Multiple Success Paths

The discussion explores different paths to success, contrasting traditional corporate ascension (like Brett Taylor's board memberships) with alternative routes (like TJ Parker's post-exit lifestyle). Both speakers emphasize there's no single "right way" but rather finding what aligns with personal values and goals.

Key Points:

• Brett Taylor's Corporate Path:

  • Started as Google PM, created Google Maps
  • Sold company to Facebook for $50M
  • Became Facebook CTO
  • Sold another company to Salesforce for $750M
  • Became co-CEO of Salesforce
  • Now chairman of multiple boards including OpenAI

• Image Crafting Strategy:

  • Deliberately changes appearance and demeanor based on role
  • Dresses like an engineer when needed
  • Shifts to corporate attire for executive roles
  • Maintains careful reputation management
  • Shows poise and timing (example: leaving dinner at right time)

• Alternative Success Path (TJ Parker):

  • Sold PillPack to Amazon for $1B
  • Instead of traditional VC route, focused on passion projects:
    • Built high-end car storage/social club
    • Owns 12-acre farm
    • Produces documentaries
    • Creates art installations for children's hospitals
  • Demonstrates success doesn't require constant corporate climbing

• Key Success Factors:

  • Finding the right "game" to play
  • Being deliberate about reputation building
  • Understanding environment shapes success definition
  • Recognizing multiple valid paths exist
  • Following personal interests rather than conventional routes

• Silicon Valley Impact:

  • Environment shapes definition of success
  • Starting companies seen as normal vs "weird" elsewhere
  • Location can influence career trajectory
  • Social norms affect career choices