Market Analysis

Understanding Toast’s expected IPO through the lens of Olo’s 2020 results

If Toast's recovery was anything like Olo's ascent, it isn't impossible to grok why its old $5 billion valuation might be a bit too small here in 2021

How to overcome the challenges of switching to usage-based pricing

The shift from pure subscription to usage-based pricing is nearly as complex as going from on-premise to SaaS.

Oscar Health’s initial IPO price is so high, it makes me want to swear

The clear takeaway from the first Oscar Health IPO pricing interval is that public investors have lost their minds. Go public now.

If Coinbase is worth $100 billion, what’s a fair valuation for Stripe?

Mere days after we discussed Coinbase at $77 billion and Stripe at $115 billion in the private markets, those same semi-liquid exchanges have provided a new valuation for the cryptocurrency company. I

Winning enterprise sales teams know how to persuade the Chief Objection Officer

Identifying and supporting anti-champions during the sales cycle helps enterprise software startups close more deals.

A fraction of Robinhood’s users are driving its runaway growth

Borrowing a term from the casino trade, these whales generate the bulk of the company's revenue stream.

Creating a prediction machine for the financial markets

Algorithms are powerful and automated, but they cannot yet manage everything on their own.

Paying $115B for Stripe or $77B for Coinbase might be quite rational

It's hard to overvalue a startup when the public market is willing to double its valuation the moment it starts to trade.

Pandemic-era growth and SPACs are helping edtech startups graduate early

Is there anything specific to SPACs that makes them a better route for edtech companies than a traditional IPO or direct listing?

With software markets getting bigger, will more VCs bet on competing startups?

As startups get more broad and stay private longer, the space into which VCs can invest may narrow.

Inside Rover and MoneyLion’s SPAC-led public debuts

If we are not careful, every entry of this column could consist of SPAC news.

From dorm rooms to board rooms: How universities are promoting entrepreneurship

An increasing number of higher education institutions are investing in entrepreneurial pipelines that help students launch startups after graduation.

Investors’ SPAC push could revamp the private market money game

A new era of venture, or just another temporary weirdness caused by zero-cost money and an overabundance of bored cash?

Coupang files for mega US IPO

Coupang's offering, coming amidst the public debut of a number of well-known technology brands, will be a massive affair.

Will ride-hailing profits ever come?

Let's unpack their latest numbers to see if what these companies are dangling in front of investors is worth desiring.

As more insurtech offerings loom, CEO Dan Preston discusses Metromile’s SPAC-led debut

We spoke to Metromile CEO Dan Preston about what the day meant for his company and learn more the SPAC process for our own enjoyment.

How will investors value Metromile and Oscar Health?

What we learn today will hopefully bear on other insurtech startups that want liquidity during the current cycle.

Is overseeing cloud operations the new career path to CEO?

Amazon, Microsoft and IBM have each elevated people who ran their cloud divisions to the CEO role.

Decrypted: A hacker attempted to poison Florida town’s water supply

Oldsmar is a small town in Florida that became the center of the cyber world this week when a hacker broke into its drinking water supply and tried to poison it. It’s the nightmare scenario that

Are SAFEs obscuring today’s seed volume?

SAFEs have effectively pushed a lot of public signal regarding seed deals, and even smaller rounds, underground.
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