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Explore every episode of the podcast Thinking Out Loud with Dean Jackson
Dive into the complete episode list for Thinking Out Loud with Dean Jackson. Each episode is cataloged with detailed descriptions, making it easy to find and explore specific topics. Keep track of all episodes from your favorite podcast and never miss a moment of insightful content.
| Title | Pub. Date | Duration | |
|---|---|---|---|
| The Secret to Writing So People Respond | 27 Sep 2026 | 00:14:18 | |
Every effort to sell creates resistance. Write like you're talking to one person, offer a real service instead of a pitch, and people respond.
Show notes: https://deanjackson.com/podcasts/tol/116-the-secret-to-writing-so-people-respond/ | |||
| Before You Offer a Discount, Try This Instead | 26 Sep 2026 | 00:09:40 | |
A discount tells people your price was never real. Paying for their first result keeps your price intact and turns one try into a long-term customer.
Show notes: https://deanjackson.com/podcasts/tol/115-before-you-offer-a-discount/ | |||
| How to Make It Ridiculously Easy for People to Say Yes | 25 Sep 2026 | 00:09:14 | |
Ask someone to take a chance on you and you get resistance. Offer to take a chance on them and the way is easy. Here's how I built a rocket ship on that.
Show notes: https://deanjackson.com/podcasts/tol/114-how-to-make-it-ridiculously-easy-for-people-to-say-yes/ | |||
| How to Make Your Marketing Feel Like a One-on-One Conversation | 24 Sep 2026 | 00:11:14 | |
Claude Hopkins taught me every purchase is made by one person. So stop broadcasting to the mass. Here's how I turn an opt-in into a one-on-one conversation.
Show notes: https://deanjackson.com/podcasts/tol/113-how-to-make-your-marketing-feel-like-a-one-on-one-conversation/ | |||
| Proving is More Convincing Than Convincing | 23 Sep 2026 | 00:09:43 | |
A line from Claude Hopkins in 1927 changed how I sell. Stop convincing people. Just give them the result first, and they convince themselves.
Show notes: https://deanjackson.com/podcasts/tol/112-proving-is-more-convincing-than-convincing/ | |||
| Before You Spend Thousands on Marketing, Run This $100 Test | 22 Sep 2026 | 00:14:27 | |
A book from 1927 taught me to never spend big until a $100 test tells me I've got a winner. Here's the four-stage clinical trial I still run today.
Show notes: https://deanjackson.com/podcasts/tol/111-before-you-spend-thousands-on-marketing-run-this-100-test/ | |||
| The Internet Changed Everything… Except Why People Actually Buy | 21 Sep 2026 | 00:11:00 | |
An ad I ran in 1996. Free government money, a recorded message, a mailed book. Zero internet... and the exact same psychology still works today.
Show notes: https://deanjackson.com/podcasts/tol/110-the-internet-changed-everything-except-why-people-actually-buy/ | |||
| The Real Money Is in the Relationship, Not the Transaction | 20 Sep 2026 | 00:09:34 | |
Journal seven, 1997. Only 5% of the town buys a house this year. But everyone owns one all year long... and that relationship is the real money.
Show notes: https://deanjackson.com/podcasts/tol/109-the-real-money-is-in-the-relationship-not-the-transaction/ | |||
| Old Marketing Tools Still Work Just Fine | 19 Sep 2026 | 00:16:17 | |
Journal seven, 1997. I made a list of every tool I knew how to use... and thirty years later almost every one of them still works just fine.
Show notes: https://deanjackson.com/podcasts/tol/108-old-marketing-tools-still-work-just-fine/ | |||
| If You're Going to Run an Ad in the Next 6 Months, Watch This | 18 Sep 2026 | 00:10:42 | |
That headline you clicked on? It's the same formula I found in journal seven back in 1997. A directive, an open loop, and exactly the right people leaning in.
Show notes: https://deanjackson.com/podcasts/tol/107-if-youre-going-to-run-an-ad-in-the-next-6-months-watch-this/ | |||
| "The Secret To Life Is One Thing..." [Evidence Inside] | 17 Sep 2026 | 00:13:34 | |
Dinner with Jim Morton, back in journal seven. He built an empire on one thing... and City Slickers had the answer all along.
Show notes: https://deanjackson.com/podcasts/tol/106-the-secret-to-life-is-one-thing-evidence-inside/ | |||
| Copy This Plug & Play System To Sell More Of Almost Anything Quickly! | 16 Sep 2026 | 00:10:33 | |
I found the Porsche 911 dealer in journal seven. All he did was sell one car to one person. Here's the playbook you can plug into almost anything.
Show notes: https://deanjackson.com/podcasts/tol/105-copy-this-plug-play-system-to-sell-more-of-almost-anything-quickly/ | |||
| Why Trying Harder Isn't The Answer | 15 Sep 2026 | 00:08:19 | |
I found a little book in my 1997 journal called You Squared. A fly trying to escape through a glass window. Ten steps away, the door is open.
Show notes: https://deanjackson.com/podcasts/tol/104-why-trying-harder-isnt-the-answer/ | |||
| Why I Plan My Future Around What Will Never Change | 14 Sep 2026 | 00:06:52 | |
I'm at Celebration this morning, the town Walt Disney envisioned 25 years before it existed. Build your future on what will never change.
Show notes: https://deanjackson.com/podcasts/tol/103-why-i-plan-my-future-around-what-will-never-change/ | |||
| If We’re Living in a Simulation… This Is the Playbook | 13 Sep 2026 | 00:09:17 | |
Mid-1997 I filled thirty pages with affirmations of the life I wanted. Thirty years later almost all of it came true. Write down the simulation you want.
Show notes: https://deanjackson.com/podcasts/tol/102-if-were-living-in-a-simulation-this-is-the-playbook/ | |||
| How I Funnel Hacked "The Greatest Show On Earth" | 12 Sep 2026 | 00:12:34 | |
I wrote a parable about the circus in 1997. Seven marketing lessons from the greatest show on earth, starting with a free parade at eleven every day.
Show notes: https://deanjackson.com/podcasts/tol/101-how-i-funnel-hacked-the-greatest-show-on-earth/ | |||
| How to Get Your Buyers to Call You Instead of Chasing Them | 11 Sep 2026 | 00:16:09 | |
Generating leads is easy leverage. The work is the detective pass that sorts who's really moving, and a follow-up list you never take anyone off.
Show notes: https://deanjackson.com/podcasts/tol/100-how-to-get-your-buyers-to-call-you-instead-of-chasing-them/ | |||
| Google Reviews Are Killing Your Business… Try This Instead. | 10 Sep 2026 | 00:09:15 | |
A five star review just sits there. A testimonial built as your customer's own story reaches the next person living that exact situation, and moves them.
Show notes: https://deanjackson.com/podcasts/tol/099-google-reviews-are-killing-your-business-try-this-instead/ | |||
| What Would You Do If You Could Count on You To Do It? | 09 Sep 2026 | 00:12:02 | |
My cousin Steven worked twelve hours a week after school, and it left me doing only what only I could do. So what would you do if you could count on you?
Show notes: https://deanjackson.com/podcasts/tol/098-what-would-you-do-if-you-could-count-on-you-to-do-it/ | |||
| How I Gamify My Day For Structure & Freedom As An ADHD Entrepreneur | 08 Sep 2026 | 00:12:35 | |
Ned Hallowell told me to run my days like a bobsled run. Too constraining. So I turned mine into a freestyle slalom instead... and just ski the gates.
Show notes: https://deanjackson.com/podcasts/tol/097-how-i-gamify-my-day-for-structure-freedom-as-an-adhd-entrepreneur/ | |||
| How To Plan & Optimize For Daily Joy! | 07 Sep 2026 | 00:09:00 | |
A page from journal number six, 1997: a list of everything that brings me joy. Thirty years on, most of it still does. Make one and you get the joy twice.
Show notes: https://deanjackson.com/podcasts/tol/096-how-to-plan-optimize-for-daily-joy/ | |||
| Getting Referrals: The Secret Psychology of Why People Refer | 06 Sep 2026 | 00:19:59 | |
Profit Activator 8, and the finale. Nobody refers as a favor. They refer to be the hero of their own tribe. So stop asking people to talk about you.
Show notes: https://deanjackson.com/podcasts/tol/095-getting-referrals-the-secret-psychology-of-why-people-refer/ | |||
| What Would Your Best Customers Buy If You Were Smart Enough to Offer It | 05 Sep 2026 | 00:10:58 | |
Profit Activators 6 and 7. If a law said you could only sell to people who've already bought from you, what would you build for them? Then go and ask them.
Show notes: https://deanjackson.com/podcasts/tol/094-what-would-your-best-customers-buy-if-you-were-smart-enough-to-offer-it/ | |||
| How To Multiply the Value of Every First-Time Customer | 04 Sep 2026 | 00:13:36 | |
Profit Activator 5, part two. Your During Unit isn't one transaction. Add a birthday club and a wine pairing, and the same hundred guests are worth more.
Show notes: https://deanjackson.com/podcasts/tol/093-how-to-multiply-the-value-of-every-first-time-customer/ | |||
| How To Create Super Happy Customers | 03 Sep 2026 | 00:15:15 | |
Profit Activator 5. Storyboard the whole experience benchmark by benchmark, then ask two questions at each one. Where's the wow, and where's the friction?
Show notes: https://deanjackson.com/podcasts/tol/092-how-to-create-super-happy-customers/ | |||
| How To Make Your Offer Irresistible | 02 Sep 2026 | 00:09:58 | |
Profit Activator 4, part one. Risk reduction still leaves them holding it. Reverse the risk instead, and send the horse home for thirty days.
Show notes: https://deanjackson.com/podcasts/tol/091-how-to-make-your-offer-irresistible/ | |||
| The Amazing 9-Word Email That Revives Dead Leads | 01 Sep 2026 | 00:14:19 | |
Profit Activator 3, part four. Nine words to everybody who inquired and never went ahead. Ask if they're still looking, then don't add a single thing.
Show notes: https://deanjackson.com/podcasts/tol/090-the-amazing-9-word-email-that-revives-dead-leads/ | |||
| Convert More Leads: What To Say To Prospects So They All Convert Themselves | 31 Aug 2026 | 00:13:02 | |
Profit Activator 3, part three. Nobody helps themselves to your fridge. Offer the cookies you already baked, and people take the next step themselves.
Show notes: https://deanjackson.com/podcasts/tol/089-convert-more-leads-what-to-say-to-prospects-so-they-all-convert-themselves/ | |||
| How To Know Which Leads Are Actually Going To Buy | 30 Aug 2026 | 00:14:10 | |
Profit Activator 3, part two. You can't tell who'll buy from a name and an email, so the first hundred hours has one job: find the five-star prospects.
Show notes: https://deanjackson.com/podcasts/tol/088-how-to-know-which-leads-are-actually-going-to-buy/ | |||
| 100 Leads Are Worth More Than You Think. Here’s the Math. | 29 Aug 2026 | 00:17:37 | |
Profit Activator 3. Only 15% of the people who buy do it in the first 90 days, so 85% of what your hundred leads are worth hasn't happened yet.
Show notes: https://deanjackson.com/podcasts/tol/087-100-leads-are-worth-more-than-you-think-heres-the-math/ | |||
| How To Find a $1B Honey Hole of Your Best Future Customers | 28 Aug 2026 | 00:16:04 | |
Profit Activator 2, the visible half. When you can list your prospects, don't shine the light on yourself or on them. Shine it over their shoulder.
Show notes: https://deanjackson.com/podcasts/tol/086-how-to-find-a-1b-honey-hole-of-your-best-future-customers/ | |||
| Get More Leads: How To Choose The Words That Get You All The Leads You Need | 27 Aug 2026 | 00:15:18 | |
Profit Activator 2. Compelling isn't convincing. All you're doing is getting exactly the right person to raise their hand at the earliest possible moment.
Show notes: https://deanjackson.com/podcasts/tol/085-get-more-leads-how-to-choose-the-words-that-get-you-all-the-leads-you-need/ | |||
| Why You Make More Money When You Stop Trying to Sell to Everyone | 26 Aug 2026 | 00:15:53 | |
Day one of the eight Profit Activators. Selecting a single target market isn't about who you include. It's about deliberately leaving almost everybody out.
Show notes: https://deanjackson.com/podcasts/tol/084-why-you-make-more-money-when-you-stop-trying-to-sell-to-everyone/ | |||
| How to Know When You Have a $1,000,000 Idea | 25 Aug 2026 | 00:11:21 | |
There are at least ten million dollar ideas in these journals. Here's the test that tells you early whether the one you're holding is one of them.
Show notes: https://deanjackson.com/podcasts/tol/083-how-to-know-when-you-have-a-1-000-000-idea/ | |||
| If You Have Great Ideas But Struggle to Execute Them, Watch This | 24 Aug 2026 | 00:08:39 | |
The coastal condo guides were fully formed in my journal in 1997. What stopped them wasn't the idea. It was that somebody else had to do the work.
Show notes: https://deanjackson.com/podcasts/tol/082-if-you-have-great-ideas-but-struggle-to-execute-them-watch-this/ | |||
| How to Stay in Front of Your Customers Without Spending More Money | 23 Aug 2026 | 00:08:06 | |
In 1997 staying in front of the people who raised their hand meant mailing them every two weeks. Now it's free, it's infinite, and they can reply.
Show notes: https://deanjackson.com/podcasts/tol/081-how-to-stay-in-front-of-your-customers-without-spending-more-money/ | |||
| These Old School Marketing Plays Actually Work Better Today | 22 Aug 2026 | 00:10:57 | |
In 1997 a lead generation business card cost five cents and landed at random. A static Meta ad costs less and lands on exactly the people you choose.
Show notes: https://deanjackson.com/podcasts/tol/080-these-old-school-marketing-plays-actually-work-better-today/ | |||
| News Flash: People Are Lazy. Here’s How to Build Your Business Around It. | 21 Aug 2026 | 00:11:07 | |
In 1997 Jerry Ballinger told me people don't do what they could do. The fix isn't better instructions... it's building for what they will actually do.
Show notes: https://deanjackson.com/podcasts/tol/079-news-flash-people-are-lazy-heres-how-to-build-your-business-around-it/ | |||
| How to Actually Finish the Ideas You Start | 20 Aug 2026 | 00:12:04 | |
A magazine spotted in an airport lounge became a finished, printed kit for By Referral Only members. One idea, carried all the way to something you can hold.
Show notes: https://deanjackson.com/podcasts/tol/078-how-to-actually-finish-the-ideas-you-start/ | |||
| How to Find Clarity on What Matters When EVERYTHING Feels Urgent (In 5 Minutes) | 19 Aug 2026 | 00:11:42 | |
When everything feels urgent, ask what's real in the next 100 hours... then the next 100 minutes. A five-minute journal exercise from 1997.
Show notes: https://deanjackson.com/podcasts/tol/077-how-to-find-clarity-on-what-matters-when-everything-feels-urgent-in-5-minutes/ | |||
| How To Get The Most People to Buy Now AND Later | 18 Aug 2026 | 00:10:03 | |
Most people who see your ad are interested but not ready, and a buy-now-only offer gives them nothing to say. Jeffrey Lant's egregious error number 13.
Show notes: https://deanjackson.com/podcasts/tol/076-how-to-get-the-most-people-to-buy-now-and-later/ | |||
| How to Show Up Right When People Are Ready to Buy | 17 Aug 2026 | 00:10:10 | |
Eight tiny yellow postcards, mailed weekly into one neighborhood ahead of the fall listing wave, took Julie from zero to five of the next 25 listings.
Show notes: https://deanjackson.com/podcasts/tol/075-how-to-show-up-right-when-people-are-ready-to-buy/ | |||
| How to Use the "6 Weapons of Influence" to Sell Anything Fast | 16 Aug 2026 | 00:14:11 | |
A 1997 journal page that turned Cialdini's six weapons of influence into a worksheet, and the ad for six Muskoka lots that fired all six at once.
Show notes: https://deanjackson.com/podcasts/tol/074-how-to-use-the-6-weapons-of-influence-to-sell-anything-fast/ | |||
| How Taking Action On Your Intuition Actually Pays Off | 15 Aug 2026 | 00:09:54 | |
A page in Dean's 1997 journal, one phone call to the local cable company, and the $500 TV show that meant he never lost a listing on the nights it aired.
Show notes: https://deanjackson.com/podcasts/tol/073-how-taking-action-on-your-intuition-actually-pays-off/ | |||
| How One Idea Turned a $4M/yr Restaurant Into $11M/yr | 14 Aug 2026 | 00:06:55 | |
Gamal Aziz looked at a perfectly good $4 million restaurant in the MGM Grand and asked how high is high. The answer took it to $11 million a year.
Show notes: https://deanjackson.com/podcasts/tol/072-how-one-idea-turned-a-4m-yr-restaurant-into-11m-yr/ | |||
| How to Get New Customers in Any Market in 45 Days | 13 Aug 2026 | 00:12:31 | |
The 1997 Dan Kennedy keynote that laid out the right message, the right market and the right media, plus the three-step campaign Dean built from it.
Show notes: https://deanjackson.com/podcasts/tol/071-how-to-get-new-customers-in-any-market-in-45-days/ | |||
| How To Use Constraints as a Multiplier | 12 Aug 2026 | 00:15:43 | |
Ten rules from a 1997 journal page for who Dean would take on as a client, and why constraints on who you work with are a multiplier, not a limiter.
Show notes: https://deanjackson.com/podcasts/tol/070-how-to-use-constraints-as-a-multiplier/ | |||
| How to Write Headlines That Attract Your Very Best Prospects [Samples Inside] | 11 Aug 2026 | 00:12:55 | |
A bus bench that proves itself, a billboard behind trees, and the headline formulas from a 1997 journal page that Dean still uses to this day.
Show notes: https://deanjackson.com/podcasts/tol/069-how-to-write-headlines-that-attract-your-very-best-prospects-samples-inside/ | |||
| How To Say What You Do So Clearly It Sells Itself | 10 Aug 2026 | 00:10:21 | |
Russell Oliver built a Toronto empire on four words. Stop Your Divorce did it in three. Here's how to find the three or four that say what you do.
Show notes: https://deanjackson.com/podcasts/tol/068-how-to-say-what-you-do-so-clearly-it-sells-itself/ | |||
| How to Figure Out Why People Actually Buy Your Stuff | 09 Aug 2026 | 00:14:25 | |
A 1997 journal page, a book about arguing like an attorney, and the six questions that get you inside your prospect's head before you write a word.
Show notes: https://deanjackson.com/podcasts/tol/067-how-to-figure-out-why-people-actually-buy-your-stuff/ | |||
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