Today I’m sharing something that’s been a long time in the making:
My friend
and I recorded a podcast with , the CEO and cofounder of Substack at Substack’s headquarters in San Francisco.
Substack was born in 2017 when Chris Best,
i, and came together. Chris and Jairaj had just wrapped up their time at Kik (they were cofounder and head of platform). Hamish had a background in journalism and had been doing communications work for the company.
They were watching the media industry collapse — Craigslist killed classifieds, Google and Facebook dominated ads, and social media was warping the entire news cycle into clickbait and outrage. Writers were losing their jobs. Trust was collapsing. The internet was loud, but not smart.
They believed that good writing still mattered — and that there had to be a better economic model to support it.
They didn’t want more engagement hacks. They wanted a model where the writer wins when the reader wins.
So they built Substack. The first publication was @Sinocism — a China-focused newsletter by
. On launch day, it pulled in six figures. That’s when they knew they were onto something.Substack got into Y Combinator in 2018 and since then it has raised +$100M. Its last round — a $65M Series B in 2021 led by a16z — valued the company at $650M.
Business Model
Substack takes a 10% cut of subscription revenue. There are no upfront costs for creators, but they also don’t offer paid tiers — so they win when you win.
As of 2023, 90%+ of their revenue comes from the top 5% of creators. This concentration makes high-performing writers critical to their long-term success.
They’ve resisted ads… though they’re testing support for podcasters looking to monetize with sponsors.
Traction
1M paid subscriptions in 2021
2M in 2023
3M+ in 2024
+5M in 2025
+20M+ monthly active users
$20M generated by Substack’s top 10 writers
Substack’s own recommendation engine drives 40% of all subs and 12% of paid ones. It’s not just a tool — it’s a marketplace.
Enjoy the podcast!
Cheers,
Guillermo
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