Dream Big. Hustle Hard: Interview with Abadesi Osunsade.
Abadesi Osunsade was born in Washington DC and grew up in East Africa, before moving to the UK to complete secondary school. She is now the founder of Hustle Crew — a career advancement community for the underrepresented in tech, and NonTechTech — a mentorship community for non-technical techies, as well as author of careers advice book Dream Big. Hustle Hard. Abadesi also works on growth at Product Hunt / AngelList.
Previously, Abadesi was team leader in growth-oriented roles at Amazon, HotelTonight and Groupon — where she joined as one of the first Partner Managers and helped scale the department x 5 in her first eight months. Here’s her story:
Newnham: What is your background? What were you like growing up and how would your friends and family have described you?
Osunsade: My father is Nigerian and met my mother in her hometown in the Philippines in the 70s. Growing up I was precocious, bright and talkative. As soon as I knew what school was I desperately wanted to go. Every morning as a small child I became jealous as I watched my older brother and sister go to school while I stayed home with the nanny watching Sesame Street. To feed my growing curiosity and thirst for knowledge I would invent games and try to teach myself how to read the longest books I could find on our bookshelf to show my siblings that I was smart like them. I once read every three letter word in War and Peace. As the baby of the family, I was constantly teased and I would let it get to me and endeavour to prove them wrong. I loved art. I once sketched all my favourite cartoon characters from Garfield the cat and my older brother was convinced I’d traced them, he probably still doesn’t believe me! So my family would probably have described me as “annoying, loud and always seeking attention.”
Newnham: Can you talk me through your career to date and include some highs and lows? How did you get into tech?
Osunsade: I graduated with a BSc degree in Government and Economics during the recession which was incredibly traumatic. I had just finished my degree at The London School of Economics (LSE) literally one mark off a distinction. LSE is the type of university where you are ‘guaranteed a job’ after graduation, or so I thought. I had no inkling about how to break into tech / startups. My interest was piqued when I watched the Facebook film, The Social Network. I didn’t realise there were jobs where you could change the world for the better by creating new technology, where every employee held equity in the company and where you could even become a billionaire. I was sold.
Being at Groupon is a real highlight of my career so far. Forbes named us the fastest growing company ever. I became a manager of a large team at 24, a year before the record breaking IPO. To be on a rocket ship just as it’s taking off is much rarer in tech than the media makes out.
Lows for me are what led to Hustle Crew. I was working at HotelTonight’s London office in an incredibly patriarchal environment, devoid of inclusion. A place where male colleagues ogled at interview candidates’ instagram pages and touched my hair “because it was so interesting.” I was in a relatively senior position but constantly had my actions and opinions scrutinised and criticised. I quit with no next move planned because by the end I was being gas lighted.
Newnham: That’s unbelievable but it glad to hear you set up Hustle Crew to combat this… You wear many hats from community builder to author and founder — how important is it for you to have that variety and how do you manage it all?
Osunsade: I am the type of person who gets more done the busier I am so I enjoy having a multi-hyphen career and leveraging all my skills. I have always been a generalist and, for the first time in my career, society now accepts and celebrates people like me whose strengths are spread across a range of fields.
It’s important for me to feel challenged and keep learning and not waste any of my abilities. That said, it’s incredibly hard to manage everything I’m responsible for. I feel strongly about prioritising well-being and self care so I value quality time with my partner and friends, and quality time on my own doing things I enjoy. So I am becoming increasingly disciplined with who and what I give my time to (e.g. doing less volunteering than in the past, going for fewer coffee dates), and I also wake up early and do work on the weekends. I have ambitious friends and my partner also has lots of side projects so being close to people who are also busy all the time building and creating makes me feel like what I do is normal and I’m not missing out.
Newnham: What are some of your top tips when it comes to building a community?
Osunsade: Many founders are reluctant to put themselves front and centre of their community when they start out. I was exactly the same with Hustle Crew at the beginning. I think it’s because we identify so strongly with brands (not their founders / CEOs) and assume the same will be the case with us.
We might also be shy and not trying to be “that egotistical person”. In reality, the brands we identify with are literally decades old. They have had plenty of time to build trust. At the beginning, before a brand is trusted and recognised, it is the people behind the brand that attract an audience. So to build a successful community people have to trust you as its leader. You have to have domain expertise, or at the very least unbridled passion and enthusiasm for the cause you are building a community around. Find out what that is, and be bold and open about it, then watch like minded people flock to you. A community must add value to its members, so keeping a feedback loop open and consistent will ensure you are giving the community members what they need / want.
Newnham: Can you tell us about your book — who is it for and what will they learn from it?
Osunsade: The way university teaches students about careers is fundamentally broken. I went to LSE, an elite and expensive institution, yet had no clue about maximising my earnings, breaking into tech, or understanding compensation packages in the world of startups. As a woman in a patriarchy, I was completely unprepared for the additional challenges I would face when it comes to how I am perceived by the majority male leadership of the corporate world and how I am paid. So my book is full of all the key tactics and frameworks I wish I had had at the start of my career.
Readers will learn how to find roles that make them feel most fulfilled, how to navigate a complex and changing landscape and still come out on top, how to earn more and learn more at work. My plan with the book is for young women starting out to accelerate their careers and reach leadership positions — like being founders or in the C suite — much quicker than I have.
Newnham: As you know, women and POC have traditionally had a hard time in the tech industry due to it being overrun with white men. How have you seen it shift and where do you think the industry is headed?
Osunsade: I haven’t really seen the significant changes that I would like to in the nine years since I graduated. I have seen our vocabulary expand — we can now name things like intersectionality and patriarchy — but despite the overwhelming data showing the commercial benefits of having diverse teams, nothing is really changing. The Guardian published reasons FTSE 500 CEOs gave for having so few women on boards, my favourite response was “we already have one”. I think since change must come from top down it may be that we literally need to have more women and poc leaders for the industry to reflect society. I hope thats the direction we’re headed in. Communities like Hustle Crew, F equals, Ada’s List, Leap by Y Combinator, Black Girl Tech are all doing what they can to accelerate progress of women in the industry
Newnham: How do you think we make it better and more inclusive for all?
Osunsade: The people with the greatest power to make change here are the people right at the top of the industry — investors and founders / CEOs. All the tips and strategies are available for them to apply — noteworthy thought leaders here are Project Include, Paradigm IQ and Fearless Futures.
Being inclusive starts from day one. Investors and CEOs have to be thinking about representation from the beginning. It should be a priority, a core value. The first ten hires of a company should not be a homogenous group as far as identity. And if you’re already a mature company trying to change, ensure the most senior leaders in the company support inclusion and are devoting their energy and resources to fostering it in the company.
Newnham: Who / what inspires you and why?
Osunsade: I’m really inspired by Oprah Winfrey. She lives an authentic, spiritual life whilst still winning at capitalism. She is living proof that you can be a good person and be super rich. She’s built an incredibly successful business empire and continues to empower and uplift others, especially women. Plus she’s the only black woman billionaire.
Newnham: If you could give one piece of advice to a first-time founder, what would it be?
Osunsade: Sell a product or service that doesn’t require educating your audience. Hustle Crew launched as a career coaching platform for millennial woman. New user acquisition and retention slumped about six months into operations because our target audience couldn’t justify the £40/month subscription fee for our monthly coaching sessions. Now some people might say that’s really cheap but we work with a demographic that doesn’t invest in personal development. They might spend £40/month on a gym subscription, but that’s where they draw the line. That’s what made us pivot to B2B and offering everything to our community for free. I still wanted to work within career advancement and this is how I could make it work. TLDR: Work on something where there is an obvious need for it, and ensure it is an essential need vs ‘a nice to have’.
Newnham: Finally, if you could go back in time, what advice would you give to an Abadesi who was just starting out?
Osunsade: So many things! The first being confidence and self belief. I always considered myself confident but in reality I still had self esteem issues, particularly being an underrepresented person in the workplace. I would encourage myself to get mentors and coaches and be in a community that makes me feel confident about who I am and what value I can add in the workplace. I would also say to start something — it took me years to finally bite the bullet on starting a company. The sooner you start the sooner you learn what works and what doesn’t.
** This interview first appeared on the F = blog here **