Embrace imposter syndrome. When it’s not holding you back, the level of care and attention that imposter syndrome can bring will make you better at your job. People who worry about whether they are doing a good job or not are often the ones doing the best job. I’d prefer to worry and care a lot about, for example, our customer’s data security than to make a mistake and screw it up because I haven’t cared enough.
CTO Emily Castles started her professional life as a Civil Engineer but moved to software 10 years ago in search of a more flexible working life. She has managed distributed teams her entire career, previously serving as Head of Engineering at Bizimply.
Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
I studied Civil Engineering in college and worked as a water and wastewater engineer for most of my 20s, travelling the world in between jobs. I enjoyed the varied projects that I worked on but I hated where I worked — business parks, building sites, the less interesting parts of the world. I also have an aversion to being answerable to office hours. Commuting to work gives me a knot in my stomach and I’ve always struggled to work to the boundaries of a traditional workplace.
When the financial crisis hit in the late 00s and I was made redundant from my Civil job, I took the opportunity to start a new career that let me have more freedom. I gravitate towards learning technical skills so, while I thought about areas like business and management, ultimately, I went back to college to study computer science. I’ve been working in the world of startups ever since as it ticks so many boxes for me — freedom, job satisfaction, fast moving, constant learning. I cut my teeth as a software engineer with a consultancy in Dublin for 3.5 years before embarking on my remote working life with Bizimply — who were open-minded and kind about my needs at a time when remote working wasn’t that accepted in Ireland. I’ve split my time between Dublin and France ever since.
When I first spoke to Dee (CEO) about Boundless in early 2019, I really didn’t intend to be involved at founder level. In fact, even though she was hinting in that direction I wanted to be an individual contributor for a few years to focus on technical work. I figured I’d build some software for Boundless instead. However a few months and a couple of workshops later, I couldn’t resist. The concept of the company is so close to my heart and having the opportunity to build a remote company the way that I wanted it to be was irresistible.
Can you share the most interesting story that happened to you since you began leading your company?
We started Boundless as a remote-first company not long before the pandemic began and we were committed to this way of working from the outset. However, working from home during the pandemic is not a good representation of what it’s like to be remote-first. None of us anticipated not meeting our colleagues or working from kitchen tables. It’s been a rough period for, well, everyone.
Despite these difficulties, the pandemic is bringing about a shift in global working trends that is so intriguing to watch. Large corporations are ditching the office and governments are introducing new remote working legislations: the face of work has changed irreversibly. There is an opportunity now for employees to drive change and put their personal lives before work in ways that wasn’t possible before. I can’t wait to see that movement develop and grow.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
Working remotely definitely comes with its challenges at times! Our company runs payroll monthly on behalf of all our customers. I was on vacation during our first ever payroll run and I really took ‘work from anywhere’ to a new level. My intention was to transfer funds for our very first paychecks from the beach. However, inevitably there are network problems whenever you have to do something very important away from your desk. I ended up retreating to the top of the sand dunes, phone held high to maximise coverage and made the transfers using my laptop whenever the network would allow. Thankfully everyone got paid. The lesson? Don’t mess around when it comes to paying people accurately and on time.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
Rodhan Hickey — CTO during my time at Bizimply. Rodhan joined at a time when I had been running the engineering team with sketchy experience for a little too long. I was craving someone more experienced to work with. While working with him, I picked up so many technical and managerial skills from him that really set me up for moving onto this role. Rodhan also was the one in my ear when I moved on from Bizimply telling me ‘you should talk to Dee’. He’s always shown belief in me, even if I didn’t have that belief in myself at the time.
Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?
Women are less likely to apply for jobs unless they match close to 100% of the listed requirements. No one writes a list of requirements for starting a company; you define the job spec for yourself along the way. The unknown nature of the job definitely plays a big part in lower participation rates in my opinion.
Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?
Having been in this position for 2 years now, I know that I would be way more likely to do it again. For me, I have learned on the job that I am exactly the right person for my job. With that in mind, government schemes and educational programs that incentivise young people to set up business early would go a long way towards helping.
This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?
I cannot describe the levelling up that this job has brought about in me. Regardless of what happens in the future, I have gained more ambition, skills and experience than I ever imagined possible. If you’re choosing between, e.g. an MBA and founding a company, found a company and fast track instead.
What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?
Founders are not special unicorns. There’s a lot of hype about founders and founding teams that paints, in my opinion, an inaccurate and frankly unachievable picture of what it is to be a founder. One might get the impression that you need to be a master of everything before you start: thought-leadership, marketing, technology, productivity, finance, the list goes on. Yes, you need to be able to turn your hand to many things and be willing to learn but the reality is, a founder is just a person who shows up to their job every day, works hard and consistently executes.
You don’t have to live on the breadline. Funded founders should take a reasonable salary and any investor who disagrees with this should be questioned. You cannot achieve at your job if you are spending energy worrying about your personal finances.
Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?
The most important traits that I have identified so far are:
Ability to execute. Ideas are plentiful but there is a lot of hard graft and plain “showing up” involved in getting a business off the ground.
Ability to learn quickly. In the early days of running a company (and I’m sure the later too — I hope to learn that part), every week brings up something new that I need to learn about.
Comfort with uncertainty. I laugh at this one as it has been on all of our job specs since day one but I’ll admit that it has only truly sunk in recently for me. Being part of a startup means that things are always broken and you simply have to live with that fact and spend your energy figuring out which broken thing is the next broken thing you should fix.
Based on your opinion and experience, What are the “Five Things You Need To Thrive and Succeed as a Woman Founder?” (Please share a story or example for each.)
Embrace imposter syndrome. When it’s not holding you back, the level of care and attention that imposter syndrome can bring will make you better at your job. People who worry about whether they are doing a good job or not are often the ones doing the best job. I’d prefer to worry and care a lot about, for example, our customer’s data security than to make a mistake and screw it up because I haven’t cared enough
…but shed imposter syndrome 🙂 There are times you need to stop giving a *#!& and get on without things being perfect. I used to prepare deeply for everything: every interview, board meeting, investor pitch. At some point, this just became impossible to sustain and I learned to trust that I have the ability to do these things without over-preparing each time.
Saying No. I seriously doubt that this is the experience of all women, but my Irish Catholic, convent-school upbringing has strongly instilled the ‘Be A Good Girl’ narrative in my brain. This has certainly caused me problems along the way and something I still work on daily as I find it very counterintuitive to disappoint people — and it’s impossible not to disappoint people in this role. I have to try extra hard to ensure that I control my own time by saying No.
Know your weaknesses. Knowing and being comfortable with your weaknesses empowers you to fix them, head on, in a way that works for you — see Saying No above.
Find other founders. Speaking to others who you like and respect, and who you can talk to openly about the challenges is a lifesaver during stressful times.
How have you used your success to make the world a better place?
Well I have to say this, but I do believe that Boundless makes the world a better place. It empowers companies to treat their employees equally. It allows employees the opportunity to access jobs all over the world and to shape their lives in the way that they want to.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
Anything that challenges how we work is interesting to me as it can impact so many. The recent acceleration of the remote working trend on the back of the pandemic will, in the long run, empower so many to change their relationship with work and allow them more freedom to shape their lives in a way that works for them.
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.
