People Business » Breaking the Glass Ceiling: Holly Mackay of

How I made it to the top

I was brought up by a Scottish accountant and a self-starter with Derbyshire roots so it’s no surprise that the title of this piece makes me immediately uncomfortable. I am certainly not one of the new entrepreneurial generation who loves telling everyone how they meditate 12 times before breakfast before embarking on conference calls with New York, high fiving their agile developers and kissing their perfect children!

That said I did build and sell a business to a publishing firm in 2012 within three years of establishment, completing a successful three-year earn out in 2015. And am currently almost three years in to building my latest baby, Boring Money. So if this counts as the top, here are some reflections on how I got here.

What’s the formula

I’ve often wondered about this and the splits below are not precise. What I will say is that plain and simple hard work, really thinking about what your customers want and then having that final sprinkle of ‘fairy dust’ that makes you unique are a pretty powerful combo.

50% hard work
15% knowing my subject inside out
15% making friends in my industry
15% timing and luck
5% being different

Embrace being different

I didn’t do the right degree for my field. That said, I read modern languages at Oxford so I wasn’t coming from Struggle Street but I did come from Set 4 in maths to work in the world of finance. The first factor I’d highlight is being different. With your ideas, your skills and your personality. Now that I am a confident, extrovert senior figure, being a woman helps. It makes me different in a sea of grey-haired male commentators in their pinstripe suits. Also being someone visual who loves words in an industry full of mathematicians and engineers is great. Diversity is as much about brain types as it is about gender.

As well as thinking about your personal differences, think about your products and services. What is it that makes you different from the competition? Summarise it in three bullet points. Don’t over-complicate it. And come back to it regularly. I think this applies as much to bigger businesses as to start-ups. Are you still doing what you should be doing and what new tech will let you do?

Make friends – people do business with people they like

I came back from Australia aged 30 after a broken relationship with no work contacts, no house and not much money, but I had no ties so could go out in the evenings and socialise. The investment industry is generally full of people who are great fun and I was at the opening of an envelope.

The other thing I see is short term greed. That kills businesses, so think long term. Make your clients happy and g0o the extra mile. Give them a present if they speak at a conference. Small personal gifts and handwritten cards mean more that a corporate email or a boring corporate gift which no-one really wants anyway.

Know your stuff

If you stick your head above the parapet people will throw stones. Your shield is your knowledge. I do think this applies more to woman than to men still. You can only really disrupt a world you understand. Shouting will get you so far but if you are constructive in your criticism and help to shape the solution, not just bleat about the problems, you will gain respect and have true influence.

“Your shield is your knowledge. I do think this applies more to woman than to men still. You can only really disrupt a world you understand.”

Hard work

This is the boring one. Life is a bit like a pie chart with friends, family, work, home and play. We only have 100% to play with. Some of these slices are set in stone during particular life chapters as I found out when I had my first baby. For the last three years, my pie chart has been work and children. I miss my friends. But life goes in chapters and that’s the one I’m in right now. I work weekends, nights and in between. You have to pick up the pieces in the early years of a business.

At the end of the day delivering a great service is down to dotting the i’s and crossing the t’s. People tie themselves in knots about non-disclosure agreements and patents and the like. It depends what your product is but I think the idea is way secondary to the execution. I’m never too worried about sharing ideas as I know it mostly comes down to the attention to detail in rolling up your sleeves and getting it done.

Timing and luck

I think luck is over-rated. We make our own luck with a small dollop thrown in at times. My real luck has come from meeting kind, wiser, older supporters who have guided me along the way with skill, humour, generosity and plenty of wine. I had a fabulous friend Paul Bradshaw who guided me for years and was my first shareholder in Boring Money. I’m not sure I could have done it without his encouragement. I don’t think that we can contrive finding these mentors. But grab them when they come along!


Holly Mackay is the founder and CEO of, a personal finance advice website which aims to help ‘normal people’ to make sensible decisions about saving and investing.