• 
  Bray Poor

   Himself - Narrator (4 episodes, 2011)
• 
  David Neeleman

  Self - Founder, JetBlue Airways
• 
  Michelle Rhee

  Self - Education Reformer
• 
  Maye Musk

  Self - Mother & Dietician
• 
  Steve Neeleman

  Self - Brother
• 
  Kip Oberting

  Self - KVO Capital Management
• 
  Shang Rhee

  Self - Michelle's Father
• 
  June Morris

  Self - Founder, Morris Travel

• 
  Kimbal Musk

  Self - Brother & Restaurateur
• 
  Inza Rhee

  Self - Michelle's Mother
• 
  Max Chafkin

  Self - Senior Writer, Inc. Magazine
• 
  Michel Del Buono

  Self - Former Analyst, Scion Capital
• 
  Richard Frendt

  Self - Former President, Morris Air
• 
  Richard Whitmire

  Self - Author. The Bee Eater
• 
  Kaya Henderson

  Self - Deputy Chancellor, DC Public Schools

• 
  Steve Jurvetson

  Self - Venture Capitalist
• 
  Elon Musk

  Self - Businessman
• 
  Michael Burry

  Self - Hedge Fund Manager