Jockey Over Horse Investing

Gary Vaynerchuk shares his evolution in investment strategy, focusing on backing exceptional founders over business ideas, learned from missing out on Uber and other experiences.

Core Investment Philosophy

• Completely focused on investing based on the person ("jockey") over the business idea
• Must actively dislike the business idea to not invest if the founder is exceptional
• Believes in founders' ability to pivot and find success even if initial idea changes
• Values founders who can "will their way to success"

Key Lessons from Past Investments

• Missing Uber investment taught him "defense always loses"
• Initially passed on Uber because:
  • Was too conservative with investments until age 35
  • Thought it was founders' side project (wasn't their main focus)
  • Had recently failed with his own side project (wine social network)

Success Stories Using Jockey-Based Approach

• Invested in Mick Mac after one meeting with founder Rachel
  • Company pivoted 4 times but became successful
  • Decision based purely on founder quality ("she's one of us")
• Lost on YoBongo investment
  • Loved the idea (precursor to Tinder)
  • Team couldn't execute despite strong concept

Current Application

• Using this framework to navigate Web3 investments
• Looking for founders who are "one of us"
• Focuses on identifying exceptional operators who can:
  • Navigate market changes
  • Successfully pivot business models
  • Execute consistently despite challenges

Investment Decision Process

• Evaluates founder quality first and foremost
• Business model is secondary consideration
• Looks for natural operators and strong executors
• Values adaptability and persistence in founders