Grammarly

10 statements across 4 episodes · 6 bullish · 1 bearish · 4 people on the record · first statement Sep 1, 2022 by Yuriy Timen · said 25 times in 7 episodes since 2022 · across every show →

Mentions by year

brought up most by Lenny Rachitsky (11), Yuriy Timen (9), Melissa Tan (2), Jonathan Becker (2), Ethan Smith (1)

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Everything said about Grammarly, oldest first

Sep 1, 2022 neutral
Disclosure
Timen: Grammarly was over-reliant on performance marketing before diversifying
“In the case of Grammarly, it was performance marketing, kind of over-reliance on performance marketing during, you know, part of the company's life cycle. And so it was like, okay, this thing is working. It's efficient. So you don't want to stop pouring fire o…”
Yuriy Timen Sep 1, 2022 ▶ 39:13 How to grow a subscription business | Yuriy Timen (Grammarly, Canva, Airtable)
Sep 1, 2022 bullish
Prediction Not checkable as stated
Timen: Disciplined companies like Grammarly will win from ad market contraction
“But even right now, during contraction, there are going to be some winners. The companies that had strong cash positions, had strong unit economics, strong payback periods already, right? Grammarly, Canva, to name two that I know personally, a couple of others…”
Yuriy Timen Sep 1, 2022 ▶ 27:23 How to grow a subscription business | Yuriy Timen (Grammarly, Canva, Airtable)
May 7, 2023 positive
Assertion Not checkable as stated
Grammarly scaled to massive success almost exclusively through paid acquisition
“And I think there's some really great examples Of companies that have scaled, you know, in relatively recent times, almost exclusively through paid, like Grammarly is a really good example of this.”
Jonathan Becker May 7, 2023 ▶ 24:55 Mastering paid growth | Jonathan Becker (Thrive Digital)
Mar 17, 2024 neutral
Insight
Lovinsky: Bootstrapped culture can hinder companies needing to invest ahead of growth
“In moments that were like in, in that we're in like today, that can also be detrimental. Right. Cause like the business gets to a certain size. You start getting to kind of like log large numbers. You need to start thinking about, you know, are there other pro…”
Noam Lovinsky Mar 17, 2024 ▶ 56:01 The happiness and pain of product management | Noam Lovinsky (Grammarly, FB, Thumbtack, YT)
Mar 17, 2024 negative
Assertion Not checkable as stated
Lovinsky: Arc browser makes it difficult for Grammarly to work
“I think there's a few things that the Arc browser is doing that make it hard to get Grammarly to work either on the client or in the browser.”
Noam Lovinsky Mar 17, 2024 ▶ 1:07:03 The happiness and pain of product management | Noam Lovinsky (Grammarly, FB, Thumbtack, YT)
Mar 17, 2024 positive
Assertion Not checkable as stated
Lovinsky: Grammarly was profitable from day one and remains profitable
“The company has been around for 15 years and was profitable from day one and continues to be quite profitable.”
Noam Lovinsky Mar 17, 2024 ▶ 50:37 The happiness and pain of product management | Noam Lovinsky (Grammarly, FB, Thumbtack, YT)
Oct 5, 2025 neutral
Assertion Not checkable as stated
Cheng: Over 90% of Grammarly users are on the free tier
“The Grammarly is a freemium business model, which means that over 90% of our users are on the free service and the rest of it pay for subscriptions essentially.”
Albert Cheng Oct 5, 2025 ▶ 21:35 Finding hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com)
Oct 5, 2025 positive
Insight
Consumer freemium works best when core features are permanently free
“So I think these things are usually why I lean toward make sure that the core value proposition that you're providing users is free and is sort of permanently free. And then you layer on kind of a sampling or a taste of some of the premium features that are on…”
Albert Cheng Oct 5, 2025 ▶ 27:09 Finding hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com)
Oct 5, 2025 positive
Insight
Background utilities rely on activation aha moments far more than daily retention
“One exception is that Grammarly was a different type of product and that you install it and you don't proactively open it every day. So that was kind of interesting to me because I assumed that you should always just focus on existing user retention, but for a…”
Albert Cheng Oct 5, 2025 ▶ 31:16 Finding hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com)
Oct 5, 2025 positive
Assertion Not checkable as stated
Grammarly nearly doubled upgrade rates by sampling paid features for free users
“All of a sudden people were seeing Gramly as a much more powerful tool than they were before, and our upgrade rates like nearly doubled just through this change.”
Albert Cheng Oct 5, 2025 ▶ 24:02 Finding hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com)
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