Ten Terrifying Questions with Rebekah Campbell!

by |September 8, 2021
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Rebekah Campbell is the co-founder of Hey You, a mobile app used by more than one million Australians to order and pay at cafes. She has kept a blog about her experiences as an entrepreneur which was named ‘Best Business Blog’ by Smart Company and became a New York Times column in 2012. Rebekah writes a monthly opinion piece for AFR BOSS Magazine and has contributed to MamaMia, Women’s Agenda and Stuff. She is a high-profile public speaker who spoke at TEDx Sydney and numerous events for Business Chicks. Rebekah was named a Woman of Influence in 2015 and APEC Young Woman Innovator. She is currently the host and curator of the City of Sydney’s virtual event series ‘Reboot’, supporting 18,000 Sydney business owners to recover from the impact of COVID 19. Rebekah’s personal passion is her everything, which she finds at the end of her book, a memoir called 138 Dates.

Today, Rebekah Campbell is on the blog to take on our Ten Terrifying Questions! Read on …


Rebekah Campbell

Rebekah Campbell

1. To begin with why don’t you tell us a little bit about yourself – where were you born? Raised? Schooled?

I was born in Scotland and we emigrated to New Zealand when I was three years old. I had a pretty ordinary Kiwi upbringing living on the outskirts of Whangarei and then next to farmlands in Wellington. I was an only child and spent a lot of time wondering the hills by myself which got me thinking and forming opinions on things. I studied Politics, Physics and Te Reo Maori at Victoria University in Wellington (weird and quite useless combination of subjects I was interested in) and moved to Sydney when I was twenty-one to work as a manager for Bardot in the first Popstars series (not at all related to my degree!).

2. What did you want to be when you were twelve, eighteen and thirty? And why?

At age 12 we had to do a school project on what we wanted to be when we grew up and interview someone from that profession. I chose ‘Prime Minister’ because it was obviously the top job. I called up the PM’s office in Wellington and secured an interview with the then PM David Lange. I remember him telling me he wished he’d learnt more about finance before politics which got me thinking about business.

At age 18 I wanted to be an entrepreneur because I’d get to work in lots of different industries and didn’t have to choose just one direction.

At age 30 I’d built a large independent music company representing artists such as Evermore, Matt Corby, Lisa Mitchell, Alex Lloyd, Katie Noonan and several others. I’d worked out that I didn’t want to still be going to gigs in my ’40s so I’d start to think about building starting a technology business. I built two tech companies (Posse and Hey You) and at age 40 decided to return to what I originally wanted to be at age 8 (before the start of my answer to this question), which was to be a writer.

3. What strongly held belief did you have at eighteen that you don’t have now?

At age 18 I had a huge amount of ambition and energy. I believed that becoming successful was the most important thing and that I should do ‘whatever it takes’ to achieve my goals. That was my motto! Now in my early 40’s with a young family, I can see life with much more perspective. People and relationships are the most important thing and should be valued above everything else.

4. What are three works of art – this could be a book, painting, piece of music, film, etc – that influenced your development as a writer?

As I said before, I spent many years working in the music industry and music is central to my life. A lot of music isn’t about words, it’s about creating emotion, a feeling when you listen to a record. Coldplay’s ‘A Rush of Blood to the Head’ album is a great example of this. The lyrics are mostly meaningless, but the music makes me feel like my heart is tugging out of my chest. As I wrote my book it was important to me that each scene had a feeling, so I chose a song or album and blasted it before and often during my writing. Coldplay was a big influence, also U2’s ‘One Tree Hill’ as I wrote about death, ‘The Arcade Fire’ as I wrote more sexy scenes in New York, Etta James for the scene when I met my husband. Writers have less tools to evoke emotion (no instruments) but I still think it’s possible to create atmosphere using pace and rhythm in the words.

I’ve always been a fan of Aaron Sorkin’s screenplays – particularly The West Wing. I love that the best stories and conversations often happen as the characters are getting ready for an event, like preparing for the State of the Union address. Then the episode barely shows the actual event at all – it’s often just alluded to. I used this idea writing my book. For example, there’s a fun story as I’m sitting outside the Westpac board meeting waiting to present. All the top executives are sitting around chatting with each other while they wait to be called. I don’t actually talk about the presentation – just what happened outside as we waited.

One of my favourite books at the time of writing was Three Women by Lisa Taddeo. I loved how intimate her characters were, I felt like I inhabited their brains as I read their stories. I chose to write in the present tense so I could share every honest feeling, insecurity, judgement and question I had during the time I was writing about. Even when they were embarrassing or flawed.

5. Considering the many artistic forms out there, what appeals to you about writing non-fiction?

I like real stories. When I sit down to watch a movie I always search for ‘films based on real events’. I don’t watch documentaries for fun – only to learn. But I love a re-enactment of story that actually happened.

I chose to write my book in a similar style. I read lots of other memoirs and noticed the ‘documentary’ style wasn’t as fun as some of the fiction I was reading. Even though the lessons I could pull from the memoirs were quite useful, I often found myself not finishing the books because I didn’t feel like I needed to know what happened – it was obvious.

I’ve written my story like a movie based on real events as opposed to documentary style like a more typical memoir. I found this approach much more fun to write and I hope that I’ve managed to create emotional peaks and suspense much like a fictional novel.


“It was obvious to me that what brought me the most joy, what I was most grateful for and what I was most proud of myself for creating wasn’t a business, it was my relationship and my family.”


6. Please tell us about your latest book!

138 Dates is a very personal story about my search for love and happiness. I’ve spent most of my career as an entrepreneur and I was approached by a publisher to write a business book in 2017. I’d recently left my business ‘Hey You’ and was pregnant with our second child. I started work on the book, but every morning as I sat at the keyboard, something felt wrong. I wasn’t excited to share my stories and I questioned how much value I was creating for the world. Was this the best use of my talents? 30,000 words in, I hit delete.

It was obvious to me that what brought me the most joy, what I was most grateful for and what I was most proud of myself for creating wasn’t a business, it was my relationship and my family. They were, and are, everything.

And they didn’t come easily. At 34 and a half, I hadn’t been on a date in ten years after my first boyfriend was tragically killed in a car accident. Then on Christmas morning 2011, I woke up on a fold-out bed in the garage of my parent’s friend’s house and made a resolution – one date every week for a year.

What followed was 138 Dates (yes 138 different men) across Sydney, New York and San Francisco, at the same time as launching my tech startup Posse.com (now Hey You) and writing a high-profile newspaper column. Along the way I met some incredible friends including an awesome psychologist and Canva’s Melanie Perkins, who gave me advice that I applied to building the business and to finding a relationship. I kept notes in a journal and many of these lists and lessons appear in the book.

7. What do you hope people take away with them after reading your work?

I hope that 138 Dates is useful to everyone who is either in a relationship or is looking for a relationship. I hope it makes readers laugh and cry and I hope people can relate to some of the stories. There is nothing more valuable that I can give than everything I learnt during this very intense period of my life. My heart is on the pages!

8. Who do you most admire in the writing world and why?

Now that I’ve written a book, I have a huge amount of respect for anyone who finishes a book. It is a massive task – so much harder than I imagined when I started. There were moments when I thought I was wasting my time and other times when I feared that I’d humiliate myself by putting all these personal stories out there.

9. Many artists set themselves very ambitious goals. What are yours?

The only way I managed to keep myself writing through those periods of intense doubt was to imagine a reader. For me, it was my friend Jen who is 35 years old and hopes to find a partner and have children. I wrote this book for her, and for anyone else who finds themselves with the same hopes and fears that I had in my thirties.

Of course, I hope my book has broad appeal, I hope as many people as possible are touched by the stories as possible. But when I was writing I tried not to imagine selling hundreds of thousands of copies because every time I did my head would fill with the reality of book sales. So, I reminded myself that if I could impact just one person, if I could provide her with some insights, some encouragement and a sense of not being alone, then it’ll all be worth it.

10. Do you have any advice for aspiring writers?

Definitely imagining a single reader helped a lot. Three more pieces of advice I’d give:

Do a writing course. I did several courses with the Australian Writers Centre which I found incredibly helpful. There’s a lot of technical stuff like how to write an impactful scene, how to create pace, build to a climax etc which I didn’t know and helped me craft my story. It also gave me a structure to start, regular deadlines to submit work and feedback from peers and from a teacher.

I initially wrote 140,000 words and wasn’t sure how to cut. Someone told me to write a single sentence describing what the book is about and cut anything that doesn’t fit into the description. I pasted this sentence onto the top of my computer screen as I edited and it was super helpful, especially for memoir because I’d written lots of backstory about growing up and my early career and it became clear that none of it fitted into this story. It felt so amazing to cut even when some great sentences and funny stories didn’t make it in. It helped me craft a much punchier book.

After I’d been writing for two months, I felt frustrated by how slowly my life was progressing. I had nothing to post on social media, I wasn’t out there doing events. I worried people would forget that I existed! I wanted to speed up, so I increased my writing target to 3000 words per day. It didn’t work – I kept getting frustrated with myself for not hitting my goal or for writing rubbish, so I’d give up and not make any progress at all. I remember reading my four-year-old daughter the story of The Tortoise and the Hare and I woke up the next morning imagining myself as the tortoise. I agreed with myself to write 1000 good words every day which seemed very slow at the time. But at the end of each month I was stoked with how far I’d come. And it turns out that no one cares if you disappear for 18 months. Everyone is way too busy doing their own thing to notice!

Thank you for playing!

138 Dates by Rebekah Campbell (Allen & Unwin) is out now.

138 Datesby Rebekah Campbell

138 Dates

The true story of one woman's search for everything

by Rebekah Campbell

On the outside, Rebekah Campbell has an enviable life. She is founder of hot Sydney startup Posse.com, writes a popular blog and gives inspirational talks at conferences for female entrepreneurs.

But when she turns off the light each night, she is alone and terrified of the future. She knows that what's important to her isn't money or startup glory or social media followers. She wants love. She wants a family. And she is stuck...

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