Casper Files for IPO, Casper’s Business, Spotify Ad Targeting

Casper is a tech-enabled company, but so are its many competitors. Trying to win with brand is difficult in a market defined by infrequent purchases. Spotify, meanwhile, is seeking to expand the podcasting market beyond companies like Casper.

Neither and New Follow-Up, Adam Neumann Forced Out, Peloton IPOs

Why Neither/New companies are different than traditional marketplaces, how Vision Fund’s flaws led to Adam Neumann being forced out, and why Peloton has a big opportunity it might not see.

WeWork Delays IPO, Datadog Prices IPO, SoftBank and Going Big

WeWork abandons its IPO, for now, and is likely at the mercy of Softbank. Then, why Datadog is set to have a great IPO, in direct counter to WeWork and a direct rebuke to Softbank’s approach.

The WeWork IPO

The WeWork IPO is defined by audaciousness and excess, all of which is driven by unlimited access to capital.

Uber Questions

Uber’s S-1 raises more questions than it answers

Pinterest S-1, Zoom S-1, The Enterprise-Consumer Flip-Flop

Pinterest’s S-1 shows why too much funding can be bad for startups, while Zoom’s S-1 shows the benefits the come from being great. That, by extension, is a result of the enterprise and consumer markets flip-flopping.