Guaranteed Positions Limit Opportunities

A discussion about how staying in comfortable, guaranteed positions can limit exposure to better opportunities, based on experiences from startup founders and entrepreneurs.

Key Concept: Surface Area of Opportunity

• When presented with a guaranteed position vs unknown opportunities, people often choose the guarantee
• The "surface area of opportunity" becomes limited when locked into a guaranteed position
• Turning down guaranteed opportunities opens up exposure to potentially better ones

Real World Example: Twitch Acquisition

• After selling company to Twitch, faced decision about staying for earnout
• Advice received: "Quit on day 1" after selling
• Reasoning: "The surface area of opportunity is too wide"
• Actual decision: Stayed for 2 years to secure the earnout
• In retrospect: Should have stayed only 1 year

Missed Opportunities Example

• While at Twitch, passed on opportunity to build "Klaviyo for SMS"
• That exact idea became Postscript, now a multi-hundred million dollar company
• The ecommerce business started later became more valuable than the Twitch earnout
• Learning: Known/guaranteed money can block bigger opportunities

Key Lessons

• Only get to throw your "all" into one thing at a time
• Choose opportunities wisely
• Need to turn down good opportunities to find great ones
• Analogy to dating: Can't meet "the one" while settling for someone who's just "okay"

Framework for Decision Making

• Question if current path is truly what you want
• Be willing to turn down guaranteed money for better opportunities
• Don't talk yourself into opportunities that aren't "the one"
• Remember that staying in guaranteed positions limits exposure to new opportunities