The Ashcroft Files

Introduction from Rob: I first stumbled into Michael Ashcroft's online universe in the early months of 2021, and was immediately captivated by his writing.

Since then, I've hired him as a coach, consulted with him on his business, and we've become internet homies. He's genuinely one of the most intelligent, kind, curious people I know.

Michael's also the archetype for a new type of creator. In 2021, he created a course on Alexander Technique, which despite being an esoteric topic, has brought in just shy of $100K in ten months. But here's the crazy part. He did this as a first time entrepreneur, while ignoring 95% of the "best practices" in the online marketing world. No funnels. No elaborate launches. No hype. None of it.

But the more I've talked to Michael, the more I've realized this wasn't luck or a fluke. The guy is masterful at fostering trust, and his early success reflects many of the new strategies I've been exploring around friendly, generous, playful, non-coercive marketing.

In that vein, Michael's agreed to document his indie business journey on Ungated. I don't know where this case study is headed, but I'm sure it'll be full of genuine insight into how to build a business that reflects your values, and slots perfectly into the life you're creating for yourself.

Think of this page as a dynamic "map of content" of sorts. It will point towards a bunch of other pieces of content—some on Ungated, some on Michael's site or YouTube channel—that each tell a small part of the story. And whenever Michael has something new to share, he'll weave it onto this page. So check back often.

And with that, it's time to hand the baton off to Michael.

Thanks for the kind words, Rob! And hello, new reader. It's nice to make your acquaintance.

My back story

I've been a free agent since February 2021, when I left behind a ten year career in low carbon energy innovation. I worked for such companies as National Grid and KPMG here in the UK helping to bring about a secure, sustainable energy system. That was my thing.

And it was all going well until I burnt out. You see, the traditional employment structure was never a good fit for me; it always felt like I was swimming upstream. I never enjoyed being assigned projects and tasks, most days felt like they were harder than they needed to be, and I had a sense that I had a bunch of skills that I just wasn't able to use in that environment. I was a generalist stuck in the life of a specialist.

And then, one day, after a particularly intense few months at work and in my personal life, I woke up to discover that I couldn't keep going. Something had to change.

This might be the most vulnerable thing I've ever published.

I had always known I wanted to be some kind of free agent, but I didn't know what I could do besides the follow the conventional path, so I ended up staying on that path until life conspired to tell me, in no uncertain terms, to get the hell off it.

So that's what I did.

How I got to where I am now

Today I find myself in an extraordinarily different position, a place I've long dreamed of, but never believed could be possible for me.

The main thing I'm known for right now is as a teacher of a somewhat obscure practice called the Alexander Technique. If you want to know more about that then here's the entry point to that particular oasis, but I won't talk about the content of that in this case study.

I've always been someone who played around at the edges around work. I was a freelance journalist for a while, a freelance consultant, and from 2014 — 2017 I trained in evenings and weekends as an Alexander Technique teacher.

I strongly believe that Alexander Technique has a lot to offer the world. It's traditionally taught in person via touch and has become associated with posture, movement and performance. It's most often practiced by performers like musicians, actors and athletes.

I want to change that. My training was unconventional, so to me Alexander Technique looks way more like a mindfulness practice and that's how I teach it. My vision is to figure out these things:

how to talk about it in a way that vastly more people want to learn it
how to teach it asynchronously online to make it more accessible and scalable
what Alexander Technique really is at its core and how it intersects with mindfulness practices, movement practices, human anatomy, neuroscience, philosophy and the future of humanity. Yes, really.

And yes, I do plan to write a detailed post, which will go here, on how I managed to create a $100k+ revenue course by taking an in-person practice online.

Designing games I actually want to play

Anyway, enough about Alexander Technique. This collaboration with Rob is about how I'm doing what I'm doing, not what it's about.

My experience with the ill-fitting job frame has taught me to reconsider what success means. Before it was income, seniority and a vague sense of 'impact'. Now I am optimising for fun and the freedom to pursue things that matter to me and in the ways that align with my values.

This has led to a few insights, which I'll share here.

First of all, I want everything I do to be playful.

This is the real secret of life — to be completely engaged with what you are doing in the here and now. And instead of calling it work, realize it is play.” — Alan Watts

There's a lot I can say about play, and you can read about it below, but the point is that I can make choices to bring about a sense of ease and play in everything I do. If something feels not playful, I can change things until it does. That applies as much to my business as it does to the rest of my life.

This mindset guides my choices in everything I do: product design, marketing, general 'vibe', etc. There's much talk out there about venture-backed businesses vs lifestyle businesses, but not much about structuring a lifestyle business based around different kinds of desired lifestyles. I want my business to enable a lifestyle that I want to have. I've written about how I'm thinking about this here.

I want to give a concrete example of what this looks like in practice.

I originally sold my course through a series of launches, because I didn't want to be in selling and marketing mode all the time. This worked amazingly well and I would do it again to generate interest at first, but it stopped working for me a few weeks ago.

I found myself in a position where I did a launch, it did far better than I expected (I made $37k) and then I almost felt too comfortable. Having a big chunk of cash coming in didn't motivate me to keep doing regular, incremental work on the course.

So I decided to make it generally available for sale, knowing that if I stopped talking about it then potential customers would stop seeing it and it would stop selling. And in order to be able to keep talking about it, I would need to keep thinking about it.

That's another of the principles I'm following: to design my business so that it encourages me to behave in certain ways, rather than having to behave in certain ways to make the business work.

Things I'm working on

Right now there are two things on my mind with regard to my business.

Launch Playful Creativity

I'm working on a new email based course that will help people reduce various kinds of self-interference that get in the way of play. I'll be pre-selling it to my existing students for $50 by 28 October 2021 and will then build an MVP to share by the end of November 2021.

Update on 15 January 2022: Well, it's embarrassing to admit, but I got myself into a creative rut while trying to make Playful Creativity. You can read about that, and how I'm dealing with it, here:

Create a distributed, self-organising student community

I have done a lot of cohort-based courses and have been a mentor for two of them (Write of Passage and the Part-Time YouTuber Academy). They're great, but they're also very expensive and require a lot of work as the creator.

My course is self-paced, because that fits the lifestyle I want, but I want to do more to help my students create something of a cohort vibe, if they want. There's something around facilitating small groups to get together and go through the course materials in their own time.

This should help make courses more accessible in terms of price, provide a lot of the benefits that cohort-based courses provide, while also keeping my headspace free for other things. I don't yet know how to do this, but I'm excited to find out.