How do you start your first startup? My brother just sent me this photo from 1987 - exactly 30 years ago - of me and my very first business when I was 18 years old: Selling prints on the streets of Cambridge.

Over the last year I’ve posted many entrepreneur stories on Facebook, and I’ve been asked to share some stories on my own journey. So here’s the story of starting my first startup:

How did the business start? It didn’t start from opportunity, but from necessity.

At the end of my 1st year of Architecture studies, my Director of Studies told me that unless I spend the summer adding to my portfolio, I would likely fail to make it to my 2nd year. I had been so busy rowing and partying that I was a long way behind in the work I should have done.

But that wasn’t my biggest dilemma. All my friends were planning a trip to Greece in August and had lined up jobs in July to pay for it - as they all had contacts in London. I was the foreigner, with my parents in Hong Kong, so I had no job lined up.

No job, no money. No money, no Greece.

And if that wasn’t enough, I really wanted to make the rowing crew in the second year. But to do that, I’d need to spend two weeks in July on rowing camp in Cambridge, with early morning rows every day.

As everyone was celebrating in the college pub in the last week of term, I sat in the corner feeling sorry for myself, with no idea what I was going to do. A friend sat down next to me and said: “What’s the problem?”

“I’ve got plenty of them. Which one do you want to hear about?”

He laughed and said “The one you want to solve”

“I want to solve all of them.” I replied. Then I asked “How do I spend the summer filling up my portfolio with prints?”

Before he could reply, I then said “I can’t. Not if I want to get a job in London and go to Greece.”

And again before he could say anything I said “And I’m going to have to give up on the rowing if I want to do that.”

It took a few more drinks and increasingly creative suggestions from him - matched by increasing resistance from me - before he said “Maybe you’ve got this all wrong. You’ve got too many small problems instead of one big problem. That’s why you can’t solve anything.”

In an ‘aha’ moment, I tried turning all my different questions into one big question, and came up with:

“How can I go to rowing camp while creating artwork for my portfolio that makes me enough money to go to Greece?”

That was it!

Over the next three days I went to Cambridge’s three most famous college chapels (King’s, Trinity & St John’s) and drew all three in black and white and on A3 paper (so I could easily photocopy them).

I then went to Ryman’s and bought a box of A4 paper, then to Sainsbury’s and bought freezer bags to put the prints in, then to Kall-Kwik and got the three prints photocopied. Total cost: £35.

On the fourth day, I went to rowing camp in the morning, then sat in Trinity Street (where most of the tourists passed by) and put up a board (the one in the photo) that said “Cambridge College Chapels by R. Hamilton, Architecture Student at Trinity College. Prints £2 only. £5 for 3." As I sold my prints, I drew a new picture and at the end of the day, I made prints of that too.

At the end of the first day, I had made £50. I worked out ways to test, measure and optimize my hourly takings (who would have thought asking people for the time would make them stop which made others stop and double hourly sales?) and on the second day I made £100, which then grew to £200 by the third day.

By the end of the first week I had made more than my friends were making in their 9 to 5 London jobs in a month. By changing location each day, by the end of the second week I had filled my portfolio with original drawings - and I’ve been an entrepreneur ever since.

I’ve had many ups and downs over the years, and the numbers have gone from hundreds to thousands to millions. But the thrill of earning that first £50 from my own initiative is what starting startups is all about.

So if you’re just getting started, keep at it, because the journey is worth it.

And whenever it seems you’re trying to solve too many problems at the same time, try combining them all into one big problem worth solving.

“Necessity is the mother of invention” ~ Plato

As well as getting the entrepreneurial bug, I did end up on the rowing camp, going to Greece and getting my Architecture degree. And those drawings led to my first business after college, Cityscapes: Pictorial maps (beginning with Cambridge) of the entire city from above, with shops paying to have their logos on their rooftops.

And the 18 year old girl sitting beside me? That’s Renate, who became my girlfriend and then wife for the next 30 years…

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