James Whelton: “I was in this never ending cycle where, after I’d achieved one achievement, I’d need to get another. I was addicted to that stimulation“

In a candid exclusive interview for The Currency, James Whelton talks about:

• How computer coding class organisation CoderDojo, which he founded, began

• Building the Danube app for a Saudi supermarket group that has enabled millions of people in Saudi Arabia to shop on their smartphones

• How he can measure his life in the number of times he’s ‘burnt out’

• Being diagnosed with ADHD, and subsequently taking Ritalin to help him focus

• What led to, and how he got through a ‘quarter life crisis’

• What he might be planning next

*****

It’s late July, and James Whelton is a month away from turning 27. He has suggested we meet because he may not be back in Ireland for some months afterwards, and our interview takes place over coffee in a Dublin hotel.

It’s mid-morning on a weekday, and the room steadily fills up and the hum of chatter increases in the background as lunchtime approaches. After our interview, he will catch a plane to Berlin, where he is catching up with friends, before going on to Japan, mainly dividing his time between offices there and San Francisco, as the private equity firm where he has been working, though has since reduced his workload down to one day a week.

Midway through our chat, one of the hotel’s staff comes to hoover some of the couches, and around them, so we pause momentarily until she’s finished.

But the Cork-born son of two dentists also pauses momentarily to read a message from one of his sisters, who has received some exam results.

He has two older sisters, and one younger. ”In my time off last summer, I had a vicarious J1, where I went out to visit my little sister for a while in the US, in Newport. I ended up sleeping on a couch in a house that I think is normally supposed to accommodate four or five, but it was accommodating 15 of us all together.

“Thanks to the two older sisters, I could apply fake tan before I could kick a football,” he laughs.

Whelton tells his story here largely in his own words, easily prompted by my questions, but some detail in italics has been added for context.

*****

John Reynolds (JR): Before we talk about CoderDojo, and much more besides, I have to ask you about something that happened when you were 14, this was in 2007 I believe. 

You got a call from a panicking neighbour whose young nephew had just been diagnosed with a tumour behind his eye. 

A scan of his brain that would also reveal the exact location of the tumour had just been done, and doctors in the US needed it within 24 hours, but the broadband was too slow for it to be sent in time. 

You quickly wrote a software app that allowed the doctors in the US to view the brain scan over the internet. I gather that it enabled them to determine the correct surgery and treatment and today that child is alive, although minus one eye.

Can I ask you to talk a bit more about that?

James Whelton (JW): The heart of the problem was the nephew’s father was trying to sending a sizable amount of large image files of brain scans to doctors in the US over email, for a second opinion as quickly as possible, given the nature of the situation. 

The email provider he used back then had stringent attachment limits along with poor upload speeds, so he was encountering failed uploads for a myriad of reasons. 

I gave him access to my web server and coached him over the phone how to upload the files over FTP to it, which was a more robust method than trying to send the files over emails. 

I hacked together a web based file viewer, so the doctors could receive a link and browse through the files, to try and make it easy as possible to access and ultimately provide their opinion. 

The images were finished uploading in the early hours of the morning and the link to the file viewer was sent off. I felt extremely sorry for the child and family who was dealing with that and did my best effort to help. 

These days one could accomplish the same using Dropbox or Google Drive, of course. 

That was a salient experience for me at a young age: it illustrated how the things we can create can be helpful and meaningful to people at their most vulnerable times.

JR: Can you tell me how Coder Dojo began?

JW: I started designing websites when I was about 9, because I had been playing around and learned how to make animations on the computer. I just spent a lot of time like using Microsoft Paint and then I’d bring them into Windows Movie Maker and then figuring out that you could make them move. And then I thought that the world needed to see that.

I saved up my pocket money, and then bought a book on web design. That was the catalyst for making apps too, and I continued all through secondary school. But the very annoying thing was that I was academically very poor. 

I wasn’t sporty, nor was I particularly artistic, nor had any other kind of musical or any other talents one would recognise in class. This was quite frustrating: the thing that I was good at, really enjoyed and passionate about – there was no outlet for it.

But it was around the time that Eircom had ran their Golden Spiders Awards. And I entered a project that was a Leaving Cert site that had content including a countdown, and a points calculator, and all sorts of resources. 

Then I made a Twitter bot to accompany it that would find students tweeting about the Leaving Cert, and read back the exact amount of days, hours and minutes and seconds left until the exam, just to really freak them out. It was instead of a video that someone sent to me that was designed to scare people into studying.

That won the Best Web Design award in 2010. I won the small pink iPod Nano – the first generation. I messed around with it for the weekend and and figured out I could modify and config files and get past a few things and do what it wasn’t normal to do. This was at the age of just 17.

The Apple fanboy populace of the internet then put their hands up and rejoiced. So in school, there was a bit of notoriety around that. It was kind of the classic news story of you know, ‘Schoolboy hacks Apple.’ There’s probably a very pretentious picture of me wearing a school uniform holding a laptop. 

But because I was so academically poor, people in my school heard this. And they said, well, if  that idiot Whelton can program, surely we can. That was when people actually came up to me and asked ‘how do you hack?’ Or ‘how do you make games or apps?’

With permission of the school, I got together a group of people after an announcement seeking anyone who is interested in learning this stuff. 

There were about 40 pupils. So, twice a week, I taught two groups, after school, how to build apps and websites. So my set of experiences was, one, being academically extremely poor. And two, I had participated in self-teaching and learning online.

When I looked at how some computer science was taught, or just general programming, as a first year college student, I might build a mortgage calculator or something that doesn’t particularly resonate. I guess, theoretically it might be important. 

But our premise was to build projects,  websites and games that resonated, and then have a lot of fun. If nobody could come up with an idea for what website to build, well we’d ask them to build the worst website they could conceive. It was a thing that I enjoyed tremendously and wanted to share that. We’d be in the classroom all day. 

“I became a very anxious individual. So you were kind of in fear of it, and worrying. I always sort of overworked, which is very much what you do when you feel what you’re doing is a noble and righteous thing and you care about it deeply.”

At the time, there weren’t these kind of larger notions of  software is eating the world. And this is the new language. Nor was it about this massive economic requirement and this is skillset of the future. We were saying ‘this is mad craic’

Once people from from my after school clubs started going home and showing their friends what they were doing, I had students from other schools contacting me saying, ‘I want to come to your school after my school, can you show us?’

Around that time, towards the end of sixth year, in 2011, I was invited to speak at the Web Summit. I missed my Latin mocks, much to the disbelief of my Latin teacher, because I was failing. But a signed note from my parents change that.

Latin was specifically my very worst subject, because it was actually…the concern was me failing. So it was funny that of all the ones that I could miss, it was  my weakest one.

I was kind of adamant at the time that I was going to stay in Cork and go to college there. After my Web Summit talk, a number of people recommended that I should meet Bill [Liao, an Australian entrepreneur and venture partner with Sean O’Sullivan’s SOS Ventures].

He’d had a tech background, been an investor and done several startups. And I met with him for two or three minutes in a hallway initially.

A few weeks later, we met up in Cork. Bill had been had been a programmer and done quite a lot. What also resonated with him was the fact that this was the new literacy, and that there was such a demand for programmers and talent in this space. There was a shortage, and he could really see a lot of those macro trends.

It then became a lot more profound than just a fun activity. He suggested that maybe we could find a free office space so that we could run these outside of the school. We picked a date without any name. We just knew that we’re going to run a session somewhere. And that’s how the first one came to be.

I remained involved then for about three years, and in that three year period, we had a lot of growth, a really fantastic community that came around, and that really evolved it. And I think with Coder Dojo, we wanted to create this open source approach. And that really, the community would take and contribute back. And there’s been a number of incredible leaders who have equally defined Coder Dojo, and the Coolest Projects in the RDS,

It was started by three members, and that now is a major event. And we’ve had a number of initiatives to increase diversity, encourage girls to code and that kind of thing. There seemed to be a bit of a peak of interest in the subject in 2011.

There was definitely a degree or luck with timing and an appetite for knowledge about it. Towards the end of Coder Dojo, we had four people running it, but I had been getting quite burnt out for a number of reasons. 

One was that as a 21 year old, I didn’t know how to look after myself properly. These were the classic things of not exercising, not eating a proper diet, or, on a regular basis, ordering a Domino’s pizza at 1am and having a huge carb spike and then crash. Or habits of like, instead of washing clothes, just buying clothes, like t shirts from Penneys.

I became a very anxious individual. So you were kind of in fear of it, and worrying. I always sort of overworked, which is very much what you do when you feel what you’re doing is a noble and righteous thing and you care about it deeply.

“On one hand CoderDojo is very precious to me: I wanted somebody who knew what they were doing to take it to the next level”

It’s easy to push yourself to those extremes and you have a lot of cognitive distortions. Instead of the mindset being, I should do this sustainably and I should take care of myself because I can have a greater impact, your mindset is more, if I’m not working, then I’m not giving my all and therefore am doing a disservice. I was a classic first time entrepreneur, so definitely had burnout and poor health.

I think that spilled over into my work where I’d work until 5am or 6am, or a number of times I did like the full 24 hour cycle. I’m the only person to have a ban on sleeping at the old Dogpatch Labs at Grand Canal Dock. Back when they accepted Coder Dojo in there, I didn’t actually have a place to live.  

I eventually had a colleague of mine say, ‘look you you know this isn’t sustainable, you have to go to a psychologist,’ and he gave me some contact details. I saw a psychologist for a number of weeks and did sessions to work through and dismantle that kind of web. 

And then around the same time, I’d also been feeling that with the foundation, maybe around that point being two years old… and four people working there and however many hundred Dojos at the time, it needed governance, needed someone to set KPIs and strategy. We had donors and funders who,’d say that the reporting on and measurement of this is quite important. 

On one hand CoderDojo is very precious to me: I wanted somebody who knew what they were doing to take it to the next level. There was a foundation aspect that is, so the foundation and the community always maintained separation, that if the foundation were to die without funding, then the community would be unaffected. 

*****

By 2012, Whelton had been awarded €300,000 in funding from Social Entrepreneurs Ireland, and Ashoka Ireland. He was the youngest ever recipient of the coveted Ashoka Fellowship, which was announced at the Dublin Web Summit. Previous recipients had been Wikipedia’s Jimmy Wales, and Grameen Bank founder and Nobel Prize winner Muhammad Yunus.

The Web Summit audience that year were wowed as Whelton was joined on stage by several young prodigies expounding their knowledge and entrepreneurial spirit.

Among them were Harry Moran and his brother Con, creators of Mac app Pizzabot and a website to encourage tree-planting called Crainn. Also there was Shane Curran, interviewed previously here on The Currency, and who has gone on to found data privacy startup Evervault.

CoderDojo had gone global, with new ones emerging in Jamaica and Africa. Every Saturday afternoon, 104 of them took place: 41 in Dublin and elsewhere across Ireland, attended by up to 6,000 keen young minds; the others in a host of cities including London, LA, Tokyo, San Francisco, Chicago and New York. They had one rule: ‘Above all, be cool.’

*****

JW: It needed somebody to take the foundation, structure it and really drive it forward. And myself and Bill had been very good about articulating things in a charter and vision. And there’d been a number of different ideas on how you can do recognition through belts or the philosophies that have been well documented. So someone could execute and talk about that. 

And from a personal perspective at 21, I knew there were other things I wanted to do. I loved programming, I loved building. And I wanted to actually go and I wanted to go in and build tech.

And so I stepped away, and an executive search began and we ultimately hired Mary Maloney, who was at Accenture for years – she’s now at Teneo. And Giustina Mizzoni, who’s been at the foundation from the very start, then became the executive director. [She announced this month that she is to become a director of strategic partnerships at the Raspberry Pi Foundation, with which CoderDojo joined forces in 2017.]

Polaris Ventures, which started Dogpatch and had been a big supporter, gave me an entrepreneur in residence role. And I spent a few months in Boston, and it gave me that break and perspective so that I could get myself back into a place of good well being, where I wasn’t fraught with concern about CoderDojo.

*****

Today, CoderDojo is run by a team in Dublin. There is an annual DojoCon conference for the volunteers from all over the world that make the Dojos possible, while this year, three Coolest Projects events, where young people can showcase their creativity, entrepreneurship, coding ability and tech skills, will take place in Manchester, California and Dublin.

More than 9,000 volunteers around the world are involved in running over 1,900 verified Dojos around the world in 93 countries, putting in over 300,000 hours of their time.

*****

JW: While I was looking at what to do next,  it became very quickly clear that I still had a lot of skill gaps. So I decided that I needed experience. 

At that point, I went over and spent time with a mentor, Jonathan Siegel, [a serial entrepreneur and investor who backed Intercom and Dropbox,] in Santa Barbara.I was trying to figure out what life would look like and what to do. 

JR: And how did you how did you come to pick Jon as your mentor?

JW: Jonathan had a technology background. He’s a very accomplished programmer, and someone who did it for the love of it. But then he also is incredibly commercially savvy, and had built and sold organisations and done quite well. 

While being very successful in that respect, family was very important to him too. He also enjoyed flying planes and a whole host of activities. 

Paul Kenny [the serial entrepreneur from Galway] was over visiting him at the same time. As it happened, we had been due to meet at an event a year before that, but Cobone was being acquired at the time, so he had cancelled. 

We were chatting away and he was telling me that in Dubai, there were corner shops or grocery stores, basically at the foot of every apartment building.  And you could ring down to them directly and order up. You could just tell them what you wanted, and somebody would drop it upstairs. I just found that level of comfort and access pretty phenomenal.

We hacked around with an idea and we built this on the drive from Santa Barbara to San Francisco, which is maybe like six hours or so, like a little app that you could have, would have like the top 20 most popular items: a can of Coke or a bag of ice or something, then you would do a you’d select, it would do a robo calls to a number, call out the items and then press one before accepting, and two for deny. And I was first playing around with an experiment. 

I’d spent a few months in the States by then. That seemed to be the default at the time: after Ireland, you go to the States. And the Middle East seemed interesting. It’s a different tech landscape and different dynamics from from the west.

Paul told me how Cobone needed a CTO. They were about three or four years old at that point, and that they’d been acquired once, they had around 100 people. And they were a very functioning business; yet  there’s opportunities to optimize and improve aspects. They had another travel product. 

I said, ‘I have these gaps that I need to learn. But I think that I can add value on the technology side. Paul said that we can plug these holes.

So after I’d known Paul for the three days, I got on a plane and spent a week interviewing with the management team of Cobone. They offered me the role of CTO, which at 21 definitely led to a considerable impostor syndrome. 

But fortunately I was able to add value and implement a number of processes and optimisations, solving the problems they had.

That shift in perspective was very important for me. I’d come from a background of impact, and in charities, sometimes the KPIs could be a little bit more difficult to understand, like, ‘how many imaginations did we delight today?’ That’s definitely hyperbole. 

But the transition from where the qualitative metrics might be the impact on a person’s life, compared to quantitative, such as dollar spend.

It was refreshing because now there’s a very clear line as to whether we’re making money or not. Secondly, I got to work on tech and build well-established product and production systems at scale, with a very real risk of breaking stuff.

The shift from like CoderDojo to the Middle East was important in terms of the introduction of KPIs and deliverables and this whole realm of everything being bottom line driven, and seeing that world. 

Secondly, I was getting quite a lot of executive coaching; learning different management systems. Things were also a lot more blunt, however. Either I was succeeding, or I was not. What that meant was working hard, and long hours to get through it. 

Also when I went to Dubai, I was more than broke. But then, for the first time, I was earning good money, and able to build up some savings, and give myself a bit of financial security.

At CoderDojo I’d gotten a stipend and put myself on what at the time was the national average salary: about €35,000 a year.

After a year, Cobone was acquired again, changing hands from Tiger to the ME Digital Group. And then for about a year and a bit, Paul and I explored different ideas.I became a partner in an online flower store. We looked at doing a kind of a Casper; a mattress and pillow company. 

I really refined and got quite a lot of appreciation for the tech and systems behind ecommerce on both the consumer facing side: the catalogue, all the different funnels, from checkout to customer acquisition funnels. 

And then the processes that underpin it, from operations, customer service, and so on. I became very passionate about that world. I looked at every single ecommerce system out there, look at their code bases to see the differences. 

After that period of experimenting, we met the Saudis and had the opportunity to form AYM, bringing the largest chain of supermarkets in Saudi Arabia online, which was quite remarkable for a few reasons. 

It involved very hard problems, that not just we would be responsible for bringing 16,000 products online. But also the operations behind it, from customer service to picking and packing  to delivery. It involved complex logistics. 

“I’d also consulted or advised companies who were scaling up and building out tech. The Irish tech community, particularly from 2011 onwards, was just fantastic.”

On top of that, you’re building things that are, both left to right and right to left. I took Arabic classes for three months, two or three evenings a week. By the end of it, I was, I was sure I could copy and paste correctly. 

We took about four or five months to build that tech: the consumer facing apps and the back end system.

JR: Would you say you built a lot of your expertise through self education?

JW: On the technology side, when I came to Cobone I had been through CoderDojo, I’d done some moonlighting or side hustles: for example, I built the first Dublin Web Summit iOS app.

I’d been friends with Paddy Cosgrave, and slept on his air mattress for a while. I used to hang around the Web Summit office and just work on different projects for him. Then I built CoderDojo’s own systems for managing Dojos. 

I’d also consulted or advised companies who were scaling up and building out tech. The Irish tech community, particularly from 2011 onwards, was just fantastic. 

Danube got built in five months, along a very accelerated timeline, with lots of iterations. Towards the end of it, I’d learned that I could push myself quite hard. In the 10 weeks leading up to launch,I was doing somewhere between 18 to 20 hours a day, working across three time zones: the Middle East, Europe and South America. 

This was a supermarket chain with processes that needed a lot of problem solving and integration. By all accounts, building that system out in that four to five month time period – compared to other people who’ve now been bringing bringing supermarkets online – was extremely fast. 

I’d have calls with the team in Europe, and in Mexico about something we had planned, and then go and work through the night with them. Then, at 9am, I’d show the feature and talk about it. Then go home crash for maybe four hours, and get up to face that all over again. Ramadan was coming up, and that was kind of a key deadline date. 

JR: So, how many how many people overall were you managing? 

JW: Between design, front and back end, mobile, we had a team of 20 people working with us for for a number of months. I also worked closely with Paul at all hours, as well as with our Saudi colleagues.

All the time, we were trying to move at a velocity where everything also has to be exactly mirrored right to left and then in Arabic.

The degree to which I was pushing myself involved drinking copious amounts of Red Bull. I can measure my life in burnouts. I was also getting through a packet of 20 cigarettes every two days. I don’t smoke any more. So, 10 a day, but it was a lot for somebody who didn’t really smoke prior to that. 

JR: How many cans of Red Bull do you reckon you were getting through in a day?

JW: There are definitely pictures on my group chats on Whatsapp of three or four cans and the sun rising. Bear in mind that the context was I was a young person who didn’t have a family or responsibilities like that. I noticed that as equally exhausting as it is, it’s exhilarating. It’s not necessarily something I want to do again, but I’m thankful that I did it.

We got it launched. All systems went  live, everything was stable. The next kind of few months were  optimisation and growth. But at the same time, I had gotten better, to some degree about burning out. 

Perhaps after we launched though, that survival mechanism began to wear out. In the run up to the launch, because you’re in hyper care mode, you’re checking everything, seeing responses, you’re unearthing all these edge cases and things that you didn’t know or couldn’t possibly imagine as you’re building the system, and you have to be responsive. 

I got quite burnt out then, but I staved it off a bit more through, either nicotine or my prepared meals – I had three meals delivered each day. So at least I was eating correctly. 

Gradually I began getting more sleep and also became a bit more active. But it wasn’t enough to keep at bay the feeling of being burned out. I couldn’t keep focused, and got a bit fed up with that.

I went to a psychiatrist and, at the tender age 25, I got diagnosed with ADHD. In a way, it was very, very convenient. Because I got a prescription for Ritalin, which I chose to try, it kept me going at a time at a time, and meant I wasn’t redundant [in terms of my role at work].

I’d had such hunger and ambition. But also at the time, I felt a lot of…maybe this is a factor of the CoderDojo stuff. When I was young, I felt that a lot of people put me on a pedestal.

I had this mindset that I was expected to do something successful in tech. I had to actualise that status…

JR: You felt pressure to succeed? 

JW: Exactly, but it turned out it was largely in my head. A large part of it was a belief I can’t burn out. But it was all wonderfully solely in my head, 

I’ve talked about it to a lot of friends online, who’ve been entrepreneurs and founded startups, and they’ve either been successful or hasn’t been successful,  and I think many people do feel this same pressure.

There’s also an element of insecurity though: you don’t want to appear that way to your friends and colleagues. You want to be the same as the narrative you present on Instagram: I am or I’m going to be a successful tech entrepreneur. 

JR: It’s a common question to ask entrepreneurs where their drive comes from. Sometimes, people take after their parents or it seems a genetic trait. In others, it seems to emanate from something in their childhood or certain insecurities. Others seem just incredibly naturally driven to create…?

JW: Yes for some it’s just their nature. I definitely am driven to create. Tech puts youth and utility on a pedestal. But then you can contrast that with the fact that the majority of successful startups are founded by tech entrepreneurs who are in their 40s and college educated.

If you take a look at companies that create real impact, more often than not, the founder is somebody who’s had six or seven years experiencing a problem working in an industry, but sometimes they’re not the ones that we see dominating the media headlines. 

I recall reading about various people who are in tech, and all the glamour of it, and feeling that people would have compared me to them. One way I had of dealing with that would be that I had a ritualistic period of two months in Cork, playing Fortnite, hanging out with friends, and being shut off from the world.

Reflecting back on my AYM role now, I realise that I got through the mental indigestion. I pushed myself, I was very driven and it definitely was a lot of fun. It provides a lot of data points too. 

But I also know that I wanted to do well by my colleagues, I want to do well by myself, and my ambitions. I felt an underlying sense of, almost, obligation to do it. 

“By then, I’d changed my lifestyle to reduce the amount of cigarettes, but was also keeping a burnout at bay. I was exercising quite prolifically. I was running 10k’s or 5k’s at the weekend.”

We went from building the sysem to a point where our apps had a million-plus downloads. We had got a group of supermarkets online [in Saudi Arabia], and we were processing and delivering a substantial number of orders a day. 

It was a very big win. And, as a technologist, I still felt very self actualised. I’d ticked a number of boxes in that I had built in and like our app is, in the top 10 in the app store in the Middle East. 

We had a high number of reach and downloads. We were moving bits to atoms, as the expression goes.

I kept on working quite hard. I was making a good amount of money, and had built up some savings. I felt quite secure. I think I had gotten to a place then where I had turned 25, and had been four years out in the Middle East. 

By then, I’d changed my lifestyle to reduce the amount of cigarettes, but was also keeping a burnout at bay. I was exercising quite prolifically. I was running 10k’s or 5k’s at the weekend.

I had a better work-life balance, in an extreme sense, but there was no buffer. I was in this kind of hyper optimized stage, where I was incredibly productive, and getting up early and on the meal plan. I was beating new times on my 10k runs. I was fitting it all in. But it was that pace that was unsustainable. 

It got to a point where Danube was stable, and we had a team at AYM that was taking on new projects and doing deals with other firms. We had a number of other things in the pipeline: we were a typical growing company. 

But I felt that I wanted to take time out because I still couldn’t get past the feeling quite burnt out and I was becoming a bit more zonked in work. 

*****

Two million shoppers would go on to use the Danube app after its launch in 2017, and it has won a number of awards. The user base is now approaching 3 million, according to a spokeswoman for AYM, which is but one legacy of Whelton’s technical genius.

During Whelton’s time with the firm, “AYM Commerce has been fortunate to have significant experience with the rollout of a global loyalty platform for a leading European consumer products group, where integrating multiple existing & new technologies in a manageable way was one of the key objectives. 

“De-mystifying this technology stack within a much larger eco-system enabled cross functional teams and co-ordinated execution across multiple markets across the world. We have also worked with one of the leading food delivery companies in Europe to implement their ‘mobile born’ customer engagement platform across 3 key markets, underpinning their real time one-to-one consumer communications,” a spokeswoman for AYM said.

*****

JR: Were you still on the Ritalin at that stage, and are you still on it now?

JW: I’m not on it now. But basically when I left Dubai, that’s when I stopped it. I quit cigarettes as well. Although I’d be lying if, if if I hadn’t been spotted once or twice in a pub smoking area. And I said, well, now, I’ve achieved everything that I wanted to achieve. I’ve been out here for four years, I do miss my friends and family and haven’t spent enough time with them. 

I just wanted to take time out. I had been thinking a lot about what drives me. Being only in my mid 20s, I was also asking myself if there were other places I wanted to live, or things that I wanted to do.

JR: Was it maybe a quarter life crisis?

JW: Exactly that, yes: the quarter life crisis. And, I guess like every quarter quarter life crisis, you think of your own mortality.

And you’re like, well, do I wish I’d spent more time with my family and parents. I was thinking about monetary want, or status, and what it was I really wanted. I wanted to deconstruct that a bit, asking why I was constantly doing the fun things at the weekend, despite being pretty exhausted. 

I was actually pretty terrified. But I had an incredibly supportive team. I’m trying to think of how I phrased it, but I basically said that, at the moment, I’m not all there. I told them I was exhausted, living a life of extremes and that it wasn’t sustainable. I explained there were other things I wanted to explore and do as well, but that the larger part was the exhaustion and mental indigestion.

Afterwards, that manifested in the two months I spent in Cork, not getting out of bed before midday, except maybe twice, I think. 

But I also found that our Saudi partners were actually very understanding about my situation. In particular, everything largely out there is about family business and it’s all extremely relationship driven, so when it’s on the premise of like, spending time with family and friends and all those things, they appreciate that. But I definitely had trepidation about that aspect of my decision before telling them.

“So I’d stopped smoking, I was off the Ritalin, and then I began experimenting with not drinking for about two months.”

They had an appreciation that running a business is hard. From their point of view, they wanted to make sure that if somebody is doing it, that they’re putting their entire heart into it. 

They got a new CTO and VP of tech.

From there, it was quite a quick transition. I went home and spent two months, playing Fortnite and hanging out with friends. It was a relief not being on call. I remember the first day, that 24 hours went by without my getting an email or WhatsApp or something meaningful like that. And it kind of marked it as quite a large departure for me, from that chapter in my career.

The other thing I’d gotten was more of a perspective about who I am. I came to better understand myself. I’m a glutton for optimisation. I wondered about the things that I could only maybe do in my 20s or late 20s. I didn’t want to have this situation where I had missed out on those things that would be important to me.  

So I’d stopped smoking, I was off the Ritalin, and then I began experimenting with not drinking for about two months. Not that I was drinking heavily prior to that. I was also catching up on my sleep: I had periods where I’d be sleeping 10 or 11 hours a night, because I could. I ended up figuring out that to be at my best, I need nine hours of sleep.

JR: Was it a huge difference, from being on Ritalin, and then not being on it?

JW: The way that I would describe it is that… Ritalin makes your brain produce more dopamine, so every every task that you do, you get a sense of reward from. There are three types of ADHD. I got diagnosed with a combined type, where either I can exert hyper focus on things that interest me, but the things that wouldn’t interest me, I would get no satisfaction or joy from. 

I remember, there was one period where I spent 30 hours building a Saudi mapping system. Saudi doesn’t necessarily have addresses, Arabic is a language has no vowels. The a’s, e’s i’s, o’s and u’s more or less interchangeable. As a result, there’s very little consistency. 

I built the core of that system, or majority of it, in about 20 hours. I was able to really zero in on a task. But at the same time, I was bad at routine things. 

With Ritalin, every task that you do it’s very easy to you get dopamine, it is very easy to get through things very efficiently. And when you’re doing a task, you think about doing the next one.:when you have a defined set of work, it’s very straightforward. You see it in college students who abuse stimulants to write long papers and essays, so it lends itself very much to that. 

What I found and others have found is that it kind of curbs aspects of your personality, and your creativity. But when you have all this dopamine, going through your body, you can become more irritable, or more direct with people.

But I preferred myself when I wasn’t on it, and my friends agreed. My normal personality is what I valued more. And it’s more sustainable, because you don’t have peaks and troughs. Conservator, which is the typical long release one, has a 12 hour release, but then you kind of crash when you come off it. 

“I also went to the Arctic at the end of August. That was very interesting. And for the first time in recent years I was offline for a whole four days. And when I came back online, nobody really cared. That was very sobering.”

But, I think when you become an entrepreneur, and a lot of your tasks are related to whatever you’re working on, and inherently are what you’re interested in, or you’re working with people in a similarly collegiate environment, it doesn’t become as necessary. 

After coming off it, I also worked a lot on developing good systems for myself. I follow Dave Allen’s ‘Getting things done.’ I also use a series of processes and task management apps to help organise myself. 

I also went to the Arctic at the end of August. That was very interesting. And for the first time in recent years I was offline for a whole four days. And when I came back online, nobody really cared. That was very sobering.

I then spent three months backpacking around Japan, and reading and writing every day, being very reflective.  It all brought me to a point where I could better understand my values.

Money and resources are important to me, But they’re not ultimately what drive me. Instead, I found that, you know, improving people’s wellbeing is incredibly rewarding. 

I realised that I’d lived a lot of my life previously, as entrepreneurs do, looking at the end destination, the goal and that everything, everything you would sacrifice or do was in the name of that. But in fact, it’s very difficult to control that…so what you can only really control is the day today. The here and now, if you like.

So I identified that what I wanted to work on day to day after that point would be something that would respect that anything monetary, or, you know, recognition, or these things that people crave had to be secondary. 

But I also reflected on the fact that I’ve gone from a place of extremes, from an extreme kind of the charitable,  nonprofit organisation, which I left feeling very burnt out, to an extreme capitalistic one, which also left me very burnt out. 

So I kind of realised that maybe that materialistic pursuits in themselves aren’t sustainable. I was in this never ending cycle where, after I’d achieved one achievement, I’d need to get another. I was addicted to that stimulation. 

In a way, when taking time out from work, I even found that when I was travelling, I adopted a similar kind of approach. I’d look up one of the top 20 things I could see or do in my destination, but then it became a challenge, where,  boom, boom, boom, I’d go and see them all. 

I also began asking myself, well if I had all the resources in the world, what would be the kind of things that I’d want to do? And definitely I’d want to travel and spend time with friends, and what have you. So I’m doing that now. 

And then, early in 2019, I began working in private equity with Jonathan Siegle, with his firm Xenon, which is giving me some great insights. I’ve enjoyed collecting data points. 

Since the beginning of last year, I was kind of feeling the lust for life again. And now it’s time to do something new.