Hustle Crew and Abadesi Osunsade

Founder and CEO explains how she pivoted to a B2B model, what she learned from launching a membership product last year, and highlights the challenge of selling anti-racism products.

Abadesi Osunsade founded Hustle Crew in 2016 from a very personal experience. As the only Black person in her office and the only woman at her senior level she experienced microaggressions that made it difficult for her to be productive. That’s when Abadesi realized, “if someone with my credentials and my authority can face that type of sexism and racism, what is it like when you don't even have that authority and status yet?” She founded Hustle Crew to ensure other people don’t have this experience. She grew the company slowly at first, using up her own savings, then shifted the business model to B2B, and a year ago introduced a membership for individuals. These changes helped the business growth accelerate and they are on track to be a seven figure revenue company next year. 

In our conversation, Abadesi talks about:

  • The microaggressions she experienced as the only black person in her tech office that drove her to start Hustle Crew

  • How she pivoted the business model when she struggled to raise money for the initial community-centric product 

  • The challenges of selling anti-racism products to businesses because part of the sale can be interpreted as an accusation

  • How in the wake of George Floyd’s murder they built and launched a new membership product in a single weekend to harness the energy of the moment so that the momentum and accountability would not be lost

My questions are in bold; this interview has been lightly edited for clarity.

Let’s start at the beginning. Can you give me a quick overview of how Hustle Crew started?

Abadesi Osunsade: In 2016, I was working at a startup in London. I was in a growth role helping launch the app in new markets. I was the only black person in that office and I was the only person at that level of my identity. There were a lot of things which were innocuous and completely innocent to my teammates, but which were super disruptive to me. Very little things which maybe now are a bit more obvious because on a macro level, the conversation has moved on. So, for example, touching my hair without my permission or Instagram stalking interview candidates I was bringing in and deciding which one they'd try and ask out on a date. It was really difficult for me to be productive in an environment where I felt objectified and where I thought women like me were being objectified. I never found a successful way to communicate this message to my teammates or to our co-founders back in San Francisco. So I decided to quit, but that's when I became obsessed with this problem. Part of me felt if someone with my status -- at that point, I'd worked at Groupon, Amazon, and I was headhunted for this role -- If someone with my credentials and my authority can face that type of sexism and racism, what is it like when you don't even have that authority and status yet? And how do I make sure that other people don't face the same problem as I do?

So that’s how Hustle Crew first started. The first iteration of Hustle Crew was a careers community for women and other underrepresented people in tech. What I wanted to do was help them do better than I did. I wanted to give them tools for navigating a challenging conversation, like what happens when you face a microaggression and how do you productively take that up with your line manager and your boss? Now, I really struggled to raise fundraising with that concept and that idea. I was bootstrapping it myself and I very soon started running out of money. I was realizing it is hard to grow a B2C community on your own, especially if it's behind a paywall, so that's when I started to move towards a B2B model. Around this time, companies were already happy to invest in "lunch & learn” training and workshops. So I pivoted Hustle Crew to focus on equipping employers with the tools to be more aware of what creates micro aggressions and things like that. That’s the business model we've been with since the pivot, until we launched Membership.

So the initial product was a community for women and underrepresented people in tech to share resources and support each other?

AO: It was just the community and gave you access to content that was created by myself and other contributors. The content was focused on the unique challenges women face. For example, like how to negotiate when you're the only woman on your team and you're feeling a lot of imposter syndrome. We also had workshops that were focused on career skills. Things like building confidence or writing your resume for your next job. The payment plans were £40 per month, or £60 or £80. Depending on how much you paid, you’d also get one to one support from me. I was actually doing one to one coaching with people and creating accountability with them. I was also hosting all kinds of events. We'd have a brunch club every month and a careers clinic. So those were all the things I was offering, but I had an expectation that it would be easier to acquire customers. I soon realized that it was quite expensive to convert folks into paying customers and it was also really hard to retain people. I had originally thought the lifetime of a customer would be at least 12 months, but what I saw was that after three or four months, people were like, “I don't need one to one coaching anymore because I've landed that new job” or “I've asked for that pay rise and I got it.” So I was like, oh, this is too effective. What do I do now? That's when I thought going directly to businesses would be great because you can start with the engineering department, then go to the product department or do something just for the women in sales. So switching our focus to businesses has definitely helped us get more traction.

How long after launching Hustle Crew did you make that switch to the B2B model?

AO: So I joined an accelerator called The Family, based in Paris, but they're pan-European and when you join an accelerator/incubator, you're only in that environment for a limited period of time and they really are trying to get you to the point where you're investible. They were looking at my metrics and they're like, you need to switch to B2B because then you're going to start seeing all of your metrics upticking, you're going to see an increase in monthly recurring revenue, and an increase in how many products or services you're selling every week. I launched Hustle Crew in September 2016 and joined the incubator in Spring or Summer 2017. So eight months into the journey, I'm now abandoning that B2C model with a paywall. I completely redid the website and switched all of my conversations to talking to tech companies and tech teams.

Let’s talk about the Membership that you launched a year ago. It seemed like it was a response to the murder of George Floyd and the upswell in people looking for resources to change the enviornment in their offices.

AO: 100%. I think my intuition was always that people within any employment ecosystem want to hold themselves accountable to being the best team member they can be, but it's so hard to do that because we're usually not incentivized to do that in our role. Just reflecting on my own career, when I was a key account manager at Amazon, I was incentivized to hit targets. When I was launching apps for HotelTonight, I was incentivized to get the best conversion rate for the city that I was selling bookings in. What I realized around Summer 2020 was that a lot of people in the height of Black Lives Matter, going to the protests, posting on social media, were already aware of how the news cycle works. They were already aware of how business priorities work. A lot of people, not just in the Hustle crew community, but in the wider tech ecosystem, were communicating this fear, this risk, that the momentum would be lost and the accountability would be de-prioritized. There was an energy of how do we keep doing the work? That's when I realized the timing was right to bring back a membership model, but depart from the original vision of content that speaks to women and underrepresented people. Instead, based on what we learned from all of these years working B2B, we need to create content that teaches employers and people with positions of authority and power and leadership within organizations about the actions they can take to model that behavior across their organization and also to stop being the blocker to greater diversity and inclusion. 

So that was the motivation behind launching the membership. It was always on my roadmap, but it just never felt ready. I just never felt ready. I would even say that we were only just approaching product market fit with the standard workshops. If you look at our sales graph, we have spikes at certain times of the year. Let's say, when gender pay gap reporting came out in the UK, boom, we had an influx of demand, but it was by no means consistent. I would compare ourselves to similar businesses, outside of diversity, but selling training and workshops, and it was clear we were not where they were at. But when all of that stuff started happening in the news I could sense this energy. We were putting out webinars at the time and we did a webinar called “How to Discuss Race at Work.” We had over a thousand people sign up in 48 hours. We did another webinar called “Understanding Bias.” It was the first time we'd done a webinate that was ticketed and people had to pay $20. We made $15,000 in ticket sales in 72 hours! I was like, holy moly, now is the time. My team and I literally built the membership platform over a weekend. We went to the marches and then we came back home and just built. Come Monday we launched. It was one of those things where the timing made it super perfect to launch.

I love that you built it over a weekend and just launched it. You mentioned that it had been on your roadmap but you hadn’t been ready. Can you tell me more about why you had thought you weren’t ready? 

AO: So I've noticed that a lot of subscriptions or software, especially if you're going B2B, you can usually determine which part of a budget that's going to come out of. When I first started Hustle Crew, as a B2B service of diversity workshops, I often struggled to identify which part of a company’s budget it would come out of. Is it the learning and development budget? Or is this the marketing budget because they can use this as employer branding and say, hey, look at all this diversity work that we do, or is it going to come out of an individual department head’s discretionary budget? That was always really hard for me to identify. 

When it came to launching a membership, that's where I got stuck again because I wasn’t sure what the individual motivation would be for investing in the membership. Is this coming out of the budget that people put aside for any online content, like a subscription to the New York Times? Or is this going to come out of the budget that people put towards learning, like, instead of Coursera, they invest in Hustle Crew? That made it difficult for me to decide how to launch and market a membership because I didn’t know who the personas were that we would be building for, if that makes sense. But when everything happened in 2020, I realized I didn't necessarily need to have all the answers because it could vary organization to organization or individual to individual. All we had to do was launch, get it out there, and then based on the data like who's actually buying it, who's actually keeping it, who's actually purchasing multiple subscriptions for people in their teams, et cetera, that would help me find the answers to the questions that I was trying to answer by research instead of real life data.

Let's talk more about the past year. Now that the membership is launched, how are people using it? Has there been anything that has surprised you?

AO: So I wrote this Google doc before I launched with all of my goals. You know, classic maker stuff. These are my goals, these are my red lines. If we don’t hit these targets we’re pulling the product and so on. The goal was to get to at least 200 paying members by the end of month three and ideally 500. I remember saying, if we don't have at least 200 paying members by that point, I'm going to pull it because it is expensive to maintain. But what's really interesting is we got to month three, we were hovering around 150 members, and I just decided to not kill it after all. I was reviewing all of the feedback that was coming in from our members and it kind of reminded me of the first B2B clients we'd ever secured, which also took a really long time. There was just such a delight and a gratitude for its existence that I was decided, you know what? Maybe I just need to wait, just like I waited at the start of launching our B2B workshops.

Right now we have 179 active members and I would say about 75% are monthly subscribers, 20% are annual, and the last 5% are lifetime, meaning they paid a one time $450 to access everything as long as we exist. I kind of put up the one time membership just because everyone I spoke to who had subscription services said you gotta put that up for someone. Someone's elasticity of demand is going to be up there. And, it worked! 

Anyways, I launched the membership 100% to capitalize on the momentum and the attention that inclusion work was getting at that time, whether it was a founder or a recruiting manager. There were all these people that wanted to learn more about ableism or anti-racism. We need to get this product out there so we can convert this attention into revenue. But it was so interesting to watch the new user growth dive as the year went on and now, I'm not going to lie, it's moving at a glacial pace. I think there are a number of reasons for that. One, the timing has moved on. But secondly, we just don't have product market fit yet. At the beginning, it was good enough for us to just say, hey, sign up to our premium content for free weekly resources, videos and workshops. I think people really liked the idea of being able to attend exclusive workshops and webinars that would teach them how to navigate conversations around pregnancy discrimination or all of these things that can happen in the workplace. But when it actually came to people showing up, we noticed that a lot of people would reschedule or cancel on the day. About six months in we sent out our first feedback survey and customers said, “I want to learn, but sometimes the workshops are so interactive that I feel intimidated by the content and I feel like I have nothing to contribute” or “I feel like I'm too early in my learning journey to even be in that space.”

There were people who had maybe attended a few workshops then were kind of like, “whoa, OK, I need to know more before I show up to events.” So that feedback meant that we started to tweak our workshops. We realized people were not stepping into the space as the diversity officer of their company. They're stepping into the space as just an engineer that wants to know a bit more about this. This meant that we needed to adapt them in terms of, like, how you're going to gain the knowledge and how you're going to apply it. Because we were coming into that space with an expectation that everyone was showing up so that they could do the work that Hustle Crew does in their organization, but actually a lot of people are like, I would like to maybe one day, but I can't manifest the energy until I feel confident about the basics of stuff.

The second thing that we couldn't have anticipated was where our members would fall across the world. We are based in London, but we have a heavy U.S. presence just by virtue of being in tech. I wish we had run that customer survey a lot sooner, because we learned that more of our U.S. customers were on the West Coast than the East Coast. So we now run our events for each time zone. We do a UK time, then an East Coast, and then also West Coast so that more people have an opportunity to be live, in a space, with other members and our consultant. 

Another thing that we learned is that anything behind a paywall has to be teased and people need to be able to test drive it. So we are just about to introduce a free trial so people can explore the resources, come to some of our community events, our meetups, our webinars, and see whether or not they’re going to be useful to them and worth the investment. 

The final thing, which has been really, really interesting and this is where I want to focus our product development going forward, is that we now have organizations that have made the decision that instead of hiring a diversity officer they're going to invest in Hustle Crew membership for the whole company. Just last week, we had a small but successful digital creative agency invest in forty memberships. They want to spend the next 12 months seeing what the impact of 40 members of staff receiving our newsletters, our videos, our podcasts, our community meetups and webinars. They want to see what effect that will have on their goals, for example, increasing representation of women and people of color that are being hired and also increasing representation in all of the campaigns that they put out with their clients. So now that I can see there's a use case for organizations who want to build their inclusion muscles, but not by just outsourcing it to one person, instead by having a really immersive experience for the entire company, it makes me feel like this is a direction we can go. We can show companies that it's a perfect offering and we can adapt it to their individual goals.

Wow, that seems like a perfect compliment to your B2B workshop product. How are you going to balance the two products going forward?

AO: I think one of the things that every maker should do is zoom out and remember what all of the products you've made sit under. What's the umbrella of your brand? What's the umbrella of your mission? What are you actually moving towards? And from day one, Hustle Crew has been on a mission to make the tech industry more inclusive through talks and training, and we're still doing that. So the way that our memberships fit into that is by acknowledging that the journey to be more inclusive is exactly that. It's a journey. It's not just that one off action, that one off workshop, that one off webinar, that one off book. It's about replacing non-inclusive habits with more equitable habits. The way that you do that is by staying aware of what's blocking inclusion, what's blocking equity, and staying aware of your biases and what is happening on a systemic or societal level to slow down the progress of your goals.

What we are trying to do a much better job of is to show companies that we have a suite of services to help them along that journey and keep them accountable to doing the work of that journey. So I think now the perfect customer journey for us is someone like me, an underrepresented person in a tech company, finds Hustle Crew through, let's say, our Instagram or LinkedIn. They find the free career advice super compelling and actionable, so they recommend the training we offer to their line manager. That line manager comes to Hustle Crew's website and sees that we have a recommended program, which is a two part training of understanding bias and then a scenarios based workshop to help companies foster inclusion in recruitment, in marketing, in the language you use in programming. That line manager invites their peers or their team to our training. At the end of the training, they say, “Wow, I've learned so much and it's been so great to be in this space learning and discussing, but how do we keep going?” That’s where our membership comes in. They can keep coming to our incredible community events and keep accessing all of the knowledge. Now that team is immersed in our ecosystem and they’ll evangelize the value of our work to the broader organization. 

We're in the process right now of connecting the dots a lot better across all of our products. We haven't done that very well on our website. We're not telling that journey and we're also not doing it that great on social. But now that everything's starting to fall into place and we see validation from the way companies are investing in our services and products, we can see that we've got a good case to make to others. So that's where we're moving towards, just connecting the dots a lot better.

Can you tell me about your customer acquisition strategy? Is that customer journey, where people start by finding you on social the most common way that you acquire new customers or do you have a sales team reaching out to businesses?

AO: We are incredibly fortunate that we are growing year on year. We became a six figure revenue company last year and if we keep growing and maintain our MRR (monthly recurring revenue) we could be a seven figure revenue business early next year. I’m so happy about that. But to answer your question, it’s crazy because we don't do sales. It just doesn't work. It's so hard to sell anti-racism products because part of that sale almost includes an accusation. It’s hard to say, “your culture doesn't look that great, why don’t you come and talk to us.” So what we found is that content marketing is the way for us to talk about the problem we're solving, the unique way that we're solving it, why it's important to us, and share the community stories that validate our training content and give us the insights. Content marketing is also a way for us to separate ourselves from our competitors, because there's actually -- and I think it's a great thing -- so many people doing the work of making cultures more inclusive and helping people understand the diversity problem better. That is amazing, but it also means it can be really hard to cut through the noise. So with content marketing we can tell the stories of our community our way and we can talk about the problem our way. That has really helped us grow, because when I think of all of the people that we compete with now, incredible organizations, but still companies like BBC, Stella McCartney, and Facebook will pick us. It’s pretty friggin cool that these global brands, these multi billion dollar companies pick us. A big part of why they pick us is because of our branding and the content marketing that we do. We have a very clear message and a clear purpose. We're community driven, always have been, and always will be. That adds an authenticity to our work that becomes really hard to compete with.

I love that community driven approach. My last question for you, a lot of entrepreneurs struggle in that first year as they try to find product market fit and the buzz from the launch has worn off. How did you manage to stay motivated and focused after the excitement of the initial launch?

AO: All founders have to accept that timing is so important. I started Hustle Crew in 2016 before we were comfortable talking about racism as a systemic problem. A few people were talking about it, but it wasn't something that was widely accepted. Five years later, no one's arguing that fact. It's really, really important for founders to remember that. Sometimes you need a macro shift for things to really click into place and then you have a choice to make, are you happy to adapt what you sell to wait that out or do you just put it on ice and move on to something that's relevant for now and revisit that topic later? Both of those choices are completely OK and completely valid, I think for me, because Hustle Crew started from a personal experience and had so many personal sacrifices, bootstrapping, using up my savings, saying no to holidays at the pubs. I was just incredibly stubborn. I couldn't let it go, but I wouldn't necessarily advise that it could have been very easy to just put it on hold and revisit it later.

The more you believe in an idea the better. This is why people like Paul Graham, an incredible genius in the startup world, says, “do something that solves the problem that keeps you up at night.” If it is that close to your heart, you have that conviction to stick it out and you have that conviction to stay with it.

Where can people go to learn more about you and your business?

AO: They can go to my Twitter. That's probably the best place because I'm the most active on Twitter. And also, the Hustle Crew website.