Podcast Summary: This Week in Startups

Episode: Grammarly is now Superhuman! CEO Shishir Mehrotra explains the rebrand | E2201

Date: October 30, 2025
Host: Jason Calacanis
Guests: Alex (Co-host), Shishir Mehrotra (CEO, Superhuman; formerly Grammarly)

Episode Overview

This episode covers a major rebranding in the productivity and AI space: Grammarly is now Superhuman, under the leadership of CEO Shishir Mehrotra (formerly of YouTube/Coda). The discussion begins with labor trends in tech, highlights US-Japan tech and energy partnerships, then turns to the blockbuster interview about the Superhuman rebrand, new product launches, and the future of productivity platforms. The team also covers macro tech topics: energy infrastructure for AI, economic anxiety, robots, Uber’s self-driving push, and Deep Tech company valuations.

Key Discussion Segments & Insights

1. Tech Labor Trends and Employee Well-being

• Sabbaticals and 4-Day Workweeks

  • Referencing 37signals’ unique sabbatical (six weeks every three years) and summer four-day workweek policy for long-term retention (00:00–04:50, 20:00–26:00).
  • Jason Calacanis' perspective:

    “These kind of offerings seem crazy if you were running a large company … however, with a small company you can be 20% inefficient over the summer … if you’ve built a company that’s resilient and you have plenty of people, it doesn’t matter if people go on sabbatical for six weeks.” (02:31)

  • Discussion on the feasibility of these policies in startups vs. enterprises; analogy to luxury brands like Chanel with privileged work arrangements.

• Economic Disruption & Societal Trends

  • Workforce shrinking in Big Tech, automation’s pressure on jobs, and potential future experiments with the 4-day workweek in the US.
  • Wealth polarization, labor–capital relations, and ideas like wealth taxes or doubling teachers as society adapts to technological unemployment (28:00–34:30).
  • Quote:

    "The people who don’t have money are doing much worse than people with money think they are. And I think that’s going to lead to some surprises politically." — Alex (32:17)

2. US–Japan Startup Collaboration & Energy Investments

• Founder University Expansion to Japan (07:16–12:00)
  • Jason announces Launch’s program expansion with JETRO, building a Silicon Valley–Japan bridge for startups, with a call for bilingual hires.
  • Nuclear energy investment deal with Westinghouse, involving U.S.-Japan capital sharing and implications for AI datacenter power needs.
  • National-level + corporate-level movement toward building new nuclear infrastructure to meet AI’s power hunger.
    • “If we’re going to win the AI race, we’re going to need power. And if we don’t get this power dialed in quickly, from all different sources, we’re going to have a real problem.” — Jason (14:20)

3. Major Interview: Shishir Mehrotra on the Superhuman Rebrand

a. Why Rebrand? Grammarly → Superhuman

• Announcement: The parent company formerly known as Grammarly is rebranding to Superhuman, folding Grammarly, Superhuman Mail, and Coda into a single suite and platform. (38:32–43:30)
• Rationale:
  • “Superhuman was the obvious choice. ... The word we are drawn to — I think a lot of people are drawn to the ‘Super’ part, but we were drawn to the ‘Human,’ because ... we make people more human. Everybody else is trying to get AI to replace humans. We’re going the other way around.” — Shishir (41:10)

b. Product Launches: Superhuman Go & Suite Bundling

• Superhuman Go:
  • New AI assistant platform: network of proactive, embedded personal AI agents.
  • Partners can build their own agents or use ones from Superhuman/Grammarly/Coda or third parties (43:35–44:19).
  • Platform is open for partners, already includes agents by 12 other companies; customers can build internal-facing agents as well.
• Bundling & Pricing:
  • New bundled plans: pay for one (Mail/Grammarly/Coda) to get all.
  • Designed for “superfans” to seamlessly try the whole suite (50:29–51:25).
  • “If you are a paid and happy user of Superhuman Mail, then for the same price, you will also get ... three other products alongside.” — Shishir (55:48)

c. Platform & AI Philosophy

• Personal, Embedded AI:
  • Superhuman/Grammarly works everywhere—desktop, mobile, browser, Google Docs, Slack, etc.—for deeply personal, contextual AI assistance (47:17–47:53).
  • Open agent platform will enable radical customization/focus, e.g., “Radical Candor” agent in partnership with Kim Scott as a “teacher/coach” by your side (48:44–49:44).
  • Privacy and data permissions are core to platform design; IT controls are built-in (58:52–62:27).

d. Features, Outlook & Notable Quotes

• “The thing I love about Grammarly is it persistently follows me around my desktop. … It feels like it’s starting to learn, become a little more personalized” — Jason (44:19)
• On AI writing in specific styles (e.g., Hemingway, Kant):

  “If I want to write more like how Kim [Scott] thinks I should write, I want Kim sort of sitting next to me with a marker… For schools ... it’s about bringing your teacher to you.” — Shishir (57:34, 58:31)

e. Company Culture: Sabbaticals, Hybrid, Team Size

• Superhuman (ex-Grammarly) does offer sabbaticals:

  “I don’t think the idea of sabbaticals is that controversial actually. I think people do get burnt out. ... People who take them come back rejuvenated.” — Shishir (65:28)

• Mostly hybrid work: in-office for key culture/mentoring moments, globally distributed (66:04–66:33)

4. Other Major Topics

Nvidia’s Meteoric Rise & AI Infrastructure (68:38–74:36)

• Nvidia hits $5 trillion market cap; P/E ratios scrutinized.
• Massive AI infrastructure investments (OpenAI’s $1.4T claim), questioning sustainability, market rationality.
• Implications of OpenAI’s new structure: for-profit owned by nonprofit, parallels with Mozilla Foundation—potential tax policy and corporate governance impacts.

Humanoid Robots Entering the Home (84:44–91:43)

• 1X company’s NEO robot will sell for $20k or rent for $500/mo; teleoperated for now, but with ambitions for full autonomy.
• Conversation on tech adoption cycles; parallels with early PCs.
• Cost analysis: robots approaching cost parity with human labor for certain tasks.

  “These things, in three years, it’s not going to be uncommon to see one at an airport... or a UPS Store.” — Jason (88:05)

Uber’s Self-driving Moves (92:07–96:09)

• Uber’s alliances with Neuro, Lucid, Nvidia for robo-taxi fleet (Bay Area trial, Level 4 autonomy).
• Uber leverages its driving data and platform to leapfrog back into the autonomy race after divesting its self-driving unit.

Macro View: Local US Policy Fragmentation (96:30–98:28)

• Localized regulatory slowdowns (e.g., Boston voting to ban autonomous vehicles).
• America’s “laboratory of states” effect—diverse, state-by-state adoption or resistance to future tech.

Notable Quotes & Moments

| Timestamp | Speaker | Quote | |------------|---------------------|----------------------------------------------------------------------------------------------------------------------| | 02:31 | Jason Calacanis | “If you’ve built a company that’s resilient and you have plenty of people ... it doesn’t matter if people go on sabbatical for six weeks.” | | 14:20 | Jason Calacanis | “If we’re going to win the AI race, we’re going to need power. And if we don’t get this power dialed in quickly ... we’re going to have a real problem.” | | 41:10 | Shishir Mehrotra | “Superhuman was the obvious choice ... we make people more human. Everybody else is trying to get AI to replace humans. We’re going the other way around.” | | 55:48 | Shishir Mehrotra | “If you are a paid and happy user of Superhuman Mail, then for the same price, you will also get ... three other products alongside.” | | 57:34 | Shishir Mehrotra | “If I want to write more like how Kim [Scott] thinks I should write, I want Kim sort of sitting next to me with a marker...” | | 65:28 | Shishir Mehrotra | “I don’t think the idea of sabbaticals is that controversial actually. People do get burnt out. ... People who take them come back rejuvenated.” | | 88:05 | Jason Calacanis | “These things, in three years, it’s not going to be uncommon to see one at an airport... or a UPS Store.” |

Important Timestamps

• Sabbaticals & 4-Day Workweeks: 00:00–05:13, 20:00–28:24
• US-Japan Announcements/Nuclear: 07:16–18:52
• Grammarly/Superhuman Rebrand Interview: 37:29–66:49
  • Rebrand rationale: 38:54–42:06
  • Superhuman Go/AI agents: 42:18–45:58
  • Product bundling/pricing: 50:29–56:58
  • Privacy & security: 58:52–62:27
  • Company culture/sabbaticals: 65:08–66:49
• Nvidia & AI Infra: 68:38–74:36
• Robot launch/automation: 84:44–92:05
• Uber autonomous strategy: 92:07–96:09

Episode Tone & Flow

Jason Calacanis brings his typical incisive, candid, and sometimes irreverent Silicon Valley tone, with humor and banter between hosts and guest. Shishir’s style is thoughtful and strategic, carefully laying out product logic and broader implications.

For Listeners:

This episode is essential for founders, operators, VCs, and tech observers interested in:

• How leading productivity software companies are building integrated AI experiences
• The challenges and opportunities behind major tech brand unification
• Building future-of-work cultures in an era of automation
• The macro-forces shaping the next decade of the tech economy

Skip ads and routine intros—for key tech news, product launches, and leadership lessons, jump to the marked timestamps above.