The son of a driver and a cleaner who only finished 4th grade, Desmond Lim was the first in his family to attend college.
He started his first business to pay his way through school before going on to roles at Merrill Lynch, MIT, and WeChat. In 2017, he founded Workstream, an automated hiring and HR platform for hourly workers that has raised over $120M from top investors.
During my recent podcast conversation with him, Desmond shared hard-earned wisdom and practical advice for aspiring entrepreneurs and leaders.
Here are some of the key lessons and tactical applications:
1. It's not about where you start, but how fast you grow. Desmond believes in hiring people based on their trajectory and capacity for growth rather than their current skills or background.
He looks for people who are "humble and hungry" — open to feedback and eager to continuously learn and improve. When building your own team, prioritize hiring for potential, drive and alignment with your mission over existing qualifications.
2. Play the long game. Even as a successful founder, Desmond cautions against rushing into starting a company based on an idea you've only thought about for a few weeks.
Since building something meaningful often takes 10+ years, he advises aspiring founders to spend at least 6 months pressure testing their idea, talking to potential customers, and soul-searching to determine if this is truly what they want to dedicate the next decade of their life to. Don't feel pressured to jump on an opportunity right away. Take the time upfront to validate your idea and commitment.
3. Choose your early team very carefully. In the early days of a startup, you will spend an enormous amount of time with your small founding team. Desmond recommends working on smaller projects first with potential co-founders or early hires to test your working dynamic and alignment before committing to building a company together.
Your first 3-5 team members will set the trajectory for the coming years, so be highly selective.
4. Persist through failure and adversity. Desmond shared a story of captaining his high school basketball team that lost every single game their first year.
Undeterred, he kept the team practicing and improving until they made the Singapore national championship 6 years later. At Workstream, he and his co-founders faced constant rejection when first trying to sell door-to-door. The lesson is to expect frequent failure in any ambitious endeavor and simply keep pushing forward. With persistence, you can achieve remarkable things.
5. Stay close to your customers. In Workstream's early days, Desmond and his team spent months knocking on restaurant doors to understand their pain points and get product feedback.
This commitment to customer proximity was key to developing an offering that truly served their needs. No matter what business you're in, invest significant time in talking directly with your target customers. There is no substitute for this type of on-the-ground insight.
6. Rally your team around a mission. Workstream's stated purpose is "to democratize technology for the deskless workforce" - the 2.7 billion global workers in restaurants, retail, hospitality and other industries historically underserved by software.
Desmond credits this mission orientation with attracting employees, customers and investors aligned with their cause. Define an ambitious mission for your own venture that goes beyond just financial goals.
7. Instill shared values to guide decisions. Two of Workstream's core values are "Humble and Hungry" and "One Team, One Stream" (working cross-functionally to serve customers). Desmond and his team regularly refer to these values to navigate forks in the road. Establishing a common set of principles creates alignment and makes day-to-day decision making easier as you scale.
Building a successful company is never a straight line.
But as Desmond has shown, staying true to your purpose, putting in the hard work, and continuously learning and adapting to challenges can lead to extraordinary outcomes.
This issue and interview was so useful Tim. Thank you very much for being the conduit to hear Desmond Lim's wise counsel.