Women of Motley: Abadesi Osunsade, founder of Hustle Crew

15 MIN READ | by Ilana Lever on May 16, 2019
15 MIN READ | by Ilana Lever on May 16, 2019

Ilana, co-founder of Motley, sat down with Abadesi Osunsade, founder of Hustle Crew, the network for the underrepresented in tech, author of ‘Dream Big, Hustle Hard’ and all-round girl boss.

So, Abadesi, tell me about the early years.

I grew up in a multicultural home because my Dad was from Nigeria and my Mum was from the Philippines; two different cultures under one roof. I was very much an ordinary American kid in the suburbs, in an American public school, until my Dad’s job took my family to east Africa when I was eight years old. I went to an international school in Tanzania, then Kenya, then came to the UK for boarding school when I was fourteen years old. Having had all those experiences growing up around lots of different people and cultures, I think I took diversity for granted. I’d always thought, it’s so interesting to be around people with different cultures, languages and backgrounds. It’s something that I feel that I’ve always tried to find and look for.

Were you tech-obsessed from childhood?

Not at all. I did make a GeoCities website so that my friends and I could make a Josh Hartnett fan site. We were obsessed with Pearl Harbour (which is not actually a good film, I now think, but when you’re a teenage girl in an all-girls’ boarding school, you take what you can get). That was the furthest I dabbled in technology. It was very different building sites back then, you could drag and drop, there was Bebo, there was High Five.

At that age, I thought I was going to be an economist, because that was what my Dad was, and I grew up in a very strict household where your parents just tell you what to do. The idea of not doing something my parents had told me to was not culturally acceptable. Tech wasn’t something that I even considered. I’m quite a sensitive person, so I thought, if I’m not an economist, maybe I’ll be a philosopher or an artist. I quite liked the idea of doing something unregimented, an exploration of the self and humanity…But it’s easy to dream when you’re a teenager, and you listen to emo music all day.

And when did these dreams start to fall apart?

My first year at the London School of Economics. I was like, holy shit, this is really hard. I unwisely didn’t study Maths for A-level, forgetting economics requires a lot of maths techniques, and so I found myself surrounded by lots of really, really clever people, which no one warns you about before you go to uni. You think you’re really smart until university where everyone is just like you, if not smarter than you. Everyone was perfect, head boy, top of the class, I was like, I feel really stupid now, and I didn’t have the confidence to ask for help.

I think a lot of that is about being a woman in the patriarchy. Men are really confident and say things like, ‘I’m going to say something even though I’m not sure about it’, and as a woman, you think more like, ‘God, I think I’m so stupid, I might spontaneously combust’. So I very quickly realised, economics wasn’t for me. Why should I choose a profession that I’m struggling with? I should do stuff that I’m good at.

Meanwhile, I wrote for the student paper and did a few plays as part of the Drama society. I always enjoyed theatre, but having really strict immigrant parents, they talked me out of it, saying, ‘You can’t make a living as an actress.’

And then you graduated and recession hit?

Yeahhhh! Graduates of 2009. (fist pump, as fellow graduate). That was so soul destroying. During university, I worked in the Reiss concession at Selfridges, London is expensive and I needed the money. I remember all of final year thinking, I can’t wait to get a real job and quit this retail job. Then the recession happened, and I found myself taking on full-time hours.

I feel like there’s a sense of solidarity among people who graduated during that time because we know how bad it was. I feel like it’s given us a good work ethic because we’ve done really basic jobs a graduate wouldn’t normally do, but it’s also given us this hunger to be financially secure.

Did you have a career plan in mind?

I was always obsessed with having a career plan, but could never find it. I’m a control freak – I was like, I need a blueprint, I need a template, but it just never came. Graduating in the recession, the plan was to just get a job, and when I did get a job, the plan was to get a job that I liked; and you keep turning in all these different directions. I never had a calling. I feel to some extent now that plans are a bit of a myth. We have a tendency to tell stories. Yuval Noah Harari refers to that in his book Sapiens – that’s the essence of humanity, we exist in stories, and sometimes we get caught up in the story, we think our story must make sense. Loads of people I admire – their careers don’t make any sense but they’re still doing really cool things.

You’ve worked in loads of places. Where has most influenced the way you think?

My very first job in tech had a huge impact on me and what I wanted to do. Being able to work at Groupon one year before a record-breaking IPO – you know, $16b – was pretty incredible, because I’d never worked in tech, I saw the film ‘The Social Network’ and thought, yeah, let’s do it, I want to be a billionaire. And then I found myself in this company that was doubling in size every few months, and I was like, I didn’t know that could happen. We were growing so quickly, we were moving so fast and breaking things and making stuff up as we went along. I’ve not really had that anywhere else. Something about the fearlessness in which we worked, the openness in which we did it. I mean, it also came with huge drawbacks, no boundaries. Come in at 9am, leave at 9pm, go to the pub after work, get drunk, do it all over again. I would not have the energy to work at that pace now.

I learnt so much about how to grow a company, hire people, build out KPIs. I learnt from founders who had had exits or done cool things –  to be in the proximity of people who had done it means you learn things you just can’t learn from a book or a podcast.

Going back to your Hustle Crew days – what does hustle mean to you?

I was getting really annoyed by Tim Ferriss and Gary Vee – “Hi, I’m a heterosexual straight white man from a pretty good background, and here are my tips to getting rich while doing nothing.” That path is not available to so many people, including people like me. Hustle Crew was the idea of exposing the challenges that women and other underrepresented people face.

A lot of the advice that’s spouted out by universities and the media is most effective for a certain type of person, for the status quo, but if you’re underrepresented,  the truth is you are going to have to work harder to prove yourself, to find opportunities, to build connections, to get into networks. If you’re naïve about that, as I was, when I first got started, you’re not doing yourself any favours. That’s what the hustle meant. This is the truth, it’s quite ugly, however, there’s hope, let’s do good things.

What transformed your interest in diversity into the activist work you do now?

There’s this quote from Anais Nin who wrote erotic fiction – she’s a badass – and she wrote, ‘Good things happen to those who hustle’.

In my career, I had never thought about the hustle element of success. I’d thought, I’m going to keep my head down and work pretty hard and people are going to see that I’m doing a great job, and good things are going to happen to me. But that wasn’t happening. And people who weren’t as good as me but were good at talking – mainly were men, would be doing better, particularly in the context of my peers.

It got to one specific point when I had reached the most senior part of my career – I’d been headhunted into a leadership role, and this weird thing was happening where I would propose an opinion based on what my clients had said or insight that I had and I would be consistently challenged. I’d be like, why do you think I’m wrong, the data is here, this is what clients have said, there’s something else going on. What’s going on was discrimination. And when I challenged people on that and said I feel like I’m being discriminated, I became a pariah. Even women in the organisation were like, ‘He’s not creepy because he makes me sit on his lap, he’s just flirty,” and I just thought, wow, this problem is so endemic that we can’t even see fucked up stuff when it’s happening right in front of us.

What do I do now? I knew I’d be a lot happier working in tech and in start-ups if there were more people like me, and if the things we’ve been through come to the surface and don’t happen again. It was so common for people saying sexist things, racist things, and not being checked, so they just continue to do it. I started for selfish reasons – I thought, I can quit tech, but I like tech, so what will it take me to stay, I’d like better representation.

How do you help people learn about their own biases?

It’s so difficult. Even if you teach someone, they’ll make mistakes. When you have a different identity to someone, you have decades of history that are variant from your own. You don’t know the trials and tribulations that have passed down through generations. I was at dinner with a friend yesterday and one of our guy friends asked her, are you going to be at an event tomorrow, and she said I’ll be there, and he replied hashtagmetoo, and she said, don’t say that, it’s not a catchphrase, it’s a movement about women facing sexual discrimination everywhere.” That’s what a microaggression is, it’s trivialising trauma.

Anything about the hair of someone of a different race than you is probably a microaggression – is that natural, is it a wig, how did you grow it, do you curl it every night before you go to sleep? Just don’t ask.

What do you think is the biggest no-go topic that women still struggle with getting out and talking about?

I don’t feel like there’s one topic that stands out, it’s rather the way we feel that there’s no space to discuss. We haven’t been able to create a positive, healthy space for discussing emotions in the workplace and I think that’s why mental health is such a big issue now. Sharing positive emotions too is important, especially when women get penalised for celebrating their achievements. Study after study shows when men go, look at this great thing I did, and people say, Paul is great, and when a woman does this, people say, Paula is so full of herself. We need to create spaces where you don’t have to be ashamed of your emotions.

What was your must-read book of last year?

If I’m honest the books that really changed me last year was Maya Angelou’s autobiographies – I read them back to back, eight in total. I think we have so much to learn from people and their stories. What I loved about Maya Angelou was she was so unapologetically herself, and she gave zero fucks about anything.  She’s so incredibly self-aware and the way she describes that journey of self-awareness, the relationships that went wrong, what she learnt about herself in them – she bares all, and in such a poetic way. She had this ability to tap into her inner strength, and I think there’s a lesson for all women in us.

What good examples are out there in the world of business that are relatable to, or written by, women?

I agree. I wrote my book, ‘Dream Big, Hustle Hard’ because of this. When I want to find a book about succeeding in the tech industry, none of them are written by women, and not only that, none of them are written by multicultural women.

I really like ‘Mindset’ by Carol S Dwek. It helped me move away from this binary idea of success to a more nuanced style of thinking. And I was listening to Hilary Clinton’s book on Audible. It’s humbling to think, whether you like her or not, her career is pretty impressive. She could do all of that, get to that point, and lose to someone so ill-qualified for the role. What a strength to pick yourself back up, there’s something anyone can take away from that. She talks about misogyny and sexual discrimination and the patriarchy, and how she felt that in such a tangible way. 2019 is a year of reading only female authors, for me.

Can you tell us about a piece of art that has really inspired you?

I love film as a form of art because I love the escapism you get for 90 minutes. I saw this amazing documentary called Shirkers, by an Asian female film director. It was a story of a film that she made and lost. It’s incredibly honest and also shot in a beautiful way. She’s a fan of directors like David Lynch and French New Wave, and she brings a lot of that into the film. She mixed in New York clips with collages with close-ups of her journals, sketchbooks and diaries when she was young. It was like a scrapbook done in video form. It was such a delight. When I finished it, I was like, I love it, and then it had 100% on Rotten Tomatoes, so everyone must agree.

What do you see as the future of art and tech combined?

We’re living in a time right now where we’re shattering so many boundaries. We as humans don’t know ourselves that well, and we’re discovering things about ourselves all the time.

I see some people always having a nostalgia for the past, shooting in film, creating with primitive materials, because that connects with them. It’s worth people still exploring all the things that technology can do. But I hope that as individuals we will always still value art, even if there’s a way to automate its creation because there’s some part of humanity that’s always felt the need to express itself. By virtue of doing that, it makes us human. Every culture in every time has had something that’s like art, and I hope we never lose that. I think technology will help us evolve that and make it more accessible.

I don’t think capitalism in its current form gets optimised for art. Art gets packaged and commercialised and pulled away from what it was intended to be for. It does make me sad that there are so many people that are excluded from art, and that the art world itself is so exclusive. I don’t like that I go to art galleries and the descriptions are so alienating. For me, I look at art because I’m trying to understand what they’re trying to say, and because technology isn’t a person, I’m not interested in what they’re trying to say,

What are the things you’d love people to write about you?

I want a sauna that I walk to naked in my kimono, with a glass of chilled champagne. Is that weird? I want that now. I want a goat. Maybe two or three or four. Do you know AJ Tracey? He has two pet pygmy goats. I’ve heard about pools that are indoor and indoor. I’m just listing things I want now.

Who’d play you in a film of your life?

People always say I look like Yara Shahidi,  the actress in Blackish. Or Chanel Iman. Or we could mix it up, and make an avatar of me because tech will be able to do that by then.


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