Remember Grammarly? Of course you do. The briefly ubiquitous piece of software that made sure you were using your possessive apostrophes correctly. Well, guess what? They just received $1 billion in nondilutive investment from General Catalyst to become an all-in-one AI platform?

Sounds like bullshit? Well, probably. But it's a business model we'll be seeing more of. We chat through the rise of zombie AI platforms, before digressing into a chat about Perplexity.

Remember Grammarly? Of course you do. The briefly ubiquitous piece of software that made sure you were using your possessive apostrophes correctly. Well, guess what? They just received <a href="https://techcrunch.com/2025/05/29/grammarly-secures-1b-in-non-dilutive-funding-from-general-catalyst/">$1 billion</a> in nondilutive investment from General Catalyst to become an all-in-one AI platform?
Sounds like bullshit? Well, probably. But it's a business model we'll be seeing more of. We chat through the rise of zombie AI platforms, before digressing into a chat about Perplexity.

The number one podcast about tech business and culture, from James "JR" Hennessy and Raph Dixon.

Down Round

Grammarly's Second Wind

In this short-but-sweet premium ep, Raph and James rattle through some of the biggest stories from the past week, planting flags for later told-you-so's:
Private equity firms are feeling the SaaSpocalypse
Apple's MacBook Neo play
The SNOO
Zuckerberg vs Wang

Plus, Raph describes his whirlwind weekend.

In this short-but-sweet premium ep, Raph and James rattle through some of the biggest stories from the past week, planting flags for later told-you-so's:
<ul>
<li>Private equity firms are feeling the SaaSpocalypse</li>
<li>Apple's MacBook Neo play</li>
<li>The SNOO</li>
<li>Zuckerberg vs Wang</li>
</ul>
Plus, Raph describes his whirlwind weekend.

Teeth, Laptops, Cots and Software

We come to you with an urgent alert for all Down Round subscribers.

We come to you with an urgent alert for all Down Round subscribers.

🚨 Down Round Official Breaking News Announcement Alert PSA

You may know Jack Dorsey as co-founder of Twitter or the guy who runs the company that makes those little card reader doo-dads at your local coffee shop, or perhaps that one random mention in a Kendrick Lamar song.

Right now, he's in the news for laying off a whole hunk of people from Block, the company that owns Square, Afterpay, and Tidal — and he has cited AI as the catalyst. The boys discuss whether this is the beginning of a trend or just a useful excuse.

We also check in on James' dad, and wagers are made.

You may know Jack Dorsey as co-founder of Twitter or the guy who runs the company that makes those little card reader doo-dads at your local coffee shop, or perhaps that one random mention in a Kendrick Lamar song.
Right now, he's in the news for laying off a whole hunk of people from Block, the company that owns Square, Afterpay, and Tidal &mdash; and he has cited AI as the catalyst. The boys discuss whether this is the beginning of a trend or just a useful excuse.
We also check in on James' dad, and wagers are made.

Grammarly's Second Wind

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