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Why We Sold To Grammarly | Rahul Vohra

Jun 21, 2026 · 1:01:18

Rahul Vohra, founder of Superhuman and now CEO of Superhuman Group after the company's acquisition by Grammarly, argues that email remains the most enduring layer of work identity and that AI will radically transform the inbox experience while distribution and taste-driven focus are the lasting moats in an era of near-zero software costs. He explains that email addresses are owned by companies and serve as the root identity and authentication unit, with professionals spending 3 billion hours daily on email. Voice features like Right With Voice on mobile now drive 30% of usage gains, and the 'Sent via Superhuman' signature still generates 20% of site traffic. The acquisition story reveals that Grammarly independently chose the Superhuman name via a branding agency, leading to the rare rebrand of the acquirer. Superhuman Group operates as a multi-product bundle ($15/$30 per month) spanning email, documents (Coder), writing agents (Grammarly), and proactive AI (Superhuman Go), with priorities on M&A to fill missing categories like chat. Vohra also angel-invests via Todd and Rahul Capital, backing companies like Loyal (which received FDA efficacy approval for a dog lifespan drug) and…

Inside Gusto's Founding Story | Co-Founder & CTO Eddie Kim

Jun 6, 2026 · 54:31

Eddie Kim, co-founder and CTO of Gusto, reveals how the company grew from a 2012 YC startup called ZenPayroll to $1B in annual revenue and 500,000 customers by cracking the small business market against investor skepticism. He credits the 15-year co-founder relationship with Josh Reeves and Tomer London to shared values and radical directness, arguing that packaging feedback undermines trust. Kim describes building Gusto Co-Founder, an AI agent that automates back-office tasks via chat, with a team of five in eight weeks using Claude Code, embodying how the distinction between engineer and designer disappears. He calls the blank canvas problem AI's main barrier to mainstream adoption and predicts solopreneurs will thrive as AI enables anyone to become a builder.

Yahoo Is Striking Back | CEO Shares The Latest

Apr 7, 2026 · 53:50

Yahoo CEO Jim Lanzone and SVP Eric Feng explain how Yahoo is striking back with AI-powered products like Scout and MyScout, leveraging its 700 million users and proprietary data to differentiate from generic chatbots. After being taken private by Apollo in 2021, Yahoo sold off non-core assets and restructured into GM-led units, cutting headcount by 50% while remaining profitable. The company owns its AI tech, using 30 years of search history and unique knowledge graphs to deliver accurate, citation-rich answers that send traffic to publishers, unlike other AI engines. They argue this approach is possible because Yahoo dominates categories like finance (#1) and sports (#2), each with 100M+ monthly users, and that AI is causing a seismic shift in search behavior (Google's lowest market share in a decade). The duo emphasizes that domain expertise now matters more than pure technical skills, and they are planning agentic features that move from information to action, such as booking trips or setting fantasy lineups, to increase user touchpoints from once a day to multiple times an hour.

Inside the $11M YC Startups That Took Over 2025

Oct 19, 2025 · 1:27:39

This episode profiles six YC Summer 25 startups: Frizzle (AI grading for math teachers, saving 10+ hours/week with 98.9% accuracy), Floot (vibe-coding tool for non-coders, 20,000 users in three months, acquired via Reddit competitor subreddits), Sagekit (chat-based automation platform replacing Zapier, building integrations at 5–10 per week, targeting solopreneurs and SMBs), April (voice AI executive assistant for email and calendar, priced at $15/month, initially launched without free trial then corrected), Cacao (dollar app for Brazil using stablecoins, moving hundreds of thousands in volume, focused on remote workers and freelancers), and Flywheel (retrofit remote control for excavators to improve safety, with two Singapore and three US customers, aiming to reduce ~1,000 annual US construction deaths). Each founder shares early mistakes—Frizzle’s underestimating K-12 sales cycles, Floot’s free pricing delaying feedback, April’s no-trial launch, Cacao’s need for regulatory navigation, and Flywheel’s productization challenges—and explains their go-to-market strategies.

The Founding Story Of Zapier (Wade Foster)

Jul 24, 2025 · 51:33

Wade Foster, co-founder of Zapier, recounts the company's 2011 founding as an integration tool born from a forum thread and bootstrapped to scale without raising beyond $1.3 million. He explains how early growth came from answering forum posts with a prototype that converted at 50% despite being poorly designed, and how the company maintained a 'don't hire till it hurts' philosophy. Foster details the decision to avoid VC because customer acquisition costs were low and the business was profitable within a year, achieving breakeven with only tiny monthly losses. He shares two Paul Graham lessons from Y Combinator: focus only on writing code and talking to customers, and target 10% week-over-week growth, which the company sustained for years. On AI, Foster notes that AI is Zapier's fastest-growing category at nearly 300% year-over-year, and the company now offers agents built by non-technical users through natural-language workflows. He argues that seat-based pricing is dying and predicts a shift to usage-based models, while identifying the biggest AI opportunity in legacy industries like healthcare that work with unstructured data.