CEOs / Founders / Interviews

Balancing the Grind with Dan Draper, CEO & Founder at CipherStash

Dan Draper is the founder and at CipherStash, a cybersecurity startup based in Sydney and in the US.

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1) To kick things off, could you tell us a little about your career background and current role?

I’m the CEO and founder of CipherStash, a cybersecurity startup based here in Sydney and in the US. I’m a software engineer by training and have spent the vast majority of my career building or working for startups.

In fact, I added it up recently: CipherStash is the 9th startup I’ve worked for! I co-founded 2 of my own in my early career with some limited success. I’ve since been fortunate to work closely with other founders and recently got the itch to start another business of my own.

2) What does a day in your life look like for you? Can you take us through a recent workday?

My day starts with coffee. I’m not going to pretend that I’m not a slave to caffeine! But with my coffee I have a solid breakfast of overnight oats immediately after doing 20 pushups to get the blood pumping. 

After that it varies quite a bit! My days often have a lot of meetings with my team, speaking to current or potential investors and clients, writing emails or articles for our blog and if I’m lucky, from time-to-time I get to write some code. As the founder of the business I think I’ll always have a passion for technology but my team is glad that my coding is limited to experimental or recreational endeavours!

3) Does your current role allow for flexible or remote working? If so, how does that fit into your life and routine?

CipherStash is a fully remote company and so I work from home full-time. It works well for me as I find it’s great for focus and I appreciate the flexibility. I do really enjoy meeting with customers face-to-face over coffee or lunch and now that we are able to fly again I’ve relished travelling for conferences and drumming up business interstate and overseas.

As a team, we do everything over Slack, Notion and Google Meet. I find working that way pretty easy but socialising in a remote-first company can be tricky! We make sure to put specific times in the calendar where the team can just chat, play online games or socialise.

4) What does work-life balance mean to you and how do you work to achieve that goal?

As a startup founder, work-life balance is a tricky topic! However, I think the main driver for working long hours is the feeling that we didn’t get done what we felt we needed to do during a typical working day.

My approach to this is to make sure I block out sections of time in my calendar where I can focus and get into a flow state. It doesn’t always work but if I get enough of this during the week I tend not to feel like I need to “catch-up” on weekends. Being super disciplined with my time is fundamental to not only getting my work done but also getting time to relax and unwind.

I also train in Hapkido (a Korean martial art) 2 nights a week. Admittedly, sometimes I have to drag myself to training after a long day but I always feel better for it and it’s a great way to reset my brain. There’s no time to think about work when someone is trying to punch me in the face!

5) In the past 12 months, have you started or stopped any routines or habits to change your life?

I started this a bit more than 12 months ago but I see a psychologist every month. I started seeing him when I went through some personal challenges but I find even if I’m feeling mentally healthy, regular conversations with my psych are really valuable. The sessions provide space to unpack any challenges I’m facing in my work or personal life and to fine tune my emotional responses. It really is like the gym for the mind!

Another habit that I’ve started to develop is a quarterly “fear setting” exercise. Tim Ferris coined the term and it is the process of writing down what you’re afraid of right now. Through the process you articulate what would happen if your fears were actually realised and what you could do to prevent them.

When you label and quantify your fears they are almost never as bad as your subconscious would have you believe. Plus, by taking a systematic approach, you can put together a plan to prevent the fears becoming reality. I was sceptical at first but it really is a gamechanger!

6) Do you have any favourite books, podcasts or newsletters that you’d like to recommend?

Books: Grit by Angela Duckworth and Atomic Habits by James Clear. These two books have totally changed the way I view my career and manage my life.

I listen to a lot of podcasts covering a variety of topics but my current favourite is called “Maintenance Phase”. It unpacks and debunks the junk science behind wellness fads. It’s both informative and highly entertaining!

7) Are there any products, gadgets or apps that you can’t live without?

I’m loving my Oura ring right now! I’ve had an Apple Watch for years but I don’t like sleeping with it on. The Oura tracks my sleep and I forget I’m even wearing it.

8) If you could read an interview about work-life balance by anyone, who would that be?

My wife and I never had kids and still sometimes struggle to pack everything in. I’d love to hear how entrepreneurs who are also parents manage everything. It seems like magic to me!  

9) Do you have any last thoughts on work, life or balance that you’d like to share with our readers?

Vulnerability is hard but it’s freeing. If you’re grappling with everything that’s on your plate, don’t be afraid to tell someone that you’re struggling. It doesn’t have to be a public declaration but sharing your fears or anxieties with a friend or loved one can really help unpack what’s bothering you and bring into focus what must be done.

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About Author

Hey there! I'm Hao, the Editor-in-Chief at Balance the Grind. We’re on a mission to showcase healthy work-life balance through interesting stories from people all over the world, in different careers and lifestyles.