Episode Summary
Executive Summary: Jason Fried discusses launching Hey, a new email service built to rethink email from the ground up, and the backlash with Apple over App Store payment rules. The conversation covers email privacy, tracking pixels, the Screener feature, competition with Gmail/Superhuman, pricing, remote work, and why indie software companies need control over customer relationships and distribution.
Main Topics: Why Hey exists and why email needed reinvention (Priority: 5/5): Fried argues email has been stagnant since Gmail’s 2004 launch and still relies on annoying workarounds. Hey was built as an email service, not just a client, to enable deeper product changes across the full stack. Apple App Store conflict and platform control (Priority: 5/5): He explains Apple’s rejection of Hey app updates over in-app payment rules, the threat of being removed from the App Store, and why he views this as unfair, inconsistent, and anti-competitive. Privacy, screener, and anti-tracking stance (Priority: 5/5): Hey blocks spy pixels, rejects default email tracking, and introduces the Screener to force first-contact consent, aiming to give users control over attention and personal data. Competition with Gmail, Superhuman, ProtonMail, and Fastmail (Priority: 4/5): Fried distinguishes Hey as a premium, vertically integrated email provider, unlike Gmail’s free ad-based model or Superhuman’s client-on-top-of-email approach, while welcoming competition and imitation of good ideas. Pricing, customer support, and business model (Priority: 4/5): He discusses the $99/year personal plan, strong early conversion, heavy support load, and a future work-focused product that will broaden Hey’s business beyond personal email. Remote work and operating a distributed company (Priority: 3/5): Fried frames remote work as a distinct platform, not a virtual office, and argues for more async communication, fewer meetings, and intentional culture-building practices.
Key Arguments: Email has barely improved in 16 years, so there is room for a major product reset rather than incremental client tweaks. Building Hey as an email service gives the team control over the full experience, unlike clients layered on Gmail or Outlook. Apple’s App Store rules are inconsistent and can trap businesses by making customer access and billing dependent on Apple. Customers paying for software should be served directly by the company, not through a platform that blocks billing help, refunds, or discounts. Email tracking should be opt-in, not opt-out, because opening an email should not reveal private data like IP address or device details. The Screener is a natural extension of phone-call screening: users should choose who gets access to their inbox. Competition is healthy; good ideas like the Screener will likely become standard across the industry. Remote work should be redesigned around async communication and autonomy instead of copying office habits into Zoom. Indie companies must protect customer relationships and avoid giving away control to platforms. Hey’s long-term success depends on both personal and work email products, not just the premium personal offering.
Data Points: Hey signup trial: 14 days free - Fried says the Hey trial period is 14 days before the annual fee begins. Hey annual price: $99/year - Personal Hey account pricing discussed during the App Store and business-model segment. Initial launch signups: 170,000+ - Fried says more than 170,000 people signed up for Hey after launch. Early conversion rate: 37% - He reports the first-day cohort converted at 37%. Customer support volume: 25,000 emails in three weeks - He describes the intense support load after launch. Bug fixes completed: 100+ bugs - Fried says the team knocked out over 100 bugs in the early launch period. Company size: 55 people - He says Hey/Basecamp’s company has 55 employees. Support staffing: 5 temps - Temporary customer-service help added after launch. Apple App Store fee: 30% - Central point of contention in the App Store dispute. Credit card processing cost: 1.8% to 2.8% - Fried contrasts Apple’s 30% fee with typical card-processing costs. Estimated review fee idea: $100 to $500 - He suggests a possible paid-fast-review model for App Store app approvals. Remote work background: Basecamp started in 1999 - Referenced while discussing the company’s history and culture. Gmail launch year: 2004 - Used as the last time email felt exciting to him.
Pivotal Quotes: "“The last time email was exciting was 16 years ago when Gmail launched in 2004.”" — Jason Fried: Explaining why Hey was worth building as a fresh email experience. "“People deserve to have control over their own time and attention.”" — Jason Fried: Justifying the Screener and anti-spam/anti-tracking philosophy. "“If I can't be myself, if I can't run my own company my own way, what's the point?”" — Jason Fried: Describing his reaction to Apple’s control over App Store distribution and payments.
Implications: The episode highlights a broader push for user privacy, customer ownership, and platform independence. It suggests premium, independent software can thrive by rejecting ad surveillance and challenging gatekeepers like Apple and Google.
About 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.