Scale is the thing you’re supposed to want when you’re building a business.
You tell yourself the company will become easier to hold together once there are other people helping. It should stop depending so much on you and your ability to keep dragging things forward.
Across Millennial Masters interviews, I’ve spoken to founders who got there, with hundreds of staff and revenues running into the hundreds of millions, and sometimes beyond. Then the worries changed.
The old business started failing before the new one was fully built. The job changed, and they moved further away from the work that made building it exciting in the first place. 👇🏻
The old company breaks first
Joshua Western said going from 50 people to 60 was harder than going from 2 to 50. Around 50 people, “the things that you set up, the ways of working, what little processes you try and have as a startup, all fall over.”
Growth puts more pressure on the company and shows how much of it was being held together by people who knew what to do without being told.
A lot of what looked solid was really people filling gaps, remembering what mattered, and sorting things out because the team was still small enough for that to work.
Then the company reaches a size where those old shortcuts stop working, and suddenly simple jobs need more chasing than they used to.
Emma Mills described this break point. Once a company reaches seven figures, what got it there doesn’t get it to the next stage.
The early version relies on people doing whatever needs doing. The next one needs clearer roles and fewer important calls stuck in one person’s head.
That can seem daft when you built the business on speed and instinct. If you ignore it, the problems show up somewhere else.
Headcount can lie
Noel Andrews dealt with one of the easiest founder vanities: headcount.
He scaled to 17 people and thought that meant the business was moving forward. From the outside, it looked like a bigger, more serious business.
Inside, it was chaotic. The company looked like “a graceful swan on the surface,” while underneath there was too much paddling and too little control.
Then he went back down to eight people. The smaller team did twice as much work and made three times the profit.
More people can make the business look more real. They can also create work that only exists because more people are there.
Add people without rebuilding how the company works, and you can make the business look bigger from the outside while it gets worse inside.
The job changes on you
Tyler Dunagin looked back on his own journey and described the founder role as a move from all-star NBA player to coach, and later towards the owner’s box.
At the start, you’re on the field. You’re doing the work, solving all the problems. Then scale starts pulling you away from that closeness.
It sounds sensible until you’re the one having to make the swap. Some founders are good at the early fight and much less comfortable in the role the company needs later.
Nick Telson-Sillett recalled meeting people by the coffee machine in his own office and realising he didn’t know them because he hadn’t been involved in hiring them. They would ask what he did, and he would say he was the founder.
You can become a stranger inside the company you built. That’s the part founders don’t always see coming.
The job changes from being close to the work to building a company that can keep moving without you touching everything. Yet you can still miss the version of the business where you felt useful in a more immediate way.
Early heroes can turn blockers
Simon Penson said it’s the growth stage where someone in the room feels so important that, if they left, the business would be in trouble.
Startups depend on people like that. They stay late and help the company survive when there’s no real structure around them.
Then the business grows, and the person who was essential at the start can become a blocker in the next stage, because that step needs something different.
A practical generalist can struggle once the business needs a specialist. The person who did three jobs may not be the right person to lead one of them at scale.
That’s hard because the role has history attached to it. You remember who helped when the business was still fragile and the future wasn’t always clear.
Their contribution can still matter. The problem starts when you keep them in the same role because you feel you owe them.
Then everyone else has to work around it. People cover the gaps, standards slip, and the business starts fitting around the person instead of the work.
That’s how loyalty becomes expensive.
Clarity becomes part of the work
In the early stage, people sit near each other and things keep moving because whoever needs to fix the problem is close by. You can get away with a lot when everyone knows the backstory.
Nick Holzherr remembers the gap between 30 people and 120 people. At that size, you have to think much harder about how things are said and done, so they still make sense when you’re not there for every decision.
More time goes into writing things down so people can act without you explaining it each time. It’s necessary work, and it’s less fun than a quick conversation with those who already understand the business.
Andrew Steele understood a business with 100 people shouldn’t feel like a startup with five. You can’t just run it over WhatsApp any more.
You can keep trying to hold on to the startup feeling long after you’ve outgrown it. Eventually, people need to know what good looks like without asking you every time.
That may feel slower, but it’s just what happens when the business is no longer small.
The numbers get heavier
From the outside, scale can make a company look safer. More revenue and a bigger team suggest the fragile early stage is over.
James Fleming looked back at the early years and said that if he’d seen the later outgoings, he would have cried. The business reached around £135,000 a month just to keep running.
That kind of number changes the company. You can have more revenue and feel less free because the cost of being wrong grows with the business.
Kevin de Patoul lived the hypergrowth version. His company went from 15 to 60 people, then after raising $70 million, from 60 to 160 in 12 months. His warning was that if you keep pushing forward without looking at what’s breaking behind you, things can start imploding.
That’s the danger of scale. The business can look stronger from the outside while small problems are getting more expensive inside it.
The job you wanted disappears
Joshua Dziabiak loved the stage where the job was still about making something. You could take an idea from nothing and turn it into a real business.
Then the company scaled, and the work changed. He described it as “financial engineering.” The big moves became smaller, more careful ones. The work became about keeping a larger machine on track.
The business had succeeded. The work that made it feel alive started to disappear.
Joshua also described the strain of carrying that stage. You put on a brave face, tell the story, get people fired up, then go to bed wondering whether you’re losing your mind. He joked that building the business took 10 years off his life.
You can be exhausted. The company can take too much from the person leading it. The role can become one you want, without wanting to perform it every day.
Joshua eventually recognised that he was a zero-to-100 founder. He wasn’t the person who wanted to take a company from $100 million to $10 billion.
That kind of self-knowledge is rare because founder culture rewards the opposite instinct. You keep going and keep telling yourself that stepping aside would look like defeat.
Sometimes the honest answer is that the company has outgrown the work you’re best at.
Scale is a different company
That doesn’t mean the founder failed. It means the company changed.
At some point, you have to ask whether you still want the job that comes with the next stage.
The old company may have to break for the next one to exist. The harder part is that it can break something in you too.
You can chase scale as the reward for building well, then realise it’s given you a company that needs a version of you that was never really yours.
That’s the cost you don’t always see until you’ve already built the thing you thought you wanted.
The company I currently work at is definitely at the scale up point. Went from 18 to 62 in the last 18 months. The first half of this article was a day in my life and the second half was pure alpha! Great piece, and I will for sure pick some of the tips up at work as well.
Scaling doesn’t just change the business, it changes your relationship to the work, and sometimes that’s the hardest adjustment of all.