The “multiple avatars” problem (and how to fix it)

If you’ve been in business for a few years, you likely see a number of types of customers inside your business. For example, in my language business, StoryLearning, we have customers learning with wildly different goals: Some for workSome to keep their brains healthySome to speak with their partner in their language To make matters […]


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Why you can’t enjoy your holidays

A few summers ago, I was on a driving holiday in Scotland. Glorious. Driving through the dramatic landscapes of Skye and Inverness… I felt like I was on Route 66 or something. (Not that I’ve never been on Route 66. It just felt a little otherworldly.) Apparently, it rains a lot in Scotland. Not this […]


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Why Course Sales Are Declining

A couple of weeks ago I published a series that caused quite a stir: “How a 7-figure Business Dies” Since then I’ve had a lot of emails from seasoned entrepreneurs with a similar story to tell. “Olly, WTF – you’ve just described my exact situation.” Tldr; (You can find and share the series here) But even […]


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17 tips for writing an intoxicating email newsletter

Somewhere deep in the dusty corridors of an ancient Aweber account… Covered in cobwebs and left to rot… Are some of my very early email newsletters that I wrote to my StoryLearning list. Emails about language learning… written in 2013. I still have those emails, you know. And when I look back at them today, […]


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The real reason I went “all in” on this newsletter

When I started this newsletter in January 2023… It was mostly for fun. I wanted to do something creative again. I had stuff to talk about from 10+ years of running StoryLearning. And I’ll be honest… It was nice for my ego too, to see my personal brand out in the wild, spouting my sagacious […]


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Should I build another product?

Once, I sent an email to my list on “Why being bored can make you millions.” And then a question came in response: What is the rule of thumb for when you stop “adding”?​I have 2 major revenue streams and am thinking of adding a 3rd which would clearly work too. But I also need to optimise the […]


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The business model that millionaires get wrong

Do you want to know the most common way entrepreneurs build out their business models? It’s like this: “I saw XYZ guru talking on Twitter about their new [product]… so I’m going to do that too!” Whatever that product may be… MRR thingy, premium newsletter, $7 tripwire… They just blindly copy it. They assume that […]


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The complexity that’s quietly killing your business

The art of business models involves knowing when to stop building. When to say… That’s it! I’m doing enough stuff in this business now. It’s time to stop adding anything new! Know who suffers most with bloated business models? 7-figure business owners. For years, they add more and more products and services, tacking one thing […]


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How a 7-figure Business Dies

You’ve read stories of how 7-figure businesses are built. But how does a 7-figure business die? In this tale, you’ll see how. And if you pay close attention, you’ll learn lessons that will help you avoid the same fate. After all… There are many different ways to grow. But there are a thousand ways to […]


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Blueprint Of A $10M Online Education Business

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