Mudassir Sheikha on Building Careem and the Uber Acquisition

In this September 2023 interview, Careem co-founder and CEO Mudassir Sheikha tells Harry Stebbings that growing up in Karachi taught him resilience. Everyday difficulties with water, power, safety and transport shaped his desire to reduce friction in people’s lives.

Sheikha and co-founder Magnus Olsson did not begin with a single product revelation. After a serious medical event, Olsson wanted to build something meaningful; Sheikha had been reflecting on why Pakistan had produced relatively few large, lasting institutions. Together they mapped problems and opportunities.

Transport stood out from their experience traveling as consultants. Speaking to drivers, whom Careem calls captains, revealed unpredictable earnings and families relying on them. The company started as a corporate car service before expanding into ride-hailing and other services.

Sheikha attributes some difficulty in building large institutions in Pakistan to everyday friction and limited confidence that such institutions can be built. Stebbings raises political, economic and currency risk and a different view of the local culture. Their broad social assessments are opinions, not established explanations for an entire country.

Sheikha argues that unmet needs and limited competition can also create opportunities, while acknowledging the challenges. He says he personally invests in regional startups, so he has a financial interest in that view.

Asked whether founders need passion for a specific problem from childhood, he says the founders’ initial passion was for building something meaningful. Careem’s purpose became simplifying lives and building an organization that inspires others. He says that shared purpose later supported motivation and resilience.

In summer 2012, the founders wanted to launch before drivers became busy again. Building full apps would take months, so they used SMS: drivers sent messages when approaching, arriving and starting or finishing a trip, including odometer readings used to calculate the fare.

Sheikha says Careem did not have product-market fit immediately: drivers were available, but customers did not yet book. The team concentrated on specific use cases, including airport trips with a late-arrival promise and corporate customers, and worked on reliability before demand grew.

One unsuccessful experiment was selling Careem’s technology as a cloud service to limousine companies. Those customers wanted different features from Careem’s own marketplace users, and the team spent significant time building and selling the offering. He describes it as a failure.

He admits Careem sometimes pursues too many ideas and stays with them too long. Persistence can generate useful learning and unexpected opportunities, but it can also burden the organization. He says the company is trying to improve that balance.

Frugality became a company value because the marketplace operated with thin margins and the founders wanted to avoid charging drivers excessively. In an April Fool’s message, leaders asked staff to vote on paying for coffee, printing or electricity; the joke was meant to reinforce attention to waste.

Competing against better-funded rivals required each marketing dollar to stretch further, Sheikha says. He recounts viral campaigns, including a staged Dubai stunt and a Pakistan billboard that drew controversy; he says the local managing director temporarily left the country for safety. These are his recollections, not independently verified incident details.

His advice to underfunded founders is to spend creatively, adapt the product to local needs and prioritize talent. In Saudi Arabia, Careem added cash payments when many customers could not or did not use cards, and it offered phone support. He argues local knowledge can offset some funding disadvantages.

Sheikha says he made a similar case to investors worried about competing with global companies: Careem could prioritize local customers and build relationships with local stakeholders. He cites a Dubai government joint venture for taxi dispatch as an example of a different local approach.

Before a 2016 fundraising meeting, Sheikha and his CFO stayed in inexpensive accommodation with bunk beds and struggled to sleep. He recalls drinking extra coffee and resting in a small car before the meeting. He offers the story as an example of the company’s frugal habits.

He says the first two rounds were particularly difficult because the company was too small for some global investors and the regional market was still developing. During the second round, a lead investor sent two personal bridge payments of $500,000 each while documents were delayed, according to Sheikha’s account.

Sheikha says the acquisition negotiations later created a difficult board split between investors who wanted to sell and those who did not. He feared the disagreement could damage what had been built. Looking back, he wishes he had spent more time building trust with the whole board.

He also thinks an independent, respected chair could have helped manage board relationships and conflicting priorities. Running the business absorbed the founders’ attention, and they tried to address the issue late in the process. This is his retrospective view of what might have helped.

Sheikha recalls first meeting Uber’s Dara Khosrowshahi and Travis Kalanick in Riyadh as Khosrowshahi was arriving as CEO. He says Khosrowshahi asked about Careem’s vision and treated the founders with respect, contrasting that encounter with the earlier competitive relationship.

After earlier discussions failed to produce agreement, a catch-up meeting in San Francisco restarted acquisition talks. Sheikha says the decisive assurance was that Careem could retain its purpose, culture and organization while Uber replaced its shareholders. He saw the deal as an exit for investors and employees without abandoning the mission.

Soon after the transaction closed, the pandemic sharply reduced ride demand. Sheikha says Careem’s business fell about 90% and it reduced headcount. The company accelerated delivery services and launched a broader app in June 2020; these are his account of the period and its response.

The main argument against selling was the risk that Careem’s identity and regional ambition would disappear inside a competitor. Sheikha recalls a leader saying it was the worst money he would make, despite the financial benefit. Some colleagues feared losing the chance to build an enduring independent institution.

Sheikha says Uber supported and funded Careem’s vision and helped with a later spinout involving regional investors. He considers the relationship with Khosrowshahi positive. This is the founder’s assessment of a transaction in which he and the company had interests.

His biggest acquisition regret is that drivers did not benefit more directly from the transaction. He says many employees progressed financially while some captains who helped build the company were still doing similar work years later. He wishes Careem had found a way to share more with them.

The work of leading a larger organization became less about personally recruiting drivers and more about systems, capital allocation and markets. He says such questions were not straightforward in a region with relatively few prior examples of very large technology companies.

On family life, Sheikha acknowledges saying things to his wife about work and sleep that he now regards as unwise. He credits her support and says she helped introduce early services to her network. He also says working intensely left less time to maintain friendships outside work.

He says parenting takes attention because everyday moments offer chances to teach. He and his wife discuss responsibilities and set aside specific areas for him, including financial education. He acknowledges that balancing this with a demanding job is difficult.

Sheikha says his family’s lifestyle did not change dramatically after the acquisition. He wants his children to develop resilience and sees wealth as a responsibility in a region where many people face hardship. These are his personal values and circumstances.

He estimates that the Careem transaction created about 75 US-dollar millionaires and more than 300 in local-currency terms. These are his estimates and depend on the currency and valuation used; the interview does not independently verify them.

Asked what might stop former employees from creating more regional companies, he identifies access to talent and capital and the fragmentation of markets. Separate licenses, entities and payment systems can make expanding across countries much harder than moving between US states, he argues.

Careem’s super-app vision is to provide infrastructure on which other businesses can operate across markets. Sheikha also says the region needs governance and institutional foundations that let companies endure after founders leave or early transactions occur. These are his ambitions, not completed outcomes.

He sees regional stock exchanges, including in Dubai, Abu Dhabi and Saudi Arabia, as potential sources of future liquidity. His optimism that the problem will ease over time is a prediction, not a guarantee of an exit.

On why super-app attempts have struggled, Sheikha says growth financed by abundant capital can mask weak retention and expensive customer acquisition. He cites monthly retention of 60–70% as an example for some businesses, not a universal industry statistic.

Careem aims to improve retention and use across services so it can operate at sustainable margins for participants, he says. Stebbings asks whether the approach will work; Sheikha hopes they can revisit it in five years. The strategy and future outcome remain uncertain.

In a quick-fire round, Sheikha chooses the Prophet Muhammad as a dinner guest and describes modest home improvements as his first luxury purchase after the acquisition. He believes ambitious goals can inspire people, while acknowledging that outcomes still require sustained work.

He says his view on remote work evolved: in 2020 he expected fully remote work to suffice, but by the interview he saw more value in meeting at the office. This reflects Careem’s experience and his preference, not proof that one model fits every team.

He names integrity, ambition and perseverance as traits he hopes his children develop. Looking toward 2033, he hopes Careem will become a household name across the region and reduce everyday friction. These are aspirations, not established results. The conversation ends with mutual thanks.