Episode 6 - Why and how I bootstrapped to £1m ARR!

Seed to Success

How to iterate your way to product/market fit without wasting developer time.

Episode overview

In this episode of Seed to Success, Alastair chats to founder and CEO of Trust Keith, Rory Codrington, who discusses his founder journey and shares how the lessons from previous ventures shaped his strategic decisions for his latest business.

Rory discusses the importance of market validation, understanding customer value, and leveraging strengths to shape the direction and value proposition in B2B. His practical insights on navigating regulatory compliance, bootstrapping, and thoughtful business model considerations provides inspiration for listeners looking to embark on their own founder journey and those seeking strategic guidance.

If you’re keen to hear about the complexities of entrepreneurship and gain some practical advice to fuel your founder mindset, then this one’s for you!

00:01:03 (Alastair)

Welcome to another episode of Seed to Success, and today we have Rory Codrington in the studio, founder and CEO of Trust Keith. Welcome to the show, Rory, thanks very much for joining us, Rory. Give us a 30 second elevator pitch on Trust Keith.

00:01:20 (Rory)

So the pitch. So we help startup and scale ups become and stay compliant with global data regulation. That's everything from GDPR to HIPAA to all the more nuanced marketing data regulations that you've probably never heard of, like the PECR. And we do that by giving customers access to our platform, which automates their compliance to those certification… to those regulations, and access to a dedicated expert who holds their hand and helps them navigate all those grey areas of regulation.

00:01:55 (Alastair)

So it sounds like there's technology and the people side of that supporting or service side of that supporting those startup and scale ups. And I guess when you deal with significant amount of data and you have no boundaries, no barriers geographically, then actually you are opening yourselves up to lots of rules and regulations in lots of different territories.

00:02:18 (Rory)

Yeah, absolutely. And I think that this is one of the, having been in the space now for coming up to three and a half, almost four years now, I think regulation as a solution to solve is actually quite a good one in the grand scheme of things because it's so nuanced, there's so much grey area to it that you can't just sub in a one feature product and you're done. There's so much nuance to it that requires an expert opinion because a lot of it is risk-based decisions that you need advice on because someone's name is going to be against it. And then secondly, the software solution is quite expansive and it's really hard to define where it starts at, where it finishes, and where regulatory compliance bleeds into information security and data protection. Just all these different bits. It's a bit of a knotty problem  to be solving, but I think that works quite well for us because it's something that most businesses struggle to solve and they're always looking at either adding multiple vendors together or just sort of, there's not a perfect solution, there's not a monopoly in the space.

00:03:21 (Alastair)

Is it one of those things that founders don't… may have a slight awareness, but they're a little bit ignorant, or as I say, kind of unconsciously incompetent to what the problem is until a friend, a fellow portfolio company or something is in the news, that creates this awareness of the problem. And therefore is it a harder sell because they're busy on their journey of growing and actually they're pushing it to the lower down the to do list because perception from them is, it's not actually that important until it happens.

00:03:58 Rory

If you're early stage, your kind of understanding of it is quite sort of high level and it's just right. It's a tick box exercise. Or maybe if you're in a regulated industry like finance or health, you know, you've got to get it right. So you're a little bit more informed. But the kind of very early-stage business is not that informed. They see it as a tick box exercise. However, the kind of the later stage you get, whether as you mature or you have more and more requirements, because you're getting security questionnaires from vendors that are blocking you, winning big deals, or incoming investors are saying, right, you've got to solve this, or things like that. That's when you start realising how deep the subject is and how complex it actually is to solve. So we do have a bit of a challenge from like an educational piece of educating companies and customers to the reality of what actually needs to be done. Because quite often on day one they think, oh, this will be done in a couple of months, but by the time they're in the door and they see everything, they're, this is, this is perpetual.

00:04:55 (Alastair)

I want to go into the backstory and how Trust Keith came about because I think some really interesting lessons there to uncover. But before we do, can you give us a feel of how big is at the moment in terms of people in terms of revenue, in terms of whatever you feel comfortable with and also how long you've been going to get to that point?

00:05:16 (Rory)

Yeah, so Trust Keith Limited is 4 years at the end of October, we're completely bootstrap business. We're a team of eleven that we're currently hiring, so we'll probably finish the year at around a team of 14. And we're used by kind of over 60 customers and we're doing just north of a million ARR.

00:06:33 (Alastair)

Thanks very much for sharing that. And is that customers in London in the UK, technology startup scale?

00:06:44 (Rory)

The theme would be their London headquartered but they all operate internationally. But we do have a number of US customers in particular.

00:06:50 (Alastair)

Yeah. So if we wind the clock back before those four years or so, how did you get to the point of setting up Trust, Keith, in terms of the problem at hand, the type of customers, the value of customers, the taking, no equity investment. Can you talk us through what are for you some very clear design principles and how you got there? So maybe wind the clock back as far as we need to to understand kind of where it all started.

00:07:25 (Rory)

Well, I think it originally started back in, I guess when I started my first business in 2014, which was in hindsight quite a classic. What you see a lot of first-time founders do is I go into passion business and at the time I was obsessed with skiing, so I co-founded a skiing meet up app with a friend, we raised a small angel round we went and launched in the States, ultimately pretty unsuccessfully. And then my co-founder left to go back to uni and I kind of plugged away for three years. Same shareholders, same limited company, but ultimately a couple of different, very different products and those at each substantial pivot. I was taking all the learnings I had at that time, iterating it. So one example would be we came back, we were doing skiing, realised, okay, well, we don't want to do something that is very seasonal, okay. Also direct to consumers, that's really hard to get sustained traction, let alone monetise. So started exploring B2B options and that ultimately led over a couple of years to a B2B reward like physical gifting company called WeDelight, which sold to customer success teams and that I got to about £1,000 MRR, I was never really going to run for something. But I think at that final kind of moment it could have been something. I think if that was my starting point and I'd stayed focused and rifted on that, I think maybe it could have been something. But as I kind of closed everything up, I basically just listed all these things and I thought, well, I want to build a successful business. So what does that look like? Well, it should probably be B2B, it should be a must have, not nice to have. There should be good validation in the market already. So if there's competitors or there's businesses in the space that are Series B or Series C, that's actually really good validation. I think it's actually a really encouraging sign to explore further in that niche then ac like average customer value. I thought, well, I'd rather have a business that might only ever have 50 companies, but they're all going to pay 40 grand, 30 grand a year kind of thing, as opposed to all these minnows paying sort of 40 quid a month. That was the thing. And then it was kind of playing to my strengths of outbound sales or kind of pseudo enterprise sales where you're sort of getting the meeting, closing the meeting kind of thing. And that just built up a bit of a picture of, I guess a lens I wanted to solve against. And then it was a case of looking at the opportunities at the time. And at that time I'd been doing some freelance work with CharlieHR as they built out their HR advice service, so they've already got their HR software and they were building out unlimited HR advice service on top of that. So I kind of came in to help operationalise and basically sell that. And that gave me first-hand experience of that, people as a subscription style service. So I initially thought, well, I don't want to raise money because I want to have the control. I don't want that accountability and pressure, at least yet. Until we've actually validated something, we've actually got something that's going to run. So I started looking at something like that, which I knew I didn't need money really to build anything on day one. And I was looking around at the time and there were businesses like Design Pickle. I was looking at unlimited design as a service, pay 800 quid a month, unlimited design. I was looking at unlimited legal support. And this is at the time that the former Twitch co-founder in Silicon Valley, I think he must have raised about 50 mil for his legal tech company. Similar vibes, but different ultimately didn't work out. And there was a few other business models like that. And this was about a year after GDPR came out. And that's where I kind of stumbled across the DPO role. And then seeing the HR model, I thought, well, why don't we just offer unlimited DPO as a service or unlimited DPO advice for Probably like £300 a month? That was a starting point. And then I got speaking with a number of founders that I knew. We did a lot of customer research, a lot of kind of jobs to be done, research to really unpick, at least this time around, learnings of what are they actually trying to solve, what do we actually need to meet the needs of? Got the first couple of customers and then it was really game on then to work out what they actually really wanted. It was then that we really pulled out a product from them. And then it's taken this long to really finesse that and iterate that product to a point of like, this is exactly what it is, this is what it can be. And now we're a lot more focused on kind of resolving and taking that to fruition.

00:11:48 (Alastair)

So many things in there to unpack. I can't keep up with it. I think one of the first things to pick up on is kind of the more immediate in terms of, I think, GDPR. I think was it May 2018, the revised regulations came out. Do you think that helped create massive awareness for the requirement of a data protection officer and just actually was maybe a catalyst for the need of the type of business that you've built?

00:12:17 (Rory)

Oh, 100%.

00:12:18 (Alastair)

And without that kind of macro legislation, it wouldn't be as…

00:12:24 (Rory)

It’ wouldn’t as front of mind for a lot of businesses. I think pre-dating GDPR, there's still plenty of other data regulation. It just wasn't sort of mass market or mass informed. So even today, GDPR is just one of many regulations that businesses need to comply with. It's just like one of the most well-known ones. So it's more just, I think it's an inflection point of market awareness of data processing rights. Okay, that's a thing. Now then, I think the GDPR has set the precedence for what others will do globally. Europeans have always, from a regulatory perspective on data, have always been quite firm and kind of done it quite stringently. So I think every other market looks to be GDPR is like, well, that's the top of it. But even if they start doing things equivalently, there's just added and added complexity for businesses. And I think it's so inevitable that there's more is going to come, which is, at least from our perspective, a good place to be.

00:13:21 (Alastair)

So if we wind back again. So your first venture was a skiing meetup. Approximately how much money did you get in terms of funding? And at that point, is that what put you off when you set up Trust Keith to go, actually, I want to have more autonomy and do it a slightly different way. Was that what put you off? Or was there something else around that that said, actually, I'm going to bootstrap this business?

00:13:45 (Rory)

It’s a number of things. I think when you raise, and there's obviously a different spectrum of investors on the far end, you've got quite aggressive VCs who are like, show me how you can build a unicorn or nothing, and then you try and trend down to maybe more patient angels or loans and that side of things. But in most cases, if you're raising, you need to build a vision that it's at least going to be a ten mill ARR business, or you're going to at least try and convince them it's going to be 100 mill ARR more or larger and larger. And I think it's not like you couldn't solve to create a business like that. Of course you can, but it's more that just a very different track that you're playing on and forcing yourself to play on, because the moment that money comes in the bank, you've got a timeline and most businesses run out of cash. It's not because they haven't got something that's working, it's just they run out of runway to iterate, find product, market fit or get things really working. Most businesses run out of time. So I think this time around, I thought I didn't want time to be a constraint. And then there's all the other side of things, of, well, control is really important to me this time around and also looking further ahead and taking a slightly more maybe. Obviously all these views are so biased from my own experience, but it's that sense of if we one day want to sell the business, what's actually realistic outcome here? Am I better off raising, trying to do a Hail Mary over sort of 8/10 years and end up owning sort of 20% or very methodically being consistent, working within no knowns, building something to five or ten mill ARR and selling then. And I think part of the thinking with raising investment was I didn't want to raise the floor of what was acceptable to sell for, because as a bootstrap sole founder who has decent amount of equity in the business, I can solve for a similar personal outcome at a much different scale that feels a lot more realistic than someone who's on the venture track with three co-founders. They go through three rounds of funding, they've got option pools for everyone, and they're down at 25%.

00:15:51 (Alastair)

Non-existent, yeah.

00:15:52 (Rory)

And it's just the outcome they need to get. The equivalent outcome is almost like five or ten times. And it's like, what's harder? Selling something for 15 or 20 mil or selling something for 250?

00:16:02 (Alastair)

How did you coming out of the two previous ventures and then going into CharlieHR consulting, how did you…. Because we were talking before this recorded about lessons learned and reflecting on previous ventures, how did you actively take those reflections into this new venture? And so what I mean by that is it's very clear that you were focused on B2B, you wanted a high ACV, you wanted to be bootstrapped. You've got these principles you wanted to live by from these past ventures. How did you actively kind of bring those to the forefront and go, I'm going to sit down, I'm going to develop this blueprint for this new business. These are the principles, and I'm going to find a job to be done and find this rather than to your own words. Previously you started something with a passion, which was skiing, some very methodical, very consulting led approach to do that. How did you actually take that time to reflect on yourself, to bring that out?

00:17:09 (Rory)

There's a couple of things. Well, I started working with a business coach, James Eder, who's one of the founders of student beans. So he helped kind of iterate that thinking as well as hold me accountable to kind of move things forward. And it was also at that time the founders of Charlie HR , Ben and Rob that they were really, really supportive in, I guess taking time to sit down with me and kind of ideate on some of the thinking that I had, but I was also just intentional of writing it down. If this, then that, and using that as a lens. So it all kind of ultimately there's so many different moving parts to it, but that I guess made it happen because what was the equivalent for you when you set up the business in terms of like, did you have any initial constraints or…

00:17:55 (Alastair)

Well, cash, cash resources was the constraint, was the primary.

00:17:58 (Rory)

That's an constraint.

00:17:59 (Alastair)

Which creates innovative thinking in its own right. So in some ways is my second run at this type of business because I ran a very similar business in PwC in London or business unit. And so you kind of see what works. Yeah, I guess kind of. You naturally see what if you're in it every day and you have the frustrations of being in that and seeing what works and what doesn't work. It's those frustrations that drives a change in model or an innovation or a desperate passion of doing something a different way. And I guess it becomes so natural to know not to do something in that way. Right? And you define a new world, a new norm of how you do that new operating model and how you go about it.

00:18:47 (Rory)

It's one of those things that people don't often reference of… Sometimes people want to start a business because they want to work for themselves. That's okay. It doesn't need to be. You see a lot of these investment decks where it's like, oh no, this AI niche that I'm solving, that's my passion. It's like, well, you can try and kid the investors, but is that really what's leaping you out of bed in the morning? No. And it's okay for it not to be. And it's not that I don't care for data regulation, I do in a different perspective. But my passion is more just building a successful business, having great people in the team, solving a hard problem, building a brand, regardless of the industry that we're in, that's really exciting. And I think there's so much dogma that has to be a passion thing. I think that often puts people off about, well, I'm not passionate about crms, why am I going to do that? And it's like, well, there's independence you can build, there's a brand you can build. There's always other things that are just as viable.

00:19:38 (Alastair)

I think personally creating something out of thin air or manifesting something from your imagination is extremely fulfilling because you are literally creating something from nothing. Right. So I think that's a really fulfilling act and something to work towards. But there's also something that's really rewarding is hiring people and training them in whichever kind of. For us specifically, it's training them to become chartered accountants. And hey, the world, despite what some people think, needs more chartered accountants because they help people navigate the challenges they may have. Right? So the world, half of the FTSE one hundred are CEOs or ex chartered accountants. And to develop a person, a human being in a profession, whether it's accounting, whether it's coding, whether it's data protection, whatever it is, you're educating them, you're giving something back to the world and you're making the world a better place. So whether you have a passion about a particular industry or sector, you can have a passion about developing people and you have kind of a passion about building something and creating. And I think that can be even more so fulfilling than just following a strict passion for a sector or something like that. If I was doing something purely for passion, I'd be doing something in Formula 1. That's what I'd be doing. But I don't think it'll pay me any bills to go and watch a bunch of teams race.

00:21:19 (Rory)

Yeah, but also I think if you're pursuing something as a passion, then it becomes a job or you rely that income has to work, then I think it changes some of the passion of it because it feels like a job.

00:21:32 (Alastair)

Yeah, I mean, we've been going, I think, six years now. And if you're not passionate about something in and around what you do, it's very difficult to have a spring in your step, especially when in some cases, you are sprinting a marathon. Right. Because that's what it feels like as a CEO and a founder, is that you're on a sprint, but it's not sure a sprint, it's a marathon. You got to pace yourself a little bit, but you need the passion to be able to get up and continue at it for so long and all the trials and tribulations and challenges that are thrown at you.

00:22:07 (Rory)

Do you have much of a….  I was having this talk the other day, just sort of… what time commitment? Or just sort of like, what are you trying to promise yourself in your head? Like, right, do this for ten years? Or just sort of how do you think about what's next? Or have you got any kind of equivalent kind of finish line? Or sort of how are you thinking about that? This is something I think about a lot.

00:22:31 (Alastair)

Yes. That is a very hard question that I ask myself often, and probably my girlfriend asks me even more often to know when that's going to be. I think sometimes it's quite difficult to take a step back. And as a CEO and a founder, you do need to take a step back and you need to go, what's the plan here? Not just what's the day to day, week to week, month to month, looking like to improve metrics, to bring on new clients, to grow the business, to build technology, whatever it might be, you need to take a step back and go, what's the wider plan? But sometimes you can get too caught up in the day to day operational parts of the business rather than the strategic parts of the business. So, yeah, Luke and I, Luke's my co-founder, we take ourselves, we retreat from the business. I mean, we go on an annual ski trip, right. Which is all work. Obviously, him and I were physically away, and that's where we do our best thinking. So we're also keen skiers. He's actually a qualified ski instructor. So we do that and take ourselves to a chalet in the alps for a week. And I'd like to say we do a lot of strategic thinking, but we obviously do a lot of strategic thinking in the Folie Douce and on the slopes. Right. I think our best conversations are on the chairlift or skiing down together. But at those points, we reflect on, well, one, what we've achieved and two, where we're trying to go and what we're trying to achieve. I think you always want more resources to get there, so you've got to do with what you have, because we're also bootstrapped as well. Yeah, but let me get back to the questions on Trust Keith. So one of the things you mentioned was all you can eat, is that part of your. Because you obviously referenced kind of other business models, is that part of your model all you can eat data protection officer as well?

00:24:32 (Rory)

In terms of unlimited support? Yeah, that is because support, I mean, it comes from anywhere. It's whether it's a last minute questionnaire that comes in that they don't know how to respond to or product about to push something live, and they just want to double check some of the new processing activities they're planning to do as part of it, or they've got a deletion request or something just a bit awkward that they're like, oh, need to get some support on this. But I think that the way of solving for as unlimited just one, it definitely supports a stronger sales conversation because you're not itemising it like an agency or anything like that, which definitely helps as well.

00:25:17 (Alastair)

When you started it, did you have a fear of maybe you've had experience before with CharlieHR in terms of how it worked, but were you fearful that actually people are going to take the piss here and actually we're pricing and slicing an individual's time up in the month based on this. This is our kind of pricing model. This is how we've built it and modelled that scenario. But actually people are taking way more time than we expected, and they're kind of way over what we would expect them to have.

00:25:51 (Rory)

I think there's always going to be customers who like that. I think traditionally it's always the ones who are paying the least, who are the most active. But there's ways you can kind of naturally throttle that with service level agreements for how you respond to those and things like that. That actually it's not as much of an issue as you think it could be, but it's also its laws of averages. Some companies will be pretty active and some won't be. And actually the way our product is developing it will get to a point where actually the majority of the value is coming from the product and that they rely on their Keith expert. Yeah, I think it can be quite scalable.

00:26:33 (Alastair)

Yeah, I find it really interesting in this kind of all you can eat model. I see it more and more. I see it in design as well. Fascinating model as to how it will.

00:26:44 (Rory)

But it's interesting coming back to the constraints. If you look at businesses like all you can eat design, it's quite different, difficult business to scale because the scope is so wide. If your design is like, well, 1 minute it's a LinkedIn ad, the next it's an asset for the website, the next it's a marketing one pager. It's sort of, unless you can processise that, which you probably can, there's just so much variance that probably requires, I'd imagine, a higher caliber of designers. It's a much harder thing to scale, whereas something like what we're doing, we've literally got better and better at saying this is exactly what we do and this is what we don't do, which enables the support to be a lot more focused and more efficient as well. And that's again why I moved away from the unlimited legal support or whatever niche that would have been. Because again, it's like the scope is quite wide, whereas with data regulation, it's okay, well, here are the ten regs that you care about. Here's what that looks like for each of them. And we can operate in that known field.

00:27:43 (Alastair)

So you have also got some technology. Yeah, and I want to pick up on that. So is it technology complemented by a person, or is that a person complemented by technology?

00:27:53 (Rory)

It's a great question. We were having this conversation in strategy the other day. I think on day one, if you'd ask me, it was expert first, backed up by software. But the future is likely more product led, backed up by expert. But I think that the role of our experts are so key in driving a relationship with the customer, providing value where we're still scoping out exactly what we do and don't do for customers because it can be quite wide and there's just a lot of grey areas that we're trying to pick our own path of. Yeah, we will do that. We won't do that in whatever future it looks like the expert will be such a cornerstone part of it, because it's also how we differentiate in the marketplace, by giving, very proactively giving customers access to an expert who can handheld them. That's what they love. Yeah, I forgot what was the other part.

00:28:43 (Alastair)

Is it technology complemented by people, or is it people complemented by technology? That was the crux of the question.

00:28:53 (Rory)

So I think we'll see an evolution on that.

00:28:55 (Alastair)

But more and more, it'll tip to the side of technology.

00:28:58 (Rory)

It's one of these things that, and this comes back to that kind of bootstrapped and minimum viable solution concept is we have used our experts to facilitate product type experience that in time we will truly productise and the expert won't need to be involved in that. For example, our onboarding process at the moment, very manual, and the expert does a lot of that. We'll productise all of that. The customer will get probably get an even better experience and will be so much more efficient and scalable to operate well.

00:29:26 (Alastair)

A more consistent brand experience as well.

00:29:28 (Rory)


00:29:28 (Alastair)


00:29:29 (Rory)

And it's kind of actually the minimum viable product kind of phases that we went through worked really well because of this business model of expert plus software, because we could get the experts to a lot more of a doing and perceived value on day one and then slowly get product to dirt. Because on day one we were delivering deliverables in G drive and it kind of worked. We validated. It's like, okay, well, it doesn't look great because the customer can see, it's a Google sheet, but we validated that. That's how we can do it. And by the time we've built it in product and it's got our branding on it, that's going to cement that.

00:30:03 (Alastair)

Yeah. If you'd have gone, let's build a product first, you would have had still a bunch of experts, right? You'd have built something, you'd have spent a load of money and you wouldn't have had paying customers on day one. Right? I'm assuming. And you'd have spent a long time or a time building this product. Whereas the route you went down, you said, well, let's sell straight away and let's harvest what we're selling and productise it in technology and do it either at the same time or shortly thereafter. Is that right?

00:30:39 (Rory)

I think you just have to be really patient. I think you can convince yourself that you know exactly what you need to build for customers. You need to hurry up and build it, then they'll buy it. But I think that's so rarely the case unless you're doing a very cookie cutter. Here's this one existing tool. I'm literally going to copy and paste it and then run with it. That product experience, I think, is just so. You just don't know until you've got it in customers hands and you can't. I would expect to. And if I did it again with much more, maybe budget wise or whatever product first, I'd probably only be solving to build maybe a third of what I had conviction on from a product roadmap perspective, and then iterate and pull it all from the customer from then. I think what you see quite a lot in early-stage businesses, they sort of convince themselves they just build this next feature, or actually, let's not launch it yet. We just need three more months, three more months or whatever it is, and they launch this fully functioning app, but no one's using it because it's…

00:31:33 (Alastair)

Not liistened to the customer listen to. So while you've had the DPOs actually selling, having conversations, you're continually getting feedback of what should be in a product, or rather actually what should be in a service, which you can then productise and build into a product build.

00:31:47 (Rory)

Yeah. And it's absolutely that last bit, what should be in this? Because the interesting thing with regulation in particular is it's quite a broad topic segment, as I spoke about, which means most customers are looking for more of a solution sell. It's less of a, well, I need this bookkeeping tool or something very specific. It's a wider, I have this big problem. Can you solve it for me? And it's that solution based selling that works naturally to combine expert with solution… with product sorry. As you start finessing that into primarily a product led motion.

00:32:16 (Alastair)

How have you… because I think it's an interesting story as to how you've actually built the technology and you've done it in increments. So I'd quite like to touch on that. So you mentioned G drive was kind of your first, let's inverse comments, say your first build of technology, but then you stepped up and used low code or no code, and then you stepped up again. So can we talk through that journey a little bit in terms of how long it was between kind of periods of kind of delivering those different solutions?

00:32:49 (Rory)

There's how we delivered it, but it's also what we were delivering and the whole model of how do we solve for compliance, that's been the biggest shift. And to me that's the biggest sort of IP evolution of like, that's our approach. Okay, now we can really consolidate the product behind it. So on day one, we kind of looked at compliance and said, actually it's probably a year in by the time we said right, if we had to break this down into, what are the moving parts for compliance? There's policies, procedures, training and some tools. Those, all the moving parts. And then it says, well, to meet GDPR and to meet some of these other tangential outcomes, what are all these different things you need to meet? Right? And we bucket it into seven pillars, seven modules, access control, change control, data, subject rights, governance. And for each of them, they had their own set policies, procedures and tools, or frameworks, as we called them. So we basically itemised this whole, here are the sort of whatever 30 moving parts that companies need. And then it was like, well, how are we going to deliver? Well, let's start day one, MVP, let's do these on G drive and deliver them in G suite, essentially. And then some of them we started, I guess, productising since then, like our e-training and things like that. And then more recently we've reviewed that again. And I think this is just a natural evolution, which I don't think products ever finished, where we at one point were offering customers ISO 27, 2001. And we got to a point and said, actually, we can't be the best at ISO and data regulation compliance. And then looking at the market, there's some fantastic vendors out there. We don't need to go head for ever on everything. Let's focus down and that's when we then looked at that productising the DPO role and productizing the data regulatory niche and going really, really deep on that. And that's how we then refactored, okay, what are the moving parts of that? And that's more recently, beginning of the year, end of last year, we've now started taking more of a risk-based approach. We've actually finessed it down to say there's 48 controls with associated risk, 48 controls which individually have moving parts which align to policies or tooling. That now means you meet the regulatory compliance. And that by productizing that now we're just in a much better place. We've got much better conviction. And actually the user experience now is going to be so much better because of that continual refinement as opposed to saying, well, on day one, it's seven pillars, seven modules, let's just productise that. We've kind of continually revisited what's the customer actually need? Is that the best way of doing it? What about this? If we thought about that, okay, let's keep focused. And that's why we've probably been on G drive definitely a lot longer than I thought we would, but it's enabled us to very nimbly iterate what we do and how we do it until we had the conviction of this is how we're going to do it.

00:35:30 (Alastair)

Because if you'd built some technology from scratch for your original thesis, one, you'd be less agile to shift and maybe even less reluctant, more reluctant to shift away from that as well because of the time, effort and energy that's gone into it, be a much bigger decision to can it or shift that direction and what's it built in. So you were on G drive for quite a period of time, and now?

00:35:55 (Rory)

We're building it out on bubble, which is the no code app. And the reasons behind that are we're still building conviction with our roadmap. So it's quite a nimble, fast moving place. And there's also, like budgetary constraints. We're not in a place yet where we can go and bring on board two or three kind of technical hires, which our working assumption is we'd need that kind of resource to go and build it all custom, and it's also the speed. So I think these next six months are likely going to be in that environment, which from a customer experience perspective, you'd have no idea. It's only from the technical, like, what's happening under the hood. But it's likely that in the future we will revisit that. And we may or may not go and build custom code, but it's also, I mean, you look at back in the day with websites, they all used to be build custom, and that's kind of what people were looking for. Then you've had Shopify, Webflow, Squarespace, all those. And it's like at some point particularly investors have started looking at and be like, oh, that's not a risk anymore. That's actually really standard. And I think there will be probably a slur, but an equivalent thinking with product as well. And it's actually what's more important, that we own the code and it's all custom or that we've sold solution itself. The solution is working and customers are paying us money and staying.

00:37:10 (Alastair)

So it's a really interesting point, challenge, isn't it? Because as you say, Shopify, tens of thousands of e commerce businesses are powered by Shopify, and they all look unique or relative. I mean, you go to a shopping cart and you see it's a Shopify. Well, you can tell it's Shopify website, but they have their own brand on there and it's very much their brand. And that's what e commerce businesses are built on. A know more than anything. So you are a bootstrapped business and you're a non-technical co-founder. And I say non-technical in the sense of a non-regulatory DPO technical founder, and also no code, I think, as well, or thereabouts. So can you, let's split those both up a second. So you're bootstrapped. Tell me how you managed to fund this, because I think it's really interesting to talk about the other options than just equity backing. Right. For people to be aware of how you can actually bootstrap a business. And as a non-technical founder, because a lot of people go, I bootstrapped a business, but I wrote the code myself, or I'm a deep technical expert in the subject that we're selling. So maybe we can, if you're happy to share, talk about how you actually managed to get the business off the ground and fund it.

00:38:29 (Rory)

So I started researching it in probably August of 2019, and I then went down to a four day work week. So I was very intentional with the time I was putting into it. I'd already had some existing kind of founder connections, friends who I was talking to, and I was involving in the customer research phase, in particular James and the team at GoSquared. So I kind of ideated a point where I was like, right, I've got one page. I kind of feel like this is what we're going to do. And then I thought, well, gosh, I'm not an expert. Need to find me a privacy expert. And I very, I don't know what the word is, but kind of serendipitously got introduced to a consultant called David Clark. And the business would not have got started without him at that time in particular because he was very willing to take the work as and when it came, and he was willing to kind of jump on sales calls with me, provide that legitimacy and also technical support. So I managed to convince him that, okay, I'm going to sign a customer. They'll pay £300 a month, the current world viewers, that includes 3 or 4 hours of support a month. I'll pay you for that 4 hours of work every single month. From his perspective, it's like, well, it's recurring money. Every time we sign new customer, that's going to start stacking up. But the beauty of very helpful with him, he said, okay, well, I'll help you a little bit out and about with that thing, but he's got that fixed thing. I didn't have to hire him in house. I wasn't paying sort of £7k a month on day one or anything like that. So that was really, really helpful. But there's other ways of doing that, whether that's freelancers, equivalent consultants, that one can do that. So that meant our burn rate was scaling with customer revenue..

00:40:11 (Alastair)

Wasn't going in those steps where you needed the capacity in advance and as you say, wasted capacity, because it's just not being sold until that point.

00:40:21 (Rory)

I finished work with Charlie kind of at the end of mid-October, whatever it was. Then we signed our first customer in December. They started paying in January. By about March we had our first three customers and that's when we started doing maybe three and a half MRR. And it was really at that point where I had a massive sigh of relief and I thought, okay, what's now ramen profit? But I know I can afford to put all my time into this.

00:40:45 (Alastair)

And was it only a subscription model at that point? There were no one offs just to take some.

00:40:48 (Rory)

Well, this is the beauty of those commercial constraints. It was like twelve-month minimum commitment and then a rolling three month notice period. And by locking them in it was like certainty. But then I also said, well, let's get them to pay monthly because I don't want to get ahead of myself on cash flow. And also if for whatever reason we close down, six months in, I haven't taken them for the final six months. So that was the kind of thing like that. But the other thing that helped was the one-time setup fees. And those ranged massively from sort of 3k up to sort of £25k and those gave us the opportunity to then overinvest, waiting for the MRI to catch up. And that is basically how the business has been built, is the revenue will get a certain point, we'll then make an investment in more team or other things. The fixed costs will jump to here, but there's retained profit in the bank or wait for that to catch back up. And it's just that constant thing like that, which is why we've basically been in break even for the lifetime of the business.

00:41:44 (Alastair)

So it's a novel concept, isn't it? To have some revenue and make some money and bring some cash in on near enough day one to actually fund the business rather than someone else fund it. So what about the nontechnical aspect of it? Obviously you had support on day one in terms of doing that, but do you ever feel now your depth isn't the right word? I don't mean it like isn't the right phrase something like that. But do you ever feel maybe exposed because you're in such a regulated industry or you're working in such a regulated industry that people want or expect you to be an expert in that area as well?

00:42:32 (Rory)

Depends what the environment is. I'm not a regulatory expert, but I think I've got quite competent at understanding what the problem is and how customers perceive and want to solve that problem. And I think that's the hardest. It's a different skill to kind of get to proficiency with which it just takes time, really. But I think that gives me confidence for some of the decisions that we're making. But also we're not selling to compliance managers. I think this is a really interesting thing, is we're not setting up booths at all these security cons or whatever it is. That's not our market. We're selling to operators who have a very similar worldview to me of what does good look like. They tange you understand what are you doing and what's happening. So for me to have to understand a slightly more layman view of this is what needs to happen, they can understand that, and then everything else happens under the afterwards.

00:43:29 (Alastair)

Yhey're able to relate to you when you talk to… I don't know if you sell or not, but I'm sure you have conversations with your buyers who I'm assuming are founders, CEOs or COOs and they are able to have sensible conversations with you, super technical ones, where they walk away going, I have no fucking idea.

00:43:44 (Rory)

Because on day one, some of the consultancy work we'd get from David was legit, but it was incredibly complex. So I was kind of putting this wrapper on it of like, okay, let me just reformat that G sheet. We don't need that row. Let's get that rid of that row. Let's put that on another tab. Let's make this look a lot more digestible, and we'll put it in their brand colours. And I'm actually going to present it to them in this customer deck. Right. That feels really straightforward. It's broken down into principles. There's a clear agenda. They know what they're getting, everything like that. Just kind of put a much more operationalised that into a very digestible, understandable kind of film.

00:44:18 (Alastair)

Yeah. Talking the same language as your customers, really, isn't it?

00:44:21 (Rory)

Yeah, completely. And I think that's what a lot of people in that industry aren't great at, is they'll default to complexity. And I think this is quite often come up against consultants in the space who they almost hide behind complexity by maintaining and not sharing what's really happening. They convince the customer. Only them. Only I can solve that problem. No, I can't tell you about that. Or, like, don't you worry about that. I've got. It's too technical for you to do because they risk the customer becoming self-sufficient or they just become less reliant on.

00:44:53 (Alastair)

Yeah, I find that doesn't work. Ultimately, it doesn't work. If you look at the concept of storytelling, they are making themselves the hero in that this technical person that's talking technical jargon is making themselves look like the hero. And actually, in the story, they need to be the guide, and the founder needs to be the hero, because everybody wants to be a hero. So if you're buying, you want to be the hero and you want a guide to help you through it rather than another hero. It happens in the world of finance as well as you can imagine, and taxes. So what would you say have been the biggest challenges and stumbling blocks as you've set up Trust Keith with no equity backing and going in a regulated, complex world and hiring people as initially a people first service, and maybe it'll switch to a technology first service. But certainly hiring people has its challenges. But if you were to reflect back, what would be the biggest challenges of bootstrapping and growing the business? As a sole founder.

00:45:58 (Rory)

I think there's obviously resource constraints, but I think that can actually be a massive advantage because it forces you to be a lot more resourceful and drives you towards, albeit slower, but a more efficient route to product market fit, because anything you build, you had to be able to sell. And therefore, if you can sell it in advance right now, it's sensible to make that investment and then kind of build it out. So things like that. I think there's always this ying and yang between the customer experience and the product experience that if you suddenly sign those new customers, okay, that needs to be solved, then you need to keep up the revenue momentum. And it's taken a long time to kind of get both of those at the right kind of level or being consistent, I should say. So that's been really challenged, particularly with something like sales where lead gen, the meetings you're booking are the life butter sales. And if you have three or four weeks back-to-back of poor lead gen, that's going to knock you for a couple of months. So that's been challenging, but we've very much iterated to become a lot more focused, and we're very data driven and big shout out to our Head of Revenue, Mitch, who's a beast at all this kind of stuff, but we're just very specific of what our weekly inputs need to be. How many dials, how many contacts are we adding to get the results in our weighted pipeline where we need to be at each stage in the quarter and everything like that. That is now in a really good place. I think the hiring challenges, I mean, obviously hiring's challenging. I think I've just been very lucky. I think even like day one, our Head of Ops, Anya, that to me, was the day that the business truly professionalised when she came in, and she's helped drive a lot of those hiring decisions that have kind of got to where we are. But it's also because of the constraints and the speed we're moving at. We've had, in some cases, to take a bit more time to make decisions, which means when we come to hiring, by the time we've got the role live, we kind of know exactly what we're looking for. So we know what good looks like, and therefore our hiring success rate is a little bit better than that. We've not always been successful with it at all, but that's helped.

00:48:10 (Alastair)

What's your biggest tip around hiring?

00:48:12 (Rory)

I think telling a really structured and consistent hiring framework in terms of what you're. I mean, one of the things we do, it's more just a tactic as opposed to massive tip. But during the application process, there's three questions. It's, can you come to London for our monthly, great. Why this role? Why trust Keith? One sentence, no more. And it's so simple, but you can tell so much if they say no to come to the monthly meetings. We haven't read the whole job description because you need to do that right next. And then it's like, well, why the role? And you get so many generic ones, like, I need money or good opportunity or really generic stuff, that it's so easy to stand out, even just reference one of our values or something like that, and it's like, okay, read our website. So it's a little thing like that. Then separately, we implemented Traction, so the operating system made by Gino Wickman, and we implemented that really early doors that has a whole approach to how we review, how we hire, how we reward and manage the team internally against values, core competencies and everything like that. Which means when we get to the screening and all the interview process, we know exactly what good looks like and we can kind of score against that in a really consistent way.

00:49:30 (Alastair)

You just mentioned Traction. I think one of his other books is Rocket Fuel. Have you read Rocket Fuel? Because there's this concept of a visionary, and I can't remember what the other term.

00:49:41 (Rory)


00:49:41 (Alastair)

Sorry, integrator. That's it. I was going to ask you. So your sole founder, I'm sure you're the visionary in that business, do you have an integrator? Is that your COO that you mentioned?

00:49:55 (Rory)

I'd say historically I've been that integrator, but I think that's a role we need to kind of solve for going forward. And I think this is the reality of business. As you grow at each inflection point, whether it's three people, then eight people, then twelve people, whatever, that things break and you need to reset things, whether it's org structure, responsibilities, or accountabilities and things like that. So I think in the future, that's definitely a dedicated seat, but I think until then, there's a few of us who are sitting in it.

00:50:24 (Alastair)

So we started off the conversation around you had a couple of previous ventures and you were very methodical about the lessons you took from them to apply to Trust Keith. If you were to either go back and start Trust Keith now, or start another venture, what would be the very methodical lessons you take from Trust Keith and apply to your next venture?

00:50:49 (Rory)

I think a lot of that setting the constraints at the beginning is really important, I think, particularly personal constraints, your business you're setting up. Like, what personally do you want out of this? Do you want to work six days a week for five years? Or do you want a lifestyle business? Or what does success look like for you? Being really clear about that, I definitely have ideas about other businesses at some point, so that's probably more… maybe it's a business model evolution I didn't hear because there's kind of like ladders of what good business models are as they ratchet up. And I think one of the premium best type of revenue, I think, is some kind of like a marketplace model. Like a B2B marketplace. Whether you're a zapier or a tray or a stack one or something like that, where you're embedding integration, so you're incredibly sticky. You do the sell and you're basically done and they're in and they're going to scale and they're going to stay. There's something around that kind of model, or certainly product. I don't know how you can solve. There's many ways of probably solving for that, but that type of business model, I think is really hard to do, but something like that. And then also I quite like the idea of what seem like really boring businesses because everyone runs to direct to consumer and things like that, or other kind of mildly sexy B2Btools. But it's a lot of the boring businesses that I think it's easier to stand out and there's still a lot of competition, but it's kind of different. And that's something even with the naming of the business. I really tried playing into that. So Keith is actually a family guy reference, and it's what is the most unattractive male first name in the English language? Just playful with the idea that's the personification of someone who works in compliance or something boring and just kind of rifting on that.

00:52:44 (Alastair)

You mentioned Mitch, I think B2B sales and getting that right is quite a difficult thing to do to small medium sized businesses or startup scale ups. What lessons do you have or what's worked well there that now you've kind of nailed that secret sauce on doing it.

00:53:09 (Rory)

Particularly the headwinds are you don't have any limited brand awareness. So what we've really been focused on is having a really targeted, ideal customer profile, which is why we're very London centric, because the more focused that we are, the higher likelihood of word of mouth kind of trickling around is better. So we can get a real kind of penetration, just really focusing what those inputs are. We know how many meetings that we need a week or per month to get the deals that we need. So it's being really focused on where are we expecting this to come from and tracking those inputs, whether that's SDR work or network based intros or then some base assumptions for word of mouth and things like that. So it's very much like a system and machine mentality we have of this input is going to get that output. And then there's more tactical stuff more recently that we're constantly learning from, whether it's. If we have more than one stakeholder on a deal, our close rate is sort of 60% higher. Right. Well, let's make that a qualification criteria that we can't move into the next stage until we have two senior stakeholders involved in the conversation. There's things like that that we're iterating on, but the biggest theme is just consistency.

00:54:23 (Alastair)

Cool. No, it's good to know. I think it's something that businesses, early-stage businesses, struggle with because they don't really know who they're selling to, they don't really have an ICP, and they try a lot of things, and eventually…

00:54:35 (Rory)

There's never this magic or unicorn tactic that we haven't done it yet. We found it, now we're going to be on a gold rush. It's just these boring bits that you get consistent when they slowly stack up and they slowly compound. It's something like even like word of mouth. It's like, well, if you do good business and you're around for a long time, that slowly starts making up a meaningful amount of new revenue. But it doesn't happen overnight.

00:54:55 (Alastair)

No. And every new client you have just amplifies that word of mouth opportunity as well.

00:54:59 (Rory)


00:55:00 (Alastair)

One of my favourite topics, Rory, is metrics. It's one of the things we focus on at Flinder an awful lot. Financial and non-financial metrics, leading and lagging indicators. Tell me, what metrics are your favourite that you want to track? We've obviously just talked about sales. As an entrepreneur, you want to see the conversion, you want to see the new contracts. But tell me, what are your favourite metrics to track in the business?

00:55:24 (Rory)

So, I love a good metric as well. I think inside the business, things like employee net promoter score, I think are really important because that's a catch all for a lot of things in terms of remuneration, strategy learning and development progression, and just general line management stuff. So we hold that really close.

00:55:46 (Alastair)

And how often do you monitor that. Is that quarterly?

00:55:48 (Rory)

Quarterly, yeah. And then another one externally, I guess, just from like a business side of is net revenue retention. So the way I kind of view that metric is if we can get that as and when that is, whenever that's north of 100%, despite any churn, whatever, you just don't have a leaky bucket. You're matching up for it. So last year we had a really strong, I think it was like 117% net revenue retention. This year, the climate is not helping. So we have had more churn than we forecast, but our north star is. Anything above 100% is what good looks like. And if we can solve that, then all the sales and marketing efforts we're doing are just going to compound. So it's kind of that and gross margin are kind of like what I think makes a really healthy business.

00:56:30 (Alastair)

Yeah. And just to be clear, net revenue retention above 100% is effectively expansion revenue. You're selling more expensive plans or more services to your existing.

00:56:40 (Rory)

Yeah. Or their headcount expands. They pay more. Yeah.

00:56:43 (Alastair)

Okay. So you're on a per seat head.

00:56:46 (Rory)

So there's a metric based on the size of the business they pay and if they're in a banding. Yeah, exactly.

00:56:51 (Alastair)

Okay, great. Okay, so you've got organic growth without actually having to do too much as the startup scale up, which typically will grow. So you have that organic growth as well. That's great. What one piece of advice would you give to other founders? Obviously, we've talked about the bootstrapping journey here, not taking any external equity and being more in control of kind of the future and the destiny. You've had a couple of other ventures. What would be your one piece of advice for founders?

00:57:24 (Rory)

I think my one theme would be just don't rush to go and raise money. I think it's so glorified as a sign of success when it's not. You've just taken on a ton of accountability. And unless you've got product market fit or you've got traction, you know where you're going to put that money. You've got a deadline now to make it work. So not gravitating that on day one, which not everyone can do, but I would challenge that because it's a constraint, whether it's whatever it is to solve, to get that first customer signed and not getting carried away with your product before you've made the first sale. I definitely believe that it's marketing that wins, not product. And you can sign your first customer off the back of a compelling one pager of what it's going to do and you can pretend it's live. That's all you need. And then once they've signed, then you can figure it out.

00:58:12 (Alastair)

It's great advice. Thanks very much, Rory, for joining us on the pod today.

00:58:15 (Rory)

No worries. Thank you.

00:58:16 (Alastair)

Thank you.