an interview with sian simpson

an interview with sian simpson

Sian Simpson is New Zealand's startup and innovation ambassador to the world. Buying a house on Waiheke, three family suicides, interviewing Helen Clark, biking 350 miles through Zambia, and living all around the world, she has gone through some amazing highs and some tough lows. We talk to her about both and get an insight into her life as a completely remote worker living between living in San Francisco, Australia, London, Paris and Singapore and Waiheke Island in a given year. 


How do explain what you do to strangers?

I work with entrepreneurs and business owners to help them grow and expand/export their businesses nationally but mainly internationally to global markets such as San Francisco/USA, Australia, UK, Canada, Europe & Singapore. 

I’m best thought as a combination of a concierge and a library - I connect you to what you want to know, and I have a library of useful knowledge from having worked with businesses big and small, and people all over the world for the last decade. 

I work across functions (marketing, sales, customer service/success, product management etc), across continents and my network/community is my superpower. 

I do this all online/virtually from anywhere in the world as long as I have the internet, a smart device and power. 

I typically split my time across San Francisco, New Zealand, Australia, London, Paris and Singapore in a given year. 



Where did you grow up and what was it like?

I was born at Takapuna hospital, at 4:06 am on 04/06/1991 (how spooky is that!). My family lived in Glenfield until I was 4, then we moved to a farm in Kaukapakapa for 5-10, then I spent the rest of my childhood/adolescence living in Mairangi Bay. 

I loved living on the farm it was so great, our property backed onto a reserve so we had three waterfalls in our backyard, I had a pet goat named pepper, I lived in my gumboots and would be either climbing trees, chasing my Dad around the farm or collecting cicada shells off the trees. I was a total tomboy. 

Growing up I spent a lot of time at Mum and Dads office as they were always working, they’d started their businesses when Dad was 18, he was an entrepreneur, so that was our second home really. I was a bit of a terror, always eating Milo straight out of the tin by spoonfuls, and my sister and I turned the attic into a fort for us to play in. I also (weirdly) spent a lot of time down the back of Dad’s office with our neighbours - one was a mechanic, the other was a panel beater, I always came back covered in dirt, oil and grime and would be gone for hours watching these old men pull things apart and put them back together! 

In 1999 my Dad sold his first business, New Zealand Security Services, he was from a poor family, so he took us out of school on a four month holiday around Asia and we lived in Italy for two months with my Mum’s great auntie. That was such a cool experience for me, I had my 9th birthday in Italy. It was the first time my Dad had been overseas. 

When we got home I took up ballroom dancing again and basically turned into a girlie-girl, I was excellent at ballet and also latin and ballroom, as well as netball and touch. Bit of an all rounder in the sports department. 

I was quite a spunky kid, super cheeky and always in trouble! I’ve always needed to know ‘why’ which drove most people mad! 


What does a normal day look like for you?

I don’t really have normal days, here are some! On a ‘work from home day’ I wake up, have my coffee straight away, check my emails, make breakfast either poached eggs on toast or fruit, yoghurt and gluten free oats, then I go for a walk on the beach, pick up a proper coffee, head home shower and get stuck into work and projects, usually some calls. Break for lunch. Work some more, I typically take a break around 5 or 6pm. Make dinner, finish work and then read/listen to music and in bed by 10pm. 

I go into the city three days a week, and to Wellington one of those days. I’m usually always hosting events, speaking at a conference or event, or to a corporate, meeting with startups and entrepreneurs or hosting international visitors. I also do a webinar every Thursday morning at 10am, I often joke about ‘waking and broadcasting’ we do these to build capability in our community. 

My year is pretty cyclic but I know what I am responsible for, make a plan for the week and just get it done. I’m super independent and autonomous. So set the strategy for the month or year and just execute on it. I just finished a 100 day sprint building our new website from scratch and building, launching and executing our 3 day conference too. It’s a lot of work for one person but super rewarding. Then I flew to Australia last Thursday to host a panel at IndieConf on building sustainable startup culture. 

I spend a lot of time building websites and community, and also produce a lot of content.  If I am travelling I do exactly the same thing but in a different place. 

When I’m on the road I’m rolling my rimowa carry on suitcase, and usually in my ‘chic activewear’ it’s a long standing joke with my friends! I’m often on the road, and I always carry my pillow with me, as a long-term sufferer of intense back and neck pain taking a pillow helps me have an amazing sleep wherever I am! I have friends and collaborators in most cities around the world so days can be spent meeting in random cities, hosting dinner parties, attending conferences, visiting innovative tech companies, helping governments with economic policy or sitting in a cafe drinking mulled wine and writing. Later this year I’m going to live in Paris for a month I’m super excited about that! 

When you were 15 what did you think you would be doing now?

I was super blonde when I was 15 (I went all natural at 21 for a couple years as part of learning what it meant to be beautiful from within), a bit of a trouble maker, non-conformist, defiant and hated authority. I think to be honest she’d be quite surprised. I was groomed to take over my Dad's business when he retired, but he died so that never eventuated. I then thought I’d be a professional dancer then I dislocated both my knees so that never happened either. Then I thought I'd be a chef but that didn’t seem that fun up close! So I think the 15 year old me didn’t even know that what I do now was a possibility. It was always going to be something in business, I just didn’t know what. When I was 16 I got a job with Digital Mobile (vodafone) working in retail, that sort of saved my life a bit. I was really good! That gave me direction and purpose at a time in my life where I’d pretty much lost everything and everyone. I actually failed school, and got politely asked to leave at the end of 6th form, so from that to where I am today it’s pretty amazing! 

Did you just buy a house in Waiheke?! How, Why, What is it like?!

Yes I did! It’s a bit of a long story really. I’ve lived overseas for a decade, but have always known that New Zealand is my home, the long and short is that I had some capital sitting in the bank doing nothing, so I decided to do something with it and buy somewhere to live. Unfortunately for us Kiwis property is still one of the best ways to make money in New Zealand long term, and I wasn’t ready to start my business yet. My health took a dive last year where I realised if I kept going how I was, I might die. It was a crunch point for me where I needed to make some significant life changes, and my lifestyle was my last option. I developed a chronic pain disorder where I was always in pain, and it started to attack my nervous system and mental health. There were days I just had to lie flat, and be horizontal. Pretty terrible for a 27 year old to have her body and mind giving out on her! I had to stop traveling as much, change my entire lifestyle, reduce my stress pretty much entirely, and stop all exercising and could only walk. I’m 65% better now, it took a lot of time though. 

On the house front, I got some advice from my sister who said if I wanted to buy to look at 100 houses to know exactly what I wanted, so I did that. It took me 18 months of looking, it was a very draining process, on top of that I was a single female, under 30 so agents and everyone involved was very judgemental and I’ve also been self employed for 10 years so getting a mortgage was another challenge. No one teaches you how to buy a house, or about personal finance at school so it was a steep learning curve! I ended up finding my house in March this year and moved quickly, went to auction and won it. 

I decided on Waiheke as I’d lived there twice before, I joked about it’s accidental lifestyle qualities - what I mean by that is that I am always working, it's the only thing I know, so by having to catch a ferry and living 5 minutes from 3 beaches, it was easy to go walking, and swimming and get fresh air. I wanted to be more healthy by moving there, and that is exactly what has happened, sort of by accident. I still work a lot, and I actually have really fast internet (fibre). It’s empowered me to continue working, but smarter as my ‘what matters’ is right outside my door. 

The houses are more interesting (quirky) on Waiheke, than in Auckland, I didn’t want to commute by car as it takes too long and isn’t my idea of stress free or fun, so by boat was way more appealing and I can work from anywhere so it seemed perfect. The house prices are also on par if not slightly lower than Auckland and you get the benefit of a sea view or living in the bush but still being close to everything! As a tourism market as well it was easy for me to rent it when I travel for 4 months of the year, there are some of New Zealand's best vineyards on the island too, and it’s a micro climate so the weather is usually quite pleasant. 

It really is paradise - quiet, communal, friendly, peaceful, and creative. 

I’m just renovating my bunk room at the moment so that I can start holding retreats for entrepreneurs, and women who want to reconnect with themselves, others and nature. I’m really big on building communities and personal development so I’m hoping to bring people and groups together who are looking for that. 

You have had three immediate family suicides including your Dad and two uncles, one family murder, and a 4th best friend who you sadly lost to suicide as well. How did you overcome this and turn your life around at 21? Can you tell us a little bit about your journey and any advice you have for people who are trying to overcome adversity?

Reading this question initially it was quite confronting as it’s quite a lot to take in but yes the reality is that is my life and some of my unfortunate experiences in one sentence. It was a really hard phase of my life going through so much trauma. I abused alcohol and drugs for a while to numb the pain, then one day I woke up and realised that I was failing life and that I would never recover or heal unless I dealt with everything, the next day after that I stopped drinking (for 2 years!), stopped wearing makeup, and let go of most of my friends that I realised weren’t really real friends and began the journey of getting to know myself, feeling what I needed to feel and working on myself from the inside out. I left no topic unturned and assessed and dealt with every single area in my life healing, learning and building including but not limited to sexuality, beauty, mental health, finances, earning and relationships. 

I wrote about it on my website and I think I capture the words perfectly their so I’ll put them here:

After decades of being at the hands of tragedy, Sian turned her life around realising at 21 that everything that made her confident was on her, and not in her. She set out to change this by starting again, stripping everything back and building herself up. Quoting that she was unhealthy and numb inside, and has spent the last six years focusing on her ‘mental and emotional hygiene’ which she describes as being an ongoing journey but mostly successful, and something that people don’t do enough off which we are starting to see the impacts of today. 

The world we live in is intense, and we often forget to learn about who we are, and what makes us tick. Society gives us a definition of what success looks like, and we compare ourselves and never hear that we are enough. Sian after living in the enigmatic Silicon Valley for many years realised that the best investment you’ll ever make is in understanding yourself. She learnt that you have to define your success, and decide what being enough is for you - thus removing yourself from the neverending rat wheel of climbing the ladder in life - leading to pending life crisis (which she has seen too many times!). ​

For the geeks out there, Sian adopts language and sentiments suggesting that life is a series of S curves and that we have thrived and plateau and reach new levels, often at the foot of naivety before we grow again. She is someone who has worked hard to master the mind, through techniques such as neuro-linguistic programming, and mastering her self-talk cycle. And has been known to create safe space in rooms of thousands of people when looking at themes of judgement, capacity for dealing and understanding problems and is fierce of the belief that we need to be teaching and learning compassion, empathy and understanding as our world gets more and more complicated. 

I got to know the real me, I spent a long time healing, and getting through the loss and trauma, I did work with a councillor, but I also worked on myself for about a year intensively, trying to figure out who I was, and just listening to myself. In the end I designed my life from the ground up and started living it, authentically. That’s how I’ve been able to travel around the world, work online, and build my career the way I have, it was because I spent the time to understand what I wanted and needed in life and built it. I focused a lot on personal development and being the best version of myself. It can be pretty painful and hard at times because you are looking at the ugliest parts of yourself as well as the world. I have moments where I don’t want to be resilient anymore because my heart is just so damn fragile, but that's life, and I get through those moments. 

My advice is to get to know yourself, spend the time figuring out who you are and what you want, how you want to live, develop yourself personally, learn what makes you tick, build a good support system, learn your triggers, find what makes you happy, build your foundation sometimes by stripping it back, seek help if you need it, take some time for yourself, ask for help, and get rid of shit people in your life that don’t serve you. You don’t have to have all the answers and there are no ‘shoulds’. The hardest thing about overcoming adversity, is that it never truly goes away. You just have to take your days as it comes and learn as you grow. Have good days and bad days, and realise that you are not alone. 

The most important thing is don’t compare yourself to others. We all have a different capacity for dealing with things. I learned this the hard way. My Dad dying was equivalent for my friends boyfriend breaking up with her, for me I was really hard on her as I thought it was ridiculous, but the reality was that my capacity for coping for that situation was greater then her boyfriend dumping her. It was in that lesson that I learnt to be compassionate and to create a safe space for people and to not judge or compare problems and realise we all have our trying times. 

Who inspires you?

This is weird but often myself! It's not a very kiwi thing to be proud of what you’ve achieved and accomplished and I’ve finally realised that I should be proud of where I’m at in life, and the person I am, and continue to evolve into. I’m working on my self worth at the moment, as I’ve typically been quite an insecure person at times! So at the moment, I'm really stoked with where I’m at, and incredibly grateful too. 

I’m inspired by a lot of my friends at the moment, mainly the ones who are getting divorced or separated. A lot of them are going through hard times, or have just got through it and are doing a lot of personal development but they are much older, like in their late 40’s and 50’s. I find it inspiring that whatever age you are, and whatever you go through you can continue to iterate and find a life that serves you, but also be a good person, doing right by yourself, and also those around you whether that's friends, family or children. 

Michelle Dickensen: if you don’t know Michelle you should, most commonly known as Nanogirl. Seeing a strong but beautiful and kind woman who is an engineer and an introvert!! be so passionate about creating positive change in the world is really inspiring to me, and doing so whilst being so unabashedly herself. I think Michelle would top most people’s lists in New Zealand, but I’m pleased to know her and watch her journey every day, she does so with such grace too! 

Cecelia Robinson: Founder of My Foodbag, she inspires me for a different reason. Having had two successful businesses and retiring before 40 is pretty epic! Not only that the focus on having such an involved family life, being an epic Mum, wife, business women and everything else is so awesome to have people managing this all and doing it with sophisticated elegance. You can’t be what you can’t see, knowing that its possible is awesome for me! She is also super approachable and quite funny and I love her honesty too. 

My friend Lavanya: An Indian transplant living in San Francisco, one of the smartest people that I know. I tell her stories, she hands me back equations, we often talk about how life is a series of S curves. I like that she continues to study to be the very best in her field when she is also the very best and she doesn’t let societal norms define her. A machine learning engineer that loves fashion, gaming, maths, makeup and fine wine. It’s delightful to have a friend that is so kind, so themselves, but striving to be the very very best in the world (her recent blog post on dark matter left her with speaking gigs for a solid month from the likes of Google. Don’t know what dark matter is? Google it.)



What is something you think people don’t know about you?

Here are a few random things: 

  • I’ve travelled to 50 countries, many twice. 
  • I’ve lived in these places for a month or more: Bali (x2), Thailand, Vietnam, San Francisco, Los Angeles, Auckland, Wellington, Waiheke, Japan, Argentina, Singapore, Malaysia. 
  • I did a 350 mile bike ride in Zambia over 6 days in 2016. 
  • I taught myself conversational Bahasa Indonesian & Swahili. 
  • I was a digital nomad before it was cool (lol). 
  • I’m a gamer! Haha. I love the sims, and age of empires. SimCity and Fallout shelter actually taught me a lot about life. 
  • I was a Latin and ballroom dancing champion. 
  • I’ve worked in a lot of industries! Hair and Beauty, Infrastructure, Roading & Civil, Construction, Telco, Tech, Media. 
  • I use to have a food blog, and would review local high-end restaurants in Auckland. 
  • I’ve worked as a paddle-board instructor
  • In a former life I ran code-free hackathons across the United States. 
  • I did my entire university degree online, remotely. 
  • I was as blonde as can be for most of my pre-adult life! 
  • I accidentally write poetry when I’m sad or mad

What does beauty mean to you?

I see beauty everywhere and in everything. Every face, every personality, every tree, leaf, everything. Beauty to me is abundant. It’s inside out and outside in, its authenticity, its living, and alive, sometimes it’s hidden below the surface that we have to look deeper to find, other times it is just there out in the open to see. 

It took me a really long time to see beauty in myself when I was 100% me, just raw, and now when I decide to wear makeup to enhance my features I feel that way too, it was learning not either or, but and. 

This might sound a bit woo woo, but beauty to me is often about energy. Do you ever meet people and you are just overcome by how radiant or enthusiastic, or special they are but you can’t quite put your finger on it? I love it when I encounter those people, so abundant. They remind me of literal sunshine. 

Maybe beauty means to see what's before you as is. 



Check out Sian's Instagram here and read more on her website and blog here.

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  • Very very interesting & inspiring story !
    Thanks so much for sharing.
    I could relate to so much of what Sian was expressing.

  • Wow Sian I learnt so much about you I never knew but I did always know you are as stunning on the inside as on the out
    So very proud of all you’ve achieved
    Lizzy ❤️Xxx

    LIzzy Maulder

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