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Lenny's Newsletter

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Behind the founder: Drew Houston (Dropbox)

  • Drew Houston is the co-founder and CEO of Dropbox, which has grown under his leadership into a $9 billion valuation company with 700 million registered users.
  • In this article, Drew reflects on three eras of Dropbox’s growth and evolution, the challenges he’s faced over the past 18 years, and lessons he’s learned about managing his psychology as a founder.
  • He emphasizes that as a founder/CEO, you must always be ahead of the company’s growth curve in terms of personal growth, which can be achieved through systematic planning.
  • Drew also highlights the importance of maintaining your learning curve, reflecting on purpose, and building strong support systems, such as therapy, coaching, and meditation, to foster long-term success.
  • The article also discusses Drew’s take on managing founder burnout, taking 100% responsibility for your mistakes, and recognizing the seniority gap as companies scale.
  • The interview also touches on business cycles, effective marketing strategies, and the importance of self-reflection and introspection.
  • Drew shares his experience in building Dropbox from viral growth to battling all tech giants at once, to reinventing the company for the future of work.
  • He also mentions the importance of balancing high-potential talent with experienced leaders who can mentor them.
  • Drew also shares his viral YC hack, which is a perfect example of figuring out who needs to paying attention to you and working backward.
  • Finally, the article discusses some of Drew’s recommended books and his involvement in other tech companies, such as X, Automattic, and GitLab.

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