Season 1: Control the Controllables: Simon Dent on Building Brands, Businesses and Ultramarathon Resilience

In this episode of Progress in Practice, Charlie Reading sits down with Simon Dent, Chairman of Firmative, the creative company that puts brands in culture, working with the likes of Netflix, Atlantic Records, Sony and Universal.

Simon is the first guest to bridge Charlie's two podcasts, The Business of Endurance and Progress in Practice, and the conversation shows exactly why. From cutting his teeth as a London club promoter to founding sports creative agency Dark Horses, and from hitting rock bottom with his mental health to completing more than 30 ultramarathons, Simon's story is a masterclass in resilience, relationships, and doing hard things.

Whether you're scaling a creative business or simply want to build a stronger relationship with discomfort, this episode is packed with honest reflections and lessons you can apply immediately.

Key Talking Points

What it really means to put brands in culture and why so many brands gatecrash and make a mess.

Firmative's "third way of working": blending strategy, creative and production to deliver hundreds of assets at speed.

How club promoting taught Simon to sell, build communities and manage a P&L before Instagram existed.

Simon's advice to his younger self: you can't do it alone; never be the smartest person in the room.

Why diluting equity to bring in best-in-class people beats hoarding it.

The wisdom he'd pass to the next generation: build a relationship with hard things, because they're coming anyway.

How hitting rock bottom with depression and anxiety redefined what pain means, in running and in business.

The link between endurance sport and entrepreneurship, and why you don't grow when you're comfortable.

The biggest challenge after 50% growth in 12 months: cash flow, payment terms, and recruiting senior people who understand culture.

Why the first five hires define the business.

Simon's guiding framework: control the controllables- in the boardroom and at 500km into an ultra.

About the Guest

Simon Dent is the Chairman of Firmative, a creative company born out of the music industry that helps brands become a welcome guest in culture, working with major record labels including Atlantic, Sony and Universal, as well as global brands like Netflix.

Before Firmative, Simon founded sports creative agency Dark Horses- named one of the fastest growing agencies in the world before its sale to Omnicom's TBWA, and launched a sports talent management business, which he sold to ROAR Global. He is also an accomplished ultrarunner, with more than 30 ultramarathons to his name, and shares his journey as @ultraentrepreneur on Instagram.

Find Out More

Firmative on Instagram: https://www.instagram.com/firmativehq/

Simon on Instagram: https://www.instagram.com/ultraentrepreneur/

LinkedIn: linkedin.com/in/simon-dent-9509b728

Resources Mentioned

Dan Sullivan's Who Not How principle

Charlie's Culture Cultivator session: https://youtu.be/tFC4EyQHLrI

The Business of Endurance podcast: https://www.buzzsprout.com/1373434

About the Podcast

Progress in Practice is brought to you by The Trusted Team- helping professional service business owners build scalable, saleable businesses while working less and enjoying more.

Find out more: https://thetrusted.team

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If this episode resonated, make sure you follow the podcast and leave a rating and review. It helps more founders discover these conversations and allows us to bring you even better guests.

Until next time, keep making progress in practice.

Transcript

SPEAKER_00 0:05

Welcome to Progress in Practice, where we explore what it really takes to build and sustain a professional service business. The hard letters, the smart moves, the uncomfortable truth. Because success leaves clues. If you're willing to look for them. I'm Charlie Redding. Let's dive in. Simon, welcome to the Progress in Practice podcast. I'm looking forward to chatting to you and interviewing you again, actually, because you're the first person that's bridged the business of endurance and the Progress in Practice podcast. So looking forward to diving into this and all things about uh Fermative. So, what I like to do to kick things off is for those people that don't know anything about you, who do you serve? How do you help them? And what makes you guys different?

SPEAKER_01 0:56

Wow. I mean, firstly, thanks for having me on. It's good to see you again. And lots has changed and not much has changed. So diving straight in, I've had the privilege of working at Fermative now for about 16 months. And the story goes that the founder came for an interview at the ABCI founded around 10 years ago, didn't get the job, but apparently I gave him some good advice, which was to focus on your passion. And so he went off and built a new music-focused production business. Um, very successful, working with the likes of Atlantic, Sony, Universal, Record Labels. And then 18 months ago approached me to ask if I could come on board to be as chairman. So we we sort of got to an agreement pretty quickly. And and in that that last sort of 15 months, um my role has changed quite a lot. And affirmative as a brand, as a creative company, as we like to call ourselves, we very much put brands in culture, and not only put brands in culture, we we we make sure they stay there and help them become a welcome guest in culture. And that's something really important because we all know how brands often gate crash culture, take the best bits, and leave it with a mess. Um, with our background in music, sport, entertainment, fashion, we've got two very distinct groups of people at the business. We've got the very young people who are in culture, and you have myself and my strategy director James, who are very much in the background. Um so we're the operational, boring, strategic people, and we have some really cool cats who are putting brands in culture.

SPEAKER_00 2:26

Brilliant, brilliant. I love it. And and what when you say put brands in culture, for those of us that kind of might be questioning exactly what that means, describe, give us an example.

SPEAKER_01 2:37

Yeah, I mean, look, that it can manifest itself in all sorts of different ways. Um, the usual agency lens, it could be with strategy, creative, production, experiences, all of which we do in-house. As I said, we uh we have our roots in music, and as you know, music is very much at the heart of culture, as is sport, which is obviously my background. But yeah, we're working with the likes of with Netflix. We're about to launch a very well-known US whiskey brand in the UK. So yeah, it's it's it's I suppose it's it's having the insights and understanding how we can sew a brand story into culture authentically, and that can take time and not upsetting the culture. So, what we're obviously not about is sort of gate crashing events. You see so much stuff, especially this summer. Actually, there's there's a lot of well-known brands sponsoring music festivals, and they'll make a real hash of it. They're incredibly jarring the activations, what they do. But yeah, on briefs like that, we just make sure that the the brand plays a really useful role and actually makes experience better rather than acting like a leech and sucking all the life out of the culture.

SPEAKER_00 3:45

And and I guess what makes you different is that sort of piece that you're trying to really align these brands with the culture as opposed to just essentially slapping it with a sponsorship label.

SPEAKER_01 3:56

I mean, yes, and I think what also is really important to stress is that we are we're a creative company that's born out of a very agile studio. So usually the way around it works is that a creative agency who's making makes ads will try and launch a studio that can create content efficiently and and in an agile nature for its clients. Whereas because we're born out of speed and quality, it means we can create a lot of assets for our clients. So we've got a way of working we call the third way of working, which is a lovely blend of I guess strategy, creative, and production. So with Netflix, for example, we are we've got quite a long-term relationship with them now that we're shooting once a month with them and create hundreds of assets that they can use um across their channels. Likewise, on a music video, on a music shoot for, say, for example, Atlantic Records, we can capture hundreds of assets that if you were to ask a more traditional advertising agency to do it, it'd just be impossible because they don't have that way of working. So, one of my main roles over the coming months and years is to preserve that way of working, but I get guess put a bit more grown-up process and dependable, I guess, rigor around it all. And that's that's the exciting part for me because I think um I've seen it work in some bigger businesses, but I think with Fermative, there's a real opportunity to create a niche for yourself in the sort of creative age of the landscape.

SPEAKER_00 5:26

Brilliant. So I know you've got many different businesses and had many different businesses, but what's the story that best explains why you do why you're a part of this business? I mean, you sort of mentioned it in terms of the founder, but is there a story that kind of best explains why you do this?

SPEAKER_01 5:42

It's a it's a great question. And actually, myself and the founder of Affirmative have the common thread, and that is we both cut our teeth as club promoters. Um, I think I mentioned this when we last when we first met. I was a lawyer, didn't work out so well, and found myself around 2002 with my partners, colleagues, running 17 nightclub events a week in London. And at the time, that was a parachute that I found and was not aware of the the personality traits and the skills I was developing. And funny enough, Dummy, the founder of Affirmative, um very similar except he started club promoting whilst at university, promoting student nights. And I think in everything I've done, whether that's working as a sports agent, launching Save Our Souls, Affirmative, Publishing, the skills of uh sales, the skills of building communities, I suppose, creativity at work, high performing creativity, like you know, in 20 years ago trying to fill a nightclub, there was no such thing as Instagram. It was calling people and asking them and convincing them to attend uh what was effectively a black blacked-out basement in Soho. Like it you do learn to sell in that environment, uh and managing a PL, all these things that I guess it became nature at running club nights. But I I think as well, the biggest thing that it gave me, and Dumi talks about this as well, is just the the ability to meet people and find common threads. Because again, if you're you know, I was out whatever, four or five nights a week in nightclubs, you very quickly have know and work out how to mix with the people from all different backgrounds, and I think that is a skill that I've just honed in and and now as a I guess on the tip of the spirit of our new business. I'm I'm aware, really, I'm really aware now that I've got a very big network. Like it's often said, like, you know, lots of people. I I didn't really know what that means, but it's really starting to land now that I do know a lot of people, and I think that has come from that that skill set I was given as a club promoter. So yeah, look, I think where affirmative is and the background we've got, I think it's um it's really interesting that two of the founders uh from a club promoting background.

SPEAKER_00 8:00

Interesting. And and obviously you've had that you just alluded to some of them there, but you've had many different businesses in different sectors since those days. But if you could go back to that younger self, that club promoting self, and pass on sort of a bit of advice, what would you say to your younger self then and and why?

SPEAKER_01 8:20

Well, nothing could happens after midnight, but that's probably a different thing. I would just say that in an ultramarathon. Oh, yeah, true. But no, I think that then I mean there's bangs of things. But I think I think the one thing that I definitely has landed in the last 10 years has just been you can't do it alone. And I think the I think as a sort of a young man, you know, failing in law, wanting to prove himself and prove people wrong and and and find a thing and and something new. I think the I was probably quite misguided for 10, 15 years that I can do it myself, I don't think anyone else helped. Whereas really with I think it's probably with the the experience of dark horses and that the that the first creative age I found was just two real guiding lessons, which were never be the smartest person in the room, and and I always used to refer to it as stand on the shoulder of giants, so always make sure there's people in your leadership team that know more than you. And I think that is just again at Fermative, we are it's a really exciting time. We're about to go on a bit of a recruitment drive this summer, and again, it's sort of it's just remembering that you've got to find people that are smarter than you, you've always got to put those people in the room, and and and that for me is quite big insight because I I do think that in my 20s it was all about me, all about hoarding, I want to keep the equity, it's my business. When actually, if you're starting from a pot of 100 points, you absolutely should be diluting to brim and best in class people.

SPEAKER_00 9:46

That's interesting, isn't it? And I think if we think back to what you sort sort of talked about with the club promoting days and and that that advice um that's run through those businesses, you can like I think Dan Sullivan would term that who not how, wouldn't it? Yeah, it's not you don't have to be the person that knows how to do it, it's finding the who's to help you on that journey.

SPEAKER_01 10:06

Absolutely, and then listen, I've always I've always been very clear that I've never been, you know, I I always used to be a hard worker. That was my thing at school. Like I was never an A student, but I'd scrape a B, but it would be really, really hard. But that yeah, and so the writings on the wall from early doors, right? You know, I was I was definitely no Elon Musk, but I I sort of as I said, developing the the ability to build relationships. I do know some really good people that I've I've you know, wherever I get the opportunity, I'll bring them into my world.

SPEAKER_00 10:39

And often often that also that scraping a B, that working really hard, often they find people that I would describe that as me. I mean, I I scraped a B, a C and a D, but but but I looking back, I was dis I well, I am almost certainly dyslexic, I've never bothered getting tested. But actually, they say dyslexia is an advantage in being an entrepreneur. Yeah, because it teaches you that lesson that you've gotta really work hard and try lots of different things other people don't have to try to get to where you want to get to. And that's kind of like the best lesson in being an entrepreneur.

SPEAKER_01 11:13

And it just becomes second nature, doesn't it? And you know, people are always like, Oh, you work really hard. I'm just like, this is just what I do. Like it's not, I don't, you know, I don't need to be credited for it. I just it's just it's just my minimum setting.

SPEAKER_00 11:24

This is helping. And so if we can think take this to a another level and think deeper on this, if you could leave no money to your next generation, but just some some wisdom or some advice or some values, what would that be and and why?

SPEAKER_01 11:39

Again, you know, it's quite a lot of things, but you know, the the one thing that uh through business and personal circumstances, I think the the one thing that I do refer back to quite a lot is doing hard things. And I think that it's almost a cliche. I feel like I need a t-shirt on.

SPEAKER_00 11:58

But it's sort of I I feel like Well, you sort of have. But those people listening, he's got UTMB on his t-shirt. So he saw Hal's got that rate on it.

SPEAKER_01 12:06

I just think that the sooner you build a relationship with really hard things, the better you're going to be equipped in life because they're coming at you anyway. Like, and if you can voluntarily put yourself in a situation where you're making friends with pain, um, you will absolutely just never have an enemy because he just I it started for me, as I said, with mental health challenges, and that was obviously not voluntary. But you know, when I fell out the legal fresh and I had I had some real challenges and ended up in a private hospital with depression and anxiety, and but that was for me was sort of that I really understood what pain was then, and that became a sort of moment in my life where I didn't, you know, I knew I'd hit rock bottom. So then when running was introduced to me and I started running marathons, and there was a bit of pain, I was like, that's not pain. I've I've seen pain, I know what pain is, and then you unlock ultras, then you unlock a thousand kilometers, and and you sort of whilst doing that in the sort of I guess the world of running, you're then making the the things that happen to you in the world of business a lot less powerful and have less ownership over you. So, you know, I'm never frivolous and I'm I'm I I never disregard any negative or bad or painful things in business, but I don't really let them affect me because I know what real pain is. So I think that, yeah, if the sooner that you can expose yourself to things that are painful, um I do think it makes you a more all-rounded human being.

SPEAKER_00 13:33

Brilliant. And what I love, and I love what you've just done there, because I was gonna ask you to do this at some point, but you've done you've done it naturally, is we've built a bridge between the business of endurance episode and the progress in practice episode. Because I I think there is such like I I probably found uh endurance sport much much later on than you did, but boy, did it make me a better entrepreneur because because you because you like you say, you learn to do hard things. And do you think that's the success behind the the rise in endurance sport, or do you think there's anything else to that?

SPEAKER_01 14:08

It's a good question. I think endurance sport, certainly with the what I'm doing, is is very attractive to a lot of people in their sort of mid 30s to 40s, and I think that's there's a lot of and a lot of people that I you see at the start and I see these events have had things happen in their their private lives or business lives that have been challenging, and they do find comfort now in in endurance sports, and I think that community is very powerful, it's very strong. But yeah, I think that the there is a rise in endurance sports, but it it's quite it's quite niche, I do think still. I don't think and listen, running is definitely become a big thing, and park run has been incredible, and we've got all these record entries for London Marathon, but actually, yeah, I it's interesting. I don't it's a good question. I don't know which comes first. I don't know whether yeah, endurance runners get into business or business people get into endurance. I I I similar to yourself, I think my they track in parallel, they have they were happening at the same time and feeding off each other.

SPEAKER_00 15:05

Interesting. My my my endurance sport definitely came later for me, but it made me it made me better. I'm thinking back to some words. I remember when I interviewed Joe De Senner, he said that um it used to be that life was really tough. You know, if you were growing up around one of the world wars, life was tough. You didn't need to do in tough stuff when you were home, but now life is a bit too comfortable, and actually doing tough stuff when you're not at work is is is definitely also good for good for the soul.

SPEAKER_01 15:32

And it's about growth, isn't it? It's it's just about personal growth. And and I always you don't grow if you're comfortable. Like it's as simple as that. And I think that And that just is such an insight that I think you know, I know that I'll never retire. And now people might say that's unhealthy, but I couldn't think of anything worse than sitting on a beach or playing golf or and that's just comforting because I I you know for me every every challenging event or business that I'm involved with, I become a better person. And not just a better business, a better athlete, but a better parent, a better husband, a better friend, and so yeah, that's yeah, it's it it's it's a good discovery, and I and I do I don't preach, but I do I hope that with some of the content I create for you on my Instagram or YouTube, whatever, I only want to inspire.

SPEAKER_00 16:19

I don't want to preach. But I agree with everything you just said, and and ultimately, if you're not growing, you're dying, aren't you? So you've got to be moving forward. So, what's the what's the biggest obstacle that's blocking you from achieving your goals with Fermative at the moment?

SPEAKER_01 16:33

Yes, uh it's it's a really interesting time. As I said, we've we've had uh incredible growth, 50% growth in the last 12 months, which we're incredibly proud of. Dumi and the team have done an incredible job. And I think we are now we're in this phase actually where we work with some big international brands, and without getting too granular, uh sometimes pay payment terms aren't too favourable. So we're the the the managing the cash flow is quite hard. Um we're quite a junior team. Uh as I said, James myself and Dummy in the leadership group are our our team are quite young, so it's sort of it's empowering them to make decisions, helping them guide them. But the reality for us, the challenge for us is is onboarding more senior people. And so for the next six months, the second half of this year, yeah, the exciting challenge will be bringing on more senior people who and again where the challenge lies is people who are in culture, who understand culture, but also have that that rigor that that you only get probably with experience. So it's it is a challenge to find experienced people that are in culture, and and that that is the challenge I have. But isn't listen, it's an exciting one. Uh, we're in the right conversations, we definitely have a healthy new business pipeline. I'm sure there's more work for us to get from existing clients, but we're just focused now on doing a good job on the briefs we've got, and um, you know, we don't want to drop the ball there.

SPEAKER_00 17:56

Brilliant. And and I think you're you know you're right in that the when you start recruiting, particularly when you start recruiting at a quicker pace, then it's very easy for that culture to become very diluted, isn't it? And so recruiting around culture is such an important thing. I know Yeah.

SPEAKER_01 18:12

One bad apple as well can can really turn things down, and you know, yeah, it's yeah, I I've learned that. And I think that that's for me is very much something that that we're aware of that you just gotta get the right people on the bus early doors. And and then especially I I always say the first five hires will define the business.

SPEAKER_00 18:29

Yeah, yeah, yeah. And and I think so Google always recruit through the through their culture, through their values, and there's a there's a huge amount that we can we can learn from how they how they did that. Uh I've actually got a session that I call the culture cultivator, which I'll I'll share with you, I'll share with you afterwards, and I'll I'll put it in the show notes for for anyone else that wants to follow up on that because it is it's a real challenge. And I think particularly in today's world, in a hybrid world, like maintaining that culture when people aren't even hanging out in the same building can be really tricky.

SPEAKER_01 18:59

Yeah, that and that's a challenge I'm you know, I'm not um I haven't had as a leader, really, to be honest. So that you know, uh only really in COVID, which was a bit crazy, but I think yeah, there's definitely a model that suits those that that want to spend a bit of time at home and those that want to come in. And I think, yeah, we'll we'll get there.

SPEAKER_00 19:15

Okay, brilliant. And what book, mentor, framework, documentary, whatever it is, do you have you found sort of most valuable on your journey? And where does it show up in your business?

SPEAKER_01 19:27

I mean, I could swim my camera to the bookshelf. Your book's on there. I mean, that's my my book's on there. Yeah, excellent. Love it. There we go. It must be that one then. No, I'm joking. Pick another, pick a. I mean, there's so many. I think, and to be honest, rather than a book and trying to sort of summarise one of the many books I've read. I th I think something that definitely applies in both running and with business is just controlling the controllables. And I think that is something that just harden back to what we were saying earlier about working hard. I think if you maxim effort, always prepared, have discipline. These are things that if you do both at work and in running, then there are certain things, whether it's the situation in the Middle East, whether it's thunder and lightning on an ultra, whether it's there's this stuff that's going to happen, but I think as long as you can go into any event or any quarter or meeting or pitch, knowing you've done your best, it's fine. And and again, I I say that both in the office and at the end of the race. Like going back to we were chatting about my attempt in Australia to run a thousand commissas, like I prepared so well, and basically I got a stress fracture. There was nothing uh that there was nothing I could do about a stress fracture in my leg 500 kilometres in, and so I wasn't downbeat. I just was like, Well, I I did it, you know, I gave it a really good crack. I felt healthy, my mind was strong. And it's the same with any pitch. Like, if if we've all honestly done well and we've put maximum effort in and we don't win it, then we didn't know who we're against. We can't control what they did.

SPEAKER_00 21:08

I love I love the statement control the controllables. I I think it's it provides if you can and it's it's not always easy to do because you can get caught in your head, can't you? But um, but yeah, I think it's absolutely brilliant advice, and I think it's a great framework to to stick to. For those people that are listening that want to find out more about you or find out more about Fermative, where's the best place for them to track you down?

SPEAKER_01 21:30

Um, definitely on Instagram. So, yeah, affirmative HQ on Instagram. My Instagram is at Ultra Entrepreneur, and then Simon Dent on LinkedIn. But yeah, we yeah, please give us a follow. Please reach out, whether that's yeah, from a sort of yeah, personal point of view or even just uh yeah, affirmative point of view, get in touch. We'd love to hear from you.

SPEAKER_00 21:47

Brilliant. Simon, it's been an absolute pleasure chatting to you as always. Love the fact that we could create that bridge between the business of endurance and progress in practice. Um, and as a reminder for those people at home, the the Progressive in Practice podcast is brought to you by the Trusted Team that helps service-based business owners grow their business while working less and enjoying more. Um and I'll put all the details for the trusted team in the show notes as well. Simon, it's been great to catch up again. Thank you so much for coming on and I wish you every success with both Fermative and your next running challenge, which is I think to do a PB at the marathon. That's right. Thank you very much. Go to see you again. If this conversation resonated, you'll find more support, structure, and community inside the trusted team, where ambitious service-based founders come to build businesses that are scalable, scalable, and sustainable. You can find out more at thetrusted.tv. And if you're enjoying Progress in Practice, please make sure you follow the show and leave a rating review. It really helps more founders find these conversations and to bring you better and better guests. So until the next time, keep progressing.