Dana Denis-Smith, founder and CEO of Obelisk Support

In our regular series, industry big wigs take us back to their first jobs


Hi, Dana! Who are you and what do you do?

I’m Dana and I’m founder and CEO of Obelisk Support. We have been working with big enterprise clients and high growth companies supporting them with flexible and affordable legal services for the past 11 years. All our lawyers have been mainly working remotely from the start, as many quit their jobs because they could not juggle work and family commitments.

What was your #MyFirstMcJob?

I spent my childhood in Transylvania, in central Romania, under communism. There were no McDonald’s or even supermarkets to cut your teeth in as a keen teenager wanting to earn some pocket money, so it was hard to show your entrepreneurial spirit! We had a big apple orchard in our garden and my mum worked in a factory, making plastic bags. So I would stand outside the factory with a bucket and try to sell these amazing red apples to the workers going in and out of shifts. It went well until I encountered my competition. My neighbour — who was also about 11 — started standing outside the factory with a bucket of yellow apples, so I had to start up being more proactive to get my apples snatched up. It turned out to be more effort than I originally planned.

Whose apples were best?

The red apples were crispier and had a lot more personality. Red is my colour which might explain why even today my whole company brand is red — including the logo. The yellow ones were softer, more like a pear. Mine were definitely the best!

How much did you sell?

The factory was only five minutes’ walk away, but, as I was a child, I could only carry one bucket-full of apples. I sold them by the fist-full, a little bit like you see on market days in the UK. The average factory worker would have earned about 1,500 old Romanian lei a month. I probably earned about 10 Romanian lei per bucket

What did you spend your first pay cheque on?

Because of communism, everything was pretty bleak, including the clothes that were all navy, brown and grey. I saw this pink and white top and was so overwhelmed by the colours, I just had to have it. So on top of the apple business, I decided to recycle empty glass jars, which you could return for money. There’s only so many glass jars your parents have, so I also went to collect some from my neighbours. Everybody was very friendly … here’s one jar, two jars … but one neighbour had this angry dog that almost ate me! But I did manage to eventually buy my top.

What skills did you learn that you still use today?

Not to fear numbers. When I first came to London 25+ years ago, to go to LSE [London School of Economics], people still went: “I don’t do maths”. Not being good at maths was like a badge of honour and it really puzzled me that there was so much dislike for the subject. I guess I learned to come up with ideas and follow them through. The regime in Romania as I was growing up was pretty nasty, so you had to be imaginative and creative to survive.

Are you still in contact with any of your old colleagues?

Well, I’m not in contact with my competitor, the seller of the yellow apples, as his family emigrated to Germany just as communism collapsed! But I am still in contact with the generous neighbours who gave me their jars. I recently returned to visit my old Romanian high school because they had applied to get college status and they needed to feature some alumni to back their application. They chose to feature me which was very humbling and I was thrilled their application got through.

Why is alumni so important to you personally?

Starting from scratch in a different country means you have to collect friends through your university or job alumni. I’ve stayed in touch with many people I studied and worked with and have become life-long friends. We have so many shared experiences, ups and downs, that make our friendship stronger.

What would happen if you went back and tried to sell apples today?

I’d have no one to sell them to, because the factory closed down! So I’d need to find another factory or come up with a different distribution strategy. Also, I’m not sure if apples grow in our garden any more in that quantity. I’ve got a product problem and a customer problem, so I would be in a right pickle!

What advice would you give your younger self?

Don’t be afraid to try new stuff. I didn’t have anyone entrepreneurial in my family as a role model, so it never crossed my mind that I’d be an entrepreneur. Even when I tried selling apples, I thought: what’s the worst that can happen? Sometimes also you think you really want something — take the pink and white top I saved up for. It was dreadful, and became pyjamas straight away. I don’t even like pink! But the process of ‘fundraising’ to get the top was super educational so it was worth it, despite the outcome.




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