2 posts tagged “medium”
2025
Fell in a hole, got out. (via) This is an absolutely fascinating entrepreneurial war story by Medium CEO Tony Stubblebine, describing how they went from losing $2.6 million per month in 2022 to being monthly profitable since mid 2024.
By the middle of 2022, the readers were complaining that Medium was flooded with never ending get-rich-quick schemes and the founder (Ev) was complaining about clickbait and barely warmed over summaries of other people’s content. [...]
Because of the quality issues, it wasn’t just a matter of cutting costs because if that’s all we did we’d have a profitable business selling access to content that embarrassed us. That might look like business success, but we looked at it as a failure of mission and a way to waste our lives.
Fixing the business was hard. They ended up dropping from 250 to 77 people, breaking the lease (eventually) on a $145k/month office in San Francisco and, most importantly, pulling off a "recap" - a recapitalization, essentially a reset of the cap table.
I've never seen this process described before. Tony shares a lot of details on how it works, including these notes on how to get existing investors to agree to terms that will aggressively dilute their investment:
Mark Suster made the case that for relationship reasons with other investors, new investors don’t actually want to be the ones to force the recap. They’d rather you do it first and the way to do it is for management to threaten to quit. [...]
I can’t quite convey to you how far out of my depth that management-walks strategy is. It’s beyond just that I’ve never seen a recap before. I’m just not that aggressive that I could imagine putting an ultimatum to investors over more than $200M worth of investor rights. And yet, the logic is clear and I did eventually accept that without the recap Medium would fail in the future and my work in between would be for naught. [...]
In order to justify the recap, you have to make the case that you are clearing incentives for the go forward team. That means everyone’s past effort is getting crammed down and only go forward efforts are being rewarded.
2013
Is it realistically possible to work for a startup like Medium with little to no coding and programming knowledge?
Yes, but not as a programmer. If you have other skills you might be able to land a job at a startup that makes use of those.
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