Grit How Dropbox Beat Big Tech in the Cloud Wars
29 snips
Aug 25, 2025 
In this conversation, Drew Houston, Co-founder and CEO of Dropbox, shares his journey from coding on a bus stop to challenging tech giants. He discusses the vital role of grit in entrepreneurship and how it means embracing discomfort. They explore the impact of AI on remote work, emphasizing collaboration between humans and machines. Drew reflects on leadership challenges in tech, from startup dynamics to solo CEO experiences, highlighting the importance of self-awareness and personal growth in navigating a competitive landscape.
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Bus-Stop Prototype Sparked Dropbox
- Drew built the first Dropbox prototype on a bus ride after forgetting his thumb drive and wrote Python to solve his own pain.
- That frustration-led prototype became the seed for a product millions would use.
Try Being CEO And Learn On The Job
- Don't assume you're not CEO material; most founders learn CEO skills on the job.
- Try the role and iterate — leadership is trainable, not innate.
Hacker News Video Opened YC Door
- Drew used a demo video on Hacker News to get attention and an email from Paul Graham within two days.
- That traction forced him to find a co-founder quickly and apply to Y Combinator.
