In this article, Desmond Lim, co-founder of Workstream, discusses how his experience playing basketball in his youth positively impacted his life and career. While not on the same level of fame as renowned figures like Shaquille O’Neal and David Beckham, Desmond exemplifies the ability of sportspeople to translate qualities such as drive, tenacity, and gumption from the playing field or court into the world of business.
Sports, particularly basketball, have always played a significant part in my life. My love for the game began when I was seven, playing streetball (a casual version of basketball) with my friends. Later, I spent 15 years as a captain of youth basketball teams.
Shooting hoops is always thrilling, but basketball is more than a game; it’s a moulder of character. Basketball has instilled in me values such as teamwork, leadership, hard work and grit. As captain, I’ve learnt how to strategise a play, handle defeat gracefully, and lead players to victory.
My experience in basketball would play a significant role in my journey as a serial entrepreneur, including Workstream, a text-based hiring platform I founded in 2017. I was bitten by the business bug much earlier, launching my first venture after high school. It wasn’t an easy start, but I’m thankful that my extensive experience in competitive sports steeled me to weather the challenges ahead.
Developing the entrepreneurial spirit
Coming from a family of hourly workers, with my mom working as a cleaner and my dad as a driver, I became the first in my family to pursue higher education and venture into the United States on my own. I provided private tuition for students to fund my education at the Singapore Management University (SMU).
During college, my passion for entrepreneurship grew. The success of my tutoring business fueled my ambition. By age 18, I was earning more than my parents. I expanded from one-on-one sessions to group tuitions, creating my own study materials. Then, I established an innovative tutor-to-student matching platform, grouping and matching my friends to students they wanted to tutor.
Encouraged by my tutoring achievements, I started a new venture with two friends—an authentic Thai restaurant called Treehouse, which was based in my school, SMU; I convinced the school board to lease me a space. Afterwards, I noticed a market gap and saw an opportunity to provide affordable and social dining for students. Treehouse became a multifaceted hub, hosting events, live gigs, and catering.
Through these early ventures, I got a valuable crash course in running a company, especially regarding managing operations and finances.
Be hungry to accumulate knowledge
Through playing sports, I learnt to be humble and hungry. On the court, everyone is equal regardless of physical attributes. Sports show that even the less skilled can emerge victorious if they have humility and hunger.
In my early 20s, I was inspired to further my studies in the US after reading amazing stories of successful US companies and their founders. At that time, though, I did not have the financial means to pursue this path, so I worked at Merrill Lynch to gather enough savings first. Along the way, I used Linkedin to reach out to students at prestigious US universities, such as Harvard and Stanford, to gain more knowledge.
When I finally made it to the States and enrolled at Harvard, I was filled with an intense hunger for growth. While most students typically took on four or five classes, I continuously pushed my limits by enrolling in an average of seven classes. I immersed myself in seminars and actively sought out classes across multiple disciplines, such as computer science, law and public policy.
I was driven to take so many classes and learn as much as possible so I could start my own business. Even while I was studying, I launched a business called Quickfast, which is an on-demand house-moving service. This venture failed, but I learnt so much from the process; I raised some seeding funding and even built a team of 10 to 15 people.
The importance of teamwork
Basketball has taught me that victory is not achieved by individual brilliance alone; it requires a collective effort. During my competitive high school basketball days, I remember facing off against an opposing team who had a star player with impressive physical attributes. In contrast, none of us were that outstanding, but collectively we are quite skilled. Ultimately, we managed to defeat this opponent because they were over-reliant on this single player.
Through this experience, I truly grasped the incredible power of teamwork. I took this lesson deep to heart and applied it to Workstream. In fact, one of our core company values is “one team, one stream”.
As Workstream has established hubs across multiple locations, including San Francisco, Vancouver, Singapore, the Philippines, and Utah, I ensured that the person with the right expertise and market knowledge leads each hub. Together, these diverse teams can leverage their unique capabilities and work in sync to carry out Workstream’s mission.
Hard work always pays off
The grit and determination I developed playing sports were crucial during Workstream’s initial stages.
I would go from door to door, engaging in conversations with numerous customers and taking the initiative to speak directly with general managers and even the owners to acquire our first set of users. This approach was not scalable but it helped me secure what we needed.
Using this valuable experience, I developed a sales playbook to facilitate our expansion, going from 10 to 50 customers. Subsequently, I had the privilege of hiring our first two sales representatives, enabling us to acquire our first 100 clients.
Beyond hard work, it’s also about having the conviction to deliver, no matter the circumstances. When we approached our first major client, Jamba Corporate (a juice franchise), our product barely had a wireframe, and there was no software. But I posed Stanford’s Jamba franchise owner, Steven Melt, this question: “If I build it, will you buy it?”. Thankfully, he said yes, and I presented this opportunity to my co-founders, assuring them that he would pay.
Thanks to our conviction and hard work, we were able to deliver the product, and Steven was delighted with the result. He recommended us to other Jamba owners, and our business was able to scale much quicker as a result.
Leadership transformation
Throughout my life, my leadership style has undergone significant changes. From a young age, I always played the role of point guard, a position I held throughout my career. When I became the team captain in middle school, we faced a challenging situation: we lost every game. Motivating my teammates to attend training was difficult because no one wanted to be part of a losing team.
To address this, I took proactive measures, calling and speaking with their parents every week, even memorising their house phone numbers. After two years, my persistent efforts paid off, and my teammates began showing up. Despite being a weak and underperforming team, we achieved our first victory in the third year. As more people joined, we became one of Singapore’s top four teams by the fifth year.
I have also played the role of a servant leader, prioritising serving my teammates and fellow players. As I transitioned from sports to managing companies, my role evolved from a player to a coach. In the early stages of Workstream, with around 30 to 40 people, I excelled at executing tasks, making impactful decisions, and coordinating the team. However, as the team expanded to approximately 250 members, I realised that my role needed to shift further toward empowering my teammates. Today, I embrace the role of a coach, focused on enabling and inspiring my team members to perform at their best.
Listen to the full interview with Desmond Lim here.
