Reflections
Over the last 18 years i've been fortunate to work with some brilliant people; super talented and highly successful individuals who I've learned so much from. Some i've built businesses with in an office, some I've run teams with remotely, and others I've been lucky enough to stumble across during my career between the UK and Australia.
The 'Reflections' interview series is an opportunity to re-connect with these people, lift up the hood and see what drives them. My aim here is to create an inspiring and actionable content series that will benefit folks whether you're starting a business or a seasoned professional.
First up is Leigh Barnes
Leigh started out his career with a passion for digital design that quickly pivoted into software engineering. He has worked all over the globe; Canada, UK, US, and Africa for highly innovative companies like Amazon, NASA, and Red Bull. He's founded and managed startups in cloud infrastructure, payment, data processing, and fulfilment industries and, more recently, Leigh was the CTO of Eight a digital product company making Shopify themes and apps, which is where Leigh and I met.
Leigh was the first hire we made in a C-suite position. The business had grown rapidly during 2020 and needed a senior tech leader who innately understood the Shopify landscape to lead and inspire our development team. I came away from my first conversation with Leigh thinking how rare it was to find a tech leader with such a dominant empath string in their bow. Leigh is currently working in the AI space cooking up some cool stuff in the eCommerce industry.
Recently, I had the pleasure of catching up with Leigh and we delved into 11 thought-provoking questions.
Let's get into it.
1. In your own words, what do you do Leigh?
TL;DR
I always have a hard time answering “what I do” but the nuts and bolts of it is simply solving puzzles and adding value to individuals and companies that surround me. I live for the challenge and the progression of constant learning and innovation directly from the frontline.
The rest
I always state I am a software engineer first and foremost, it helps at dinner parties cause people don’t ask much more. I used to use “I do stuff with maths and algorithms in computing”, which normally got the glazed eyes and an exit from the subject.
In reality I sort of just had a needs must approach to what I do. I learn fast and adapt quicker than average, which is probably a throw back to a life of ADH(D) survival. I drop the D because it’s a thinking system not a disorder.
Over the years this has been much more vast than just writing code for interfaces, backend systems or data. It became adapting to handle all of those full stack engineering needs but bridging into infrastructure and then into leading, mentoring and building amazing teams. Alongside all of the needs that arise in startups and at senior leadership levels which has encompassed time doing everything from sales, marketing, pr, strategy, transformation, management, project lifecycle and program management, making the coffee and cleaning the office. We all have the ability to adapt and adapt quickly as long as we can have the confidence and the right attitude.
My industry experience is broad, a really massive list, but for most of my career it has been in spaces with direct ROI, as I like the direct value associated with any work put in. This led me to chose E-commerce as my focal area nearly two decades ago, with the majority of projects being solving puzzles within the Shopify ecosystem.
2. Have you had any defining moments that have led you to where you are today?
Oh man what a massive question, there are too many defining moments to list and many of them are ones you can only learn first person so I will just list 3 generics from my journey.
i. The day some one said “you know you would be a better engineer or technical than a creative right?”
Listen and take external guidance, you don’t have to take it but every so often… This was the spark of my journey entirely, I’m glad I listened. The saddest bit is I cannot even remember the individuals name.
ii. The day I realised that you can literally achieve anything.
That doesn't mean it won’t be hard. But the belief that when someone throws something at you, you are no longer daunted by it. In software / development I normally define this as the point where some one breaks out of the junior, mid, senior, principal, whatever mindset and suddenly believes internally that almost any problem can be addressed (solutions are relative). In reality it’s easier to grasp within the confines of code, but it translates across life. You get to pick your battles, but that knowledge that you can is formative in my mind of all defining moments. And ultimately that people don’t fail they quit.
iii. The day I learnt that every adversity is simply the ability to learn, no matter how entirely shit it is, we all get the opportunity to take that and use it forward.
I learned this way too late in life, but addressing it backwards, the fight or flight responses were lucky, and forward I can be more concerted with that. Anger, stress or strife is never best served on anything that is done.
3. Have you had any challenges or setbacks you have had to overcome? And how did they affect who you are and how you conduct business today?
I think the last point from the question above actually highlights this the clearest. I, due to necessity, went entrepreneur driven in the early 2000’s. Spawning multiple ventures taking on more than was feasible, living the highs and lows, the successes, failures and exits.
Some challenges & lessons would be:
Challenge: Shutting down something you built with everything you have in you.
Lesson: Learning to disconnect the emotion, at the right time. It’s hard but it’s a great lesson that has stayed with me.
Challenge: Cashflow, bankruptcy, financial scaling issues, buy outs, redundancies & shutdowns
Lesson 1: Lived pretty much all of these. You learn, and you learn how to handle the weight. The human cost is the one that haunts me more than some tough times personally.
Lesson 2: Aggressively start small, scale as needed, forecast and plan but sustainability first and foremost.
Lesson 3: Cashflow is indeed first and foremost in most truly viable, non unicorn, ageless businesses.
I would love to say I have survived all of these unscathed in this life, ultimately they all taught lessons and ones I couldn’t have learned any other way. I appreciate and cherish each and every single challenge, and adversity, business and personal.
However once you have seen the “shit” you do get a 1000 yard stare and disengagement from the emotion. I paid the price with many years of, for lack of a better term, functional depression. It cost me a whole lot in this life not addressing that. The collateral has been mental wellbeing, my health, relationships, friendships and a whole swathe of other stuff that matters and got lost in the clatter of business challenges.
Understanding that and putting the value where it needs to be has been the most amazing journey and one I have zero regrets about. I would make every decision again.
4. What does success mean to you?
If I was asked this 10 years ago, I would have probably quoted Wu-Tang Clan - C.R.E.A.M (Cash rules everything around me) lyrics.
While cashflow and fluidity still matter it has faded far from my personal measure of success. It still holds a key when I talk about business. However for me that has faded.
I measure success based on a few criteria:
i. Am I happy in the outcome?
The peace and serenity surrounding the term happy is one of my key measures and it takes many forms. I will often state “Just chasing happy” to encompass those levels of success in outcomes and goals.
ii. Have I planted flowers?
I heard someone say this more eloquently than I could recently so I will paraphrase.
“In this life we see decay in all aspects, sometimes in cracks in hard concrete surfaces and walkways, in broken windows or paint-less tumbled down walls. People walk by, they make comments, they avert their eyes. As people we don’t have to solve the situation, but we could change it. By planting flowers that may in time grow in the cracks where the ground is showing, and trees in the shade of which we will never sit within”
I have this as a measure of success in the mindset of;
‘Did I as an individual leave things in a better state or plant the ground for those beyond me?’
This pertains to all layers of business leadership success for me. As a leader , it doesn't matter about living the success, what matters is that you take the actions that can potentially replace 'decay' with something that changes the context from negative to positive.
iii. Have I made my self redundant by empowering everyone around me?
I view this as my highest measure of success. Have people around me stepped forward, grown to replace my input and best of all, far surpass it. At this point I can either focus elsewhere or exit the focus satisfied that there is a path forward.
5. What drives you to do what you do?
I have those demons in my head every morning that go, ‘oh shit he is up, what the hell is he gonna do today?’ I want to leave them guessing…
I don’t really know what drives me, but I know that the foremost is chasing happy, and just living the journey, taking it all in. I have one shot at it, so this is my shot. I will leave very little on the table, fully send it.
6. What keeps you awake at night?
Hmmm not much honestly, that being said I have had a life of insomnia! I sleep a handful of hours each night very deeply. Very seldom with dreams. So I sleep when I go face down.
I actually delved into computers, tech networking, hacking, piracy you name it in my teen years just because I was always awake when the world was sleeping. So that kinda set up the foundation of my professional journey.
Nowadays nothing really worries me, I sleep when I need to and the world can be burning I wont awaken.
7. Do you have a daily ritual or any practices you incorporate into your life?
I have a few, they shuffle a bit just depending on the day and circumstances but generally:
Appreciation Time
I wake up and drop at least one message to someone just telling them 'hey' and why they matter in my life. I do not expect a response. This is my way of not letting people get lost in the wash of life. I started this as an aspect of mindful reflection and appreciation for the insane input, lessons and growth that I have experienced because of the awesome giants the shoulders on which I have been carried. I have left these too late in life, but it is now a practice that I do daily.
Morning stop and coffee
I find in the average day there is a sort of planning and chaos mitigation phase first thing. So when I’ve done that, I take a 20 min reflection, walk through the park and grab a coffee before getting back at it for the rest of the day. This seems to allow decompression time to make more concerted decisions, handle situations with more care and empathy. I generally find this makes me a better person… The coffee probably helps as well.
Run time
This has been a 12 month journey so far but one that is not going anywhere without one hell of a replacement. I started going for a long walk at the start of my day and then when it ended. I was training for a hike and my weight, health and fitness were totally fucked. Walking became this great time to really have a conversation with myself, just quiet reflection and my mind started to need it. The length of the walks was getting a little ridiculous and time consuming: 2 ish hours twice a day is challenging to balance easily!
One day I said ‘so like what if I try and jog / run a bit’, my knees are toast from skate/wake/snowboarding, pins and staples and things through out. So I started and I could barely jog for 500m before I was in pain and out of breath, but in that moment I realised my mind went quiet, I was focused, and the boost when my heart rate stopped pinging its limit completely elevated my mood.
Something clicked that day and much like the rest of my life I decided, nah I need to know how far I can take this, where does Leigh end? It went from 500m → 1km → 3km → 5km → 10km → 20km → 30km, and now includes mountains, trails and there are gonna be a whole load more. I got stronger, I got faster, and I didn't get bored. It's been the driver to show me how deep the mind is and how much I can take. I’m now chasing an Ultra as my primary goal, I don’t care about time, I care about doing it.
I now run religiously every day, sometimes twice averaging about 75km a week. I don’t think there is a single runner that loves running, but the benefits of being outside, rain, snow, thunder, lightning, trails, mud are huge, and finding out you are made of iron through it is about the best thing for my mind.
I wish I found this earlier in my life. 44kgs of weight gone, stronger, and with loads more energy; I may not love the running but I Love running.
Side note: The same benefits are likely to be found any time you break out of your cocoon of life and get in nature, in the greenery or alongside water. Doing something daily will totally change your life, I dare you to scrap consuming a tv series or scrolling socials and get out there hammer at it.
8. How do you set your goals in business and in life?
So tough, I kinda set goals across business and personal life in the same approach.
I run a constant accountability system in notion and I split goals up in to three categories (other than personal or business)
i. Long term Goals
What is the major value chase? This could be a project completion, or something like an investment amount per year. I track these based on the completion of mid and short term goals & wins.
a. I add to these but also prioritise and keep a maximum of 8 goals in play at any given time (personal and business)
b. I am not precious about replacing a long term goal or moving it from active to back burner as life changes. I have change as a constant in all goals.
ii. Mid term goals
These are always linked to the long term goals in play. I generally like to see these as 25% of the over arching goal or key areas. I aim, not always successfully, to keep a max of 4 of these per long term goal. I almost view them as quarterly not sure why but that has worked for me.
iii. Short Term goals
I have no limits on these, but I try to keep them staggered and achievable, often as a culmination of wins (tasks) that I can achieve and see moving daily, weekly, monthly.
So that is how I plan out goals. I know some people set goals that are sky high, and whilst I never aim for mediocrity, I think failing to achieve goals can be really detrimental. I focus on stretch, as in pushing outside of my comfort zone, but achievable as my core goal criteria. Knowing what is achievable and then choosing to raise it within a range of discomfort. That takes practice, and getting it wrong!
I mentioned 'wins' which is what I call tasks. My life is governed by these, I set them up and time box them every day and associate them to corresponding short term goals in play. I hold my self accountable to these 'wins' and set them as my daily ‘go at it’ list. I start every day prioritising the top 3 and then chase them.
I am far from perfect at setting goals. I have only one rule; goals that make my accountability chart are ones I have the ability to manage the outcome and have autonomy over.’ External or team goals are tracked in their own accountability spaces within their context. Separating external was the greatest mental boost for me, and brought what actually mattered to me back into top priority spots. That has been a major learning across multiple companies, teams and organisational workflows. Some goals moved from accountability to being shuffled out just due to factors I couldn't control.
9. What advice would you give someone starting out in their own business today?
Just Start.
You are gonna make a whole lot of fuck ups. Starting a business even as a seasoned business leader is going to be a learning process of what works and what does not. Entrepreneurship for the vast majority of the early stages is best summed up by: “Fuck around and find out”.
It’s the greatest journey, love every second of it!
Stay Humble.
Take advice, have conversations, leave your ego to the side, and from time to time take 10,000 yard views. Choose the ones you take these views from wisely but be willing to let someone else break you out of your single minded devotion.
Be the leader you always wished you had.
Stay Grounded.
Shit is going to go wrong, not if, when. The single most toxic thing is to lose your head, get shaken. Pivot before needed, don't let something play out. This is something I have seen so many times. Staying calm and collected is the single most valuable approach, because even if you have to entirely pivot you will be able to do it authentically with the support of your team. Having that calm demeanour and approach is what great leaders all share, own it.
Build your Advisory Army.
Select and find people who have experience to advise you before you jump at decisions, sound your ideas with others. Talk to people with no filter. Choose this team wisely.
Empathy First.
Every single person has strengths and weaknesses, know the people you bring into your teams, foster an empathy first approach. This will get people to shine in their own spaces and focal areas.
10. What practical tools, podcasts and books would you recommend?
Business Books
- THE ADVICE TRAP: Be Humble, Stay Curious & Change the Way You Lead Forever by Michael Bungay Stanier. One of the greatest empathetic leadership books I have read. There are many great ones but I have quoted from this often.
- High Output Management by Andrew S. Grove. This should be a staple reading for anyone in the fast paced tech space. I live by let chaos reign then reign in chaos.
Tools
- Notion: I use an accountability tracker in here and I would be lost without it.
- Any pomodoro timer alongside a time boxing approach
- I hate Jira (so not gonna plug Jira) but make sure you/your team have one of the new school project management tools and integrate it well.
Podcasts
There are so many good ones, I mostly consume Shopify related ones but there are loads so find ones that matter to you.
Shameless plug but I really loved Kyle Dukta's series on WTFounder Friday I miss those LinkedIn discussions. We need more!
Endurance, Running and Self Thought stuff
- Can't Hurt Me & Never Finished by David Goggins. Not for everyone but they are staples in my life at this point.
- Endure: How to Work Hard, Outlast, and Keep Hammering by Cameron Hanes. Again not for everyone but highly recommended
11. What do you want your legacy, lasting impact to be?
Plant flowers I may never enjoy the beauty of, and trees the shade of which I may never sit in. (context in my answer to question 4 above).
I simply wish to leave this world and the small micro spaces I have been in better than when I first got involved. And as a lasting impact I would like to see more people follow empathetic human first approaches to building companies and products.
