To Be Interesting, Be Interested

I had this strange realisation one day — it had been building for a long time, back when I was doing my A&E rotation. Once in a blue moon you clear the A&E waiting room at one in the morning, and then you come back the next morning and it's full again. There's something so inevitable about that. So I had this itch to understand who's trying to go upstream, who's trying to solve that problem. Gradually that evolved into learning about products, about services, and a growing interest in technology.

After my F2, I took a gap year and did a public health degree — I went to Boston for a year and had a really good time. The thing that really caught my interest there was what was happening at the intersection of the medical school and the business school. There were startups being created by students — some of them MBA students who were doctors, others on my course. A few of those companies have actually done very well now, seven or eight years down the line. I saw something very exciting in that, and I started looking at technology, at businesses.

When I came back to the UK, I entered ST1 ophthalmology, because I'd already been accepted — but I had this thought in my mind: how do I get my hands dirty in business, in technology, in creating companies? So after about six to nine months of ST1, I resigned. That's a longer story we can dig into if you like. But I handed in my number, and I joined a consulting company called McKinsey.

The main reason I joined McKinsey was that, more than any other company I was aware of at the time, they told this great story about transformation. You come in as a doctor, a scientist, a lawyer, and they really develop you — your intellectual skills, what it's actually like to solve business problems. You meet lots of clients, you're solving problems in different geographies, different domains. I was hooked. At the heart of it, I was just really hungry to learn.

So I joined McKinsey, spent three years there, 2015 to 2018. In 2018 I left and co-founded a telemedicine digital health company. That was with someone I'd met at medical school — I'd got involved in a project in Somaliland and the Middle East, and the guy who founded that organisation was a good friend, a very dear friend, Alexander Finlayson. We co-founded Nye Health together at the beginning of 2018. For the last three and a half years, more or less, I've been at Nye — helping grow the company, working on the products, doing the fundraising. As a co-founder you do a bit of everything.

About two months ago, I left Nye. So that's the narrative summary of what I've been up to since medical school. Right now I'm doing a mixture of things: working with a few startups and some pharma companies on contract work — helping big companies learn how to work with startups, and helping startups understand the problems big companies face. And supporting a bunch of other startups more informally, in some cases making angel investments.

Honestly, it's all of the above and more. Let's get the bad stuff out of the way first. You work really hard when you're working, but you do have downtime — they call it being "on the beach", when you're between projects, and things are pretty chilled. But when you're working, you're working really hard. Having said that, in three years or so I think I did one all-nighter, and I virtually never worked weekends, apart from maybe one or two days. So it's a trade-off: you work hard Monday to Thursday, sometimes Friday, and then you have your downtime.

Some of that work is travel. There were times I'd wake up at four in the morning, catch a 7am flight to Chicago, land at 10 or 11am local time, work until 11pm local — by which point it's some ungodly hour on my body clock — then fly back on the Thursday, sleep overnight on the plane, turn up in London at 10am and do a full working day. I did those kinds of stints, which in hindsight were just crazy.

On compensation, I'd say: don't go to McKinsey for the money. It's hard work, and if you're just motivated by money you could probably get paid a lot more elsewhere. McKinsey has this sense that they don't have to pay top of the market because they've got a strong brand — and what's happening in other domains like technology and investing is on a different level anyway.

But the key things are two. The first is the learning. All that hard work leads to something — you're sharpening your sword. Making slides is a bit of a joke, we can poke fun at people who "just make slides", but there's a real art to communication in business, and that's what you're learning: ownership, delivering to a really high standard, getting things done on time, simplifying complex ideas. And a lot of it is in Excel — quantitative analysis, modelling. You're in the kiln, in the furnace, learning in the process of doing the hard work.

The second thing is the people. McKinsey is full of very motivated, very talented people. People used to joke about "hyper-anxious overachievers constantly needing validation" — it's a bit of a joke, but there are a lot of very smart people, and the intellectual tempo and horsepower in those teams is extremely high. You form real bonds, you build great friendships, you learn from people. In my case many of those friendships have continued since leaving the firm. It was a real thrill. It's addictive in the way that doing anything at a high level is — that always-on mindset gets a bit addictive.

It's a great question, and I do recognise it — I've been very blessed in that regard. I think it's a combination of things. In virtually every case, I had a friend, a mentor, or someone I looked up to who had done that thing before me. At Oxford, there were a couple of students in the years above me at school who I really looked up to, who'd got into Oxford or Cambridge. With McKinsey, there were classmates of mine in Boston who got in. With the Fulbright, the year I got the award I was living in a flat with a guy called Adam Ali, who'd had a similar scholarship a year or two before. Alexander, my co-founder, got a Kennedy or Knox scholarship to Harvard a few years before I applied.

So the people around me — their experiences, their ambition, their horizons — being able to see those opportunities was critical. In many cases those people literally wrote my personal statements with me, or wrote references, or guided me through the process. I was just extraordinarily lucky.

There's another part, of course, which is that you ultimately have to put the work in — interview preparation, McKinsey's entrance exam, and so on. I do have a tendency to get really goal-oriented at times. You can think of them as sprints: if there's something I'm working towards over a three-to-six-month period, I'll be really focused on it. And I just work hard — I do my best to, anyway; it's difficult, there are lots of distractions. So it's a combination: having people around to give advice, support and training; following what they've helped me see I need to do; putting the work in; and then a huge dose of luck, which I don't want to discount.

One of the best things about that process was starting the company with an old friend. Having now seen hundreds of companies, maybe more, one of the greatest challenges is finding good co-founders — and by good I mean a good fit, not that some people are bad. I was very fortunate to have co-founders I really trusted, who I'd known for a long time. That took a lot of the anxiety out of it — it's like doing something with your friends.

In terms of the business, we were doing telemedicine with the intent of building for the NHS first. That's why we called the company Nye — the politician who brought the NHS into being was Nye Bevan, the Welsh minister. We wanted to build telemedicine for the NHS.

In the first instance, we got a lot wrong. We were able to raise money reasonably easily — the first round was largely from NHS people, GPs and partners, an NHS institution, plus a few non-medical angels. But one thing we really struggled with was getting traction. I think that's normal, actually — a lot of people start somewhere, and the first thing they put out isn't quite the right thing. So we iterated through many, many different products. Eventually we found something that really worked — and the great learning was that the thing that worked was the simplest thing we'd ever built. It was maybe 10% of the 100% we'd conceived and built, and that 10% was the thing that stuck.

Through the pandemic, when it kicked off in the UK in March 2020, things really picked up pace. We were growing 10 to 15% every week for about 60 consecutive weeks — the company was doubling roughly every five to six weeks in its user base, its usage, its reach. That was a hectic time. When you're building something growing exponentially, everything breaks and falls apart; it stops being fit for purpose. You fix something, and because you're now five times bigger than when you last fixed it, it breaks again. A real whirlwind.

When things stabilised, the long and short of it is we pivoted out of primary care and more into the research space — partly because of what competitors were doing, partly the challenges of commercialising in the NHS, which is a real challenge. A few companies have cracked it well, but many struggle. In research we were working with clinical trials, providing solutions that let you participate in a trial from home — that's what the company's still doing now.

About two months ago I stepped back, for a variety of reasons. I'm taking some downtime, working on a few small projects, but also exploring ideas to start another company. It's almost like being a first-time parent — you make so many mistakes, you're more anxious than you need to be about everything. But once you've done it once, you want to see whether you can do a better job the second time, apply those learnings. That's something I'm really excited about now.

There's so much more to say — a lot of ups and downs, a lot of pressure at different times. Raising funding is never a peaceful process; it's a negotiation, process management, relationship management, a lot of technical stuff. If you get it right, you raise the money you expected, so nobody thinks you over-delivered — but if you make a mistake, there are so many ways it can go wrong and the whole thing can fall apart. There are a lot more ways to crash and burn than to get it right. Not for the faint-hearted.

That's a great question. A few things come to mind — some of it might feel a bit disjointed and random, but we'll piece it together.

The first thing is: if you want to be interesting, do interesting things. "Networking" is a strange word — it can sound political, and it activates some antibodies in people, around folks who are a bit hacky or motivated by self-interest. The culture I try to embody in my digital interactions is more "win and help win". Politics is a zero-sum game; the way I like to think about it is just making friends. I don't think we're networking, I don't think you're shooting up or down — I think we're becoming friends. We're chatting, getting to know each other. You're helping me because this is cheaper than therapy; I'm helping you because it's interesting to be on the pod.

So the first thing is: do interesting things that you're genuinely interested in — that starts to form the core of your basis for connecting with people. When you reached out to me cold, I could see what you're doing and what you're about. You're a podcaster with a great track record of consistent, high-quality content; you're carving out a niche, building an audience around your ideas, presenting yourself on the internet through your personal website — artifacts of what you've done, your passions. All of that builds trust and tells a story about who you are. It just hits different from "hey man, can I call you to talk about changing careers?" Putting in the work and creating a centre of gravity around your interests, what you stand for, how you can help people and what you want to learn — that's so important.

The heart of the "making friends versus networking" mindset is this: as children, most of us have a very clear hierarchy in our relationship with our parents, and that hierarchy sears itself onto our psyche. As a child you're not on the same pedestal as your teachers or parents — nobody asks you what you should cook for dinner, where to go on holiday, what you think about the news. You get used to being ignored. Then you grow into an adult, but the transition isn't clear, and you never quite shed that complex of being the child in any relationship. So when people reach out — "shooting up", to use your word — they don't think the person they're reaching up to is just like them. They think they're a parent figure, an authority figure. That creates a terrible feeling, which some people call imposter syndrome, where you don't feel you have a seat at the table.

The truth is that everybody is struggling. Everybody's learning. Everybody's figuring it out. If you think about people as friends — like children meeting in a playground, peers meeting peers where they are — that changes everything. It changes your tone, and your beliefs about what you can share with them.

I'm not saying busy people will always reply if you're hyper-confident. I'm saying you need to swing a lot before you hit, and the only way you get comfortable swinging is by not feeling like an imposter — recognising, "I'm going to have to kiss a lot of frogs. I'm going to send 100 emails, write to 50 people, and maybe two will reply. That's fine." A lot of people just don't swing, because it feels futile, or the first three emails get no response. So to summarise: put the work in, find things you're interested in, do interesting things, build that sense of who you are and what you can offer and want to learn. And then go into these opportunities believing you've got a good shot, and send the emails. You never know if you don't send them.

A really good question. I don't have a mental catalogue to hand, but a few things.

First, in the digital era, people who command attention and build huge distribution and bodies of work — 100,000 tweets, 1,000 podcast episodes, companies, products — even if they're perceived as an overnight success, if you dig deeper they've been working hard and consistently for a long time. In any domain, they'll have years of hard, consistent work behind them. There's no real substitute for that.

Second, the people I saw in very senior roles — each of the 20-plus projects I worked on as a consultant was sponsored by someone in the top one, two or three tiers of a global company — the ones who really stand out are very good with other people. They're very people-oriented. Even with a technical background, there comes a point where they're paid not for their technical skill but for their judgment, their emotional intelligence, their relational abilities. It can be hard to remember that when you're in the trenches building products or media, but there does come a point where you elevate out of the trenches into people management and leveraging your impact through others.

Third, some of them have been very candid with me about their own struggles. I wrote an end-of-year note to a mentor today. Last time we spoke, I told him I was going through a confusing time, feeling a bit down about it all — and he told me he was going through something very similar. Literally everything I said, he was like, "I'm going through exactly the same thing," or "I've just been through that." And this is a guy who's smashed it out of the park on every dimension of his professional life. That's really reassuring, because we all have inner voices, versions of ourselves holding us back.

So — a very unstructured answer, I can't even remember exactly what I just said — but if I had to bear certain things in mind: hard and consistent work, trying to be the best with other people I can be, and remembering that everyone's trying to figure it out. I'm used to answering in threes; that's the kind of thing McKinsey teaches you.

Good question. With this guy, and with others, I've just asked them. I've said, "Look, I'm looking for mentorship, advice, guidance, some challenge." I try to be quite specific about the questions I want guidance on, or self-reflective: "This is a thing I struggle with — self-deprecation, imposter syndrome, feeling inadequate." Whatever it is we all struggle with. And then I just ask, "Do you mind having a chat? I really need some mentorship." It's not formal.

Then what I do is set reminders in the future — I use Notion, so I keep notes and drop in a date reminder one month, three months, six months down the line. When the notification comes up, I write to that person: "Hey, you don't need to reply — this is what's going on in my life, this is how your advice really helped me, this is how I've come on since we last spoke. Have a great Christmas, have a great new year." So it's a very loosely structured process.

I also receive some inbound requests for mentorship. At the moment I'm probably spread a bit thin, but instead of having lots of calls and feeling swamped, I now say to people, "Send me a WhatsApp voice note, or a structured email — what you're facing." Then I can get back to them quickly, and without being time-poor I can still give them my full attention for short periods and really try to help.

On the big decisions in my life, a couple of things have consistently helped. The first is recognising when they're reversible. Most decisions in life are two-way doors — you can wind back if things don't work out. Almost anything in the domain of careers is like that. There are very few one-way doors in a career; even leaving specialty training or leaving medicine, you can generally go back, unless you've done something terrible and been fired.

One way to think about it is explore and exploit. Exploration is trying different things; exploitation — a terrible word, but in the model it means that if you're tapping around for oil and you hit it, you start drilling. At some point you start exploiting what you've found. That goes with the one-way-door, two-way-door thing: when you're exploring, you need to explore a lot, make lots of changes, take a winding route to find a fit. But once you've found a fit, you do have to persist with it for some time. It's a judgment call to know whether to keep persisting or start exploring again.

I think people should be patient with the exploration — willing to try more things. Especially if you think of a career now as a 40-to-50-year journey, it's really important not to have those 50 years defined by a decision you made as a 15-year-old about your A-levels, then your university course. A lot of people get trapped in that, and it's kind of illogical.

The second thing is a bunch of small day-to-day decisions. I try to use technology and products to remove the fatigue of certain decisions — booking links, Notion in the way I described. I have digital habits that could be improved too: I was off WhatsApp for a couple of years and it was amazing; I'm back on now and I spend a lot of time on it.

The real risks in big decisions are often not as big as they seem. Most people discount the upside — they think about the downside, but don't quantify the upside potential, and they don't realise things are easily reversible. So they never try. And there's so much potential to remove friction from your day-to-day life with products, though maybe that's more obvious.

Definitely. I'm struggling to remember just now, but let me give you a few.

First, Nassim Taleb's books. It's a bit of a cliché, but I find them very good — particularly Antifragile and Skin in the Game. They're really good for understanding incentives, understanding risk, things that are ever-present in life but not always visible to us.

There's a book by the philosopher Alain de Botton called The School of Life, an excellent book on emotional intelligence and emotional health. And there's a great book on career development called Range by David Epstein, which is about the balance between going generalist versus specialist — Epstein's view is that being a generalist, especially in the modern era, is a uniquely powerful path. It's an advocacy of generalism.

I've read some really good books about class, race and inequality. One is Natives by Akala, the musician — a great book. Another is Roots by Alex Haley, who also authored the Malcolm X biography — one of the most powerful books on the history of slavery. And Austin Kleon's Show Your Work — I came across it via the Ali Abdaal podcast, but it's a very good book, and it really encouraged me to create more content and share it online.

One caveat: for me the transition has been, by and large, very positive — so I'm giving this recollection from that point of view. There certainly will be people who have a rocky transition, whose first landing spot isn't quite right, who have doubts.

My experience is that I haven't often looked back. There are certain parts of being a doctor that I miss — there's something about the professional community and camaraderie in medicine, being around other healthcare workers, not just doctors but nurses and everyone in the hospital. That's quite special, and you could really see it during COVID; it's been a great source of strength for many people in healthcare. I don't mean envy in a negative sense, but it's good for people to aspire to that kind of thing, because it's a source of support.

So I have looked back from time to time, but on the whole it's been positive — even though there have been very challenging experiences, in some ways far more challenging than medicine. Mainly the sense of uncertainty about where you're going. When you walk off the beaten path and try to patch together something that doesn't have clear role models, you can feel lost, uncertain about the future, wondering where your income will come from, how people will perceive your career, what your actual skills are. I have no credentials beyond my public health degree and my medical school — and I come from a paradigm where credentials are your reason to have a seat at the table. So now, if I'm working with someone in a business or creator setting, what are my credentials? What it actually comes down to — which is much scarier — is the proof of your work: your podcasts, your audience, your reach. The actual work you're doing in the world, your ability to command attention. That's a scary place to be, because it's much more uncertain how to make it in this world of entrepreneurship, content creation, angel investing, startup founding. It's very amorphous.

So one thing I've really worked on in the last six months is reminding myself why I left medicine. Instead of entertaining the doubt that creeps in, I try to double down on the intention — which was to help people through content, to build companies that have a positive impact, to back companies doing good things. When I feel doubt, I recommit; I look for ways to get deeper into that, because I recognise I'm still learning, still developing.

A few high-level points for anyone — a doctor, a nurse, anyone clinically trained — thinking about leaving clinical practice. There are tremendous opportunities out there. Healthcare was at the centre of the world's attention for the last 18 to 20 months, and our emergence from the pandemic is because of innovation in healthcare, biotech, life sciences. There's so much work to do beyond working as a clinician — in existing companies hiring clinicians or people who can work in the digital realm with a clinical perspective, and in the huge number of companies that still need to be founded and problems that still need to be solved.

It may take a while. The best fallback you can have is your hard skills. The reason a doctor has job security is that you have skills and credentials — you can be dropped in a hospital and be useful. If you can say the same about your digital skills, you should have the same job security, if not more, because you can work from anywhere, for companies not just in the UK but anywhere in the world, across sectors. And by digital skills I mean anything from copywriting to design to software development. If you can learn some of those things — which is hard — you'll be in an even stronger position. So there's a huge amount of opportunity. I'd advise people to learn useful skills the world of work needs — look at what people are hiring for, research which skills are on the rise — and learn some of those. It's hard, but it can be done, and you'll have a very bright future.