David McDowell: [00:00:00] The entrepreneurial journey is just staying in the game long enough so that you can get the wins.

You're gonna make mistakes all over the place and it often feels like everything that you do is a mistake. 

David McDowell: I was living and working with Don, we shared an apartment, we shared an office.

We were trying to take college students and get them to go into your home to teach you how to use your computer.

And we started the business on an absolute shoestring budget. 

David McDowell: When you take over the CEO role, you are also in charge of all the business development.

Suddenly you're the external face of the organisation instead of the internal face, and you are able to bring people along on your journey.

Landing our first sports book with Genting Casinos in the UK, we convinced them that we could build a sports book and get it live, and we did. 

​David McDowell: The work I'm doing over at LBS right now, mentoring startups and some of their incubated companies.

It's great to be able to talk to some young folks who've got a ton of energy to keep that journey as close to their vision as possible, not to be distracted. 

Don't make it harder than it has to be, all [00:01:00] the overthinking that you've got some strategy or strategic roadmap that you've gotta unlock. When actually it's usually right in front of your face. 

David McDowell: You know, when you've got a vision and you're trying to implement it and you truly believe in that vision, you can work really long hard hours and as long as you're taking care of yourself,

I think you can go for a long time. There's a lot of oxygen in the room.

It's later when you get into everyone else telling you how to do your job, it becomes a lot more difficult to deal with.

​

David McDowell: Because of capital, because of external influences, be it a regulator or a customer, or just a scalability issue, your lens constantly changes on what's important and all of those are almost noise to the vision.

You still have to kind of make sure that you're building your own vision and not just taking care of these other things.

But you know, how do you juggle urgency versus important? 

​David McDowell: In 2020 we were platform of the year from SBC, one of the most prestigious, categories in those awards.

That was absolutely fantastic.

But you need to, you need to scale up, to keep that momentum. You can't put brakes on the whole development team and just focus on sales [00:02:00] and think that you can catch up.

So, for me personally, a hugely frustrating to end because I felt like we got the company to be a real challenger brand, and then we didn't make the most of it.

Leo: Welcome to the iGaming Leader Podcast, where we uncover the human side of some of the most inspirational leaders in our industry. I'm your host, Leo Judkins, and as an ex iGaming director term performance coach, I've worked with over 200 leaders from companies like Entain 3, 6, 5, flutter, and many more to help them build the habits.

To achieve sustainable high performance.  In these episodes, we share exactly what it takes for you to achieve the same. So with that being said, let's dive in.

​Leo: Hey everybody. Welcome to the iGaming Leader podcast. Today I'm joined by a guest who has spent 25 years building B2B platforms in gaming, pioneered player proposition betting, co-founded GaN, which later went public. Then 15 years [00:03:00] as CEO for SFSB, scaling, 30 to 40 brands before a private equity exit and sales to every matrix. Raised many different funding rounds, survived regulatory crisis, and navigated three startups through, really difficult moments. now entrepreneur, mentor, in residence for the London Business School. But the most interesting part, I think David, is not what's on your LinkedIn. It's building 25 years in this industry actually, uh, looks like.

So, David McDowell Welcome to the podcast

David McDowell: Thank you very much.

Fantastic intro and I think it really just, uh, sort of summarises 30. Years, you know, 25, 30 years of beating my head against the wall 

Leo: I've been so excited to talk to you. I, I, I really wanted to, kind of start with your early beginnings of, where you started all those years ago, which is like before everything, right before the internet, really helping out people, know, even use browsers, use emails.

Can you tell me a little bit more about that beginning and what it felt like to build something that wasn't even there yet?

David McDowell: the First entrepreneurial venture that you're referring to was right out of business [00:04:00] school. So I went to business school in 93 to 95 and set up a business called SOS. So Student Onsite Solutions. Uh, immediately afterwards with a, a colleague of mine, Don Matthews. It was actually his idea, and I worked on it with him as a new venture development class.

And he said, let's start it. he was in Toronto, and I'm from Michigan, so it was right next door and very early days. So in 1995, we were taking students and sending them into your home to teach, adults how to use a browser, how to set up an email. I look back on it very fondly, it was basically all in, I was, living and working with Don.

so we shared an apartment, we shared an office, And, you know, today, I guess you'd describe it as a two-sided marketplace. Back then, we were trying to take college students and get them to go into your home to teach you how to use your computer.

And you know, now you'd look at it, you've got two sides of that marketplace. You've got the labour of the students and you've got the customers. How do you find the customers? And we started the business, I think on [00:05:00] something like $35,000 that Don and I both put in personally. It was, uh, on an absolute shoestring budget.

but I've gotta say I got a LinkedIn request. Literally yesterday from one of our, we call them consultants that would send him around. And the kid was in high school when he was doing it, and he was our best consultant. so that meant he probably got about five hours a week that we could, that we could get jobs for him.

'cause we didn't have any marketing budget. We were going on the radio to try and drum up, some business. And, he looked back on that really fondly. It wasn't the lack of hours, he was the only kid in high school that had a pager, which was, uh, you know, kinda set him apart from the crowd.

Leo: Kind of that historic view of the internet as well. Most people don't even you know, they don't remember, probably weren't even there. So, you know, what I love about you is that that's kind of started your entire entrepreneurial spirit.

You've been through, I think three startups in 25 years, and, uh, you've had exits built platforms, raised a lot of money. But reflecting on all of that, what's, what's the [00:06:00] the thing that's made you most proud in that journey?

David McDowell: there are single moments in time that you can look back and think that was kind of a peak of, positive emotion. there are some things that come to mind Going from the first two startups that I did, I was sort of CFO, COO, so very much hands-on, very much inside looking.

And as I went to FSB, it was the first time I was actually in the CEO role. And I think for both of those, because of the finance and the operations, being a founder, I was always involved in a lot of the financing and fundraising. But when you take over the CEO role, you are also in charge of all the business development.

And so I think, you know, one of the proudest moments was, was really landing some of our first big deals. I think, you know, when you go out and suddenly you're the external face of the organisation instead of the internal face, and you are able to bring people along on your journey and get people not only to sell, I mean, equity is [00:07:00] close, is selling, right?

When you sound like. but getting a customer to take your product, especially a B2B platform, where it needs to have a certain amount of, uh, I guess, table stakes to be a competent product that you can get into the marketplace. And landing our first sports book it was originally with, um, Genting casinos in the UK and they had an online site and, we convinced them that we could build a sports book and get it live.

And we did,

Leo: how did you find that in kind of those transitions as well, from the more financial side and, raising money to operationally leading the teams, did you find that hard to make those transitions?

David McDowell: I'm not sure that I did find it, if, you know what I mean? It was, it was a constant evolution. Every day was a different challenge. when you're in it, you don't always step out of it to take look or you take a look back to take stock of where you're at. I sometimes the entrepreneurial journey is, just staying in the game long enough so that you can get the wins.

You know, you're gonna make mistakes [00:08:00] all over the place and, it often feels like everything that you do is a mistake because almost nothing that you do is optimised. There's always something. You, you're, you're, you know, you're trying to go at a goal, but you've gotta go take this customer over here.

It's not quite the right customer, but you justify it because it'll get you a little bit further along. It'll drive some revenues, it'll build your reputation. And, you know, you think there's a straight path from point A to point B, but it's all over the place. ties into The work I'm doing over at LBS right now, you know, mentoring, you know, startups and, and some of their incubated, companies.

It's great to be able to talk to some young folks who've got a ton of energy and to just help them keep that journey as close to their vision as possible. Not to be distracted, prioritising the work. And, you know, it's, you just don't make it harder than it has to be. It's actually all the overthinking thinking that you've got some. strategy or strategic roadmap that you've gotta unlock when [00:09:00] actually it's, it's usually right in front of your face. This is the opportunity. This is what we need to do to build it. Focus on the things that are important, actually getting from point A to point B, and don't get distracted by a customer saying, oh, if you just give me this, then, then I'll take it.

Because you give that and then they don't take the product because it was just an easy way for them to say, you know, say yes instead of no.

Leo: That is so difficult, though, isn't it? Because you are always faced with significant challenges, right? And also always faced with significant opportunities, but both of those can massively sidetrack you and lead you away from that thing that's right in front of you, like you've just said. I think also the other thing is that sometimes just zooming out it's just not possible because it's this constant, like you're constantly racing, right? You're going from one fix to the next, from one opportunity to the other. How did you manage that throughout the years without going absolutely crazy or burning out?

David McDowell: I've always been pretty good at compartmentalising, so if I need to switch off, I've always been [00:10:00] pretty good at switching off. And frankly, I've always been a good sleeper, and I think these days you hear so much about how important sleep is. unknowingly just by making, you know, by being a good sleeper, it's a foundation of health, you know, I never purposely paid attention to my health, but I think some things like that really helped avoid some of the burnout. And I think these days people are so much more aware of, putting your health first and making sure that you're taking care of yourself physically and mentally.

I think once you become sort of a founder, a CEO, and I, if you go back to that first one so I came back to London in 1998 and did a couple of years as a management consultant, and you're, you know, you're working sometimes, you know, 80 hours a week. And it wasn't the hours, it was the lack of investment, like the lack of being truly invested in the product.

And I found, that much harder because it wasn't my idea, it wasn't my passion, it wasn't my equity. whereas actually, you know, when you've got a vision and you're trying to [00:11:00] implement it and you truly believe in that vision, you can work really long, hard hours and, and as long as you're taking care of yourself, I think you can go for a long time.

it was really only sort of at the end, if you start having. challenges with your board if you have investors where you don't see eye to eye on the future of the company, those are the points that cause the real stress.

So I think the early days as a founder, when you are raising the equity, when you're putting in those hard shifts and you're building a product, it's actually, there's a lot of oxygen in the room and there's a lot of energy that comes from it. it's later when you get into everyone else telling you how to do your job, I think that's when it, it, becomes a lot more difficult to deal with.

Leo: Yeah, I think that's so true. It's never the hours, it's the weight of those hours. Right. And sometimes that weight gets really heavy. So that brings me to something else, which is boards and advisory and, and support from outside. So how have you dealt with that, David, as you, as you've grown through your journey and, also what you see now in your current [00:12:00] role? What's the value of that? Like outside perspective, not having to do everything by yourself, having some sort of sounding board. How important is that in a founder's journey?

David McDowell: Surrounding yourself with talent is incredibly important. And I think that is, um, both operationally with your management team and surrounding yourself with a strong board. I've always believed in that. I think that, it's good governance, right?

Over the years, I can look at all the companies and I don't wanna start naming names or, you know, but we've had good directors and we've had bad directors. And I think that there are a lot of examples, especially when you're starting a small company and you have individual shareholders who are.

asked to join the board because they've put in a large chunk of money, they've demanded it. Or even if you're trying to, you know, trying to build a board with skill sets that you don't have internally, and you look at your shareholder base and you [00:13:00] try to get someone to come on and step up as a board member.

I think that non-executive directors have a real problem separating their desires as a shareholder from their role as a director. And, I've seen significant damage done to organisations because non-executive directors are incapable of acting with, you know, the best interest of the organisation, first.

I think that's a real frustration of mine and I think that is, it's understandable how. I think people put themselves first. I just don't think there's any place for it. And then when you have somebody who's a board director and you start over, time realising, their decision-making capability is, somehow, affected.

It's very difficult to make changes. you know. But likewise, you know, our lead investor from really from the beginning was Mark Blandford over at FSB, [00:14:00] and the tone that he set at the board meetings were, let's not spend a lot of time congratulating ourselves for what we did.

Right. Let's talk about, you know, the challenges that we've got. Let's talk about how we can improve the business and be efficient with the time. It was fantastic. brought on Susan Ball as well, who was over at Cambi and, and, and at Play Tech. And together I found both of them were fantastic at being able to just drill down, challenge you on the issues, ask tough questions and that's what you want of a board.

Leo: over the 25 years you've dealt with different board members, different board, dynamics, and of course there's gonna be toxicity there, there's also gonna be real like drive and energy or oxygen in the room, like you said.

what have you learned about dealing with different types of people that perhaps have different types of interests? Like you said, short term shareholder, about whatever that is. So what, what are some of the things that you've learned from that, that perhaps people listening could go, okay, I've got this really difficult person here, or I've got this really [00:15:00] helpful person here, This is how I can deal with it.

David McDowell: I've seen some, um. some interesting things and I'll, you know, I'll, I'll go back to an example of something outside the industry. In my first business, one of the board directors forged the CEO's signature on documents. and they felt that they had a right to do that because they had invested significant capital into the business and they were gonna get their way.

And there are things like that, that happen that you would categorise as wrong and you, and, but the only remedy is to go to court. What other, what other remedy do you have? And if you don't have the same financial firepower as your investors, you're not gonna go to court. And I think, I think that's a challenge.

I, I am, yeah. I guess over the 30 years, and it's not just the companies I've been in, it's the stories I've heard, There's a lot of shenanigans that go on at the board level. there's another company I'm talking to that, you know, they went public and had to go into administration [00:16:00] because one of the investors was going onto chat boards as four or five different personas and, and like pumping and dumping the stock.

you know, I think it's that kind of distraction that a founder CEO can do without. you choose your board members carefully, choose your investors carefully. it's a lot easier said than done because when you're out there trying to raise money, you're knocking a lot of doors and you're just hoping for a yes and somebody you know.

And, you know, I never, You know, kind of understood why people would say, careful who your investors are. 'cause I thought they'd make the investment. They write the check and you can run the business. That's the farthest thing from the truth.

You know, I think, I'm really pleased with what I was able to do for many years at FSB because I was able to raise money from a wide group of investors, able to, you know, prevent any kind of one, uh, group building up power at the board. We had a very good dynamic, and that worked for many years.

And as soon as that dynamic changed, all of a sudden the board was telling us what [00:17:00] to do operationally. And, you know, and without the expertise, without the knowledge of actually what you're doing day to day, it, it messes up companies.

Leo: Very true. And, and we've all seen these horror stories, right? So let's put ourselves in the shoes of, you know, a business that's desperate for money. Running out of runway, needs that investment and, finally gets a yes. Like, what do you do in a position like that where you really need to do your due diligence on, finding the right investment because we are built to prefer short term benefits over long term, over long-term solutions.

The, actually, the entire industry is built on that. So how do you prevent that, You know, when you really need that money to survive?

David McDowell: don't put yourself in the position in the first place. You know, the other night I had, sort of young entrepreneur asking me the question, he's got some traction, and should he be focusing his efforts on scaling out the business and, and driving revenue growth?

Or should he be putting his effort into building new features for his customers and getting that customer feedback [00:18:00] up? And it was an it was a great question. but you can't answer things like that in, you know, externally. Like, I can't tell him 'cause I don't know his product, but I also don't have his runway because again, you're not just making decisions that are the right thing to do for the operations of the business.

You're making those decisions in the context of how much capital you've got. You know, I always wanted to build a competitive sports betting platform, but early days, I knew that we had to build something of a more minimum viable product. We started with some, real time fantasy football ratings for players.

And at one point we needed to get a gaming licence, a pools betting licence so that we could start running some of these products ourselves. And, you know, it was gonna take a significant amount of our leftover capital, you know, you've gotta make some of those decisions where your burn rate's going to double.

As soon as you make a decision, your runway gets cut in half, and you're immediately into the [00:19:00] cycle of fundraising. And, we'd go, you know, maybe nine to 12 months between fundraisers. You just can't, you've gotta, you've gotta find a way to break that cycle of, I'm working on the product, I'm selling the product, now we're delivering the product, and then I'm raising more equity.

And, you know, you get into this cycle where a little bit more equity allows us to add some more features, add some more sales, and get to the next milestone. And, I don't think there's any right answer. If you raise too much capital, you delegate yourself too much. But if you don't raise enough capital, then it's a really long, slow grind.

And I think actually entrepreneurs today are in a fantastic position, certainly in the gaming industry. Now there's capital available if you go to America. Whereas, you know, pre-2018, it wasn't available at all. you've also got, tools where one person, really understands the product that they wanna put out.

Can use AI tools and mock things up, get a minimum viable product to market and [00:20:00] show traction, and get that share price up before they need to raise capital. And so I think it's just this juggling act of how much capital do we have, how much can we raise, the Goldilocks, you know, don't raise too little, don't raise too much.

How do you get it just right? And you know, again, back to what I was saying earlier, it feels like everything's a mistake 'cause you can't get it just right. So you've gotta err in the side one way or another. And it almost, the entrepreneurial, I guess the mentality is always feeling like you're making a mistake whenever what you're doing is solving the problem, getting capital into the business and moving forward so you can fight another day.

And you know, if you believe in the product and you believe in the vision, then you take the money and you work it out or if you aren't really convinced on the product and the vision, and maybe you're not raising money because the product's not there. Maybe you listen to the market and you decide that you're gonna stop this thing.

Maybe, maybe, come back to it later. Maybe pivot in some way.

Leo: I love how you started that out as well, starting [00:21:00] propositions and having this big vision, but starting with one, feature, one aspect of that bigger vision, and then slowly getting closer and closer to, to that eventual vision.

How long did it take you to get there, and did you ever even feel that you actually got to that end vision?

David McDowell: We ever get to the end vision? No, not really. We got close, but then you keep on building more and more things on. Right? The vision keeps on expanding if you start with a minimum viable product. you know, we started off, I wanted to build a modern sports betting platform. If you go back to 2007, open Bet was really kind of the platform, that was driving all the big, all the big sports betting operators.

the iPhone was coming into the market, completely changing the consumer experience. And, um, live betting was really just starting to happen. you know, we could see that data coming from the stadiums was not collected. I mean, you still had, I think, sport radar sending people entrenched coats to tennis matches back at the time selling scouting services.

Right. But I believe [00:22:00] that live data coming from the stadium would be covered. Faster, more detailed, more reliable as it becomes legitimate. And that if you were to build a modern sports betting platform, it should be driven by those data feeds.

So our minimum viable products that we started with those fantasy products allowed us to use some of the fastest real-time data feeds in the market. They were from orbit at the time. We were using TX odds to scan the Asian markets so we could understand goals and then we could tie, we ran our own models to figure, you know, translate goals into fantasy points for players assists and goals and, you know, you know, those types of things.

and so what I looked at for the MVP was how can we get a build a product that we can take to market while also building technical competencies along the way that would lead to that sports betting platform. And so we did the player proposition, you know, first the fantasy ratings, then betting on players.

And then the full season fantasy games. And then we moved into a sports book and then it was a couple of years of just adding more in play [00:23:00] content, making sure that if you, have a bet pregame, you can cash it out in play, you know, and we plugged in casino games, we built our own platform. We built our own, you know, sort of mobile web and retail systems every year there was something more to build on and did we ever get there? No, we never really built a strong US product with the US player proposition markets.

And, you know, there's always a roadmap and I think everyone's roadmap is always as long as you can see.

Leo: I remember how we had a mobile department and an in play department and all of that, so, it's crazy. When you think back to it now, the prioritisation there is super difficult, right? So how do you prioritise what kind of. Products, features, you implement, how do you recover from technical debts, uh, versus new features and revenue. That's always a really difficult internal discussion as well with diff many different stakeholders, not just as a, as a CEO kind of going, this is what we're gonna do. It's uh You need input from many different areas. What, what have been some of the most challenging things there where you, at the same time trying to catch up [00:24:00] with where the market's moving and you're trying to, I suppose, innovate or at least kind of, you know, get ahead of the curve.

How, what were some of the biggest challenges you faced there? 

David McDowell: Generally through the lack of capital. So we were always really underfunded. , If I look back, I think until, private equity guys came in, we'd only raised something like maybe 4 million pounds. gone from 2007 to 2019, got the company to, uh, to at least, you know, sort of break even profitability had launched.

A lot of them were white label sites that came up and, and, and disappeared. But probably 30 to 40 different brands had been launched on our platform. And the prioritisation, I never felt like we got it right because we were always, always sort of late and always sort of, I guess late's the wrong word, but we were always, I think, bending to somebody else's demands.

you know, we would have, one partner absolutely insisting that we build a feature and because [00:25:00] we had an outage, they've got more strength in that, in that in their voice louder, and you want to give them something to appease them. But almost every single time that we built customer led features, they were an absolute waste of time.

When you're in the B2B space, you're a little bit, you know, you, well, you're a lot closer to the technology. You know what's possible, you know what, you know what you can do. You're trying to do the best possible, uh, thing to give your customers. tools that they can market with and they can differentiate themselves with.

But when you've got, you know, 20 or 30 different customers and they all want something different, you've got an absolute nightmare of a roadmap. And so what we were trying to do, and I don't think we were ever doing incredibly well, was making sure that we had strong leadership in each of the teams.

You know, so we had a casino group, a platform group, a sports book group, a front end group, and you know, compliance group and trying to make sure that everyone had their [00:26:00] own list of priorities and trying to help them set not only the priorities, but the urgency level and sort of the cost and the value to try and push some of that decision-making down to the organisation and trying to work with everyone to understand the context of.

What do I need today? Because something's going to break. We're gonna have a catastrophic failure. Or what do I need to have in place six months, nine months, 12 months from now? Because the volume that we're expecting will cause a catastrophic failure. Or, you know, we can't sell in the marketplace to this group of customers until we get this, and every, every group had a different list of priorities. And then, you know, with fairly tight capital constraints, you know, the gambling commission comes along and says, we're going to, uh, start hitting everyone over the head with a sledgehammer and all the effort goes to regulatory compliance and then You know, your customers are saying, we haven't had any new features. So you swing back and you [00:27:00] start trying to do a bunch of features to make them happy. And it's and it's a really difficult proposition. I don't think there's any magic solution to it because it's, to some extent, it's juggling. 

You do have to try and figure out what are the most important priorities and because of those things, I guess what I was trying to illustrate is Because of capital, because of external influences, be it a regulator or a customer, or, or just a scalability issue, your lens constantly changes on what's important and all of those are almost noise to the vision.

You still have to kind of make sure that you're building your own vision and not just taking care of these other things, but you know, how do you juggle urgency versus important?

Leo: feels like you're never there. Right. That end vision.

Like it's and it's a goalpost that keeps moving. if you feel that you, you haven't figured it out, that's actually totally normal as well. because you are constantly trying to catch up. cust Customer led features, of course, are important.

You need to have your roadmap led by what customers want and need. But, uh, having your [00:28:00] entire, product roadmap determined that way, can really be a, a waste of time because you're gonna be behind, you're gonna be, be catching

up and that is not a good place to that's not a good place be 

David McDowell: It is difficult to make those decisions because you're trying to appease a customer and you're trying to grow your business development. You're trying to make sure your team are focused on, on the most important things. there's a challenge of always second guessing yourself, I don't know that what's normal. I don't know what other people think in their heads. I think that when you come to, looking at the CEO role, I think people have this idea of a really strong leader who knows exactly what they want, and they second guess themselves. They're right, they're intuitively right.

They don't even have to look at the numbers. They just kind of mail the report and they digest it and they say, oh, no, do this, this, this. And they're, you know, they're authoritarian leaders. They tell you what to do, you know, but they make you feel good about it. It's just like this, you might as well like draw, you know, [00:29:00] a cartoon superhero.

the reality is, is that, yeah, I think the human nature is to second guess yourself or, you know, in certain personalities. I know with mine it's always, you know, kind of second guessing And what it does is it leads you to, not take decisions fast enough.

I think eventually you start learning how other people view you as a leader. And, you know, rightly or wrongly, you know, I, I think it's important that when you are leading people, everyone's got a different leadership style, right? Everyone, everyone's com completely different. And I think if I go back to some of our, some of the for me the best times at FSB.

And when we were growing the fastest, my co-founder Sam and I were, really, the management team. We had Mark Wilson leading our sports book. We had mags who was, executive assistant office manager and you know, chief culture officer we had that team.

We were growing from sort of 10, 15 people up to 75 to a hundred people, and it was a [00:30:00] very flat organisation. And I think we were just incredibly transparent with what we were trying to do. Everyone knew that we were, trying to become legitimate enough to be called a challenger brand. you're winning small business, but you know you're going for it.

You're trading, you're watching your trading volumes going up, you know, you're looking at, you're integrating casino games and you're looking at some of the turnover going up and, and you're building as fast as you can and you're, you know, you're putting new brands out and you're scaling. And, there's a lot of oxygen in the room and it was really, really fun.

I look back on those days really fondly because there really wasn't any politics. There wasn't anything to hide. I think everybody knew they could come in and, and talk to me about anything. and it was fantastic. But you hit, like, a hundred people. and You start trying to figure out how to scale.

Now, you know, this is not, this is no longer a startup, this is a scale up.

And you know, at that point you've got challenges [00:31:00] of how do you build a team around you and how do you make sure that that team is made of the right people. And you know, I think that if you get those decisions wrong, it's incredibly damaging.

And I, you know, and I did get some of those decisions wrong. I got some of those decisions, right? I got some of 'em wrong. and I think that, if I just kind of look back on some of the most challenging decisions I've had to make or have failed to make in time over my career, it's usually about knowing in my gut that something is wrong.

That someone is wrong for the organisation. Not necessarily their skills. In fact, I don't think it's ever been because of their skills. I had one person I had to remove at a senior position because of, because of their skills. And it was actually pretty easy conversation. it's when the person has skills but is not a cultural fit that I think I've, some of the hardest lessons trying to figure out, trying to move that person on and [00:32:00] not even sort of my team, I'm thinking about like individual developers. Like when you've got a team and you've got three or four developers, and one of them's not cutting it, but they're doing about 50 to 60% of the work.

And you don't have a lot of capital and you get rid of that person, you've now got a void and you're doing 0% to the work. And then you might have months before you can get somebody else on and you've got the HR risk and you're trying to, trying to get to another fundraise. Do you remove that person?

I think the answer is always yes. If you know they're right. If you know they're not right, you have to do it. And that's probably my biggest mistake, is waiting too long

David McDowell: on things like that because I thought we need, you know, we need this. We can't afford the disruption right now.

Leo: Yeah, The the the difficulty is also that that person that's not really a cultural fit or not a cultural fit at all Uh f It's not really hard facts, right? It's not a KPI that you can point at that way you can fire somebody over. 

They're typically actually [00:33:00] high performers that, are, really important to the organisation or an area of the organisation. And c it's, it becomes dis disruptive for, for a large part of the rest of the organisation when you remove them. So, so that gut feeling decision, I completely get, it's very difficult to make and you wanna have all the facts and you wanna, uh you wanna make, uh, decisions based on, based on data, but you can't in those moments. 

And I think that kind of goes to some of the truths in, in ownership, entrepreneurship, CEO We've gotta make decisions all the time without having all the information. That's a very hard thing for a lot of people. what have you learned about that over time? Not always having all the facts, having to make decisions with not all the data, being wrong when you thought you were right and, you know, carrying the, the scars from that.

David McDowell: For me, the biggest challenge has been around people again, like you say, you don't always have the data, you don't always have the hard facts if, if people are highly performing, [00:34:00] but you know, saying one thing behind closed doors and you're getting you a sense of something else from, from the rest of the team.

with FSB, we had people costs, we had data costs and, we had, you know, office space, those were our costs, right. you know, there really weren't a lot of decisions you could get wrong. there really weren't a lot of opportunities to make mistakes because, you know, in some cases we were really early buyers for data feeds that were kind of coming out and you're just kind of negotiating a deal and trying to get it at the best price.

And, and often for a startup you can, you can get a favourable price. so really, you know, for me, it was really all about the people and about the, the timing of new hires. And again, I don't think I got much right. actually, my father used to have an analogy about, about the golf swing, right? , There's this perfect golf swing and everybody has it, but you do a little bit wrong here. You do a little bit wrong there. You lose a little bit of energy here and you end up, you know, hitting the ball 150 yards, [00:35:00] off into the rough instead of 300 yards, and you're only off by a little bit here, and a little bit there, and a little bit there.

And, you know, I think that's kind of the entrepreneurial journey. If you're just keeping the ball in play, you know, if you're moving it forward, if you're advancing it towards the goal, that's a good thing. But every single swing, you're losing and leaking some energy. It's almost like I was mentioning before with the, with the fundraising, you can never raise exactly the right, right amount of money at exactly the right time.

You know, minimising dilution but maximising the runway and just nailing it because. You don't know, right? The budgets change. The timelines are gonna change. The assumptions of when you can bring your revenue in are are going to change. every decision that you make feels suboptimal.

That it feels like you're making the absolute right decision at the time, but when it plays out, it's almost always suboptimal. And I think just being okay with that, you know, be coming to grips with, that's just operating in an environment where there's a [00:36:00] lot of uncertainty. And if you can have a vision, if you can have a strategy that you're trying to execute and have that, you know, make sure that you're always making the decisions on that.

I think more importantly, making sure that you've got a team which are aligned and share that vision and understand it so that their decision-making can be aligned with it. Then you're building a, a, a high performing organisation. You know, if you've got a CEO that's keeping that vision in their head and not sharing it.

nobody can make a decision on their own. And you end up, you know, you need to tell everybody how to fix their work you didn't give them the guidance and you didn't give them the, you know, sort of the insight. And I guess you, you know, staying on that, like that theme of, of challenges, I think one of the things that I al always strive to be a bit better at, but have, have kind of learned is really important along the way, is giving people feedback.

Yeah. And it's not, you're not just giving somebody criticism, you know, you're not just going and telling something how they've done, they've done something wrong. [00:37:00] You are letting them know how you want something to be done so that it can better align with all the goals of the organisation. The one example of some really valuable feedback I got.

Really early in my career, as an engineering student, I had an intern program. I was on an intern program and, one of the industrial engineers came up to me and said, Dave, guess what? You're the intern. You get this really shit job. There's gonna be a lot of data entry for the next two weeks.

You're gonna literally take these numbers and type them into the computer, But let me tell you why we need this data in a spreadsheet and what we're going to do with that data once we're able to analyse it. I Was

very happy to do one of the most boring jobs for the next couple of weeks, just entering data because he had taken the time to acknowledge that the job was less than fun to show me how they were going to use the output [00:38:00] and to tell me why it was important.

If you can give people feedback along those lines, if you can kind of understand what they're doing, understanding the challenges, why they might have made a mistake, because they're dealing with imperfect information, that's okay. We just want to make sure that you know what they're doing.

You know, they've got some sort of clear guidance on, on what they are doing.

Leo: Yeah, it needs, like, your job needs to be, something that you understand contributes to the bigger why of the organisation. Right. And I think that's something instead of just following process that's the core motivation for someone.

So really uh really good advice There are moments as a CEO. you carry something really heavy, right? We were talking about, it's not about the hours, it's about the weight of those hours. , Are things that often you can't really talk to anybody about. Your wife probably heard you talk enough about work. Your friends don't necessarily run a business. Your employees would freak out if you would tell them, like in those kinds of moments. David, um, who would, who do you actually

[00:39:00] turn to or did you turn to?

David McDowell: I am not really sure that there, that there really was anyone that I turned to. I'm, I've got a couple of friends who are in banking or in private equity and if there's a very specific problem something that they would understand or, or have some advice on.

That's great. I think the biggest challenge is like the way you describe those situations. I tried to be as transparent as possible with the whole team, but there are moments when you are fundraising where you need to smile and put on a brave face for the organisation when you're looking at the numbers thinking, I've got six weeks, get this fixed.

and you can't share that, right? there's like, there's nothing worse. Like when you, again, once, once you've got the whole board involved, once you've got other owners, you know, we got the, you know, private equity guys in and if we're, if somebody's going to, you know, be removed.

also when I was exiting, you can't tell anybody, you can't tell anybody in advance. And your team know when you're not telling them the full picture, right? You [00:40:00] got people that you've worked side by side for 10, 15 years they know something's going on, you know, you can't kind of say, stop asking questions, please.

There isn't anyone to talk to really, you know, like you said, there's only so much you can bring home to your family. There's only so much you should bring home to your family as well. When it comes to compartmentalising, it's important that you bring sort of a little bit of home, that you sort of share some transparency about what's going on, but not all the venting, you don't want to vent at home.

That's not the proper place for it.

And, I was really fortunate to have a co-founder who, our areas of expertise. Didn't really overlap a lot, but they overlapped enough that we could talk intelligently about the other person's, work and area. So I think having a partner like that, it was really good.

David McDowell: You just don't, you just don't know how somebody else is thinking, what voices are going on in their head, if they're being stressed about it or if it's, you know, I know that, you could track my smoking habits [00:41:00] to fundraising.

Halfway through every funding round, I'd buy a pack of cigarettes. You know, that's not a that's not a healthy way, but I, that was one of the things that I would do at the end of, not the end, but in the middle of each funding round.

I'd end up leaving the office and going, walking around the block and having a cigarette. And it wasn't something I would normally do.

Leo: it's not just the challenges, this is also the successes. Right. It's one of the first questions I asked, my old CEO when I started a business is, who do you actually celebrate these, your successes with?

You know, I just, uh, I think it's, uh, yeah, it's just isolating sometimes. So, so, thank you for sharing that. Last few questions, David, 2022, stepped down as CEO after 15 years, FSB gets sold to every matrix 2024. When you look back, on like 15 years of building, what does it feel like when you reflect on that journey now?

David McDowell: Very mixed feelings. From 2007 to 2019 basically before we brought private equity in. Really proud of the team. I know I had made some mistakes, but, just working with [00:42:00] fantastic people, having a team, really having an environment that I think everybody worked hard, and enjoyed each other's company.

I thought that was really, really, a fantastic time. And, making that transition from getting a company up to profitability, having a really, really strong competitive position or proposition in the UK and Ireland, doesn't mean that you can just go and become globally dominant.

we had an investment thesis that was, you know, agreed by our, our financial, sponsor coming in that we would, make the required investments, get the platform, up to the standards needed, to compete in America, in wider Europe, compete in Africa.

But what was implemented was the exact opposite. Instead of an investment into the technology and then, and then scaling, it was, Nope, we're going to do hiring freeze. Everyone's, everyone's furloughed during COVID, and they're not coming back until you've got sales.

[00:43:00] And what it ended up doing was, we were just losing our momentum, and then we, for the first time ever, started selling things that we didn't have. And, you know, I really prided myself on having a business that we sold what we had, we knew what we could deliver, and we delivered, you know, what we, what we said we'd deliver.

It doesn't mean that we didn't make mistakes along the way. Everybody does. It doesn't mean we didn't have outages along the way, we did. But I could look our customers in the eye and tell them, this is what we've got. This is what we're building. And bring them along on that journey. And I think as soon as you make that switch to just build the business development team out and go sell, and then it's a nice problem to have.

You can't fix it. And I think that's really what we struggled with as an organisation. It's why ultimately the business was sold. I'm not sure any customers are still on the platform today, and you know. What we had built, in 2020. We were platform of the year from SBC. that was a real high for [00:44:00] us to, you know, to win that, one of the most prestigious, categories, you know, in, in those awards that was, that was absolutely fantastic.

We're just flying. but you need to, you need to scale up, you need to keep that momentum. You can't put brakes on the whole development team and just focus on sales and think that you can catch up. Because when you are implementing a new platform in Eastern Europe, in South Africa, in America.

The, these are large projects that take, even if you're reusing the core code, even if you've got sort of a, a, a multi-tenanted platform when it comes to local payment processing, local hosting, local regulatory challenges, local sports that are important, you know, different designs on the user interface.

All of these things take time to implement. And these are nine to 18 month projects and you don't have nine to 18 months, to implement them. Especially when you don't have a team and you start hiring them after the contract's signed. So, for me personally, hugely frustrating to end because I felt like, [00:45:00] we got the company to be a real challenger brand, uh, and then we didn't make the most of it.

Leo: Thank you for, for being so open and honest about that. That's some real wisdom there. because it's something that I think many businesses struggle with, right? The, that switch to, okay, we need to generate revenue. How do I stay honest to where the product is versus the big that I perhaps believe I need to make to, to get the sale done?

David McDowell: I think what one of the things that FSB did really, really well, and this is, the way that we integrated data feeds ran our own models, having that technology where we could really take the best from each of the suppliers rather than having a sports book, which was just, you get all your data from one supplier, I think was incredibly unique in the marketplace.

And I, um. personally really frustrated that we didn't get to the scale, that we could implement that because I think it was a much better sports betting platform you know, the core, the [00:46:00] guts of what it was. The risk management tools were fantastic. I think that the data management was second to none.

But we didn't have the scale. so when the US market opened, I think quite frankly, our investors were, along the lines of, we can sell to a US company. We can flip this to a US company. But we didn't have the critical mass of revenues to be of interest, to be taken out at, at the very highest levels.

Leo: Okay. My, my last question to you, David. so where you are today, right?

As an entrepreneur mentor, if you would be able to go back to 2019 and to talk to yourself, you know, at that point of finally reaching profitability, looking for private equity to scale, like going into a new phase of business, what would you tell yourself today if you could go back to that, that point in time?

David McDowell: that's a good question. And I, I think it comes back to my earliest comments around, boards acting in the company's best interest or acting in the individual's best interest. [00:47:00] And, the right thing for the organisation to do was to raise money and we had, strong enough voices on the board that were demanding liquidity I tried to fix by bringing private equity on getting them liquidity and, it just didn't work out. I think that was probably the best solution given the constraints. But if I go back and, and, you know, find a way of doing a better job of convincing the board, not to try and create a liquidity event, but to actually press forward because now we're on the cusp of something.

I think that was, that was what I sort of, you know, failed to achieve. I think if we could have kept as an independent company and brought two, five, 10 million pounds into the organisation, we'd have a very different story, and I think it's where, where the wheels started to come off was, again, it's, it's around those board, board level decisions.

Leo: David, thank you so much for sharing your [00:48:00] story. It's been fantastic talking to you. And, uh, thank you for being so open and honest 

David McDowell: yeah. Thank you. It's been, cathartic. it's, It's really important to, I think, to not beat yourself up when you're in a when you're in a, a, a leadership role and to recognise that you know, mistakes will be made. It's par for the course, it's normal, and it's about not getting caught up on the mistakes.

It's about just kind of moving forward and continuing to make progress and, and, and staying positive and, uh, yeah. Fantastic. I think you guys are doing a great job with everything that you're doing over there as well. I think getting this message out of it's okay to, you know, have doubts, it's okay to second guess yourself.

That's just, that's just part of the human experience and, um, yeah. Thanks for having me on.