Reflecting on My Failure to Build a Billion-Dollar Company
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Reflecting on My Failure to Build a Billion-Dollar Company
In 2013, at 23, I felt on top of the world.
I'd just sold my company for $5M. Well, kinda.
I'll tell you the story of how I lost it all.
The $5M was in stock in a VC-backed company. But not just any stock.
This company wasn't just... See more
Here it goes! My best attempt at compressing the last eight years of Gumroad into a single article. Includes: Failing to raise money, laying off 75% of the company, building back up and becoming profitable, restructuring our cap table, and more…
https://t.co/m4XHanlvIs
Sahil Lavingiax.comLessons for Founders
Old habits die hard. At YC I would give a lot of advice to founders, so it’s hard not to offer a few thoughts for anyone building a venture-backed silicon valley company.
First: it is your responsibility to have a direct conversation with your customers, constituents, potential employees—whoever. Even if it’s personally taxing,... See more
Old habits die hard. At YC I would give a lot of advice to founders, so it’s hard not to offer a few thoughts for anyone building a venture-backed silicon valley company.
First: it is your responsibility to have a direct conversation with your customers, constituents, potential employees—whoever. Even if it’s personally taxing,... See more
I miss the old Qasar, not the new Qasar
I’ve been lucky to have started four software companies. Every time they end, whether it’s “a good outcome” or “a bad outcome”, it’s universally devastating.
This was an incredibly difficult stretch. Every time something popped up on my calendar I knew it was someone telling me they were leaving the company. These conversations were crushing. All I could think about was finding a way to fix things. We kicked off some really cool product experimentation but we were a Series C company trying to do seed... See more