The jump from “me, on my own, in a van” to “two of us, in two vans” is one of the hardest in any trade. It looks like it should double your revenue. It often halves your sanity instead. The mistakes I made were avoidable, but only with hindsight. So here’s the hindsight, free of charge.

Mistake one: I hired before the systems were ready

I hired Tom, my first apprentice, when I was already too busy. The plan was that he’d take some weight off and I’d train him in the gaps. What actually happened was I got busier, not less, because now I had to manage him and keep doing the work.

The systems that work for one person — paper diary, mental notes, jobs that live in your head — collapse instantly with two. You suddenly need: a way to share who’s doing which job, a way to track materials across two vans, a way to book in jobs without double-booking, a way to invoice for work the other person did.

If I were doing it again, I’d put the systems in first. Even before the second van rolls. Set up the job tracker, the shared schedule, the materials log, the photo upload to each job — all of it — and live with it for a month while I’m still solo. Then when the new person starts, the rails are already there.

Mistake two: I didn’t define what success looked like for them

For the first three months, Tom thought he was doing well. I thought he was barely keeping up. Neither of us had ever talked about what “doing well” actually meant.

What success looked like in my head was: jobs completed on time, materials not wasted, customers happy, photos uploaded to the system.

What success looked like in his head was: turned up on time, didn’t break anything, asked questions when he didn’t understand.

Both are valid. They’re just very different bars. The fix would have been a ten-minute conversation in week one. Without it, I was constantly disappointed and he was constantly confused about why.

Mistake three: I tried to be the same kind of boss I’d had

My old boss managed by walking around, shouting occasionally, and telling you off if you got something wrong. It worked. People knew where they stood. So I tried that, in a much smaller, less natural-to-me way, and it was awful for everyone.

Tom isn’t me at twenty-two. The trades have changed. Workforce expectations have changed. The “old school” management style was driving him to look for another job within four months.

What works now: regular short check-ins. Praise for things done well, specifically. Corrections delivered in private, with reasons attached. Clear expectations on the practical stuff (start time, what to do if a customer’s not in, how to handle damage) so the rest can be conversational.

Mistake four: I didn’t price up properly for two

For about six months, the second van made me less money than working alone. The reason was simple: my pricing was based on what I, working alone, could charge. When Tom was on a job, I was paying him while still charging the same job rate I’d have charged on my own.

The maths only works if either: (a) the second van means you can take twice the jobs, or (b) you raise your rates to reflect the higher capacity. I tried to do (a) without doing (b), and we just ran ragged at the same revenue.

When I finally raised rates by 18%, three things happened. We lost a few of our cheapest customers (good — they were the ones who took up disproportionate time anyway). The remaining customers paid more without complaint. And our margin per job finally became a margin worth having.

Mistake five: I didn’t track who was doing what

In the early days I’d say things like “Tom did the Mitchell job” and “I’ll do the rewire on Friday.” Mental notes. Then a month later I’d be trying to work out which customer to chase about which payment, and I had no record of who’d actually been on which job.

The fix is so simple: every job in the system has the assignee on it. Every photo, every note, every invoice line. The minute the system tracks who did what, you can answer questions like “how many jobs did Tom do this month?” and “what was the average ticket size for jobs he ran?” Without that, you’re flying blind.

What I’d say to someone about to do this

Three things, in order:

Set up your tools before you hire. Not after. Not “we’ll figure it out together.” Before.
Have the expectations conversation week one. Both ways — what they expect from you, what you expect from them.
Reprice. If you’re not changing your rates when you change your capacity, you’re just trading sanity for revenue you didn’t actually gain.

The leap is worth making. Two vans is a real business in a way that one van isn’t quite. But the path is steeper than it looks, and most of the difficulty is people-and-process, not the trade itself.

stedd.io is what I now use to run the two-van version of this.