Unpacking Rippling vs Deel: corporate espionage and a $16B plot twist

Equity

TechCrunch

Founders, Silicon Valley, Finance, Ipo, Vc, Technology, Business News, Startups, Business, Venture Capital, News, Stock Market, Entrepreneurship, Techcrunch

4.2 • 365 Ratings

🗓️ 14 May 2025

⏱️ 22 minutes

🔗️ Recording | iTunes | RSS

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Summary

Despite courtroom chaos, Rippling is still going full steam ahead. The HR tech startup at the center of an increasingly dramatic legal battle with rival Deel just raised a fresh $450 million in funding at a $16.8 billion valuation, and launched a new “Startup Stack” to woo early-stage companies—winning over Y Combinator as both an investor and a client. The funding lands amid the company’s high-profile legal fight with Deel, which Rippling accuses of movie-worthy corporate espionage, complete with secret crypto payments and decoy Slack channels. Deel has denied the claims and fired back with its own lawsuit, calling Rippling’s accusations a “distraction.” Today on Equity, Mary Ann Azevedo and Charles Rollet are digging into the HR tech showdown from legal drama to IPO implications and global intrigue. Listen to the full episode to hear more about: The alleged spy, Rippling’s evidence, and Deel’s denials YC’s involvement in Rippling’s latest project, and why the move is raising eyebrows The potential impact on IPOs for both companies Equity is TechCrunch’s flagship podcast, produced by Theresa Loconsolo, and posts every Wednesday and Friday. Subscribe to us on Apple Podcasts, Overcast, Spotify and all the casts. You also can follow Equity on X and Threads, at @EquityPod. For the full episode transcript, for those who prefer reading over listening, check out our full archive of episodes here. Credits: Equity is produced by Theresa Loconsolo with editing by Kell. We’d also like to thank TechCrunch’s audience development team. Thank you so much for listening, and we'll talk to you next time. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	This episode is brought to you by Affinity, the most trusted CRM for private capital.
0:17.6	Hello and welcome back to Equity TechCrunch's flagship podcast about the business of startups.
0:23.1	I'm Mary Ann, and this is the episode where we bring on industry experts to help us explore a trend in the tech world and dive deep.
0:30.2	Today I'm joined by fellow TechCrunch senior reporter Charles Relay to dig into the deal versus rippling drama that we have been covering over the past few months.
0:40.8	There's a lot to unpack here, so stay with us. Charles, welcome to the show.
0:44.9	Thanks a lot for having me, Marianne. Appreciate it.
0:47.1	Of course, yeah. So I think there's been a few of us working on these stories over the past couple of months,
0:53.5	probably arguably you more than
0:55.3	anyone. But I'm going to give a quick backgrounder for our audience. First of all, D.L. and Rippling,
1:00.5	both are what you kind of describe as HR tech and payroll companies, both very large with
1:05.7	valuations over $10 billion. They've been competitors for years, kind of mud slinging on social media for a while
1:12.4	now, but things really, really escalated a couple of months ago when Rippling announced a lawsuit.
1:18.3	This was a March against a deal as part of a 50-page complaint alleging racketeering,
1:24.2	misappropriation of trade secrets, interference, unfair competition, aiding and
1:28.5	abetting a breach of fiduciary duty, basically Rippling accused deal of hiring one of Riblings' employees
1:37.0	to spy on the company. So that happened in March, deal vehemently denied that it did anything wrong legally, and then
1:46.8	itself filed its own countersuit against Rippling in late April. In between, there's been a ton of
1:53.2	things going on. Charles, do you want to kind of fill in some of those gaps? I mean, there's so much
1:58.3	to cover. It's a saga, basically. The big focus of the news was
2:02.4	on this alleged spy, like what Ripling claims was deal bribing one of its staff to leak secrets,
2:08.6	trade secrets, to deal. People focused a lot on that, understandably, because this alleged
2:14.0	spy released a affidavit, and this was part of Ripling's case. This alleged spy confessed
	...

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