About this episode
Will Gibbs leads the Future of Health team at Octopus Ventures, one of the largest venture capital firms in Europe, with over a billion pounds under management. Will studied classical archaeology and ancient history at Oxford before trying his hand at pig farming and then eventually becoming an investor at Octopus.
We talk about the pros and cons of being a doctorpreneur, being right when others are wrong, and how to become a super connector. I hope you enjoy.
In this conversation
- Classical archaeologist, then pig farmer, then organic-spirits founder, then almost-doctor, then VC: how Will hassled Octopus for weeks until someone took a coffee with him, and turned that internship into leading its Future of Health team.
- The super-connector thesis: the best investors aren't the ones with capital, they're the ones who make themselves useful — and generosity, offered when nobody expects it, is how you work your way to the middle of a network.
- Why clinical founders both win and lose: deep domain expertise earns respect and an unfair advantage, but the same founders often build what a VC sees as a feature, not a billion-dollar business.
- "Being right when others are wrong" doesn't apply the way you'd think at the frontier — in cell and gene therapy manufacturing or digital pathology, there's often no market to invest counter to.
- How a VC judges themselves when feedback loops run a decade: markups and fundraising are vanity metrics, pattern recognition is "a giant bundle of cognitive biases", and it almost always comes down to talent and sales.
Transcript AI-generated
So Will, could you tell me a little bit about your story — how you got to where you are today?
Sure. I'd probably say it's not a very linear or straightforward path. Coming out of school — this is going back a little way — I didn't really know what I wanted to do. I quite liked making things and I quite liked learning about stuff, and that took me in a number of different directions. I was pretty confident aged 16 that my life would be farming pigs. And that did end up happening, albeit I'm very keen later in life to go back to farming.
Then my parents tried to convince me that I should go to university, at which point I wasn't actually sure that's what I needed to do. But I went, and had an amazing time — albeit I spent most of my time trying to get out of uni and sailing, or doing sport, or doing something. Then I came out and decided I didn't really want to go into consulting or banking like most of my friends and peers. So I decided to set up an organic spirits business, and most of my weekends looked more like an Apprentice challenge of flogging alcohol at food and drink shows around the country. That was good fun, albeit I realised it's a very hard and quite a lonely way to build a business.
So then I decided that actually I might be better suited as a doctor. I convinced myself that that was my passion, and the dream was to combine medicine with something more adventurous — the dream job would have been to be an expedition doctor for a group going to the North Pole or climbing mountains. That would be the holy grail. So I spent a year working as a volunteer with first responders, doing work experience in hospitals. I was also a volunteer with the Samaritans, helping people with suicidal thoughts. And doing that made me think, actually, medicine is fantastically exciting. There's the learning bit — there isn't necessarily the building bit, but I was still excited enough.
So I did all of my science A levels at home from a textbook after coming out of university. I ended up going back to my old school and being with 16-year-olds doing AS-level chemistry, biology and physics. I had a place to go to med school, but decided, very much at the last minute, that I didn't want to do another five years of exams — I'd maybe be learning, but in too much of a structured environment for me. That's when I decided I wanted to go back down the building route.
I wasn't quite sure what venture capital meant at the time, but what I'd read made me think it was building businesses with other people's money instead of mine. It kind of looked like a paid MBA, and I thought, actually, that looks quite exciting. So I spammed a load of people in the industry, most of whom very sensibly said no — other than Octopus, where I hassled them for a couple of weeks until someone gave in and decided they'd take a coffee with me. I'm pretty sure the directive on that came from the top: just, someone meet this guy and make him go away. And I convinced them into giving me an internship. I started as an intern about eight years ago, didn't really know anything about finance, but I think they could see that I like making things, I like chatting to people, I was quite curious, and I had an interest in commercial things. So that's kind of where it started, and it's been a very aggressive but exciting learning curve since then.
You mentioned the paid MBA. I recently came across a book by Josh Kaufman, The Personal MBA, and the concept is that you can get the level of an MBA education just from reading this book. How much of the MBA side do you think you can just pick up working — and do you think it would have been good to get the formal education as well?
“It's really about trying to make yourself a super connector and make yourself useful to people, even if it's not about capital.”
Will
Taking a step back — in venture capital, if I look at the most successful people in the field, they're those with very strong relationship skills. It's really about trying to make yourself a super connector and make yourself useful to people, even if it's not about capital. There's probably an element of knowledge and expertise, but the network bit — just being excited about people and wanting to solve puzzles — is quite a different part of your brain.
Within our team we find some amazing people who've come from an MBA background, but I'd say those folks are normally ones who have very strong technical credentials and want a rapid way of getting up to speed on the commercial side. So for me, the jury is still out on MBAs.
Another side of the whole university and formal teaching debate is that amongst medics and doctorpreneurs, the thought process is that if you have clinical experience — if you're seeing patients regularly — that's a very strong competitive advantage. In terms of the companies you see or invest in, is it a massive competitive advantage? Or do you see a lot of successful people who don't have that clinical experience?
I like doctorpreneurs — or whatever terminology you use. I think it's a category of entrepreneurs that, as you'd expect, has massive range. Maybe I'm oversimplifying, but I see it in quite a polarising way: a lot of amazing clinicians understand their processes and field better than anyone and are massively passionate about patients, in a way that's really humbling. I find that exciting.
But if I look at how we often debrief on teams where there's a strong clinical component, one risk that creeps in is around ambition — how big a business do they really want to build? A lot of entrepreneurs with clinical backgrounds understand the detail so clearly that what they build, or at least talk about building, is something we'd see more as a feature. It might be, okay, I've found a way of getting rid of this really painful part of the paper trail and it's relevant to every patient, therefore we can build a massive business. That's quite different to what we'd see as more pioneering — okay, I think the way cell and gene therapy is manufactured is unscalable, therefore that's the bottleneck we want to solve.
Maybe that highlights some cognitive biases we have as a team, that we might be seeing some of the unglamorous or more practical sides of medicine as not being ideally suited to venture-style businesses. And I'm sure, time and again, we'll be shown to have got that wrong. But that's a hesitation we often have with clinical teams.
The converse is equally true. I work with a team called Quit Genius, who are looking to solve addiction through cognitive behavioural therapy. Their first product focuses on smoking addiction; we've just gone live with an alcohol addiction product, and later in the year we'll go live with opioid. One of the absolute highlights of my job — this is a dream job for me — is working with the best entrepreneurs in Europe, slash the world, going after really big, nasty puzzles. The three founders there are clinicians by background, and that affords them massive respect and credibility in the field. But it's a very specific type of clinician: one who has the background and understands the detail, but isn't blinded by it, doesn't go down the rabbit holes, and can still take a step back and think, okay, I can take that knowledge — it's an unfair advantage — but I can still build a billion-dollar tech business, and I understand my personal and team gaps and can fill those. The entrepreneurs who understand that limitation are the ones I'm probably most excited by.
So with medics and doctorpreneurs, oftentimes because they're working in the weeds, they don't have a vision big enough for venture-scale returns?
I think that is a risk. And it's a conversation not just limited to health or medicine — what is the right balance of domain expertise versus fresh insights and ambition? If I think of some of the most successful businesses we've invested in, sometimes those entrepreneurs don't have backgrounds in that space, and that can be a massive advantage because they're not biased or limited by the way things have been done historically. But if it isn't their background, then you need to be comfortable on where they're going to get that domain expertise — from broader team members, non-exec directors or advisors. I don't think there's a blueprint, but domain expertise is typically something we see overlooked until a lot further down the line.
I love the Brad Feld book on startup boards. It's really interesting on how often boards are seen as an admin burden that startups don't want to build out very early. But if you invest the same amount of time into building out your board and deciding who you have around the table as you do in hiring senior VP or C-level folks — and you have a board such that your decision-making processes are better than any of your competitors — that's clearly a strong advantage and a strong foundation. It pains me that normally we're the driving pressure in companies appointing a chairperson, building out NEDs and bringing in domain or functional experts around the board table, because I think it's a real power move that can fill the gaps in a management team's experience or skill set. We're always seen as the bad guys, like it's a pain we're inflicting on people — but normally, a couple of months down the line, it's met with, actually, I wish we'd done this earlier.
One of the cardinal rules of investment and arbitrage is that you need to be right when other people are wrong. So if you decided six months into the pandemic that you wanted to make telemedicine a focus, there might not be a lot of opportunity to make money there. Can you talk about pursuing that — having your thesis, and the decision-making around it? Because it sounds like quite a challenging thing to do.
“Entrepreneurs often use a company's ability to raise money as a proxy for how good the business is, when realistically an unrealised return doesn't really mean much.”
Will
The type of stuff we're investing in — we won't know if we're right or wrong for a long time. Entrepreneurs get very excited, and often use a company's ability to raise money as a proxy for how good the business is, when realistically an unrealised return doesn't really mean much. Our whole business model as a venture investor is predicated on investing in companies that then grow to incredible scale and exit. So it's very hard to know if you're any good at this job until you've been through a few of those cycles all the way through to exit.
On investing counter to the market, there is a case there. But within a lot of what we're investing in within health, it's so nascent — these technologies really are at the frontier — that there often isn't a market to invest counter to. If I look at cell and gene therapy manufacturing, where we invested in Ori Biotech — is that counter to the market? Not sure, because there isn't really a market for how to do it. And something like Ibex, which operates in digital pathology — there isn't much to compare it to other than human analysis of pathology slides. That is counter to market thinking, and it's exactly the type of thing we get excited by.
Knowing you like your books, one person I typically refer to here is Clayton Christensen's The Innovator's Dilemma. It's a massively simplistic view, but finding opportunities where it isn't just the floppy disk one notch up along the same line, but where you're stepping off and potentially starting a new line with a new set of market parameters — that's really exciting. That for me is the holy grail.
But there's a risk that we, as investors, think we're smarter than we are. This is why we try to have theses and work out what we're really excited about. At the end of the day, if you're backing the best teams and the most likely executors in a given market, you're delegating that task to them. However smart we think the pitch and the product and the positioning are, chances are the following year everything has changed. So the best decisions we can make are: have we invested in the best team in this market? If we've backed the most agile and least egocentric team — humble enough not to be a prisoner to sunk-cost bias, who'll chase wherever the ultimate opportunity is — then often that's the best we can do at seed or really early stage.
When a company is pitching to you and it looks very impressive, and you get very into the vision — do you ever have in the back of your mind, oh God, is this another Theranos?
Yes, yes, we do. That was a really interesting exposé that made us really think. The main takeaway for me with the Theranos scandal was the number of very high-profile investors sitting around the table. It made me sit back and take stock on portfolio companies — how much do I really understand about what they're doing? And seeing behind logos and brand. It was a good slap for the industry to really scrutinise that, and hopefully to drive boards and investors to get beneath the skin of businesses.
I think about that more in terms of personal relationships — understanding not just the CEO, but building deeper relationships across the business so you understand more about what's going on. I can understand a CEO's desire to manage the board and manage stakeholders, but there's a tension there for investors who want to get involved in the real nitty-gritty. I understand why a CEO is also slightly protective, but I think that's a healthy tension.
You mentioned that the founding team is very important. Are there specific qualities or traits you like to see in people who pitch to you?
“The founders I'm most excited by typically execute at pace. They have almost unfair advantages when it comes to recruiting and selling the vision.”
Will
I'm increasingly aware of my biases on this, but there are types of founders I gravitate towards, having invested in a fair few businesses — and I've also honed in on a set of behaviours I'm perhaps more and more allergic to.
The founders I'm most excited by typically execute at pace. They have almost unfair advantages when it comes to recruiting and selling the vision. I love it when portfolio companies tell me the profile of people they've got in hiring processes and you think, how have you done that? They shouldn't really be engaging with you, shouldn't really be saying yes to this job offer — but they are, because the founder is able to convey the excitement and boldness of the vision. So, hiring capability, and just not having any nervousness about finding who the best person is in the market globally and going after them.
The other thing that really excites me is being open and vulnerable on unknowns. I have a big thing about feedback — if you talk to any of the CEOs I work with or my team members, they should corroborate that. It's the ultimate way of developing people and progressing conversations. I'm a massive supporter of radical candor — that's set reading for anyone who joins our team. People who can take that feedback openly are really impressive, and it's the ultimate foundation for building solid relationships.
The things that agitate me are largely the converse — especially when I feel I'm being sold to. It's really hard to build a relationship if you don't fully believe there's openness or trust.
You've mentioned feedback loops a few times. The traditional thinking is that to get good at any skill, you want feedback loops as tight as possible — if you're learning golf, you don't just randomly hit balls, you film yourself and get a coach giving feedback at every step. But in VC, and especially healthcare, those feedback loops can be extremely long — maybe a decade or more. So day to day, how do you know the investment decisions you're making are the right ones?
The true answer is you don't. Pattern recognition can be a great thing — or at least we can easily talk ourselves into thinking it's a great thing. But pattern recognition is also potentially a giant bundle of cognitive biases, and it's hard to discern between the two. I recently got really excited about the book Superforecasting, until I got to the final chapter, which was basically: by the way, all of this applies to everything in the world other than venture capital, which is entirely predicated on outliers and outsized returns. So there's a real tension between businesses that genuinely tear up the rule book and businesses confined to certain basic parameters.
Across the portfolio, it doesn't really matter which market these businesses operate in — it's the same challenges. The most common are around talent: have I got a senior team that will execute against the plan, and am I attracting and retaining world-class talent? And sales: how much value is my product bringing, who feels that pain the most, am I positioning such that what I'm selling is essential, and how do I scale those channels to revenues in the hundreds of millions or billions?
There's a risk within venture capital that you can make it into something that sounds really complex or smart, but for me it comes down to a couple of really basic things. Post-investment, the sales piece and the talent piece are the challenges that come up time and time again — and that's where we've tried to build out help for our portfolio companies. So are we being very prescriptive about what we're looking for? We're quite open-minded about where the next billion-dollar opportunity in health might come from. But we know post-investment, people and sales will most likely be the top two challenges. Finding teams that understand those risks and have experience overcoming them in smart, sophisticated ways is ultimately the best hedge. So we're open-minded on thesis and product, but the bar will always be high on commercialising, go-to-market, and people.
You mentioned it's quite important in VC to be a super connector — that's to do with deal flow, getting people friendly with you, getting opportunities to invest. Do you have any specific tactics or approaches towards doing that?
I do. For me, one of the most important and powerful principles is generosity. I love the writing around givers and takers and who ultimately wins. If you can be generous when people aren't expecting you to be, you can work yourself into the middle of a network and become a super connector. It drives my team mad, me banging on about this. We spend most of our time saying no to amazing entrepreneurs, and it is sad, but that's just part of the beast. So we've tried to build in institutionalised processes to make sure we continue to be generous — not just saying no, but giving very unfiltered feedback, feedback entrepreneurs maybe don't want to hear, and offering to connect people to angels and going above and beyond.
There are so many instances when folks come back. I love conversations with entrepreneurs or investors where they're not quite sure where it'll lead, but someone's said, "You should have a chat with Will — not sure where it'll go, but he'll probably figure out some way to be helpful." Generosity can be a real power play, and for me it's probably one of the most satisfying parts of the job.
Have there been any other habits or ways you've approached things throughout your career that have helped you?
Just being curious. I love reading and immersing myself in particular topics. My university degree was in ancient history — completely useless for anything I do today — but the one transferable element is going from knowing nothing about a subject to knowing 60% on it, being able to talk to the world leaders or the smartest person on that topic, while also acknowledging there's a good chunk of stuff you just don't know. Getting comfortable with not knowing anything, but getting up the curve really aggressively and honing in on the right questions — I don't think you can be good in venture if you're closed-minded.
If you're a lifelong nerd slash geek who can happily have conversations with people, find something interesting in it, find that thread and keep pulling until you get to a place where you're like, oh, actually there's a big opportunity here. When I first started, my boss Luke, who I work very closely with, explained that VC is more of a lifestyle than a job. A lot of that has to do with the intellectual curiosity piece — you're reading the newspaper at the weekend, and you'll read something and send it to one of your CEOs or founders: maybe we should rethink how we think about payers in the US, seeing this happen, or reading something about the direction of travel for tobacco manufacturers when it comes to substance addiction. It's just building that knowledge graph and network and never really stopping. I'm not sure whether it makes me a better investor, but it definitely means I don't get bored.
Do you have any specific book recommendations?
I love Flow. It's maybe not necessarily relevant to the world of investing, but for me it speaks to how I like to operate — I get a lot of satisfaction out of activity and learning and moving things forward, and that probably echoes how a lot of the founders I work with think.
I also love Blink. As a team, we often like thinking that if we add more rigorous process and diligence, it makes us better decision-makers — whereas I think there's a lot to suggest it doesn't. Being cognizant of which decision-making processes will be refined through debriefing and checklists is great, but also understanding which decisions you just won't ever be able to refine, and how there will always be an element of risk — you just need to be fine with that.
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