Lessons by subject

Business lessons learned through experience

Startups, freelancing, partnerships, and failure. These are honest accounts of what happened, what changed, and what the writer knows now.

Latest business stories

HNDSYT Original4w ago

Business

The First Invoice With My Name On It

I sent my first invoice on a Sunday night.It was only for a small website job, but seeing my own name at the top made it feel serious. I had copied the payment terms from a template because I had no idea what I was supposed to write.The client replied, “Looks good.”Then nothing happened.A week passed.I kept checking my bank account and feeling awkward about sending a reminder. The work was finished, so in my head the difficult part was over.A friend asked, “Have you chased it?”“I don't want to seem difficult.”He laughed. “You are asking to be paid.”That was the first time I realised I had confused being easy to work with with being professional.I sent the reminder.The client paid the next day and apologised. He had simply forgotten.Now I put the payment date in writing before I start. I still don't enjoy chasing money, but I don't apologise for doing it either.

#business

The takeaway

Being clear about money is part of doing the work professionally, not a sign that you are difficult.

HNDSYT OriginalJul 21, 2026

Business

I hired for skills and fired for attitude, every time

You pick people up in this job, you talk. I ran a small minicab company on the side for about eight years, four drivers at the peak, dispatch through my wife. Everyone thinks the hard part is finding customers. It is not. The hard part is the guy who shows up late twice in a week and has a reason both times that you cannot really argue with. I had one driver, I will not say his name, came with references, clean licence, knew the borough better than I did. First interview he was sharp, answered everything, even asked about the pension setup which nobody ever asks. I remember thinking, right, this one is sorted. Hired him on the spot, which I had never done before. Felt good about it walking back to the car. Rain was coming in off the high street and I did not even bother with my hood.

Melbourne, AustraliaWhen it happened: 30-39#hiring #partnerships

The takeaway

I have hired probably thirty people over the years between the cabs and some other bits of work. The CV stuff, the interview stuff, that is all fine and you need it. But I kept learning the same thing and still hiring the same way. I do not fully understand why.

HNDSYT OriginalJul 21, 2026

Business

I kept a failing product alive out of pride

I'd been building this little app thing for about four months. Nobody was using it. My friend told me twice it probably wasn't going anywhere. I kept opening the same spreadsheet every Sunday night anyway.

Chicago, USAWhen it happened: 40-49#startups #pricing

The takeaway

I don't know if I learned much. Maybe that I can tell quite early when something isn't working and I just don't want to.

HNDSYT OriginalJul 20, 2026

Business

I scaled before the model actually worked

I moved to Berlin when I was twenty four. Came from a mid sized city in Brazil, spoke okay German, had some savings and an idea I had been turning over for about two years. The idea was a marketplace, B2B, connecting small manufacturers with logistics providers. Boring description but I genuinely believed in it, maybe too much. I had done some customer interviews, had a spreadsheet that looked fine, had one pilot customer who was paying a small monthly fee and seemed happy. The office I rented smelled like old carpet and whatever the previous tenant had been cooking. I remember thinking that was a good sign somehow, like it was a real place where real work happened. It probably just needed cleaning.

London, UKWhen it happened: 30-39#startups #finance

The takeaway

The unit economics were broken from the start, I just did not look at them properly. Or I looked and then looked away. Each new customer I was acquiring cost more to serve than they paid, and I had done the math in a way that assumed volume would fix that. Volume does not fix a per unit problem, it makes it bigger. I knew this in theory. I had read the blog posts. It is different when it is your own numbers on your own spreadsheet at eleven pm in a city where you moved to prove something to yourself. I think I was also scared that if I slowed down to actually fix the model I would have to admit it was not working yet, and I had told too many people it was working. Friends from back home, my parents, a few investors I had coffees with. Small lies that compound.