Episode 91: Sheryl Thai – Who run the world?


All Xero Gravity episodes

Hosted by Elizabeth Ü

The founder of the League of Extraordinary Women, Sheryl Thai, spends her days bringing female entrepreneurs together. Her mission is, and always has been, to create a space where women can authentically connect, share their success, share their failures, feel inspired, and above all, feel solidarity that there are women out there going through similar shared experiences.

The League is also a place where the word ‘networking’ is prohibited, and any kind of card-swapping is a definite no-no. It’s about women supporting women, and everything that comes along with that. With almost 80,000 followers on Instagram and a keen following online, The League has now reached a point where Thai can let her first business - Cupcake Central – self-run and financially support her while she works full-time figuring out ways to make female entrepreneurs lives that little bit richer.




Corporate realities

It was during her five years in IT as a management consultant for a large US firm that Thai really started experiencing gender discrimination in the workplace.

“At the time I didn’t feel the glass ceiling, but looking back I’ve realized I was being discriminated against. It was little things, like on Friday nights when the male management team would go out for drinks at a whisky bar, and I would think, ‘Why do these guys get the opportunity to mingle with the senior managers and directors when I can’t?’ I was often one of the girls who would go along, and I believe that was why I got my promotions. I knew from a young age it wasn’t what you knew but who you knew.”

Thai considers herself lucky, for being one of the women who went along with the ‘boys club’ to an extent, but really felt for the women who missed out because they didn’t. Eventually Thai called time on the dog eat dog corporate world and went off to start her own business.

The League, pt I

The League of Extraordinary Women emerged from not only things Thai experienced while working in the corporate world, but the time spent feeling extremely isolated when Cupcake Central was in its early growth stages.

“Seven years ago back home in Australia it was unheard of for female entrepreneurs to start a business. I was going through really tough times and didn’t have anyone to talk to. I’d get close to a nervous breakdown every few weeks.”

After reaching out to networking events, Thai quickly learned they were loaded with sales pitches and primarily male-dominated, something that prompted her to widen her search.  

“I wanted to find someone who got me. I thought ‘surely I’m not the only one in the world feeling like this?’ So I went out and met a couple of women like me who had their own businesses, and we decided to catch up for breakfast every few weeks.”

It’s at this point that the penny dropped, and Thai realized other female entrepreneurs were who she needed to be around.

“We were being honest with each other and sharing the stuff we normally don’t get to talk about, because we would be trying to hide behind the success we should be showing people out there.”

After a number of successful breakfasts with fellow female entrepreneurs, Thai had the idea to host a larger event, post it to Facebook, and see who turned up.

And so The League began to grow.

Why just women?

“When I met these women we felt an energy we hadn’t experienced before. The magic comes from us supporting each other. We were much younger entrepreneurs, mostly in our mid-twenties, and found women in older business groups were very guarded. No one really wanted to talk about how they got to where they were or what they learned.”

League events are carefully thought out, and cater for those deep in a startup, right through to those who are still toying with the idea of starting a business. The carefully chosen speakers aren’t allowed to give advice, instead, they’re asked to share their greatest successes and their messiest failures, something Thai says creates a space for the walls come down and people feel comfortable in their vulnerability.

“We run these events in a way that allows everyone to be involved. If someone who is introvert doesn’t want to talk to anyone, but comes along and listens and is inspired, that to us fulfills our mission.”

Networking, networking, networking

Fast forward to August 2016, and Thai found herself at more networking events, this time in San Francisco.

“I would walk into a room with 300 men and 10 women. There was a frustration that came from not being able to form meaningful relationships, and sometimes it could come across as aggressive because you feel angry.”

But she doesn’t let the anger take precedence, saying “It’s easy to be angry at everyone, but at the same time that isolates you and other people.”  

“I try to find the fine line between being assertive and confident. Eventually, it will stop being ‘oh, you’re a woman,’ and become ‘oh, you’re a smart person who’s passionate about what you do.’”

Old school norms

“I met an interesting capital-raising founder who told me the track record for VC-backed companies are usually white males who have gone to ivy league schools, so if you’re not part of that realm it’s hard to get funding,” Thai says.  

“If they’re banking on a company that can make them money they’re going to look at the track record, and this is where bias starts. For me, the challenge is ‘how can I break through that, make myself heard, and prove I can build a company worth investing in.’”

Who to pitch?

“To be honest I had no idea. I didn’t know about angel funding, seed funding. I started with a big vision of what change I wanted to make. I’ve known since I was a child I wanted to change the world. With The League I had the big picture thinking how can I change the lives of women and support them on their journey? It sounds corny but I feel like I was born to do this, so I started thinking about what it would look like if I had no limitations, and how I could use tech. I knew scalability comes through tech, so I had to use that to create something that could scale worldwide.”

What were you thinking with scalability? Financial, etc

“Definitely impact. I’m a firm believer that if you’re doing something with passion and purpose, the money will come. I knew VC’s want to make money at the end of the day, so I worked backwards and thought if I want to make a global impact in the shortest amount of time, I need to go down that route. I knew every year we didn’t have a solution to connect female entrepreneurs.”

Making money from meetups

The League’s current revenue model is a recurring subscription, where subscribers are charged $12USD per month. Then there’s Find Your Five, a separate branch of The League, where Thai matches women with five others who she believes they could benefit from connecting with.

“I believe the saying that you are the average of the five friends you hang out with the most. We’re curating these connections based on the stage these people are at in their business,” she says of the app.  

“At the moment it’s very minimal. I hacked most of it together in a week. I wanted to do it as leanly as possible and see if it worked. We used our community and asked a bunch of questions, and within a week 130 people signed up. The algorithm was me, and on a spreadsheet I would match them up. It took me days to look at what people needed, then create all these little meetups together. Can you imagine matching six women together, who are all running their own businesses? Finding a time and day they were free, then getting one to organize a cafe was really challenging.”

Selling feelings

Still testing the current model, Thai has completed three rounds of Find Your Five since October, and has been pitching to investors to fund an app. It’s this search for the right kind of investors that has proven difficult for an app with little hard data to present.

“The League has been around for five years and we’ve tried every model under the sun to monetize and grow the company. I fund it myself right now. The costs are covered, but I work for free.”

So how does Thai pitch to investors? Well, there have been a sea of case studies compiled over the years, then there are surveys and net engagement scores. If an investor isn’t interested based on that data, Thai knows they aren’t right for The League.

“I’ve realized to be true and authentic to myself when I pitch. I just need to connect to what I’m saying, what my values are and what my vision is.”

Watching the magic happen

Capital-raising struggles aside, Thai says when she sees the impact The League is having, she knows it’s what she’s meant to be doing.

“Creating a startup isn’t fancy. I could sit back and live off of what Cupcake Central makes, but something inside of me has always wanted to do this. It’ll keep me awake at night if I don’t. The little voice in my head is annoying, but it drives me everyday to work on something that might fail and go nowhere, but I just keep doing it.”

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