Episode #333: Against The Wind
“The challenging times that we are facing reveal more than what we should do—they reveal who we should be.”
In a deeply personal and thought-provoking conversation, Jeshua Soh, a Singaporean entrepreneur who has spent the last several years building a life and business in Myanmar, joins the podcast. His journey is marked by a belief in the power of human agency, values-driven entrepreneurship, and a firm commitment to service, even in the face of overwhelming political instability and humanitarian crisis. He traces the arc of his unlikely connection to Myanmar, starting with a teenage school trip in 2012. Captivated by what he calls its “time-capsule-like” quality, and similarities to his own country—both former British colonies with shared legal and educational structures—he felt a subtle but growing pull to return. “It was an incremental thing…a seven-year journey,” he recalls, noting that it also included volunteer work at an orphanage, solo backpacking, and serendipitous connections with the Myanmar diaspora in Singapore.
Jeshua admits that he has not followed the typical path of a Singaporean youth. He bypassed national exams through direct admissions, and then dropped out of one of Singapore’s most elite junior colleges to pursue filmmaking—a field few of his peers considered. “That sort of huge deviation was the beginning of many deviations,” he says. Another was his decision to become an entrepreneur, which began partly out of necessity, and partly out of serendipity. After a period of freelance media work where he collected a bunch of video equipment, Jeshua realized he wouldn't be able to use it during his upcoming period of mandatory national service. So he started a video equipment rental business, which eventually led to founding a second company focused on video production for startups, a shift that exposed him to the world of tech innovation.
The immediacy of needing to hire people for his business eventually pushed Jeshua to explore new options. He had already experienced high turnover among both global freelancers—many of whom quickly left for better-paying jobs—and local staff in Singapore. By that point, he had traveled to Myanmar multiple times, developed personal ties through volunteering and friendships with Burmese people, and had grown to believe in the local talent. So he decided to experiment by opening a small office in Yangon and hiring local staff—an experiment that proved highly successful.
There, he found employees to be hard working and committed. As the team stabilized and thrived, word spread among Jeshua’s network, especially among startup founders who faced the same challenges he had. Because Jeshua had become a valuable bridge between foreign companies and local Burmese talent, they started contacting him in higher numbers, saying. “Hey, since you are in Myanmar, you have a small office, why not we put a few people in your office, and you help me take care of them?”
Before long, the staff working in his Yangon office for other companies outnumbered those working on his own projects! That prompted Jeshua to found a dedicated, HR-as-a-service company, Crosswork, which offers recruiting, office management, payroll, and support for international companies wanting to hire in Myanmar. His company has grown from an original 13 to now over 120 staff.
Jeshua emphasizes that Myanmar has a serious PR problem, especially when it comes to attracting clients and collaborators. To counter the steady stream of negative international headlines—from the Rohingya crisis to the post-coup collapse—he drew on his media background and launched a storytelling campaign. Traveling extensively across the country, he produced more than 125 videos showcasing Myanmar’s people, culture, and regions, aiming to offer a more complete and humanized picture of the country than what typically appears in the news.
More recently, Jeshua has taken on significant humanitarian efforts in hopes of doing something tangible to help others. After learning last year about severe funding shortages at the Mae Tao Clinic near the Myanmar–Thailand border, he cycled from Singapore to Bangkok to raise support. Then this year, in response to even deeper funding cuts—including the suspension of USAID programs—he walked 500 kilometers from Bangkok to Mae Sot, ultimately raising over 150,000 SGD for the clinic. “I couldn’t feel one of my feet by the time I arrived!” he recalls.
But no sooner had Jeshua completed his walk than that devastating earthquake struck central Myanmar. “It wasn’t more than 10 minutes after I arrived in the office that the whole building started shaking!” The quake’s epicenter was a distance away, but the experience further galvanized him to help more. Back in Yangon, he quickly activated his team to coordinate logistics, mobilizing more than 30 volunteers, and partnering with organizations already on the ground. Their relief work spans emergency supplies, clean water, shelter, and solar-powered electronics, especially in off-grid areas that had no reliable electricity even before the earthquake. “There are always going to be risks,” he acknowledges. “From aftershocks, to heatwaves, to military obstruction.”
Another key concern for Jeshua, beyond showcasing Myanmar as a place to invest and his humanitarian efforts on behalf of the Burmese people, is what he sees as the country’s brain drain. “Even if we increase international aid by 10 times… it will not move the needle as much as having just 20% of the diaspora come back!” He emphasizes that Myanmar doesn’t just need investment—it needs educated, skilled individuals who can build, mentor, and lead the country into the future.
Of course, he well understands that safety is an issue for many, and that moreover, he is a foreigner and so it is easier for him to be less personally enmeshed in what is happening on the ground. His concerns are more for the country’s long term development, particularly regarding skilled professionals who have left and do not see a viable future for returning. In this regard, he sees “information asymmetry” as a problem; that is, the way social media amplifies mainly just the success stories of relocation, which tempts even more skilled professionals to leave. In contrast, he stresses that he personally knows dozens of people who have become underemployed overseas. He says wryly that you don’t see social media posts like an engineer saying, “Hey, look, I’m now a DoorDash delivery man!” His efforts are targeted towards Myanmar’s people, particularly the majority who remain in-country. “When you provide them with a job, when you provide economic opportunities… you compound that return,” he argued.
His decision to stay in Myanmar despite all the challenges—even postponing a long-planned retreat in the Himalayas—has been guided by his commitment to the country. He also affirms that he doesn't shy away from Myanmar’s political realities, but he is less interested in dealing with what he cannot control, and instead putting his energies into what he can. When asked whether a more democratic or rights-respecting political environment is critical for his business model, he offers a philosophical response. “I don’t control the politics, but I’m choosing to focus on what I can do in this context,” he says. “None of the Indo-Chinese countries are liberal democracies. You have to take into account the context … and ask who you want to be.”
Jeshua still isn’t sure his bold investment will pay off, but he’s staying the course. “I could be completely wrong … only time will tell,” he admits. But for now, he remains resolute in his decision to bet on Myanmar, and more importantly, its people. “I'm swinging for the fences, going for the long term. My horizon is longer than most people’s! And I think that there is value in a bit of contrarian thinking. Usually, it starts off something like a crazy idea—[that is] until more people start following!”