At Cherubic Tennis Court at Shih Chien University, Matt Cheng, founder of Cherubic Ventures, plays a match against national tennis player Chi-ren Ho. After a tough match, Cheng jokes that without his knee injury, he could have moved faster.
Cheng’s career is diverse. He is one of the few Taiwanese active in Silicon Valley’s mainstream angel investment community. He manages assets worth over $400 million and has invested in unicorns such as Hims & Hers, Flexport, and Calm. His investments also extend to the culinary world, including Michelin-starred restaurant Fujin Tree Taiwanese Cuisine and Champagne, VANNE Yakiniku, and Hikiniku To Come. Cheng has invested in more than 200 companies, some of which have gone public. Twelve of them have become unicorns, with valuations exceeding $1 billion, making him one of the most influential investors in Asia.
Besides his career in venture capital, Matt is also a former world-class tennis player. He was once the number one junior tennis player in Taiwan for both singles and doubles. When asked about his achievements and success, Matt laughs and attributes it mostly to luck.
Matt started playing tennis in elementary school. His father, an avid tennis fan, wanted Matt to exercise more, so he took him to a park to practice with other tennis players. One of them was a tennis coach. After a few sessions, the other players recognized Matt’s natural talent for tennis. They suggested to Matt’s father that he should enroll at Zhongshan Elementary School, a school that had won first place in tennis for 17 consecutive years.
When Matt first started at Zhongshan, he wasn’t the best player. He was strong but not very fast. Thanks to his commitment, the teacher allowed him to join the school team as a trainee and practice with the team, though unlike his teammates, he had to pay for the training. Zhongshan Elementary School was known for its rigorous training. Students had to arrive at school by 6:40 AM, and basic training included 20 laps every day. Being even one minute late meant running an extra lap.
At the time, Matt’s family lived far from the school. When he first joined the team, he often arrived late due to traffic. Matt recalls with a wry smile, “For weeks, I had to run many more laps than others. I remember crying while running.” The training was hard, but he never thought of giving up. With limited options, the only thing he could do was learn to play tennis well.
Growing up, Matt learned to maximize the value of what he had. He was the only paying student on the team and worked harder than anyone else. Seeing his grit and dedication, Matt’s teacher promised that once he became one of the top four players in the country, he wouldn’t have to pay for training anymore. Matt doubled his practice hours each day, planning to surprise his father if he ever reached that goal. When he finally made it to the top four, he ran home excitedly to share the news. His father was stunned and asked, “Did you do something bad? Did you get kicked off the team?”
His father could hardly believe it. This experience shaped Matt’s down-to-earth and hardworking attitude. No matter what hardships he faced, his principle was always to make the best of what he had and ensure he was always progressing. At that time, he was obsessed with tennis, and his determination propelled him to become the top-ranked youth player in Taiwan for both singles and doubles. He represented Taiwan in world-class competitions like the Asian Junior Tennis Championships in Japan and Singapore and the Asian Preliminaries for the Tennis World Youth Cup, and he was later selected for the national team. Since junior high school, Matt trained in the United States. He jokes that thanks to his wins, he never had to buy shoes, clothes, or rackets—they were all sponsored.
Looking back, Matt says his training in the United States broadened his horizons. He observed that Americans and Asians have very different mindsets. Americans look for opportunities, while Asians tend to avoid risks. For example, when faced with the opportunity to start a business, Asians often worry about failure, while Americans think of the potential to become a billionaire.
Breaking the Mold: From PE Teacher to Entrepreneur
Giving up a steady career as a physical education teacher, Matt became the first student-athlete to enter National Taiwan University without athletic recommendations. Typically, student-athletes either go professional or study at the Department of Physical Education at National Normal University and later become PE teachers. Matt was the first to deviate from this path. Originally, he planned to study at a college in the National Collegiate Athletic Association (NCAA) in the United States. However, during a conversation with his father, Matt noticed his father’s longing when he mentioned the National Taiwan University (NTU). Secretly deciding to fulfill his father’s wish, Matt gave up the idea of playing in the United States and applied to NTU. He was successfully admitted to the Department of Information Management, becoming the first-ever student-athlete to be admitted without a sports recommendation. With help from his classmates, Matt quickly caught up academically and even completed his four-year degree in just three years.
Most people learn at a steady pace, based on their experience. But for Matt, if he wants to learn something, he seeks out the best person in the field. His experience in the United States gave him a perspective different from other Taiwanese students. By sharing experiences and leveraging his strengths, Matt quickly learned from his classmates. Ultimately, it was the friends he made on campus that kept him in Taiwan and led him into the world of entrepreneurship.
Once You Are on the Court, You Are on Your Own: Problem-Solving Skills Learned from Tennis
Tennis taught Matt valuable problem-solving skills. Unlike team sports such as baseball or basketball, tennis requires players to rely entirely on themselves on the court. They must determine strategies, decide on their weapons, and figure out how to win if their usual tactics fail. These are decisions that tennis players make daily, often in split seconds.
Matt recalls a memorable match against Australia in Thailand. He had already played for over four hours when he won his singles match, and without rest, he went on to play doubles. The temperature was over 40 degrees Celsius (104 degrees Fahrenheit). After claiming victory, Matt collapsed from severe cramps and was rushed to the hospital. Despite the physical toll, he felt an overwhelming sense of exhilaration.
To Matt, sports and business are similar. To have a chance at success, you must be fully prepared before stepping onto the court. It’s just like when 91APP got listed in Taiwan, or when Hims & Hers rang the bell at the New York Stock Exchange to mark their SPAC listing. At those moments, Matt thought, “We finally made it!” Just like an athlete claiming victory after years of training, Matt’s preparation and dedication eventually led him to success in business.
Turning Challenges into Opportunities: Resilience and Quick Decision-Making
Tennis has given Matt many strengths. Competitive games taught him to analyze quickly and make decisions on the fly. These skills have shaped him into a natural problem solver. His good judgment, ability to make quick decisions, and interpersonal skills—all crucial for venture investments—stem from his years of tennis training.
Matt jokes that he should be talking about entrepreneurial principles, given that he has established two companies valued at over $1 billion. But to him, it’s really about human nature. Hard work is common, but few people have had the unique experiences that shaped Matt Cheng. “Luck doesn’t just happen. I believe it’s the right attitude that gives me luck.”
What is the right attitude? For Matt, it means maintaining a positive mindset, learning from mistakes, and avoiding unnecessary emotional labor and overthinking. A colleague once said they had never seen Matt depressed, even after years of working together. Even when he’s sad, Matt gives himself only two hours to process emotions. He keeps his thoughts positive and flexible, allowing him to identify ideas others might overlook.
“For me, the greatest sense of accomplishment in life doesn’t lie in the results or monetary rewards, but in the success of others.” With a big smile, Matt says his job now is to give opportunities to those who were never favored or were close to giving up. “Every day, I meet many smart people. They tell me how they want to change the world. It makes me look forward to getting up every day to see if there are more interesting things in the world.”
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