What’s the ROI of a team retreat?

Greetings from sunny Malta. I’m here for our annual team retreat with my business StoryLearning. It’s the same playbook as ever: It’s hard to underestimate the importance of team gatherings, especially if, like us, you’re fully remote. People sometimes ask how I justify the cost. (Which runs into multiple $10,000s.) And indeed, if the question […]


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Will your business exist in 2 years?

Recently, I ran a webinar on “AI, Google and the Future of Course Businesses”. You know, the one where I had the tech meltdown? 🙂 Anyway… One of the core premises of that webinars was: The future (of education businesses) is going to look VERY different than it has in the last 10 years. The […]


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The measure of the man…

This is not the email I expected to write today. I thought I was going to write “launch email 2” or whatever. Instead, I find myself scrambling to fix things going pear shaped. But rather than run from it… I’m going to confront it head on. . . . So, yesterday, two things happened: Now… […]


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I’d rather have NO business than do THIS!

Let me tell you a tragic tale about my very first welcome sequence. It was 2014, I think. It looked a bit like this: Now, I know what you’re thinking… “Steady on, Olly… you’re in danger of annoying them with all that selling!” But of course, there wasn’t much chance of my annoying anybody ever, with […]


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The dark side of being “good on calls”

I have this friend. Brilliant coach. Clients are queuing up around the block to work with her. She’s completely maxed out. Can’t fit another soul into her calendar. When I asked her about her secret sauce, she shrugged and said: “When I do sales calls, people just love me. They know I can help them […]


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3 types of subscribers (and which ones to ignore)

The fundamental tension for online educators is this: So, how do you navigate this, as someone who cares about your brand and reputation, but still needs to run a business? Here’s how I think about it… I categorise my audience in three different groups, and seek to create a unique experience for each: Firstly… The […]


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I stole this 15-minute Netflix trick for my email marketing

There’s been a murder in the White House. It happens during a state banquet. A world-famous detective is called. No-one’s allowed to leave – presidents, ambassadors, famous stars… they’re all locked in until the murder is solved. Classic whodunnit stuff. Not my invention, unfortunately. It’s a new Netflix show called “The Resident.” Fast-paced. Gripping. But […]


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Are you a pillow kisser or a business owner? (How to tell)

Question: How do you know when an online business has “grown up”? Answer: When their ideal customer lands on their website and says: “Holy s*** — this was made for me!” Like these emails that Uncle Olly receives regularly: When you can get reactions like this, selling your stuff is easy and effortless. But getting […]


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Blueprint Of A $10M Online Education Business

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