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.

The Incredible Double Interview: Superhuman and Robinhood | E2090

E2090 • Feb 27, 2025 • 99 mins

In this episode, Jason Calacanis engages in insightful conversations with Raul Vora and Vlad Tenev, exploring product market fit and the founder journeys behind Superhuman and Robinhood. The discussion delves into Jason's investment in Superhuman, examining its market positioning, AI features, and the evolution of its product development. Raul and Vlad share their philosophies on product design, scaling, and the role of customer feedback. The episode also covers Robinhood's origins, its viral waitlist strategy, and its approach to diversification and resilience. Additionally, the conversation touches on crypto regulation, investment trends, and the challenges of capital raising for startups.

Key Points

Superhuman's early success was driven by a focus on speed, seamless user experience, and a strict onboarding process that ensured only highly engaged users joined the platform.
Robinhood's meteoric rise can be attributed to its zero-commission trading model, mobile-first approach, and viral growth strategies, including a highly effective waitlist system inspired by Mailbox.
Both founders emphasize the importance of world-class design, user-centric feedback, and maintaining a scrappy, startup mentality even as their companies scale and navigate the challenges of being public entities.

Speakers

Jason Calacanis

Host • 43%

Raul Vora

Guest • 28%

Vlad Tenev

Guest • 28%

Partners

Chapters

0:00	Introduction and onboarding investor stories
1:03	Sponsor: Lemon.io
1:20	Sponsor: Northwest Registered Agent
1:40	Sponsor: VAPI
1:47	Interview with Raul Vora and Vlad Tenev
2:13	Product market fit and founder journeys
3:25	Jason's investment in Superhuman and market positioning
5:14	AI's role and features in Superhuman
8:11	Execution in product development and user readiness
14:37	Targeting users and competitive advantages
22:23	Evolution and new features of Superhuman
24:37	Tackling spam with Superhuman's AI
27:05	Custom auto labels and email classification
30:08	Sponsor: VAPI
32:03	Superhuman's auto reminders and drafts
34:14	Vlad Tenev and the origins of Robinhood
39:31	Product design philosophies of Robinhood and Superhuman
49:29	Scaling design principles and investment decisions
52:31	Subjectivity in product design
55:14	Customer feedback in product development
1:00:00	Superhuman's subscription model and customer acquisition
1:05:11	PR strategies and news hijacking
1:08:33	Robinhood's waitlist and viral moments
1:12:06	Investment experiences with Robinhood
1:13:35	Navigating company valuation fluctuations
1:15:03	Influences on Vlad Tenev and new Robinhood desktop product
1:20:11	Diversification of Robinhood's business
1:22:02	Company resilience and employee reorganization
1:25:52	Crypto regulation and startup mentality
1:30:05	Investment trends among Robinhood users
1:31:12	Retail benefits for startups and capital raising challenges
1:34:04	Accreditation for private investing and solutions
1:36:37	Financial education and closing remarks

Transcript

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