Being a First Time CEO at a Startup in a Highly Regulated Industry

A conversation with David Jarvis, CEO, Griffin

This week I’m thrilled to welcome David Jarvis, CEO of Griffin. We have similar views on leadership so it was fun to hear his thoughts. Our conversation covered why he started Griffin, being intentional with company values, creating a purposeful culture interview, and what it’s like running a startup in a highly regulated industry. 

It's great to have you today. We know each other fairly well, but can you introduce yourself for folks who don't know you?

Likewise, it is a delight to see you again, and a pleasure to be here. I am David Jarvis, I'm the CEO and co-founder of a UK-based company called Griffin, which is a Banking as a Service firm that is in the late stages of becoming an actual bank.

How did you and your co-founder Allen come to start Griffin?

So there are two separate stories. There's the story of how I came to start Griffin and there's the story of how Allen and I came to know each other. They're independent, but they end up dovetailing. Allen and I worked together at the company he co-founded, CircleCI where he was my boss. That was actually my first software engineering job. After that, I went to work for a very early Banking as a Service company that was not successful and was acqui-hired by Silicon Valley Bank. When I wanted to start Griffin a couple of years later, or I guess 18 months later, Allen was on the shortlist of people who I knew I really wanted to work with. In the intervening time, we'd also written a book on programming together, which is its own bizarre story that almost fell into our laps. So we had a chance to test out our working relationship in a couple of different environments before “getting hitched” as the saying goes.

So was it your experience at that other startup that led you to say, "Oh, I think there's an idea in here, but it just needs to maybe, the execution wasn't right or the funding or…?"

Yeah. This is very sector-specific, but that company, Standard Treasury, had been founded by a friend of mine from university and one of his very old friends. Initially, they had this idea of addressing the treasury needs of corporates and building a platform for that. They struggled to find traction with that. So they settled on an adjacent problem, which was, okay, well, how do we enable programmatic account and payment access for corporates and tech companies? This led them to build an API platform that they would go and sell to banks and essentially say to the bank, "Look, this is a distribution channel for your accounts and payments and your customers are going to want this because every company is increasingly going to want more programmatic control over their banking infrastructure."

The problem that we had was that all of the banks we talked to (this is in 2014) were completely convinced that there was no market for this and that this was going to be a small cottage industry serving Silicon valley startups. They couldn't process the idea that this would one day be a big need. 

So the founders of that business, we're like, "Okay, well, if we can't get a bank to work with us, that's going to be a problem, obviously, but we're pretty convinced that there is a market for this. Why don't we just go and become a bank ourselves?" The problem with that is that, in the US, the Bank Holding Company Act regulations mean that anyone who owns more than 10% of the company essentially gets very aggressively regulated themselves. So this act is a poison pill for most VCs who want to own 15 to 20% of the company. They had a term sheet from a very recognizable tier 1 firm. When the tier 1 firm figured out how the Bank Holding Company Act worked, they were like, "There's no way we're doing this."

“We're out.”

Yeah. So they were like, "Okay, well, is there another way that we can go about this? Maybe there's another country we could do this in." The UK came up on their radar because at that time the regulators had started to make a lot of noise about streamlining the application process and increasing competition in the UK's banking market. There were a whole bunch of really technology-focused firms that were going through the new bank application process among them Monzo, Starling, Tandem, Atom…all firms that eventually ended up one way or another getting a bank license.

But at the time, telling our US investor base that we were going to pivot the company to the UK and get a bank license was like, "Okay, hold on guys, reality check. None of you are from the UK. None of you know anything about the UK. We don't know anything about the UK, and finally, you're great at building APIs for banks, but we just don't have any confidence in your ability to build a bank yourselves." That was what led to the tragic outcome. 

So I ended up going to join Airbnb and was there for about 18 months. While I was there, all of these banks that we had been keeping an eye on in the UK started to get authorized. So in particular, when Monzo got authorized, I perked up and said, "This is super interesting." The CEO at Monzo, Tom Blomfield was the founder of GoCardless, a YC alum. I was like, "This guy's basically a nerd. If he can get a bank license, like, I'm not that different from him." My mom happens to be British, so I have a British passport. So that was what gave me the kick, I guess, to go and try Standard Treasury V2, really picking up the thesis that the original founders had, but actually moving to the UK and just doing it and hoping that the funding would follow, I guess, which fortunately it has.

What a wonderful backstory. I work with a lot of FinTech which is such a fascinating industry because it's so highly regulated. There's so much you have to wade through in that industry.

Yeah.

It's funny now because essentially, what we're building is like a modern clearing bank with other infrastructure components added to it. This gets me out of bed in the morning, mostly because I'm really passionate about empowering other people who want to build things. Building something that enables other people to realize their dreams and not have to jump through hoops and deal with gatekeepers is really, really motivating for me.

I think that's frankly, a lot of what motivates the rest of the team. There's an element for the software developer in me, that's just like, turning anything into an API is cool. (laughs) But in this particular case, it's further motivating because I know that the alternative is desperately trying to convince some snotty guy in a suit at Barclays to open an account for you and to work with you, which is a half a year plus process that's mostly emails rather than some friendly experience.

So for a while, when I was pitching investors, they would always ask the same question, which is, how did you come to this? I feel that, particularly in 2020, when Banking as a Service, as a sector got really hot, the question was being asked, like, "Are you just some guy jumping on the bandwagon here? No one could possibly be that interested in this space." And I'm like, "No, actually, I've been in this now since 2014 in one form or another, and I genuinely am passionate about it."

I love hearing origin stories. I love understanding why are you doing this, what’s your mission? About how many folks are at Griffin right now?

We're about 35.

Got it. When did you begin to turn the wheels to start the company?

The thing that got the ball rolling initially and started me down the path was Monzo entering what's called authorization with restrictions in September of 2016 I think. It then took me maybe six or seven months to poke at the space enough to decide that it was worth quitting my job for, which I did. Another five months after that to move to the UK, partly because of just the general logistics of moving, but also because I had to marry and get a visa for my then-very-serious girlfriend, now my wife.

So we didn't move over until October of 2017. Then we hoped to just raise a seed round and hit the ground running as we would in the States. It turns out the financing environment in Europe is not so risk-tolerant. So basically, we failed to raise a seed round and had largely given up. We had put in a cold application for a pre-seed with Seedcamp. They took a while to come back to us. Eventually, they came back to us and gave us a £100,000 pre-seed, and we were like, "I guess we actually have to do this now."

Almost immediately then, seed funds seemed much more serious and much more interested in us. So we started talking to them, got a term sheet, that didn't work out, we ran out of money, and then we had to sit in a very, very uncomfortable place for six to nine months not really going anywhere, just desperately trying to raise money and finally closing a round.

Just trying to stay alive, right? You were just trying to stay alive.

Yeah. Just trying to keep the dream alive. So we finally closed the seed round in the fall of 2019, and that was a proper £3,000,000 seed round, and that really let us start to actually do things. It can be frustrating sometimes because, for some people, they're like, "You've been doing this since 2017, why aren't you further along?" I'm like, "Because I didn't have any money until September of 2019…like, what do you want from me?"

Well, right. There are so many more hoops and hurdles than we might think. This is your first time being a founder. Was being a startup founder a goal when you started your career?

No, though I have always been very entrepreneurial. So I was the kid in high school who would drive upstate, buy energy drinks wholesale, and then come and resell them at his school. So it's always been there. Tech, generally, wasn't really on my radar for a while. And then what was interesting was, my first tech job I had a bunch of really interesting things come out of it, seminal professional development moments, let's say. One of them was talking to the CTO about my career aspirations. I had been hired basically to serve as a bridge between their algorithmic R&D arm - not a common department for small tech companies to have, it turns out - and their sales team. The sales team was basically like, "Hey, those are the smartest guys in the company. Let's ask them to do stuff for us." The research guys were like, "Please stop talking to us, we are trying to do our actual jobs."

“Leave us alone.”

Right. The chief scientist within the R&D arm was this very cool, very relaxed guy who had been in the bay area, had done a bunch of startups, some had worked out, so he drove a Roadster and generally did what he wanted and the CTO was like, "Well, what do you want to do? Where do you want this to go?" I was like, "I think I want what Matt has." He was like, "I don't think so." He's like, "I think you're a CEO. I think that's what you're going to be." And I was like, "Okay. Vote of confidence, I guess." (chuckles) But I think that was the first person who really felt that that was the place where I was going to end up. Then the experience at Airbnb was, if anything, the opposite. I was so unhappy that I had to do anything else. I was also so burnt out that trying to do anything else that involved answering to someone else was also going to be a disaster. So there was really no choice other than to stop working entirely or to work for myself.

What do you think led you to get so burnt out?

It was mostly politics. What I mean by that very specifically is, that Airbnb's engineering org did not exercise a command and control structure. It was entirely consensus-driven. That is ugly at 10 people. It is unfathomable at 600 engineers. In particular, the way it was consensus-driven was really that the earliest engineers had the political clout to thumbs up/thumbs down something, but they were not necessarily the best engineers. They just happened to have been there first. At the time I joined, there was a classic new blood, old blood thing where a bunch of new people were coming in from Facebook, Google, Amazon, who had seen systems scale pretty seriously and were like, "Look, this is what we need to do to professionalize this operation." A lot of the people who were the old-timers were like, "Yeah, but nah." (chuckles)

It was just like, "Oh, this is really painful." Because I can't actually make an argument on the merits. The only thing I can do is grind you down over a long period of time until you agree with me that this is what we need to do. And yeah, the absence of any true technical leadership at the company to just be like, "We are going to do X and we're going to rally behind this and we're going to go do that." was very painful.

That sounds like an organizational issue — org smells. It's like you were ground down by the decision-making process.

Yeah. So this is one of my favorite stories, because this, I think, exemplifies what I was up against. You'll appreciate this, given your background. So the main codebase is written in Ruby. I wanted us to agree on a standard writing style for Ruby because Ruby can be written many different ways and that can be a bit of a pain if you're switching teams or trying to dig into a team's codebase that has written it in a radically different style. And I was like, "Okay. So let's just agree on what the Airbnb Ruby style is and then we'll put a linter in place." Because I was on the dev infrastructure team, and that'll be that. I got so much pushback on this and it was really specifically from one guy who I'm not going to name, but who just was like, "I think the right approach is, let a thousand flowers bloom, let people write code however they want to write code. It's an artistic expression."

And I'm like, "No, readability is actually a big deal. Code is read far more often than it is written, standardization and readability are really important." To get the linter adopted, I wasn't allowed to just roll it out. In spite of the fact that I was on the development infrastructure team and this person was not, I had to put together a council of engineers to vote on this. After they did that, and they chose all the different rules and configurations for the linter and blah, blah, blah. I didn’t care what the style was, just that there was one.

We rolled it out, and I was like, "Thanks, everyone. This is done, awesome, good job." He was like, "I still hate this." And I was like, "Well, dude, at some point you're going to have to just disagree and commit and we're going to have to move forward." And he was like, "No, I don't think so. I want to be able to re-litigate this forever because I believe that you've made the wrong decision." And I'm like, "Oh my God, you're insane. You're just a crazy person. I can't have anything further to do with you."

It strikes me as a scaling issue too. In some ways, that's a great training ground for being a founder. Probably informed how you wanted to think about your startup when you became CEO as somebody prophesied earlier in your career.

The benefit of working for a bunch of different startups is you get to experience different culture soups and get a sense for some things that you think work well and things that don't work well. It's not to say that you are going to get it right yourself, but at least you're starting with a position of not needing to repeat some mistakes that you otherwise might run into.

Well, and as you know, Maria Campbell has been on the series.

Legend.

Absolute legend. She told me the values were written down before other people came on board. What made you and Allen prioritize this? Was it those past experiences?

Definitely the past experiences. There were very clear traumas that we had experienced that we wanted to make sure were not repeated. Then there were some things where we had a thesis that Griffin was structurally different than normal businesses.

So to your point earlier, building a regulated business is different from building an unregulated business. Move fast and break things is not acceptable to the regulators. So you want to make sure that you're really codifying that and that people understand on their way in the door that this is not a fail fast type environment. Or if it is, it's all about measuring and assessing risk before you run the experiment.

From the beginning almost we were very structured and not just thinking about values as aspirational, but thinking about them as things that needed to be descriptive. Therefore we needed to have a very structured interview that would tease out the things that we were looking for.

Because of course, it's one thing to have your values on the wall. And it's another thing to then have a culture interview, which is basically just like a banter session at a pub. You're not actually testing anything there. I think if you're serious about this, you have to poke at the specific things you're looking for.

I agree. Would you be up for sharing one of the questions you ask around values? I think people are really curious about this.

Yeah. So it's a documented thing within the company and it's a living document. It's reasonably stable at this point, but as we have matured, there have been things where we've been like, "It seems like we're missing on this consistently, which means this question that we've been asking is not actually doing a good enough job." There's a lot of preamble to the interview that we do with people. We clarify that this is a structured interview. This is not a banter session, we have very specific things we're looking to assess, but also, we're very comfortable with this interview being discursive and digressive, that's totally fine. We'll go down on rabbit holes, we'll probably share stuff ourselves. So we have a core value of kindness and empathy. For us, one of the things that we have come to appreciate is that overwhelmingly the thing that you want to test for on that is communication. 

I'm trying to think about how to say this so that I'm not giving away what the correct answer is…you want to make sure that you're bringing people in who don't think of conflict as the result of a hostile world, but rather think of it as arising from misunderstanding or lack of context, or any of the normal, healthy reasons that people engage in conflict that doesn't mean that anyone's a bad person, right?

So the first of these questions is, “What do you find most difficult about working with other people?” Then, “What makes you happiest and most effective when working with other people?” This is very valuable for us, just in understanding what motivates them and whether or not they're going to be happy here. And the third is, “What would your best friends say are your strengths and weaknesses?”, which is a super interesting one because you get to poke at two different things. Like you're expressly not saying, what are your strengths and weaknesses? You're like, "I want to know how you think other people perceive you."

That’s brilliant. Thank you for sharing that. I don't think a lot of times we think about how do we have a real culture fit interview that is not just beer at a bar or something, and that can lead to a lot of bias and it can also lead to missing good hires and then hiring people who aren’t a fit.

Yeah. To expand on this a little bit further, the other part of this is who's allowed to interview people for culture. In the early days, obviously, it was just Allen and me. This is a 90-minute interview and it became clear that the CEO cannot spend 90 minutes interviewing a candidate every week, which is where we are at this moment in time. So you need to figure out who else within the organization is going to be a fit for that. The obvious ones generally do tend to be early employees, but not universally. They tend to be early employees because they become so much of the culture, but in thinking about who would become a culture interviewer, we then had to develop our own rigorous framework around what we wanted in a culture interviewer.

So we decided we want someone who has a very high level of insight and particularly some prior evidence that they are a good judge of character. And that they're very clear in articulating concerns. It's not enough to say, "I didn't vibe it." You have to be very specific about — this person gave me this particular concern because of the way they phrased this thing, and I'm worried it's going to manifest in this way. They have to be very passionate about our culture, and enthusiastic, I think that's an obvious one. Equally, they need to be an exemplar -everyone else needs to agree that they are someone that people look to. They need to have been here long enough to speak credibly. They need to be very good at steering an interview because these things can get discursive. So they need to be both comfortable doing that, but also able to lead it back. They need to be a very good listener because there's so much subtext and they need to have a lot of self-awareness. And then the other thing, sorry, I've gone really deep on this…

I love it.

The other thing is we now insist that there are always two people doing this. One person leads the interview, and there's always someone shadowing and both of them have to take notes. So, if there's a point of disagreement, we have these two artifacts that we can refer to on what actually happened because with something like this, bias is the biggest risk that you're facing. So you have to build in multiple systems to try and address that.

I love that you went deep into this because culture is so important and yet there's so much fuzziness around it. You all are removing that fuzziness and you even have a value or a core behavior about thinking in systems?

“Everything is systemic” is not a value, but it is one of our culture documents. Or, actually “all problems are systemic”. If something has gone wrong once, it's gone wrong many times, you just aren't aware of the other times it's gone wrong. So you need to start digging.

It reminds me of the way that you're living that. On another note, failure seems almost woven into the fabric of startups. They encourage, as you talked about earlier, fail fast, which of course is not at your startup. What's your relationship with failure like? Do you embrace it? Do you fear it? Is it "complicated?"

I like the air quotes. (chuckles) I think it is complicated and we're at this really fascinating point in time on our journey where if I take a step back and think about how people talk about the fear of failure and risk of failure, it feels to me like you get most of the noise in this larger conversation about failure from people who are at one end of the journey.

So it's either over and they completed, they successfully did the billion-plus IPO or the exit or whatever, and they're like, "And of course, we were always worried about failure, but blah, blah, blah, look at how well it turned out for us." And then you have, I think some level of, I don't know, lip service and open panic for people who are like at the beginning of that journey. But it's very hard to take anything that they have to say very seriously because there's nothing to lose other than the time that they personally have spent thus far.

Whereas we're at this really interesting point where we have - or will soon have - raised like 20 million pounds (which is a lot of money!) over multiple fundraising rounds from very credible people, have progressed very far along the authorization process, have invested a huge amount in technology, infrastructure, and people. And yet, it's still not a guaranteed outcome that everything works out well. So to me, I think we're at the most interesting point, which is, there's the classic whatever thing, like, 9 out of 10 new businesses fail, but that's a lie because 9 out of 10 businesses fail because most of the people who try and start businesses are crazy or incompetent. Just realistically, they have absolutely no hope. They have no idea what they're doing and they give up in a month.

If you get beyond that you've raised several rounds of institutional capital, your odds of failing are nowhere near 9 in 10. But they're also definitely not zero! They're probably, I don't know…I don't know what they are for our stage, somewhere between 20 and 40%, I would guess, maybe even more than 50%. So it's not like the odds are super stacked against you, but they're sufficiently material that you definitely worry about it. I think equally, it's especially true if you haven't made it through to being profitable, which we definitely haven't. So there's always that knowledge that the onus is still on us to continue to be lucky because if we're not, and there isn't another check coming, we will not survive.

I've not heard somebody talk about that, those opposite ends. And I love that idea of, how do you think about failure? How do you consider the risks when you're a startup founder and a startup CEO?

I think it's really difficult for people to talk about failure in the moment. We could talk about Standard Treasury failing now and draw lessons from it without necessarily feeling any personal level of failure from it. Equally, I've mentioned this in a few other places, I was fired from CircleCI by Allen's co-founder who then also fired Allen, or I think he fired Allen first and then fired me and a couple of other people at the same time. At this point with a healthy amount of distance, I'm able to talk about that. But I'm not sure that my response at the time if I was forced to turn that into a narrative, would be all that coherent. Yeah. I don't know. Maybe it's because I've had a long time to stew in this in-between space.

Well, it's like the distance too. I think sometimes there's this idea of you fail and then you just get back on the horse and you move forward. I think sometimes failure, we have to have distance from it to properly maybe process it depending on how big the failure is or what the stakes were. On a different note, is this your first leadership role?

No, although it's my CEO role and my other leadership roles, it really depends on whether ... if I was looking to hire my replacement and someone showed up with my other leadership roles, as the only things on their CV, I would be like, "This is a joke, right?” These are sandbox leadership roles, but that doesn't mean that there weren't really valuable lessons in them. In some ways, sandbox leadership is a good and safer way of letting someone grow than putting them straight in the fire. 

So specifically, I had a bunch of really early leadership roles primarily when I was in university. I was the general manager for a student-run coffee shop, so initially, an assistant manager and then the general manager. I was the program director for a diabetic children's summer camp, which ran over a period of about three months during the summer and had about a hundred children and about 50 staff at any point in time. That was a super fascinating one because I had been going there. I'd gone there as a camper because I'm diabetic. Then as a counselor, then I worked in the kitchen and then had gone from the kitchen to the program director, which is not a normal transition!

Then the other one was serving on the committee of the student-run theater body, which put on about six shows a quarter at my school. So I had different experiences with being a leader with different org structures and sizes and degrees of safety rails, definitely an interesting series of opportunities in which to screw up really badly, but also have it not be the end of the world and to get exposed to some of the ways in which people go wrong, for lack of a better term.

Yeah, those are great experiences. Well, and as you mentioned, it's your first time being a CEO. How was it different than what you expected? Or I don't know, maybe you didn't have expectations going into it, what it would be like.

That's a really interesting one. I'm not sure that I know what the answer is. I think my off-the-cuff answer is that I just hadn't devoted any time to thinking about it. I'm a very mission/outcome-oriented person. In the beginning, I just did the stuff that the company needed to get done. Then as we grew, I hired people to do the stuff that the company needed to get done. And now, obviously, we're still a young organization, but our org structure is fairly mature just by virtue of building a regulated firm. And so I've come to appreciate that. I've spent a tremendous amount of my time doing what I think CEOs at fairly mature companies do, which is, a mix of stakeholder management primarily, which is like investors, regulators, shareholders, employees and it's a depressingly small amount of strategy by comparison. But at this point, I've spent enough time talking to customers that I have a fairly deeply ingrained sense for what they need and want. So I need that a little bit less, although I obviously still cherish the time I get exposure.

That's a great answer. I interviewed somebody recently who wasn't trying to start a startup and they didn't know what it meant to be a CEO. They hadn't thought about like, what does it mean? What kind of CEO do I want to be? I think a lot of it is just getting the job done.

I think that's definitely true when the firm is young. I think in my case, I separated between what does a good CEO, bad CEO look like per se and what does the job look like? I have always been really, really interested in this question. What does a good leader look like? And it happens that in doing that, I've paid a lot of attention to the CEOs of the companies that I've worked at and tried to emulate and borrow or avoid the things that seem to work well or didn't work well. So maybe the answer is like, I had a very clear idea about style, but not necessarily about the actual day-to-day doing.

I love the distinction that you make. Did you come up with an answer? What you thought a good leader looked like that you wanted to emulate yourself after?

So I definitely consider this an active area of study for me, I don't have a final answer. I was super interested in this question of, “what does a good leader look like?” from my first tech job. Because, again, the CTO who I mentioned earlier when he hired me, was like, "And by the way, our CEO is really, really good, and he's part of why you should come and join us." Then the company was acquired for $100,000,000, which was after a pretty intense recapitalization, which is not a good outcome. I think I got $10,000 out of the sale, which is not a good outcome.

That really got me thinking. I was like, "Well, that's super interesting. How was the CTO so wrong? Why did he think this guy was so good and then we were led to this really mediocre outcome?" And then having been then immediately afterward fired by Allen's co-founder, I developed some different feelings about behaviors that I didn't like in CEOs. Then with Standard Treasury, it was a mixed bag, because I really did feel like the founders did a really good job and they were just too early to market and there was not that much that they could have done differently. Short of basically setting the company up in the UK, to begin with, the market simply was not there for them. So, visionary, great thesis, I obviously rely on everything that they did, but I don't think that they did anything wrong other than just being at the wrong time. 

They're individual lessons that I take, but that are very tactical and high-level. But also, by virtue of that company having died while it was still fairly small, I also didn't get a sense for how it would scale or what their leadership styles would look like in a mature organization. Then Airbnb was super interesting because in between Standard Treasury and Airbnb, I worked for the chief architect at Standard Treasury because he had gone on to be VP of product at Xamarin before Xamarin was acquired by Microsoft.

So that had been fun because I had liked working with him at Standard Treasury and getting to work with him again in a different environment is also really interesting and fun. And he has a really interesting leadership style, which I can only describe as like,“chaotic good” on the Dungeons and Dragons thing. He's so willing at any point in time to just be like, "Hey, why the fuck shouldn't we do this?" And you could be like, "Because it's a crime." And he'd be like, "Yeah, but what are the odds that anyone would find out?" (chuckles) And he's just, he's always willing to push everything, but out of a sense of glee and joy rather than mischief. 

He's like a, I don't know, low-key as CEO almost. And then Brian Chesky at Airbnb is the model that I think I try to emulate the most because as miserable as I was at Airbnb, a lot of my issues came from the engineering organization specifically.

I thought that Brian (Chesky) did a really, really good job of running Airbnb and keeping people inspired. He did that by being funny and authentic and open. I think there's a lot to be said for just being really honest with people.

I think one of the things maybe if I think back to that first CEO, I think in some ways he wasn't honest with us about where the firm was, he was a cheerleader and I think that works for some people, but I would rather he was more candid with us. And then you and I talked about the leadership thing a little bit too, because you have that wonderful post like, "Yeah. None of us are on the same page about what leadership is or what it means.”

We all talk as if we're on the same page but I don't know that we are all on the same page.

Yeah. And it's just like when I draw reference to these various characters, they just happen to be the people that I've been exposed to and so they are the behaviors I want to borrow from and the behaviors I want to avoid. I feel like if I spent more time with others, I'd borrow more from them or avoid other things with them.

We have a couple of executive openings and related to what I was saying, having a really structured culture interview, we're trying to structure more of an executive interview. That's like an aptitude test for the challenges that come with being an executive that are not discipline-specific. I don't care that you're VP of engineering, whatever. I want to know, as a VP-level candidate, how do you work with other VP-level people within the company?

One of the things that came out of that as Maria and I were working on this, was her drawing reference to your blog post and saying, "Are we actually all on the same page about this in what leadership is?" I put forth my incredibly basic model of leadership at the moment, which is, a leader is someone that other people want to follow and they have to want to follow that person for a reason. The three reasons that strike me as the most common are because that person is incredibly charismatic, because they're incredibly competent or because the vision that they are in pursuit of is incredibly compelling. You can get two out of three or all three or one out of three. But I find that that model explains a lot.

I love that you all are doing that. I wrote that post hoping people would do that because I want to spur a conversation so that you all did that, is incredible. So just a couple more questions. I could talk to you forever, but I'm going to end on two more questions.

I'm worried, we're running out of time and I feel like we've only gone through a third of the questions that you sent me.

I skipped over a few in favor of some other ones. I thought the places we've diverged have helped to understand the regulation and context of the financial industry, which I think tells a lot about how you have to operate as a CEO.

Well, what's interesting about that is actually that I think we are iconoclastic in that regard. I don't think that within the City of London, part of the reason the regulations are there is because people do not have cultures like ours, right (i.e. firms that really go aggressively in favor of adhering to regulation and playing nicely). I'm sure it'll make the regulators' lives a lot easier, but it's not common. A semi-antagonistic relationship is by far the norm.

Okay. I'm going to focus on a couple more last quick questions. So what is one of the biggest leadership challenges you feel like you faced as a CEO?

So there's as a CEO and there's as a founder and they're related.

But they're not the same thing.

Right, they're not the same thing. I think that the space where they overlap is hiring executives. It's really challenging, especially if you are a first-time founder. Even if you’re not a first-time founder, if you're doing anything in an area that you're somewhat new to, you have to hire people in a discipline that you yourself are incompetent in, probably, right? And you have to do that like 10 times as the company grows. So what possible business do I have hiring a chief risk officer? I don't know anything about risk! I do at this point because I've been doing this for four or five years, but like the first chief risk officer we hired, I was like, "So tell me about your approach to risk?"

The consequence of that is that the stuff that I knew well, like engineering, I really feel like we got a slam dunk with our VP of engineering. He's an incredibly solid guy, really structured, incredibly sweet and kind and caring, everything that we were looking for. But with risk, we got it wrong more than once, with finance, debatable, whether we got it wrong or not. I certainly wouldn't argue that we got it right and nailed it. 

But again, I think that maybe is less surprising because as hopefully is obvious, we were spending a lot of time thinking about it before we hired anybody, but it's really challenging and it's frustrating because it's such a market-driven thing, right? You want to spend almost infinite time with someone to really make sure that you've got the right person, but they either are on the market and actually do “got to get paid”, so they can't do that forever. Or, they're working for someone else and they don't have infinite time for you. 

One of the things that's really interesting is talking to some of the ex-operators who are our investors, like Paul Forster who said, “the best people that I hired, we basically spent almost two years trying to get.” I increasingly really relate to that. It's so frustrating because there definitely are people that when I meet them, I go and find their LinkedIn and I put it in a special folder of my bookmarks. I'm like, "I will try and hire this person at any point in time, right?" But sometimes you just need, whatever, you just need a chief operating officer and you have to go out to the market and find someone and speed date, and yeah, it's really hard. And when you fail, you feel really bad about it. It's hard not to feel like it's a personal failing.

Yep. I love that you talk about how hiring execs is really hard. It's tricky. One last question, so if you could go back, what advice would you give pre-startup founder and CEO David?

We spent a bunch of trying to go big out of the gate and that would have worked in the States, but it does not work in Europe. So by virtue of having tried to raise a seed and failed, then done a pre-seed, when we went to raise the seed, it was a lot harder. If in retrospect we had just done the pre-seed and the seed, probably would've been pretty straightforward because we would've been at least as impressive as we were before, but more impressive. Whereas some of the people we talked to were like, "Didn't we talk in 2017? It's been two years. What have you guys been doing?" And we're like, "We have no money. What do you think we've been doing? We've been trying to raise money."

One of the things that's come out of that for me is, that I've realized there's an epic amount of revisionism to all companies' histories, all startups' histories. Anyone who says, whatever, founded 2018 and they just raised their Series B. It's like, "Okay, sure. But actually, if you dig in you're like, "This guy has been working on this since 2015." There's an additional three years here that you're not seeing. And that's not always the case. Sometimes people do, in fact, just explode onto the scene, they get super lucky and everything goes nuts. But often, several years precede that.

The thing that keeps me from beating myself up too much is the valley of evil that Airbnb went through from 2008 to 2011, where it was just like, I don't know what it was, six people, very small team, not a lot of money, no one had any confidence in them, the cereal boxes story comes out of this. And of course, now, it's a 100 billion-dollar company. But the fact that it took them three years to achieve the escape velocity where people felt that it was worth committing more time, more capital, more energy into…three years is a long time. They could have given up in there, very reasonably. It was probably not super fun. Maybe it was, but I have to assume, no one was getting a good salary. Yeah. I'm not saying that we're going to be a hundred billion-dollar company - obviously we're going to be a trillion-dollar company! - but I don't know. And, it's okay for it to have been really tough for a while.

I’m going to end there. Thank you so much for coming on. I really enjoyed our conversation.

Thank you. It's been a pleasure. I love talking to you always.

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