When a £250K Mistake Teaches You Everything
- Samantha Riel
- Jul 9
- 5 min read
What a £250,000 Loss Taught Us About Scaling Systems That Actually Work
In a recent conversation with Greg Dorban, CEO of Comfy Workers, we unpacked what might be one of the most expensive lessons in operational friction.
His company lost a £250,000 deal over a form.
Not a failed product. Not a poor customer experience. A form.
That single experience revealed something that many growing businesses eventually face: in the push to scale quickly, companies often simplify too soon and standardize too little.
At the surface, it looks like a process failure. But under the hood, it's a lesson in complexity, customer fit, and what it really takes to build systems that last.
Most Problems Aren’t Invisible. They’re Ignored.
Comfy Workers didn’t start with a flashy SaaS vision. It started with a logistics headache most people don’t even realize exists: business travel for construction crews, key workers, and teams who stay on-site for weeks or months at a time. The market assumed the problem was already solved. People knew how to book travel. But what they didn’t account for were the variables.
What happens when six workers need housing for four weeks, and then three leave while five more join?What if they need secure parking for vans or 24-hour access to the property?What if the people coordinating the booking are admin managers, not travelers?
The details were too complex for mainstream travel platforms. But they were too routine to feel like a market opportunity. Most people walked past the problem.
And that’s the point: the most valuable growth often lives in the friction other companies ignore.
B2B Complexity Isn’t a Bug. It’s the Business.
One of the most revealing parts of the conversation was this: sometimes simple doesn’t win.
The £250,000 loss happened because Comfy Workers required a standardized booking form. Their customer required a different process. Neither side could budge. The deal collapsed.
Could they have bent the rules to win the deal? Maybe. But then the system breaks. One custom exception becomes two. Compliance slips. The business model shifts. And suddenly what was scalable becomes a patchwork of one-off fixes.
This is the tradeoff most teams miss.In B2B, standardization isn’t just about efficiency. It’s how you protect your ability to scale.
Sometimes complexity is exactly what your customer needs.That doesn’t mean you sacrifice structure to win the sale.It means you build systems that can hold both.
Operational Fires Aren’t a Phase. They’re a Feedback Loop.
Every founder talks about firefighting. But few step back to ask what those fires are trying to reveal.
Greg shared a story about a booking gone sideways early in the company’s journey. It wasn’t one mistake that caused the problem, it was a chain reaction. The host wasn’t onboarded correctly. The guest damaged the property. The team had no policy for resolving the dispute. No one was quite sure who was liable. It took three weeks to resolve.
That kind of chaos is familiar. What stood out was how his team responded.
They didn’t just fix the immediate issue. They used it to redesign their onboarding process, tighten contract terms, and formalize accountability between booking contacts and end users.
It wasn’t about preventing that specific problem again.It was about asking: “What system would have made this impossible?”
And then building that system: quickly, intentionally, and with the entire business in mind.
You Can’t Build a Process If You Don’t Measure the Problem
A phrase that came up again and again: “It happens a lot.”
That is the most common, and least helpful, way teams describe friction.
When Greg hears that, his first question is: “How often is a lot?”Once a day? Once a week? Once a month?If no one knows, they start tracking. Every instance. Every pattern.
Only then does the decision get made:
Is this happening frequently enough to matter?
What’s the downstream impact?
Can it be fixed manually for now, or does it need to be built into the system?
And critically:
Are we solving the root cause—or just what feels urgent?
That approach doesn’t just save time. It saves the team from fixing symptoms instead of systems.
Fixes Don’t Need to Be Perfect. They Need to Be Measured.
One of the most practical takeaways from the conversation was how Comfy Workers approaches process iteration.
Here’s the cycle:
Someone notices a recurring friction point
The team documents every time it happens
If it hits a threshold, they implement a manual workaround
If the workaround still requires too much effort, they build a permanent fix into the product or process
It’s not glamorous. But it’s effective.
By the time something becomes part of the platform, it’s already been tested, tracked, and measured. No more gut decisions. No more guessing what might help. The change is grounded in reality.
It also keeps the team focused on what matters, solving problems that affect multiple users, not just reacting to isolated complaints.
Time in the Market > Time at the Desk
Greg shared that Comfy Workers wasn’t a full-time venture at the beginning. And in hindsight, that slow start was one of the company’s greatest advantages.
Why? Because being in-market over multiple seasons created pattern recognition. The team wasn’t reacting to spikes or anomalies. They had seen the rhythms. They knew what “normal” looked like across time zones, industries, and customer types.
It also gave the business space to mature without the pressure to chase every short-term win.
There’s a lesson here for other founders: scaling fast is valuable. But staying in the game long enough to understand it is priceless.
Standardization Doesn’t Mean Silence
One of the biggest challenges growing companies face is the breakdown of feedback.
In the early days, everyone hears everything. The founder knows what’s broken because they’re in the weeds. But as the company grows, information filters. Leaders miss signals. Pain points get diluted.
Greg talked about this in the context of missed insight. Not because his team wasn’t communicating, but because the informal moments were gone. The side comments. The unfiltered frustrations. The “this happens a lot” anecdotes that often lead to real innovation.
Without systems to capture those signals, important problems hide in plain sight.
The fix isn’t just better reporting. It’s creating a culture where information flows both ways, where frontline teams know their input drives change, and leaders make time to listen deeply, even when it’s inconvenient.
Trust Isn’t a Nice-to-Have. It’s the Entire Brand.
In the final moments of the conversation, Greg shared what he believes is the most underrated business superpower: trust.
It’s not about telling customers what they want to hear.It’s about telling them the truth, even when it’s hard.It’s about doing what you say you will.And it’s about building a reputation so solid that when something goes wrong—and it will—your partners know you’ll fix it.
Trust isn’t a marketing strategy.It’s what makes marketing work.
And it’s what allows businesses to build with confidence, even in complex, unpredictable markets.
The Lesson Behind the £250,000 Loss
The lost deal was painful. But it surfaced something far more valuable than short-term revenue.
It reminded the team that real scale comes from structure.That building for ease on the front end can’t come at the expense of backend stability.That system gaps show up in sales numbers.And that simplicity isn’t the goal. Accuracy is.
If something is breaking often enough to get noticed, it’s worth fixing.But if it’s breaking because the system wasn’t built to hold real-world use cases, it’s time to rework the foundation.
Fires are going to happen.The only question is whether your team uses them as signals, or waits until the next one burns twice as hot.
Listen to Episode 4: When a £250K Mistake Teaches You Everything
🎧 Spotify 🍎Apple Podcasts ▶️ YouTube
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