10-Minute Emails That Make You More Money

From: Olly Richards4th August 2023Hobbitshire: Something big is brewing… Last night, I was on the phone with my business mentor. About 47 minutes into the call, he told me an anecdote about a business he worked with: “Scaling was simple for them… they just started sending daily emails.” I didn’t bat an eyelid at the […]


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How to Make Better Decisions

Do you know what an entrepreneur does? An entrepreneur makes decisions. Lots of them. Think back to your first couple of years in business – you were probably making 50 small decisions a day: Size of the font Price of the contract Opening line of your conference talk This freelancer or that Getting your business […]


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The Case Against Discounting

’ve been writing this newsletter for a little over six months now. It’s fascinating to start something new. One of the amusing things I’ve come to learn: The “marketing hot buttons” that make people mad! Certain opinions I bring up reliably provoke a barrage of emails and tweets. Some of them objecting. Some of them […]


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The Engagement-Based Business Model

From: Olly Richards14th July 2023Hobbitshire: Stranded in a corn field I think the Internet makes people lazy. Doing business is too easy. You can make content for free, run ads easily, spam Twitter, then just throw together an offer and… “Someone’s gonna buy!” But that’s not business. That’s grifting. I think the old school direct […]


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35 Business Lessons From My Mentors

One of the reasons I enjoy flying planes, is that it’s damn humbling to be a beginner again. With flying, there’s a lot of information to learn. And I noticed something interesting about this new information… I only truly “know” a piece of information when I’ve encountered it in multiple different situations. Know what I […]


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3 Steps To Making Better Strategic Decisions

Do you know what this blog is? It’s therapy to myself. Much of the time, when I choose to write about a given topic, it’s because it’s been on my mind, and I want to organise my thoughts. It may seem like I have it all worked out. I don’t. By the time the topic […]


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A Decision Framework For Choosing New Media Properties

From: Olly Richards26th May 2023Hobbitshire: Just discovered a famous founder lives near me! For an online education business, content is the lifeblood. The formula is simple: Teach what you know with free content. Then sell the guided solution. Do this right, people trust you, and selling becomes easy. From $0 to $1M in revenue, you […]


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Money Needs A Plan

From: Olly RichardsHobbitshire: Literally sitting in a castle right now  Entrepreneurs are weird when it comes to money. We great at making it. But once we have it… We’re terrible at knowing what to do with it! One of the reasons this happens: Nobody talks about managing money! So you’re kinda left to figure it […]


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Blueprint Of A $10M Online Education Business

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