How did she do that? Amy Woodside on founding mentoring site OKREAL

4 January 2018
By Fashion Quarterly


Amy Woodside has created a dynamic and inspirational community of women through her website, OKREAL.

While considering her next career move, the New Zealander noticed a gap in the market of relevant female-focused content and communities, and saw this as an opportunity to start asking women about their lives and the things they have learned. OKREAL was born and Amy began interviewing a range of inspirational woman. Today, OKREAL is based in New York and hosts events, panels and workshops for like-minded women to meet, grow and be inspired.

We caught up with Amy to ask her some questions about her journey, OKREAL and the life hacks she’s picked up so far.

What did you want to be when you grew up?
A pop star. What can I say, it was the 90s…

What single book, film or album has had the greatest impact on you? Why?
The books I read when I was young, like Little Women and Little House On The Prairie.I loved reading about the lives of other girls and women. 20 years later, it’s what I’ve built my business around, so it’s all come full circle.

When do you go to bed and when do you get up?
Before 11pm, if I can, and I usually wake up between 6am and 7am. This will likely change with my son arriving soon.

Can you explain your career path to date?
I studied Communications at AUT, then worked at Ogilvy for a year out of uni. I left New Zealand at 22 and moved to Toronto, and worked about three jobs to pay rent—as a bartender, a waitress, and in retail. After six months in Toronto I moved to New York City. While I waited for my visa to come through, I worked as a nanny and created a jewellery brand to make ends meet. As soon as I got my green card, I got a job as a project manager in a branding agency, which is where I learned how creative businesses work in New York. After a year there, I went freelance in operations management and worked on the side as an artist, and decided I was going to start my own business. I wanted to do something that married my experience in the creative and business worlds, and build something that I thought was missing. It was late 2014, and at the time, there weren’t a whole lot of women-focused communities that were hosting events, or online platforms that spoke to me in a way that felt relevant and down to earth. So I set out to create a curation of wisdom shared by strong, smart women, and OKREAL grew from there. We started as a digital platform, and now in addition to online content, we host panels, weekly mentor circles, and do one on one coaching.

What’s it like being an New Zealander living in New York City?
Being born in New Zealand was my biggest stroke of luck and moving to New York City has been my best decision to date. I moved to NY at the end of 2009 and feel privileged to call two of the best places in the world home. New York can have a glamorous appeal if you’re looking from the outside in—but the reality of living here is very different to what you might see on Instagram, or if you come here on holiday. It is a grind—but one that you have to be grateful for. The only way I’ve been able to maintain my sanity while building a startup in NY is to return to New Zealand once a year to see my family and get some sunshine and beach swims in. Both places give me different things I need: New York keeps me driven, fuels my ambition, makes me work hard—while New Zealand keeps me grounded, restores my sense of peace, and keeps my tan in check!

What is the biggest obstacle you’ve overcome with OKREAL?
Developing it into a profitable business. There is no blueprint for making this kind of business work—I’ve learned (and am still learning) through trial and error.

What motivates you?
I love my work, so I’m never not motivated. Sure, there are days that are not enjoyable, but it’s all part of it.

What do you wish you’d known at the start of your career?
That it’s going to take ten times as long and ten times as much money as you think. That people can guide you, but no-one else can do it for you. That it’s not just about seeing opportunity and working for it, it’s about creating opportunity when it doesn’t exist. That no matter how nice you are, you are going to face conflict with people. That you need a good accountant from day one. That most reasons for ‘why you can’t’ achieve something are just excuses. That if you want something bad enough you can make it happen.

What do you believe has been the key to OKREAL’s success?
Hard work and perseverance.

What is your life motto?
Get on with it.

What is the best advice you’ve ever been given?
“You don’t have a career, you have a life.” —Cheryl Strayed

Who do you most admire in business? Why?
I have a lot of admiration for my girls Audrey Gelman and Lauren Kassan, who founded The Wing. They have created the most incredible spaces for women in New York (and soon to be, [Washington] DC). To have seen it grow from a miniature cardboard concept in mid-2016 to what it is now has been so impressive. The Wing has been my haven over the past year and I know a lot of women who share this sentiment.

What do you believe is the secret of success? 
I don’t think there is one, and success is so subjective—I think more in terms of fulfilment. Fulfilment is about being really honest with yourself about what you need, then doing whatever it takes to create that for yourself. It looks different for everyone. This is ultimately why I created OKREAL: as a resource to help women figure out what their version of fulfilment looks like, and how to get there.


Who do you turn to when the going gets tough?
My mum.

You have already achieved so much with OKREAL, but what’s next for you?
Being a mum myself!

Amy Woodside // @ameohmy

Interview: Ella Francis
Photos: OKREAL & Instagram.


Sign up & Join
FQ Insider

Unlock exclusive content, behind-the-scenes insights, and special offers by becoming an FQ Insider.

Fashion Quarterly Winter 2023 Cover
Fashion Quarterly Winter 2023 Cover

Sign up & Join
FQ Insider

Unlock exclusive content, behind-the-scenes insights, and special offers by becoming an FQ Insider.

Sign up to the Fashion Quarterly newsletter.

*Ts&Cs apply.
Find out more at