How to challenge the status quo, overcome the odds and build 5 businesses all at once

Take the journey with an entrepreneur who hates the status quo and loves a challenge — to build and deliver 5 businesses at once.

Accepted wisdom tells us that starting and running more than one business at once is a completely stupid and impossible pipe dream that only wantrepreneurs and the truly naive would attempt.

Yet no one has proved this definitively! Who said so? What gives them the right to assume you won’t succeed where they failed? And why should we accept the status quo?

Well i’m here to accept the challenge on your behalf. To dive into the under-documented and hazy world of multiple business creation. Like a small child on an innocent journey, deep into the invitingly beautiful but inevitably dangerous wild lands, I’m setting out to find out just what it takes to start up, not one, but FIVE businesses all at once, from scratch and get them operational and profitable as quickly as possible. Can I succeed? Will i fail? Where will I be 1 year from now? Dancing the jig of joy? or dribbling in terror at the bottom of the pit of failure?

Join me on this crazy journey — if only to laugh and shake your head whether I fail, succeed against all the odds or just run in circles clutching my head. How many monsters will I face and defeat? How often can I fall, get up and keep going? Is there a path through to success? What secrets does it hide? Who will I meet along the way? Will they lend a helping hand? and… most intriguing of all, what if it works? What will we learn? Would this change business development as we know it? And, what do the five faces of simultaneous business success look like?

Maybe, before we launch into the deep, I should tell you a little about myself and what brought me to the edge of this …adventure.

— — —

I’ve rewritten this sentence eight times already. My mind has been flying the whole time and 100s of starting bells have rung in the half minute it’s taken me to punch out the following full-stop (Period to our American friends, but i’m British …so full-stop it is).

…and that’s half a problem for me. This pulling of my mind, into a thousand directions, tangents and rabbit holes. I say ‘half a problem’, because i’ve realised over time, that as much as it is an affliction, it’s also what I like to consider my super-ish-power.

While it can be a hinderance in terms of procrastination, I’ve realised that with good management and structure it can make me highly productive, and in terms of creativity, it can be a real boon!

Let me explain.

BTW before I do, i’d just like to say i’m really loving the simple layout of Medium’s writing space! Space is the correct term. It’s refreshingly simple and clean with no distractions — perfect for someone like me.

OK where were we…

When I was a kid my mum would call me a dreamer. I’d dream the day away if I could. A lot of things i’d do on autopilot whilst thinking of the weird and wonderful places I would go, all the things I would do on my travels. Very few of those travels were to real world destinations. They really were flights of fancy.

We had a cupboard under the stairs. It was dark and full of odds and ends (and at one point, mouldering sandwiches, which is a whole fascinating story for another time). I would pass it on odd days and dream that in that cupboard under the stairs, was another set of stairs — leading down to many unknown and different worlds. I used to imagine what it’d be like to walk down and into another land with weird creatures and wonderful people. So one day I decided to give it a go!

I entered the cupboard, pulled the door shut and sat in the darkness and let my imagination fly! I can’t begin to tell you about the amazing worlds that were conjured up before me …mostly because it was over 40 years ago and a lot has happened since. But that cupboard helped me appreciate my imagination and reinforced my love of dreaming outside the box.

As I grew older, I started to believe that concentration wasn’t top of my list of favourite past times! At school I’d rather dream up a use case for algebra where my implementation created a spectacular (if impossible) outcome, rather than actually concentrate on the ‘mundane’ task of working through the problem on page.

Stimulated in the right way however, solving problems and finding solutions was where I was happiest. Later on in life, this took the form of Graphic Design. I have to say, for anyone who loves solving problems whilst making the solution look good and getting paid for it — Graphic Design is a great career move.

My mind was always jumping through six or seven subjects and scenarios while I’d sit in meetings with clients. Sometimes I’d snap back to the present, realising i’d been mentally finessing a design while the client talked about their pressing needs. Yet, I also found that my mind picked up tiny details that were always useful in finding solutions. I didn’t consciously pick them out at the time they were spoken, yet they came back to me when i needed them.

It is this connecting of dots, or reconnection of data, like teasing out a future path from past hidden details, that has always fascinated me. It works for me, within my daily workflow as I conceptualise and look for creative answers to problems, so maybe it can be quantified, systemised and utilised as a way of breaking through other business problems?

Progressing through the various levels to Studio Manager at the age of 24 and on to Creative Director, my career placed me in many different roles, right across the industry. I learned from every position. I really soaked everything up and thoroughly enjoyed pushing my own boundaries to see what I was capable of.

I am curious by nature. Always trying to understand as much as I can about anything that I feel could do with improvement. Even if that improvement makes only a tiny hint of a positive difference, or improving something that is such a small detail, it’s lain unconsidered or unremarked.

In 2008 I became curious about why I was so dedicated to giving 12 hour days to a company, who made 4 times more out of me than they paid me.

It wasn’t just about money though, they paid very well — it was also about freedom. To be in a position to work to my own time, pursue other avenues and be present for my kids as they grew, was really satisfying.

And i made a discovery that surprised me. I found i could now spend hours on end, concentrating on whatever task was before me — no longer bored and looking for escape! So, what had changed?

The only change was my focus. I had new goals, the drive to create the best experience for my clients I could. One that would hopefully make them come back again and again. I wanted them to feel they had never been treated so well before. So I was happy to work all hours, often producing more than they asked for and making sure the quality was right up there.

And it worked. For the last 16 years i’ve been happily satisfying my clients, many have been with me for over 14 years. I was even invited back by my old company to work as a digital design consultant — a gig that was supposed to last a couple of months and ended up stretching over 2 years.

Once that ended I began working for a gov agency, helping them realise their new brand vision, fulfilling a number of photographic assignments for them, doing some traditional design for print work and creating animated films.

Then in 2023 my life changed.

I started getting bad indigestion which would come and go. Gaviscon helped to start with, but then it didn’t, until one Saturday night in June I went to bed, and couldn’t sleep. The indigestion was so bad it kept me awake. So I crept out of bed on the Sunday morning at 5:30 and drove to our local accident and emergency centre. It was closed.

I returned home and lay in bed until 7:30 then woke my wife and said I needed to go back to A and E. We arrived as they opened and I was one of the first they saw. My blood pressure was 210 / 140. They said i’d need to go to the main hospital to get checked out. So off we went and I remember sitting in a bed, with a needle in my arm hoping they’d give me some Omeprazole and i could go home, when the Dr arrived to tell me they had checked my bloods and they were very sorry but I was having a heart attack.

However, as the National Health Service in the UK is completely strapped for cash, their heart surgery team did not work on Sundays. My saviour arrived in the form of a young surgeon who had been working remotely. He’d read my file and came into the hospital to request i be sent to a top teaching hospital who also have one of the best heart specialist units in europe.

They blue-lighted me to this new hospital and rushed me straight into surgery. I lay awake, watching the wires being run up my veins into my heart, as they positioned stents and ballooned arteries. To be honest, it felt more like an adventure than a life-threatening situation.

Then the recovery. I was informed under no circumstances, was I to work in any capacity …for 4 weeks, and longer if possible.

To be told I couldn’t even switch on a computer and work seemed, almost wrong — I wasn’t physically labouring, what was the issue?

The issue is the brain is the most oxygen hungry organ in the body. The brain consumes huge amounts of oxygen when under stress, just as a bicep burns more oxygen with the curl of a dumb-bell. The amount of oxygen used by the brain is far higher than the other organs and muscles in our bodies over the space of a day. And this need for oxygen puts strain on the heart. So even sitting and thinking about work, is stressful to the brain and subsequently the heart.

I was skeptical, and even tried to do a little work about 3 weeks in, but I soon realised that they were right. I could work for 20 minutes, but then i’d feel exhausted. My clients were very understanding and helpful. I was in the middle of a major rebrand for one client, and it was going live 2 weeks after the date of the attack. There were many complex elements and parts that needed to be delivered, including printed materials and branded items.

However luckily I had most of it done, and at a stage where I could pass the files to a trusted and very capable contact of mine in the print business.

And so we arrive at today!.. some months since ‘the incident’ as I call it. I’m feeling much better, but I also realise that, should this happen again or anything else that might incapacitate me, how would I help my clients? what systems were in place for them to keep receiving the same consistent service they looked to me for? And what about me! How could I keep on providing, even if I wasn’t around to do the work myself?

I feel this is a problem that many freelancers and solo entrepreneurs experience every day. You trust you! Your ability to deliver the best product or service your way. Trusting anyone else to help is… dangerous.

Yet, while the best ideas in human history all came from a singular brain at conception, the best progress in human history has always been a collaborative experience.

My first problem was the number of thoughts going through my head, maybe this was time to change direction again? maybe I could set up other businesses that would run automatically so I could continue to bring money in even if things went south.

And now my brain decided to revert to its natural state — procrastination! How was I going to drive this forward in a way that kept my brain happy, my clients happy and me happy? I wracked my brains for a solution and it came in a surprising way.

One evening I sat, eyes glazed, staring right through my list of ‘multiple streams of income’. To snap out of it I decided to watch an episode of Steve Bartlett’s ‘Diary of a CEO’. In this particular episode he was interviewing the Founder of MoonPig. I got half way through and was thoroughly enjoying the show, and then they alighted on the subject of entrepreneurs running many businesses …and my heart sank.

Steve said he couldn’t trust or invest in an entrepreneur who had more than one business on the boil at any one time. “Focus on one idea” was the thrust of his lance. It cut deep and hurt I have to say.

So now, my problem had expanded! How to focus on one business, yet deliver all the business ideas I’d come up with :)

You see, (don’t tell Steve) i’ve never really bought into that theory. It raised the boil of that particular status quo and Mr Bartlett I quietly chided (i’m a huge fan btw), wasn’t a man who abided by his own thesis either! (He was running at least 3 of his own businesses and involved in many more at the time).

It just made me more determined to attempt to prove the theory wrong.

Like you, I know the majority of breakthroughs, amazing inventions, culture changes and forward leaps in human history (often in the face of great adversity) can be attributed to many people who challenged the status quo. Edison, Nikola Tesla, The Wright Brothers, Sarah Boone, Einstein, Claudette Colvin and Rosa Parks, Martin Luther King, Steve Jobs/Wozniak — the list is endless.

So I decided it was time. Let’s find a stairway down into the forbidden land of multipreneurship! It’s time to stalk that land in search of its delightful secrets. Let’s see if it’s willing to give them up.

The problem:

Building multiple businesses all at once will simply cause confusion. Each business is different, with different challenges, needs, customers, arenas, competitors, and timings of development — to name a few.

So the solution can’t be more of the same where we try to divide our time focusing on each business. That really is a recipe for disaster — mainly our own mental demise.

So, if we can’t focus on each business at the same time then we need to look at the levers of control. Focus on the puppet master, not the puppets.

If there is any success to be had at all, I have to focus on the system that allows me to build my businesses. The infrastructure, the people, processes, tools, methods of delivery, everything that is needed when building a solid business. Systemised yet flexible, agile, modular and 100% rules based. Written down, rehearsed, tested, retested and tested some more.

All of these elements need to be separate modules, that fit seamlessly together like Lego in any formation, so we can plug in the relevant pieces for each business at the right time, knowing that the formulas they’re based on are sound, tried and tested.

And what better way to test the system, than 5 test businesses! Each a different sector with its own goals, set up from scratch. That’s my solution.

And what if this fails?

Well! the reality is some may fail. They ALL may fail (I hope not) but this is an experience that gets me excited! In many ways it’s what Nick Jenkins said to Steve Bartlett in the same episode of DOAC

“it’s not the destination, it’s the journey”

So, this is my first post! I hope you’ve managed to read it to the end and that you’ll come back to read more. My aim is to use this blog as my diary, a documented journey of a man who likes to challenge the status quo, overcome the odds and build 5 businesses all at once.

Wish me luck! …Or tell me i’m stupid. Either way i’m happy to engage with you, accept your advice and even your help if you’re feeling generous at any point along the way!

Here’s to the journey!

Ali McDee