A discussion about Andrew Wilkinson's journey from barista to successful entrepreneur, highlighting the reality of business success rates and the importance of learning from failures.

Business Success Rate Reality

  • Started approximately 10 different projects/companies
  • Only 1 out of 10 worked really well
  • Lost over $10M on various failed ventures
  • Examples of failed ventures:
    • Restaurant (lost $1M)
    • E-commerce business
    • Multiple software businesses
    • Concierge service
    • Blog ventures

Key Learning: First Success Can Be Misleading

  • First business (design agency) was "very easy"
  • Created false confidence about starting businesses
  • Describes it as "walking into the gym and picking up really light weights"
  • Led to overconfidence in starting new ventures
  • Started multiple businesses without proper filtering or understanding of difficulty

Approach to Business Ideas

  • Would start businesses immediately upon having ideas
  • Had "no filter whatsoever" on which ideas to pursue
  • Would think of ideas in the shower and start them that same day
  • Describes it as "constantly starting new stuff"
  • Found it exciting despite the failures

Eventual Strategy Shift

  • Shut down almost all incubated businesses
  • Sold successful business for $7M
  • Shifted focus from starting businesses to investing
  • Learned importance of being more selective with ventures
  • Realized starting companies is significantly harder than initially thought

Financial Impact

  • Had to lay off many people
  • Went through many "hard times"
  • Led to feeling burnt out
  • Eventually led to change in business approach
  • Shifted from operator to investor mindset
13:52 - 15:06
Full video: 54:50
AW

Andrew Wilkinson

Co-founder of Tiny

Wilkinson is the co-founder of Tiny Capital, which owns companies including AeroPress, MetaLab and Dribble. He is also the co-founder and chairman of WeCommerce, a holding company that starts, buys, and invests in the world’s top Shopify businesses.

TwitterLinkedIn
Founder
Author
Investor