The demigods of tech share their origins in extended hours spent with a monitor and keyboard long before they are deified, fresh concepts materializing through blocks of code. Facebook was channeled through the fingertips of Mark Zuckerberg. Jack Dorsey taught himself how to talk to computers and built Twitter. And Satoshi Nakamoto, whoever and wherever they are, formulated the protocol behind Bitcoin.

As obsessive programmers and architects of never-before-seen algorithms, these figures and others like them develop the platforms that eventually grew well beyond their control—perhaps even their understanding.

But what happens when the process is inverted, when a tech company (or a tech-empowered company) starts with a business model and races to fill in the space with code as it sprouts and grows new limbs?

With Grab in the spotlight for the largest ever SPAC merger that brands the company with a valuation close to USD 40 billion, KrASIA set out to answer that question. To find out what it is like to be part of a company that has reshaped not only the socioeconomic conditions in Southeast Asia but also the physical feel of the region’s urban nodes, I spoke with five people who have worked at Grab in its various phases, from shortly after its inception to the present, each pouring all their energies into tasks at different divisions to make Grab what it is today.

Grab, the friendly anti-cowboy?

The most fundamental transformation in Southeast Asia that Grab has brought forth is the drastic improvement of nascent transportation infrastructure. That’s no small feat in a region where rules are disparate, and regulators may have entrenched interests that are resistant to change.

When Grab was still chiefly a company that made it possible to arrange rides with a few taps on a phone, its existence was defined based on its antagonistic relationship with Uber. It was a “street fight,” as Uber CEO Dara Khosrowshahi described it.

Grab was a foil to Uber’s “cowboy” attitude. Governments didn’t welcome Uber’s “ride into town and announce my arrival” mode of expansion, as one former Grab employee put it. Grab, on the other hand, took a softer, more collaborative approach by consulting with public officials and even shaping initiatives to relieve traffic congestion.

Elsewhere, however, there appeared to be speed bumps. On multiple occasions, Grab’s personnel were summoned by parliamentarians and “screamed at.” While these episodes may have disheartened some entrepreneurs, it was, in fact, performative. Conservative lawmakers had to appear to be upholding the status quo for local stakeholders, while Grab worked behind the scenes with regulators to develop its regional omnipresence.

That relational outlook sculpted by the founders and reflected in their Southeast Asian roots has been key to the company’s success. In 2017, months before Grab absorbed Uber’s Southeast Asia operations, it was clear that this attitude was paying off.

Even so, in some corners within the company, there were shifting impressions about what Grab was becoming. Some staff were strong believers in upholding public interest and driver welfare, but those who were not fluent in the language of data-driven decision-making were often swatted down, even if they felt like their message carried benefits for Grab in the long run.

Through the years, as more people with corporate consulting backgrounds were appointed in roles with ultimate say-so, Grab’s image and the founders’ actions felt increasingly “stage-managed,” one person said. A growing user base and constantly scaling pool of drivers—the fundamentals for Grab’s burgeoning business—and investors’ constant urging to squeeze extra cents out of each transaction were at odds with the human touch, the feeling of being in tune with the little guy, that Anthony Tan still tries very hard to project.

Grab co-founder and group CEO Anthony Tan has shaped an image of affability for his company. Photo source: KrASIA image archive.

War, truce. Then what?

When Uber’s app was still online in Southeast Asia, Grab was facing a multinational company with global brand recognition and fleshed-out tech that was constantly being improved by engineers in the United States. Uber had cash, experience, and technical talent; Grab had Excel spreadsheets instead of automated tools.

There are two ways to view this situation. The first is that Uber’s lead gave it a clear upper hand. But there were people on Grab’s team who had an alternative take. They saw the asymmetry as an opportunity for Southeast Asia’s best and brightest to build out their own variation of Uber’s services, one that chimed with local rhythms and flows.

That was where the rubber met the road. Grab’s driver recruitment involved knocking on car windows at gas stations, jumping into idle cabs at the airport to make five-minute pitches, and walking up to drivers who were grabbing quick bites at food courts. Even engineers were pounding the pavement to ensure they were building the right hyperlocal features that matched users’ expectations and habits of interaction.

When some drivers expressed interest in ferrying passengers for Grab but said they didn’t own smartphones (and hence couldn’t use the company’s app), Grab worked out deals with OEMs to supply phones to them. The company scored an image of friendliness, of being on the side of drivers and customers. Internally, this was delicately balanced against the path to profitability.

The drive to cultivate a healthy supply of drivers—the company’s heftiest expense as it raced to catch up to Uber—paid off. Uber ceded the roads to Grab in March 2018.

Grab’s absorption of Uber’s Southeast Asia operation had choppy moments. Some Uber staff felt like they were downgraded from working for a global firm to a regional provider, and were surprised by the “very local vibe” and hands-on, hyperlocal, “blood and sweat” method of doing things. There was an “invisible disparity” between the crew from Uber that was retained and Grab’s existing personnel—Uber offered many perks to its staff, and there were expectations for these to carry over even though they were not part of Grab’s usual hiring package.

Those awkward transitions were compounded by loyalty induced by Uber’s brand recognition. Many customers still ached for Uber’s far superior user interface and user experience, particularly in Singapore. These were demoralizing moments for various teams in Grab.

But this again presented an opportunity for team members who had it in their fiber to make new things and explore new ideas. As Grab ballooned, there was plenty of negative space that needed filling. Grab was and still is one of the few instances in Southeast Asia where there is space to be experimental so long as a clear objective is defined; the company just needed talented people who could function autonomously.

The push for automation, however, didn’t receive the support that some in the company hoped it would get. Upper management played it safe, amenable to working out processes by hand, fine-tuning them with limited technical support, then digitizing them when the workflow was mapped out. This was an attitude that was in part shaped by the professional backgrounds of Grab’s co-founders.

When the “street fight” with Uber came to an end in March 2018, Grab was the prevailing ride provider in much of Southeast Asia. Photo source: KrASIA image archive.

The third generation of Big Tech

Founders in Silicon Valley—let’s call them Gen 1.0—set out to build things on their own, imbuing their creations with the belief that they were not merely solving problems, they were in fact changing the world. The mission came first, largely because there wasn’t a roadmap for groundbreaking new ways of connecting with customers and users.

Across the Pacific, techies in China—Gen 2.0—imitate, iterate, localize, then innovate. They have an idealistic desire to fundamentally change lives for the better too, whether by facilitating the flow of information or streamlining unwieldy inefficiencies that have been knotted into systems that people must interact with every day. This often comes from a place of scarcity, as Sinovation Ventures founder Kai-Fu Lee eloquently described in his 2018 book AI Superpowers: China, Silicon Valley, and the New World Order, and represents an outlook that tech is the path of least resistance to radical, extreme-scale change.

In the last decade or so, Gen 3.0 of technopreneurs emerged in Southeast Asia, where sharp founders who typically had lengthy stints overseas had an abundance of business models to reference. Overwhelmingly, these founders are not software engineers; their backgrounds often include semesters at Ivy League business schools, typically Harvard, which is where Grab’s Tan Hooi Ling and Anthony Tan met. The ideas of Gen 3.0 founders are maximalist; their decisions and directions are defined by market conditions, drawing a memetic lineage from the pioneers in China rather than the one-size-fits-all belief so often plugged by companies headquartered in California.

These three ways of starting tech or tech-empowered companies are sculpted by the conditions on the ground—what customers think they want, what people really need, and of course, the rules and limits put in place by regulators. All Southeast Asian tech companies that are now household names—Sea Group, Grab, Gojek, Tokopedia, and more—did more than stir up cultural currents; they churned up unstoppable tsunamis. There is little doubt that companies like Grab have fundamentally changed the socioeconomic standings of many people who were and are making a living through the app, even if they are gig workers, and even if many (including their advocates within the company) believe Grab should be doing more for them.

The curse of tech

Tan Hooi Ling has told her story about taxis in Kuala Lumpur on many occasions: as a young woman who worked late nights for McKinsey, she had to take taxis to get home after leaving the office. At the time—more than a decade ago—KL’s taxis were often dingy, the drivers were rude, and some even perpetrated robberies, rapes, and kidnappings. Tan developed an ad hoc “GPS system” to inform her mother of her whereabouts—after getting into a cab, she would send a series of text messages to indicate where she was in the city, marking her estimated time of arrival based on her familiarity with the route home. That is the tale behind the genesis of Grab, which has come a long way from its origins as a taxi-booking app.

True to Tan Hooi Ling and Anthony Tan’s shared MBA background, Grab hired many corporate professionals with consulting experience as the company scaled up. It was a necessary move: there was and still is far too much data to keep track of, and many people to manage, and experience in those arenas is a valuable asset for the company. But former and current staff have described this as “ossification” and “stagnation,” where silos form and fiefdoms follow. This was a significant shift from taking on people who are entrepreneurial, hands-on, inventive in vacuums, and ready to pound the pavement when necessary. Not even half a decade ago, backgrounds mattered less than the drive to build new things and fill in the negative space as the company billowed out. Now, the company is much less agile.

The MBA-ification of Grab has not only shaped how the firm is run but also the organization’s working culture and how leaders who rise through the ranks form relationships with their staff. There is a delicate, funambulist balance between appeasing investors by demonstrating what is termed broadly as growth, and maintaining the respect of employees, vendors, and partners. The current and former Grab team members I spoke to all did their best to strike that balance, but upper management would often tip the scales to work toward flexes to impress venture capitalists, some told me.

People joke that Grab has a curse of rotating CTOs—Wei Zhu, Theo Vassilakis, and Mark Porter each vacated the post in rapid succession. Grab’s current CTO, Suthen Thomas Paradatheth, has held the title since June 2020; he has risen through the ranks since 2015.

If there was deficiency in Grab’s technical muscle, the founders are surely aware. After a visit to Tencent’s headquarters in 2016, Anthony Tan spoke passionately about emulating Tencent at an all-hands meeting upon returning to Singapore. Yet, that desire was tempered with practical considerations. For instance, a “996” work arrangement, where staff are at their desks 9-to-9 each day, six days a week, is a no-go. The road ahead was one where Grab and other tech-empowered companies in the region would shape their own culture by taking cues from both Silicon Valley and China, transmuting those patterns of business to address local norms and regional habits, with a touch that dismantles obstacles in ways that are unique to Southeast Asia.

If Gen 1.0 is a celebration of individual visionaries, and Gen 2.0 has roots in the genius of the crowd, then Gen 3.0 shows us that tech-empowered enterprises can succeed in a third way—nowhere near as aggressive as their counterparts in China, but also more distributed and decentralized than Silicon Valley’s futurist thinkers. It takes a specific type of person to thrive in this environment, where the company exists at the intersection of corporate formality and being a forever-startup.

There certainly were blind spots in Grab’s transition from taxi-booking service to what may eventually be a super app (nodding at Tencent’s multidimensional WeChat), like the absence of automation where it is sorely needed and occasional inhuman touch. These are growing pains, and every business encounters snafus as it hacks through the competition and fortifies its ranks. People who spoke to me said average Grab employees now tend to stick around for about one year before they move on. For some time, even restricted stock units in a company that is likely going public soon have not been strong enough incentives to stem the turnover.

Despite its internal shortcomings, Grab has found a sweet spot for its operational pace—an “in-between” space where its resources carry maximum impact, at least in theory. Grab’s personnel are energetic and, at their core, want to build things that add a sense of newness for their intended users. They function in a setting where expectations and standards are elevated, at times unyielding, and achieved indelible accomplishments. As Grab enters a new phase, one where the company is defined by its ticker symbol, it exemplifies a business methodology that is built on the backs of some of the most assiduous people who call Southeast Asia their home.