Success Shifts Entrepreneur Anxiety

Andrew Wilkinson shares his perspective on entrepreneurial anxiety and success, revealing that even after building significant wealth and multiple successful businesses, the feeling of risk and anxiety persists - it just transforms.

• Success Timeline Perspective:

  • References Warren Buffett who made 97% of his wealth after age 55
  • Emphasizes that significant success often happens slowly over decades
  • His own journey took 17 years of consistent work

• Early Days Strategy:

  • Focused on boring, steady businesses while others chased risky startups
  • Aimed to turn $100 into $10-20k annually through compounding
  • Reinvested 70% of profits, lived on 30% (percentage decreased over time)
  • Was often underestimated and dismissed by others

• Current State:

  • Now has nearly 1000 employees
  • Built significant cash reserves and cash flow
  • Created multiple "moats" around the business
  • Better diversified than 10 years ago

• Persistent Anxiety Evolution:

  • Still feels "just as at risk and terrified" as 15 years ago
  • Stakes are different - more employees, bigger responsibilities
  • Describes it as a "dust bowl farmer mentality"
  • Uses "wood chopping" analogy:
    • Started small, chopping wood for $20
    • Grew into owning 15 sawmills
    • Still feels guilty for not "chopping wood" despite success
    • Can't shake the need to perform manual labor despite automation

• Key Insight:

  • Success doesn't eliminate anxiety
  • Anxiety transforms from survival-based to responsibility-based
  • The drive to work hard remains despite achieving significant success