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Episode Info:

Maia Bittner (@maiab), co-founder @Pinch and @Rocksbox, is a startup advisor and investor, as well as an alumna at Olin College of Engineering. Currently based in San Francisco, she likes "drinking dirty chais, making web sites, and climbing rocks".

In this episode, you'll hear us talk about:

  • How to Negotiate Your Rent (yes, you heard that right!)
  • Entrepreneurship: from kid to adult
  • Social Media, and Vulnerability
  • Self-worth and Independence
  • Business, and Hustle Culture
  • Uncertainty and Risk-taking
  • Death and Decision-making
  • Asymmetric Opportunities
  • Traveling, and Adaptation
  • Ambition, and hard-work
  • Remote, office, or both?
  • NYC, and its culture
  • Imposter Syndrome
  • Start-up loneliness
  • Community in SF
  • Planning


(02:31) How is the community of SF changing? Ambition and incentives.

(05:18) Seizing opportunities: how did Maia learn business?

(08:32) Traveling, Negotiation, and Sales

(13:46) What challenge is Maia currently struggling with?

(15:59) Death or Future Self: two methods for better decision-making

(19:03) Scheduling: to plan or not to plan

(22:06) Work virtually, Live personally

(27:35) Maia's social life: how do you live anonymously?

(38:22) What sets the Olin College of Engineering apart from others?

(41:25) What was the greatest challenge about starting two companies?

(45:36) The biggest lesson that Maia has recently learned

(48:12) Social skills, and social media; Closing thoughts

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