The Messy Middle: Why Most Companies Get Stuck and How to Break Through
The stage nobody talks about
1. The Stage Nobody Talks About
Scott Belsky wrote a book called The Messy Middle. It’s one of the few works that names what most founders already know in their bones: the middle of building a company is the hardest, most disorienting, and least glamorous stage of the journey.
It’s not the zero-to-one spark.
It’s not the scale-up rocketship.
It’s the bit in between. The long slog where you’ve proven something but nothing quite works.
I’ve lived it multiple times now, both in my own companies and as an investor watching others. I’ve sat in boardrooms where growth looked fine from the outside, but inside the team was suffocating under chaos. I’ve had the late nights staring at dashboards and bank accounts, wondering if the next twelve months would make or break everything we’d built.
The messy middle is the stage where you’ve got:
Some customers.
Some revenue.
A product that people clearly want.
And yet every day feels like you’re treading water while carrying bricks.
It’s the stage where founders lose sleep, boards lose confidence, and companies lose their way.
And most never escape it.
2. What the Messy Middle Looks Like
If you’re in it, you’ll recognize the symptoms immediately.
Too many half-finished projects. The product roadmap is a graveyard of “in progress” ideas. Nothing quite ships, and if it does, it doesn’t land.
Too many customer types. Your sales team is chasing three or four different personas. SMBs, enterprise, agencies, prosumers. Every deal feels different. Every win feels like a one-off.
Too many priorities. Your leadership team has ten “number one” goals. Which means no real priorities at all.
Too many voices. Customers asking for features. Investors asking for metrics. Advisors offering conflicting advice. Your own team pushing in different directions.
From the outside, it looks like growth. New logos announced, new features launched, more hires made. From the inside, it feels like firefighting.
At ContentCal, I remember a year where everything looked great. ARR was climbing. We were landing notable customers. We had a growing brand in the social media space.
But inside the business, it was chaos. We had multiple roadmaps going at once. We were chasing agencies and SMBs and larger enterprise all at once. Everyone was working hard, but the energy was scattered.
That’s the messy middle: activity everywhere, momentum nowhere.
It feels like flying a plane while still bolting the wings on.
3. Why Companies Get Stuck Here
The messy middle isn’t a fluke, it’s inevitable. The question is whether you get out of it.
There are a few core reasons why most companies stall here:
1. The illusion of progress.
More features must mean more value, right? More customers must mean more revenue security, right? Wrong. Progress in too many directions cancels itself out.
2. The fear of saying no.
When every dollar counts, it feels reckless to turn one down. So you bend for every customer, agree to every custom feature, and contort your roadmap to serve everyone. Soon you’re serving no one well.
3. The busy trap.
Founders love motion. It feels good. It eases the anxiety of uncertainty. But motion isn’t momentum. You can sprint 80-hour weeks in the messy middle and not move forward an inch.
4. Investor pressure.
If you’ve raised, you’re under the microscope. Investors want to see ARR up, churn down, burn under control, pipeline full. That pressure can push you to spread thin instead of narrow deep.
The result: you burn time, money, and morale across too many bets.
That’s why so many companies plateau at $1–5M ARR. They’ve proven people want what they’re building, but they never do the hard emotional work of choosing one thing and betting the business on it.
4. The Emotional Work of Focus
Here’s the uncomfortable truth: escaping the messy middle is not a technical problem. It’s an emotional one.
On paper, the advice is simple: focus. Pick one thing. Drop the rest.
But in practice, it’s brutal.
It means killing projects you and your team have already sunk months into.
It means telling customers you won’t build the features they want.
It means saying no to board members who think you’re narrowing too far.
It means confronting your own ego, the part that wants to be “everything” to everyone.
I’ve been there. At ContentCal, we had to stop trying to serve everyone. Agencies, freelancers, SMBs, enterprise, we wanted them all. But the math didn’t work. We were spread too thin. We had to choose a lane.
That decision was emotional. It felt like letting opportunities die. It felt like betting the company on a smaller playing field. But it was the only way to break through.
The founders who make it out of the messy middle aren’t just the ones with good products. They’re the ones with the guts to focus.
5. Frameworks for Breaking Through
Focus isn’t just a mindset. It’s a set of practices you can embed into how you run the company.
Here are the frameworks I’ve seen separate the companies that stall from the ones that scale.
1. The One Metric That Matters (OMTM)
The messy middle thrives on distraction. The way out is clarity.
Pick one metric for the next 6–12 months. Just one.
Every roadmap item is judged against whether it moves that metric.
Every sales and marketing activity is aligned to it.
Every board update starts with it.
Examples:
Slack in the early days: daily active users sending 2,000+ messages.
Airbnb: nights booked.
At ContentCal, there was a stage where everything came down to one thing: monthly recurring revenue growth from SMBs.
If you can’t agree on one metric, you’re not ready to escape the messy middle.
2. The Customer Core Exercise
Here’s a simple exercise that cuts through the noise.
Write down every customer type you’re serving.
For each, note:
How much they pay.
How painful the problem is for them.
How easy they are to acquire.
Circle one. That’s your Customer Core.
Everyone else? Nice-to-have.
Your job is to obsess over your core customer until you’ve saturated them.
Most startups stall because they never do this. They spread themselves across too many personas. But the breakout stories always start with nailing one.
Slack nailed internal comms for dev teams.
Airbnb nailed stays in people’s homes.
Figma nailed design collaboration for small teams before expanding to the enterprise.
You can always expand later. But you need a wedge first.
3. Kill List Meetings
Every quarter, run a meeting where the explicit goal is to kill projects.
Each team brings its initiatives.
For each: does it serve the one metric? Does it serve the customer core?
If not, it dies.
This is hard. It goes against every instinct. But it forces clarity.
At JAAQ today, we’ve had to do this repeatedly. It’s easy to say yes to partnerships, pilots, new verticals. But unless it drives the core, it gets cut.
4. The Ruthless Roadmap
Force rank every initiative. 1 through n.
Then draw a line under the top three. Those get resourced. Everything else doesn’t.
When someone tries to sneak in project #7, remind them: it’s below the line.
This isn’t about being rigid. It’s about discipline. The messy middle thrives on half-finished side projects. A ruthless roadmap kills that.
5. Weekly Focus Cadence
Make focus part of your company’s operating rhythm.
Monday: each team defines the three things they will do this week that move the one metric.
Friday: review. Did we do them?
No vanity metrics. No busywork. Just progress on the one thing.
When you embed this cadence, clarity compounds.
6. Focused Fundraising Narrative
Investors smell chaos in the messy middle. They get nervous when you’re chasing too many things.
Flip it.
Anchor your fundraising story around:
Your customer core.
Your one metric.
Your roadmap discipline.
Paint a wedge strategy that expands into a huge market.
Investors back momentum, not chaos. If you show them you’ve cut the noise, they’ll fund you through the mess.
6. Execution Discipline
Frameworks are only useful if you embed them in execution.
Here’s what it looks like:
Product: one core customer, one metric, one roadmap.
Sales: qualify ruthlessly. If the lead isn’t your core, pass.
Marketing: one channel, one message, one growth loop.
Team: weekly cadences that enforce focus.
Founder: the emotional discipline to say no — to investors, to your own ideas, to the shiny new thing.
The messy middle thrives on distraction. Execution discipline kills it.
7. Case Studies: Focus in Action
Slack. Started as a side project from a failed game. They didn’t launch as “collaboration software.” They focused on one thing: team chat. They made it effortless. They measured one metric: messages sent. Focus turned them into a juggernaut.
Airbnb. For years, they weren’t hotels, experiences, or luxury stays. They were just: stay in someone’s home. That focus made the brand iconic. Expansion came later.
Figma. Early on, they obsessed over small team collaboration. It wasn’t until they nailed that use case that they scaled into enterprise.
ContentCal. We had to cut enterprise pursuits, and side bets. Once we focused on SMB SaaS growth, things accelerated. That focus is what ultimately got us to acquisition.
The pattern is consistent: focus is the lever that breaks companies out of the messy middle.
8. The Payoff of Focus
Here’s what happens once you commit:
Your team finally knows what success looks like.
Your customers finally know what you stand for.
Your investors finally see a story worth betting on.
But most importantly: your energy compounds.
Instead of spreading time, money, and morale across ten projects, you push all of it into one. That’s when you break through.
That’s when you move from messy middle to market momentum.
9. Closing: The Founder’s Challenge
If you’re a founder in the messy middle, here’s the challenge:
Stop trying to do everything.
Pick one thing. Bet the business on it.
Yes, it will feel reckless. Yes, it will feel like letting people down. Yes, it will feel like you’re walking a tightrope without a net.
But that’s the work.
The messy middle is the hardest stage because it demands not more intelligence, but more courage.
The companies that escape it aren’t the ones with the most features or the widest market. They’re the ones with founders who had the guts to choose.
Scott Belsky was right. The messy middle is brutal. But it’s also the crucible.
The companies that survive it are the ones we all read about later.