uber, Expedia, leader

The name Dara Khosrowshahi has been everywhere in the news lately. Why? The Expedia CEO of 12 years has officially confirmed reports that he will be joining Uber as its new CEO.

The ride-hailing platform has had its fair share and sometimes self-inflicted misfortunes. In Southeast Asia alone, it is under high scrutiny from the Thai transport authorities calling for a crackdown, it recently paid $9.6 million in fines after the Land Transportation Franchising and Regulatory Board in the Philippines banned it, and is going up against Grab, the region’s unicorn soon to close an investment round of $2.5 billion backed by Toyota, Softbank, and Didi Chuxing.

Who is Mr. Khosrowshahi and what does he bring to one of the world’s most valuable and troubled startups?

A great answer was shared by angel investor Terrence Yang, excerpt below:

In a perfect world, Uber would just hire Sheryl Sandberg. But in the real world, there’s no way Sheryl would ever join Uber. If you were Sheryl, would you? Becoming Uber CEO poses massive downside risk and and only moderate upside for Sheryl.

Among other things, former CEO Travis Kalanick keeps meddling/trying to come back, Uber has massive problems with recruitment and retention, Uber is highly unprofitable and probably needs (not wants) driverless cars to happen sooner than later to make the economics work (but Alphabet’s Waymo is suing Uber for, shall we say, inappropriately appropriating and basically colluding with Lewandowski to steal Waymo’s self-driving tech).

Here’s what’s great about Dara:

  • Dara is a grown-up Travis. Like Travis, Dara was and remains ruthless, smart, tough. But unlike Travis, Dara developed empathy and soft skills that Travis failed to do for years. Dara is also much more humble and learns fast, including learning soft skills.
  • Travis was the right person to lead Uber when he did. Uber was the fastest growing big startup company in the world by some measures. It’s a truly impressive accomplishment. Travis will go down in history for that. But Travis also went down – because Travis never evolved. Dara did. That’s why Dara is the best realistic choice for Uber.
  • Jeff Immelt and Meg Whitman just don’t know much about the travel industry. I don’t see how leading GE, eBay or HP is very relevant to leading Uber. Dara’s experience is much more relevant (and, no, you are not going to be able to hire the CEO of Lyft right now).
  • Dara bought HomeAway, which competes with Airbnb. Expedia also tried to compete with Airbnb directly. Airbnb is a good model of how to technically violate laws (e.g. turning homes into hotels) without pissing off so many people. Unlike Uber. And Dara is even an investor in freight startup Convoy. Uber is trying to make UberFreight a success.
  • Dara started as an investor in Expedia and CFO of that investor. Benchmark is suing Travis in part over Uber’s lack of CFO.
  • Dara learned to be a great CEO of Expedia. He’s been ranked in the top 100 CEOs in 2015 and 2016. Expedia stock and revenues are doing great.

Southeast Asian startups need…adults?

The lack of experienced digital professionals, coined the talent challenge, has always been a looming backdrop to the bustling nature of startups, especially in emerging markets like Southeast Asia. As long as someone was able to get the job done, they were hired. Age was just a number.  

But given the growth of these companies from a team of 10 to 300 in the span of a few short months, businesses need leadership and maturity, two things that usually stem from experience. This is not to say that older means better but that a great leader is able to recognize what a company needs at Stage 1 is completely different than what it needs at Stage 3 and willing to implement the necessary changes.

uber Expedia Dara

Source: Medium, Al Doan

Given the 48-year old’s track record leading Expedia to become “one of the largest online travel companies in the world” and positive reviews by Expedia senior execs, it isn’t surprising that 93% of employees told company review site Glassdoor that they currently approved of his leadership.

How many startups in the region can confidently say their leaders are this well-received?

Probably one of the biggest indicators of his maturity and most importantly, humility, is witnessed from the memo he wrote to Expedia staff regarding his departure obtained by Recode.

“This has been one of the toughest decisions of my life. I’ve had the privilege to run Expedia for 12+ years now, and most of you who have been on this journey with me know it has not been easy going.”

“I have to tell you I am scared. I’ve been here at Expedia for so long that I’ve forgotten what life is like outside this place,” he added.

Best of luck Dara.

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