Hiya babes. Welcome back to another instalment of Creative Careers (an extremely unsatisfactory working title that’ll do for now) where I talk to creative people who’ve experienced (or are still experiencing) big, small or just plain interesting transitions in their careers. If you’re new here, hello, I’m Gabby Jahanshahi-Edlin, branding and communications strategist, founder and former CEO of Bloody Good Period, and award-winning social entrepreneur. This is an interview series within my main newsletter, Post, in which I, um, try to get free career advice from people I respect.
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This instalment contains a very inspiring chat about the work, life, and brain workings of Damola Oladapo. Damola is the founder of creative studio, House Captain and a freelance creative director, copywriter, journalist. He’s worked with some of the world’s biggest brands including Nike, Spotify, FIFA, Campari Group and Gorillas. I first met Damola a decade ago as we both embarked upon our Masters in Applied Imagination in the Creative Industries (Design Studies) at Central St Martins. Two of a very small handful of Brits in a richly international cohort, we bonded quickly. These days I don’t get to see enough of Damola but we always seem to collide when the time is right. I’ve had him in mind to interview since I started to plan this series - not only do I love his work - it’s so full of energy, it’s smart and it’s funny - but I was delighted to see he recently made the transition from agency life to setting up his own creative studio, House Captain. After deciding that we were, sorry, just not up for venturing out in 0℃ weather, we caught up online and I got to spend half an hour feeling inspired, uplifted and impressed. I hope you enjoy hearing from Damola as much as I did speaking to him.
Need to know: I’ve included links to and pictures of Damola’s work, and his contacts at the bottom. Also, the interview has been edited for length and clarity because we do like to chat chat chat.
Damola looking tres chic.
GE: You recently founded House Captain. Can you tell me a bit about it - would you call it a creative agency?
DO: It’s a studio rather than an agency. I'm very, very intentional about making that differentiation between an agency and a studio because the agency model in my experience is a bit vague. I kinda left the whole side of the industry behind to build something that gets to the purest essence of what I think moves the needle.
Ideas come from a confluence of places. Having a studio that means it's more of a meeting of minds, rather than a set of hierarchies. The studio model is more freeform and spontaneous, but there is still very much a collective goal of making the best thing possible. It’s about the variation of voices. That was the biggest thing that pissed me off in the agency world. And it’s the same across most business segments and industries. Typical clusters of power and echo chambers. other voices that were great with much to offer , but they would get discarded as ‘’challenging’’ since the suggestions or challenges weren't coming in the right package.
When it comes to starting something it comes from, I guess, personal frustration or a gap in the market. But I always knew that having my own thing was going to be the way I would hit my fullest potential. I’d had the idea for House Captain bubbling around in my head since I was 21 - in one iteration or another. But this iteration, the right iteration, came at the right level of maturity and experience.
GE: Being a founder takes a really broad yet specific set of skills. What do you think are the ones that really matter?
DO: Conversation. There are always conversations happening and that's the thing you have to be prepared for. You're gonna be communicating nonstop. And talking isn't just verbal - it’s email, it’s WhatsApp. You're going to be talking all the time. And you know, luckily, I've been blessed with the gift of the gab! That’s helped me balance out the other stuff and expedite the harder work. So the soft skills really really matter. Then I can “one-two-punch” with the hard skills of the other stuff, which is concepting, strategising, etc.
We've got to be strategic with the work that we do and how we look at the landscape as well. One of the key pillars for House Captain is strategy because I found that some agencies just want ideas that don't have a basis anywhere. I’d ask “what is your thinking based on? What's your source of truth, what's your tension?” And a lot of these ideas that clients love [at first] don't have a foundation and that's why they fall flat later because they don't have a strategic base. And I saw this was happening a lot. We're going into these rooms with great concepts and great thinking but it falls flat. Because the client’s realising you've got your dinner out, but there's no table to set it on. So of course it's going to drop on the floor. Your plates are going to smash. No soup for you.
GE: I think that’s why your work feels so really culturally relevant. It feels exciting. How do you get better at that? How are you building those skills that you've outlined above?
DO: Outsider’s advantage. The outsider’s advantage is key. It took me a long time to get into the game, so I've created systems, curriculums, and methods for myself that were agnostic of the industry. The advertising industry creates a narrow path to entry (do you have the right internship etc) that I decided I'm just gonna come at this from a different angle. Barriers to entry for the industry fuelled me to figure out my own set of principles and style.
And now those principles are how I secure opportunities and run House Captain!
GE: How do you stay inspired?
DO: It's gonna sound cliché, but it comes from a range of places. I love to travel; I spent November in Korea, which was great. It's that full-blown cultural shift - I love sitting in different cultures and taking in and assessing the norms. And reading is my bread and butter. I’ve been reading since I was three - my mum's very proud of this. Reading gives me abilities to play around with tone of voice - books are conceptual lenses - they allow me to think in different ways.. And finally, being active. I love running - it’s a big part of my inspiration. It keeps my brain fresh because I’m too impatient to meditate, so I need to run. It helps slow me down. And I'm always somewhere! If it's a party, if it's an exhibition, if it's an activation, if it's an event - I need to be immersed in the world basically.
GE: And finally, what would you tell 18 year old Damola about work?
DO: What a slacker! [laughs] I don't know. What would I tell him? I would tell him to double down on his convictions. You have this very tight idea of what you want to do - you just don't know how to do it, because you don’t know how to get to that place. It feels like it's impossible. It sounds clichéd as fuck, but go with your gut - your gut is driving you in that direction. Follow it! Don’t be afraid of looking or being lost. It can be hard for a teen to go against the grain and not go to uni. To choose a gap year to quite literally do some thinking. I think he needed a literal gap year to decompress because when I think about being a teen, I think 18 year old me was knackered. . I wanted to be in the creative world and have something of my own. I didn't actually learn about advertising, formally, until I was 20 - shout out Mad Men. I had always loved it, was always coming up with puns and taglines and ad concepts of my own.. I didn't even know what the hell a copywriter was until I was 20 - which is wild.
So now I look back, I'm like, oh shit, all that kid needed was a bit of space and time to make a decision. So, 18-year-old me: say no and double down on your conviction, saying no matters, saying no is knowing your values.. When I have kids, I'm going to make sure they say no more than yes Until they feel that resounding yes excitedly and frightfully buzzing about in their stomachs.
Check out some of Damola’s favourite work below.
FIFA 22 OOH - campaign tagline written by Damola, featuring Kylian Mbappe, Trent Alexander-Arnold, Heung Min-Son and more.
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Magnum, Summer 22 campaign - tagline written by Damola
Nike Air Max Day 2023 - Third Air Max Day zine - editorial copy and these one-liners by Damola
Born In London, With Something For The World, released in 2023. The first brand ad from House Captain: values, ''why'', and creative purview.
@damolastayup on Instagram
@houseccaptain on Instagram
www.linkedin.com/damola-oladapo
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Thanks so much for reading. Oh, and, BTW: Back yourself! Listen to my last interviewee, Sarah Tulej and do your marketing! If you’d like to feature on my newsletter, and enjoy (I’m told) a nice cathartic chat with your favourite career transitioner (me) then please, for the love of making us all feel a little less terrified, get in touch. Don’t be shy - everyone’s welcome here.
Gabby xx