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June 4, 2026

Business September 1, 2019 5 mins read

With Upwork’s Stock Down, Will Google Acquire Before Microsoft?

Business ı By Cedric Dent

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Upwork IPO

Over the past 2 earnings reports, Upwork has exceeded the expectations of Wall Street and has shown exceptional results.

First Quarter 2019 Financial Results

  • Gross services volume (GSV) increased by 21% year-over-year to $487 million for the first quarter of 2019
  • Revenue increased by 16% year-over-year to $68.9 million for the first quarter of 2019
  • Core clients grew 22%​ year-over-year to approximately 111,000 as of March 31, 2019
  • Client spend retention increased to 107% as of March 31, 2019, up from 103% as of March 31, 2018

Second Quarter 2019 Financial Results

  • Gross Services Volume (GSV) grew 20% year-over-year to $518.8 million
  • Revenue grew 18% year-over-year to $74.3 million
  • Core clients grew 21% year-over-year to approximately 116,000
  • Gross Margin expanded more than 3 points year-over-year to 71%

The stock spiked up, but then sharply dropped.   Why is that?

Simply put because insiders, all of whom have invested heavily in the Upwork platform, have sold some of their stock.

Is that a bad sign?   No, not at all.

Imagine if you had invested millions of dollars in Upwork as a venture capitalist and/or worked on the platform for years, sacrificing many late nights and weekends toiling away on the platform.   The hard work pays off, and Upwork goes public raising over $180M.

For the first 6 months thereafter you are in a lock-up period whereby you can't sell your stock.   Instead you continue to work away on platform, buildling an even better platform that goes on to have record quarter after record quarter in revenue and user growth.

Then finally the lock-up period expires and you have the ability to sell some of your stock.   Considering the amount of sacrifice you and your family have made to get to this point, it is only natural that top executives along with investors cash some of their stock out.

So insiders sell, that's what happens after lock up periods, which almost always drives down the price of a stock.   An overflow of stock becomes available in the market, which gets gobbled up driving the stock price down further.

And that's where we are, as warned by Don Dion of Seeking Alpha:

"When the Upwork IPO lockup period expires on April 1, pre-IPO shareholders and company insiders will be able to sell large blocks of currently-restricted stock.

  • More than 91 million shares are subject to the lockup period. Just 12.3 million shares are trading pursuant to the IPO.
  • Significant sales could flood the secondary market for UPWK and cause a sharp, short-term decline in share price when the lockup expires.
  • Insiders might be particularly interested in cashing in on some of their profits with UPWK shares having a 33% return from IPO.
  • Aggressive, risk-tolerant investors should consider shorting shares of UPWK ahead of the IPO lockup expiration."

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