Insights: What I've Learned Running My Company All Conditions Media - Redux
Updated lessons from 20 years running my own business.
I have my 250th episode of Looking Sideways coming up! And I’m also very close to hitting a rather large Substack subscriber milestone, which itself feels like a nicely significant moment.
I’m celebrating these numbers because they’re the result of me turning up for this thing week in, week out, for eight years now. And it’s been (*clears throat*) quite a journey, if I do say so myself.

Back in 2017, when I started Looking Sideways, I really was just looking for a creative outlet for my own gobby-minded opinions and story ideas. One where I didn’t have to pitch, and could basically cover what I like.
Would it find an audience? I really wasn’t sure. (And to be honest, I didn’t really care).
But I was pretty convinced that the existing action sports/outdoor media landscape was a moribund, underachieving hinterland of lowest common denominator clickbait and shoddy brand-led storytelling and product placement. (I still kinda think that, to be honest).
Surely there were other people out there who’d appreciate a slightly more cerebral, nuanced, and none-advertising led take on the activities that have filled my life with such evolving joy over the years?
All of which is why, in the early days, as Looking Sideways (whisper it) seemed to take off, it was a total joy to realise that there definitely WAS an audience for my particular take on ‘action sports and other related-endeavours’.
And this loyal Looking Sideways community, who’ve supported me since day one, has undoubtedly been the best part about the whole experience. Especially as they’ve followed along as I’ve made what must, at times, have seemed some pretty confounding editorial and creative choices. (Let’s face it, The Bombhole this increasingly ain’t).
Of course, there have been moments when I’ve been tempted to stick to the original formula, and just … keep on doing interviews with well-known action sporty figures.
Those episodes are still the most popular, and doubtless always will be. I still get messages from slightly confused ex-listeners saying things like ‘Can’t you go back to doing stuff like the Jamie Thomas interview? I WAY preferred that’ (And yes, my upcoming episode 250 guest will fall into this category).
But I’ve always been bloody-minded about this whole thing. Since the start, it has been about doing what I found interesting, rather following trends in the hope that it’d being me a bigger audience.
Why? Because I’ve always thought that honesty and integrity were kinda the point when it comes to creative expression.
That, and trying to express thoughts and ideas that are honest and have something to say, however unfashionable, or against the orthodoxy. It’s why I released The Announcement, for example, and why I’ve always been a sucker for this line by Descartes:
“Whatever I perceive clearly and distinctly is true”.
So whether you’ve been following along since the beginning, quietly cancelled your paid subscription after I went down a rabbit hole too far (hello!), or have found me through Substack in the last few years and are wondering what on earth this thing even is: thank you for the support. And for confirming my hunch, however tangentially, that there’s an audience out there for an ad-free, algorithm-free take on our little corner of the world.
Anyway, to mark the big 250, I thought it’d be fun to revisit some favourite articles and podcast episodes from the last eight years of Looking Sideways: starting with this blog about the things I’ve learned while running my company All Conditions Media, which I first published four years ago.
Much has changed in the intervening years, both in the real world, and in ACM/Looking Sideways land. It was kinda fascinating to read this piece back, and ask myself what I’d change.
The answer, in the end, was: not much. Something else that I’ve learned from my years at the helm of Looking Sideways is the essential truth of this timeless zinger from Andre Gide:
“Everything that needs to be said has already been said. But since nobody was listening, everything must be said again”.
And re-reading this, it is quite amazing to me how frequently we still have these same conversations at ACM, and how often I/we need to relearn these same lessons.
Of course, I’ve given it a little edit and changed up some of the pics. But on the whole, I stand by it.
Have a read and let me know what you think.
1. Your business model must constantly evolve
As LP Hartley put it in one of the most famous openers in literature:
“The past is a foreign country: they do things differently there”.
To prove the point, here’s a short list of things that didn’t exist when we founded All Conditions Media back in 2005: AI. Instagram. WhatsApp. iPhones. Uber. ‘Creators’. ‘Influencers’. People using nonsensical phrases like ‘the marketing piece’, or referring to ‘the ask’ rather than ‘the request’. And so on.
It’s also why any business has to evolve - constantly.
Our own history bears this out. ACM began life in 2005 as a ‘freelance writing agency’ providing stories and copy for brands, newspapers and magazines around the world. These days you’d probably call it a ‘content marketing’ agency (although that term didn’t exist back then either).
As the world has changed, so has our approach and the way we speak about it. Sure, we’ve had our fair share of false starts and followed plenty of blind alleys. But a willingness to experiment and change things up at a moment’s notice has been, I now realise, completely essential.
If you can’t do this, your business will have no longevity.
2. Have the difficult conversations early.
In any relationship, difficult conversations are inevitable. And absolutely everybody puts them off for as long as possible.
This is never a good idea. And it’s a particularly bad idea when it comes to company/customer relationships.
Why? Because after a while you realise that 99% of business difficulties are caused by a lack of clarity around expectations on both sides; the seeds of which are usually planted at the beginning of the relationship, when everybody is focussing on how great things are, and how you’re going to change the world together.
But difficult conversations will happen at some point. And if put them off, that gap of understanding you inadvertently propagated will have flourished dramatically. Leave it too long and it may well be too daunting to tackle, no matter how well things were going during those early years.
The solution? Have those tricky conversations during the honeymoon period when trust levels are at their highest, so clients know exactly what to expect when difficulties do arise.
Even so...

3. You will lose clients. You can also choose not to work with clients.
As ridiculous as it sounds, I only grasped the essential truth about having difficult conversations early after I’d been running the agency for quite a few years, and was trying to work out why a couple of promising early client relationships had foundered.
Losing clients is a fact of life in an agency like ours. When it happens, your ego and bank balance take the initial hit.
But when the dust settles, that lost client is an opportunity to learn, and improve the way you do things.
Clients walk for plenty of different reasons. A new marketing team comes in and wants to clean house. A global pandemic hits, and the brand has to cut their budgets. That gap between expectations I outlined above becomes too wide to bridge.
In my experience, by far the most common reason for deteriorating relations is when brands (almost always start-ups) go into the relationship without a clear understanding or why they want to use an agency in the first place (beyond ‘We should hire an agency! And this lot seem really cool and work with some of my favourite brands!’)
Or, fundamentally, they don’t understand how agencies operate, and lack the curiosity to find out.
This is especially an issue when you’re dealing with a client who is inexperienced with agencies, and gets panicky when they encounter the first bump in the road. By the time this becomes apparent to both parties, it can be too late to resolve.
That’s why, today, we try not to work with start-ups or overtly founder-led businesses unless there’s a really compelling reason.
And it’s why a huge part of our early interactions with clients is trying to understand if they have a clear idea of what they want and why they have decided to work with an agency. If it becomes apparent they don’t know, it’s time for awkward conversation number one as we try and help them work out what that goal is.
If, despite all available evidence and experience-based advice, the client still insists on following their original hunch, we’ll politely suggest that we aren’t the right agency for them.
In recent years, we have got much stricter at having yet more of these difficult conversations, and turning these jobs down (although, of course, there are still exceptions).
4. Beware the vanity metric
The point of all this is that a marketing strategy will only succeed if it is in service to a clear business goal that everybody understands. It’s why we spend so long getting to the bottom of a client’s reasons for working with an agency.
It’s also why what we refer to internally as ‘vanity’ metrics are so problematic. You know the type of thing: “We want to be the next Patagonia”. “Hey, brand X is in the Guardian - why aren’t we?” “We’ve just made the best brand film ever - can you help us get press for it please?”
We even had one client react to our carefully-compiled, strategically-led campaign plan with the words “I was expecting a golden carrot”. Enough said.
Vanity metrics like this are enormous red flags. It can be tempting to ignore these warning signs - particularly if they originate from a brand you really want to work with.
But what ego-led decision-making like this really demonstrates is a lack of leadership and, ultimately, a flawed strategy that is unlikely to succeed.
Agreeing to these metrics as a foundation for the work you undertake is really setting yourself up to fail.
5. ‘Company culture’ means something different to everybody involved
There’s an entire industry based around the alchemy of staffing and creating a decent company culture.
The truth is that only people who work for a company actually understand the reality.
In the case of ACM, myself and my co-founder Jojo are completely serious about ACM being a company where our co-workers take a share of the rewards their hard work have engendered. That’s why, last year, we set up an EMI Scheme, for example, and our long-term business plan is geared towards becoming a fully employee-owned company.
We also work very hard at making ACM a ‘good’ place to work, something which is an ongoing effort and intention.
That’s why, in the twenty years I’ve been doing this, I’ve probably been involved in literally hundreds of conversations about what ACM’s company culture is or means.
121s, team meetings, consultations, Belief and Behaviour sessions, Awaydays, HR powwows, NED-led Post-It marathons - you name it, we’ve had ‘em. (Indeed, taking part in and contributing to these conversations is a key part of the experience of working there).
So what have I learned?
At the risk of committing to perpetuity the type of godawful cringe statement that tends to surface on LinkedIn, I’ve come to realise that the truth about company culture is actually simple: there’s never any definitive conclusion.
Why? Because EVERYBODY (yes, I’m going nuclear with the full caps) has a different idea about what constitutes a ‘healthy’ company culture.
Some people want to be told what to do. Others can’t help but try and steer everybody else around their way of thinking. Some people relish the idea of a flattened hierarchy. Still others can’t think of anything worse. And so on.
The ‘point’, therefore, is to try and put the conditions in place so that the people who work there can take part in an ongoing dialogue, through which they can feel empowered to contribute honestly, and from which a transparent, open culture in which everybody has a say might then arise.
(This is easier said than done: not least because another thing I’ve learned is that getting people to be truly transparent and honest with each other in the workplace, whatever their role, and however progressive they think they are, is actually incredibly difficult.
That’s why a large part of my day-to-day role at ACM has always and continues to be spent basically encouraging people to be honest with each other).
But if you can manage this? You might just get somewhere.
6. It’s a constant organisational challenge - so systems are critical
“Be regular and orderly in your life, so that you may be violent and original in your work.” - Gustave Flaubert
Quite the (ahem) ‘advice piece’ there from yer man Flaubert, and something which goes to the heart of the importance of routines and systems in creating solid foundations for work, creativity and growth.
My ongoing mania for systems is a bit of a standing joke among our team at All Conditions Media. Especially after summer 2024, when I decided we needed to reorganise the entire company from top-to-bottom, and in record time, if we were ever going to have a chance of achieving or goal of employee-ownership.
But it was an important and necessary move. Because if you’re lucky enough to have a business that grows and evolves, effective systems that everybody understands (and uses, rather than inventing their own, which is more common than you’d think) are essential.
Efficient systems help your company run more smoothly, enable new staff members to settle in more quickly and help to set client expectations correctly.
They also provide your company with solid foundations for growth, and for when the inevitable storms hit. Speaking of which….
7. There will be hard times that are no fault of your own
“Events, dear boy, events”.
This was, supposedly, Harold Macmillan’s response when asked to name the single greatest difficulty he expected to face as Prime Minister.
And events, as the entire world has discovered over the last five years, can scupper anybody’s well-laid plans.
In the years that ACM has been in business, we’ve survived one pandemic, two global financial crises, the unexpected departure of a founding partner, and plenty of other sleepless night-inducing incidents that seemed calamitous at the time.
When seismic events take things out of your control, it’s important not to panic and take it too personally. (This is also when you’ll be very grateful you spent so long putting those efficient systems in place)
Because, viewed another way, such events can provide an opportunity to really focus and examine every aspect of your business. That’s what happened to us at the end of 2022, when a big client unexpectedly pulled the plug, and we took a huge financial broadside.
At the time, it was the worst thing that had ever happened to us. But in the end, it gave us the push we needed to shine a light in every hidden, dusty corner of our business (admit it; every company has them). As a result, we came out of it with a better understanding of who we are and what we offer, which has subsequently enabled us to come back stronger.
8. You’ll need to relinquish control
All business owners are narcissists, micro-managers and control freaks. How else would you have the confidence to start your own business in the first place?
In the early days, these traits are helpful when you need to switch between sales, marketing, accounts, HR and (if there’s any time left) the actual work itself.
But at some point, particularly as your business begins to grow, that will no longer be possible.
That’s when giving up control and accepting you can no longer keep tabs on every single aspect of the business becomes critical. And difficult. But, ultimately, rewarding.
If any business is going to grow, you need to accept that you can’t be involved in every single aspect of the business any more, and that you just need to trust your staff (and that marketing agency you spent all that money on - zing!) to do their jobs without interfering.
After all, it’s why you hired them, right?
9. Try and enjoy it - whatever happens
Has anybody ever successfully cracked the freelancer’s conundrum? You know the one. You give up your job and go freelance to enjoy more freedom and control of your time. Then spend that downtime stressing about all the work you’re not doing, thus defeating the point of why you went freelance in the first place.
This self-defeating dynamic is something that every business owner and self-employed person recognises.
And it’s why giving yourself permission to enjoy the entire thing is possibly the most important point on this entire list, especially if you’re a company leader.
How you react to the situations you face will hugely influence how your team reacts and will, ultimately, dictate the morale of your company.
10. You will make mistakes - the trick is learning from them
“Anyone who isn't embarrassed of who they were last year probably isn't learning enough.” - Alain de Botton
I posted this quote on Instagram the other year and it’s fair to say that it riled the fook out of everyone.
I get the sentiment though. I just read it as a fairly banal creative insight: if you want to achieve anything, get used to making a lot of mistakes, and make sure you’re honest enough with yourself to learn from them.
That’s basically been the story of my time running this company. Every now and again, whenever I’m spouting off about work to one of my long-suffering close friends, they’ll invariably say something like ‘Why are you still doing this? Why not put all this energy into something creative?’
To which my answer is: running a business like All Conditions Media IS creative. It’s one long set of problems to solve, and one long list of decisions to make.
The truth is that at no point during the twenty years I’ve been doing this have I had any idea what I’m doing.
Yes, I’ve gained experience, which means I trust my decision-making, have got used to a fairly high level of ‘risk’ (relatively speaking, of course), and have got very comfortable making fairly significant decisions.
But the mistakes, and how they accrue to become that nebulous thing called ‘experience’, are basically the point.
That’s why I’m still doing it. Well, that, and to see if it really IS possible to run a profitable company, do great work, AND treat people like human beings. But that’s another blog….
So many nuggets of wisdom in here... including plenty I'd never really thought of in these terms.
Enjoyed this one in particular “Be regular and orderly in your life, so that you may be violent and original in your work.” - Gustave Flaubert