Permissionless Engineering - Stephen Whitworth

00:03

What benefits have you found from intentionally doing things that you're not good at?

00:14

I think a beginner's mind is always the easiest way to see if... Just an easy way to identify potentially dumb or ineffective things that are going on that are only being done because that's the way that they've always been done versus actually contributing to them. So what's a good example of that? I strongly need to think of one crisply, but that feels like the main benefit is no preconceived notions about how something should be done. So you have a little bit of this first principles approach, which needs to be used a bit sparingly, otherwise you end up in this place where you're like, "What even is marketing, bro," stuff where you're trying to-

01:11

Building something no one wants.

01:13

Absolutely, versus I think coming at it from... I think I'll maybe rephrase it to taking skills that you have in other domains and seeing how they would translate to something that you don't know about. So I think a great example of that is I now run the sales team at Incident. There is a lot of product practices that I think could be applied to running sales teams particularly well. I think there is definitely a ton of automation and the sales ops side of the world greatly benefits from someone that can spray Zapier on a bunch of different problems. So I would say that there's usually not having a preconceived notion about doing something and then trying to parlay everything that you were managing to do in your old job that you're comfortable in and trying to see how you can use it to get you ahead.

02:13

It's almost as if the benefit is that you can take the upsides of your specialism, if you have one, and reapply them to areas that are so unfamiliar with that specialism, that your presence there is new, fresh, and can take it to a different level than it currently is in some ways.

02:48

I think it's tricky because you don't want to be the sort of.... And engineers, I think, can particularly suffer from this, but there's engineering arrogance of like, "Sales is really easy. Why don't you just do X?" And the folks that are already in the team that have done this for 5 to 10 years are like, "God, not another one of these. Not another one of these people trying to tell us how to do our jobs." So I think the most important thing to do there is be in the trenches, so to speak, be able to... If you are on the sales team, don't sit up in an ivory tower managing the sales team, sling deals, sell the thing.

03:31

And then at least you have trust and credibility that you can actually do the job required of you and of empathy and appreciation for other people on your team that have maybe the specialism, and then you can try and affix some of the stuff that you've learned outside versus coming in, trying to figure out... Throw away the rule book for sales and come back at it later. But I've been doing it for about six months or nine months at this point, so it's not to say I'm a particular expert at doing this. I've just tried to throw myself into situations where I didn't know much about them and maybe that's the common thread amongst all of this.

04:14

The ivory tower is an interesting thought, because I reckon lots of people must think that... Not that you're in an ivory tower, but surely you're not leading sales. I see you raised from Index, already exciting, there's no way that Stephen is managing the sales team or... It almost looks from the outside like, "Oh, you must be solving really interesting technical problems all day," and then maybe you're a CEO two days of the week, versus, "No, actually, hey Ben, I'm running the sales team. I'm taking what I'm really good at, but I'm also applying it to things that are completely different." It just doesn't sound like the typical narrative at all.

04:56

Yeah, I mean a great example is who pays the sales... Who works out what the sales commission is and gives that to payroll? This guy. Who is the person that is, I don't know, connecting things up, doing a bit of automation, cleaning up CRMs? That's me. And that's not out of some sort of, "I need to be one of the team" style faux mentality, but more just there's literally no one else to do it, that if we took them off... Basically I wouldn't take anyone else off the important work they were already doing to go and do something like that. And my job, essentially... And we work in this accountable exec model. So Pete, my co-founder, runs product and engineering. Chris, one of my other co-founders, runs growth marketing customer success, and sales is my domain.

05:59

And yeah, I don't know. I just feel like there's a lot of stuff to do and not a lot of people to do it. And that's what good feels like, I think, as opposed to beautiful delegated processes where you're not getting in the weeds... It just doesn't really exist, and I was speaking to Carlos, who's one of our investors at Index and I was thinking... I was just trying to figure out the level of delegation that you can apply to areas of the business over time, and in the analogy of spinning plates, is there a time at which someone else spins the plates and I kind of just check in occasionally and see how it's going?

06:51

And his answer was basically no. You always have to keep a close eye on different things. The level of operational involvement sort scales up and down, but you're probably going to be a partner to whoever's working in that area or leading it as opposed to totally delegated. So yeah, that was a long thought on the level of approach, the level of involvement that I think I need to do in particular areas, and absent... Basically nothing's going to run itself, so I would much rather just get into the detail, throw myself at the menial stuff, so the other people on the team can, for example, Pierre and Reese can get on with selling stuff as opposed to clicking the right buttons to set up our CRM correctly.

07:39

I can't imagine that when you were younger... I mean the job title, yes, great. Anyone could aspire to beat up, perhaps. But maybe not the practicalities that you just shared. When you were a lot younger, how did your parents influence your working journey and your choice of work?

08:04

Good question. I'm sitting in my parents' house right now, so I don't know if there's any embarrassing photos that could be seen behind me, but they'll love to hear the answer to this. So I think my parents were... So I was born in Singapore, so I lived there until I was about seven or eight years old, and then my mom is Canadian, my dad is from Sheffield, and immediately from the start I was born into a somewhat international family that had thrown themselves at, I guess, an unfamiliar situation, which by my mom's account was not particularly enjoyable at the start. And then over time, after they went back after six years or seven years, my dad sat me down and everyone was... I was crying. I didn't want to go home. My mom wanted to stay there.

09:05

So I think maybe the earliest thing I learned from them was, I don't know, going into unfamiliar situations, which at the start might not be particularly enjoyable, but can have much longer or much more enjoyable payoff on the long term. And I know some element of grit or resilience to that. I don't think it's necessarily the same grit or resilience that you'd get, say, going through something truly hard in your life. That was not hard from a emotional perspective, but was hard from a unfamiliarity perspective. So I'd say that's maybe the first thing I learned from them.

09:46

And then I always remember something about my dad when I got exam results, be like, "Oh, I got 87 out of 100" And then his immediate response would be like, "Well, what did everyone else get?" Which is success and achievement is... You might not like it, but is kind of relative. So just trying to use other people, I think, and their achievements and what they've managed to do as a little bit of a motivating force. That was always just something that came through very strongly at school, was just the push from my dad to look sideways at what other people were doing, and I guess not get complacent. And then ultimately they're just very good people, kind people. Would aspire to be like them when I eventually grew up, but we'll see when that happens.

10:47

When did you first recognize that you were fostering an inclination, because it's inclinations, ultimately, that end up manifesting in our work, that we kind of tinker with something and then it might turn into engineering or we think about our relationship and it might turn into something else. When were the earliest moments when you started to foster your own inclinations?

11:12

Yeah, I didn't try particularly hard in school, so didn't pay tons of attention and effort. Did okay, but then ended up going to university. I think that was the point at which I was like, "Oh, I might not do great if I don't put some effort in here. This feels like a crucible moment. Shall I apply myself?" And that was maybe the first point at which I... I guess I learned how I liked to learn, versus at school, it was very, "You will learn in this specific way," which is around write things down and then you'll have this revision approach versus I don't know, a university, you can turn up to lectures, you can not go to any of them, you can use a laptop, you can write stuff down. I think that freedom was the point at which... That freedom allowed me to get a bit of the inclinations of wanting to apply myself.

12:16

So maybe in university. And then I think I was of dangerously close to becoming an accountant at one point. No negative view on accountant or anything, but more just I think I nearly went into something because everyone else was doing it. I remember how I got into software engineering and data analysis and stuff was my brother, prolific prodigy genius level engineer when he was young, was always trying to get me into software engineering. I was like, "Yeah, this sounds cool. I'm up for it. Where do I start?" And then would immediately plop down a beginner's guide to C++ or something, which is actually about 450 pages or something long. So I was never like... Took the step to go into it, but I was always interested.

13:14

And then I think my girlfriend now wife went away for the weekend when I was in my final year at university and I was just bored. So I think at some point during the weekend, I was like, Matt, my brother, I think we were talking about engineering, so I decided to just try and give it one last try. Found this website called Code Academy, which was amazing. I think I learned some Python, built a tic tac toe game or a to-do list or whatever that you build in your first go. And then I think at that point I was hooked because I'd now managed to connect...

13:56

Engineering feels freeing because you can build something permissionlessly and then distribute it to an arbitrary number of people. And that had just not felt the same way of something like accounting or whatever I was planning to do. I think that was the point at which my inclinations maybe got of fired up a bit. 

14:19

At this point, once you've figured out what the inclination is, what are you truly optimizing for?

14:28

Yeah, good question. I think I was probably and might still be quite a status driven person and that I think I wanted to go into investment banking because that's what all the smart people did, and you earned a lot of money, which I guess is also good, but oh wow if you work for Goldman, then you know must be the crème de la crème. So feel like I've always been a little bit status motivated, even though I don't think it's particularly healthy to be. I then think that... So that was maybe the default path that I was going on, was this status motivated, semi-final motivated career path. I then think that I moved on to tech, and the way I got into tech was essentially I built a few things for some people. Then I found this startup called Hailo, applied. They had a little contact us form on their website. And I think I said, "Hey, I'm a data analyst. Can I come and do an internship?" Or something like that.

15:37

And essentially I got an offer from Ernst & Young to join them the year after I graduated. So I was in this purgatory period of needing to fill time. So at that point I was like, "Oh, well this tech thing, I've learned to build a few things, I've made a bit of money. Shall we just try it out for three months and see if it works well?" So that was maybe the route into how I made it into tech. And I think the stuff I was optimizing for there was honestly novelty, fun, the unknown, because I'd previously done an internship at Ernst & Young, thought it was fine, but not had my brain set on fire, so to speak.

16:25

Versus back in 2013, when I did this internship, Hailo was an app where you could essentially hail cabs by pressing a button on your phone, which was now not particularly impressive, but back in those days was revolutionary because this was the time... Uber was just coming up, a few others, and that felt like a very meaningful thing that could change cities. So I guess I was optimizing for novelty and impact and trying to switch, maybe consciously, a little bit away from stuff that I might not have enjoyed, but would've given me more status, but who knows? It was a long time ago.

17:12

Did it take you in the direction you wanted?

17:17

Yeah, absolutely. I think I would've been woefully unhappy going and doing that career. Not because I think it's a bad career or it burns people out or anything like that. It may do. But I think I've spent the last eight years figuring out what I really like to do and what I don't like to do. I'm pretty impatient, so I like to work quickly and at speed. I like jobs where there is high of marginal output for hours put in, so I need to feel like I'm having some kind of immediate impact, which is then linked to speed. And don't like to take myself too seriously. So all of those things, I think, lead me a little bit towards going to a world of technology and startups and away from something a little bit more corporate. But hey, we've hired plenty of people that have worked in those sorts of environments and loved it, so it's hard to tell.

18:26

There's the self reinforcing bias that I took the right decision and I'm just going to say a bunch of reasons why I feel like I took the right decision, but I'm definitely happy with where I ended up. And I guess maybe the last thing I learned through it is that life is quite random. I started this company, Incident, where I'm at now because I met and worked with some people closely. But if there had been a reorg or a layoff or they hadn't chosen to join, I might not have been here doing what I'm doing today. So essentially try and align directionally with where you want to go and then just accept randomness that comes along the path and embrace it. I think it's hard to have a plan

19:18

If we fire through what happened from Hailo. Because it's really interesting, you go to Ravelin then you go to Monzo, and obviously you start Incident, how did you formulate the key decisions at the different moments there? You've got to leave Hailo, where you've taken this risk, not to go to Ernst & Young in the end and stayed. You're then starting Ravelin, but then you're leaving, started to then go to Monzo and starting again. Maybe starting at the beginning, how have you formulated those professional decisions and have you used any type of, I guess, models or just ways of thinking to help you make them?

20:02

Yeah, I think don't... What's a good way to answer this. I think the parts of my career where I've decided to make changes have usually been to do with, I guess, novelty and learning rate. And it feels like so when I was at Hailo and I decided to switch was I'm working in product teams, I'm enjoying the work I'm doing, but there seems like this opportunity to attack this massive problem that I have no idea how we're going to solve, have a little bit of a direction, but wow, it just feels like there's just this huge thing in front of me that I want to go and solve. So immediately, I don't know, being tempted away I guess, is how I would've thought about it versus a specific plan or wanting to go, "We're going to start a business. What are the best three problems we have? Okay. Let's pick the number one."

21:07

Much more like a gut instinct and a vibe. Then I think from Ravelin into Monzo, love the people at Ravelin dearly and had spent best part five years building something meaningful there. The parts out of Hailo, a bunch of people went and started a company called Starling, which then split off and became Monzo, and then a bunch of people went and started Ravelin and a few other started different companies. So there was always a bit of building a bank sounds like a hugely interesting challenge. I've helped build something meaningful at Ravelin, but this also seems like a great opportunity as well. So I guess feeling like I'm not leaving anyone in the lurch and just being irresponsible and just dropping stuff and moving on.

22:04

I never wanted to do that at Ravelin, but then ending up at Monzo, I guess because the challenge was really important and interesting, but also I knew that I probably wanted to do a company in the future as well. And working at a much bigger company, honestly, is a good way to just broaden your network and meet lots of different people that I hadn't met before. And then of Monzo to Incident was I think a lot of the same of... Monzo taught me that I think I'm very much a super early stage person. I really love chaos. I love ambiguity. I like wielding a bunch of autonomy and power to just make pretty unilateral decisions to go fast on particular things. And that's just not a productive thing to do on organization of thousands of employees with many regulations that apply to it for good reason.

23:15

And I think that spending a couple of years at Monzo was a perfect way to learn that about myself. Really enjoyed my time, but then I guess saw a little bit of a glimpse of the future of how this particular problem of stuff going wrong in organizations manifested itself, and I guess how it got solved in a way that I hadn't seen it done before. So there was, again, the temptation, gut instinct started kicking in again of I feel like I can potentially learn a lot more quickly if I go and start this thing, so should I do it? So that was it. And yeah, I don't feel like I'm going to... I'm learning so much right now that I don't think I'm going to have those feelings again for quite a long time, but I probably said that before. So we'll see how things go. I've definitely no plans to do anything different.

24:12

It sounds like you're, throughout that whole journey, having this constant conversation with yourself that doesn't seem to be stopping, that's informed by your inclinations and the passions that you have and your impatience and your desire for learning. But then it's also informed by, I guess, the different challenges that each one of the environments presents to you. And it's almost like they're trading gifts with each other as you go.

24:47

Yeah, I think the past year at Incident has taught me that actually gut instinct is legitimate and can be very useful. And I think that had not been something that I... I didn't know quite how much weight to put on it before, whereas I think for early stage hiring, I think for example, is a highly gut and instinct driven process as opposed to a scientific scorecard, highly, highly rigorous process. And I think that's fine. That's stuff you have to optimize for. And I think I just didn't know how much weight to apply to my gut versus advice from friends, versus what the rest of the world... Sensible career path in the rest of the world and stuff like that.

25:40

And I think that I am of unashamedly a more gut driven person than I was before and very happy to listen to myself as to whether things feel comfortable, uncomfortable, a potential candidate would or would not do well. There's obvious biases and everything that you need to be checking against and running this background thread in your head for it. But I think that is the main difference I've seen over the past years. If I'd gone back, I think I would be more gut driven in more of the decisions that I made.

26:21

Is there anything that you've done that has enabled that to get better in some ways? Because it's so really very difficult to listen to ourselves and our gut and to have that acorn of confidence that we run with that we allow to get bigger and bigger, but not overtake our ego, and listening to it is just so ridiculously difficult. And it sounds like the environment's helped you get there. Is there anything that you are doing to tune that and improve your gut instinct and your ability to listen to it?

26:57

Yeah, I think there's a few different things you can apply. So one is the calibrating the amount of data that you might need to see to make any particular decision. So good example would be anything go to market related or all that side of stuff. For example, if you're trying to analyze your ideal customer profile based off of maybe 50 or 100 customers you have, do you need to go and speak to every single one of those 100 customers, or can you instead get a directionally good guess from speaking to maybe 10 or 15 and use your gut instinct to complement a bunch of the stuff you already know. And I think it's about, in that scenario, there is always generally more data that you could get on any problem that you're trying to solve, but getting more data is the expensive part, and trying to understand where you are on this S curve of get more data to be more accurate. But I think you can actually just use your gut to jump up a bunch of that accuracy curve if you want to.

28:14

When you think about trying to improve it, it's just about knowing where it's good and where it can complement more scientific approaches. I guess the second thing you can do is just a bit of about how good were you really? And this is the classic thing of people that predicted the 15 of the last three recessions or whatever, is that you actually probably should be held accountable to predictions that you made in the past and assessed against how likely you are to be correct against those. And I think that's really easily doable from a hiring perspective. They've used Greenhouse or Lever or whatever, were you a yes, a strong yes or a no against a particular person? How aligned are your strong yeses with performance internally after it happens? Are your yeses actually should be no's because in reality they just do okay, but you are never really that excited about them from the start?

29:18

That forms as a useful calibration mechanism to say, "I mean, yeah, you have your gut, but here's some relative objective evidence where you used your gut and you made either a really great call or a really bad call." And I would say what we've seen is the people that were strong yeses in our hiring process are generally pretty well correlated with performing the strongest. So I've tried to use that as a... There's something here, but definitely not as some kind of oracle where you think you're always right about everything. That's definitely not what I'm trying to get across here is that Stephen's gut is definitely right. It's more just a useful complement to other approaches to making decisions as well.

30:05

Sounds like feedback loops too. You're taking a feedback loop that isn't currently measured, that isn't quantifiable, it's just in the ether, and you're kind of drilling it back into your decision making in some kind of way, just at least creating some kind of feedback or information that you can then use to benefit the future in some way.

30:32

Yeah, absolutely. I mean, it's just sensible decision making, isn't it? Pay attention to information? I think this is the thing that pissed me off a lot about political discourse is the concept of you turning and why that is viewed as an incredibly bad thing. Whereas in reality, just, I don't know, changing your opinion when you receive new information is pretty much the only logical thing you can do. So I guess maybe that's something else that's interesting is I've noticed in Incident, we are a lot more intentional about the accuracy of the statements we're trying to make, and the, say, how well finished a particular proposal might be in the point of which we'll be like, "Oh, this is 40% done," so I'm looking for directional feedback as opposed to, did I say this in the correct way or is this spelling wrong and trying to be a bit more meta about how confident am I in this assertion, is it a gut feeling? Is it something that I would like you to go an action and do?

31:43

So it's kind of like metadata about what we're saying and decisions that we are trying to be a bit more intentional about so people can decide... So other people can react to them appropriately. And I think that's something that I haven't seen many other people do, and it's generally a little bit more coded and you have to back it out of impressions or expressions or any of that sort of stuff, but I like it because it means that people have more context and they can decide what to do in a slightly better way, and like you say, go back around this feedback loop.

32:17

It's like this beautiful truth. It just is the truth. You're just seeking truth. It's almost as if it comes out of a data layer, it turns into a human layer, and all of a sudden it can't exist as truth anymore, but it has to have some kind of left or right or yes or no onto a positive or negative, whereas it almost feels like we're at a time where just taking that qualitative thing and treating it as truth, trying to find the truth can be your superpower rather than turning the spin on it, or just trying to sound confident in your assertion when perhaps actually it needs more scrutiny.

33:02

To you now, what makes work meaningful?

33:10

Yeah, good question. I think the thing that makes work meaningful to me is maybe two things. One is progress. I think in when you're a GCSE student or something, you have this careers interview where they sit you down and they're like, "Oh, what do you want to be when you're older?" And you could be a mushroom farmer or an accountant or a theater actor or some of this stuff. And I think what I've realized is that I don't really care the specifics of what particular industry I work on in technology or problem, as long as I get to make rapid forward progress in solving that problem. I hate the feeling of treading water. So a big problem where I am making meaningful progress is itself meaningful to me. And then maybe the second thing is the cheekiest answer, but doesn't make it less true, which I think is the people that you get to do it alongside.

34:16

When we were starting Incident, we were honestly thinking that we should maybe bootstrap it at the start. Making a few hundred thousand dollars a year in revenue in the first few months, there was definitely a path to like, "Hey, we could just build this as a small thing and we could take it and hire a team of five and that would be it. We could do what we wanted." One of the key contributors to us deciding not to do that was we know all these amazing people that we would want to hire, and that would mean that we only get to hire one of them or two of them, and only at the rate at which we make revenue to pay them, which is not itself a great advert for going and starting a VC business.

35:06

I wouldn't say that's the only decision criteria that you should use, but it was something I think that was particularly meaningful to us was we actually have a good network of amazing people we've worked with. And it would just feel like a bit of a waste if we spent maybe 5 to 10 years, not being able to do it with them as well. So yeah, the feeling of camaraderie, sharing lunch together, all of that stuff to me was a meaningful part of a part of starting this, and I think if it all ultimately failed and I still got to spend years working with the people that I'm working with right now, I think I would still be happy at the end of it, versus if we were crazy successful, but as just a small team of three, it would've forever felt like a bit of a missed opportunity in my mind. So I'm sure the team will hear this and roll their eyes, but doesn't make it less true.

36:14

It reminds me of the hedonic treadmill where the there's an argument that the more money that we earn or the further up the chain that we go, the more expectations that we then have of our life. But in some ways it almost sounds like you've jumped up on the treadmill, put two feet on both sides and are letting the treadmill fall beneath your feet. And I recognize that it can't be perfectly that way. Have you experienced that kind of hedonic treadmill where you're just constantly... You almost feel like as you go up the layers you're wanting... Naturally your expectations get bigger the more skills that you get, the more progress you make, and have you figured out a way of getting out of it?

37:05

No, and it's really frustrating. So I remember the first Stripe payments that we received for Incident. I was sat in this room, so it was during lockdown, and I think we'd built, we'd integrated Stripe in, I don't know, a day or something because we needed to start making some money. And at that point I was like, "Oh my God, someone's paying us 150 pounds a month for our product. Oh wow, 750 pounds a month. That's amazing." And I'm not being sarcastic. I was genuinely so happy that this had happened. And now if now I wake up to an email notification where someone is paying us 500 bucks a month and I'm like, "That's pretty cool." But I then go up and I make my coffee and I go for a walk or whatever else I do. And I don't know if that feeling has been dulled a bit, which is frustrating because at the stage of company we're at every customer still is an achievement. We can know most people by first name.

38:16

And I just think it's raw human nature to acclimatize yourself to whatever's going on and be less and less impressed by the same achievements over time. I don't really know how to change it that well. I think one thing that we try and do at the company is... So we have a gratitude channel, which sounds very LA and I guess doesn't fit particularly English, humble, self deprecating model very well, but we try and use it to celebrate, I guess, wins that people have had things that we would like to thank other people in the company for. And I guess trying to hold up parts of the organization and show light to maybe... An achievement does not need to be signing a million dollar deal or launching a particular country or something like that.

39:26

A great example is we held a sales event in our office last night and it was the first one we'd ever done, and four people helped us make that happen, and that's really great, and we should celebrate that as a legitimate achievement and of hold them up for it. So, yeah, I think appreciating that I don't think at a chemical level it's very easy for us to get off the treadmill, but then you can just still hold up small stuff and medium stuff and make a big deal out of it, and hopefully that's some way of the novelty of everyone's individual achievements and the newness of it stops you from being bored or dulled against the stuff that you're a bit more used to. But I think in short, no, it sucks. I would like to be a more appreciative person, but I think my body's fighting against it.

40:25

It sounds a lot like expectations, and there are so many expectations that are set of a CEO, and especially a CEO who's running a VC backed startup, because the odds are firmly against you and not in your favor. Reminds me of the salmon going up the stream, unlike only one of them making it, and there are just these systems in nature that mean that the VC is doing nothing wrong there, it's exactly what they should do, but it is just the truth, that power law means that only one or a small number will make it. How do you maintain your own self and your own work satisfaction and your own expectations, knowing that you're part of that and that it might not be you who makes it,

41:26

Yeah, we've thought about this a lot, and we like to hire what we call of pragmatic optimist and that the default outcome is that this all probably goes to zero or trundles along and doesn't really make any money. But if we truly thought that we were one of those people, well, why even bother? Let's just all go get some jobs at Google and we'll all be happy in very well off in 25 years. So I guess a bit obstinateness that while we're not going to be one of those and it is within our power and our control to make small changes every day, that we aren't going to be one of those companies that goes to zero.

42:16

Optimism is definitely something we explicitly hire for. Do you think that there is good in the world? Do see the bad in everything that you... The bad in every mistake or do you view it as a bit of a chance to learn and improve? So surrounding myself with other optimists. I think I maybe started off my career being quite pessimistic and negative, and honestly I think English and British culture doesn't help you with that.

42:44

It's not helpful.

42:45

Yeah, absolutely. Versus I don't know, you spend some time in America and it just genuinely is a bit different. And I changed my viewpoint on this many years ago before I started spending more time in the States, but it's refreshing to see that there are literally countries full of people that think slightly differently in that way. And then I guess expectations management, the personal side of stuff, I think being a CEO or founder or an exec at any early stage company is essentially being at the end of a treadmill of an infinite amount of generally pretty valuable or highly leveraged work. Because of what you're doing in your role you just are going to be able to accelerate a lot of things and you're generally not working on super menial things.

43:38

So it would be, "Should I go and try it and close this, or find a bunch of candidates for this VP role? Or should I fly and go and see our biggest customer and spend a few days with them? Should I take this project team that's slightly struggling a bit and get in the weeds and help them?" Yeah. All sounds great. Why don't we just do all of it? Well, answer is you can't. So I think accepting that there is some point at which you have to draw a line under the amount of work that you are simply just able to do. And I think prioritization is the ultimate skill to learn in a post product market fit company. You'll always have more things than you could possibly do with the people that you have or could hire. And just being ruthless with focus and prioritization is the goal.

44:34

It's very hard to do in practice. My colleague Esther says good prioritization is not finding two bad things, eight good things, and then doing the eight good things. It's the two bad things, the eight good things, and then doing two or two or three of the good things. It should hurt, it should be actively painful. And I think about that quote a lot when I'm trying to figure out which person to disappoint or which thing to slow down or which thing to consciously ignore for two weeks, because you just can't do it all. So it's got to hurt. And then I guess maybe stress, I think, is the last thing that is something I think about a lot, which is just trying...

45:25

I've tried to become more aware of what stresses me out and it's just weird small things like lots and lots of back to back meetings or having a big thing on my mind, which I know is the most important thing for the company, which is not reflected in my calendar as the most important thing or the amount of time I'm spending on it. I think I've drilled it down to the tension between my priorities and observed priorities. If those are too far out of whack, then I start to get quite stressed out quite quickly, and I don't know, just trying to be a bit meta about it.

46:07

There's this concept of... We think about it when hiring, of people that do work and will do tasks and will do them perfectly well, but then a layer of people that think about the work that they do, how they do it, how much time to spend, the speed versus accuracy trade off that you would apply to it, the sequence to do it in, the more meta aspects about work itself, and trying to think in that mode when it comes to the work that I do and how I structure my day, I think is the thing that is the biggest... I don't know, the biggest positive impact on my ability to get my job done is just be a bit more bit more conscious, bit more meta. Time is finite. Everyone's dying slowly and all that. So you just spend your time on the right stuff and be conscious about it versus don't just do tasks because there's an infinite stream of tasks coming. So you better pick the right ones.

47:07

Understanding stress is so challenging. Is Dostoevsky says, I have the quote in front of me, the most terrible punishment for any human being would be if they were condemned to a lifetime of work that was devoid of usefulness and meaning. And in those moments of stress, you are at the pit of usefulness, usefulness and meaning. When has that quote resonated most deeply with you?

47:47

I think that one of the things we ask in our interview process is the concept of hard work. And when have you worked the hardest and why did you do that, and what were the triggers that would make you want to work that hard again? And the first thing that candidates immediately associate hard work with is long hours. I just don't think that is always the case or necessarily the case. And I think if you apply that to burnout, everyone goes, "Oh, well, it's working super hard and very, very burnt out." I think it's actually pretty weekly correlated in my experience with burnout. I think burnout is much more attributable to what you say in the Dostoevsky quote of just, "I'm on an infinite hamster wheel and none of the stuff I'm doing is going anywhere."

48:34

I don't know if there's a particular time where that applied the most. I think in general, it's when I've been working on stuff that I know I'm not good at and have no interest in becoming any better at, and it's not impactful anyway, versus stuff that I'm not good at, I actively want to get better at, and getting better at this thing is the most important thing that could happen for this company. And I think Incident is maybe the positive aspect of that, which is taking, say, learning to sell the product. I'd never sold something before joining this company. I sold maybe the first 60 or 70 deals because there was an impetus for me to get better at it, and high marginal output for hours spent in, versus I think some of past experiences that jobs where it honestly just wasn't that important because I wasn't the CEO. I'm not blaming those companies. It's just structurally, I think, less aligned with what I was good at and what I wanted to be good at.

49:57

And finally, how would you describe your own personal relationship with work now?

50:08

I'd say harmonious in places and evolving in others. So I think a good example is I work to be more fluid and intertwined with my personal life than I think most people are comfortable with. I think that Saturday morning is an excellent time to get some work done, personally, because I'm fresh from a nice, long sleep, I have nothing on my schedule, and there is no one else around. And if I want to do things which require unbounded amounts of time to think about and do... What are the key weaknesses in our go to market motions, or what does the next six months of product look like? That stuff is really, really hard to squeeze in two 30 minutes between a lunch and a review meeting. So I think Saturday is a lovely time to do some of that stuff. So I try and do that.

51:14

My wife, thankfully, is amazing and totally fine with that. I think what the complement of that can be is... Me and my co-founder, Chris, have we have this thing in the calendar called the lunchtime running club, and it's currently being renamed to the aspirational lunchtime running club because we've had it in there and no one's gone for a run at any of those times. And I think maybe the compliment to the intertwined nature of the Saturday working is cool, but is there a way that work can be a little bit less structured in places and you can get those times in for just going for a run and spending more time with people? So I think that's the harmonious side of stuff evolving.

52:09

I've essentially gone from a job where I knew pretty well what I was doing and was evolving skills in a specialist path to my job now is to be thrown into a new situation between every three and six months that I have never done before, rapidly learn to get good at doing it, and then try and find amazing people that can do it, assess them, coach them, partner with them and get them going, and repeat. That's the evolving part of it. And that if you're going to be even more meta about it, I have very little experience at doing this thing that involves me having little experience. So trying to get good at learning and learn more quickly, I think is what I'm trying to work on.

53:07

So yeah, evolving, but overall happy. No fundamental complaints or anything like that. Still definitely enjoying things. Just have never done this aspect of the journey before from a leadership perspective and a role perspective. So everything is new. So there's probably some seasoned vets out there that are looking at me and saying, "Oh, zero to a hundred people is the really fun bit, and then you wait until the hell starts." Ignorance is bliss and I'll operate in that mode on the work side of stuff, because I think just, I don't know, being an optimist, being pragmatic and enjoying the novelty is what I've always liked to do, so I don't want to spoil it too early.

54:06

From Hailo, Ravelin, Monzo, now Incident, I'm really grateful, we've had the time, and I've loved your honesty and clarity and optimism. And thank you.