I’m 39. Here are 16 lessons from 11 years in online business that I...
Tim Denning@Tim_Denning
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Aug 18, 2025
~4 min read
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I’m 39.
Here are 16 lessons from 11 years in online business that I wish I knew at 25:
Here are 16 lessons from 11 years in online business that I wish I knew at 25:
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1. Find a way to use ethical scarcity & urgency
(Or die trying)
Always open offers rarely sell. They're almost as bad as nice-to-have offers.
Create a start & end time and limit how many people can buy.
If you're selling high ticket this is easy to justify.
(Or die trying)
Always open offers rarely sell. They're almost as bad as nice-to-have offers.
Create a start & end time and limit how many people can buy.
If you're selling high ticket this is easy to justify.
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2. Be absolutely relentless
Business is simple but not easy. Most people give up too soon. Or they don't put in enough effort.
At the start it makes sense to work long hours on your business and obsess over details.
Business is simple but not easy. Most people give up too soon. Or they don't put in enough effort.
At the start it makes sense to work long hours on your business and obsess over details.
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3. Follow up like a psychopath
People are busy. They forget things. They handle the most urgent stuff first.
The people who win do 3x as many follow-ups. I'd recommend at least 5 follow-ups for every ask.
People are busy. They forget things. They handle the most urgent stuff first.
The people who win do 3x as many follow-ups. I'd recommend at least 5 follow-ups for every ask.
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4. Figure out what makes people buy
• Run surveys
• Do 1:1 sales calls
• Host webinars
You need to talk to the market or you end up being a delusional wannabe.
• Run surveys
• Do 1:1 sales calls
• Host webinars
You need to talk to the market or you end up being a delusional wannabe.
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5. Develop a killer mindset
Psychology drives a business more than a product/service, features or ROI.
If you think like sh*t it's impossible to be an owner. Most people have a scarcity mindset.
That'll never work online.
Psychology drives a business more than a product/service, features or ROI.
If you think like sh*t it's impossible to be an owner. Most people have a scarcity mindset.
That'll never work online.
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Get comfortable with:
• Calculated risks
• Many failures
• Daily rejection
• Backing yourself
• Deep uncertainty
• Trolls/haters/critics
• Feelings of bankruptcy
• Calculated risks
• Many failures
• Daily rejection
• Backing yourself
• Deep uncertainty
• Trolls/haters/critics
• Feelings of bankruptcy
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6. Make your why strong enough
Building a business for money isn't enough. The best 'why' is to build a business so you have:
• More freedom
• More time with family
Building a business for money isn't enough. The best 'why' is to build a business so you have:
• More freedom
• More time with family
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7. It's never too late to build a business
I got serious in my early 30s.
Start today.
Start without a plan.
Start before you're ready.
Start without knowing what to sell.
Start while working a job.
Just start. I've seen 80 year olds do it. Why not you?
I got serious in my early 30s.
Start today.
Start without a plan.
Start before you're ready.
Start without knowing what to sell.
Start while working a job.
Just start. I've seen 80 year olds do it. Why not you?
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8. Be prepared to lose money
Gurus tell you to never lose money. But you learn nothing that way.
The best lessons cost money & give you enormous pain.
I had $1.2M stolen from my digital wallet. Taught me more than a 4 year Harvard degree
Gurus tell you to never lose money. But you learn nothing that way.
The best lessons cost money & give you enormous pain.
I had $1.2M stolen from my digital wallet. Taught me more than a 4 year Harvard degree
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9. College degrees teach you to get a job, not run a business
Forget degrees. Go run an online business & you'll learn while doing it.
Forget degrees. Go run an online business & you'll learn while doing it.
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10. Build your business in public
• Acts as a lead magnet
• Gives you endless content
• Helps you attract mentors/partners
• And it's bloody fun, man.
Document your entire business online with social media.
• Acts as a lead magnet
• Gives you endless content
• Helps you attract mentors/partners
• And it's bloody fun, man.
Document your entire business online with social media.
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11. Focus on profit margins instead of revenue
That's why digital businesses sh*t all over traditional ones.
There are close to no expenses with a digital business. It's pure profit + infinitely scalable.
That's why digital businesses sh*t all over traditional ones.
There are close to no expenses with a digital business. It's pure profit + infinitely scalable.
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12. Start with a high ticket offer
• The money will change how you think.
• You can do it with a handful of clients.
• And once your income is sorted you can go bigger and build leverage.
Gurus telling you to sell $20 digital products are dumb
• The money will change how you think.
• You can do it with a handful of clients.
• And once your income is sorted you can go bigger and build leverage.
Gurus telling you to sell $20 digital products are dumb
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13. Focus on ensuring people see your content 10x more than you think feels normal
The average person buys after 30+ emails, not one post they saw of yours on social media.
More content. More email. More nurturing. More offers. More launches.
The average person buys after 30+ emails, not one post they saw of yours on social media.
More content. More email. More nurturing. More offers. More launches.
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14. Sell something you enjoy
Trendy offers that supposedly make big money are the worst.
You might be able to launch one but you won't be able to write about + deliver it for 5 years.
So it'll never become a sizeable business.
Trendy offers that supposedly make big money are the worst.
You might be able to launch one but you won't be able to write about + deliver it for 5 years.
So it'll never become a sizeable business.
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15. Trade passion for obsession
Passion is weak. Obsession takes over your entire life.
Businesses built around obsessions become:
• Red Bull
• UFC
• Nike
• Ferrero Rocher
Everything else gets forgotten.
Passion is weak. Obsession takes over your entire life.
Businesses built around obsessions become:
• Red Bull
• UFC
• Nike
• Ferrero Rocher
Everything else gets forgotten.
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16. Make your writing habit an addiction
Writing is the key marketing for your business. Your ideas are what attract people to you.
So you want to write a lot.
When done right, it turns into a drug addiction.
Writing is the key marketing for your business. Your ideas are what attract people to you.
So you want to write a lot.
When done right, it turns into a drug addiction.
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Writing online becomes:
• Youtube scripts
• Offer docs
• Newsletters
• Sales emails
• 10,000 word essays
• Short form tweets/notes
• Podcast episodes
If you don't master writing online, you won't build a digital business.
• Youtube scripts
• Offer docs
• Newsletters
• Sales emails
• 10,000 word essays
• Short form tweets/notes
• Podcast episodes
If you don't master writing online, you won't build a digital business.
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17. Find a way to leverage AI
Most people are ignoring it. Or are moving too slow. The time is now to implement it.
Best way to start: launch a custom GPT
Most people are ignoring it. Or are moving too slow. The time is now to implement it.
Best way to start: launch a custom GPT
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The last 7 months of my life have been a total wild ride. Basically tore down my digital business, then rebuilt it from scratch for triple the profit.
Read about it here: timdenning.com/500k-v2-xc/
Read about it here: timdenning.com/500k-v2-xc/