Angel Investing, Money and Happiness

You're absolutely right. Let me break this down into those three buckets: capital, motivations, and networking.

On the capital side, the good news is that a few things have changed in the last few years. When I was first raising for my startup in 2018, the dogma was that having a big, fragmented cap table — lots of different investors — was disadvantageous for a variety of reasons. First of all, you need to get them all to sign paperwork, say if you need to issue new shares or you need investor consents. Having a long tail of people with a very small amount of skin in the game was considered a bit messy, a bit of a disadvantage in executing legal documents, and possibly a sign that you couldn't raise from an established fund. Now the pendulum has swung the other way. You have startups raising party rounds, and startups that have set themselves up specifically to solve this problem — enabling lots of angel or individual investors to come into a round on one line on the cap table, using special purpose vehicles.

That has also meant the minimum amount an individual needs to invest to get into that SPV is a lot smaller. So now the smallest ticket you'll see is about a thousand pounds or a thousand dollars — I've even seen people invest $500. You could argue, what's the point of putting $500 into a startup? But we can talk about that in a second. Capital requirements have generally come down, and the environment has become more permissive for small tickets, particularly through vehicles like SPVs. Companies that do that are AngelList, there's Vauban — which was recently acquired — there's Odin, and I've used most of these products myself.

In terms of my motivations — you touched on it, but principally they're not financial. By that I mean I'm not creating my retirement plan on some assumption that my angel investments will pay off. For me personally, I feel a great sense of purpose when I make angel investments, because when you work with early-stage entrepreneurs it's a bit like setting off on an adventure with someone. There's a lot of risk involved. Picture the scene: you're setting across on a journey over choppy seas, with some dream of upside on the other side of the ocean. You're backing these people who are trying to do slightly crazy things with very aspirational, maybe slightly unrealistic views of what they can achieve — but they're very talented, very determined. It's exciting to be part of that. It gives you a sense of mission.

And oftentimes, especially with the companies I've been working with, they're solving real and meaningful problems. Some are looking at neglected medical conditions where traditional treatments in even developed healthcare systems aren't very good — like tinnitus. Others are doing things to combat climate change, or reduce inequality in the workplace. Code First Girls, for example, is training women to be software developers and engineers, with very high representation from diverse backgrounds. That sense of mission, backing causes, is a tremendous part of the motivation.

Then, to your third point about networking — that's absolutely true. As an entrepreneur — well, an ex-entrepreneur; I'm working on my second business at the moment, not a traditional tech startup but an advisory and media company — you face a lot of challenges. You don't have the same security or brand recognition that people at big companies do. But entrepreneurs know in their heart why they're doing it. They feel alive when they do their work. They feel a sense of purpose, a sense of ownership; they can express their identity, their own personal values, through their work.

So by angel investing, you create bonds and ties between yourself and other people who are aligned with your way of thinking about the world, who are on their own mission. These people are generally very talented, very high-agency — not passive people in worker mode, but solution-oriented people trying to solve big problems. By building these alliances through investing and backing and supporting them, it creates a sense of community and network, both with the founders and with the people you co-invest with. Each investment you diligence is a bit like a piece of work, and when one closes it's a great feeling. And with the founders — some of the ones I've backed, I know their businesses are facing challenges, as many early-stage startups do, but that's kind of beside the point. I still want to support them through those challenges, even if they leave and go on to found something else, because the relationship isn't specific to the company they're founding in that instance. That might sound counterintuitive if you think about it purely as a financial investment. But for me, that networking piece — understanding those problems, being part of this engine that's creating jobs for the economy — is tremendously important.

Great question. The first thing to ask yourself, especially now that we're in an age of relative abundance when it comes to capital availability, is: why should a founder take my money? That's kind of a crazy question. Even a few years ago — in 2018, only four years ago — the thought that founders would be very picky about who they take money from wasn't really the case. A lot of founders would take money just because of the availability, or the perceived availability, of capital; my perception is that in the private markets it was tighter, less available. I don't know exactly what the drivers are, but we've been in a secular bull market for a number of years. A lot of people, especially those who were liquid and invested during the COVID crisis, saw tremendous gains. Many of those gains have now reversed, but there are people who increased their net worth and probably have more capital to deploy now. And all these startups have made it easier to invest in the private market. So generally there's a lot of capital available — which makes the question critical: why should somebody take my money?

There are lots of reasons. A simple list: first, you can introduce them to other investors or to customers, or you have an audience and can amplify their brand and their perception among potential hires. Big Picture Medicine would be a great example of that, especially for startups in healthcare — your audience are people who may be very relevant for these companies to get their voice and story out to.

Another reason: people like to have founders on the cap table. If you've been through the journey — you understand how long it takes to build a company, that it's not a linear path, that there's a high rate of failure — you're just easier to take on the journey, especially through the twists and turns. And some founders are very high-profile. Founders of household-brand startups with wide-reaching recognition — having them on your cap table sends a signal, and signalling is an important part of fundraising.

The final thing is that in some cases people have very specific skills or knowledge. I recently invested in a company where one of the execs of the biggest public company in that same space also invested. In fact there are two like that. One — which I'm hopefully in the process of investing in — has one of the co-founders of Slack investing; it's building for the future of work. The other is a life-sciences technology company where one of the execs, or ex-execs, from Veeva — a company that makes technology for pharmaceutical companies and research — is investing. Those types of angels send a signal, because if a founder can recruit them onto the cap table, it tells other investors that somebody who knows a ton about this industry has put their money where their mouth is. So you should pay attention.

Absolutely. The internet rewards people who are interesting, or funny, or can express their ideas well. I've found myself in a situation before thinking, what can I create content about? What can I talk about on the internet? Because I recognise that having an audience and creating content is an important part of how you present yourself in the modern world. People will Google you before a job interview, before a podcast, before a call — it's bound to happen. And no matter what you want to do, especially as an entrepreneur, having an audience will make your life easier. Even for academics these days, having an audience makes your academic clout a lot stronger.

So if you're struggling for what to create content on, or how to be of benefit to people, this mantra is really powerful. If you want to be someone of interest — someone whose tweets, video content, newsletters, whatever it may be, other people want to follow — then just do interesting things. It's also a good recipe for life in terms of skills development, network development, building experiences: just do interesting things. I'll leave it to listeners to decide what an interesting thing is — it might be learning something, taking on a challenge, reaching out to someone, taking a risk, documenting the process. All of those count.

That's the context in which I think about this quote — especially if you're struggling for direction, not quite sure what to do at this phase of your professional journey. One thing I say to people is: don't sit in a room and try to cogitate your way through the problem. Go and do something. Find a problem and apply yourself to it. And if you want to be interesting on the internet, document the process.

Good question. I actually published — in one of my videos, I think it was on wealth creation, and I'm not trying to plug it here — a little animation about how my annual salary has changed as a multiple of my salary in my first year out of medical school. And honestly, it has fluctuated by a factor of 10x year to year. That's not an exaggeration. And when I say fluctuated, I don't mean it's gone up — sometimes it's gone down and other times up. For a lot of people that's difficult to contemplate, because they think the inevitable progress they need to sustain in their career is partly measured by their salary always trending upwards. The truth is that if you want to do something that can take you to the next level of skills, credibility and income, you often have to take a step down. You have to take a risk. Your income will drop in the near term for it to go up in the long term. Think of someone who quits their job to start a company. That company might fail — but in the first instance they'll more than likely take a pay hit, and they may make a lot more money in the future. It's not guaranteed, but they'll have that initial dip before things come back up.

So, specifically: does money buy happiness? In my case, money buys freedom, and it buys the ability to do stuff I believe in — which maybe is also freedom. When I say freedom, I mean that for us as a household — me and my wife — if we didn't both want to work full-time, then your earning power creates that cushion to reduce your hours. Some people will never reduce their hours; their mentality is, I'm going to keep increasing my earning potential and keep working full-time. Our view is that there's a certain amount of income we'd like to make to sustain a certain lifestyle, to save, to invest — when you have children you have to worry about these things — but we'll buy some of our time back, either by outsourcing certain things or just not working some of the time, particularly as we homeschool our children.

Money buys freedom in our case. Freedom from, and freedom to. Freedom from anxiety, from having to be somewhere at a specific time doing a specific activity you're bound to do. And the freedom to do things like travel, or angel invest. Those things can really contribute to a sense of contentment. For me, the ultimate form of happiness is having the freedom to work on things I really care about — and that, for me, is enabled by money. It's not that I don't want to work; my idea of freedom isn't to sit on a beach — I don't think I could survive more than a day of that. But if I could choose to do work I'm interested in, on terms I'm happy with, for the amount of time per week that makes sense, from places in the world that are interesting for me to work from — then that's good. And money is a big part of that.

That's a really incisive question, because I'm actually a traditionalist when it comes to a lot of these things. These periods of travel do create tremendous opportunity to experience new things, which is exhilarating, but they also create certain challenges — being away from family, away from social ties, losing a sense of routine, at least in the transition periods between moving from one time zone or geography to another. There's a lot to be said — you feel it especially when you have young children — for the fact that a lot of human beings are creatures of habit. Familiarity and habit are certainly important for my wellbeing.

So in most cases when we travel, there's a specific reason for where we're going. In this instance, the reason we've come to Malaysia is that our children are learning Mandarin, and bringing them here is an opportunity to pop them into local schools so they can be exposed first-hand to a Mandarin environment. There are sacrifices and challenges we face to make that happen — it is stressful. I'm not just talking about money; there are stresses when you unplug yourself from the support network you have back home.

In my mind, the ideal scenario is a balance between the two. I love routine — down to the level that every day back home I'll have the same breakfast, from the same supermarket, the same products. I love that routine, not having to worry about it, freeing up that headspace for the things I really want to be challenged by. Being able to mix it up with these periods of travel — that balance, for now, feels quite fun. I think when my kids get older and need more stability — a bit like I had stability between the ages of six and eighteen — they'll need that at some point. So I actually agree with your point. There's a lot to be said for routine, familiarity, community. There's a reason those things have evolved in human behavioural patterns over a long period, and when you go against the grain it does cause negative consequences.

I agree with you — it was typically for people who had an exclusionist perspective on mainstream society. They were trying to get away from something. In some cases that was particularly conservative religious groups, or people who were effectively hippies, or fringe groups. But COVID resulted in a kind of forced homeschooling experiment for many parts of the world, at least in the UK.

The way we homeschool is that we don't actually do most of the education ourselves. We do something called micro-schooling, where our kids join small groups of five to ten children being taught by a trained teacher in an out-of-school setting. It's a smaller group, maybe slightly mixed stages, less contact time, but a much smaller number of children per teacher. As a consequence, our kids have a lot more free time. And we can augment the schedule with topics or activities we feel are important in early childhood that traditional school would struggle to provide unless you were paying large sums of money. Because we want a big family, forking out thousands of pounds a month on education at this age feels like a trade-off we're not quite willing to make right now.

There's also a separate question: when you say our homeschool kids are weird, or are they just outliers in some regard — what's your norm? If your norm is playground socialisation, that bucket of experiences kids get in a traditional school playground, then yes, homeschool children have a slightly outlier experience; they have very different social patterns. For me, that's not my benchmark. The way I think about it is: are they well-adjusted and happy? Are they interested in what they're learning? Are they getting plenty of physical activity? Are they spending time with parents and teachers and people we feel really thrilled for them to spend time with? Are we nurturing their creativity? Those questions tune into a slightly different benchmark that we're creating for our own children around what feels normal for us.

I think schooling is a tremendous service — I have huge respect for schoolteachers. There are many in my immediate family, including both my wife's parents. So it's not a critique of school per se; it's more that, especially in early childhood, this works quite well for us right now and it feels like we can provide well for the children. It also gives us the freedom and flexibility to travel.

There's a separate thing I haven't gone into — the stuff we deliberately lean into with homeschooling. If the world is changing as fast as it is — even through the COVID pandemic, so many things about how I make my money, what my work looks like, where in the world I work from have totally transformed — then the skills you'll need to thrive in the future, as the world of work changes, I'm not sure the schools we'd have access to right now could keep up with that pace of change. I think we've got a better shot at doing some of that ourselves. So as our children get older, we'll spend more time on certain types of skills development, resilience, life experiences — even simple things. Most schools don't do a great job of teaching children how to prepare their own food, or actual skills they can use to earn money above minimum wage when they leave school. There's a lot in those buckets that matters to us that we'd like to teach our kids.

Interesting. Just to get the chronology right: when I joined McKinsey, five months after I joined I had my first child, and then I resigned two months after I had my second child — my first was two and a half at the time. And I had my third child at the startup, about a year before I left the company.

So there are definitely trade-offs in working a busy professional life and having a young family. I don't think you can have it all if you're climbing the greasy pole, working 70 hours a week in a job that demands you be in certain places at certain times and doesn't afford flexibility. You'll make certain sacrifices — you'll see your children less, your spouse less, you'll exercise less. Something will give.

The way I've thought about it — and a lot of this I'm figuring out as I go, I don't have it all figured out — is this. In a traditional career story, the first third, from about 21 or 22 until 35, is when many people are most busy; for some, that's also when they settle down and have young children. Then from 35 to 45 or 50, maybe their kids go through their teens and pop out to university, and the empty-nest years start from 50-plus. So for many people, the early phases are when they're most busy, and then when they have more flexibility — when they're coasting, or have financial security — their kids have actually left the household.

My wife and I really want to spend a lot of quality time with our children while they're young. We want to travel with them, to be there day to day — I want to eat with them every day, three meals if I can, otherwise at least breakfast and dinner. So I've conceived of my career by turning those phases a bit on their head. I had a busy part at the beginning, but in this middle period I've got a unique opportunity to spend time with my family — and to take care of other things, like health. If you lose track of your health in your twenties, thirties or early forties, it'll bite you in the ass in your fifties. So I want to take care of all of that now.

And I wonder if I can have almost an encore in my career when I hit 45, when my eldest will be about 16 and my youngest eight or nine — when I might rededicate myself to a traditional organisational leadership role in a large company. So I've flipped it: I'm taking that latter period, where I'd have much more autonomy and control, and bringing it earlier. How do I make that work? There are certain things I need to do. I need to own equity so I have a shot at financial freedom, so in this period I'm not missing out on the financial security I'd otherwise have had in my fifties. Second, I need to think about how to maximise my earning potential now — which for me means developing certain hard skills and experiences, then contracting on my own terms with flexibility. There's no point being a contractor if I then have to contract in Paris four days a week, because then I've lost the autonomy.

On skills development — even this content creation. I believe executives of the future, in companies with a hybrid or remote element, will need to be good at content creation. They'll need to understand storytelling — written, video, all of it. Take someone like Vas Narasimhan, the CEO of Novartis. He pops up on my LinkedIn feed all the time with his corporate messages, his internal messages. If I were an employee of his company, I'd feel I had an ongoing conversation with my CEO — I know what's in his mind, what he's like to talk to, what his personality is like, because it comes through on camera. So one experiment that will emerge over the course of my career is: does this audience-building, content creation pay off? If I go back into a traditional corporate role in 10 or 15 years — especially because I'm also trying to contract to keep my hand in with day-to-day work — will I be penalised for having had this period, or will I be able to leverage the skills, the platform, all of these things as a unique advantage?

A hundred percent. The CV of the future isn't going to be a document someone prints out and staples. It's going to be all the stuff people find on the internet — for better or worse, because the internet has a long memory. It'll be everything they find when they Google you: your personal website, all your media assets, the things you've built that are testament to your ability.

Just on your point about motivation — I do enjoy content creation. A lot of people with that entrepreneurial impulse like putting stuff out in the world. The classic startup mantra: ship something, ship it. When you release this podcast, you are shipping a digital product. You can monetise it in different ways, as we talked about earlier, but it's basically a digital product — a direct-to-consumer business in a sense, because you have these consumers and you're searching for product-market fit. That's a sign that your repeat listeners as a ratio of all your listeners is high, and that when somebody listens, they stay till the end. Those are your consumer product metrics. A hundred percent agree with you.

I certainly have that creative impulse and I enjoy it. I have to get a bit more serious about it now, because I've made quite a lot of videos in a random-walk fashion — leaving-medicine videos, management consulting, six or seven different topics. So I'm now trying to be more disciplined. But there's also a skills-development element. The workflow you have to put in to get this podcast to happen at the right time with someone potentially a lot busier than you — that's a skill. Systems thinking, communication, process management, editing something to perfection. Those are professional skills you're learning. I feel the same when I produce content — scripting, shooting, audio, video, editing. That's a skill set. And even in the future, if I'm not doing it myself but I'm in a business producing content as part of a marketing strategy, I'll probably have more experience than most people in the room, unless they're professionals in this space.

Ah, you have to pick a side. I think you'd be solving for slightly different things. If you're an exceptional engineer, you'll be paid extremely handsomely and you'll have your pick of any career, or you could start your own company — though that will still probably be stressful, because it's not just about being good at coding. But you'll have a great menu of professional options and financial security. If you're an exceptional content developer, you'll have to deal with everything that comes with fame and recognition, which is a very mixed bag. You may become financially wealthy, but not necessarily. And you may be tied to your work, because a lot of content creators can't exit and sell their brand — their brand is them, so it's difficult to sell.

So, pros and cons. If I had to choose right now — I actually enjoy content creation. I'd probably enjoy software development too if I were a maestro of it. But because I have to choose, I'll pick content.

I believe you should always be 100% honest with yourself and the people around you about your actual competency and understanding of a situation. Even if you're asked to lead something and you don't know what you're doing, being honest and open about that doesn't have to make you seem like a weak leader. Say I was in a company right now facing a challenging situation I didn't fully understand — my instinct would be to be very open about that, but to share with my team how we're going to solve it: which expertise do we need to bring in, what decision framework or values will guide us as we navigate a period of uncertainty or immense challenge. That's how I'd approach it, because I think it engenders trust and confidence.

There's a certain type of authority figure that is masking a lack of confidence — the fake-it-till-you-make-it thing. If you take it to its extreme, where you are actually faking it, that's very dangerous. Healthcare is a special example where it's very dangerous, but even in business. So my instinct is to adopt the amateur mindset. The interesting thing about the etymology of the word "amateur" is that it comes from the root meaning someone who loves to do something — if I've got that wrong, just cut it out. Demonstrating that you're learning, developing and constantly improving — for me, that feels like the right thing to do.

A few things. I certainly think spending most of my twenties off social media really helped me. I was at medical school when Facebook was released, so before that there was no Facebook, and it wasn't a huge part of my life in the early years. There was no WhatsApp. I never really used Instagram until I created an account to share my video content — same with TikTok. I still don't have a Facebook account. And I see now, as a content creator, when I have to dip into those platforms, how much of my time they can consume. So the ideal balance for me would be to be a creator on those platforms without falling into the consumption trap. I do think it's a trap, because a lot of these technologies are — "weaponised" is a strong word, but in terms of people's attention, it's kind of weaponised. So the first thing is: take control of your time, your focus, your attention, and deploy your energy on things that really matter, whatever stage of life you're in.

The second thing is habit formation. A big part of that is surrounding yourself with people trying to build the same kinds of habits — regular exercise, eating well — but also defaulting some of the decisions in your life towards the healthier, more focused option. As an example, how you set up your house and working space. For me, am I setting it up primarily as a place where I can work really well and work out? Or as a place where I can play video games and watch films — even though that's something I don't do that often. Doing the former means it becomes a lot easier to avoid distraction, to work exercise into my routine, to cycle as part of my commute.

The final thing — this is a bit of a random list, but to add one more: whenever I'm facing something challenging, a big task or big goal, my instinct is to just run head-first at the problem. That can get you into all kinds of difficult situations from time to time, but the benefit I've sometimes seen is that I'm able to break the back of a problem. In the world of content, people say: just ship the product, even if you're not happy with the video or the podcast, just get it out the door. So thinking about something challenging and asking, what can I do to break the back of this thing, or really commit to just getting it done — whether that's having someone hold you accountable, or scheduling time in your calendar to break the problem down and move it forward, so it doesn't feel like a big unstructured thing you can't make sense of. That's something I think I do subconsciously, but it's been mentioned to me several times. So that's probably one worth mentioning.

Thank you.