Growing up in Hong Kong, Cleo’s mother wanted her to become a lawyer. It was respectable and a safe professional path. Besides, her parents were both working professionals, her mom was a lawyer with the Hong Kong government and her father was a medical doctor.

By the time she was 16, and about to get into the university, she had also grown on a mind of her own, and in her mind, a legal or medical career was not in the picture. “I wanted to be able to define my own path. I was always curious about business, but knew nothing about it.”

“I felt there was something out there that I could do that would probably be more interesting and be more fitting for me.” That fight to reject every single offer from UK universities to study law lasted for 2 years before finally, against her family’s wishes, she started off on a different path.<

Her first big venture. “That was [probably] a first big moment for me. Big leap of faith, I guess, and making a bet on myself ” Like diving off the steep side of a cliff dressed like a bungee jumper but clearly without the emotional support that is the safety harness.

Finding Uber. Finding China.

In 2013 Uber launched a Shanghai pilot as part of a wider China entry strategy. Other cities soon followed and the business took off, ultimately setting a record of Uber’s first 1 million trips in a week in Guangzhou. That figure grew to over 4 million weekly trip bookings in just two years in Guangzhou . Cleo was the Guangzhou General Manager.

So fast forward several years after Cleo won the fight to freely pursue a naive passion as a business student, she got hired to lead Uber’s entry in Guangzhou, China. Entering any new market is always going to be tough. Entering a new market with completely different business dynamics like China is a different level of tough.

“I was really just looking for a learning experience. In the end that was way more than I had expected and a really meaningful experience personally.”

China was (and still is) home to hundreds of millions of urban commuters. As General Manager, Cleo had to deal with government friendly hostile competition, and the general fast-paced nature of work in China. Ride-hailing is one of the toughest 21-st century business models to crack, and in China, that was reinforced by the fact that Uber was competing with not just anybody, but with Didi.

Where Uber relied on disruption to thrive, Didi was the exact opposite. It’s business was built on the back of the status quo. Uber needed drivers to sign up, Didi simply connected riders to already licensed taxi drivers, operating as a sort of government taxi app. It even helped city governments manage traffic lights in some areas!

Didi had also started operating in China a good one year before Uber’s experiment started. So how do you grow a business in a new market where everything is completely different?

You become Experimenter-in-Chief.

As it happens, in China, you will have a lot to learn. Uber’s early experiments helped the company realize that onboarding users who needed to validate credit card information before opening an account was a major roadblock. “So we needed to integrate with Alipay which was additional work on the engineering side. And then due to the firewall, Google maps clearly didn’t work in China, so we had to invest additional effort to integrate with Baidu.”

Cleo describes some of their earliest tactics as throwing things at the wall to see what stuck. 

“We had to be very creative around doing stunts that didn’t cost very much money, again leveraging partnerships with bigger brands and coming up with real hacks like partnering with a mobile game development company to create a viral mobile game that people played and shared on their WeChat which basically gave them promotions.”

Bring a war chest and some thick skin

Ultimately, Uber sold its China business to Didi, but having those first crucial resources to experiment, put out the constant fires, and hold up against blindsiding regulation helped them gain substantial market share (in 2016, China accounted for more than a third of Uber’s global business in weekly trips.).

“We had to be relentless, we had to be very decisive. Within 24 hours of ideation, we would already start to execute. That was what was needed to keep pace and also to gain market share at the time.”

You also need thick skin. Cleo’s role as General Manager was a very public-facing one, which meant, dealing with the city’s government, the press, and responsibility for tackling a litany of what you could mildly describe as black-hat guerilla marketing – ghost accounts planting fake cases on Wechat, accusing Uber drivers of harassing passengers, smear campaigns, or even drivers faking trips to collect on Uber’s subsidies. “We had a fire pretty much every week that we had to deal with while still trying to scale the business and hire the team and grow like 10 percent every week so it was just very intense.”

Wherever you are, be all there.

Every city is different, and relationships are important. What this essentially means is that you will need to be on ground, and with people from that ground. “ I think for any company looking to go into China, having a localized project management team would be essential and also would enable you to iterate faster,” Cleo says. She adds that eventually, Didi was able to catch up to Uber, as they had a more localized context.

In China, “There’s no such thing as dipping your toes in the water.”

Moving from operating to investing

“I started out in consulting, traded stocks for a while before going into operations, Angel investing felt like a good way to combine everything, and now VC which feels like a great way to leverage everything.”

Cleo is now Partner at Stride VC a London and Paris based VC firm that backs early stage founders with a clear vision and bold prototypes they are already working on.

Carrying over operating lessons

You would expect operators who back founders to have more nuanced insights and a bit more empathy. Here’s some of what Cleo believes are the important lessons and skills she has carried over from her time as an operator.

1. How to communicate what you know with examples, storytelling and abstract concepts without being too much in the founders’ business.
2. Finding a rhythm and discipline to be free and still productive.
3. Learning how to empathize with the other person.
4. Understanding stakeholder dynamics and being situationally aware.
5. Building trust, knowling how to get feedback and how to influence the people who do not directly report to you.

“Those soft skills are super important in venture, they’re just utilized in different ways in VC than in operating.”

Finding the best fit startups.

Stride VC sounds very poetic, so I’ll just end with an extensive quote from Cleo’s conversation with Aarish on Nothing Ventured that captures that spirit and what she and other partners at Stride look for in the projects they back.

“When I was looking at potentially joining a venture fund, what was really important to me was really the software aspects of it, the vision and the values and what size of team, what stage you’re joining the fund at. What I really found alignment in was the ethos of Stride and the fact that it’s still a startup.”

“We really believe that the job is a privilege and that we need to earn our seat at the table to be with the founders.”

Listen to the entire conversation with Aasrish Shah, linked above.