On this episode of Get the Check, the trio kicks things off with a vulnerable chat about work besties (RIP to Maya’s). The hosts cover Grammarly’s relevance post the rise of AI, Rhode’s $1B exit, and why venture capital is taking a page out of the private equity playbook.

Grammarly just raised a billion dollars in funding from General Catalyst, but the twist is they’re not giving up equity. The hosts break down how non-dilutive revenue-based funding rounds work (think Mr. Wonderful on Shark Tank). They also discuss why this deal makes sense at Grammarly’s stage. Next, they unpack why Grammarly is still doing $700M ARR and has huge enterprise logos, despite many people now using AI to correct their writing. They end the segment by talking about Grammarly’s future after acquiring Notion competitor Coda and the product adjacencies like email that Grammarly may expand into.

Next, Hailey Bieber gets the check. Her skincare brand Rhode just sold to e.l.f. for a billion dollars after only three years. The hosts break down why they see this deal as a win-win. Rhode gets access to a more mature company that can help their push from e-commerce to Sephora, and e.l.f. gets to diversify their revenue in the face of Trump’s tariffs. E.l.f. also gets access to an older customer base with a higher propensity to spend.

Lastly, the hosts discuss why VC firms are cosplaying as PE firms these days. They explain how acquiring “boring” small businesses (hi, car washes) and layering on AI software has become the latest VC trend. They break down what makes a good AI rollup target (fragmented, low-margin, could be tech enabled but isn’t) and how this new strategy may impact software revenue models down the line.

00:00 Intro

01:34 Grammarly raises $1B

17:07 Rhode acquired by e.l.f

27:35 VC invests in AI rollups