Insider Weekends: Dara Khosrowshahi’s $9 Million Purchase Of Uber

Dara Khosrowshahi took on the top job at Uber (UBER) in September 2017 when the company was going through a crisis of confidence and pressure from investors led to the resignation of its CEO and founder Travis Kalanick. Mr. Khosrowshahi who had spent the prior 12 years building Expedia (EXPE) into a travel juggernaut took Uber public in May 2019 at $45 per share and after a lot of ups and downs the stock ended last Friday just below that IPO price. Mr. Khosrowshahi made his largest insider purchase of Uber last week when he spent $9 million on a direct open market purchase of 200,000 shares at an average price of $44.92.

The company has continued to lose money but it was able to offset some of the impact of the COVID-19 pandemic through other lines of business like Uber Eats, delivery of packages and the ability to rent cars. Uber has been on my mind recently after I heard from several friends that Uber rides are costing more these days but people are still using them because they have grown used to the convenience and reliability of Uber. It looks like under Dara, Uber might finally use its scale and network effects to build a diverse line of counter-cyclical businesses that would one day lead to profitability. Prior to Uber, Dara was mentored by Barry Diller at IAC during his seven years at the company and worked as an investment banker at Allen & Co. According to this Recode article,

“Dara is the smartest, most passionate and thoughtful executive I’ve worked with in 25 years,” said Burke Norton, former Salesforce and Expedia senior exec. “He has super high integrity and is a phenomenal leader — the kind of leader whom people would follow into a burning building.”

When I looked at my phone this morning, Uber was offering a discount on its $9.99/month Uber One subscription service that gives subscribers $0 delivery fees and priority service for Uber rides. This is another way Dara is attempting to build a sustainable and predictable business at Uber. When investors think of Uber, they are immediately reminded of its much smaller rival Lyft (LYFT). While both companies are in the ride hailing business, that is where the similarities with Lyft end. Uber is growing faster than Lyft, globally diversified and has better gross and net income margins. While Lyft has a stronger balance sheet, Uber’s has a 12% stake worth nearly $5 billion in Chinese ride hailing service Didi (DIDI) that went public in June 2021 at $14 per share.

It may take some more time before Uber finally becomes cash flow positive but the company appears to be headed in the right direction. It is encouraging to see that several other insiders have been exercising shares without selling them, which we view as a positive signal. The stock is likely to be volatile in the coming months and may provide opportunities to investors to build a position in the company over a period of time. I plan to do a deeper dive into the company in the coming week like I did with Opendoor (OPEN), Airbnb (ABNB) and Netflix (NFLX) in the following three articles,

What Does Zillow’s Exit From IBuying Mean For Opendoor?

Airbnb: Worth More Than Hilton, Marriott and Hyatt Combined

Netflix: A Trillion Dollar Company?

The other interesting insider purchase from last week was the purchase of DraftKings (DKNG) by two of its Directors. We normally see insider sales and DraftKings and this is the first time we have seen insider purchases at the company.  Insider purchases that did not make our top 5 list but were noteworthy include the $2 million purchase of Sarepta Therapeutics (SRPT) by its CEO and a $2 million purchase of PayPal (PYPL) by one of its Directors.

On the sell side, it was interesting to see continued insider selling in Telsa (TSLA) and Opendoor (OPEN) as outlined below.

Welcome to edition 594 of Insider Weekends. Insider buying increased last week with insiders purchasing $150.59 million of stock purchased compared to $140.46 million in the week prior. Selling decreased to $7.55 billion compared to $10.04 billion in the week prior.

Sell/Buy Ratio: The insider Sell/Buy ratio is calculated by dividing the total insider sales in a given week by total insider purchases that week. The adjusted ratio for last week dropped to 50.13. In other words, insiders sold more than 50 times as much stock as they purchased. The Sell/Buy ratio this week was favorable compared to the prior week when the ratio stood at 71.48.

Notable Insider Buys:

1. Coty Inc. (COTY): $10.35

Director Maria Asunicion Aramburuzabala acquired 925,000 shares of this cosmetics company, paying $10.89 per share for a total amount of $10.08 million. These shares were purchased indirectly by Parelia LP.

You can view the list of recent insider transactions for Coty Inc. here.

2. Uber Technologies, Inc. (UBER): $44.23

Chief Executive Officer Dara Khosrowshahi acquired 200,000 shares of Uber, paying $44.92 per share for a total amount of $8.98 million. Mr. Khosrowshahi increased his stake by 20.45% to 1,178,200 shares with this purchase.

You can view the list of recent insider transactions for Uber Technologies, Inc. here.

3. Playtika Holding Corp. (PLTK): $19.73

Chief Executive Officer and Chairperson of the Board of Directors Robert Antokol acquired 150,000 shares of this mobile games, paying $21.62 per share for a total amount of $3.24 million. Mr. Antokol increased his stake by 0.95% to 16,004,800 shares with this purchase.

You can view the list of recent insider transactions for Playtika Holding Corp. here.

4. Illinois Tool Works Inc. (ITW): $241.94

Director Jay L. Henderson acquired 10,000 shares of this industrial products and equipment manufacturer, paying $235.29 per share for a total amount of $2.35 million. Mr. Henderson increased his stake by 112.84% to 18,862 shares with this purchase.

You can view the list of recent insider transactions for Illinois Tool Works Inc. here.

5. DraftKings Inc. (DKNG): $36.14

Shares of this digital sports entertainment and gaming company were acquired by 2 insiders:

• Director Harry Sloan acquired 50,000 shares, paying $39.52 per share for a total amount of $1.98 million. Mr. Sloan increased his stake by 383.58% to 63,035 shares with this purchase.
• Director Woodrow Levin acquired 7,000 shares, paying $36.81 per share for a total amount of $257,670. Mr. Levin increased his stake by 56.02% to 19,495 shares with this purchase.

You can view the list of recent insider transactions for DraftKings Inc. here.

You can view the full list of purchases from this Insider Buying page.

Notable Insider Sales:

1. Tesla, Inc. (TSLA): $1137.06

Shares of Tesla were sold by 2 insiders:

• CEO Elon Musk sold 1,868,182 shares for $1019.21, generating $1.9 billion from the sale. These shares were sold as a result of exercising options immediately prior to the sale.
• Chief Financial Officer Zachary Kirkhorn sold 1,250 shares for $1063.51, generating $1.33 million from the sale.

You can view the list of recent insider transactions for Tesla, Inc. here.

2. Opendoor Technologies Inc. (OPEN): $19.73

Shares of Opendoor were sold by 2 insiders:

• CEO Eric Chung-Wei Wu sold 2,759,109 shares for $21.46, generating $59.2 million from the sale.
• President Andrew Ah Kee Low sold 654,803 shares for $21.67, generating $14.19 million from the sale.

You can view the list of recent insider transactions for Opendoor Technologies Inc. here.

3. Fox Corporation (FOX): $36.32

Chairman Keith Rupert Murdoch sold 1,700,000 shares of Fox Corporation for $40.32, generating $68.54 million from the sale. These shares were sold indirectly through a trust.

You can view the list of recent insider transactions for Fox Corporation here.

4. Arista Networks, Inc. (ANET): $128.96

President and CEO Jayshree Ullal sold 118,000 shares of this networking company for $521.18, generating $61.49 million from the sale. These shares were sold indirectly by various trusts.

You can view the list of recent insider transactions for Arista Networks, Inc. here.

5. Avis Budget Group, Inc. (CAR): $286.3

Executive Chairman Bernardo Hees sold 143,389 shares of this car and truck rentals provider for $272.77, generating $39.11 million from the sale. These shares were sold indirectly through a trust.

You can view the list of recent insider transactions for Avis Budget Group, Inc. here.

You can view the full list of sales from this Insider Sales page.

Disclaimer: Please do your own due diligence before buying or selling any securities mentioned in this article. We do not warrant the completeness or accuracy of the content or data provided in this article.