IVP’s Risky Perplexity Bet; CRV Funds Salestech Startup; OpenAI’s First-Mover Hangover

Jake Cronin and Joe Jordan, cofounders of Siro. Courtesy of Siro.

If you’re tired of digging through piles of websites and adding “Reddit” to the end of your Google searches, you may want to take a look at this red-hot AI-powered search engine startup—which now has the backing of yet another VC.

Perplexity, whose search engine product competes with OpenAI’s ChatGPT and Google’s Bard, is raising around $50 million in funding from IVP at a post-investment valuation of $500 million, Kate Clark and I reported on Tuesday. The latest deal more than tripled the startup’s valuation from its last round in March.

IVP’s investment in Perplexity especially surprised me. The firm is known for its thoughtful growth-stage investing in startups with product-market fit, not risky AI up-and-comers. And, it’s received some flack for its past bets on embattled companies like AI copywriting startup Jasper and virtual events company Hopin. So a bet on a consumer startup like Perplexity that’s going up against Google’s massive search business wasn’t one I expected.