This Week in Startups

Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.

Spycraft in SaaS, Rabbit’s Comeback, and Startup Pitch Madness | E2106

E2106 • Apr 2, 2025 • 73 mins

In this episode, Jason Calacanis delves into the intriguing corporate espionage case involving Rippling and Deal, exploring its implications and the competitive dynamics in the tech sector, including Y Combinator connections. The conversation examines the legal and potential criminal aspects, while critiquing the spycraft involved. Board governance and Silicon Valley's culture of rule-breaking are also discussed. Later, Jesse Lyu from Rabbit joins to discuss his Y Combinator journey and Rabbit's new hardware product. The episode wraps up with Founder Friday pitch offs, offering critiques and insights into various startup pitches, including an AI-powered podcast app and a community for women in sports.

Key Points

Corporate espionage between Rippling and Deal has escalated with confessions and legal implications, highlighting the high stakes and aggressive tactics in the competitive SaaS market.
Rabbit's journey through the hype cycle of AI hardware emphasizes the importance of resilience and continuous improvement in the face of fluctuating public interest and market challenges.
The Founder Friday pitch-offs showcase innovative startups, with MedSimple and Osprey advancing due to their compelling business models and demonstrated traction, while also underscoring the need for clear, concise presentations that effectively communicate value propositions.

Speakers

Alex Wilhelm

Host • 17%

Preroll

Guest • 1%

Jason Calacanis

Host • 58%

Jesse Lyu

Guest • 15%

Partners

Chapters

0:00	Introduction to the Rippling and Deal corporate espionage case
0:36	Sponsor: Kite, Atlassian, and lemon.io
1:14	Jason Calacanis introduces the show and discusses live streaming and podcast improvements
2:09	Launch job openings and role of researchers in podcast production
4:18	The Rippling and Deal espionage case: Details and implications
6:33	Competitive dynamics in tech and Y Combinator connections
7:30	Jason Calacanis's potential conflicts of interest
9:41	Critique of the spycraft in the Rippling case
10:08	Sponsor: Kite
11:31	Further details and legal implications of the Rippling case
16:00	The potential criminal nature and response to the espionage case
19:23	Sponsor: Atlassian
21:44	Appeal of prosecuting high-profile corporate crimes
22:12	Board governance and oversight in CEO misconduct cases
24:28	Company resilience and Silicon Valley's culture of rule-breaking
28:14	Introduction to guest Jesse Lyu from Rabbit
30:01	Jesse Lyu’s Y Combinator experience and Rabbit's hardware product launch
36:20	Demonstration of RabbitOS intern agent and its capabilities
44:43	Future of agent technology and human-agent collaboration
48:51	Founder Friday pitch offs and March Madness competition overview
50:47	AI-powered podcast app, medical education SaaS, and platforms for workplace connection pitches
59:00	Community for women in sports and entertainment pitch and critique
1:06:40	Discussion on monetizing and creating commitment in startup communities
1:08:23	Selection between competing startup pitches
1:10:33	Tips for improving startup pitches and Twist 500 Sweet 16 competition
1:11:46	Shoutout to top companies and social media engagement
1:12:45	Closing remarks and call to action

Transcript

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