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February 1, 2016

Maggie Hsu on “Engineered Serendipity”, Working with Tony Hsieh, and Revitalizing Downtown Las Vegas

My guest this episode is Maggie Hsu (email), Chief of Staff to Tony Hsieh, CEO of Zappos.com. Maggie is an Advisor at the Downtown Project which treats downtown Vegas like a startup, using $350 million of Tony’s personal funds, to revitalize the city. After she gave me a personal tour and did a shot of Fernet-Branca, I knew something special was happening and I had to share it with you.

There are plenty of cities and downtowns especially, that need a facelift. Master planners have tried and many projects have failed. Well Maggie and Tony have taken a different approach: they have taken the startup process of experimenting, failing, and iterating to city planning. Unheard of.

Maggie provides lessons from getting into Harvard (twice), experimenting with physical space, and creating “story tale moments”. The result is a work in progress but certainly an improved and revitalized downtown Las Vegas. The Downtown Project now encompasses a collection of over 300 investments and operations across small business, technology and real estate.

Maggie is a master learner and successfully cold called her way to become Tony’s Chief of Staff. She combined her ability to learn quickly with her interests in hospitality, city planning, and the idea of serendipity, to join Tony and together, they are figuring out how to revitalize a city.

QUESTION OF THE DAY: What have you seen work and not work in your city to make it a great place to live? Please let me know your thoughts in the comments.

Scroll below for links and show notes…



Selected Links from the Episode
Show Notes
  • Maggie Hsu’s approach to the college selection process [6:05]
  • How Maggie Hsu got into Harvard (twice) [8:00]
  • What was the essay subject of Maggie Hsu’s Harvard MBA application? [10:30]
  • What role does “engineered serendipity” play in the workplace? [11:40]
  • What learning style works best for Maggie Hsu [13:50]
  • What is the hypothesis of the Las Vegas Downtown Project? [16:30]
  • When designing a city like a startup, how do you measure its progress? [21:25]
  • The Gold Spike experiment to start an ice skating rink in the desert [23:50]
  • Why the Downtown Project leaves physical space unfinished [26:09]
  • How long do investors need to wait to get a return in the Downtown Project? [27:40]
  • What are the unconventional ways Maggie Hsu gathers feedback? [30:10]
  • How does local government collaborate with the Downtown Project? [33:25]
  • Where consensus building should take a back seat to taking action [36:30]
  • How a container park creates “storyboard experiences” in Downtown Vegas [39:50]
  • The ceremonial beverage we drank that’s Tony Hsieh’s favorite drink [44:00]
  • Holocracy as a self-management system where management doesn’t exist [47:00]
  • Why Maggie Hsu decided to cold call Tony Hsieh [57:45]
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