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We are now almost fully booked for Summer 2024 and expect to close registration in the next few days.

We are now almost fully booked for Summer 2024 and expect to close registration in the next few days.

A Day in the Life of an Entrepreneur

19 September 2021

A Day in the Life of an Entrepreneur: Taking the Plunge


The rise of the entrepreneur in recent years has become impossible to ignore. 

Startups and small businesses seem to be popping up left, right and centre; even a global pandemic couldn’t quell people’s entrepreneurial spirit. According to the Centre for Entrepreneurs, a record number of new businesses were started in June 2020, increasing 47% on the year before. 

It’s easy to see the appeal. A career as an entrepreneur offers the chance to build something you’re really passionate about, to work to your own schedule and to be your own boss. 

But is there more to it than that? 

We sat down with Leona Mondsee, entrepreneur, CFO and all-around high flyer, to understand what running a business is really like. 

With several years’ experience in the burgeoning Fintech industry, Leona’s career has taken her from accounting to CFO at a range of startups. She is now CFO of not one but two companies, and has used her accumulated knowledge to co-found Reitly, an investment comparison platform. Reitly was set up to provide people with a free and accessible way to invest in property and improve their financial literacy. 

It’s a cause that Leona is very passionate about. In fact, during our interview, it was her energy and enthusiasm that stood out above all else.

Aspiring entrepreneurs take note: passion is essential, and a good work ethic won’t hurt either…

This interview has been lightly edited for length and clarity.

What does a typical day in your working life look like?

Sometimes it can be quite intense, but I love it.

There are days when I take breaks and get outside but there are also days where I’ll be working until 10 o’clock. 

I tend to try and dedicate the first half of my day to admin tasks; it’s very rewarding that way. I like to empty my inbox and get any tasks that I have to do out of the way so I feel I’ve made progress. 

Then the later half of the day might be dedicated to content marketing, product development, talking to customers... any problems that have arisen. This takes time and can lead to frustration: you may discover things which aren’t quite how you hoped they’d be. Sometimes problems arise and you end up asking more questions than you answer. 

For me, I prefer to deal with all that in the afternoon because I’ve then got the freedom to work through it for the rest of the day without worrying about a mountain of tasks I still have to do. 

What first inspired you to become an entrepreneur?

I actually never thought I would be an entrepreneur, I thought I was going to be an astronaut for a while!

However, I ended up training as an accountant. I didn’t go to university and after I left school I started working for a big, American multinational hospital group. They had hundreds of accountants and we all worked in this big office. I thought that was for me, that I was going to climb the corporate ladder and work for a big multinational company and it would all be really exciting. 

But it got to a point where getting promoted started to look increasingly difficult. People at the company were happy, often staying in their jobs for life but I’m quite impatient; I get bored easily and like to make progress. 

Working there I was constantly seeing stuff I wanted to improve and finding it difficult to push the change through. I’d want to change policy or procedure and it would take 6 months to get it signed off because there were all these different people it had to go through. I found that frustrating. 

Then a friend put me in touch with an old employer of hers who worked at a startup looking to do an international expansion. They were looking for a new global head of finance. 

That was my first ‘dipping the toe’ into the startup world, an experience that eventually led to me starting my own. Everyone wore jeans, there were Play Stations in the office and it was a really nice, friendly environment. I fell in love with it. 

I love the mystery, the unknown, the potential of what could be. That’s what drives me.

What’s the best thing about your job?

The thing that I like the most is that I can innovate and get stuff done. 

When, at my first startup, I wanted to automate the way we billed our clients (which took about a day and wasted a lot of time), [my bosses] said ‘do you want a developer for the day? If you can explain how to do it, they'll build it - job done!’. I was hooked. It was fast-paced, intense, demanding and I had the freedom to make a difference. 

After that it was an easy step to say, ‘okay I want to do my own thing. I’ve had enough experience working in startups, growing them, taking them from A to B. I want to give it a go myself’. 

And it’s been really exciting. Sometimes things don’t work out the way you expect but you love it anyway. You love the failures, you love the success and the stresses. Coronavirus affected my company very negatively, but I don’t regret it, because it made me and my co-founder step back and say ‘okay, how do we respond to this?’. And that’s what spawned the new product that we’re working on. 

What’s the hardest thing?

That friends and family aren’t living the life that you’re choosing to live, and that often they don’t understand it, either. 

When I decided that I wanted to give up my job and start my own thing a lot of people didn’t understand why. Why would I give up such a high paying role to make no money, and potentially be without money for a long time? Because statistically, as they say, 9 out of 10 startups fail. The one that does make it may not even be successful, it might only just break even.

They also don't understand why I willingly work 13 or 14 hour days, or work at weekends. They don’t get why I like such a high stress environment, or take my laptop on holiday. 

But I love it, I genuinely love it. I love the mystery, the unknown, the potential of what could be. That’s what drives me. 

What has been your biggest achievement since becoming an entrepreneur?

Taking the jump! 

Deciding to quit my job and just go for it. That was huge for me. It’s the scariest and the hardest thing I've ever done, but it’s also the most fulfilling. 

I didn’t want to be someone who looked back and had regrets. 

My advice would be to talk to as many people as you can and genuinely listen to what they have to say. Most founders don’t spend enough time listening to their customers.

How did you find your first 12 months in the field?

I loved it. 

Because I was trying to find my way, I did all sorts: I did secretarial jobs, I worked in the city for a bit, I worked as an analyst (which is where I learnt to love spreadsheets!).

I loved being around people and soaking up everything I could. I’m very much a sponge: wherever I am I want to learn everything about that environment or field.

The key thing I learnt in that time was that people are extremely generous. When you ask someone for help - for their opinion or some piece of knowledge - they will almost always go out of their way to share that with you. If I were to say to my financial director, ‘what do you do in your job?’, he would say ‘do you want to spend a day shadowing me?’ or ‘I’m doing some reports right now, shall I show you?’. 

I loved that; it taught me to always ask questions. That would be my secret power tip: ask other people. That has got me so far as an entrepreneur.


What are your hobbies and interests outside of work?

(Laughs) I’m super boring!

I like horse riding, but other than that I’m really into what I do. Even if I’m just relaxing at home I’ll be reading a book about something to do with my career. 

Back in the day when travel was a thing I went to South Korea - I was invited as a guest on behalf of the Korean government - to talk about encouraging women to go into entrepreneurship.

I like to get involved in technology events, too. I go to hackathons and meet-ups where we talk about machine learning. I know nothing about it, but I like to go and talk to people and learn as much as I can!

Do you have any advice for young people thinking about becoming an entrepreneur?

My advice would be to talk to as many people as you can and genuinely listen to what they have to say. 

Most founders don’t spend enough time listening to their customers. It doesn’t even  have to be your customers. We show what we do to anyone who will listen! It might be a piece of the product, marketing content (a slogan or email) or a landing page

There’s a really good book called ‘The Mom Test’, which talks about how, if you ask your mum ‘do you like my website?’, she’ll most likely say ‘yes, it’s great’. That feedback isn’t going to tell you why people aren’t buying your product. Whereas if you ask ‘tell me what you think this might do’ or ‘what do you expect here?’ or ‘how would you use that?’, you’re going to get far more insight. 

It’s important to take on negative feedback, too. I understand it hurts, but you’ve got to get to a point where you don’t even feel it. You want to ask ‘okay, why do you think that?’, and ‘how can I get around that issue?’ rather than feeling offended or thinking ‘what do you know?’. There could be some gold dust in that negative feedback. 

I think, overall, that’s the difference between being a successful entrepreneur and an unsuccessful entrepreneur: being able to take on feedback, accept criticism and learn from it.


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