20VC: The $3.1BN Meeting That Led an Uber Acquisition, The Battle With Uber; How to Outcompete When You Have 10x Less Cash & The Marketing Campaigns That Led to Pakistan MDs Fleeing and Elon Musk Fanboying with Mudassir Sheikha, CEO @ Careem

Mudassir Sheikha is the CEO and Co-Founder of Careem. Over the last 11 years, Mudassir has scaled the service to more than 80 cities in 10 countries, with 1,400+ colleagues and more than 2.5 million Captains. With such success, in 2020 Uber announced they would be acquiring Careem for a reported $3.1BN. Prior to Careem, Mudassir co-founded “DeviceAnywhere”, a company that was acquired by “Keynote” in 2008 before joining the management consulting firm “McKinsey & Company” in Dubai.

In Today’s Episode with Mudassir Sheikha We Discuss:

1. From McKinsey to $3.1BN Exit to Uber:

• What was the founding a-ha moment for Mudassir with Careem?

• What does Mudassir know now that he wishes he had known at the beginning?

• What does Mudassir believe he is running away from?

2. Finding Product-Market Fit:

• What is the single biggest mistake founders make when trying to find product-market fit?

• Does Mudassir believe you have to do things that do not scale, to scale? What did Careem do?

• What are some of Mudassir’s biggest pieces of advice to founders on finding a core target audience and doing customer discovery the right way?

3. Competing with Giants: How To Win When You Cannot Outspend:

• How did Careem beat Uber when they had 1/100th of their budget?

• What advice does Mudassir have for founders who have competition that is much better funded?

• What is the story of spending the night in bunk beds and barely sleeping before raising $300M the next day? How did that happen?

4. The Acquisition: How it Went Down:

• How did Mudassir and Dara @ Uber first come to meet?

• How did Dara’s approach contrast with the prior approach of Travis Kalanick?

• Why did Mudassir decide to sell and join Uber?

• What were the main reasons or arguments against the acquisition?

5. Talk to me About:

• Careem’s Pakistan MD having to flee Pakistan for his safety post a marketing campaign?

• Elon Musk likes one of Careem’s promotional videos and why?

• An investor who wired $1M with absolutely no paperwork?

• The catch up meeting that turned into a $3BN offer?