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Cheryl Mack's Answers to Thriving Interview

Updated: Oct 18, 2019

Answers to Thriving with Cheryl Mack
Answers to Thriving with Cheryl Mack

CEO of StartCon - An international events & entertainment company in the technology industry.

Cheryl's hosted over 500 events including the largest startup and growth event in Australia, with over 4000 attendees from across the startup ecosystem and featuring speakers from the world’s biggest technology companies like Uber, Pinterest, and SurveyMonkey.


The ‘Answers to Thriving' is an ongoing interview series that takes a look at the women who have created a life of success. We uncover key moments, lessons and habits that have influenced the life they lead today.


You can’t start the day without:

I love Reddit as I don’t read a lot of news in the typical way but I love the fact that Reddit is generated and validated by a really large group of people.

A favourite quote is:

My university motto was “Tuum Est” which translates to “the world is yours” and that has always really resonated with me.

One wellness ritual you do regularly:

I go hiking a lot. I like to get outside into nature and just take a moment to appreciate the world outside technology, offices and the next payment start-up.

The last podcast or video that inspires you?

I love Adam Ruins Everything - those type of educational videos which having nothing to do with work.

A recommended read for personal growth:

I recommend High Output Management by Andy Grove to anybody who is looking to be a good leader or manage a team. He was the CEO of Intel for 20 years and a really amazing guy from what I’ve heard. The book essentially simplifies the whole process of producing anything and helps give an understanding of how to motivate people.

Which business or person inspires you right now and why?

In November of last year, I had the pleasure of meeting Jamie Siminoff, the founder of Ring. He was so down-to-earth and I really respect what he has built and how he grew a team around him in order to get where he is today. I find him really inspirational. His company developed doorbell alerts for phones, which have actively helped reduce crime by a significant amount in high crime areas. They’ve taken something that would traditionally have been a novelty gadget and turned it into something that actually protects people and makes them feel safer - I really love what he’s doing.

What has been the most defining moment in your career to date?

I would have to say when I was given the chance to take a step up on StartCon. Four years ago, the CEO of Freelancer Group approached me and asked if I’d like to help run the conference. I didn’t realize it at that time but, looking back, agreeing to do that was a very defining moment. I think everything that I’ve done over the last four years, building the company from nothing, wouldn’t have happened if I hadn’t said yes to that.

Who’s helped you progress the most in your career and what do they do to support you?

Matt Barrie, the founder and CEO of Freelancer Group that owns StartCon. By giving me that early opportunity to take on StartCon and allowing me to just run with it, he gave me responsibility and ownership over what I was working on and the freedom to make decisions - he trusted me. He’s been there to help solve problems, but by allowing me to take the lead, he enabled me to go from a generic marketing manager to the CEO of a global entertainment company in the span of four years.

A fear you've had to overcome to pursue your ambitions:

A big fear of mine is making the wrong choice. There are so many different ways you can go about doing any given thing or addressing any given issue and I’m always scared I’m going to make the wrong choice. I’m beginning to recognise now, that there never really is a wrong or right choice; it’s about the execution - how you follow through with the choices you have made. It’s never black and white because you can only make choices based on the information you have at the time, so it can never be perfect and therefore there should be no regrets. If you do make a wrong choice, in reality it’s never as bad as you think.

I’m beginning to recognise now, that there never really is a wrong or right choice; it’s about the execution - how you follow through with the choices you have made.

An achievement you're most proud of:

I’m pretty proud of the Pitch For A Million competition that we ran in 2018. Each year, we bring together some of the best startups and I thought it would be great if we could actually offer them a very big, shiny prize at the end of that. So I decided to try to get a VC Fund to put up a million dollar term sheet as the final prize. So many people thought I was absolutely crazy for even thinking I could make that happen, but I went around and pitched to them all and I did it – Right Click Capital came onboard to support the competition with a $1M investment for the winner. And it worked - we had 600 startups pitch across 15 events and helped a lot of founders get on a stage. Even though only one startup came out on top, we still helped many other founders get a lot of additional investment from other investors as well.

Career advice you wish you'd been given in your early 20s:

I think my general advice would be to write it down. If you have a conversation with somebody, write it down, put it in an email, take notes and give it to them. There are so many opportunities for miscommunication – people’s memories are terrible and misunderstandings happen. If you write it down and send it back to them after you’ve had the conversation, it just makes things a whole lot smoother. I’m not perfect at this but there are so many instances when I wish I’d done that.

For women who want to make a positive change in their life but don't know where to start, what advice would you give them?

My advice whenever I talk to really early-stage entrepreneurs is to find something that you’re interested in. Once you are clear about that, then I think the next step is to do at least one thing every day in relation to that, or working towards that goal. I call them non-zero days. You have to do at least one thing – whether it’s writing down some ideas, or booking a meeting and having a chat with somebody, reading some relevant articles, or doing some research – it doesn’t have to be big. You don’t have to build an app in a day, but every day needs to be a non-zero day.

You don’t have to build an app in a day, but every day needs to be a non-zero day.

What does thriving mean to you?

I think it’s feeling passionate about everything that you do.

Anything else you would like to share with the Thrivhers community?

StartCon 2019 is on November 22nd and 23rd in Sydney. Tickets will be going on sale in June. In the meantime, make sure you go to to register so you don’t miss out on tickets!


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