Yolanda Lee on Finding Her Own Path and Building a Professional Community for Women

In this episode, we have Yolanda Lee, co-founder of Uncommon. Uncommon is a private leadership network for the next generation of female leaders in the nation. Uncommon is a private leadership network for the next generation of female leaders in Asia. Uncommon provides a strong and uplifting network, a personalized development roadmap, tailored courses and workshops, and enriching speaker series, all in one membership.

At 20, Yolanda rented an abandoned industrial warehouse in her hometown of Toronto and got artists like Daft Punk and Major Lazer to play there by messaging them on Myspace. She went on to intern at the European Court for Human Rights, graduated top of her class at Oxford and worked for Uber and Rocket Internet in Africa. We talk about what drove her to these different paths and how those experiences shaped her.

Towards the end of our conversation, she opens up about her motivation for starting Uncommon, what her personal experience has been in male dominated industries, why Uncommon is so important and what we, especially men, can do to help.

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Origin Story of Yolanda

  • 1:23 – Yolanda is from Canada. She’s born in the suburbs of Toronto, in a place called Scarborough.
  • 4:05 – She’s a Trinidadian. Ethnically her Trinidad is a pretty diverse place. Her family’s ethnic origins are Indian, that Chinese West African, and a little bit of Caucasian as well.
  • 4:59 – When you’re young, you’ve just so adaptive. Yolanda had moved schools quite a lot because her mom was very demanding of her educators. And so they would just kind of move schools super often.
  • 7:38 – There was such a big pressure on Yolanda’s education and she felt like the weight of everything, her parents were kind of sacrificing for her. So whilst she was rebellious, Yolanda still really understood education as a tool for social mobility.
  • 10:26 – Yolanda’s earliest forms of earning money came from babysitting. She and her brother also became lifeguards and swim instructors. Her first management experience was the now-defunct, retail brand called American apparel. Yolanda started with them when she was 16 and they had just gone from being a wholesale company to a retail company. She opened stores for them all over the US and Canada.
  • 17:32 – Yolanda had gotten to university in Canada for one year and then left. During that year, she still worked for American apparel at their store, which was opening in the university of town she was at.

Expectations on where she should come from

  • 19:13 – According to Yolanda, it sort of came from her parents. Her parents as well, like their understanding as immigrants, you’re just optimizing for stability. And so she thought if she’s going to be successful, these are the only paths that she can take.
  • 24:15 – Yolanda and her friends started throwing parties. She called 300 people there and they kind of became this mini booking agency. They started to do some big brand partnerships. And so ATD was sort of a site booking agency, events company, kind of promoter. And that’s really how Yolanda got involved in the music industry. She was hired by ITB, an international talent booking, which is one of the biggest artists booking agencies in the world.
  • 30:35 – At the time, they didn’t necessarily think about it. It was like, Hey, this is a cool thing we want to do. Let’s try it. It wasn’t necessarily thinking, overthinking it. You’ve got to under-think sometimes.
  • 31:09 – You can’t be afraid of the dragon in the cave. If you don’t know that there’s a dragon or you don’t know that the dragon will eat you, you’re just like, cool, there’s a cave. Let’s go to the cave. And when you’re young, you just don’t know anything about the dragon. So you’re just like, cool, let’s go. But as you get older, you’ve learned all about all these things and primarily learn about how, why things don’t work.

The reason why Yolanda stopped being part of the music industry

  • 32:53 – The freedom that Yolanda was so craving for so long, she got it. But then, she felt like she’s done with that. There was also like, it stopped being interesting and challenging.
  • 33:48 – She realized how important having an impact was. That’s also when finally she kind of became ready to go back to university. She had seen the world and was interested in making that better somehow. That is generally what motivated Yolanda. She also had a very clear picture in her head that she wanted to work in emerging markets.
  • 35:01 – Yolanda studied international development. She thought she was going to work at the United Nations. So she’s like going to go and save the world and work for like the United Nations or the world bank or something like that. She interned at the UN, worked at the European court of human rights. She was valedictorian of the undergraduate class and graduated top of her class at Oxford.
  • 38:07 – The diversity of Yolanda’s experience, whether it’s working in the music industry really helped her to see that’s she’s very good at taking systems from completely different places and applying them in other places, and thinking about problems in really different ways.

What Yolanda end up decided to do

  • 41:17 – What Yolanda did see while she was in Kenya was how incredible and the impact that technology could have. To see how technology transform lives.
  • 44:50 – Working in West Africa is where Yolanda really came of age as it was really baptism by fire. It was a really tough businesswoman and it was really tough in the sense of she was not used to that many friction points.
  • 46:13 – Learning to build that trust, not just trust in your brand, but trust in ordering things online. There’s a lot of market education. It was really about building Market trust across all aspects of the marketplace of getting restaurants to trust you, getting riders, to trust you, and getting customers to trust you.

All about Uncommon

  • 49:36 – Uncommon is a new kind of invite-only professional community for women in Southeast Asia. During the lockdown, Yolanda interviewed over a hundred women in Singapore and noticed some fundamental patterns that started to come up. She realized a lot of the tools that exist for building a network are fundamentally designed for men and not necessarily in the ways in which women want to connect, which is through shared experience through building relationships rather than something really transactional.
  • 52:35 – So it’s everything from peer coaching, exact coaching, they run programs. They have speaker series and workshops and the idea is that they can develop women according to their own kind of personalized goals, but in achieving their personalized goals but together, and you kind of realize that shared experience. Even though it’s individual, you kind of keep each other accountable and supportive through that community.

What drew Yolanda to do something about it

  • 53:45 – Throughout Yolanda’s career, which was challenging, she didn’t necessarily have that support. She just got tired about talking about this in the back channels with her female leader, friends. And she was like, this shouldn’t be solely bilateral conversations.
  • 58:55 – So many female leaders feel like an Island and they don’t realize that everyone else is feeling like that as well.
  • 1:01:40 – It’s really important to have a supportive crew. And it doesn’t just have to be women, who is the person who is going to be the everyday person that keeps you motivated. Who’s your person who’s going to give you that straight talk when you really need it. Who’s the person who will give you those technical skills that you need in your domain.
  • 1:09:21 – If you observe something, building it around that context can often be like, Hey, I observed this, like just wanting to check if you’re okay. Or like, what would be like a great way to support you in a situation like that? And framing it in that way can really help.