Don’t kill the entrepreneurship.
Originally sent exclusively to The Letter subscribers on August 31st. Want to be the first to get my personal newsletter in your inbox every Monday at 7am? Subscribe for free here.
Don’t Kill Entrepreneurship as You Professionalise
If you’ve read any of my dribble, listened to me harp on, or watched any of my videos, you’ll know that E + M = S is my absolute north star for business success.
Entrepreneurship + Management = Success.
It’s the yin and yang of business. You need both.
But there’s a danger.
As you professionalise a business, don’t accidentally professionalise the entrepreneurship out of it.
If you want to scale past £1m of revenue, £10m, £30m and beyond, you’ll notice something starts to happen.
The organisation naturally becomes more management-heavy.
It almost always does. And I understand why.
Management is the safer bet. As businesses get bigger, there’s more to lose. More people. More overhead. More complexity. More stakeholders.
So you can find yourself slowly edging towards safer waters.
Steady Eddie starts looking quite attractive.
But remember this:
Entrepreneurs start things and change things. Managers protect and improve things. A great company will have tension between the two.
Managers naturally gravitate towards the status quo. The status quo is exactly what entrepreneurs seek to disrupt.
Here's a thought. Management was perfectly happy with maps. Entrepreneurs wanted sat nav for everyone.
I see this in my own companies. The desire for an easier ride will nearly always come from trusted advisers, professional managers and experienced teams. Especially in tough times.
And I want management. I need management.
But I think a truly ambitious company needs to retain something like 51% entrepreneurship and 49% management.
Lose that entrepreneurial edge and eventually someone comes along and does to you what Netflix did to Blockbuster.
The Entrepreneur’s Entrepreneur.
In a shake under 60 days, I’ll be travelling to a conference where I’m due to spend time with Sir Richard Branson at his home on his private island in the Caribbean and do a key note for him and some other seriously driven entrepreneurs.
Meeting one of my entrepreneurial heroes will be a big day for me.
Staying there for six days?
That’s a whole other level.
In preparation for meeting the entrepreneur’s entrepreneur, I’ve been rereading his fantastic books on business and sharpening the saw with a host of videos and podcasts while I’ve been sunning my trotters in Mexico with my family this past week.
And something has really struck me.
The entrepreneurial brain can solve problems that the management brain sometimes can’t.
Listening again to how Sir Richard navigated business near - business death experiences with completely outside-the-box entrepreneurial solutions has wowed me.
When things got really difficult, he didn’t always retreat.
Sometimes he doubled down. Sometimes he expanded.
Sometimes he found a completely different route around the problem.
The James Sinclair way too, as it happens! (the book certainly rubbed off on me)
The 16-year-old me devoured his books. They were my Bible for business philosophy.
I knew he’d had brushes with failure, but I’d forgotten just how close he came to running out of cash on multiple occasions.
Reading those stories again at 41 has been strangely comforting.
Like meeting your first love again and remembering all those passionate feelings you had the first time around.
The thing I’d forgotten was just how many times Sir Richard came frighteningly close to business death before achieving enormous success.
It wasn’t until around his early forties, after selling Virgin Records, that he finally had the sort of financial freedom that changed the game.
That stuck with me. He was running a multi million pound empire with fresh air but tons of prospect.
When Tough Knocks on the Door
Rereading these books, alongside others including The 7 Habits of Highly Effective People, and combining them with my own experiences of business and people, has led me to a conclusion.
When tough knocks on the door, I generally see people do one of three things:
1. They die.
Not literally!
The business dies.
The entrepreneur, founder or manager with an entrepreneurial twang simply can’t be arsed to innovate anymore.
They take a convalescence, lick their wounds, get a job, or eventually summon the energy to go again.
2. They retreat to safer waters.
This is probably the most common.
They save what they can and retreat into a smaller, safer enterprise.
Maybe they had a multi-site restaurant business with 45 employees and retreat back to one site with 12.
It might be profitable. It might even provide a nice living.
But effectively, they’ve built themselves a job.
Safe waters.
3. They innovate.
They find the outside-the-box solution.
They accept that the next 18 months might be bloody difficult.
They keep moving.
They keep solving.
They stay in the game.
And when they eventually break through, they can take quantum leaps forward.
That third option interests me most.
Pain Tolerance.
I think pain tolerance is where you really discover who you are.
Protecting your reputation.
Surviving a cash crunch.
Dealing with backstabbing.
Handling loss.
Dealing with disappointment.
Standing up to nasty people.
Getting knocked sideways by something you never saw coming.
And then?
Moving on like the wind.
That last bit is important.
The entrepreneurs I see achieve mega success are remarkably good at standing up for themselves and then moving on.
Bad energy is bad for business.
Hopscotching over it is often the fastest route back to peace.
I’ve learnt that with enough persistence, you can solve almost anything.
You just have to stay in the game.
You may lose some battles.
You’ll make mistakes.
You’ll get things wrong.
People will disappoint you.
Plans will fail.
But getting back up, managing your mood and maintaining your drive might be one of the most important entrepreneurial skills of all.
You’re allowed to have a bad hour.
Very occasionally, you’re allowed to have a bad day.
But remember this:
If we’re lucky, we get roughly 4,000 weeks on this planet.
By my maths, I’ve got around 1,861 left.
I want to spend those weeks with the best people I can.
I want to do work that fulfils me.
I don’t want mood hoovers.
I don’t want small-minded thinking.
I don’t want to waste precious weeks worrying about people and problems that ultimately don’t matter.
Because in 100 years, most of us will be forgotten anyway.
So when you find yourself in those moments of toughness and wilderness, think like an entrepreneur.
Management will naturally try to bring you back towards safer shores.
Sometimes you should listen.
But sometimes the wonderful result you’ve been chasing is only a few more painful steps beyond the point where most people stop.
Do the extra rep.
Stay in the game.
Keep innovating.
Keep planting.
Keep moving.
But there is one massive caveat.
You need to be bloody sure about your model, your vision and your margins.
Persistence cannot rescue a fundamentally rubbish business.
You can’t polish a turd.
But when the fundamentals are right, don’t let professionalisation kill the very entrepreneurial spirit that created the opportunity in the first place.
You need the managers.
You need the systems.
You need the scorecards.
You need the processes.
You need accountability.
But you still need the lunatic in the room saying:
“What if we did this?”
That’s why I believe so strongly in:
Entrepreneurship + Management = Success.
Neither wins alone.
And as always:
Yes, it’s hard.
That’s the admission price great things charge.
To your continued success,
James
P.S. It’s an unwritten rule of life that tough times don’t last.
Unfortunately, neither do the good times.
So always be planting the next seeds.
The wonderful thing about experience is that each time the seasons change, you become stronger and wiser.
You learn which seeds to plant.
You learn where to plant them.
And you learn how to nurture them faster.
Never stop planting.

