuff, and one that told them it was too powerful for vanity dieters.

Then I saw a knockoff, Leptopril, running the pharmaceutical generic play, and dug in. The same company owned all of them. Thyroid ATC for undiagnosed thyroid, Estrin D for menopausal women, each one speaking to a very specific reason someone believes they can't lose weight.

The lesson is about friction. If someone doesn't have that particular frustration, they're blind and deaf to the message, but name the exact thing that's stopping them and they perk up and think that's me. Get specific about why people are delaying, address it directly, and they line up for the help you can give them.

Show notes: https://deanjackson.com/podcasts/tol/005-when-is-a-diet-pill-worth-153/

Working backwards

dean@deanjackson.com (Dean Jackson) — Sun, 20 Jan 2019 00:00:00 GMT

Gamal Aziz ran the MGM Grand, and his approach stuck with me for years. He broke the hotel into all its components, restaurants, entertainment, retail, and for each one asked how high is high, then counted the difference between that and current results as a loss.

They had a profitable $4 million restaurant, but he watched guests leave every night for celebrity restaurants elsewhere. In his mind they were losing $4 million a year, so he tore it out, partnered with Michael Mina, and did $11 million the first year. Same story with entertainment: a $28 million show became a Cirque du Soleil doing $120 million. Even $40 haircuts became $400 stylings.

He called it working backwards, and it's the opposite of chasing a 20% annual improvement. It's instant and radical. Go through your own components, ask how high is high, and treat the gap as money you're actively losing. That framing gets your attention in a way that a comfortable profit never will.

Show notes: https://deanjackson.com/podcasts/tol/006-working-backwards/

What's in a name

dean@deanjackson.com (Dean Jackson) — Fri, 18 Jan 2019 00:00:00 GMT

This one came out of a discussion at the I Love Marketing meetup about naming products, and my view is simple: naming is everything. A name that telegraphs exactly what your product does beats a clever one every time. Dan Kennedy turned Formula 489 into Kills Weeds Dead, and suddenly it's obviously the right product on the shelf.

There's a photographer in London who skipped the generic commercial photographer label and built weshootbottles.com, nothing but beautiful shots of bottles. If you sell a product in a bottle, they head and shoulders beat every generalist. And when they want cans, they just spin up weshootcans.com. Same studio, same lights, new specialist.

Sometimes the product doesn't change at all. Excedrin Migraine and Excedrin Extra Strength are the identical pill, but the Migraine box sells for up to a 30% premium because it names exactly what someone's looking for. Any time you can narrow your focus to the person you most want, that's where the benefit lives.

Show notes: https://deanjackson.com/podcasts/tol/004-what-s-in-a-name/

Live referral field report

dean@deanjackson.com (Dean Jackson) — Fri, 11 Jan 2019 00:00:00 GMT

The day after I recorded the referral episode for Michael Bernoff, he demonstrated the whole thing at lunch without even realizing it. Somebody asked for a restaurant, mentioned they liked sushi, and Michael instantly thought of Sushi Roku, pulled out his phone, and set up the reservation with the double royal treatment himself.

That's the position we want to own in a client's mind. Sushi comes up, one place fires, and he didn't just recommend it, he handled everything so the other person gets treated like an insider. Michael becomes the guy with the guy.

This goes back to how we're wired. Adding value to the tribe raises your status, and we're built to keep the exchange even. So the real work is programming your clients to feel like insiders with your business, and giving them the trigger words so they know exactly when and how to send someone your way. We're not training salespeople, we're training givers.

Show notes: https://deanjackson.com/podcasts/tol/003-live-referral-field-report/

Secret psychology of referrals

dean@deanjackson.com (Dean Jackson) — Thu, 10 Jan 2019 00:00:00 GMT

I was sitting alone at Starbucks watching people talk, and it hit me that this is exactly where referrals happen. Every referral comes out of a conversation, and three things have to fire: they have to notice it's about what I do, think of me, and actually introduce me to the person.

For every call I get, there are probably five more conversations where someone thought of me but never told me about it. So the goal isn't to remind clients to talk about me, it's to instruct them on what to do the moment they hear the right conversation.

That's why we send the world's most interesting postcard every month, with a little post-it note on the back: just a quick note in case you hear someone talking about buying their first home, give me a call and I'll get you a copy of our book to give them. We're presencing the conversation before it happens.

Show notes: https://deanjackson.com/podcasts/tol/002-secret-psychology-of-referrals/

Thinking Out Loud Episode One

dean@deanjackson.com (Dean Jackson) — Wed, 09 Jan 2019 00:00:00 GMT

This is where it all starts, the first episode of Thinking Out Loud, recorded live from Genius Network.

Show notes: https://deanjackson.com/podcasts/tol/001-thinking-out-loud-episode-one/