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Balancing the Grind with Olly Headey, Co-Founder & CTO at FreeAgent

Olly Headey is the co-founder & CTO at FreeAgent, an online accounting system specifically designed to meet the needs of small businesses, freelancers and their accountants.

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

Hello! I studied computer science at uni and my first job was for a video games startup. It was a complete trial by fire. I’d never worked so hard before and I probably haven’t since.

Working long hours was a regular occurrence and we did a few all-nighters – the games industry was tough! I lasted a couple of years and I learned a lot.

At the end of the 90s I went backpacking and ended up in Sydney needing work. I got a job at the ABC in an R&D department where I built an early internet radio streaming prototype. I loved Sydney but I moved on and eventually returned to London where I worked for Capital Radio for a few years which was enormous fun.

I ended up working in finance which I found something of a tough grind after working in media for so long. To make things more interesting (and, ok, to make a bit more money) I set up a company and contracted myself into banks, which was my first experience of freelancing and the pain that was small business accounting at the time.

I’d harboured a desire to start a proper product business for a while, and it was this – along with a sprinkle of serendipity – that led to meeting Ed and Roan and starting FreeAgent in 2007.

Our early mission at FreeAgent was to “democratise accounting”. We bootstrapped the company for the first 18 months, gained a bit of customer traction and took early seed investment from SaaS legends Christoph Janz and Robin Klein.

The next few years were spent improving the product and growing the business through more investment (seed, institutional, VC, venture debt, crowdfunding – you name it, we probably did it). This culminated in an IPO in 2016 on the AIM market in London, which was swiftly followed by an acquisition by NatWest Group in 2018.

The company now has over 250 staff and we have around 120,000 customers. I continue to lead the engineering organisation (which itself is over 100 staff) as CTO.

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

I still have the original title but my current role is very different from the early days where I’d find myself coding new features, handling customer support tickets, building hosting infrastructure and flying to London for board meetings (often all at the same time!).

The CTO role today is one of leadership across a broad area. It’s about aligning our engineering staff around common goals and connecting the work we do into the wider business mission and priorities. Engineers want to solve interesting problems with a strong purpose and with minimal bureaucracy. It’s also my job to make sure they can do that.

I spend a chunk of time in meetings, but only the useful ones where I can help unblock things or where I’m needed to make certain decisions. It’s very easy for managers and leaders to block entire weeks out attending endless meetings, but this is unsustainable and ultimately self-defeating.

And let’s face it, it’s also boring. Leaders have to learn how to delegate effectively in order to grow the careers of their own staff and create the leaders of the future. You can’t do that if you’re stuck in meetings all the time.

As a large, growing organisation I spend a lot of time on hiring and our recruitment process. Founders need to spend a significant amount of time on hiring, far more than they probably realise. The job is never really done, there are always improvements to be made and the landscape is constantly changing – especially in tech.

Another important aspect related to hiring is outreach into the community, which is something that I’ve spent a lot of time on over the years in order to give ourselves an identity, a personality even, and show what makes us a great place to work.

I also sometimes get stuck into more fine-grained work on the technical side, such as reviewing technical proposals, attending architecture meetings and our weekly ‘all hands’ meetings. Although I’m not hands-on anymore, I still have to devote time to understanding how our systems are evolving as well as keeping up with the relentless changes in our industry.

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

All three FreeAgent founders operated completely remotely for the first three years of the business, so we got pretty good at it and we were early adopters of collaboration apps like Google Docs, Basecamp and Skype.

When we started hiring full-time engineering staff in 2010 we initially focused on hiring people in Edinburgh, but our growth plans and the number of available Ruby programmers (at least those who were brave enough to work in a grungy office for a scrappy startup with possibly limited prospects) in Edinburgh didn’t align.

As a result we started hiring people remotely (a rarity in those days) and adapting our day-to-day processes to make it work effectively. Looking back, it was a huge win for us.

It’s no surprise that today my role is extremely remote-friendly. The tools we use to run the business all facilitate remote working and collaboration as they can be accessible from anywhere.

Our office is set up well for distributed staff to dial into meetings, and we try to adopt a “remote-first” mindset. I’m fortunate enough to have a dedicated home-office so I can work at home and focus when I need to, or I can take a walk into the office to meet people and enjoy the space we have.

As a business we’re pretty flexible about how people work and we accommodate people’s different needs and personal responsibilities, whether that’s part time working or different working hours. We also offer “work from anywhere” time each year, so if people want to take a week or two to work from elsewhere, they can.

This is great for people who want to visit their home country but want to stay longer than the usual 2-3 week holiday. I still find myself working a traditional 9-5 because it suits family life quite well, but it’s great to know the flexibility is there when I need it.

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

The best jobs are those which don’t feel like work, and they’re a real privilege. But even if you’re lucky enough to have a job you love, I think you still need to detach from it regularly. Work can easily become all-encompassing which, to me, isn’t healthy in the long term.

You need to balance work with other things – family, friends, hobbies, downtime, even outright laziness now and again. This time away from work is usually when the good ideas happen. Step away, switch off and give your brain a chance to get creative! It works wonders.

In the year that we started FreeAgent, all three founders became fathers (in Ed’s case, for the second time). We were all in our 30s and bootstrapping the business, so at times we had to pick up side work to help pay the bills.

We were pretty good at juggling things, but it also meant that work couldn’t be this all encompassing thing – the classic Valley startup dogma of 100 hour weeks, working every weekend, “always be hustling” just wasn’t possible, thank goodness.

I’m sure we thought about work a lot when we weren’t working (and spent time reading about work-related things), but that day to day work/life balance was sort of inherent given our respective situations.

As the business grew, this balance became part of our company culture and it still is today. In 15 years I’ve rarely stayed in the office beyond 5pm and I rarely worked on the weekend, and this is for someone responsible for keeping a business online 24/7/365. You just have to make sure you can be super-productive and focused in the limited time you have.

So a healthy work/life balance is really important to me and, while this can be an unpopular opinion in the VC-backed tech world, we’ve shown it’s definitely possible to build a successful business while also having a life beyond work.

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

The past 12 months have been a challenge for sure given the pandemic but despite what we’ve all been through I wouldn’t say I’ve had any sort of great awakening, personally.

I’m definitely trying to read more books this year – a broader variety too, from novels, to business books, to biographies – as I found myself doom-scrolling on social media and news apps way too much throughout 2020. That level of distraction definitely isn’t healthy, but it’s still a bit of a battle if I’m being honest.

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

On the newsletter front, I’m a huge fan of Dense Discovery which is a collection of ideas and inspirations about critical thinking and productivity.

I think Kai does an amazing job with that, so you should definitely subscribe. From a work perspective I’ve been reading Gergely Orosz’s new Substack on engineering management which is excellent. Worth paying for if you’re in that field. Steven Sinofsky’s Hardcore Software is an incredible story about the early years of Microsoft told via Substack newsletters. Outstanding.

I still read a few magazines (old school!), such as Private Eye (the best news source), Courier and Harvard Business Review for business stuff.

I’ve read quite a lot of books (new and old) this year and I absolutely loved Project Hail Mary by Andy Weir, The System by Ryan Gattis and The Art of Leadership by Michael ‘Rands’ Lopp.

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

I’m an Apple fanboy so, for my sins, my favourite gadgets are my Mac, iPhone and Apple Watch. I’m a sucker for great products with classic designs. See also: Sonos.

I’m a keen photographer and I love the Fujifilm X Series cameras. I recently bought the X-S10 which is a total delight.

There are a few apps and services that I subscribe to and would recommend to everyone: Spotify for music, Fastmail for email and 1Password for life admin. I also started using Mailbrew recently for aggregating news, newsletters and social media into a single daily digest. I highly recommend it.

I’ve also recently started using Busuu for learning Spanish which is brilliant.

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

I’m going to cheat and pick two. I’d love to hear from Tobi Lütke, CEO of Shopify, and David Heinemier Hansson, CTO of Basecamp. They were both super-influential for me when we started FreeAgent, and they still are today. They’ve accomplished so much and stuck to their principles over the years and decades. Kudos.

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

It’s good to have goals and a deep desire to accomplish something, but you have to try and enjoy the ride, however bumpy (and it will be bumpy). And don’t forget life happens in the in between, make sure you don’t miss it.

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About Author

Balance The Grind gives me a platform to talk to these people about how they're achieving their ideal lifestyle. I'm inspired by the passion, the work ethic, the hustle; and these conversations motivate me to live life the way I want to live it.