ABOUT THIS EPISODE
Rahul Vohra is the founder of Superhuman, the email client that was acquired by Grammarly. Grammarly has since taken on the Superhuman name, and Rahul now leads Superhuman Mail. Before Superhuman, he built Rapportive, the first Gmail extension to scale to millions of users. LinkedIn acquired it 20 months after its first line of code. Rahul studied computer science at Cambridge, ran Cambridge University Entrepreneurs, and went through Y Combinator in Summer 2010.
In this episode, Immad Akhund and Raj Suri talk with Rahul about the origin of the Superhuman name, how a leaked demo link took Rapportive from 10 to 10,000 users overnight, and why being early to a new platform still pays off. Most of the conversation covers M&A: how to read a buyer, how to protect your leverage, and what a banker is actually for.
What you'll learn:
- The four things an acquirer needs to be buying for a company to sell at a top valuation
- How Rahul sold Rapportive at a premium with two weeks of runway left, including letting a no-shop period expire
- Why building multiplayer features moved Superhuman's team net dollar retention from about 70% to 122%
- Why founders should be early to every new platform, from browser extensions to ChatGPT apps and MCP
- How the founder "bell curve" changes how much the idea matters
- What M&A advisors actually contribute, and how they pace hot and cold buyers
Chapters:
(00:00) The four things acquirers are really buying
(01:07) How Grammarly became Superhuman
(04:15) Superhuman vs. superintelligence
(07:04) From the BBC Micro to a Cambridge PhD
(09:48) Fundraising on good vibes at Cambridge University Entrepreneurs
(12:22) Building Rapportive
(14:14) The leak that brought 10,000 users overnight
(18:19) Be early to every platform
(20:11) Email's trillion-hour problem
(22:33) Raising before Demo Day and meeting LinkedIn
(23:56) The LinkedIn API deal
(29:21) Does the idea matter? The founder bell curve
(31:33) Going multiplayer: net dollar retention from 70% to 122%
(33:45) Selling Rapportive with two weeks of runway
(44:20) Selling Superhuman: 16 buyers and the banker's real job
