How to Make Big Investment Decisions

I was talking with an entrepreneur recently about a familiar dilemma: “Should I hire XYZ agency for a $30k piece of funnel building work?” The questions were: This email is how I think through these kind of large decisions. It might help you make similar assessments. I tend to look at an investment like this […]


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The trapped CEO phenomenon (and how to escape it)

Business is about choices. And whatever is plaguing you in your business right now: And however intense or difficult it may feel… The solution is waiting for you on the other end of a choice. The choice just needs to be seen and made. Now here’s what’s interesting: The bigger the business, the harder your choices feel. […]


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Content addicts design the WORST business models

There seems to be a general assumption that running a solo business means living on the “content hamster wheel”. Sitting up at 2am, bloodshot eyes, trying to churn out just one more reel, because Gary V said you have to publish 25 times a day. But that doesn’t mean it’s the only way. (Unless of […]


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Personal brands that bore my cat to tears

Over the last few years, I’ve watched every man and his dog start an email newsletter. I’ve seen everyone on Twitter label themselves a “storyteller”. (Who knew?) I’ve been creeped out by the same grinning headshots on every LinkedIn profile. Seems everyone wants to start a personal brand. But here’s what I also noticed: Everyone’s […]


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Did somebody say the R-word? (I’m not scared)

People think that recessions cause businesses to fail. And they do. But most businesses fail for other reasons. Here are some examples: You get the idea. We never think it will happen to us… But it’s smart to be thinking ahead. In 12 years of building my business, StoryLearning, I’ve seen a lot of changes. […]


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Why successful biz owners need a personal brand

I have at least 100 entrepreneur friends with 7-figure businesses. And while many of them are happy to stay in the shadows… Behind the scenes… Don’t want their names and faces out there… Just as many of them have got something to say! For example, one top bloke I met a couple of months back […]


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When business is easy

Dear reader, You don’t mind if I take a brief foray into woo-woo territory do you? Bear with me here… Because although you might think I’ve been drinking a little too much of the good stuff, this is a topic that really matters for the right person. The conclusion of this email COULD be that […]


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Why I never go 12 months without THIS

Recently, I was doing some 360º feedback on myself, and I asked my COO at StoryLearning: “What could I do better?” His reply: “Focus on things that excite you. Good things tend to happen when you’re working on things that excite you.” Of course, this is code for: “You’re a giant PITA when you’re not […]


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Why I publish my newsletters on my blog (it’s not for SEO)

A reader asked me a cracking question: “Olly, why do you publish your email newsletters on your blog? They don’t look optimised for SEO at all, so what’s the strategy?” Astute observation. There are four reasons I put (some of) my newsletters on my blog, and none of them are about gaming the Google algorithm. […]


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Blueprint Of A $10M Online Education Business

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