Illustration by J.Claeys

Hours after Casper Sleep executives rang the bell at the New York Stock Exchange to inaugurate the mattress maker’s initial public offering in early February, the mood at the company’s downtown New York offices was celebratory. 

CEO Philip Krim was jubilant, while Gregory Macfarlane, then Casper’s chief financial officer, invited employees to join him for a champagne toast, according to one person who was present. Some Casper employees were less upbeat about the IPO, though. The offering priced at the low end of its expected range, resulting in a market valuation less than half of the $1 billion private investors had given it the previous year. Skeptical employees skipped a lavish IPO party at a boutique Brooklyn hotel later that night, feeling it was in poor taste given Casper’s lackluster debut.

Get access to exclusive coverage
Read deeply reported stories from the largest newsroom in tech.
Latest Articles
 
The Takeaway Media/Telecom
What I Hope Substack Changes About Journalism

This week there was a lot of buzz around journalists ditching their newsroom jobs to publish their own newsletters. The trend was chronicled in a New York Times piece, pegged to the news that The Verge’s Casey Newton was breaking out on his own. 

I had to laugh when Ben Thompson, the creator of the subscription Stratechery newsletter, tweeted: “The NYT trend piece on ...

Latest Briefs
 
Judge Blocks White House Move to Ban TikTok Downloads
Startup CEO That Violated Airbnb Rules Steps Down After Investigation
Podcasting Company Wondery Explores Sale
Stay in the know
Receive a summary of the day's top tech news—distilled into one email.
Access on the go
View stories on our mobile app and tune into our weekly podcast.
Join live video Q&A’s
Deep-dive into topics like startups and autonomous vehicles with our top reporters and other executives.
Enjoy a clutter-free experience
Read without any banner ads.
Startups Microsoft
Tech Execs Are Obsessing Over Note-Taking Apps. We Tested Them Out
Investors are newly enamored of note-taking apps, financing startups like Notion Labs, Coda and Roam Research at high valuations.
Profile Media/Telecom Markets
Bourkoff Is Star Media Dealmaker, but Can He Make Shift to Tech?
Aryeh Bourkoff hates wasting time. Rather than checking his overcoat when he goes out to lunch during New York’s frigid winters, the investment banker sometimes asks his assistant to walk with him to the restaurant so she can take his coat with her back to the office.
Exclusive Entertainment
ViacomCBS Probed Sexual Misconduct Allegation Against CEO Bob Bakish
ViacomCBS has been investigating an allegation of sexual misconduct by its CEO, Bob Bakish, according to several people familiar with the situation.
Exclusive Enterprise Cloud
Microsoft’s Changes to Business Software Terms Could Lift Its Cloud Service and Hurt AWS, Google
A change Microsoft made late last year to the terms of service for Microsoft 365, its cloud-based software that includes Word, PowerPoint and Outlook, could drive some companies that use Amazon Web Services and Google Cloud to Microsoft’s Azure cloud service, analysts said.
Exclusive Venture Capital Startups
Better.com Seeks to Ride Refinancing Wave to a $4 Billion Valuation
Low interest rates have prompted a record number of Americans to refinance their homes this spring. An online mortgage loan startup that has seen strong growth from the borrowing surge is now seeking new financing at a sharply higher valuation than at its last influx of cash a year ago.
Venture Capital Startups
Politics Create High-Wire Act for Tech CEOs
In June, after protests against the police killing of George Floyd swept the country, Glenn Kelman, CEO of online real estate brokerage Redfin, wrote an email to his customers in which he committed to doing more to help Black customers find homes in neighborhoods they’ve traditionally been shut out of.