Are You in the Messy Middle?
(As Marshall Goldsmith famously said, 'What got you here won't get you there' - and every founder scaling past $5M knows exactly what he means.)
Three conversations this week. Three different CEOs. Same frustration:
"Our scrappy marketing worked brilliantly. Until it didn't."
Sound familiar?
You've hit that point where what made you successful so far won't get you to the next level. Your founding magic feels under threat. Traditional marketing approaches feel like they'll kill what makes you special.
Welcome to the messy middle.
The Learning Curve Nobody Talks About
There's this brutal phase in every growing company's journey. You start with enthusiasm: "Let's go!" Then reality hits. The path gets tangled. Suddenly you're asking "What is this shit?" followed quickly by "Oh no! I don't know what I'm doing."
Most founders think they're alone in this chaos. They're not.
The messy middle is where you're caught between scrappy and scalable, between intuition and insight, between speed and systems.
What It Actually Looks Like
You know you're there when:
Your team is burning out from wearing too many hats, but hiring feels risky. Your messaging worked when you were nimble, but now it's getting lost in the noise. The marketing that got you noticed isn't scaling.
You need structure to grow, but you're terrified it'll kill your founding spirit.
The False Choice
Here's what most founders think they have to choose:
👉 Keep doing what's scrappy and safe
👉 Or hire expensive help that doesn't get it
But there's a third option: bridging the gap without losing your soul.
What I've Learned
Twenty-five years building campaigns for MasterCard, HSBC, and GSK taught me something: Fortune 500 discipline works. But so does entrepreneurial spirit.
The magic happens when you combine them.
Not by choosing one over the other, but by finding the intersection. Big brand thinking with startup agility. Structure that enhances rather than strangles. Marketing that scales without selling your soul.
The Way Through
The companies that successfully navigate the messy middle don't abandon what made them successful - they evolve it.
They add AI-powered insights to founder intuition. They build scalable systems around their core strengths. They professionalise without becoming corporate.
They bridge the gap between where they are and where they want to be.
Why This Matters Right Now
AI is accelerating everything. The companies that figure out how to blend human insight with machine intelligence, entrepreneurial speed with strategic discipline, will leave everyone else behind.
The messy middle isn't a problem to solve - it's a competitive advantage to claim.
Ready to Navigate Through?
If you're a CEO or founder who recognises this feeling, you're not alone. And you're definitely not stuck.
Sometimes the best way forward starts with understanding exactly where you are and mapping the clearest path to where you want to go.
Start with a Messy Middle Marketing Assessment
Get AI-powered insights into your exact growth blocks and a strategic roadmap to break through.
Investment: $3K-5K | Timeline: 1-2 weeks | Outcome: Clear diagnosis + prescribed pathway
What's your messy middle story?
