Cheng was a top-ranked International Tennis Federation world junior tennis player - and he credits that experience for launching him into business his future success.
Today, Cheng is the founder and managing partner of Cherubic Ventures, an early-stage venture capital firm based in Beijing, Taipei and San Francisco with a portfolio of just under one hundred start-ups and young companies.
“A couple of the things I learned were: first, how to get through the hard times, so it helped me to train my competitive personality. And the other thing was people skills, because we had to travel all over the world to different tournaments, and we had to build up our people skills to make friends at every single tournament that we'd go to and every single place we'd go to. You really have to make friends," says Cheng.
Cheng adds that tennis nurtured his competitive streak, which has served him well.
He's now the chief strategist for the giant live social video platform, Tian Ge Interactive, and has repeatedly been ranked as the top investor in the Top 40 under 40 list compiled by the growth promotion site Cyzone.
Cheng's entry into the venture capital space in mid-2004 was an accident, he says. He was recruited by the husband of his former boss, a woman who had managed his internship with Citibank during his senior year at National Taiwan University. She dissuaded Cheng from his planned MBA, and instead he began working for her husband's tech-focused venture capital firm, C Squared.
After six years with C Squared, ultimately as the company's chief China representative, Cheng founded Cherubic in 2010. (The name alludes to angel investment.)
Now, his Cherubic portfolio boasts 90-odd firms. His roster includes Wish, Hyperloop, and Luxe in the United States, Dream Castle and Liulishuo in China, and Pinkoi, 91APP and Chadal across the Asian continent. Together his portfolio companies have raised over $1 billion follow-on financing.
His success reflects his commitment to finding the courage to follow your dream – find inspiration through ensuring your actions align with your passion.
He says the worst advice he's ever received was to stick with tennis, post-graduation, because the game seemed a safe bet.
“That's the path: you have a safe job and you just stick with the path and think it's right. And I'm glad I didn't take that advice," he says, laughing.
“I am really fortunate to live the best life I can," he continues. “I want to get up every day and am able to learn things that most people never have the chance to experience, just like 'cross-border'," he says.
“A lot of people ask me: 'Why do you want to do investment cross-border? It's tough between the US and China.'" His answer: because no one else does, and the potential benefits are big.
The ambitious entrepreneur with a hardcore computer science degree stays sharp by tracking trends through reading tonnes of modern media titles: everything from Venture Beat to Quora, subscribed via the personal magazine hub Flipboard and Twitter. Then he circulates takeaways.
His takeaway from tech giant Apple? It never obsesses on “specs" - the hardware. Apple delivers something that people need, he says, adding that it learns what the market craves through scrutinising society. That's a game plan he's adopted himself.
“I am interested in and curious in all aspects of people's lives," he says.
When assessing a start-up, first he addresses what personal consumer problem it solves, because a winning original idea makes a start-up scalable.
Whatever your concept, you must be committed. Then, he says, as you pursue your tedious start-up journey, you can stick with the program. “It's all about passion."
He's also got a winning formula for those keen to do business in China, which he's christened his "BAT+Q formula". The formula incorporates a nod to Baidu (web services), Alibaba (online auctions), Tencent (investment holding) and Qihoo (security software).
“They are the king of almost everything and they do everything... They are everywhere," he says. You have to understand these companies, he says, and warns against trying to penetrate an internet giant's core business terrain, because it will smash you. Instead, have a road-map.
Those tennis metaphors keep coming: be ready to pivot, he says. Crank out eight apps instead of rashly counting on one, because pivoting keeps you alive when adversity occurs.
But, for Cheng, in the end, game, set and match is all about zeal, which will triumph over strategy each time.
“It's really important to do something that you are passionate – really passionate about."
Contributing Writer: David Wilson
Contributing Photographer: Jasper James